PEST CONTROL METHODS ON SOYBEANS - BASF SE (2023)

Soybean pest control method.

Description The present invention relates to pest control methods in soybean crops using isothiazoline compounds of formula (I).

where the variables are defined as follows.

Soy is considered a complete source of protein (Henkel, J., 2000, “Soy: Health Claims for Soy Protein, Question About Other Components.” FDA Consumer (Food and Drug Administration 34(3): 18-20). , soy is a good source of protein. According to the US Food and Drug Administration, soy protein products may be a good substitute for animal products because soy also offers a protein profile." complete.” particularly saturated fats, without requiring major adjustments in other parts of the diet.

Soy protein isolate is very valuable because it has a biological value of 74 (protein quality

Assessment: Report of the joint FAO/WHO expert consultation. Bethesda, MD, USA: Food and Agriculture Organization of the United Nations (Food and Nutrition Paper #51). December 1989). In agriculture, soybeans can produce at least twice as much protein per hectare as other major vegetable or cereal crops, for example. five to 10 times more protein per hectare than land set aside for grazing animals for milk production, and up to 15 times more protein per hectare than land set aside for meat production ("Soybean Benefits," Laboratory National Soybean Research Institute, February 2012). Therefore, soybean can be considered an important world crop that provides oil and protein.

However, soybean plants are susceptible to a variety of bacterial, fungal, viral, and parasitic diseases. For example, soybeans are the second most important agricultural export from the United States after corn.

Consequently, given the importance of soybean in agriculture, adequate pest control is necessary to avoid compromising the productivity and quality of soybean crops. Stink bugs (order Hemiptera, family Pentatomidae) are true animal and insect pests that probably represent one of the most common pest problems in soybeans (Stewart et al., Soybean Insects - Stink bugs, University of Tennessee Institute of Agriculture, W200 09-0098 ). Stink bugs feed on more than 52 plants, including native and ornamental trees, shrubs, vines, weeds, and many cultivated plants such as corn and cotton, as well as numerous non-cultivated plants, and their preferred hosts are almost all wild plants. . They are dependent on these hosts and switch to soybeans later in the season as their preferred foods mature. Stink bugs can feed on many parts of the plant, but they generally target the developing seeds, including the pods, which means that damage to soybeans is the number one concern associated with a stink bug infestation.

Brown or black spots may appear where their mouthparts bury themselves in plant tissue, but there may be little outward signs of feeding damage. Feeding can cause warping, shrinking, or abortion of small seeds. Larger seeds may be only partially discolored due to feeding injury, but this can affect seed quality. High levels of seed abortion can cause the "green bean effect" in which foliage is preserved and plant maturity is delayed (Stewart et al., Soybean Insects - Stink Bugs, University of Tennessee Institute of Agriculture , W200 09-0098).

Stink bugs inflict mechanical damage to the seed and transmit the yeast spot organism. The extent of damage caused by this pest depends to some extent on the stage of development of the seed when it is pierced by the insect's needle-like mouthparts. The younger the damaged seed, the greater the yield reduction. While a late infestation may not affect yields, it will reduce bean oil levels and germination.

The green bug (Acrosternum hilare) is present in certain regions, for example The brown bug (Euschistus servus), one of the most common species that feeds on soybeans, is another common component of the bug complex.

Of the stink bugs found in cultivation, the brown stink bug Euschistus heros is currently considered the most common species from northern Paraná to central Brazil (Correa-Ferreira & Panizzi, 1999) and is a significant problem in the soybean cultivation (Schmidt et al., 2003). The pests appear in soybeans from the vegetative stage and are damaging from the beginning of pod formation until the maturity of the grain. They damage the seeds (Galileo & Heinrichs 1978, Panizzi & Slansky Jr.,15, 1985) and can also pave the way for fungal diseases and cause physiological alterations, as , 1980).

Other herbivorous species that may be present are the red-faced bug (Thyanta custotor) and the red-faced bug (Euschistus tristigmus). Another species, the southern green bug (Nezara viridula), is often restricted to the southernmost counties of the United States. Predatory (beneficial) stink bugs such as the stink bug (Podisus maculaventris) can also be found on soybeans and are sometimes confused with brown or dark brown stink bugs. Control of stink bugs in soybeans is often essential to avoid significant economic damage.

Insecticides commonly used to control stink bugs are pyrethroids, neonicotinoids, and organophosphates, although pyrethroid insecticides are often the method of choice to control stink bugs in soybeans. However, there are increasing problems with resistance to insecticides, particularly in bed bug populations, and in particular to pyrethroids. Euschistus fringes can also be difficult to handle with organophosphates or endosulfan (Sosa-Gomez et al., 2009). Therefore, there is a need for effective alternative methods to control stink bugs in soybeans.

Certain insecticides of the class of gamma-aminobutyric acid (GABA)-dependent chloride channel antagonists (described, for example, in WO 2005/085216 (EP1731512), WO2009/002809 and WO2009/080250) appear to be effective against control stink bugs, especially in soybeans, as described in WO2012/104331.

With respect to the compounds employed in the methods of the present invention, related arylazoline insecticidal compounds are described in WO 2011/092287, WO 2011/073444, WO

2010/090344, WO 2009/112275 and WO 97/23212.

Related arylisothiazoline insecticidal compounds are described in WO 2013/037626 .

However, these documents do not describe compounds having the characteristic substituents and substituent arrangements as claimed in the present invention.

Compounds used in the methods of the present invention are included in

WO2013/092943. Its outstanding aptitude in the processes of protection and treatment of soybeans and its extraordinary activity and efficacy against pests of the Pentatomidae family, stink bugs, particularly against Euschistus spp. and more specifically against the heroes of Euschistus, although it is not described there.

Surprisingly, the compounds of formula (I) have been found to provide effective control of pests in soybean, in particular pests of the family Pentatomidae, stink bugs. Therefore, these compounds represent an important new solution to control pests of the family Pentatomidae, stink bugs, and thus protect soybean plants, crops, and planting material from infestation by these insects, particularly where the insects are resistant to current methods.

In a first aspect, the invention provides a method comprising applying a compound of formula I (Formula I) wherein A is a group A to soybean plants, soybean plant crops, soybean propagation material or to its location¹, AND²of uno³;

in what

AND¹is selected from the group consisting of -C(=NR⁶)R⁸, -S(0)_norteR⁹, e-N(R⁵)R⁶; AND²is a group of the following formula:

(AND²)

in what

# denotes the bond with the rest of the molecule;

W is selected from O and S;

AND³is a group of the following formula:

R7a

R⁵(AND³)

in what

# indicates attachment to the aromatic ring of formula (I);

B¹, B²mi B³are each independently selected from the group consisting of N and CR², provided that no more than two of B¹, B²mi B³They are not; GRAM¹, GRAMS², GRAMS³is G⁴are each independently selected from the group consisting of N and CR⁴, provided that at most two of G¹, GRAMS², GRAMS³is G⁴N sound;

R¹is selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C2-C4-alkenyl, C2 -C4 haloalkenyl, C2-C4 alkynyl, C2-

C₄-Halogenalquinil, C₃-C₆-Cicloalquil, C₃-C₆-Halogencycloalkyl and -C(=0)OR^quince; every R²is independently selected from the group consisting of hydrogen, halogen, cyan, azido, nitro, -SCN, -SF₅, C1-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, where the last four aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or mono- or polysubstituted Radicals R⁸,

-Herr¹²)₃, -O⁹, -S(0)_norteR⁹and not^{10 A}R^10b;

R^3a, R^3bare each independently selected from the group consisting of hydrogen, halogen, hydroxyl, -CO₂R^3d, CC₃-Rent, d-C₃-Halogenalquilo, C₂-C₃-Alquenil, C₂-C₃-Alkynyl, Ci-C₃-alkoxy,

Ci-C₃-halogenalcoxi, C1-C₃-Alkyltio, Cy-C₃- Halogenalquiltio, Ci-C₃-alquilsulfonyl and haloalquilsulfonyl C1-C3; UNED

R^3ay R. S.^3btogether they form a group =0, =C(R^3c)₂, =NO o =NO₃; every R^3cis independently selected from the group consisting of hydrogen, halogen, CH₃y FC₃;

R^3dis selected from the group consisting of hydrogen, C1-C6-alkyl, and C1-C₃-Alquiloxi-Ci-C₃- I rent; each R⁴is independently selected from the group consisting of hydrogen, halogen, cyan, azido, nitro, -SCN, -SF₅, C1-C6-alkyl, which may be partially or fully halogenated and/or substituted with one or more R radicals⁸, C₃-C8 cycloalkyl which may be partially or fully halogenated and/or substituted with one or more radicals R⁸, C2-C6-Alkenyl, which may be partially or fully halogenated and/or substituted with one or more R radicals⁸, C2-C6-Alkynyl, which may be partially or fully halogenated and/or substituted with one or more radicals R⁸,

-Herr¹²)₃, -O⁹, -S(0)_norteR⁹, -NR^{10 A}R^10b,

Phenyl that can be substituted by 1, 2, 3, 4 or 5 radicals R¹¹, and a saturated, partially unsaturated or maximally unsaturated 3-, 4-, 5-, 6-, 7-, 8-, 9-, or 10-membered heteromonocyclic or heterobicyclic ring containing 1, 2, 3, or 4 heteroatoms or the heteroatom contains groups selected from N , O, S, NO, SO and SO2 as ring members, the heteromonocyclic or heterobicyclic ring being substituted by one or more radicals R¹¹; every R⁵is independently selected from the group consisting of hydrogen, C1-C10-alkyl, Cs-Cs-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, where the last four aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/ o o can be substituted by one or more substituents R⁸,

R⁶in a²is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C4 alkyl, bearing a radical R⁸, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl which may be substituted with 1 to 4 substituents selected from halogen and cyano;

-N(R^0a)R^0b, -CH=NOR⁹;

Phenyl that can be substituted with 1, 2, 3, 4 or 5 R substituents¹¹; and a 3-, 4-, 5-, 6-, 7-, 8-, 9-, or 10-membered saturated, partially unsaturated, or maximally unsaturated heteromonocyclic or heterobicyclic ring independently having 1, 2, 3, or 4 heteroatoms or containing groups selected from heteroatoms of N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be replaced by one or more R substituents¹¹; o

R⁵y R. S.⁶together they form a group R⁶in all other cases it is independently selected from the group consisting of hydrogen, cyano, C 1 -C 10 alkyl, C 5 -C 50 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, the last four being aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or substituted with one or more R substituents⁸,

-O⁹, -NR^{10 A}R^10b, -S(0)_norteR⁹, -C(=O)NO^0aN(R^0a)R^0b), -Herr¹²)₃, -C(=0)R⁸,

Phenyl that can be substituted with 1, 2, 3, 4 or 5 R substituents¹¹, mi

a saturated, partially unsaturated or maximally unsaturated 3-, 4-, 5-, 6-, 7-, 8-, 9-, or 10-membered heterobicyclic or heteromonocyclic ring containing 1, 2, 3, or 4 independently selected heteroatoms or groups of heteroatoms containing N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be replaced by one or more R substituents¹¹;

R⁵y R. S.⁶o R⁵y R. S.^6aTogether with the nitrogen atom to which they are attached, they form a 3-, 4-, 5-, 6-, 7-, or 8-membered saturated, partially unsaturated, or maximally unsaturated heterocyclic ring, which ring may also contain 1, 2, 3, or 4 heteroatoms or groups containing heteroatoms selected from O, S, N, SO, SO2, C=O, and C=S as ring members, where the heterocyclic ring may be replaced by 1, 2, 3, 4, or 5 substituents independently selected from the group composed of halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6 -alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic or cycloaliphatic moieties in the last twelve radicals are substituted by one or more radicals R may be substituted⁸, and phenyl which can be substituted with 1, 2, 3, 4 or 5 R substituents¹¹; R^7a, R^7bare each independently selected from the group consisting of hydrogen, halogen, cyano, C1-C6 alkyl, C5-C5 cycloalkyl, C2-C6 alkenyl, and C2-C6 alkynyl, where the last four radicals can be be aliphatic and cycloaliphatic partially or totally halogenated and/or substituted by one or more radicals R⁸;

R⁸is independently selected from the group consisting of cyano, azido, nitro, -SCN, -SF₅, C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, C3-Cs-cycloalkenyl, C3-Cs-halocycloalkenyl, it being possible for the cycloaliphatic parts in the last four radicals mentioned to be replaced by one or more radicals R¹³;

-Herr¹²)₃, -O⁹, -OSO2R⁹, -S(0)_norteR⁹, -N(R^0a)R^0b, -C(=O)N(R^0a)R^0b,

-C(=S)N(R^0a)R^0b, -C(=0)O⁹, -CH=NOR⁹;

Phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents^sixteen, mi

a saturated, partially unsaturated or maximally unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocyclic ring comprising 1, 2, or 3 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2, such as members ring, where the heterocyclic ring is optionally substituted with one or more R substituents^sixteen,

dos R⁸present on the same carbon atom of an alkyl, alkenyl, alkynyl, or cycloalkyl group together form a =0, =C(R¹³)₂; =S; =S(0)_metro(R^quince)₂, =S(0)_metroR^quinceN(R^and)R , =NR^0a, = NORTE⁹; o =NN(R^0a)R⁰;

two residues R⁸together with the carbon atoms of an alkyl, alkenyl, alkynyl or cycloalkyl group to which they are attached form a saturated or partially unsaturated 3-, 4-, 5-, 6-, 7- or 8-membered carbocyclic or heterocyclic ring, the heterocyclic ring comprising 1 , 2, 3, or 4 heteroatoms or groups of heteroatoms independently selected from N, O, S, NO, SO, and SO2 as ring members, and wherein the carbocyclic or heterocyclic ring is optionally substituted with one or more R substituents^sixteen; mi

R⁸is further selected as a substituent on a cycloalkyl ring from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6- haloalkynyl, in which the aliphatic moieties of these six groups can be replaced by one or more R groups¹³; mi

R⁸en grupos -C(=NR⁶)R⁸e-C(=O)R⁸is further selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, and C2-C6 haloalkynyl, wherein the aliphatic portions in the last six radicals can be replaced by one or more radicals R¹³; every R⁹is independently selected from the group consisting of hydrogen, cyano, C1-Ce, C1-C alkyl₆-Halogenalquilo, C₃-C₈-Cicloalquil, C₃-C₈-Cycloalquil-Ci-C₄-alkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the last nine radicals can be replaced by one or more residues R¹³,

-Ci-C₆-C-alkyl(=0)O^quince, -Ci-C₆-Alkyl-C(=0)N(R^4a)R⁴,

-Ci-C₆-Alquil-C(=S)N(R^4a)R⁴, -Ci-C₆-C-alkyl(=NR⁴)N(D^4a)R⁴, -Herr¹²)₃, -S(0)_norteR^quince, -S(0)_norteN(R^and)R , -N(R^0a)R⁰, -N=C(R¹³)₂, -C(=0)R¹³,

-C(=0)N(R^4a)R^4b, -C(=S)N(R^4a)R^4b, -C(=0)O^quince,

Phenyl optionally substituted with one or more R substituents^sixteen; mi

R⁹in groups -S(0)_norteR⁹e-OSO2R⁹is further selected from the group consisting of C1-C6 alkoxy and C1-C6 haloalkoxy;^a, R^10bindependently and independently of each occurrence are selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-Haloalkenyl , C2-C6-alkynyl, C2-C6-haloalkynyl, the aliphatic and cycloaliphatic parts in the last eight radicals mentioned being able to be replaced by one or more radicals R¹³;

-Ci-C₆-C-alkyl(=0)O^quince, -Ci-C₆-Alkyl-C(=0)N(R^and)R, -Ci-C₆-Alquil-C(=S)N(R^and)R, -Ci-C₆-Alkyl-C(=NR)N(R^and)R, C1-C₆-Alcoxi, C1-C6-Halogenalcoxi, C1-C6₆-Alkyltio, Cy-C₆- Halogenalquiltio,

-S(0)_norteR^quince, -S(0)_norteN(R^and)R , -C(=0)R¹³, -C(=0)O^quince, -C(=0)N(R^and) R ,

-C(=S)R¹³, -C(=S)SR^quince, -C(=S)N(R^4a)R⁴, -C(=NR⁴)R¹³;

Phenyl optionally substituted with 1, 2, 3 or 4 R substituents^sixteen; mi

a saturated, partially unsaturated or maximally unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocyclic ring comprising 1, 2, 3, or 4 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as members ring, where the heterocyclic ring is optionally substituted with one or more R substituents^sixteen;

R^{10 A}y R. S.^10btogether with the nitrogen atom they form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the heterocyclic ring may additionally contain one or two heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally bears one or more substituents selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1- C6-alkylthio, C1-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with 1, 2, 3, 4 or 5 R substituents^sixteen, and a saturated, partially unsaturated or maximally unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocyclic ring comprising 1, 2, or 3 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as members of the ring, where the heterocyclic ring optionally bears one or more R substituents^sixteen;

o R^0ay R. S.¹⁰together they form a group =C(R¹³)₂, =S(0)_metro(R^quince)₂, =S(0)_metroR^quinceN(R^and)R , =NR¹⁴you = NO^quince; >11 is independently selected from the group consisting of halogen, cyano, azido, nitro, -SCN, -SF₅, C1-C10-alkyl, Cs-C10-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, where the last four aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or substituted by one or more R radicals⁸,

-O⁹, -NR^{10 A}R^10b, -S(0)_norteR⁹, -Herr¹²)₃;

Phenyl optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from R^sixteen; mi

a 3-, 4-, 5-, 6-, or 7-membered saturated, partially unsaturated, or maximally unsaturated aromatic heterocyclic ring comprising 1, 2, 3, or 4 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as ring members, wherein the heterocyclic ring is optionally substituted with one or more substituents independently selected from R^sixteen;

the dos R¹¹on the same ring carbon atom of an unsaturated or partially unsaturated heterocyclic ring can form a group = 0,

=S(0)_metroR^quinceN(R^4a)R^4b, =NR¹⁴, = NORTE^quince, o =NN(R^4a)R^4b;

the dos R¹¹attached to adjacent ring atoms, together with the ring atoms to which they are attached, form a saturated 3-, 4-, 5-, 6-, 7-, 8-, or 9-membered ring, which ring may contain 1 or 2 heteroatoms or groups of heteroatoms selected from O, S, N, NR¹⁴, NO, SO and SO2 and/or 1 or 2 groups selected from C=O, C=S and C=NR¹⁴as members of the ring, and where the ring is substituted by one or more radicals selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1- C6-alkylthio, C1-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, which with 1, 2, 3, 4 or 5 radicals R can be substituted^sixteen, and a saturated, partially unsaturated or maximally unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocyclic ring containing 1, 2, or 3 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as members of the ring, the heterocyclic ring being able to be substituted by one or more radicals R^sixteen; every R¹²is independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C2-C6 haloalkenyl, C6-alkynyl, C2-C6- haloalkynyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C1-C6-alkoxy-C1-

C6-Alquil, Ci-C6-Halogenalcoxi-Ci-C6-Alquil y

Phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents^sixteen; every R¹³is independently selected from the group consisting of cyano, nitro,

-OH, -SH, -SCN, -SF₅, DC₆-Alcóxi, Ci-C₆-halogenalcoxi, C1-C₆-Alkyltio, Cy-C₆- Halogenalquiltio, Ci-C6-Alquilsulfinil, Ci-C6-Halogenalquilsulfinil, Ci-C6-Alquilsulfonil, C1-C6-Halogenalquilsulfonil, -NR^14aR^14b, -C(=0)NR^14aR^14b, trimetilsililo, trietilsililo, tert-butildimethylsililo,

Cs-Cs-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or carry 1 or 2 radicals selected from cyano, C1-C4-alkyl, C3-C4-cycloalkyl, C1-C4-alkoxy, C1-

haloalkoxy C4 and oxo; Phenyl, benzyl, phenoxy, where the phenyl moiety in the last three mentioned radicals can be unsubstituted or have 1, 2, 3, 4 or 5 substituents R^sixteen; and a saturated, partially unsaturated or maximally unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocyclic ring with 1, 2, or 3 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as ring members , the heterocyclic ring is substituted with 1, 2 or 3 R substituents^sixteen;

dos R¹³are present on the same carbon atom of an alkyl, alkenyl, alkynyl, or cycloalkyl group together =0, =CH(Ci-C₄-Alquil), =C(Ci-C₄-Alquil)Ci-C₄-Rent, =NR¹⁷you = NO¹⁷; mi

R¹³is further selected as a substituent on a cycloalkyl ring from the group consisting of C1-C6 alkyl, C2-C6 alkenyl and C2-C6 alkynyl, where the last three aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may be 1 or carry 2 substituents selected from CN, C3-C₄-Cicloalquil, Ci-C₄-Alcóxi, Ci-C₄-haloalkoxi es oxo; b

R³en groups =C(R¹³)₂, -N=C(R¹³)₂, -C(=0)R¹³, -C(=S)R¹³mi

-C(=NR¹⁴)R¹³is further selected from the group consisting of hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl, where the last three aliphatic radicals are unsubstituted, partially or fully halogenated and/or may be 1 or 2 transport residues selected from CN, C3-C₄-Cicloalquil, Ci-C₄-Alcóxi, Ci-C₄-haloalkoxy and oxo; each R¹⁴is independently selected from the group consisting of hydrogen, cyano, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, d-Ce-alkylsulfonyl, d- Ce-haloalkylsulfonyl, -C(=O)NR^18aR^18b, trimetilsililo, trietilsililo, ferri-butildimethylsililo,

C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, where the last three aliphatic radicals may be unsubstituted, partially or fully halogenated and/or 1 or 2 radicals selected from CN, C1-C₄-Alcóxi, Ci-C₄-halogenalcoxi, C1-C₄-Alkyltio, Cy-C₄-Alquilsulfinilo, C1-C₄-Alkylsulfonyl, C3-C₄-cycloalkyl which may be substituted with 1 or 2 substituents selected from halogen and cyano; and oxo;

C3-C8 cycloalkyl which may be unsubstituted, partially or fully halogenated and/or carry 1 or 2 radicals selected from cyano, C1-C₄-Alquil, Ci-C₄-Alcóxi, Ci-C₄-halogenalcoxi, C1-C₄-Alkyltio, Cy-C₄-Alquilsulfinilo, C1-C₄-Alkylsulfonyl, C3-C₄-Cycloalquilo, C3-C₄-Cycloalquil- Ci-C₄-alkyl-, where the cycloalkyl part in the last two mentioned radicals can be replaced by 1 or 2 substituents selected from halogen and cyano; and oxo;

Phenyl, benzyl, pyridyl, phenoxy, where the cyclic moieties in the last four radicals may be unsubstituted and/or have 1, 2 or 3 substituents selected from halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6 - haloalkyl, C6 alkoxy, haloC1-C6alkoxy and (C1-C6alkoxy)carbonyl; and a saturated, partially unsaturated or maximally unsaturated 3-, 4-, 5- or 6-membered heterocyclic ring comprising 1 or 2 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO and SO2 as ring members, in which that the heterocyclic ring is optionally substituted with one or more R substituents^sixteen; R^14ay R. S.^14bindependently have one of the meanings given for R¹⁴; o

R^14ay R. S.^14bTogether with the nitrogen atom to which they are attached, they form a 3-, 4-, 5-, 6-, or 7-membered saturated, partially unsaturated, or maximally unsaturated heterocyclic ring, where the heterocyclic ring may additionally contain 1 or 2 heteroatoms or selected groups of heteroatoms. of N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally bears one or more substituents selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and haloalkoxy C1-C4;

R^14ay R. S.¹⁴o R^14by R. S.¹⁴together with the nitrogen atoms to which they are attached in the -C(=NR¹⁴)N(D^14a)R^14b, form a partially unsaturated or maximally unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocyclic ring, where the heterocyclic ring may additionally contain 1 or 2 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as ring members, wherein the heterocyclic ring optionally bears one or more substituents selected from halogen, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; each R^quinceis independently selected from the group consisting of hydrogen, cyano, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,

C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, where the last three aliphatic radicals may be unsubstituted, partially or fully halogenated and/or carry 1 or 2 radicals selected from C3-C4-cycloalkyl, C1 -C4-cycloalkyl, C4-alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl and oxo;

Phenyl, benzyl, pyridyl and phenoxy, where the last four radicals can be unsubstituted, partially or fully halogenated and/or have 1, 2 or 3 substituents selected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- alkoxy, C 1 -C 6 -haloalkoxy and (C 1 -C 6 -alkoxy)carbonyl; each R^sixteenis independently selected from the group consisting of halogen, nitro, cyano, -OH, -SH, d-Ce-alkoxy, Cy-Cy₆-halogenalcoxi, C1-C₆-Alkyltio, Cy-C₆- Halogenalquiltio, Ci-C₆- Alquilsulfinil, Ci-C6-Halogenalquilsulfinil, Ci-C6-Alquilsulfonil, Ci-C6-Halogenalquilsulfonil, Trimetilsilil, Trietilsilil, Ferri-Butyldimethylsilil;

C3-C8 cycloalkyl which may be unsubstituted, partially or fully halogenated and/or carry 1 or 2 radicals selected from C1-C4 alkyl, C3-C4 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and oxo; Phenyl, benzyl, pyridyl and phenoxy, where the last four mentioned radicals can be unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6 - alkoxy, haloC1-C6alkoxy and (C1-C6alkoxy)carbonyl; either

dos R^sixteenmay be present together on the same atom of an unsaturated or partially unsaturated ring =0, =S, =N(Ci-C₆-Alk), =NO(Ci-C₆-Alkyl), =CH(Ci-C₄-Alquil) or =C(Ci-C₄-Alquil)Ci-C₄-Rent;

dos R^sixteenon two adjacent carbon atoms they form, together with the carbon atoms to which they are attached, a 4-, 5-, 6-, 7-, or 8-membered saturated, partially unsaturated, or maximally unsaturated ring, which ring contains 1 or 2 heteroatoms or groups. of heteroatoms selected from N, O, S, NO, SO and SO 2 as ring members, and where the ring optionally bears one or more substituents selected from halogen, C1-C₄-Halogenalquilo, Ci-C₄-Alkoxy and Ci-C₄-haloalkyl;

R¹⁷, R^18ay R. S.^18b, independently and independently of each occurrence are selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, where the last three aliphatic radicals may be unsubstituted , partially or totally halogenated and/or 1 or 2 radicals selected from CN, Cy-C₄-Alcóxi, Ci-C₄- Halogenalkoxy, Ci-C₄-Alkyltio, Cy-C₄-Alquilsulfinilo, C1-C₄-Alkylsulfonyl, C3-C₄-cycloalkyl which may be substituted with 1 or 2 substituents selected from halogen and cyano; and oxo; C3-C8 cycloalkyl which may be unsubstituted, partially or fully halogenated and/or carry 1 or 2 radicals selected from cyano, C1-C₄-Rent and Ci-C₄-halogenalquila;

phenyl and benzyl; each n is independently 0, 1 or 2; Y

each m is independently 0 or 1;

and/or the stereoisomers, enantiomers, diastereomers and/or N-oxides, agricultural or veterinary acceptable salts thereof; and where the method is to control and/or prevent pest infestation of soybean plants and/or soybean crops.

In particular, the invention provides a method comprising applying a compound of formula I to soybean plants, soybean plants, soybean propagation material or loci thereof, wherein formula I wherein

A is a group A¹, AND²of uno³;

in what

AND¹is selected from the group consisting of -C(=NR⁶)R⁸, -S(0)_norteR⁹, eN(R⁵)R⁶;

AND²is a group of the following formula:

in what

# denotes the bond with the rest of the molecule;

W is selected from O and S;

AND³is a group of the following formula:

in what

# indicates attachment to the aromatic ring of formula (I);

R¹ausgewählt ist aus der Gruppe bestehend aus Ci-C4-Alkyl, Ci-C4-Halogenalquil, Ci-C4-Alcoxi-Ci-C4-Alquil, Ci-C4-Halogenalcoxi-Ci-C4-Alquil-, C2-C4-Alquenil, C2-C4-Haloalquenil, C2-C4-Alquinil, C2-C4-Haloalquinil, Cs-Ce-Cicloalquil, Cs-Ce-Halocicloalquil e -C(=0)OR^quince; every R²is independently selected from the group consisting of hydrogen, halogen, cyan, azido, nitro, -SCN, -SF₅, C1-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, where the last four aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or mono- or polysubstituted Radicals R⁸, -Herr¹²)₃, -O⁹, -S(0)_norteR⁹and not^{10 A}R^10b;

R^3a, R^3bare each independently selected from the group consisting of hydrogen,

Halogen, hydroxyl, -C0₂R^3d, CC₃-Rent, d-C₃-Halogenalquilo, C₂-C₃-Alkynyl, C2-C3-Alkynyl, C1-C₃-Alcóxi, Ci-C₃-halogenalcoxi, C1-C₃-Alkyltio, Cy-C₃-Halogenalquiltio, C1-C3-Alquilsulfonyl y Ci-C₃-haloalkylsulfonyl; you

R^3ay R. S.^3btogether they form a group =0, =C(R^3c)₂, =NO o =NO₃;

in what

every R^3cis independently selected from the group consisting of hydrogen, halogen, CH₃y FC₃; mi

R^3dis selected from the group consisting of hydrogen, C1-C6-alkyl and C1-C3-alkyloxy-C1-C₃-alkyl-; each R⁴is independently selected from the group consisting of hydrogen, halogen, cyan, azido, nitro, -SCN, -SF₅, C1-C6-alkyl, which may be partially or fully halogenated and/or substituted with one or more R radicals⁸, C₃-C8 cycloalkyl which may be partially or fully halogenated and/or substituted with one or more radicals R⁸, C2-C6-Alkenyl, which may be partially or fully halogenated and/or substituted with one or more R radicals⁸, C2-C6-Alkynyl, which may be partially or fully halogenated and/or substituted with one or more radicals R⁸,

-Herr¹²)₃, -O⁹, -S(0)_norteR⁹, -NR^{10 A}R^10b,

Cs-cycloalkyl, C2-Cylo-alkenyl, C2-Cylo-alkynyl, where the last four mentioned aliphatic and cycloaliphatic radicals may be partially or completely halogenated and/or substituted by one or more R substituents⁸, select from -X-R^6be-N(R^5a)R^6c; in what

X is selected from -C(R^and)₂-, -C(R^and)₂-C(R^and)₂-,

-C(R^and)₂-C(=O)-NO^0a-C(R^and)₂-, -C(R^and)₂-C(R^and)₂-C(=O)-NO^0a-C(R^and)₂-, -C(R^and)₂S(0)n-C(R^and)₂-, -C(R^and)₂-C(R^and)₂-S(0)n-C(R^and)₂-, -C(R^and)₂-0-C(R^and)₂-, mi

-C(R^and)₂-C(R^and)₂-0-C(R^and)₂-, in which

every R^andis independently selected from the group consisting of hydrogen, halogen, C1-C3 alkyl, and C1-C3 haloalkyl;

R^5aindependently has one of the meanings given for R⁵;

R^6bis selected from the group consisting of Cs-Cs-cycloalkyl, C₂-Cs-Alkenyl, C₂-C8-Alkynyl, the last three radicals mentioned being partially or totally halogenated and/or substituted by one or more substituents R⁸; mi

R^6cis selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, Cs-Cs cycloalkyl, Cs-Cs halocycloalkyl, C₂-C6-Alkenyl, C₂-C6-halogenalquenil, C₂-C6-Alkynyl, C₂-C6-Haloalkynyl, the aliphatic and cycloaliphatic parts in the last eight radicals mentioned being able to be substituted by one or more radicals R¹³;

-Ci-C₆-C-alkyl(=0)O^quince, -Ci-C₆-C-alkyl(=0)N (R^4a)R^4b, -Ci-C₆-Alquil-C(=S)N(R^4a)R^4b, -Ci-C₆-Alkyl-C(=NR)N(R^and)R, C1-C₆-Alkoxy, Ci-C6-Halogenalcoxi, Ci-C6-Alquilthio, Ci-C6-Halogenalquilthio,

-S(0)_norteR^quince, -S(0)_norteN(R^and)R , -C(=0)R¹³, -C(=0)O^quince, -C(=0)N(R^4a)R⁴, -C(=S)R¹³, -C(=S)SR^quince, -C(=S)N(R^4a)R⁴, and -C(=NO⁴)R¹³;

where in the case R⁵is hydrogen, R^6a1-cyanocyclopropyl, 1-cyanocyclobutyl and 1-cyanopentyl are also selected from hydrogen; either

R⁵y R. S.^6atogether they form a group =S(0)_metro(R⁹)₂; every R⁶is independently selected from the group consisting of hydrogen, cyano, C1-C10-alkyl, Cs-Cs-cycloalkyl, C₂-Cio-Alkenyl, C₂-Cylo-Alquinyl, where the last four aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or substituted by one or more R substituents⁸,

-O⁹, -NR^{10 A}R^10b, -S(0)_norteR⁹, -C(=O)NO^0aN(R^0a)R⁰), -Herr¹²)₃, -C(=0)R⁸, phenyl, which can be substituted with 1, 2, 3, 4 or 5 R substituents¹¹, and a saturated, partially unsaturated, or maximally unsaturated 3-, 4-, 5-, 6-, 7-, 8-, 9-, or 10-membered heteromonocyclic or heterobicyclic ring containing 1, 2, 3, or 4 independently selected heteroatoms or groups of heteroatoms of N, O, S, NO, SO and SO₂, as members of the ring, the heteromonocyclic or heterobicyclic ring being able to be substituted by one or more substituents R¹¹;

o R⁵y R. S.⁶o R⁵y R. S.^6aTogether with the nitrogen atom to which they are attached, they form a 3-, 4-, 5-, 6-, 7-, or 8-membered saturated, partially unsaturated, or maximally unsaturated heterocyclic ring, which ring may also contain 1, 2, 3, or 4 heteroatoms or groups containing heteroatoms selected from O, S, N, SO, SO2, C=0 and C=S as ring members, the heterocyclic ring being replaceable by 1,

2, 3, 4, or 5 substituents independently selected from the group consisting of halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy,

C1-C6-alkylthio, C1-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic or cycloaliphatic units in the last twelve radicals may be replaced by one or more R radicals⁸, and phenyl which can be substituted with 1, 2, 3, 4 or 5 R substituents¹¹;

R^7a, R^7bare each independently selected from the group consisting of hydrogen, halogen, cyano, C1-C6 alkyl, C5-C5 cycloalkyl, C2-C6 alkenyl, and C2-C6 alkynyl, the latter four being aliphatic and cycloaliphatic radicals can be partially or totally halogenated and/or substituted by one or more radicals R⁸; every R⁸is independently selected from the group consisting of cyano, azido, nitro, -SCN, -SF₅, Cs-Cs-Cycloalquil, Cs-Cs-Halocycloalquil, Cs-Cs-Cycloalquenyl, C₃-C₈- Halocycloalkenyl, the cycloaliphatic parts in the last four radicals mentioned being able to be substituted by one or more radicals R¹³;

-Herr¹²)₃, -O⁹, -OSO2R⁹, -S(0)_norteR⁹, -N(R^0a)R^0b, -C(=O)N(R^0a)R^0b,

-C(=S)N(R^0a)R^0b, -C(=0)O⁹,

Phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents^sixteen, mi

dos R⁸present on the same carbon atom of an alkyl, alkenyl, alkynyl, or cycloalkyl group together form a =0, =C(R¹³)₂; =S; =S(0)_metro(R^quince)₂, =S(0)_metroR^quinceN(R^4a)R⁴, =NR^0a, = NORTE⁹; o =NN(R^0a)R⁰;

R⁸en grupos -C(=NR⁶)R⁸e-C(=O)R⁸is further selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, and C2-C6 haloalkynyl, wherein the aliphatic portions in the last six radicals can be replaced by one or more radicals R¹³; every R⁹is independently selected from the group consisting of hydrogen, cyano, C1-Ce, C1-C alkyl₆-Halogenalquilo, C₃-C₈-Cicloalquil, C₃-C₈-Cycloalquil-Ci-C₄-Rent-, C₃-C₈- Halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, the aliphatic and cycloaliphatic parts in the last nine radicals being substituted by one or more radicals R¹³,

-Ci-C₆-C-alkyl(=0)O^quince, -Ci-C₆-Alkyl-C(=0)N(R^and) R ,

-Ci-C₆-Alquil-C(=S)N(R^4a)R^4b, -Ci-C₆-C-alkyl(=NR⁴)N(D^4a)R^4b,

-Herr¹²)₃, -S(0)_norteR^quince, -S(0)_norteN(R^and)R , -N(R^0a)R⁰, -N=C(R¹³)₂, -C(=0)R¹³,

-C(=0)N(R^4a)R⁴, -C(=S)N(R^4a)R⁴, -C(=0)O^quince,

Phenyl optionally substituted with one or more R substituents^sixteen; mi

a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1, 2 or 3 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO and SO 2 , as members ring, where the heterocyclic ring is optionally substituted with one or more R substituents^sixteen; mi

R⁹in groups -S(0)_norteR⁹e-OSO2R⁹is further selected from the group consisting of C1-C6 alkoxy and C1-C6 haloalkoxy; R.^{10 A}, R^10bindependently and independently of each occurrence are selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C₃-C₈- Cycloalquil, C₃-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the last eight radicals may be replaced by one or more R radicals¹³;

-Ci-C₆-C-alkyl(=0)O^quince, -Ci-C₆-Alkyl-C(=0)N(R^and)R, -Ci-C₆-rent-

C(=S)N(R^and)R, -Ci-C₆-Alkyl-C(=NR)N(R^and)R, C1-C₆-Alcóxi, Ci-C₆-Halogenalcoxi, d-Ce-Alkyltio, Ci-C₆-halogenalquiltio,

-S(0)_norteR^quince, -S(0)_norteN(R^and)R , -C(=0)R¹³, -C(=0)O^quince, -C(=0)N(R^and) R ,

-C(=S)R¹³, -C(=S)SR^quince, -C(=S)N(R^4a)R⁴, -C(=NR⁴)R¹³;

Phenyl optionally substituted with 1, 2, 3 or 4 R substituents^sixteen; mi

R^{10 A}y R. S.^10btogether with the nitrogen atom they form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the heterocyclic ring may additionally contain one or two heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally bears one or more substituents selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1- C6-alkylthio, C1-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with 1, 2, 3, 4 or 5 R substituents^sixteen, and a saturated, partially unsaturated or maximally unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocyclic ring comprising 1, 2, or 3 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as members of the ring, where the heterocyclic ring optionally bears one or more R substituents^sixteen;

o R^0ay R. S.^10btogether they form a group =C(R¹³)₂, =S(0)_metro(R^quince)₂,

=S(0)_metroR^quinceN(R^4a)R^4b, =NR¹⁴you = NO^quince; is independently selected from the group consisting of halogen, cyano, azido, nitro, -SCN, -SF₅, C1-C10-alkyl, Cs-C10-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, where the last four aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or substituted by one or more R radicals⁸,

-O⁹, -NR^{10 A}R^10b, -S(0)_norteR⁹, -Herr¹²)₃;

Phenyl optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from R^sixteen; mi

the dos R¹¹present on the same ring carbon atom of an unsaturated or partially unsaturated heterocyclic ring can together form a group =O, =S;

=S(0)_metro(R^quince)₂; =S(0)_metroR^quinceN(R^4a)R^4b, =NR¹⁴, = NORTE^quince, o =NN(R^4a)R⁴;

the dos R¹¹attached to adjacent ring atoms, together with the ring atoms to which they are attached, form a saturated 3-, 4-, 5-, 6-, 7-, 8-, or 9-membered ring, which ring may contain 1 or 2 heteroatoms or groups of heteroatoms selected from O, S, N, NR¹⁴, NO, SO y S0₂y/o 1 or 2 groups selected from C=O, C=S and C=NR¹⁴as members of the ring, and where the ring is substituted by one or more radicals selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1- C6-C6-alkylthio, C1-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, which can be replaced by 1, 2, 3, 4, or 5 residues R^sixteen, and a saturated, partially unsaturated or maximally unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocyclic ring containing 1, 2, or 3 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as members of the ring, the heterocyclic ring being able to be substituted by one or more radicals R^sixteen; every R¹²is independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C2-C6 haloalkenyl, and

Phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents^sixteen; every R¹³is independently selected from the group consisting of cyano, nitro,

-OH, -SH, -SCN, -SF₅, d-Ce-Alcóxi, Ci-C₆-halogenalcoxi, C1-C₆-Alkyltio, Cy-C₆- Halogenalquiltio, Ci-C6-Alquilsulfinil, Ci-C6-Halogenalquilsulfinil, Ci-C6-Alquilsulfonil, C1-C6-Halogenalquilsulfonil, -NR^14aR^14b, -C(=0)NR^14aR^14b, trimetilsililo, trietilsililo, tert-butildimethylsililo,

Cs-Cs cycloalkyl which may be unsubstituted, partially or fully halogenated and/or carry 1 or 2 radicals selected from cyano, C1-C4-alkyl, C3-C4-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and oxo; Phenyl, benzyl, phenoxy, the phenyl moiety in the last three mentioned radicals may be unsubstituted or have 1, 2, 3, 4 or 5 R substituents^sixteen; and a saturated, partially unsaturated or maximally unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocyclic ring containing 1, 2, or 3 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as members of the ring, where the heterocyclic ring can be replaced by 1, 2 or 3 R substituents^sixteen;

dos R¹³are present on the same carbon atom of an alkyl, alkenyl, alkynyl, or cycloalkyl group together =0, =CH(Ci-C₄-Alquil), =C(Ci-C₄-Alquil)Ci-C₄-Rent, =NR¹⁷you = NO¹⁷;

R¹³is further selected as a substituent on a cycloalkyl ring from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, and C2-C6-alkynyl, where the last three aliphatic radicals may be unsubstituted, partially or fully halogenated, and / or 1 or may have 2 substituents selected from CN, C3-C4 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and oxo;

R³en groups =C(R¹³)₂, -N=C(R¹³)₂, -C(=0)R¹³, -C(=S)R¹³mi

-C(=NR¹⁴)R¹³is further selected from the group consisting of hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl, where the last three aliphatic radicals are unsubstituted, partially or fully halogenated and/or they can be 1 or 2 transport radicals selected from CN, C3-C4-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and oxo; each R¹⁴is independently selected from the group consisting of hydrogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C6-haloalkylsulfonyl , -

C(=0)NR^18aR^18b, trimetilsililo, trietilsililo, fert-butildimethylsililo,

C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, where the last three aliphatic radicals can be unsubstituted, partially or totally halogenated and/or carry 1 or 2 radicals selected from CN, C1-C4-alkoxy , C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 3 -C 4 cycloalkyl, which may be substituted with 1 or 2 substituents selected from halogen and cyano ; and oxo;

C3-C8 cycloalkyl which may be unsubstituted, partially or fully halogenated and/or carry 1 or 2 radicals selected from cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-C1-C4-cycloalkyl-, where the cycloalkyl part in the last two radicals may be replaced by 1 or 2 substituents selected from between halogen and cyan; and oxo;

R^14ay R. S.^14bindependently have one of the meanings given for R¹⁴; o R^14ay R. S.^14bTogether with the nitrogen atom to which they are attached, they form a 3-, 4-, 5-, 6-, or 7-membered saturated, partially unsaturated, or maximally unsaturated heterocyclic ring, where the heterocyclic ring may additionally contain 1 or 2 heteroatoms or selected groups of heteroatoms. of N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally bears one or more substituents selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and haloalkoxy C1-C4; either

C3-C8 cycloalkyl which may be unsubstituted, partially or fully halogenated and/or carry 1 or 2 radicals selected from C1-C4 alkyl, C3-C4 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl and oxo; Phenyl, benzyl, pyridyl and phenoxy, where the last four radicals can be unsubstituted, partially or fully halogenated and/or have 1, 2 or 3 substituents selected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- alkoxy, haloC1-C6alkoxy and (C1-C6alkoxy)carbonyl; each R^sixteenis independently selected from the group consisting of halogen, nitro, cyano, -OH, -SH, d-Ce-alkoxy, Cy-Cy₆-halogenalcoxi, C1-C₆-Alkyltio, Cy-C₆- Halogenalquiltio, Ci-C₆- Alquilsulfinil, Ci-C6-Halogenalquilsulfinil, Ci-C6-Halogenalquilsulfonil, Ci-C6-Halogenalquilsulfonil, Trimetilsilil, Trietilsilil, Ferri-Butyldimethylsilil;

C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, where the last three aliphatic radicals may be unsubstituted, partially or fully halogenated and/or carry 1 or 2 radicals selected from C3-C4-cycloalkyl, C1 -C4-cycloalkyl, C4 alkoxy, C1-C4 haloalkoxy and oxo; C3-C8 cycloalkyl which can be unsubstituted, partially or totally halogenated and/or carry 1 or 2 radicals selected from C1-C4 alkyl, C3-C4 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and oxo;

Phenyl, benzyl, pyridyl and phenoxy, where the last four mentioned radicals can be unsubstituted, partially or totally halogenated and/or carry 1, 2 or 3 substituents selected from C1-C6-alkyl, C1-C6-haloalkyl, C1-C6 - alkoxy, haloC1-C6alkoxy and (C1-C6alkoxy)carbonyl;

dos R^sixteenon two adjacent carbon atoms form, together with the carbon atoms to which they are attached, a 4-, 5-, 6-, 7-, or 8-membered saturated, partially unsaturated, or maximally unsaturated ring, which ring contains 1 or 2 heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO and SO 2 as ring members, and where the ring optionally bears one or more substituents selected from halogen, haloC 1 -C 4 alkyl, C 1 -C 4 alkoxy and alkoxy C1-C4. haloalkoxy C4;

C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C4 cycloalkyl which may be substituted with 1 or 2 substituents selected from halogen and cyan; and oxo;

C3-C8 cycloalkyl which may be unsubstituted, partially or fully halogenated and/or contain 1 or 2 radicals selected from cyano, C1-C4 alkyl and C1-C4 haloalkyl; phenyl and benzyl; each n is independently 0, 1 or 2; and each m is independently 0 or 1; and/or the stereoisomers, enantiomers, diastereomers and/or N-oxides, agricultural or veterinary acceptable salts thereof; and where the method is to control and/or prevent pest infestation of soybean plants and/or soybean crops.

The compounds of formula (I) and their individual embodiments, defined below, used in the methods of the present invention may exist in various geometric or optical isomers or tautomeric forms. This invention encompasses all of these isomers and tautomers and their mixtures in all ratios as well as isotopic forms such as deuterated compounds. The compounds of the invention may contain one or more asymmetric carbon atoms and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures thereof.

In addition, reference to these compounds in the methods of the present invention also includes reference to their agricultural or veterinary salts and their N-oxides.

The compounds of the invention can be prepared according to the methods described in the patent application WO2013/092943 cited above.

The methods and uses of the invention are for controlling and/or preventing pest infestation of soybean plants, soybean crops, and soybean planting material. Preferably, the methods and uses of the present invention are used against pests of the Pentatomidae family, bedbugs. Particularly preferred against bed bugs resistant to other insecticides, e.g. Pyrethroid insecticides. Bed bugs that are "resistant" to a specific insecticide refer, for example, to strains of bed bugs that are less sensitive to that insecticide than the expected susceptibility of the same bed bug species. The expected sensitivity can e.g. a strain not previously exposed to the insecticide.

In the present invention, the terms Pentatomidae and bed bugs are used interchangeably.

In one aspect of the present invention, the method comprises applying a compound of formula I to soybean plants, soybean crops and/or soybean plant propagation material, which method is to control and/or prevent pest infestation.

In particular, the method serves to control and/or prevent infestation by pests of the Pentatomidae family, bed bugs.

The method preferably serves to control and/or prevent infestation by Acrosternum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha halys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria. in particular to control and/or prevent infestation by Acrosternum spp., Euschistus spp., Nezara spp. and/or Piezodrus spp., in particular by Acrosternum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini and more particularly by Euschistus heros and/or Nezara viridula. Especially by the heroes of Eusquists. Alternatively or additionally, the method serves in particular to control and/or prevent infestation by Halyomorpha halys.

In another aspect, the invention provides the use of a compound of formula I for the general control of pests of the family Pentatomidae, bed bugs.

The use is preferably to control Acrostemum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha halys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria, in particular to control Acrostemum spp., Euschistus spp. . .., Nezara spp. and/or Piezodrus spp., especially to control Acrostemum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini, more especially to control Euschistus heros and/or Nezara viridula, and especially to control Euschistus heroes. Alternatively or additionally, the use serves in particular to combat Halyomorpha halys.

In another aspect, the present invention provides the use of the compounds of formula I to control pests resistant to one or more insecticides, preferably pyrethroids, neonicotinoids and organophosphates and more preferably pyrethroid insecticides.

Preferably, the compounds of formula I are used to control pests of the family Pentatomidae, bed bugs, which are resistant to one or more insecticides, preferably pyrethroids, neonicotinoids and organophosphates and more preferably pyrethroid insecticides.

The compounds of formula I are preferably used for the control of Acrostemum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha halys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria, in particular for the control of Acrostemum spp. ., Euschistus spp., Nezara spp. are resistant, preferably pyrethroid, neonicotinoid and organophosphate and most preferably pyrethroid insecticides. Alternatively or additionally, the compounds of formula I are used to control Halyomorpha halys that is resistant to one or more other insecticides, preferably pyrethroid, neonicotinoid and organophosphate, and more preferably pyrethroid insecticides.

Like the term halogen, the organic radicals mentioned in the variable definitions above are collective terms for the individual listings of the individual members of the group. The prefix C_norte-C_metroindicates the possible number of carbon atoms in the group.

The term halogen means fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.

The term "alkyl" as used herein and alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl radicals and the like refers to 1 to 2 straight or branched chain saturated hydrocarbon radicals ("Ci-C₂-Alquil"), 1 bis 3 ("Ci-C₃-Alquil"), 1 bis 4 ("Ci-C₄-Alquil"), 1 bis 6 ("Ci-C₆-Alquil"), 1 bis 8 ("Ci-C₈-alkyl") or from 1 to 10 ("C1-C10 alkyl") carbon atoms. C1-C2 alkyl is methyl or ethyl. C1-C3 alkyl is also propyl and isopropyl.₄-Alkyl is also butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), or 1,1-dimethylethyl (tert-butyl). C1-C6 alkyl also represents, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl. C1-Cs alkyl also means, for example, heptyl, octyl, 2-ethylhexyl and their positional isomers. In addition, C1-C10 alkyl also represents, for example, nonyl, decyl and their positional isomers.

As used herein, the term "haloalkyl", also expressed as "partially or fully halogenated alkyl", refers to straight or branched chain alkyl groups having 1 to 2 ("C1-C2 haloalkyl").

1 and 3 ("Ci-C₃-Halogenalquil"), 1 a 4 ("Ci-C₄-Halogenalquil"), 1 a 6 ("Ci-C₆-Halogenalquil"), 1 a 8 ("Ci-C₈- Haloalkyl") or from 1 to 10 ("C1-Cio-haloalkyl") carbon atoms (as mentioned above), the hydrogen atoms in these groups being fully or partially replaced by halogen atoms as mentioned above: in particular C1-C2 -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl B 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl, C1-C3 -haloalkyl is also, for example, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3- trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl,

3-chloropropyl and the like. Ci–C Examples₄-Haloalkyl are, in addition to those mentioned for C1-C3-haloalkyl, 4-chlorobutyl and the like.

"Halomethyl" is methyl with 1, 2 or 3 of the hydrogen atoms replaced by halogen atoms. Examples are bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.

The term "alkenyl", as used herein, refers to 2 to 3 chain linear or branched monounsaturated hydrocarbon radicals ("C₂-C₃-Alquenilos"), 2 bis 4 ("C₂-C₄-Alquenilos"), 2 bis 6 ("C₂-C₆-Alkenyl"),

2 to 8 ("C2-C8-alkenyl") or 2 to 10 ("C2-Cio-alkenyl") carbon atoms and a double bond at any position, e.g. C2-C3-alkenyl, such as ethenyl, 1-propenyl , 2-propenyl or 1-methylethenyl; C2-C₄-Alquenyl, como Ethenyl, 1-Propenyl, 2-Propenyl, 1-Methyltenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1-Methyl-1-propenyl, 2-Methyl-1-propenyl, 1-Methyl - 2-propenyl o 2-methyl-2-propenyl; C2-C6-Alquenyl, como Ethenyl, 1-Propenyl, 2-Propenyl, 1-Methyltenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1-Methyl-1-propenyl, 2-Methyl-1-propenyl, 1 -Methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl -1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3 -butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1 -hexenyl, 2-hexenyl, 3-hexenyl,

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4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,

4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2- Methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl- 4-pentenyl,

1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,

1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,

3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1- butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl- 1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like, or C2-Cio-alkenyl, as the radicals mentioned for C2-C6-alkenyl and additionally 1-heptenyl, 2-heptenyl, 3-heptenyl, 1 -octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 1-nonenyl, 2-nonenyl, 3-nonenyl, 4-nonenyl, 1-decenyl, 2-decenyl, 3-decenyl, 4-decenyl, 5-decenyl and its positional isomers.

As used herein, the term "haloalkenyl", also expressed as "partially or fully halogenated alkenyl", refers to 2- to 4-chain linear or branched unsaturated hydrocarbon radicals ("C₂-C₄-haloalkenilo"), 2 to 6 ("C₂-C₆-haloalkenilo"), 2 to 8 ("C₂-C₆-haloalkenyl") or from 2 to 10 carbon atoms ("C2-Ciohaloalkenyl") and a double bond in any position (as mentioned above), some or all of the hydrogen atoms in these groups being replaced by halogen atoms such as mentioned above, especially fluorine, chlorine and bromine, for example, chlorovinyl, chlorallyl and the like.

As used herein, the term "alkynyl" refers to 2 to 3 straight or branched chain hydrocarbon groups ("C₂-C₃-Alkynyl"), 2 bis 4 ("C₂-C₄-Alkynyl"), 2 bis 6 ("C₂-C₆-alkynyl"), 2 bis 8 ("C₂-C₈- alkynyl") or from 2 to 10 ("C₂-Cio-Alkynyl") carbon atoms and one or two triple bonds in any position, for example, C₂-C3-Alkynyl, such as Ethynyl, 1-Propynyl or 2-Propynyl; C₂-C₄- alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like, C₂-C6-Alquinilo, como Ethynilo, 1-Propinilo, 2-Propinilo, 1-Butinilo, 2-Butinilo, 3-Butinilo, 1-Methyl-2-propinilo, 1-Pentinilo, 2-Pentinilo, 3-Pentinilo, 4 - pentinyl, 1 -methyl-2-butynyl, 1 -methyl-

3-butinilo, 2-methyl-3-butinilo, 3-methyl-1-butinilo, 1,1-dimethyl-2-propinilo, 1-ethyl-2-propinilo, 1-hexinilo, 2-hexinilo, 3-hexinilo, 4-hexinilo, 5-hexinilo, 1-methyl-2-pentinilo, 1-methyl-3-pentinilo, 1-methyl-4-pentinilo, 2-methyl-3-pentinilo, 2-methyl-4-pentinilo, 3- Methyl-1-pentinilo, 3-methyl-4-pentinilo, 4-methyl-1-pentinilo, 4-methyl-2-pentinilo, 1,1-dimethyl-2-butinilo, 1,1-dimethyl-3-butinilo, 1,2-Dimethyl-3-butinilo, 2,2-Dimethyl-3-butinilo, 3,3-Dimethyl-1-butinilo, 1-Ethyl-2-butinilo, 1-Ethyl-3-butinilo, 2-Ethyl- 3-butinilo, 1-ethyl-1-methyl-2-propinilo y derglieno;

As used herein, the term "haloalkynyl", also expressed as "partially or fully halogenated alkynyl", refers to 2 to 4 straight or branched chain unsaturated hydrocarbon radicals ("C₂-C₄-haloalquinyl"), 3 to 4 ("C₃-C₄-haloalquinyl"), 2 to 6 ("C₂-C₆-haloalquinyl"), 2 to 8 ("C₂-C8-haloalquinyl") of de 2 to 10 ("C₂-Ciohaloalkynyl")-carbon atoms and one or two triple bonds in any position (as mentioned above), the hydrogen atoms in these groups are replaced in whole or in part by halogen atoms as mentioned above, in particular fluorine, chlorine and bromo.cycloalkyl" include examples of monocyclic radicals having 3 to 6 carbon atoms cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl Examples of monocyclic radicals having 3 to 8 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl or 8 carbon atoms include bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl Preferably, the term "cycloalkyl" denotes a saturated monocyclic hydrocarbyl. The term "halocycloalkyl", as u Herein, which is also expressed as "cycloalkyl that is partially or fully halogenated", refers to hydrocarbon groups mono-, bi- or polycyclic saturated 3 to 8 ("Cs-Cs-halocycloalkyl") or preferably 3 to 6 ("C3-C6-halocycloalkyl") carbon ring members (as mentioned above) in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.

The term "cycloalkenyl", as used herein, refers to monocyclic hydrocarbon radicals having at least one C-C double bond in the ring, but when the ring is non-aromatic, hydrocarbon radicals having 3 to 8 carbon atoms. carbon ("Cs-Cs cycloalkyl)". Examples are cyclopropenyl such as cycloprop-1-enyl and cycloprop-2-yl, cyclobutenyl such as cyclobut-1-enyl and cyclobut-2-enyl, cyclopentenyl such as cyclopent-1-enyl, cyclopent-2-enyl and cyclopent-3-enyl , cyclopentadienyl such as cyclopenta-1,3-dienyl, cyclopenta-1,4-dienyl and cyclopenta-2,4-dienyl, cyclohexenyl such as cyclohex-1-enyl, cyclohex-2-enyl and cyclohex-3-enyl, cyclohexadienyl such as cyclohexa-1,3-dienyl, cyclohexa-1,4-dienyl, cyclohexa-1,5-dienyl and cyclohexa-2,5-dienyl, cycloheptenyl, cycloheptadienyl, cycloheptatrienyl, cyclooctenyl, cyclooctadienyl, cyclooctatrienyl and cyclooctatetraenyl.

The term "halocycloalkenyl", as used herein, refers to monocyclic hydrocarbon radicals having at least one C-Cs double bond in the ring that is not aromatic, hydrocarbon radicals having from 3 to 8 carbon atoms (" Cs-Cs-halocycloalkyl"). and where some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, especially fluorine, chlorine and bromine.

The term "cycloalkyl-C1-C4-alkyl" denotes a Cs-Cs-cycloalkyl ("C3-Cs-cycloalkyl-C1-C4-alkyl") group, preferably a C3-C6-cycloalkyl ("C3-C6-alkyl "). Cycloalkyl-C1-C4-alkyl"), particularly preferably a C3-C4-cycloalkyl group ("C3-C4-cycloalkyl-C1-C4-alkyl") as defined above (preferably a monocyclic cycloalkyl group), which is attached to the radical des Molecule through a C1-C4 alkyl group as defined above C4 alkyl, in addition to those mentioned for C3-C4 cycloalkyl-C1-C4 alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl. of C3-C6 cycloalkyl-C1-C4 alkyl named cycloheptylmethyl, cycloheptylethyl, cyclooctylmethyl, etc. having a C1-C4 alkyl group as defined above attached to the remainder of the molecule.The term "C1-C2 alkoxy" represents a C1-C2 alkyl group bonded through an oxygen atom as defined above. The term "C1-C3 alkoxy" represents a C1-C3 alkyl group bonded through an oxygen atom as defined above. C1-C4" rep it has a C1-C4 alkyl group attached through an oxygen atom as defined above. The term "C1-C6 alkoxy" represents a C1-C6 alkyl group attached through an oxygen atom as defined above. The term "C1-C10 alkoxy" is a C1-C10 alkyl group as defined above attached through an oxygen atom. C1-C2 alkoxy is methoxy or ethoxy. C1-C3 alkoxy is also, for example, n-propoxy and 1-methylethoxy (isopropoxy). C1-C4 alkoxy is also, for example, butoxy,

1-methylpropoxy (sec.-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylpropoxy (tert.-butoxy). Ci-C6-Alkoxy is also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy B. 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy. Ci-Cs-Alkoxy is also, for example, heptyloxy, octyloxy, 2-ethylhexyloxy, and positional isomers thereof. C1-C10 alkoxy is also, for example, nonyloxy, decyloxy and positional isomers thereof.

The term "C1-C2 haloalkoxy" is a C1-C2 haloalkyl group, as defined above, attached through an oxygen atom. The term "C1-C3 haloalkoxy" is a C1-C3 haloalkyl group as defined above attached through an oxygen atom. The term "C1-C4 haloalkoxy" is a C1-C4 haloalkyl group as defined above attached through an oxygen atom. The term "C1-C6 haloalkoxy" is a C1-C6 haloalkyl group as defined above attached through an oxygen atom. The term "C1-Ciohaloalkoxy" is a C1-Ciohaloalkyl group as defined above attached through an oxygen atom. Haloalkoxy C 1 -C 2 is, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH 2 Cl, OCHC, OCCl 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2- iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy or OC2F5. HaloC1-C3alkoxy is also, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,

2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -(CH₂F) -2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy or 1-(CH2Br)-2-bromoethoxy. C1-C4 haloalkoxy is also, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. C1-C6 haloalkoxy is also, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

The term "C1-C4 alkoxy-C1-C4 alkyl" as used herein refers to a straight or branched chain alkyl group having 1 to 4 carbon atoms as defined above, wherein a hydrogen atom is replaced by a C1 - C4 alkoxy group, as defined above. The term "C1-C6 alkoxy-C1-C6 alkyl" as used herein refers to a straight or branched chain alkyl group having 1 to 6 carbon atoms as defined above, wherein a hydrogen atom is substituted with a C1-C6 atom. alkoxy group as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 1-n-butoxyethyl, 1-sec - butoxyethyl, 1-isobutoxyethyl, 1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl , 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl, 1-n-butoxypropyl, 1-sec-butoxypropyl, 1-isobutoxypropyl, 1-tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl , 2-isopropoxypropyl, 2-n-butoxypropyl, 2-sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3 - sec-butoxypropyl, 3-isobutoxypropyl, 3-tert-butoxypropyl and the like.

The term "C1-C6 alkoxymethyl", as used herein, refers to methyl in which a hydrogen atom is replaced by a C1-C6 alkoxy group as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, pentyloxymethyl, hexyloxymethyl and the like.

C1-C6-haloalkoxy-C1-C6-alkyl is a straight or branched chain alkyl group having 1 to 6, in particular 1 to 4, carbon atoms (=C1-C6-haloalkoxy-C1-C4-alkyl ), where one of the hydrogen atoms is replaced by a C1-C6 alkoxy group and at least one, for example 1, 2, 3, 4 or all of the remaining hydrogen atoms (in the alkoxy part or the alkyl part or both ) are replaced by halogen atoms. C1-C4-haloalkoxy-C1-C4-alkyl is a straight or branched chain alkyl group with 1 to 4 carbon atoms, one of the hydrogen atoms is replaced by a C1-C₄-alkoxy group and in which at least one, for example 1, 2, 3, 4 or all of the remaining hydrogen atoms (in the alkoxy part or in the alkyl part or both) are replaced by halogen atoms. Examples are difluoromethoxymethyl (CHF2OCH2), trifluoromethoxymethyl, 1-difluoromethoxyethyl, 1-trifluoromethoxyethyl, 2-difluoromethoxyethyl, 2-trifluoromethoxyethyl, difluoromethoxymethyl (CH3OCF2), 1,1-difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like.

The term "C1-C2 alkylthio" is a C1-C2 alkyl group as defined above attached through a sulfur atom. The term "C1-C3 alkylthio" is a C1-C3 alkyl group as defined above attached through a sulfur atom. The term "Ci-C₄-alkylthio" is a Cy-C₄-alkyl group as defined above attached through a sulfur atom. The term "C1-C6 alkylthio" is a C1-C6 alkyl group as defined above attached through a sulfur atom. The term "C1-C10 alkylthio" is a C1-C10 alkyl group as defined above attached through a sulfur atom. C1-C2-alkylthio is methylthio or ethylthio. C1-C3 alkylthio is also, for example, n-propylthio or 1-methylethylthio (isopropylthio). Ci-C₄-alkylthio is also, for example, butylthio,

1-methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1,1-dimethylethylthio (tert-butylthio). C1-C6 alkylthio is also, for example, pentylthio, 1-methylbutylthio,

2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,

2,2-Dimethylpropylthio, 1-Ethylpropylthio, Hexylthio, 1-Methylpentylthio, 2-Methylpentylthio,

3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,

1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio. C 1 -C s alkylthio is also, for example, heptylthio, octylthio, 2-ethylhexylthio and their positional isomers. Ci-Cio-alkylthio is also, for example, nonylthio, decylthio and their positional isomers.

The term "C1-C2 haloalkylthio" is a C1-C2 haloalkyl group as defined above attached through a sulfur atom. The term "C1-C3 haloalkylthio" is a C1-C3 haloalkyl group as defined above attached through a sulfur atom. The term "C1-C4 haloalkylthio" is a C1-C4 haloalkyl group, as defined above, attached through a sulfur atom. The term "C1-C6 haloalkylthio" is a C1-C6 haloalkyl group as defined above attached through a sulfur atom. The term "C1-Ciohaloalkylthio" is a C1-Ciohaloalkylthio group as defined above attached through a sulfur atom. Examples of C1-C2 haloalkylthio are SCH2F, SCHF2, SCF3, SCH2Cl, SCHC, SCCI, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2 ,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or SC2F5. Furthermore, d-Cs-haloalkylthio is, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH2-C2F5, SCF2-C2F5, 1-(CH₂F)-2-fluoretiltio, 1-(CH₂Cl)-2-cloroetiltio o 1-(CH₂Br)-2-bromoethylthio. C 1 -C 4 haloalkylthio is also, for example, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. HaloC 1 -C 6 alkylthio is also, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6- iodohexylthio or dodecafluorohexylthio.

The term "C 1 -C 2 -α I ky Is u If inyl" is a C 1 -C 2 alkyl group as defined above attached through a sulfinyl group [S(O)]. The term "C1-C4 alkylsulfinyl" is a C1-C4 alkyl group as defined above attached through a sulfinyl-[S(O)]- group. The term "C1-C6-alkylsulfinyl" is a C1-C6 alkyl group as defined above attached through a sulfinyl group [S(O)]. The term "C1-C10 alkylsulfinyl" is a C1-C10 alkyl group as defined above attached through a sulfinyl group [S(O)]. C1 -C2 -alkylsulfinyl is methylsulfinyl or ethylsulfinyl. C1-C4 alkylsulfinyl is also, for example, n-propylsulfinyl, 1-methylethylsulfinyl (isopropylsulfinyl), butylsulfinyl, 1-methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or 1,1-dimethylethylsulfinyl (tert-butylsulfinyl). C1-C6 alkylsulfinyl is also, for example, pentylsulfinyl, 1-methylbutylsulfinyl,

2-Methylbutylsulfinyl, 3-Methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-methylpentylsulfinyl B 1,2,2-Trimethylpropylsulfinyl, 1-Ethyl-1-methylpropylsulfinyl or 1-Ethyl-2-methylpropylsulfinyl. C-i-Cs-Alkylsulfinyl is also, for example, heptylsulfinyl, octylsulfinyl, 2-ethylhexylsulfinyl and their positional isomers. Ci-Cio-alkylsulfinyl is also, for example, nonylsulfinyl, decylsulfinyl and their positional isomers.

The term "C1-C2 haloalkylsulfinyl" is a C1-C2 haloalkyl group as defined above attached through a sulfinyl group [S(O)]. The term "C1-C4 haloalkylsulfinyl" is a C1-C4 haloalkyl group as defined above attached through a sulfinyl group [S(O)]. The term "C1-C6 haloalkylsulfinyl" is a C1-C6 haloalkyl group as defined above attached through a sulfinyl group [S(O)]. The term "C1-C10 haloalkylsulfinyl" is a C1-C10 haloalkyl group as defined above attached through a sulfinyl group [S(O)]. Ci-C₂-Haloalkylsulfinyl is, for example, S(O)CH₂F, S(0)CHF₂, S(0)CF₃, S(0)CH₂CI, S(0)WANTS₂, S(0)CCl3, Clorfluormetilsulfinil, Diclorfluormetilsulfinil, Clordifluormetilsulfinil, 2-Fluoretilsulfinil, 2-Cloroetilsulfinil, 2-Brometilsulfinil, 2-Iodetilsulfinil,

2.2- Difluoretilsulfinil, 2 , 2 ,2-trif I uoroethy I su If en 1 , 2-Cloro-2-fluoretilsulfinil, 2-Cloro-2,2-difluoroetilsulfinil, 2,2-Dicloro-2-fluoretilsulfinil, 2, 2 ,2-tricloroetilsulfinilo o S(0)C₂F₅. Ci-C4-haloalquilsulfinil también, por ejemplo, 2-fluoropropilsulfinil, 3-fluoropropilsulfinil, 2,2-difluoropropilsulfinil, 2,3-difluoropropilsulfinil, 2-cloropropilsulfinil, 3-cloropropilsulfinil,

2,3-dichloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, S(0)CH₂-C₂F₅, S(0)CF₂-C₂F₅, 1-(CH₂F)-2-Fluoretilsulfinil, 1-(CH₂Cl)-2-cloroetilsulfinilo, 1 -(CH₂Br)-2-bromomethylsulfinyl,

4-fluorobutilsulfinil, 4-clorobutilsulfinil, 4-bromobutilsulfinil o nonafluorobutilsulfinil. C1-C6 haloalquilsulfinil também é, por ejemplo, 5-fluoropentilsulfinil, 5-cloropentilsulfinil, 5-bromopentilsulfinil, 5-iodopentilsulfinil, undecafluoropentilsulfinil, 6-fluorohexilsulfinil, 6-clorohexilsulfinil, 6-bromohexilsulfinil, 6-iodohexilsulfinil ou dodeilcafluorohexilsulfin.

Or thermo "Ci-C₂-alkylsulfonyl" is a C1-C₂-alkyl group as defined above attached through a sulfonyl group [S(0)₂] Group. The term "C1-C3 alkylsulfonyl" is a C1-C3 alkyl group as defined above attached through a sulfonyl group [S(0)₂] Group. The term "C1-C4 alkylsulfonyl" is a C1-C4 alkyl group as defined above attached through a sulfonyl group [S(0)₂] Group. The term "C1-C6 alkylsulfonyl" is a C1-C6 alkyl group as defined above attached through a sulfonyl group [S(0)₂] Group. The term "C1-C10 alkylsulfonyl" is a C1-C10 alkyl group as defined above attached through a sulfonyl group [S(0)₂] group. Ci-C₂-Alquilsulfonyl é Methylsulfonyl o Ethylsulfonyl. Alquilsulfonilo C1-C3 es también, por ejemplo, n-propylsulfonilo or 1-methylethylsulfonilo (isopropylsulfonilo). Ci-C4-Alquilsulfonil es también por ejemplo Butilsulfonil, 1-Methylpropilsulfonil (sek.-Butilsulfonil), 2-Methylpropilsulfonil (iso-Butilsulfonil) o 1,1-Dimethyletilsulfonil (tert.-Butilsulfonil). Ci-C6-Alquilsulfonil é ausgeierung beschreibung Pentilsulfonil, 1 -Metilbutilsulfonil, 2-Metilbutilsulfonil, 3-Metilbutilsulfonil, 1 ,1 - Dimetilpropilsulfonil, 1 ,2-Dimetilpropilsulfonil, 2,2-Dimethylpropylsulfonil, 1 - Ethylpropylsulfonil, Hexylsulfonil, 1 -Methylpentilsulfonil 2 -methylpentylsulfonyl,

3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2- ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl. Examples of α-Cs-alkylsulfonyl are also heptylsulfonyl, octylsulfonyl, 2-ethylhexylsulfonyl and their positional isomers. C1-C10 alkylsulfonyl is also, for example, nonylsulfonyl, decylsulfonyl and their positional isomers. The term "C1-C2 haloalkylsulfonyl" is a C1-C2 haloalkyl group as defined above attached through a [S(O)2] sulfonyl group. The term "C1-C3 haloalkylsulfonyl" is a C1-C3 haloalkyl group as defined above attached through a [S(O)2] sulfonyl group. The term "C1-C4 haloalkylsulfonyl" is a C1-C4 haloalkyl group as defined above attached through a [S(O)2] sulfonyl group. The term "C1-C6 haloalkylsulfonyl" is a C1-C6 haloalkyl group as defined above attached through a [S(O)2] sulfonyl group. The term "C1-Ciohaloalkylsulfonyl" is a C1-Ciohaloalkylsulfonyl group as defined above attached through a [S(O)2] sulfonyl group. HaloC1-C2alkylsulfonyl is, for example, S(0)2CH2F, S(0)₂Swiss francs₂, S(0)₂FC₃, S(0)₂CH₂KI, S(0)₂I WILL GO₂, S(0)₂IHK₃,2-Difluoroethylsulfonyl, 2,2-Dichloro-2-fluoroethylsulfonyl, 2,2,2-Trichloroethylsulfonyl o S(0)2C2F₅. Ci-C3-Halogenalquilsulfonil é austeiner por ejemplo 2-Fluorpropylsulfonil, 3-Fluorpropylsulfonil, 2,2-Difluoropropylsulfonil, 2,3-Difluoropropylsulfonil, 2-Cloropropylsulfonil, 3-Chloropropylsulfonil, 2,3-Dichloropropylsulfonil, 2-Bromopropylsulfonil ,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, S(0)₂CH2-C2F₅, S(0)2CF2-C₂F₅, 1-(CH₂F) -2-fluoroethylsulfonyl, 1-(CH2Cl)-2-chloroethylsulfonyl or 1-(CH2Br)-2-bromoethylsulfonyl. Haloalkylsulfonyl C _{1} - C _{4} is also, for example, 4 - fluorobutylsulfonyl, 4 - chlorobutylsulfonyl, 4 - bromobutylsulfonyl or N - nafluorobutylsulfonyl. Haloalkylsulfonyl C1-C6 is also, for example, 5-fluoropentylsulfonyl,

5-clorpentilsulfonil, 5-brompentilsulfonil, 5-iodpentilsulfonil, undecafluorpentilsulfonil,

6-fluorohexylsulfonyl, 6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl. The "oxo" substituent replaces a CH2 group with a C(=0) group.

The term "alkylcarbonyl" is a C1-C₆-Alquil ("Ci-C₆-alkylcarbonyl"), preferably a C1-C₄-alkyl group ("C1-C4-alkylcarbonyl") as defined above attached through a carbonyl group [C(=O)]. Examples are acetyl(methylcarbonyl), propionyl(ethylcarbonyl), propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl and the like.

The term "haloalkylcarbonyl" is a C1-C6 haloalkyl group ("C1-C6 haloalkylcarbonyl"), preferably a C1-C4 haloalkyl group ("C1-C4 haloalkylcarbonyl") as defined above linked through a carbonyl

group [C(=0)]. Examples are trifluoromethylcarbonyl, 2,2,2-trifluoroethylcarbonyl and the like.

The term "alkoxycarbonyl" is a C1-C6 alkoxy ("C1-C6 alkoxycarbonyl"), preferably a C1-C4 alkoxy ("C1-C4 alkoxycarbonyl") group as defined above attached via a [C(=0) carbonyl group ] . Examples are methoxycarbonyl), ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl and the like.

The term "haloalkoxycarbonyl" is a C1-C6 haloalkoxy group ("C1-C6 haloalkoxycarbonyl"), preferably a C1-C4 haloalkoxy group ("C1-C4 haloalkoxycarbonyl") as defined above joined through a [C (= 0)] . Examples are trifluoromethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl and the like.

The term "C1-C6-alkylamino" is a group -N(H)C1-C6-alkyl. Examples are methylamino, ethylamino, propylamino, isopropylamino, butylamino and the like.

The term "di-(Ci-C6-alkyl)amino" is a -N(Ci-C6-alkyl)2 group. Examples are dimethylamino, diethylamino, ethylmethylamino, dipropylamine, diisopropylamine, methylpropylamine, methylisopropylamine, ethylpropylamine, ethylisopropylamine, dibutylamino and the like.

The term "3-, 4-, 5-, 6-, 7-, 8-, 9-, or 10-membered saturated, partially unsaturated, or maximally unsaturated heterocyclic ring containing 1, 2, or 3 (or 4) heteroatoms or groups of heteroatoms contains selected from N, O, S, NO, SO and SO2, "ring members" denotes a saturated, partially unsaturated or maximally unsaturated 3, 4, 5, 6 or 7 membered heteromonocyclic ring or an 8, 9 ring or 10 membered saturated heterobicyclic ring, partially unsaturated or maximally unsaturated having 1, 2, or 3 (or 4) heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as ring members

Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond. Maximally unsaturated rings contain as many C-C and/or C-N and/or N-N conjugated double bonds as the size of the ring allows. Maximally unsaturated 5- or 6-membered heterocyclic rings are aromatic. The heterocyclic ring can be connected to the rest of the molecule through a carbon or nitrogen ring. Obviously, the heterocyclic ring contains at least one ring carbon atom. If the ring contains more than one O-ring atom, they are not adjacent.

The term "saturated, partially unsaturated, or maximally unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocyclic ring containing 1, 2, or 3 (or 4) heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO and SO2, as ring members" [where "maximally unsaturated" also includes "aromatic"], as used herein, denotes monocyclic radicals, where monocyclic radicals are saturated, partially unsaturated, or maximally unsaturated (including aromatics). . The term "3-, 4-, 5-, 6-, 7-, or 8-membered saturated, partially unsaturated, or maximally unsaturated heterocyclic ring containing 1, 2, or 3 (or 4) heteroatoms or groups of heteroatoms selected from N, O, S, NO , SO and SO 2 as ring members" [where "maximally unsaturated" also includes "aromatic"] as used herein also includes 8-membered heteromonocyclic radicals containing 1, 2 or 3 (or 4) heteroatoms or groups of heteroatoms selected from N, E, S, NE, SO, and SO2, as ring members, where the monocyclic radicals are saturated, partially unsaturated, or maximally unsaturated (including aromatics). Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond. Maximally unsaturated rings contain as many C-C and/or C-N and/or N-N conjugated double bonds as the size of the ring allows. Maximally unsaturated 5- or 6-membered heterocyclic rings are aromatic. The 7 and 8 membered rings cannot be aromatic. They are either homoaromatic (7-membered ring, 3 double bonds) or have 4 double bonds (8-membered ring). The heterocyclic ring can be connected to the rest of the molecule through a carbon or nitrogen ring. Obviously, the heterocyclic ring contains at least one ring carbon atom. If the ring contains more than one O-ring atom, they are not adjacent.

Beispiele für einen 3-, 4-, 5-, 6- oder 7-gliedrigen gesättigten heterocyclischen Ring ompassen: Oxiranyl, Thiiranyl, Aziridinyl, Oxetanyl, Thietanyl, Azetidinyl, Tetrahydrofuran-2-yl, Tetrahydrofuran-3-yl, Tetrahy - Drothien -2-yl, Tetraidrotien-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5 -yl, imidazolidin-1-yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl , Isoxazolidin-3-yl, Isoxazolidin-4-yl, Isoxazolidin-5-yl, Thiazolidin-2-yl, Thiazolidin-3-yl, Thiazolidin-4-yl, Thiazolidin-5-yl, Isothiazolidin-2-yl, Isothiazolidine -3-yl, Isothiazolidin-4-yl, Isothiazolidin-5-yl, 1,2,4-Oxadiazolidin-3-yl, 1,2,4-Oxadiazolidin-5-yl, 1,2,4-Thiadiazolidin-3 -yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl , 1,3,4-triazolidin-1-yl, 1,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydro Pira cero, 1,3-dioxano-5-yl, 1,4-dioxano-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, hexahidropiridazin-3 - il, Hexa-hidropyrimidin-4-il, Hexa-hidropyrimidin-2-il, Hexa-hidropyrimidin-4-il, Hexa-hidropyrimidin-5-il, Piperazin-1-il, Piperazin-2-il, 1,3, 5-Hexa-hidrotriazin-1-yl, 1,3,5-Hexahidrotriazin-2-yl e

1,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1 - Oxotiomorpholin-2-ilo, 1-oxotiomorpholin-3-ilo, 1-oxotiomorpholin-4-ilo, 1,1-dioxotiomorpholin-2-ilo, 1,1-dioxotiomorpholin-3-ilo, 1,1-dioxotiomorpholin-4- il, Azepan-1-, -2-, -3- ou -4-il, Oxepan-2-, -3-, -4- ou -5-il, Hexahidro-1,3-diazepinil, Hexahidro-1, 4-diazepinil, hexahidro-1,3-oxazepinil, hexahidro-1,4-oxazepinil, hexahidro-1,3-dioxepinil, hexahidro-1,4-dioxepinil y dergleichen.

Examples of a 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic ring include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2 -yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl,

2,3-diidrotien-3-il, 2,4-diidrotien-2-il, 2,4-diidrotien-3-il, 2-pyrrolina-2-il, 2-pyrrolina-3-il,

3-Pirrolin-2-il, 3-Pirrolin-3-il, 2-Isoxazolin-3-il, 3-Isoxazolin-3-il, 4-Isoxazolin-3-il, 2-Isoxazolin-

4-ilo, 3-isoxazolin-4-ilo, 4-isoxazolin-4-ilo, 2-isoxazolin-5-ilo, 3-isoxazolin-5-ilo, 4-isoxazolin-5-ilo, 2-isothiazolin-3- 1, 3-isothiazolin-3-ilo, 4-isothiazolin-3-ilo, 2-isothiazolin-4-ilo, 3-isothiazolin-4-ilo, 4-isothiazolin-4-ilo, 2-isothiazolin-5-ilo, 3-Isothiazolin-5-yl, 4-Isothiazolin-5-yl, 2,3-Di-hidropyrazol-1-yl, 2,3-Di-hidropyrazol-2-yl, 2,3-Di-hidropyrazol-3- 1,2,3-Di-hidropyrazol-4-1,2,3-Di-hidropyrazol-

5-ilo, 3,4-Di-hydropyrazol-1-ilo, 3,4-Di-hydropyrazol-3-ilo, 3,4-Di-hydropyrazol-4-ilo,

3,4-di-hidropirazol-5-ilo, 4,5-di-hidropirazol-1-ilo, 4,5-di-hidropirazol-3-ilo, 4,5-di-hidropirazol-4-ilo, 4, 5-Di-hidropirazol-5-il, 2, 3-Dihidrooxazol-2-il, 2,3-Dihidrooxazol-3-il, 2,3-Dihidrooxazol-4-il, 2,3-Dihidrooxazol-5-il, 3,4-Dihidrooxazol-2-il, 3,4-Diidrooxazol-3-il, 3,4-Diidrooxazol-4-il, 3,4-Diidrooxazol-5-il, 3,4-Diidrooxazol-2-il, 3,4-Diidrooxazol-3-yl, 3, 4-Dihydrooxazol-4-il, 2-, 3-, 4-, 5- ou 6-Di-oder Tetra-hydropyridinyl, 3-Di-oder Tetra-hydropyridazinyl, 4-Di-oder Tetra-hydropyridazinyl, 2-Di-oder Tetra-hydropyrmidinyl, 4-Di-oder Tetrahydropyrmidinyl, 5-Di-oder Tetrahydropyrmidinyl, Dioder Tetrahydropirazinyl, 1,3,5-Di-oder Tetrahydrotriazine-2-yl, 1,2,4-dioder tetrahidrotriazina-3-il, 2,3,4,5-tetrahidro[1H]azepina-1-, -2-, -3-, -4-, -5-, -6 - o -7-il, 3,4,5,6- Tetrahidro [2H]azepina-2-, -3-, -4-, -5-, -6- o -7-il, 2,3,4 ,7-tetrahidro[1H]azepina-1-, -2 -, -3-, -4-, -5-, -6- o -7-il,

2,3,6,7-Tetrahidro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, Tetrahidrooxepinil, como 2,3 ,4 ,5-Tetrahidro[1H]oxepina-2-, -3-, -4-, -5-, -6- o -7-il, 2,3,4,7-Tetrahidro[1H]oxepina -2-, -3-, -4-, -5-, -6- o -7-il, 2,3,6,7-tetrahidro[1H]oxepina-2-, -3-, -4-, -5-, -6- ou -7-il, Tetrahidro-1,3-diazepinil, Tetrahidro-1,4-diazepinil, Tetrahidro-1,3-oxazepinil, Tetrahidro-1,4-oxazepinil, Tetrahidro-1, 3-Dioxepinil y Tetrahidro -1,4-dioxepinilo.

Examples of a 3-, 4-, 5-, 6-, or 7-membered maximally unsaturated (including aromatic) heterocyclic ring are 5- or 6-membered heteroaromatic rings, such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1 -pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl , 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1 -oxopyridin-2-yl, 1-oxopyridin-3-yl, 1-oxopyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl, as well as residues homoaromatics such as 1H-azepine, 1H-[1,3]-diazepine and 1H-[1,4]-diazepine.

Examples of an 8-, 9-, or 10-membered saturated heterobicyclic ring with 1, 2, or 3 (or 4) heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as ring members are:

Examples of an 8-, 9-, or 10-membered partially unsaturated heterobicyclic ring with 1, 2, 3 (or 4) heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as ring members are:

Examples of an 8-, 9-, or 10-membered maximally unsaturated heterobicyclic ring with 1, 2, or 3 (or 4) heteroatoms or groups of heteroatoms selected from N, O, S, NO, SO, and SO2 as ring members are:

In the above structures, # denotes the point of attachment to the rest of the molecule. The point of attachment is not limited to the ring shown, but may be on any of the fused rings and may be on a carbon or nitrogen atom in the ring. If the rings bear one or more substituents, these may be attached to carbon and/or nitrogen atoms in the ring (as long as they are not part of a double bond). A 3-, 4-, 5-, 6-, 7-, 8-, or 9-membered saturated ring, which ring may contain 1 or 2 heteroatoms or groups of heteroatoms selected from O, S, N, NR¹⁴, NO, SO and SO2 and/or 1 or 2 groups selected from C=O, C=S and C=NR¹⁴as ring members it is carbocyclic or heterocyclic. Examples are, in addition to the aforementioned saturated heteromonocyclic rings, carbocyclic rings such as cyclopropyl, cyclopropanonyl, cyclobutyl, cyclobutanonyl, cyclopentyl, cyclopentanonyl, cyclohexyl, cyclohexanonyl, cyclohexadienonyl, cycloheptyl, cycloheptanonyl, cyclooctyl, cyclooctanonyl, furan-2-onyl, pyrrolidine -2-onyl, pyrrolidine-2,5-dionyl, piperidine-2-only, piperidine-2,6-dionyl and the like.

Modalities of the invention

In one embodiment of the invention, A in compounds of formula I is A¹. In another embodiment of the invention, A in compounds of formula I is A².

In another embodiment of the invention, A in compounds of formula I is A³.

In one embodiment of the invention, a method is provided, the method comprising applying a compound of formula 1.1 to soybean plants, a culture of soybean plants, their locus or their propagation material:

in what

R¹are you here₄-haloalkyl and is in particular CF₃;

R and R are independently selected from hydrogen, halogen, and CrC₂-haloalkyl, preferably hydrogen, F, Cl, Br and CF₃; is selected from hydrogen, halogen, cyan, CrC₄-Rent, CrC₄-Halogenalquilo, C₁-C4-Alcoxi, CrC₄-Halogenalcoxi, CrC₄-Alkyltio y CrC₄-haloalkylthio; preferably hydrogen, F, Cl, Br, CH₃, FC₃, mi₃, OFC₂H, OFC₃, CH₃, SCF₂El SCF₃;

R^{10 A}y R. S.^14aare independently selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, preferably hydrogen and CH₃; R^14bis selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-halogenocycloalkyl, C3-cycloalkyl C6-C1-C4-alkyl, where the cycloalkyl moieties in the last three groups may be replaced by a cyano group; C1-C6 alkyl substituted with cyano, C1-C6 alkoxy, C1-C6 haloalkoxy, phenyl optionally substituted with 1, 2, 3, or 4 substituents, each independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl , C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4 alkenyl, C2- C4 haloalkenyl, C2-C4 alkynyl and C2-C4 haloalkynyl; and a heteromonocyclic ring selected from rings of formulas D-1 to D-181

D-1 D-2 D-3 D-4 D-5

D-1 1 D-12 D-13 D-14

D-20 -21 D-22 D-23 D-24

D-25 D-27 D-28 D-29

D-40 D-41 D-42 D-43 D-44

D-45 D-46 D-47 D-48 D-49

D-50 D-51 D-52 D-53 D-54

D-70 D-71 D-72 D-73 D-74

D-75 D-76 D-77 D-78 D-79

D-85 D-86 D-87 D-88 D-89

-90 D-91 D-92 D-93 D-94

D-95 D-96 D-97 D-98 D-99

(

D-100 D-101 D-102 D-103 D-104

(R¹¹) (R¹¹) (R¹¹) (R¹¹)

D-105 D-106 D-107 D-108 D-109

D-110 D-111 D-112 D-113 D-114

D-115 D-116 D-117 D-118 D-119

D-125 D-126 D-127 D-128 D-129

D-130 D-132 D-133 D-134

D-135 D-136 D-1 7 D-138 D-139

D-140 D-141 D-142 D-143 D-144

D-145 D-146 D-147 D-148 D-149

D-150 D-151 D-152 D-153 D-154

D-155 D-156 D-157 D-158 D-159

D-175 D-176 D-177 D-178 D-179

D-180 D-181 onde

k is 0, 1, 2 or 3;

n is 0, 1 or 2; Y

every R¹¹is independently selected from the group consisting of halogen, cyano, nitro, Ci

C4-Alquil, Ci-C4-Halogenalquil, Ci-C4-Alcoxi, Ci-C4-Halogenalquilsulfinil, Ci-C4-Alquiltio, C1-C4-Halogenalquiltio, Ci-C4-Alquilsulfinil, Ci-C4-Halogenalquilsulfinil, Ci-C4- Alquilsulfonil, Ci-C4-Halogenalquilsulfonil, C3-C6-Cicloalquil, C3-C6-Halogencicloalquil, C2-C4-Alquenil, C2-C4-Halogenalquenil, C2-C4-Alquinil y C2-C4-Halogenalquinil, Ci-C4-Alkylcarbonyl, C1-C4-Alkylaminocarbonyl, ou

dos R¹¹present on the same carbon atom of a saturated heterocyclic ring can together form =O or =S; and where the method is to control and/or prevent pest infestation of soybean plants and/or soybean crops. Especially in 1.1 R compounds^14bis selected from C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl-C1-C4 alkyl, where the cycloalkyl radical may be replaced by a cyano group; C1-C6 alkoxy, C1-C6 haloalkoxy and phenyl.

In compounds 1.1 R⁴it can also be selected from C1-C4 alkylsulfinyl and C1-C4 haloalkylsulfinyl.

In another aspect of the present invention, the method comprising applying a compound of formula 1.1 to soybean plants and/or crops of soybean plants is to control and/or prevent infestation by pests of the family Pentatomidae, stink bugs. Preferably to control and/or prevent infestation by Acrosternum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha haiys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria, in particular to control and/or o Prevention of infestation by Acrosternum spp., Euschistus spp., Nezara spp. and/or Piezodrus spp., especially by Acrosternum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini, more especially by Euschistus heros and/or Nezara viridula, and especially by Euschistus heroes. Alternatively or additionally, the method serves in particular to control and/or prevent infestation by Halyomorpha halys.

In another aspect, the invention provides the use of a compound of formula 1.1 for controlling pests of the family Pentatomidae, bed bugs. Preferably to control Acrosternum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha halys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria, in particular to control Acrosternum spp., Euschistus spp., Nezara spp. and/or Piezodrus spp., in particular Acrosternum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini, very particularly to combat Euschistus heros and/or Nezara viridula and in particular Euschistus heros. Alternatively or additionally, the use serves in particular to combat Halyomorpha halys.

Compounds I.1 can also be used to control pests, preferably pests of the Pentatomidae family, bed bugs, preferably Acrosternum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha halys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria, particularly preferably Acrosternum spp., Euschistus spp., Nezara spp. and/or Piezodrus spp., especially Acrosternum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini, especially Euschistus heros and/or Nezara viridula and especially Euschistus heros resistant to one or more insecticides, preferably pyrethroids, neonicotinoids and organophosphates, and more preferably pyrethroid insecticides. Alternatively or additionally, compounds 1.1 can be used in particular to control Halyomorpha halys, which is resistant to one or more insecticides, preferably pyrethroid, neonicotinoid and organophosphate and particularly preferably pyrethroid insecticides. In another embodiment of the invention, a method is provided, the method comprising applying a compound of formula 1.2 to soybean plants, a culture of soybean plants, their locus or their propagation material:

in what

R¹are you here₄-Haloalkyl, especially CF₃; R, R and R are independently selected from hydrogen, halogen and CrC₂-haloalkyl, preferably hydrogen, F, Cl, Br and CF₃;

R⁴is selected from hydrogen, halogen, cyan, Ci-C₄-Alquil, Ci-C₄-Halogenalquilo, Ci-C₄- Alkoxy, CrC₄-halogenalcoxi, C1-C₄-alkylthio and Ci-C₄-Haloalkylthio, preferably hydrogen, F, Cl, Br, CH₃y FC₃; R⁵is selected from hydrogen, C1-C6-alkyl, C2-C₃-Alkenyl, C2-C₃-alkynyl, -CH2-CIM and

C1-C6-alkoxy-methyl, and preferably hydrogen and C1-C₄-I rent; and is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6₄-alkyl having a radical R⁸, C2-C6-Alquenil, C2-C6-Halogenalquenil, C2-C6-Alquinil, C₃-C6 cycloalkyl which may be substituted with 1 to 4 substituents selected from halogen and cyano; NOT^{10 A})R^10b, -CH=NOR⁹; Phenyl that can be substituted with 1, 2, 3, 4 or 5 R substituents¹¹, and a heteromonocyclic ring selected from rings of formulas D-1 to D-181 with their respective R substituents¹¹as defined above; R⁸is selected from hydrogen, OH, CN, C₃-C8-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, the last three mentioned radicals being partially or totally halogenated and/or substituted by one or more cyano groups; C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, where the last four radicals are partially or fully halogenated and/or can be selected by one or more substituents cyano, C₃-C6-Cycloalquil, C2-C6-Alquenyl e

C2-C6 alkynyl;

-C(=0)N(R^4a)R^4b; Phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents¹¹; and a heteromonocyclic ring selected from rings of formulas D-1 to D-181 with their respective R substituents¹¹as defined above;

R⁹is selected from hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkylmethyl, where the last three mentioned radicals can be partially or totally halogenated and/or substituted by one or more CN;

R^{10 A}is selected from the group consisting of hydrogen and C1-C6 alkyl;

R^10bis selected from the group consisting of hydrogen, C(=O)N(R^14a)R^14b; Phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents¹¹; and a heteromonocyclic ring selected from rings of formulas D-1 to D-181 with their respective R substituents¹¹as defined above; every R¹¹is independently selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy, C1-C4-Alkylthio, Ci-C4-Halogenalkylthio , Ci-C4-Alkylsulfinyl, Ci-C4-Halogenalkylsulfinyl, C1-C4- Alkylsulfonyl, Ci-C4-Halogenalkylsulfonyl, C3-C6-Cycloalkyl, C3-C6-Halogencycloalkyl, C2-C4-Alkenyl, C2-C4- Halogenalkenyl, C2 -C4-Alkynyl and C2-C4-Halogenalkynyl, Ci-C4-Alkynylcarbonyl,

C1-C4-alkylaminocarbonyl; tidy

dos R¹¹present on the same carbon atom of a saturated heterocyclic ring can together form =O or =S; each R^14ais selected from the group consisting of hydrogen and C1-C6 alkyl;

every R^14bis selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, C2-C4-alkynyl, C2-C4-alkenyl, C1-C4-alkoxy, the last six said radicals it can be partially or totally halogenated and/or substituted with a cyano group; and where the method is to control and/or prevent pest infestation of soybean plants and/or soybean crops.

In the 1.2R compounds⁵y R. S.⁶they can still together form a group in which R⁹is as defined above and is preferably C1-C4 alkyl.

In compounds I.2 R⁴it is preferably selected from hydrogen, halogen and C1-C4 alkyl.

In compounds I.2 R⁶it is selected in particular from hydrogen, C1-C4 alkyl, which carries a radical R⁸, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl which may be substituted with 1 to 4 substituents selected from halogen and cyano; y -N(R^{10 A})R^10b, worked⁸has one of the above definitions and is selected in particular from C₃-C8 cycloalkyl which may be partially or fully halogenated and/or substituted with one or more cyano groups;

-O-Chb-Cs-Ce-cycloalquil, -O-C₃-C₆-Alkenyl, -0-C₃-C₆-Alkynyl, -S(0)n-CH₂-C₃-C6-Cycloalquilo, -S(0)_norte-C₃-C₆-Alkenyl, -S(0)_norte-C₃-C₆-alkynyl where n is 0, 1 or 2; Y

-C(=0)N(R^4a)R^4b;

R^{10 A}is it hydrogen or ci-c₄-Rent;

R^0bis -C(=0)N(R^4a)R^4b;

R^14ais it hydrogen or ci-c₄-Rent; Y

R^14bis selected from the group consisting of hydrogen, C1-C6-alkyl, C₃-C6-Cicloalquilo, C₃-C6-Cycloalquilmethyl, C2-C₄-Alkynyl and C2-C₄-Alkenyl, where the last five radicals can be partially or totally halogenated and/or substituted by a cyano group.

In another aspect of the present invention, the method comprising applying a compound of formula 1.2 to soybean plants and/or crops of soybean plants is to control and/or prevent infestation by pests of the family Pentatomidae, stink bugs.

Preferably to control and/or prevent infestation by Acrosternum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha halys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria, in particular to control and/or o Prevention of infestation by Acrosternum spp., Euschistus spp., Nezara spp. and/or Piezodrus spp., especially by Acrosternum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini, more especially by Euschistus heros and/or Nezara viridula, and especially by Euschistus heroes. Alternatively or additionally, the method serves in particular to control and/or prevent infestation by Halyomorpha halys.

In another aspect, the invention provides the use of a compound of formula 1.2 for the control of pests of the family Pentatomidae, bed bugs. Preferably to control Acrosternum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha halys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria, in particular to control Acrosternum spp. , Euschistus spp., Nezara spp. and/or Piezodrus spp., in particular from Acrosternum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini, more particularly from Euschistus heros and/or Nezara viridula, and in particular from Euschistus heros. Alternatively or additionally, the use serves in particular to combat Halyomorpha halys. Compounds I.2 can also be used to control pests, preferably pests of the Pentatomidae family, bugs, preferably Acrosternum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha halys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria, particularly preferably from Acrosternum spp., Euschistus spp., Nezara spp. and/or Piezodrus spp., in particular from Acrosternum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini, more particularly from Euschistus heros and/or Nezara viridula, and in particular from Euschistus spp. resistant to one or more insecticides, preferably pyrethroids, neonicotinoids and organophosphates, and more preferably pyrethroid insecticides. Alternatively or additionally, compounds 1.2 can be used in particular to control Halyomorpha halys which is resistant to one or more insecticides, preferably pyrethroids, neonicotinoids and organophosphates, and particularly preferably pyrethroid insecticides.

As a particular embodiment of the invention, a method is provided, the method comprising applying to soybean plants, a culture of soybean plants, their locus or propagation material 2a:

in what

R¹it is C1-C4 haloalkyl and is especially CF3;

R^2a, R^2by R. S.^2care independently selected from hydrogen, halogen, and C1-C2 haloalkyl, preferably from hydrogen, F, Cl, Br, and CF3;

R⁴is selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio and C1-C4 haloalkylthio, preferably hydrogen, F, CI, Br, CH3 and CF3;

R⁵is selected from hydrogen, C1-C6 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, CH2-CN and C1-C6 alkoxymethyl and preferably from hydrogen and C1-C4 alkyl; Y

R^6ais selected from -X-R^6be-N(R^5a)R^6c; in what

X is selected from -C(R^and)₂-, -C(R^and)₂-C(R^and)₂-,

-C(R^and)₂-C(=O)-NO^0a-C(R^and)₂-, -C(R^and)₂S(0)n-C(R^and)₂-,

-C(R^and)₂-C(R^and)₂-S(0)n-C(R^and)₂-, -C(R^and)₂-0-C(R^and)₂-, mi

-C(R^and)2-C(R^and)₂-0-C(R^and)₂- and preferably -C(R^and)₂-,

-C(R^and)₂-C(=0)-NH-C(R^and)₂-, -C(R^and)2-C(R^and)₂-S(0)2-C(R^and)₂-, mi

-C(R^and)2-C(R^and)₂-0-C(R^and)₂-, in which

n is 0, 1, or 2, and

every R^andis independently selected from the group consisting of hydrogen, halogen, C1-C3 alkyl, and C1-C3 haloalkyl and is preferably hydrogen;

R^5aselected from hydrogen and C1-C6 alkyl, preferably hydrogen;_R6b is selected from the group consisting of C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, where the last three radicals may be partially or fully halogenated and/or substituted with one or more R substituents⁸;

_R6c é -C(=0)N(R^4a)R^4b

selección de Cyano, Ci-C6-Alcoxi, Ci-C6-Halogenalkoxi, Ci-C6-Alquiltio, C1-C6-Halogenalquiltio, Ci-C6-Alquilsulfinil, Ci-C6-Halogenalquilsulfinil, Ci-C6-Alquilsulfonil, C1-C6- Halogenalquilsulfonilo, -C(=O)N(R^4a)R^4b; every R^14ais selected from the group consisting of hydrogen and C1-C6 alkyl;

every R^14bis selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, C2-C4-alkynyl, C2-C4-alkenyl, C1-C4-alkoxy, the last six radicals mentioned it can be partially or totally halogenated and/or substituted with a cyano group; where in the case R⁵is hydrogen, R^6aIn addition, 1-cyanocyclopropyl, 1-cyanocyclobutyl and 1-cyanocyclopentyl are selected from hydrogen; and where the method is to control and/or prevent pest infestation of soybean plants and/or soybean crops.

Nos compostos l.2a R⁵y R. S.^6athey can still together form a group in which R⁹is as defined above and is preferably C1-C4 alkyl. In compounds 1.2a R⁴it is preferably selected from hydrogen, halogen and C1-C4 alkyl.

In another aspect of the present invention, the method comprising applying a compound of formula 1.2a to soybean plants and/or crops of soybean plants is to control and/or prevent infestation by pests of the family Pentatomidae, stink bugs.

In another aspect, the invention provides the use of a compound of formula 1.2a for controlling pests of the family Pentatomidae, bed bugs. Preferably to control Acrosternum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha halys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria, in particular to control Acrosternum spp. , Euschistus spp., Nezara spp. and/or Piezodrus spp., in particular from Acrosternum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini, more particularly from Euschistus heros and/or Nezara viridula and in particular from Euschistus heros. Alternatively or additionally, the use serves in particular to combat Halyomorpha halys.

Compounds 1.2a can also be used to control pests, preferably pests of the Pentatomidae family, bed bugs, preferably Acrosternum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha halys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria, particularly preferably from Acrosternum spp., Euschistus spp., Nezara spp. and/or Piezodrus spp., in particular from Acrosternum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini, in particular from Euschistus heros and/or Nezara viridula, and in particular from Euschistus spp. resistant to one or more insecticides, preferably pyrethroids, neonicotinoids and organophosphates, and more preferably pyrethroid insecticides. Alternatively or additionally, the use of compounds 1.2a may be in particular to control Halyomorpha halys resistant to one or more insecticides, preferably pyrethroid, neonicotinoid and organophosphate, and more preferably pyrethroid insecticides.

In another embodiment of the invention, a method is provided, the method comprising applying to soybean plants, a soybean plant culture, its locus or propagation material.

in what

R¹it is C1-C4 haloalkyl and is especially CF3; R, R and R are independently selected from hydrogen, halogen,

CRC₂-haloalkyl for CrC₂-Haloalkoxy, preferably hydrogen, F, Cl, Br, I, CF₃y OCF₃;

R⁴is selected from hydrogen, halogen, cyan, nitro, CrC₄-Rent, CrC₄-Halogenalkyl, C1-C4-Alkoxy, CrC₄-Halogenalcoxi, CrC₄-Alkyltio y CrC₄-haloalkylthio; preferably hydrogen, nitro, F, CI, Br, CH₃, FC₃, mi₃, OFC₂H, OFC₃, CH₃, SCF₂El SCF₃;

R⁵is selected from hydrogen, Ci-C₄-Rent, C₂-C₃-Alcinilo, -CH₂-CN , Ci-C6-Alkoxy-metil- y C₃-C6-cycloalkyl, and preferably hydrogen and C1-C₄-Rent; R.^7ais hydrogen or methyl;

R⁸is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C2-C6-alkenyl, where the last three radicals may be partially or fully halogenated and/or may be substituted by one or more substituents R may be substituted¹³; Ca-Ce-Alquinyl, -N(R^0a)R^0b,-C(=O)N(R^4a)R^4b, -O⁹, -CH=NOR⁹, phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents¹¹; and a heterocyclic ring selected from rings of formulas D-1 to D-181 with their respective R substituents¹¹as defined above;

R⁹it is selected from hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkylmethyl, the last three radicals being able to be partially or totally halogenated and/or substituted by one or more cyan groups;

R^{10 A}is selected from the group consisting of hydrogen and C1-C6 alkyl;

R^10bis selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-cycloalkyl,

the last two radicals being able to be partially or totally halogenated and/or optionally substituted by a cyano group; -C(=0)N(R^14a)R^14b; Phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents¹¹; and a heteromonocyclic ring selected from rings of formulas D-1 to D-181 with their respective R substituents¹¹as defined above; every R¹¹unabhängig ausgewählt ist aus der Gruppe bestehend aus Wasserstoff, Halogen, Cyano, Nitro, Ci-C4-Alquil, Ci-C4-Halogenalquil, Ci-C4-Alcoxi, Ci-C4-Halogenalcoxi, C1-C4-Alquiltio, Ci-C4- Halogenalquiltio, Ci-C4-Alquilsulfinil, Ci-C4-Halogenalquilsulfinil, C1-C4-Alquilsulfonil, Ci-C4-Halogenalquilsulfonil, C3-C6-Cicloalquil, C3-C6-Halogencicloalquil, C2-C4-Alquenil, C2-C4-Halogenalquenil, C2-C4-Alquinil y C2-C4-Halogenalquinil, Ci-C4-Alquilcarbonil, Ci-C4-Alquilaminocarbonil; ordenar

dos R¹¹present on the same carbon atom of a saturated heterocyclic ring can together form =O or =S;

R¹³ausgewählt ist aus Cyano, C3-C6-Cycloalquil, C3-C6-Halogencycloalquil, C1-C6-Alcoxi, C1-C6-Halogenalcoxi, Ci-C6-Alquilthio, Ci-C6-Halogenalquilthio, Ci-C6-Alquilsulfinil, C1-C6 - Halogenalquilsulfinil, Ci-C₆-Alquilsulfonyl, Ci-C₆-halogenalquilsulfonil, -N(R^14a)R^14b, -C(=0)N(R^14a)R^14b, phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents¹¹, and a heterocyclic ring selected from rings of formulas D-1 to D-181 with their respective R substituents¹¹as defined above and preferably selected from C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl ; and as a substituent on a cycloalkyl or cycloalkenyl ring is further selected from C1-C4 alkyl and C1-C4 haloalkyl; each R^14ais selected from the group consisting of hydrogen and C1-C6 alkyl; and each R^14bis selected from the group consisting of hydrogen, C1-C6 alkyl, C2-C4 alkynyl,

C₂-C₄-Alkenyl, -CH₂-CN, Ci-C₆-Halogenalquilo, C₃-C₆-Cicloalquil, C₃-C₆-Halogencycloalquil, C1-C4-Alkoxy, C1-C4-Halogenalkoxy y C3-C6-Cycloalquilmethyl;

and where the method is to control and/or prevent pest infestation of soybean plants and/or soybean crops.

In the above definitions, the years D-1 to D-181 are preferentially selected from two years D-1, D-2, D-3, D-7, D-18, D-19, D-20, D- twenty-one. D-71, D-72, D-73, D-75, D-76, D-77, D-78, D-82, D-107, D-108, D-109 and D-1 10.

In connections 1.3

every R⁸is independently selected preferably from the group consisting of hydrogen, C1-C6 alkyl, haloC1-C6 alkyl, C1-C6 alkyl substituted with an R substituent¹³; C3-C6 cycloalquil, C3-C6 halocycloalquil, C3-C6 cycloalquenyl, C3-C6 cycloalquil substituted with one or more substitutes R¹³; C₂-C₆-Alquenil, C₂-C₆-Halogenalquenil, C₃-C₈-Alkynyl, -C(=0)N(R^4a)R^4b, -O⁹, - CH=NOR⁹, phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents¹¹; and a heterocyclic ring selected from rings of formulas D-1 to D-181 with their respective R substituents¹¹as defined above, where R⁹, R¹³, R^14ay R. S.^14bare as defined above; and where preferably:

every R⁹is independently selected from hydrogen, C1-C6 alkyl, and C1-C6 haloalkyl; each R¹³is independently selected from cyano, C3-C6 cycloalquil, C3-C6 halocycloalquil, Ci-C6 alcoxi, Ci-C6 haloalcoxy, Ci-C6 alquilthio, Ci-C6 haloalquilthio, C1-C6 alquilsulfonyl, Ci- C₆-halogenalquilsulfonil, -N(R^4a)R^4b, -C(=0)N(R^4a)R⁴, phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents¹¹, and a heterocyclic ring selected from rings of formulas D-1 to D-181 with their respective R substituents¹¹as defined above and preferably selected from C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl; and as a substituent on a cycloalkyl or cycloalkenyl ring is further selected from C1-C₄-Rent and Ci-C₄-halogenalquila;

every R^14ais independently selected from hydrogen and C1-C4 alkyl; Y

every R^14bis independently selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C₂-C4-Alkenyl, C₂-C4 alkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl and C3-C6 cycloalkylmethyl. In a particular embodiment of the invention, a method is provided, which method comprises applying to soybean plants, a culture of soybean plants, their locus or propagation material.

in what

R¹are you here₄-haloalkyl and is in particular CF₃;

R^2a, R^2by R. S.^2care independently selected from hydrogen, halogen, and CrC₂-haloalkyl, preferably hydrogen, F, Cl, Br and CF₃;

R⁴is selected from hydrogen, halogen, cyan, Ci-C₄-Alquil, Ci-C₄-Halogenalquilo, Ci-C₄- Alkoxy, CrC₄-halogenalcoxi, C1-C₄-alkylthio and Ci-C₄-haloalkylthio; preferably hydrogen, F, Cl, Br, CH₃, FC₃, mi₃, OFC₂H, OFC₃, CH₃, SCF₂El SCF₃; R⁵is selected from hydrogen, Ci-C₄-Rent, C2-C₃-Alkynyl, -CH2-CN and C1-C6-alkoxymethyl, and preferably hydrogen and C1-C₄-Rent;

_R7a is hydrogen or methyl;

R⁸is selected from the group consisting of hydrogen, C1-C6-alkyl, C₃-C6-Cicloalquilo, C₃- C6-alkenyl, where the last three radicals can be partially or totally halogenated and/or substituted by one or more R substituents¹³; C₃-C₃- Alkynyl, -N(R^{10 A})R^10b,-C(=O)N(R^14a)R^14b, -CH=NOR⁹; Phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents¹¹; and a heterocyclic ring selected from rings of formulas D-1 to D-181 with their respective R substituents¹¹as defined above; R⁹is selected from hydrogen, C1-C6-alkyl, C₃-C6-Cicloalquilo, C₃-C6-cycloalkylmethyl, where the last three mentioned radicals can be partially or totally halogenated and/or substituted by one or more cyano groups;

R^{10 A}is selected from the group consisting of hydrogen and C1-C6 alkyl;

R^10bis selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 cycloalkyl, where the last two radicals may be partially or fully halogenated and/or optionally substituted with a cyano group; -C(=0)N(R^14a)R^14b; Phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents¹¹; and a heteromonocyclic ring selected from rings of formulas D-1 to D-181 with their respective R substituents¹¹as defined above; every R¹¹unabhängig ausgewählt ist aus der Gruppe bestehend aus Wasserstoff, Halogen, Cyano, Nitro, Ci-C4-Alquil, Ci-C4-Halogenalquil, Ci-C4-Alcoxi, Ci-C4-Halogenalcoxi, C1-C4-Alquiltio, Ci- C4- Halogenalquiltio, Ci-C4-Alquilsulfinil, Ci-C4-Halogenalquilsulfinil, C1-C4- Alquilsulfonil, Ci-C4-Halogenalquilsulfonil, C3-C6-Cicloalquil, C3-C6-Halogencicloalquil, C2-C4-Alquenil, C2-C4- Halogenalquenil, C2-C4-Alquinil y C2-C4-Halogenalquinil, Ci-C4-Alquilcarbonil, Ci-C4-Alquilaminocarbonil; ordenar

dos R¹¹present on the same carbon atom of a saturated heterocyclic ring can together form =O or =S;

R¹³selección de Cyano, Ci-C6-Alcoxi, Ci-C6-Halogenalkoxi, Ci-C6-Alquiltio, C1-C6-Halogenalquiltio, Ci-C6-Alquilsulfinil, Ci-C6-Halogenalquilsulfinil, Ci-C6-Alquilsulfonil, C1-C6 - Halogenalquilsulfonilo, -C(=O)N(R^14a)R^14b, phenyl optionally substituted with 1, 2, 3, 4 or 5 R substituents¹¹, and a heterocyclic ring selected from rings of formulas D-1 to D-181 with their respective R substituents¹¹as defined above and is preferably selected from C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfonyl and C1-C6 haloalkylsulfonyl; every R^14ais selected from the group consisting of hydrogen and C1-C6 alkyl; and each R^14bis selected from the group consisting of hydrogen, C1-C6 alkyl, C2-C4 alkynyl,

C₂-C₄-Alkenyl, -CH₂-CN, Ci-C₆-Halogenalquilo, C₃-C₆-Cicloalquil, C₃-C₆-Halogenocicloalquil, Ci-

alcoxi C4 y halogenalcoxi C1-C4, cicloalquilmetilo C3-C6;

and where the method is to control and/or prevent pest infestation of soybean plants and/or soybean crops.

In another aspect of the present invention, the method comprising applying a compound of formula 1.3 to soybean plants and/or crops of soybean plants is to control and/or prevent infestation by pests of the family Pentatomidae, stink bugs.

Preferably to control and/or prevent infestation by Acrostemum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha haiys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria, in particular to control and/or o Prevention of infestation by Acrostemum spp., Euschistus spp., Nezara spp. and/or Piezodrus spp., especially by Acrostemum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini, more especially by Euschistus heros and/or Nezara viridula, and especially by Euschistus heroes. Alternatively or additionally, the method serves in particular to control and/or prevent infestation by Halyomorpha halys. In another aspect, the invention provides the use of a compound of formula 1.3 for controlling pests of the family Pentatomidae, bed bugs. Preferably to control Acrosternum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha halys, Thyanta accerra, Podisus maculiventris and/or Megacopta cribraria, in particular to control Acrosternum spp., Euschistus spp., Nezara spp. and/or Piezodrus spp., in particular from Acrosternum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini, more particularly from Euschistus heros and/or Nezara viridula and in particular from Euschistus heros. Alternatively or additionally, the use serves in particular to combat Halyomorpha halys. The use of compounds of formula 1.3 can also be used to control pests, preferably pests of the Pentatomidae family, bugs, preferably Acrosternum spp., Euschistus spp., Nezara spp., Piezodrus spp., Dichelops spp., Halyomorpha halys, Thyanta, accerra, Podisus maculiventris and/or Megacopta cribraria are produced, particularly preferably from Acrosternum spp., Euschistus spp., Nezara spp. and/or Piezodrus spp., in particular Acrosternum hilare, Euschistus heros, Nezara viridula and/or Piezodrus guildini, more particularly Euschistus heros and/or Nezara viridula and in particular Euschistus spp. resistant to one or more insecticides, preferably pyrethroids, neonicotinoids and organophosphates and more preferably pyrethroid insecticides. Alternatively or additionally, the use of compounds 1.2a may be in particular to control Halyomorpha halys resistant to one or more insecticides, preferably pyrethroid, neonicotinoid and organophosphate, and more preferably pyrethroid insecticides.

pests

The compounds employed in the methods of the present invention can be used on soybeans, for example, to

Elasmopalpus lignosellus, Diloboderus abderus, Diabrotica speciosa, Sterneux subsignatus, Formicidae, Agrotis ypsilon, Julus ssp. B. Anticarsia gemmatalis, Megacopta spp., Megascelis ssp. , Procortermes ssp. , Gryllotalpidae, Nezara viridula, Piezodorus spp. , Acrosternum spp. , Neomegalotomus spp. B. Cerotoma trifurcata, Popillia japonica, Edessa spp. . , Acrosternum spp. , Cerotoma trifurcata, Popillia japonica, Euschistus heros, phyllophaga spp. B. Agriotes spp., Dectes texanus

Die erfindungsgemßen Verbindung werden werden vorbeschreibung auf Sojabohnen verwendet, um Stinkwanzen zu quwenden, z. Nezara sp. (z. B. Nezara viridula, Nezara antennata, Nezara hilar e), Piezodorus spp. (z. B. Piezodorus guildinii), Acrosternum spp. (z. B. Acrosternum hilare), Euschistus spp. {z.B. Euschistus heros, Euschistus servus), Halyomorpha halys, Megacopta cribaria, Plautia crossota, Riptortus clavatus, Rhopalus maculatus, Antestiopsis orbitalus, Dectes texanus, Dichelops spp. (z. B. Dichelops furcatus, Dichelops melacanthus), Eurygaster spp. (z. B. Eurygaster intergriceps, Eurygaster maurd), Oebalus spp. (z. B. Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Podisus sp., (z. B. Podisus maculiventris), Scotinophara spp. (z. B. Scotinophara lurida, Scotinophara coarctatd), Thyanta spp. (z. B. Thyanta accerra).

Acrosternum hilare, Antestiopsis orbitalus, Dichelops furcatus, Dichelops melacanthus, Euschistus heros, Euschistus servus, Megacopta cribraria, Nezara viridula, Nezara hilare, Piezodorus guildinii, Halyomorpha halys, Thyanta accerra, Podisus maculiventris, Megacopta cribraria. Most preferred targets include Acrosternum hilare, Antestiopsis orbitalus, Dichelops furcatus, Dichelops melacanthus, Euschistus heros, Euschistus servus, Megacopta cribraria, Nezara viridula, Nezara hilare, Piezodorus guildinii, Halyomorpha halys. In one embodiment, the bed bug targets Nezara viridula, Piezodorus spp., particularly Piezodorus guildinii, Acrosternum spp., Euschistus heros, and particularly Nezara viridula and/or Euschistus heros. The compounds according to the invention are particularly effective against euschist and in particular against euschist the hero. Euschistos, and in particular Euschistos the Hero, are the preferred targets. The compounds of the invention are also particularly effective against Halyomorpha halys.

forms

The application of the compounds of the invention is to a soybean plant crop, its locus or its propagation material. Preferably the application is to a soybean crop or locus, more preferably to a soybean crop. The application can be done before the infestation or when the pest is present. The application of the compounds according to the invention can be carried out by any of the usual application methods, e.g. Foliage, waterlogging, soil, furrow, etc. However, bed bug control is generally achieved by foliar application, which is the preferred mode of application according to the invention. The D.H. pest, the stink bug, the plant, the soil or the water in which the plant grows can be contacted with the present compounds of formula I or the composition(s) containing them by any other method of application known in the art. As such, "contact" includes both direct contact (application of the compounds/compositions directly to the animal or plant pest, typically the foliage, stem, or roots of the plant) and indirect contact (application of the compounds/compositions to the place) . animal or plant pest).

The compounds of formula I and their individual embodiments or pesticidal compositions containing them can be used to protect growing plants and crops from infestation or infestation by animal pests, in particular stink bugs, in particular Euschistus, in particular E. heros in contact with the Plant/crop containing a pesticidally effective amount of compounds of formula I. The term "crop" refers to both growing crops and crops.

The compounds of the invention can be used in combination with an attractant. An attractant is a chemical that causes the insect to migrate to the application site. For the control of bed bugs, it may be advantageous to apply the compounds of the invention with an attractant, particularly when applied foliarly. Stink bugs are often found close to the soil and the application of an attractant can encourage upward migration from the plant to the active substance. Suitable attractants include glucose, sucrose, salt, glutamate (eg Aji-no-moto™), citric acid (eg Orobor™), soybean oil, peanut oil, and soymilk. Glutamate and citric acid are of particular interest, with citric acid being preferred. An attractant can be premixed with the compound of the invention before use, e.g. B. as a premix or tank mix, or by simultaneous or sequential application in the plant. Suitable amounts of attractants are, for example, 0.02 kg/ha - 3 kg/ha.

The compounds according to the invention are preferably used for the control of pests in soybean at a rate of 1:500 g/ha, preferably 10-70 g/ha.

The compounds of the invention are suitable for use on any soybean plant, including those that have been genetically modified to be resistant to active ingredients, such as herbicides, or to produce biologically active compounds that control plant pest infestation. .

The compounds according to the invention are preferably used for the control of pests in soybean at a rate of 1:500 g/ha, preferably 10-70 g/ha.

In another preferred embodiment, transgenic plants and plant cultivars are treated which were obtained by genetic engineering methods, optionally in combination with conventional methods (genetically modified organisms), and parts thereof. Plants of plant varieties that are commercially available or in use are particularly preferably treated in accordance with the invention. Plant varieties are understood to be plants with new properties ("characteristics") that have been obtained by conventional breeding, mutagenesis or recombinant DNA techniques.

These can be varieties, organic or genotypes. Depending on the plant species or plant cultivars, their location and growth conditions (soil, climate, vegetation period, nutrition), superadditive "synergistic" effects can also be achieved by the treatment according to the invention.

For example, reduced application rates and/or broadening of the spectrum of activity and/or increased activity of the substances and agents that can be used according to the invention, improved plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or soil water or salt content, higher flowering yield, easier harvest, accelerated maturation, higher crop yield, higher quality and/or higher nutritional value of harvested products, better storage stability and/or possible processability of the harvested products, which go beyond the really expected effects.

Preferred transgenic plants or plant varieties (obtained by genetic engineering) to be treated according to the invention include all plants which have obtained genetic material as a result of genetic modification, which confers on them useful and particularly advantageous properties.

Examples of such characteristics are better plant growth, greater tolerance to high or low temperatures, greater tolerance to drought or soil water or salinity, better flowering performance, easier harvest, accelerated maturation, higher yields, higher quality and/or higher nutritional value of harvested products, better storage stability and/or processability of harvested products. Further and particularly prominent examples of such properties are a better defense of plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and/or viruses, and a higher tolerance of plants to certain herbicidal active ingredients. Increased plant defenses against insects, arachnids, nematodes, and snails due to toxins formed in plants, especially those formed in plants by the Bacillus thuringiensis genome (eg, by CryIA(a) genes) , CryIA(b), CryIA(c), CryllA, CryllA, CryllB2, Cry9c, Cry2Ab, Cry3Bb, and Cry9c, and combinations thereof) (referred to herein as "Bt plants"). Special emphasis is also placed on improving plant defenses against fungi, bacteria and viruses through systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and the corresponding expressed proteins and toxins.

The increased tolerance of plants to certain herbicidal active substances, for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example the "PAT" gene) is also particularly noteworthy as a characteristic. The genes conferring the respective desired properties can also be present in the transgenic plants in combination with each other.

Examples of "Bt crops" are soybean varieties sold under the trade names YIELD GARD(®).

Examples of herbicide-tolerant plants are soybean varieties sold under the trade names Roundup Ready(®) (glyphosate tolerance), Liberty Link(®) (phosphinothricin tolerance), IMI(®) (imidazolinone tolerance) and STS(®). (Tolerance to sulfonylureas).

As herbicide-resistant plants (plants conventionally bred for herbicide tolerance), varieties marketed under the name Clearfield® (for example, maize) may be mentioned.

Of particular interest are soybean plants with traits that confer resistance to 2 AO (eg.

Enlist®), glyphosate (for example, CropScience, Syngenta). Double or triple stack soybean plants with any of the characteristics described here are also of interest, including tolerance to glyphosate and sulfonylurea (for example, plants infected with Optimum GAT®, STS®, and Roundup Ready® or Roundup Ready 2 Yield® are stacked), dicamba and glyphosate tolerance (Monsanto). Also of interest are soybean resistant to cystic nematodes (SCN® - Syngenta) and soybean resistant to aphids (AMT® - Syngneta).

These statements also apply to plant varieties with these genetic characteristics or genetic characteristics yet to be developed that will be developed and/or commercialized in the future. mixes

Compounds of formula (I) can be applied in the methods of the present invention mixed with fertilizers (eg fertilizers containing nitrogen, potassium or phosphorus). Suitable formulation types include fertilizer granules. The mixtures preferably contain up to 25% by weight of the compound according to the invention.

The compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungicidal or plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.

The compounds employed in the methods of the present invention may be the sole active ingredient in the composition or, optionally, may be mixed with one or more additional active ingredients, such as pesticides, fungicides, synergists, herbicides, or plant growth regulators. An additional active agent can: provide a composition that shows a broader spectrum of activity or a longer persistence at one site; synergizing the activity or complementing the activity (eg, increasing the rate of action or overcoming repulsion) of the compound of the invention; or help overcome or prevent resistance to individual components. The specific additional active ingredient depends on the intended utility of the composition.

According to one embodiment of the present invention, the individual components of the composition according to the invention, as parts of a kit or parts of a binary or ternary mixture, can be mixed by the user himself in a spray tank and other excipients may be added. added. possibly.

In another embodiment, the individual components of the composition according to the invention or the partially premixed components, e.g. G. Components containing compounds I and/or active ingredients from groups M.1 to M.UN.X or F.I to F.XII can be mixed by the user in a spray tank and, if necessary, can be add auxiliary substances and additives. properly.

In another embodiment, the individual components of the composition according to the invention or the partially premixed components, e.g. G. Components containing compounds I and/or active ingredients from groups M.1 to M.UN.X or F.I to F.XII may be applied together (eg, using a tank mix) or in succession.

The following M list of pesticides, grouped according to the Insecticide Resistance Action Committee (IRAC) Classification of Mode of Action, with which the compounds of the invention may be used and with which potential synergistic effects may occur , is intended to illustrate the possible combinations, but without imposing a restriction:

M.1 inhibitors of acetylcholinesterase (AChE) of the class of

Carbamates M.1A, e.g. aldicarb, alanicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomil, metolcarb, oxamyl, pirimicarb, propoxur, thiodi- carbohydrate, tiofanox, trimetacarb, XMC, xylylcarb and triazamate; ou give class

M.1 B-Organofosfato, beispielsweise Acephat, Azamethiphos, Azinfos-ethyl, Azinfosmethyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Cumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/ DDVP, Dicrotophos, Dimetoato, dimetilvinfos, disulfotón, EPN, etión, etoprofos, famphur, fenamifos, fenitrotión, fentión, fostiazat, heptenofos, imicyafos, isofenfos, isopropil O-(metoxiaminotiofosforil) salicilato, isoxación, malatión, mecarbam, metamidofos, mevinfos, monocrotofos, naled, Omethoat, Oxydemeton-Methyl, Parathion, Parathion-Metil, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-Metil, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfoteps, Tebupirimfos, Temephos, Terbufos, Tetraclorvinfos, Tiometon, Triazofos, Triclorfon y Vamidotiona;

M.2. GABA-activated chloride channel antagonists, such as:

M.2A cyclodiene-organic chlorine compounds such as endosulfan or chlordane; or M.2B Fiprole (Phenylpyrazole), such as Ethiprole, Fipronil, Flufiprole, Pyrafluprole, and Pyriprole;

M.3 class sodium channel modulators

M.3A-Piretroide, zum Beispiel Acrinatrina, Aletrina, d-cis-trans-Aletrina, d-trans-Aletrina, Bifentrina, Bioaletrina, Bioaletrina S-Ciclopentenil, Bioresmetrina, Cicloprotrina, Ciflutrina, Beta-Ciflutrina, Cialotrina, Lambda-Cialotrina ., Momfluorotrina, Permethrina, Fenotrina, Praletrina, Proflutrina, Piretrina (Piretro), Resmetrina, Silafluofen, Teflutrina, Tetrametilflutrina, Tetrametrina, Tralometrina y Transflutrina; order

M.3B sodium channel modulators such as DDT or methoxychlor;

nicotinic acetylcholine receptor (nAChR) M.4 agonists of the neonicotinoid class M.4A, for example actteamiprid, clothianidin, dinotefuran, imidacloprid, nitenpiram, thiacloprid and thiamethoxam; or the connections

M.4A.1: 1-[(6-chloro-3-pyridinyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-(5S,8R)-5,8-epoxy -1H-imidazo[1,2-a]azepine; order

M.4A.2: 1-[(6-Chloro-3-pyridyl)methyl]-2-nitro-1-[(E)-pentylideneamino]guanidine; order

M4.A.3: 1-[(6-chloro-3-pyridyl)methyl]-7-methyl-8-nitro-5-propoxy-3,5,6,7-tetrahydro-2H-imidazo[1,2 -α]pyridine;

or Nicotine M.4B. M.5 allosteric activators of the nicotinic acetylcholine receptor of the spinosyn class, eg, spinosad or spinethor;

(Video) How Stink Bugs Damage Soybean Plants

M.6 chloride channel activators of the avermectin and milbemycin class, eg abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin;

M.7 Juvenile Hormonimimetika, do you know

M.7A juvenile hormone analogues, such as hydroprene, cynoprene, and methoprene; or others such as M.7B fenoxycarb or M.7C pyriproxyfen; M.8 different non-specific (multi-site) inhibitors, e.g.

M.8A Alkyl halides such as methyl bromide and other alkyl halides, or

M.8B chloropicrin, M.8C sulfuryl fluoride, M.8D borax, M.8E tartar emetic;

M.9 Homopteran selective feeding chokes, e.g.

M.9B Pymetrozin o M.9C Flonicamid;

M.10 mite growth inhibitor, for example

M.10A clofentezina, hexitiazox y diflovidazine o M.10B etoxazole; M.1 1 The microbial disruptors give membrana al intestino medio de los insects, por ejemplo Bacillus thuringiensis or Bacillus sphaericus, and the insecticidal proteins they produce, like Bacillus thuringiensis subsp. Israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki from Bacillus thuringiensis subsp. tenebrionis ou como vegetal proteins Bt: Cry-IAb, Crylac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb from Cry34/35Ab1;

M.12 Inhibitors of mitochondrial ATP synthase, p.

M.12A Diafentiuron, oder

organotin M.12B acaricides such as azocyclotin, cyhexatin or fenbutatin oxide or propargite M.12C or tetradiphon M.12D;

M.13 uncouplers of oxidative phosphorylation via proton gradient arrest, eg chlorfenapyr, DNOC or sulfluramid; M.14 nicotinic acetylcholine receptor (nAChR) channel blockers, for example, Nereis toxin analogues such as Bensultap, Cartap hydrochloride, thiocyclam or thiosultap sodium;

inhibitors of chitin biosynthesis type 0 M.15 such as benzoylureas such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron;

M.16 inhibitors of chitin biosynthesis type 1, such as buprofezin; M.17 mouse killers, flies such as cyromazine;

M.18 ecdysone receptor agonists such as diacylhydrazines, eg methoxyfenozide, tebufenozide, halofenozide, fufenozide or chromafenozide; M.19 octopamine receptor agonists such as amitraz;

Inhibitors of electron transport of the mitochondrial complex III M.20, for example

M.20A hydramethylnon or M.20B acequinocyl or M.20C fluacrypyrim; Inhibitors of electron transport of mitochondrial complex I M.21, p.

M.21 A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad or M.21 B rotenone;

Voltage Gated Sodium Channel Blockers M.22, p.

M.22A Indoxacarb o M.22B Metaflumizone o M.22C 1 -[(E)-[2-(4-Cyanofenil)-1-[3-(trifluorometil)fenil]etilideno]amino]-3-[4 -( difluorometoxi)fenil]urea;

M.23 acetyl-CoA carboxylase inhibitors, such as tetronic and tetramic acid derivatives, eg, spirodiclofen, spiromesifene or spirotetramate;

Inhibitors of electron transport of mitochondrial complex IV M.24, p.

Phosphine M.24A, as Aluminum Phosphide, Calcium Phosphide, or Phosphine

zinc phosphide or cyanide M.24B.

inhibitors of electron transport of the mitochondrial complex II M.25, such as beta-ketonitrile derivatives, for example, cyanopyraphen or cyflumethophene;

M.28 ryanodine receptor modulators of the diamide class, such as flubendiamide, chlorantraniliprole (Rynaxypyr®), cyantraniliprole (Cyazypyr®) or the phthalamide compounds M.28.1: (R)-3-chloro-N 1 -{ 2- Methyl- 4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide and

M.28.2: (S)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2 -methylsulfonylethyl)phthalamide, or Compound M.28.3: 3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl) -1 H-pyrazole-5-carboxamide (proposed ISO name: cyclaniliprol) or compound

M.28.4: Methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl})benzoyl] - carboxylate of 1,2-dimethylhydrazine; or a connection selected from M.28.5a) to M.28.5I):

M.28.5a) N-[4,6-Dicloro-2-[(dietil-lambda-4-sulfaniliden)carbamoil]-fenil]-2-(3-cloro-2-piridil)-5-(trifluormetil)pirazol -3-carboxamida;

M.28.5b) N-[4-Cloro-2-[(dietil-lambda-4-sulfaniliden)carbamoil]-6-metil-fenil]-2-(3-cloro-2-piridil)-5-(trifluormetil )pirazol-3-carboxamida;

M.28.5c) N-[4-Cloro-2-[(di-2-propil-lambda-4-sulfaniliden)carbamoil]-6-metil-fenil]-2-(3-cloro-2-piridil)- 5-(Trifluormetil)pirazol-3-carboxamida;

M.28.5d) N-[4,6-Dichloro-2-[(di-2-propyl-lambda-4-sulfanilideno)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluormethyl)pyrazol-3-carboxamide;

M.28.5e) N-[4,6-Dicloro-2-[(dietil-lambda-4-sulfaniliden)carbamoil]-fenil]-2-(3-cloro-2-piridil)-5-(difluormetil)pirazol -3-carboxamida;

M.28.5f) N-[4,6-Dibrom-2-[(di-2-propil-lambda-4-sulfaniliden)carbamoil]-fenil]-2-(3-cloro-2-piridil)-5- (trifluormetil)pirazol-3-carboxamida;

M.28.5g) N-[4-Chloro-2-[(di-2-propyl-lambda-4-sulfanilideno)carbamoyl]-6-cyano-phenyl]-2-(3-chloro-2-pyridyl) - 5-(Trifluormethyl)pyrazol-3-carboxamide;

M.28.5h) N-[4,6-Dibrom-2-[(dietil-lambda-4-sulfaniliden)carbamoil]-fenil]-2-(3-cloro-2-piridil)-5-(trifluormetil)pirazol -3-carboxamida;

Μ.28.5Ϊ) N-[2-(5-Amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methyl-phenyl]-5-bromo-2-(3-chloro- 2-pyridyl)pyrazol-3-carboxamide;

M.28.5j) 5-Chloro-2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(1-cyano-1-methyl-ethyl)carbamoyl]phenyl]pyrazole- 3-carboxamide;

M.28.5k) 5-Bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-2-(3,5-dichloro-2-pyridyl)pyrazole-3-carboxamide;

M.28.5I) N-[2-(tert-butylcarbamoyl)-4-chloro-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(fluoromethoxy)pyrazole-3-carboxamide; or a selected connection

M.28.6 N2-(1-Cyano-1-methyl-ethyl)-N1-(2,4-dimethylphenyl)-3-iodo-phthalamide; tidy

M.28.7 3-Chloro-N2-(1-cyano-1-methyl-ethyl)-N1-(2,4-dimethylphenyl)phthalamide;

Active ingredients of M.UN.X insecticide with unknown or uncertain mode of action, e.g. fluquinazone, sulfoxaflor, piflubumide or the compounds

M.UN.X.1: 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[( 2, 2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide or the compound

M.UN.X.2: ciclopropanessigsäure, 1,1'-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-ciclopropylacetyl)oxi]metil]-1 , 3,4,4a,5,6,6a,12,12a,12b-decahidro-12-hydroxy-4,6a,12b-trimetil-1 1 -oxo-9-(3-pyridinyl)-2H,1 1 H -Nafto[2,1-b]pyrano[3,4-e]pyrano-3,6-diyl]éster oder die Verbindung M.UN.X.3: 1 1 -(4-Chloro-2,6 -Dimetilfenil )-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-1 1-en-10-on, oder die Verbindung

M.UN.X.4: 3-(4'-Fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one , or the connection

M.UN.X.5: 1-[2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4 - triazol-5-amine from active principles from the base of Bacillus firmus (Votivo, 1-1582); O

M.UN.X.6; a compound selected from the group of

M.UN.X.6a) (E/Z)-N-[1-[(6-Chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamide; M.UN.X.6b) (E/Z)-N-[1-[(6-Chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamide;

M.UN.X.6c) (E/Z)-2,2,2-Trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide; M.UN.X.6d) (E/Z)-N-[1-[(6-Bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamide; M.UN.X.6e) (E/Z)-N-[1-[1-(6-Chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoroacetamide; M.UN.X.ef) (E/Z)-N-[1-[(6-Chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoroacetamide;

M.UN.X.6g) (E/Z)-2-Chloro-N-[1-[(6-Chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoroacetamide;

M.UN.X.6h) (E/Z)-N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylideno]-2,2,2-trifluoroacetamida e

M.UN.X.6i) (E/Z)-N-[1-[(6-Chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoropropanamide.) ; or the connections

M.UN.X.7: 3-[3-Chloro-5-(trifluoromethyl)phenyl]-4-oxo-1-(pyrimidin-5-ylmethyl)pyrido[1,2-a]pyrimidin-1-io- 2-olate; order

M.UN.X.8: 8-chloro-N-[2-chloro-5-methoxyphenyl)sulfonyl]-6-trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide; tidy

M.UN.X.9: 4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl ) ). ) Benzamide; order

M.UN.X.10: 5-[3-[2,6-Dichloro-4-(3,3-dichloralyloxy)phenoxy]propoxy]-1H-pyrazol; oder M.UN.X.1 1: 4-[5-(3,5-Dichlorophenyl)-5-(trifluormethyl)-4H-isoxazol-3-yl]-2-methyl-N-[2-oxo-2 - (2,2,2-trifluoroethylamino)ethyl]benzamide; order

M.UN.X.12: 4-[5-[3-Cloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[2-oxo-2- (2,2,2-trifluoroethylamino)ethyl]naphthalene-1-carboxamide.

The commercially available group M compounds listed above can be found in The Pesticide Manual, 15th Edition, CDS Tomlin, British Crop Protection Council (2011), among other publications.

The quinoline derivative, phlomethoquine, is shown in WO2006/013896. The aminofuranone compound flupyradifurone is known from WO 2007/115644. The sulfoximine compound sulfoxaflor is known from WO 2007/149134. Piflubumide acaricide is known from WO2007/020986. Isoxazoline compounds have been described: M.UN.X.1 in WO2005/085216, M.UN.X.9 in WO2013/050317, M.UN.X.11 in WO2005/085216 and M.UN.X. in WO2009/002809 and in WO2011/149749. The pyripyropene derivative M.UN.X.2 has been described in WO

2006/129714. The spiroketal-substituted cyclic ketoenol derivative M.UN.X.3 is known from WO2006/089633 and the biphenyl-substituted spirocyclic ketoenol derivative M.UN.X.4 from WO2008/067911. Finally, triazoylphenyl sulfides have been described as M.UN.X.5

WO2006/043635 and biological control agents based on Bacillus firmus in WO2009/124707. Neonicothionides 4A.1 are known from WO20120/069266 and WO2011/06946, M.4.A.2 from WO2013/003977, M4.A.3 from WO2010/069266.

The metaflumizone analogue M.22C is described in CN 10171577. The phthalamides M.28.1 and M.28.2 are known from WO 2007/101540. Anthranilamide M.28.3 has been described in WO2005/077934. The hydrazide compound M.28.4 has been described in WO 2007/043677. The anthranilamides M.28.5a) to M.28.5h) can be prepared as described in WO 2007/006670, WO2013/024009 and WO2013/024010, the anthranilamide M.28.5Ϊ) is described in WO2011/085575, which M. 28.5j) in WO2008/134969, M.28.5k) in US2011/046186 and M.28.5I) in WO2012/034403. The diamide compounds M.28.6 and M.28.7 can be found at CN102613183.

Compounds M.UN.X.6a) to M.UN.X.6i) listed in M.UN.X.6 have been described in

WO2012/029672. The mesoionic antagonist compound M.UN.X.7 has been described in

WO2012/092115, the nematicide M.UN.X.8 in WO2013/055584 and the pyridalyl-like analogue M.UN.X.10 in WO2010/060379. Preferred additional pesticidal active ingredients are those selected from Group 1 IRAC, acetylcholinesterase (AChE) inhibitors, here from Group 1A (carbamates) thiodicarb, methomyl and carbaryl, and from Group IB (organophosphates), especially acephates, chlorpyrifos and dimethoate. , from group 2B, fiproles, in particular etioproles and fipronil, group 3, pyrethroids, in particular lambda-cyhalothrin, alpha-cypermethrin or deltamethrin, and group 4A, neonicotinoids, in particular acetamiprid B Clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid or thiomethoxam.

In particular, combinations of compounds of the invention with fiprolene, neonictinoids or pyrethroids could potentially provide synergistic control of bed bugs (according to Colby's formula), in particular Euschistus, e.g. Euscist heroes.

The following list F of active ingredients in connection with which the compounds according to the invention can be used is intended to illustrate but not limit the possible combinations:

F.I) Atemhemmer

F.1-1) Complex III inhibitors at the Qo site:

Strobilurin: azoxystrobin, cumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pimethostrobin, pyroxystrobin, pyribencarbe, triclopyricarb/chlordinacarb, trifloxystrobin, 2-5-dimethyloxystrobin, methyl 2-5-dystrobin 2-(2-(3-(2,6-dichlorophenyl)-1-methylallylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methylacetamide 2-5-dimethylphendimethyl)-phenyl]-3-methoxy-acrylsäuremethyl ester;

oxazolidinediones and imidazolinones: famoxadone, fenamidone; F.I-2) Complex II inhibitors (for example, carboxamides):

Carboxanilida: Benodanil, Benzovindiflupyr, Bixafen, Boscalid, Carboxin, Fenfuram, Fenhexamide, Fluopyram, Flutolanil, Furametpyr, Isopyrazam, Isotianil, Mepronil, Oxycarboxin, Penflufen, Penthiopyrad, Sedaxan, Tecloftalam, Thifluzamid, Tiadinil, 2-Amino-4-metil - tiazol-5-carboxanilida, N-(3',4',5'-Trifluorbifenil-2-il)-3-difluormetil-1-metil-1H-pirazol-4-carboxamida (Fluxapiroxade), N-(4'- Trifluormetiltiobifenil-2-il)-3-difluormetil-1-metil-1H-pirazol-4-carboxamida, N-(2-(1,3,3-trimetil-butil)-fenil)-1,3-dimetil-5 Fluor-1H-pirazol-4-carboxamida, 3-(Difluormetil)-1-metil-N-(1,1,3-trimetilindan-4-il)pirazol-4-carboxamida, 3-(Trifluormetil)-1-metil -N-(1,1,3-Trimetilindan-4-il)pirazol-4-carboxamida, 1,3-Dimetil-N-(1,1,3-trimetilindan-4-il)pirazol-4-carboxamida, 3 -(Trifluormetil)-1,5-dimetil-N-(1,1,3-trimetilindan-4-il)pirazol-4-carboxamida, 3-(Difluormetil)-1,5-dimetil-N-(1,1 ,3-trimetilindan-4-il)pirazol-4-carboxami de, 1,3,5-trimetil-N-(1,1,3-trimetilindan-4-il) pirazol-4-carboxamid a, 3-(Difluormetil)-1-metil-N-(1,1,3- Trimetilindan-4-il)pirazol-4-carboxamida, 3-(Trifluormetil)-1-metil-N-( 1,1, 3-trimetilindan-4-il)pirazol-4-carboxamida, 1,3-dimetil-N-(1,1,3-trimetilindan-4-il)pirazol-4-carboxamida, 3-(trifluormetil)-1,5 -dimetil-N-(1,1,3-trimetilindano-4-il)pirazol-4 -Carboxamida, 3-(Difluormetil)-1,5-dimetil-N-(1,1,3-trimetilindano-4-il) )pirazol-4-carboxamida, 1,3,5-Trimetil-N-(1,1,3-Trimetilindan-4-il)pirazol-4-carboxamida;

F.I-3) Inibidor de Komplexes III an der Qi-Stelle: Cyazofamida, Amisulbrom, [(3S,6S,7R,8R)-8-Benzyl-3-[(3-acetoxy-4-methoxy-pyridin-2-carbonyl )amino ]-6-metil-4,9-dioxo-1,5-dioxonan-7-yl] 2-metilpropanoato, [(3S,6S,7R,8R)-8-benzyl-3-[[3-( acetoximethoxy)-4-methoxy-pyridin-2-carbonyl]amino]-6-metil-4,9-dioxo-1,5-dioxonano-7-yl]-2-metilpropanoato, [(3S,6S,7R,8R )-8-Benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridin-2-carbonyl)amino]-6-metil-4,9-dioxo-1,5-dioxonano-7-yl]-2- metilpropanoato, [(3S,6S,7R,8R)-8-Benzyl-3-[[3-(1,3-benzodioxol-5-ylmethoxy)-4-methoxy-pyridin-2-carbonyl]amino]-6- metil-4,9-dioxo-1,5-dioxonan-7-yl]-2-metilpropanoato, 3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl ]amino]-6-metil-4,9-dioxo-8-(fenilmetil)-1,5-dioxonan-7-yl-2-metilpropanoato;

F.I-4) Other respiratory inhibitors (complex I, uncouplers) diflumetorim; (5,8-Difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)phenyl]-ethyl}-amine; technazen; ametoctradine; silthiopham; Nitrophenyl derivatives: Binapacryl, Dinobuton, Dinocap, Fluazinam, Ferimzone, Nitrhal-Isopropyl,

and including organometallic compounds: fentin salts such as fentin acetate, fentin chloride or fentin hydroxide;

F.ll) Sterol biosynthesis inhibitors (SBI fungicides)

F.II-1) C14 demethylase inhibitors (DMI fungicides, e.g. triazoles, imidazoles)

Triazol: azaconazol, bitertanol, bromuconazol, ciproconazol, difenoconazol, diniconazol, diniconazol-M, epoxiconazol, fenbuconazol, fluquinconazol, flusilazol, flutriafol, hexaconazol, imibenconazol, ipconazol, metconazol, miclobutanil, paclobutrazol, penconazol, procontioiconazol, procontioiconazol, tebuconazol, tebuconazol, Tetraconazol, Triadimefão, Triadimenol, Triticonazol, Uniconazol, 1-[re/-(2S;3R)-3-(2-Clorofenil)-2-(2,4-difluorfenil)-oxiranilmetil]-5-tiocianato-1 H - [1 ,2,4]triazol, 2-[re/-(2S;3R)-3-(2-clorfenil)-2-(2,4-difluorfenil)-oxiranilmetil]-2H- [1,2, 4 ]triazol-3-tiol;

Imidazol: Imazalil, Pefurazoat, Oxpoconazol, Procloraz, Triflumizol; Pirimidina, Piridina y Piperazina: Fenarimol, Nuarimol, Pirifenox, Triforin, 1-[rel-(2S;3R)-3-(2-Clorofenil)-2-(2,4-difluorfenil)-oxiranilmetil]-5-tiocianato- 1H-[1,2,4]Triazol, 2-[rel-(2S;3R)-3-(2-clorofenil)-2-(2,4-difluorfenil)-oxiranilmetil]-2H-[1,2, 4]triazol-3-tiol; F.II-2) Delta14-Reduktase-Inibidor (Amina, z. B. Morfolina, Piperidina)

Morfolina: Aldimorph, Dodemorph, Dodemorph-Acetate, Phenpropimorph, Tridemorph;

piperidine: fenpropidin, piperaline; spiroketalamine: spiroxamine;

F.II-3) 3-keto-reductase inhibitors: hydroxyanilides: fenhexamide;

F.III) Nucleic acid synthesis inhibitors

F.III-1) Synthesis of RNA, DNA

Fenilamida o Acilaminosäure-Fungizide: Benalaxil, Benalaxil-M, Kiralaxil, Metalaxil, Metalaxil-M (Mefenoxam), Ofurace, Oxadixil;

Isoxazol e Isotiazolona: Hymexazol, Octilinon;

F.III-2) DNA toisomerase inhibitors: oxolinic acid;

F.III-3) Nukleotidstoffwechsel (z. B. Adenosin-Deaminase), Hidroxi-(2-amino)-pirimidina: Bupirimat;

F.IV) Inhibitors of cell division and/or the cytoskeleton

F.IV-1) Tubulin Inhibitor: Benzimidazole and Thiophanate: Benomyl, Carbendazim, Fuberidazole, Thiabendazol, Thiophanate-Methyl;

Triazolopirimidina: 5-Cloro-7-(4-metilpiperidin-1-il)-6-(2,4,6-trifluorfenil)-[1,2,4]triazolo[1,5a]pirimidina;

F.IV-2) Other inhibitors of cell division

Benzamida y Fenilacetamida: Diethofencarb, Etaboxam, Pencicuron, Fluopicolide, Zoxamida;

F.IV-3) Actin Inhibitor: Benzophenone: Metrafenone, Pyriophenone;

F.V) Amino acid and protein synthesis inhibitors

F.V-1 ) Inhibits methionine synthesis (anilinopyrimidine)

Anilinopirimidina: Ciprodinil, Mepanipirim, Nitrapirina, Pirimetanil;

F.V-2) Protein synthesis inhibitors (anilino-pyrimidines)

Antibiotics: Blasticidin-S, Kasugamycin, Kasugamycin-Hydrochloride-Hydrate, Mildiomycin, Streptomycin, Oxytetracycline, Polyoxin, Validamycin A;

F.VI) Signal transduction inhibitors

F.VI-1) MAP/Histidine Kinase Inhibitor (z.B. Anilino-Pyridine)

Dicarboximida: Fluorimida, Iprodion, Procimidon, Vinclozolina;

Phenylpyrrole: fenpiclonil, fludioxonil;

F.VI-2) G protein inhibitors: quinolines: quinoxyfen;

F.VI I) Inhibitors of the synthesis of lipids and membranes

F.VI 1-1) Phospholipid biosynthesis inhibitors

Organophosphates in combination: Edifenphos, Iprobenfos, Pyrazophos;

ditiolano: isoprotiolano;

F.VII-2) Lipid peroxidation: aromatic hydrocarbons: Dicloran, Quintozen, Tecnazen, Tolclofosmetil, Biphenyl, Chlorneb, Etridiazol;

F.VII-3) Carboxamides (CAA fungicides)

Cinnamic or mandelic acid amides: dimethomorph, flumorph, mandiproamide, pyrimorph; valineamide carbamates: benthiavalicarb, iprovalicarb, pyribencarb, valifenalate and N-(1-(1-(4-cyanophenyl)ethanesulfonyl)-but-2-yl)carbamic (4-fluorophenyl) ester;

F.VII-4) Compounds that affect the permeability of the cell membrane and fatty acids:

1-[4-[4-[5-(2,6-difluorphenyl)-4,5-di-hydro-3-isoxazolil]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3 -( Trifluormethyl)-1H-pyrazole-1-yl]etanone, Carbamato: Propamocarbe, Propamocarbe-chlorhidrato,

F.VII-5) Fatty acid amide hydrolase inhibitors: 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-

3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone; F.VIII) Inhibitor with multisite action

F.VIII-1) Inorganic agents: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;

F.VIII-2) Thio- de Dithiocarbamate: Ferbam, Mancozeb, Maneb, Metam, Metassulfocarb, Metiram, Propineb, Thiram, Zineb, Ziram;

F.VIII-3) Organochlorverbindungen (z. B. Ftalimida, Sulfamida, Clornitrilo):

Anilazine, chlorothalonil, captafol, captan, folpet, diclofluanida, dichlorofen, flusulfamide, hexachlorobenzene, pentachlorofenol y seus sais, phthalide, tolylfluanida, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide ;

F.VIII-4) Guanidines and others: guanidine, dodine, dodine free base, guazatin, guazatin acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate), 2,6-dimethyl-1H,5H[1, 4]dithiino[ 2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone;

F.VIII-5) Atraquinone: Dithianone;

F.IX) Cell wall synthesis inhibitors

F.IX-1) Glycan synthesis inhibitors: validamycin, polyoxin B;

F.IX-2) Melanin synthesis inhibitor: Pyroquilon, Triciclazole, Carpropamide, Dicyclomet, Fenoxanil;

F.X) Inductors of plant defenses

F.X-1) Salicylic acid pathway: acibenzenoar-S-methyl;

F.X-2) Outros: Probenazol, Isotianil, Tiadinil, Prohexadion-Calcium;

Phosphonates: fosetyl, fosetyl aluminum, phosphorous acid and its salts;

F.XI) Mode of action unknown: bronopol, chinomethionate, cyflufenamide, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, diphenzoquat methyl sulfate, diphenylamine, fenpyrazamine, flumetover, flusulfamide, flutianil, metasulfocarb, nitrapirin, isopropyl nitrothal, oxathiapiproline , oxine -Copper, proquinazid, tebufloquine, tecloftalam, triazoxide, 2-butoxy-6-iodo-3-propylchrome-

- Eins 2,5-Dimethyl-phenyl)-N-ethyl-N-methylformamidina, N' (4-(4-Fluor-3-trifluoromethyl-fenoxi)-2,5-dimethyl-phenyl)-N-ethyl-N -Metilformamidina , N'-(2-Methyl-5-trifluorometil-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-metilformamidina, N'-(5-Difluorometil-2-metil-4- (3-Trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidina, 2-{1-[2-(5-Methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidina-4- yl}-thiazol-4-carbonsäuremetil-(1,2,3,4-tetrahydro-naphthalin-1-yl)-amide, 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole). -1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-carbonsäuremetil-(R)-1,2,3,4-tetrahydro-naftalina-1-yl-amide, Methoxyessigsäure 6-tert-butilo The ester of -8-fluoro-2,3-dimethyl-quinolin-4-yl is N-methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl). )-acetyl]-piperidin-4-yl}-N-[(1,2,3,4-tetraí Dronaftalin-1-yl]-4-thiazolcarboxamida, 3-[5-(4-chloro-fenil)-2 , N -(6-methoxy-pyridin-3-yl)ciclopropancarbonsäureamida, 5-cloro-1 (4,6-dimethoxy-pyrimidin-2-yl)-2-metil-1H-benzoimidazole, 2-(4-cloro - phenyl) -N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxyacetamide.

F.XII) Growth regulators: Abscisic Acid, Amidochloro, Ancimidol, 6-Benzylaminopurine, Brassinolide, Butralin, Chlormequate (Chloromequate), Choline Chloride, Cyclanilide, Daminozide, Dikegulac, Dimetipine, 2,6-dimethylpuridine, Ethephon, Flumetraline, Flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N 6-benzyladenine, paclobutrazol, prohexadione (calcium prohexadione), prohydrojasmone, thidiazuron, triapenthenol, tributylphosphorotrithioate, 2,3,5-triiodobenzoic acid, trinexapac-ethyl, and uniconazole;

F.XIII) Biological control agents

Ampelomyces quisqualis (zB AQ 10^®von Intrachem Bio GmbH & Co. KG, Germany), Aspergillus flavus (z. B. AFLAGUARD^®von Syngenta, CH), Aureobasidium pullulans (z. B. BOTECTOR^®from bio-ferm GmbH, Germany), Bacillus pumilus (e.g., NRRL accession number B-30087 in SONATA^®and ballad^®More from AgraQuest Inc., USA. UU.), Bacillus subtilis (z. B. Isolate NRRL-No. B-21661 in RHAPSODY^®, serenade^®MAX and Serenade^®ASO von AgraQuest Inc., EUA), Bacillus subtilis var. amyloliquefaciens FZB24 (zB TAEGRO^®von Novozyme Biologicals, Inc., EUA), Candida oleophila I-82 (z. B. ASPIRE^®von Ecogen Inc., EE. UU.), Candida saitoana (z. B. BIOCURE^®(mixed with lysozyme) and BIOCOAT^®from Micro Flo Company, USA (BASF SE) and Arysta), chitosan (eg ARMOR-ZEN from BotriZen Ltd., NZ), Clonostachys rosea f. catenulata, also called Gliocladium catenulatum (for example, isolate J 1446: PRESTOP^®from Verdera, Finland), threatening coniotyry (eg, CONTANS^®from Prophyta, Germany),

Cryphonectria parasitica (z. B. Endothia parasitica von CNICM, Frankreich), Cryptococcus albidus (z. B. YIELD PLUS^®from Anchor Bio-Technologies, South Africa), Fusarium oxysporum (eg, BIOFOX^®von S.I.A.P.A., Italia, FUSACLEAN^®da Natural Plant Protection, France),

Metschnikowia fructicola (z.B. SHEMER^®von Agrogreen, Israel), Microdochium dimerum (z. B. ANTIBOT^®aus Agrauxine, Frankreich), Phlebiopsis gigantea (z. B. ROTSOP^®of Verdera, Finland), Pseudozyma flocculosa (e.g., SPORODEX^®Von Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (z. B. POLYVERSUM^®from Remeslo SSRO, Biopreparations, Czech Rep.), Reynoutria sachlinensis (for example, REGALIA^®von Marrone Biolnnovations, EUA), Talaromyces flavus V1 17b (z. B. PROTUS^®de Prophyta, Germany), Trichoderma asperellum SKT-1 (p. e.g., ECO-HOPE^®von Kumiai Chemical Industry Co., Ltd., Japan), T. atroviride LC52 (z. B. SENTINEL^®von Agrimm Technologies Ltd, NZ), T. harzianum T-22 (z. B. PLANTSHIELD^®der Firma BioWorks Inc., EUA), T. harzianum JH 35 (z. B. ROOT PRO^®de Mycontrol Ltd., Israel), T. harzianum T-39 (p. ej., TRICHODEX^®y TRICHODERMA 2000^®of Mycontrol Ltd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride (e.g., TRICHOPEL of Agrimm Technologies Ltd., NZ), T. harzianum ICC012 and T. viride ICC080 (e.g. , REMEDIER^®WP of Isagro Ricerca, Italy), T. polysporum and T. harzianum (for example, BINAB^®from BINAB Bio-Innovation AB, Sweden), T. stromaticum (for example, TRICOVAB^®von C.E.P.L.A.C., Brasil), T. virens GL-21 (z. B. SOILGARD^®da Certis LLC, EUA), T. green (for example, TRIECO^®by Ecosense Labs. (India) Private. Ltd., Yes, BIO-CURE^®F por T. Stanes & Co. Ltd., India), T. v/^'r/^'de TV1 (ex., T. viride TV1 de Agribiotec srl, Italia), Ulocladium oudemansii HRU3 (ex., BOTRY-ZEN^®by Botry-Zen Ltd, New Zealand). The commercially available Group F II compounds listed above can be found in The Pesticide Manual, 15th Edition, CDS Tomlin, British Crop Protection Council (2011), among other publications. Its production and efficacy against harmful fungi is known (cf.:

http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by the IUPAC nomenclature, their preparation and their fungicidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP A 141 317; EP-A 152 031; EP -A 152 031). A226917; EPA 243 970; EPA 256 503; EP-A-428 941; EP-A-532 022; EP-A 1 028 125; EP-A 1 035 122; EPA 1 201 648; EP-A 1 122 244, JP 2002316902; DE19650197; DE10021412; DE102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; document WO 99/24413; document WO 99/2704;2; document WO 00/65913; document WO 01/54501; document WO 01/56358; document WO 02/22583; document WO 02/40431; document WO 03/10149; document WO 03/11853; document WO 03/14103; document WO 03/16286; WO 03/53145, WO 03/61388, WO 03/66609, WO 03/74491, WO 04/49804, WO 04/83193, WO 05/120234, WO 05/123689, WO 05/123690, WO 05/63721, document WO 05/87772; document WO 05/87773; document WO 06/15866; document WO 06/87325; document WO 06/87343; document WO 07/82098; WO 07/90624, WO 11/028657). The compounds of this invention may be mixed with soil, peat, or other rooting media to protect plants against seed-, soil-, or foliar-borne diseases.

Examples of suitable synergists for use in the compositions include piperonyl butoxide, sesame, safroxane and dodecylimidazole.

Herbicides and plant growth regulators suitable for inclusion in the compositions depend on the intended purpose and the required effect.

An example of a selective rice herbicide that can be included is propanil. An example of a plant growth regulator for use on cotton is PIX™.

Some mixtures may include active ingredients that have significantly different physical, chemical, or biological properties that do not readily lend themselves to the same formulations.

The invention also relates to agrochemical compositions containing one or more adjuvants and at least one compound of formula (I) and/or one of its individual embodiments, used in the methods of the present invention.

An agrochemical composition comprises a pesticidally effective amount of a compound of formula (I) and/or any of its individual embodiments. The term "effective amount" indicates an amount of the composition(s) I which is sufficient to control animal pests on crop plants or in the protection of materials and which does not lead to any significant damage to the treated plants. This amount can vary greatly and depends on many factors, such as the pest species to be controlled, the crop or growing material treated, weather conditions, and the specific pound of corn used.

Compounds I, their N-oxides and salts can be incorporated into common types of agrochemical compositions, e.g. G. solutions, emulsions, suspensions, powders, pastes, granules, granules, capsules, and mixtures thereof. Examples of compound types are suspensions (eg SC, OD, FS), emulsifiable concentrates (eg EC), emulsions (eg EW, EO, ES, ME), capsules (eg eg, CS, ZC), pastes, tablets, powders or wettable powders. (eg, WP, SP, WS, DP, DS), granules (eg, BR, TB, DT), granules (eg, WG, SG, GR, FG, GG, MG) , insecticidal articles (eg LN), as well as gel formulations for the treatment of plant propagation material such as seeds (eg GF). These and other types of compositions are defined in the "Catalogue of Pesticide Formulation Types and International Coding System", Technical Monograph No. 2, 6th edition. May 2008, CropLife International.

The compositions are prepared in a known manner, as described by Mollet and Grubemann, Formulation Technology, Wiley VCH, Weinheim, 2001; o Knowles, New Developments in Crop Protection Product Formulation, Agrow Reports DS243, T&F Reports, London, 2005. Suitable excipients are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetrating , protective colloids, adhesives, thickeners, moisturizers, repellents, attractants, food stimulants, compatibilizers, bactericides, antifreezes, antifoams, dyes, stickies and binders. Suitable liquid vehicles and solvents are water and organic solvents such as medium to high boiling mineral oil fractions, e.g. kerosene, diesel; vegetable or animal oils; aliphatic, cyclic and aromatic hydrocarbons, e.g. G. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, eg ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example cyclohexanone; esters, eg lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, eg N-methylpyrrolidone, dimethyl fatty acid amides; and their mixtures.

Suitable solid carriers or fillers are mineral earths, for example silicates, silica gel, talc, kaolin, limestone, chalk, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulphate, magnesium sulphate, oxide of magnesium; polysaccharides, eg cellulose, starch; fertilizers, eg ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; Plant-based products, e.g. Cereal flour, bark flour, wood flour, walnut shell flour and their mixtures.

Suitable surfactants are surfactant compounds such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. These surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Examples of surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Edition or North American Edition).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, oil and fatty acid sulfonates, ethoxylated alkylphenol sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalene sulfonates, dodecyl sulfonates, and benzenes. tridecyl, naphthalene and alkylnaphthalene sulfonates, sulfosuccinates or sulfosuccinates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkyl phenols, of alcohols, of ethoxylated alcohols or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates. Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. For the alkoxylation it is possible to use ethylene oxide and/or propylene oxide, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose, and glucose esters or alkyl polyglycosides. Examples of polymeric surfactants are homemade or copolymers of vinylpyrrolidone, vinyl alcohols or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups or long chain primary amine salts. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines. Suitable adjuvants are compounds which by themselves have negligible or even no pesticidal activity and which enhance the biological performance of the compound of formula (I) on the target. Examples are surfactants, mineral or vegetable oils and other auxiliaries. Knowles offers other examples, Adjuvants and additives, Agrow Reports DS256, T&F Reports UK, 2006, Chapter 5.

Suitable thickening agents are polysaccharides (eg xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones.

Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.

Suitable defoamers are silicones, long chain alcohols and salts of fatty acids.

Suitable colorants (for example, in red, blue or green) are pigments with low water solubility and water-soluble dyes. Examples are inorganic dyes (eg iron oxide, titanium oxide, iron hexacyanoferrate) and organic dyes (eg alizarin, azo and phthalocyanine dyes).

Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes and cellulose ethers. The agrochemical compositions generally contain between 0.01% and 95% by weight, preferably between 0.1% and 90% by weight and more particularly between 0.5% and 75% by weight of active ingredient. The active ingredients are used with a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum). Seed treatment solutions (LS), Suspoemulsions (SE), Flowable concentrates (FS), Dry treatment powders (DS), Water dispersible powders for slurry treatment (WS), Water soluble powders (SS) , emulsions (for the treatment of plant propagation material, especially seeds, ES), emulsifiable concentrates (CE) and gels (GF). After dilution two to ten times in ready-to-use preparations, the compositions in question produce active substance concentrations of 0.01 to 60% by weight, preferably 0.1 to 40% by weight. It can be used before or during planting. Methods for applying a compound of formula (I) or compositions thereof to plant propagation material, in particular seeds, include methods of applying the propagation material by treating, coating, granulating, spraying, dipping and furrowing. Preferably, the compound of formula (I) or compositions thereof are applied to plant propagation material by a method which does not induce germination, e.g. G.B. by pickling, granulating, coating and powder application.

When used in crop protection, the application rates of the active ingredients are, depending on the type of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, especially preferably from 0. 05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per hectare.

In the treatment of plant propagation material as seeds, e.g. G.B. dusting, coating or soaking the seeds, amounts of active ingredient 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g and most preferably 5 to 100 g per 100 kg of plant growing material (preferably seeds).Generally necessary.

When used to protect stored materials or products, the amount of active ingredient used depends on the type of application and the desired effect. Usual application amounts in material protection are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active ingredient per cubic meter of treated material.

The active ingredients or compositions containing them can be added as a premix or optionally different types of oils, wetting agents, adjuvants, fertilizers or micronutrients and other pesticides (eg herbicides, insecticides, fungicides, growth regulators, protectants) just right. immediately before use (tank mixing). These agents can be added to the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user generally applies the composition according to the invention from a pre-dispensing device, knapsack sprayer, spray tank, spray plane or irrigation system. The agrochemical composition is generally adjusted to the desired use concentration with water, buffer and/or other auxiliaries, and thus the spray liquor or ready-to-use agrochemical composition according to the invention is obtained. Typically 20 to 2000 litres, preferably 50 to 400 litres, of ready-to-use spray mixture are applied per hectare of agricultural land. According to one embodiment, the individual components of the composition according to the invention, such as parts of a kit or parts of a binary or ternary mixture, can be mixed by the user himself in a spray tank and, if appropriate, other excipients can be added. added be added

In another embodiment, the individual components of the composition according to the invention or the partially premixed components, e.g. G. The components including the compounds I (or one of their individual embodiments) and/or the active substances of the groups M.1 to M.UN.X above can be mixed by the user in a spray tank and can be add other auxiliaries and additives. , possibly.

In another embodiment, the individual components of the composition according to the invention or the partially premixed components, e.g. G. Components containing compounds I (or one of their individual embodiments) and/or active substances from the groups M.1 to M.UN.X mentioned above can be applied together (for example by tank mixing) or in succession.

Examples The present invention will now be illustrated in greater detail by, but not limited to, the following examples.

C. Compounds Compounds for use in the methods of the present invention may, e.g. by liquid chromatography/coupled mass spectrometry (HPLC/MS) or by¹H-RMN.

Analytical HPLC column:

Analytical UPLC column: Phenomenex Kinetex 1.7 μηι XB-C18 100A; 50 x 2.1mm from Phenomenex, Germany. Elution: acetonitrile + 0.1% trifluoroacetic acid (TFA)/water + 0.1% trifluoroacetic acid (TFA) in a ratio of 5:95 to 100:0 in 1.5 min at 60°C. Flow rate: 0.8 ml/min to 1 ml/min in 1.5 min. MS method: ESI positive.¹H-NMR: The signals are characterized by the chemical shift (ppm, δδ) against tetramethylsilane, by its multiplicity, and by its integral (given the relative number of hydrogen atoms). The following abbreviations are used to characterize the multiplicity of signs: m = multiplet, q = quartet, t = triplet, d = doublet, and s = singlet.

The abbreviations used are: min for minute(s)

C.1 Examples of connection 1

Examples of compounds 1-1 to 1-38 correspond to compounds of formula C.1:

me what R^2a, R^2b, R^2c, R⁴, R^{10 A}, R^14ay R. S.^14beach synthesized compound is defined in the next row of Table C.1.

table d

Ex. R2a, R2b, R2c R4 R10a R14a R14b HPLC-N ES: Rt

(Min.) y M+H]⁺

1-1 CI, H, CI CH₃H H Cyclopropylmethylo 1.681 531 .0

1-2 CI, H, CI CH₃H H CH2CH3 1.681 503,2

1-3 CI, H, CI CI H H CH₃1.446 509,0

1-4 CI, H, CI CI H H CH₂Swiss francs₂1.475 560,9

1-5 CI, H, CI CI H H CH₂FC₃1.502 578,9

1-6 IC, H, IC IC H H CH2 CH3 1,319 523,0

1-7 CI, CI, CI OC₃H H CH₃1.448 540,8

1-8 CI, CI, CI OCH3 H H Prop-2-inyl 1.459 564.8

1-9 CI, CI, CI OCH3 H H CH₂FC₃1.503 608,9

1-10 CI, CI, CI SCH3 H H CH₂FC₃1.546 625,1

1-1 1 CI, CI, CI SCH3 H H CH₃1.488 555,0

1-12 CI, CI, CI SCH3 H H Prop-2-yl 1497 580.8

1-13 CI, CI, CI SCH3 H H CH₂Swiss francs₂1.518 607,1

1-14 CI, F, CI CI H H CH₂FC₃1.501 597,1

1-15 CI, F, CI CI H H CH₃1.455 529,1

1-16 CI, F, CI CI H H CH₂Swiss francs₂1.467 578,9

1-17 CI, CI, CI S(O)CH₃H H CH₃1.307 572,9

1-18 CI, CI, CI S(O)CH₃H H CH₂FC₃1.388 641.1

1-19 CI, CI, CI CH₃H H CH₃1.482 523,1 Bsp. R2a, R2b, R2c R4 R10a R14a R14b HPLC-N ES: Rt

(Min.) y M+H]⁺

1-20 IC, IC, IC CH₃H H CH₂FC₃1.527 591,1

1-21 IC, IC, IC CH₃H H E₃1.445 541,1

1-22 CI, CI, CI CH₃H H Prop-2-ilo 1,473 547,2

1-23 CI, CI, CI CH₃H H CH₂Swiss francs₂1.484 574,9

1-24 CI, F, CI CH₃H H CH₃1.405 507,1

1-25 CI, F, CI CH₃H H CH₂FC₃1.457 576,9

1-26 CI, F, CI CH₃H H CH₂Swiss francs₂1.436 557,1

1-27 CI, F, CI CH₃H H E₃1.373 525,0

1-28 CI, F, CI CH₃H H Prop-2-ilo 1.418 533.0

1-29 CI, CI, CI CI HALTO₃1.460 560,9

1-30 CI, CI, CI CI H H CH₂FC₃1.530 612,9

1-31 CI, CI, CI CI H H CH₂Swiss francs₂1.508 594,9

1-32 CI, CI, CI CI H H Prop-2-inilo 1,494 568.8

1-33 CI, CI, CI CI H H CH₃1.508 545,1

1-34 CI, H, CI CI CH₃H-phenyl 1,457,585.1

1-35 CI, H, CI CI CH₃HCH₃1.362 524,8

1-36 CI, H, CI CI H H Phenyl 1.379 573.0

1-37 IC, IC, IC SCH₃H H E₃1.432 572,9

1-38 CI, CI, CI F H H CH₂FC₃1.491 596,7

C.2 Compound Examples 2 Compound Examples 2-1 to 2-94 correspond to compounds of formula C.2:

me what R^2a, R^2b, R^2c, R⁴, R⁵y R. S.⁶each synthesized compound is defined in a row in Table C.2 below.

Table C.2

Ex. R^2a, R^2b, R^2cR⁴R⁵R⁶MS-HPLC:

magnetic resonance

2-1 CI, H, CI CHs H Cyclopropylmethyl 1.491 487.1

2-2 CI, H, CI CH H (3,3-difluorocyclobutyl)methyl 1466 537.3

2-3 CI, H, CI CHs H Ciclobutilmetil 1 ,51 1 501 ,1

2-4 CI, H, CI CHs H Cyclopentylmethylo 1.546 516.8 Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁶MS-HPLC:

magnetic resonance

2-5 CI, H, CI CHs H 1-Cianociclopropil 1.391 498

2-6 CI, H, CI CH H (1-cyanocyclopropyl)methylo 1392 512.1

2-7 CI, H, CI CH H prop-2-yl 1,396 471

2-8 C.I.H.C.I.CHsH Alilo 1.423 473

2-9 CI, H, CI CH H 3,4,4-trifluorobut-3-enilo 1477 541

2-10 CI, H, CI CHs =S(CH(CHs)₂)2 1.355 549,3

2-11 CI, H, CI CHs =S(CH₂CHs)2 1.308 521,3

2-12 IC, H, IC CH H (2,2- 1,51 557,2

dichlorocyclopropyl)methyl

2-13 IC, H, IC CH H 2,2,2-1,317 573,3

(Video) The BASF Yield Advantage

trifluoretilcarbamoilamino

2-14 CI, H, CI CH₃HH 1.310 433,2

2-15 CI, H, CI CHs H 2-oxo-2-(prop-2- 1.319 528,37

amino)ethyl

2-16 IC, H, IC CH H 2,2-1,318 555,4

difluoretilcarbamoilamino

2-17 CI, F, CI CH H (3,3-difluorocyclobutyl)methyl 1.463 555.2

2-18 CI, F, CI CH H (1-cyanocyclopropyl) methylo 1379 530.1

2-19 IC, F, IC CH H 2,2,2-1,321 591.1

trifluoretilcarbamoilamino

2-20 CI, F, CI CHsH Metilcarbamoilamino 1.246 524,9

2-21 CI, F, CI CHs H 2,2-Difluoroethyl-H NMR (400 MHz,

carbamoilamino-CDCI): δ 8,8 (br. s,

1H), 8,3 (br. s, 1H), 7,8- 7,2 (m, 5H), 6,2 (br. s, 1H), 5,8 (t, 1H), 4,2 (d, 1H), 3,85 (d, 1H), 3,6- 3,5 (m, 2H), 2,4 (s, 3H)

2-22 CI, F, CI CI H (3,3-difluorocyclobutyl)methyl 1.451 577.1

2-23 CI, F, CI CI H (1-cyanocyclopropyl)methyl 1,391 552.1

2-24 IC, F, IC IC H 2.2- 1,301,593

difluoretilcarbamoilamino

2-25 IC, F, IC IC H 2.2.2- 1.312 611

trifluoretilcarbamoilamino

2-26 CI, F, CI CI H 1-cyanocyclopropyl 1.405 538.1

2-27 CI, F, CI CI H Methylcarbamoylamino 1.247 544.9

2-28 CI, F, CI CHs H 1-Cianociclopropil 1.373 516,1

2-29 CI, F, CI CHs H Ciclobutilmetil 1.475 519,1

2-30 CI, F, CI CHs H 2-oxo-2-(prop-2- 1,308 546,1 Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁶MS-HPLC:

magnetic resonance

amino)ethyl

2-31 CI, F, CICH H (2.2- 1478 575

dichlorocyclopropyl)methyl

2-32 CI, F, CI CHs H Cyclopropylmethyl 1.427 505.1

2-33 C.I.F.C.I.Ch.sub.5 H Alilo 1.398 491.1

2-34 CI, F, CI CI H Prop-2-ynyl 509.73

1.381

2-35 IC, F, IC IC H Alila 1.414 513

2-36 CI, F, CI CI H Cyclobutylmethyl 1,486 539.8

2-37 CI, F, CI CI H (2,2- 1,484 594,66 Dichlorocyclopropyl)methyl

2-38 CI, F, CI CI H Cyclopentylmethyl 1.545 555

2-39 CI, F, CI CI H 3,4,4-trifluorobut-3-enyl 1474 581

2-40 CI, F, CI CI H 2-oxo-2-(prop-2- 1.32 566.78 inylamino)ethyl

2-41 CI, F, CI CI H Cyclopropylmethyl 1.437 527.1

2-42 CI, F, CI CHs H prop-2-ynyl 1.39 489.1

2-43 CI, F, CI CHs H NMR of 3,4,4-trifluorobut-3-enyl H (400 MHz,

CDCI): 57,6 (m, 2H), 7,4 (m, 3H), 6,0 (br. s, 1H), 4,2 (d, 1H), 3,85 (d, 1H), 3,7–3,6 (m, 2H), 2,8 -2,6 (m, 2H),

2,4 (s, 3H)

2-44 CI, H, CI CHs H 2-(Cyclopropyl- 1.376 580.9 Methylsulfonyl)ethyl

2-45 CI, H, CI CHs H 2-(cyclopropylmethoxy)ethyl 1.456 531.1

2-46 CI, H, CI CHs H (1-cyanocyclobutyl)methyl 1.43 528.2

2-47 CI, H, CI CHs H 1-Cianociclopentil 1.459 562,2

2-48 CI, H, CI CHs H 1-Cianociclobutil 1.425 512,1

2-49 CI, H, CI CHsH (1-cyanocyclopentyl)methylo 1.437 540.2

2-50 CI, H, CI CHs H (3,3-difluorocyclopentyl)methylo 1448 551.2

2-51 Cl, H, Cl CHs H 2-(Ciclopropilmetilamino)-2- 1,348 544,1 Oxoetilo

2-52 I,H,I CHs H 2-(Allylamino)-2-oxo-ethyl 1.321 530.1

2-53 CI, H, CI CHs H 2-Aliloxietil 1.419 517,1

2-54 CI, H, CI CHsH 2-[(1-Cianociclopropil)amino]- 1.289 555,1

2-oxo-ethyl

2-55 CI, F, CI CI H 2-(Cyclopropylmethylamino)-2- 1.343 584.0 Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁶MS-HPLC:

magnetic resonance

oxo-ethyl

2-56 CI, F, CI CHs H 2-(Cyclopropylmethylamino)-2- 1.334 562.1 Oxoethyl

2-57 CI, F, CI CI H Cyclohexylmethyl 1.554 569.1

2-58 CI, F, CI CHs H Ciclohexilmetil 1.544 547,2

2-59 CI, F, CI CHs H Cyclopentylmethyl 1.509 533.2

2-60 CI, F, CI CHs =S(CH₂CHs)2 1.380 561,4

2-61 CI, F, CI CHs H 1-Cianociclobutil 1.439 530,6

2-62 CI, F, CI CI H 1-cyanocyclobutyl 1.433 551.6

2-63 Hab, H, CF₃CI H 1-CN-Cyclopropyl 1.402 597.6

2-64 Hab, H, CF₃Cl H Alilo 1.444 573,5

2-65 Hab, H, CF₃CI H Prop-2-ilo 1.415 569.6

2-66 Hab, H, CF₃CI H Cyclopropylmethylo 1.466 584.7

2-67 CI, H, CI CHs H 2-Alilsulfoniletil 1.359 564,8

2-68 IC, H, IC CH H 2-1.419 594.6

(cyclobutylmethylsulfonyl)ethyl

2-69 IC, H, IC CHs H 2-Prop-2-inoxietil 1.390 214,8

2-70 Cl, H, Br Cl H Alil 1.443 539,5

2-71 Cl, H, Br Cl H Prop-2-inil 1.407 536,6

2-72 Cl, H, Br Cl H Ciclopropilmetil 1.468 552,6

2-73 Cl, H, Br Cl H 1-CN-Ciclopropilo 1.400 563,6

2-74 CI, F, CI CI H 1-cyanocyclopentyl 1,454 563.8

2-75 IC, F, IC CHs H 1-Cianociclopentil 1.442 543,8

2-76 CI, F, CI CI H (2,2-difluorocyclopropyl)methyl 1,451 563.6

2-77 CI, F, CI CHs H (2,2-difluorocyclopropyl)methyl 1.431 542.5

2-78 FC₃, H, FC₃CI H Cyclopropylmethylo 1.440 574.8

2-79 FC₃, H, FC₃CI H 1-CN-Cyclopropyl 1.387 585.8

2-80 FC₃, H, FC₃Cl H Alilo 1.414 560,8

2-81 Br, F, Br Cl H Alil 1.441 600,5

2-82 Br, F, Br Cl H Prop-2-inil 1.411 598,6

2-83 Br, F, Br Cl H 1-CN-Ciclopropilo 1.405 625,6

2-84 Br, F, Br Cl H Ciclopropilmetil 1.481 617,4

2-85 CI, H, CI CHs H 2-(cyclobutylmethoxy)ethyl 1.544 544.8

2-86 CI, H, CI CHs H (2,2-difluorocyclopropyl)methyl 1.443 524.6

2-87 FC₃, H, FC₃CI H Prop-2-yl 1.452 558.8

2-88 CI, F, CI CI H 2-[(1-Cyanocyclopropyl)- 1370 608.2 Methylamino]-2-oxo-ethyl

2-89 Cl, H, Cl CHs H 2-[(1-Cyanocyclopropyl)-1,349 568.4 Methylamino]-2-oxo-ethyl Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁶MS-HPLC:

magnetic resonance

2-90 CI, F, CI CI H 2-(Allylamino)-2-oxo-ethyl 1.341 569.6

2-91 C, F, C CHs H 2-(Allylamino)-2-oxo-ethyl 1.347 547.9

2-92 CI, F, CI NC-2 H Cyclopropylmethyl 1.41 1,535.8

2-93 CI, F, CI NC-2 H 1 -CN-Cyclopropyl 1.356 546.8

2-94 CI, F, CI CI H 2-[(1-cyanocyclopropyl)-

1,321 586.9 Methylamino]-2-oxo-ethyl

C.3 connection examples 3

Examples of compounds 3-1 to 3-265 correspond to compounds of formula C.3:

me what R^2a, R^2b, R^2c, R⁴, R⁵y R. S.⁸each synthesized compound is defined in a row in Table C.3 below.

Table C.3

Ex. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

3-1 CI, H, CI CHs CH2CH3 Methylsulfonylmethyl H NMR (400 MHz,

(m, 6H), 4,7 (s, 2H), 4,3-4,1 (m, 3H), 3,85 (d, 1H), 3,6-3,4 (m, 2H) , 3,2 (s, 3H), 2,35 (s, 3H), 1,3-1,1 (m, 2H)

3-2 CI, H, CI CI H Ethylsulfanylmethyl 1 .51 1 542.9

3-3 CI, H, CI CI H Cyclopropyl 1 .461 508.9

3-4 CI, H, CI CI CH2CH3 CH2CF3 1 555 579,2

3-5CI,H,CICICH2CH3CH₃1 .513 51 1 .1

3-6 CI, H, CI CI CH2CH3 CH2CH3 1 560 525,1

3-7CI,H,CICICH2CH3CH₂S(0)₂CH₃1.455 589,1 Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

3-8 CI, H, CI CI CH2CH3 Ethylsulfanylmethyl 1.596 571

3-9 CI, H, CI CI CH2CH3 trifluoromethylsulf- 1,603 611 phenylmethyl

3-10 IC, H, IC IC H CH2 CH3 1.430 497.2

3-11 CI, H, CI CI H CH₃1.379 481,1

3-12 IC, H, IC IC H CH2CF3 1.462 551,2

3-13 CI, H, CI CI CH2CH3 1,1-dioxothietan-3-yl 1.495 601.2

3-14 CI, F, CI CI H CH 1.397 501.0

3-15 CI, F, CI CI H CH₂S(0)₂CH3 1.379 578,9

3-16 CI, F, CI CI H Ethylsulfonylmethyl 1,407 592.8

3-17 CI, F, CI CI H Cyclopropyl 1,443 526.9

3-18CI,F,CICIH CH2CH3 1,432 513,0

3-19 IC, F, IC IC H CH2CF3 1.452 569,1

3-20 CI, F, CI CI H 1,1-dioxothietan-3-yl 1.373 591.0

3-21 CI, F, CI CI H 2-pyridyl 1.537 563.9

IC, F, IC 2.2-

3-22 CI H 1,471 562.8 Difluorocyclopropyl

IC, F, IC 2.2-

3-23 CI H 1.506 595.0 Dichlorocyclopropyl

3-24 CI, CI, CI F H CH 1.400 499.0

3-25 CI, CI, CI F H CH₂S(0)₂CH 3 H-NMR (400 MHz,

(m, 5H), 6,9 (br. s, 1H), 4,6 (d,2H), 4,2 (d, 1H), 3,9 (s, 2H), 3,8 (d, 1H), 3,1 (s, 3H)

3-26 CI, CI, CI F H Ethylsulfonylmethyl 1.379 578.9

3-27 IC, IC, IC HF CH2 CH3 1.459 515.0

3-28 CI, CI, CI F H Cyclopropyl 1.455 525.1

3-29 IC, IC, IC F H CH2CF3 1.462 569,0

3-30 IC, IC, IC OCH H CH2 CH3 1.418 526.9

3-31 IC, IC, IC OCH H CH2CF3 1.447 581.2

3-32 CI, CI, CI OCH HCH₂S(0)₂CH₃1.369 591,0

3-33 CI, CI, CI AND H Ethylsulfonylmethyl 1.396 605.1

3-34 IC, IC, IC SCH H CH2CF3 1.466 597.0

3-35 CI, CI, CI SCH H CH₂S(0)₂CH3 1.379 605,0

3-36 CI, CI, CI SCH H Ethylsulfonylmethyl 1.407 620.8

3-37 CI, CI, CI SCH H CH2CH3 1.442 542.9 Ej. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

3-38 CI, F, CI CI H 1-Fluorocyclopropyl 1.518 543.6

CI, F, CI 2-Cloro-2-Fluor-

3-39 CI H 1.509 579.6 Cyclopropyl

IC, F, IC 2.2-

3-40 CI H 1.548 553.7 Dimethylcyclopropyl

3-41 CI, F, CI CI H 1 -Methylsulphonylethyl 1.403 592.8

CI, F, CI 1-Methyl-1-

3-42 CI H 1.444 606.7 Methylsulfonyl-ethyl

3-43 CI, F, CI CI H 3,3,3-Trifluor-2- 1,557 592,7 Methyl-prop-1-enyl

3-44 CI, F, CI CI H Prop-1-enyl 1.456 526.6

3-45 CI, F, CI CI H 2-(2,2-difluoroethyl-1,401 606,7 amino)-2-oxoethyl

3-46 CI, F, CI CI H 2-oxo-2-(prop-2- 1,388 582,7 inylamino)ethyl

3-47 CI, F, CI CI H 1 -Methylcyclopropyl 1.513 541.5

3-48 CI, F, CI CI H 1-Fluorocyclobutyl 1.550 557.7

3-49 CI, F, CI CI H Tetrahydrofuran-2- 1,467 569,7 ylmethyl

3-50 CI, F, CI CI H Tetrahydrofuran-3- 1,426 571,5 ylmethyl

3-51 CI, F, CI CI H 2-(cyclopropylamino)- 1.381 581.8

2-oxo-ethyl

3-52 CI, F, CI CI H 3,3-Dichlorocyclobutyl 1.562 611.5

3-53 CI, H, CI CI CH CH CH CH 1,471 497.4

3-54 IC, H, IC IC cPr CHs 1.536 523.4

3-55 IC, H, IC IC cPr CH2CF3 1,583 589,7

3-56 CI, H, CI CI CHs CH2CF3 1.527 565,6

3-57 CI, H, CI CI CHs CH₂S(0)₂CH3 1.413 574,7

3-58 IC, H, IC IC cPr CH₂S(0)₂CH3 1.491 599,8

3-59 CI, H, CI CI Et 2,2- 1,643 605,6 Dichlorocyclopropyl

3-60 CI, H, CI CI Et Ethylsulfonylmethyl 1.485 602.6

3-61 CI, H, CI CI Et 2,2- 1,569 572,6 Difluorocyclopropyl

3-62 CI, F, CI CI H 1-cyanocyclobutyl 1.509 563.8

3-63 IC, F, IC IC H Oxetan-2-il 1,435 542,6

3-64 CI, F, CI CI H 2-(Ethylamino)-2-oxo- 1.388 569.8 Ethyl Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

3-65 CI, F, CI CI H Methoxyiminomethyl 1,488 543.6

3-66 CI, F, CI CI H Ethylcarbamoyl H NMR (400 MHz,

1H), 7,8 (s, 1H), 7,6 (m, 1H), 7,5-7,3 (m, 3H), 4,6 (m, 2H), 4,2 (d, 1H ), 3,8 (d, 1H), 3,4 (m , 2H), 1,2 (t, 3H)

3-67 CI, F, CI CI H Prop-2-ynylcarbamoyl 1,454 565.8

3–68 CI, F, CI CI H NMR of 2,2,2-trifluoroethyl-H (400 MHz, carbamoyl-CDCl): δ 7.9–7.3

(m, 6H), 6,1-5,7 (m, 1H), 4,6 (m, 2H), 4,2 (d, 1H), 3,85 (d, 1H), 3,8-

3,7 (metro, 2H)

3-69 CI, F, CI CI H Cyclobutyl 1,517 539.6

3-70 CI, F, CI CI H 2-Oxo-2-(2,2,2- 1,442 624,7 Trifluoroethylamino)ethyl

3-71 CI, F, CI CI H Cyclopropylcarbamoyl 1,494 570.6

3-72 CI, F, CI CI H 2,2-H NMR (400 MHz, difluoroethyl-CDCl): δ 7.9-7.3 Carbamoyl (m, 6H), 4.7-4.6

(m, 2H), 4,2 (d, 1H), 4,0-3,9 (m, 2H), 3,8 (d, 1H)

3-73 Hab, H, CF₃KI HCH2CF3 1.487 629,7

3-74 CI, F, CI Cl H n-Propyl 1.487 527.7

3-75 CI, F, CI CI H 2,2-Dimethylpropyl 1.552 556.6

3-76 CI, F, CI CI H 3,3,3-Trifluoropropyl 1,496 582,6

3-77 Hab, H, CF₃Brother H CH₂S(0)₂CH₃1.394 682,5

3-78 CI, F, CI Cl H sec-butyl 1,537 541.7

3-79 IC, F, IC IC H terc-butil 1.528 542.6

3-80 Hab, H, CF₃Br H Ethylsulfonylmethyl 1,420 696.5

3-81 Hab, H, CF₃Br H terc-butoxi H RMN (400 MHz,

CDCIs): δ 7,95 (s, 1H), 7,8 (s, 1H), 7,7 (s, 1H), 7,65 (d, Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

1H), 7,6 (s, 1H),

7,4 (d, 1H), 5,05

(br. s, 1H), 4,4 (m,

2H), 4,2 (d, 1H),

3,8 (d, 1H), 1,4 (s,

9 hours)

3-82 Br, F, Br Cl H terc-butoxi H RMN (400 MHz,

1H), 7,6 (d, 1H), 7,55 (m, 2H), 7,45 (d, 1H), 5,0 (br. s, 1H), 4,4 (m,2H), 4,2 (d, 1H), 3,8 (d, 1H), 1,5(s, 9H)

3-83 Hab, H, CF₃Br H CH2CF3 1.467 672,5

3-84 Hab, H, CF₃Br H CH2CH3 1.456 618,6

3-85 Hab, H, CF₃BrHCH 1.412 604,7

3-86 CI, F, CI CI H-Isobutil 1,500 542.7

3-87 Hab, H, CF₃BrH Cyclopropyl 1.471 630.6

3-88 Br, H, Cl Cl H terc-Butoxi H RMN (400 MHz,

CDCI): δ 7,8 (s, 1H), 7,7–7,4 (m, 4H), 7,3 (m, 1H), 5,05 (br. s, 1H), 4,4 ( m, 2H), 4,2 (d, 1H), 3,8 (d, 1H),

1,4 (s, 9H)

3-89 CI, F, CI CI H Cyclopentyl 1.537 554.6

3-90 CI, F, CI CI H Cyclohexyl 1.566 566.8

3-91 CI, F, CI CI H 2,2,3,3- 1,518 612,6 Tetrafluorocyclobutyl

3-92 CI, F, CI CI H (2,2,3,3-Tetrafluor- 1,514 626,6 Cyclobutyl)methyl

3-93 IC, F, IC IC H Oxetan-3-il 1,379 542,6

3-94 CI, F, CI CI H CH2CN 1.420 526.6

3-95 CI, F, CI CI H 2,2- 1,560 683,7 Dibromocyclopropyl

3-96 Hab, H, CF₃CI H CH₂S(0)₂CH₃RMN-H (400 MHz,

CDCIs): δ 7,8 (m, 2H), 7,75 (s, 1H), Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

7,7-7,5 (m, 2H), 7,5 (m, 1H), 6,9 (br. s, 1H), 4,6 (m,2H), 4,2 (d, 1H) , 3,9 (s, 2H), 3,8 (d, 1H), 3,1 (s, 3H)

(Video) Selecting the Best Herbicide For My Soybeans

3-97 Hab, H, CF₃CI H-ethylsulfonylmethyl-H-NMR (400 MHz,

2H), 7,75 (s, 1H), 7,7-7,5 (m, 2H), 7,5 (m, 1H), 6,95 (br. s, 1H), 4,6 (m ,2H), 4,2 (d, 1H), 3,9 (s, 2H), 3,85 (d, 1H), 3,15 (q,2H), 1,4 (t, 3H)

3-98 Hab, H, CF₃CI H CH 1,392 560.6

3-99 Hab, H, CF₃CI H Cyclopropyl 1.452 586.6

3-100 Br, H, CF₃CI H n-Propyl 1.470 588,6

3-101 Hab, H, CF₃Cl H CH 2 CH 3 1.432 574.6

3-102 FC₃, H, FC₃KI HCH2CF3 1.446 616,7

3-103 FC₃, H, FC₃Cl H CH 2 CH 3 1.415 562.8

3-104 FC₃, H, FC₃CI H CH 1,414 549.7

3-105 FC₃, H, FC₃CI H Cyclopropyl 1,470 575.7

3-106 FC₃, H, FC₃CI H n-Propyl 1.487 577,8

3-107 FC₃, H, FC₃CI H CH₂S(0)₂CH3 1.361 626,7

3-108 FC₃, H, FC₃CI H Ethylsulfonylmethyl 1,388 640.8

3-109 Br, F, Br Cl H CH2CF3 1.502 657,6

3-110 Br, F, Br CI H CH2CH3 1.473 603,6

3-111 CI, F, CI CI H Cyclobuten-1-il 1,480 538.6

3-112 Cl, F, Cl Cl H CH 2 AND 3 1,460 529.6

3-113 CI, F, CI CI H Dimethylaminomethyl 1.184 544.6

3-114 CI, F, CI CI H Tetrahidrofura n-2-ilo 1,490 555.7

3-115 CI, F, CI CI H 1,2,3,4,4,4-H RMN (400 MHz, Hexafluor-3-CDCI3): δ 7,8 (s, (Trifluormetil)but-1 - 1H ), 7,6 (m, 1H), Enil 7,5 (m, 1H), 7,4 (m,

2H), 6,8 (br. s, 1H), 4,7 (m, 2H), 4,2 (d, Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

1H), 3,85 (d, 1H)

3-116 CI, F, CI CI H Cyclopentylmethyl 1.561 569.6

3-117 CI, F, CI CI H l-(Trifluoromethyl)-H NMR (400 MHz, cyclopropyl CDCl): δ 7.8 (s,

1H), 7,6 (m, 1H), 7,5-7,3 (m, 3H), 6,7 (br. s, 1H), 4,6 (m, 2H), 4,2 (d , 1H), 3,8 (d, 1H), 1,45 (m,2H), 1,25 (m,

2H)

3-118 CI, F, CI CI H 2-(Trifluoromethyl)-H NMR (400 MHz, cyclopropyl CDCl): δ 7.8 (s,

1H), 7,6 (m, 1H), 7,5-7,25 (m, 3H), 6,2 (br. s, 1H),4,6 (m,2H),4,2 (d , 1H), 3,8 (d, 1H), 2,0 -1,8 (m, 2H), 1,6 (m, 1H), 1,2 (m,

1H)

3-119 CI, F, CI CI H CH 2 CH 2 OCH 3 1.441 545.5

3-120 CI, F, CI CI H Cyclohexylmethyl 1.609 583.7

3-121 CI, F, CI CI H Bencilo 1.531 577.7

3-122 Br, H, Cl Cl H CH2CF3 1.463 594,6

3-123 Br, H, Cl Cl H CH2CH3 1,434 540,6

3-124 Br, H, Cl Cl H CHs 1.389 526,6

3-125 Br, H, CI CI H CH₂S(0)₂CH₃RMN-H (400 MHz,

CDCI): δ 7,8 (s, 1H), 7,6–7,5 (m, 2H), 7,5–7,4 (m, 2H), 7,3 (s, 1H), 7, 0 (br. s, 1H), 4,6 (m, 2H). ), 4,2 (d, 1H), 3,95 (s, 2H), 3,8 (d, 1H), 3,1 (s,

3H)

3-126 Br, H, Cl Cl H Etilsulfonilmetil H RMN (400 MHz,

CDCIs): δ 7,8 (s, 1H), 7,6-7,5 (m, Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

2H), 7.5-7.4 (m,

2H), 7,3 (s, 1H),

7,0 (br.s, 1H),4,6

(m,2H),4,2 (d,

1H), 3,9 (s, 2H),

3,8 (d, 1H), 3,2 (q,

2H), 1,4 (t, 3H)

3-127 Br, H, Cl Cl H Ciclopropilo 1.488 553,7

3-128 Br, H, Cl Cl H n-Propil 1.509 555,6

3-129 CI, F, CI CI Hisopropyl 1.475 528.7

3-130 Hab, H, CF₃Br H n-Propyl 1.488 632,6

3-131 Br, F, Br CI H CH₂S(0)₂CH₃1.376 666,5

3-132 Br, F, Br Cl H Etilsulfonilmetil 1.405 682,4

3-133 Br, F, Br Cl H Ciclopropilo 1.461 614,6

3-134 Br, F, Br Cl H n-Propil 1.477 616,6

3-135 Br, F, Br Cl H CHs 1.396 588,6

3-136 CI, F, CI CI H Trifluoromethyl-H NMR (400 MHz, Sulfanylmethyl CDCl): δ 7.8 (s,

1H), 7,6 (m, 1H),

7,5 (m, 1H), 7,4 (m, 2H), 6,9 (br. s, 1H),

4,6 (m, 2H), 4,2 (d, 1H), 3,8 (d, 1H),

3.6 (s, 2 standard)

3-137 CI, F, CI CI H Tetrahydropyran-2- 1,524 583,7 ylmethyl

3-138 CI, F, CI CI H 2-thienylmethyl 1.519 583.6

3-139 CI, F, CI CI H Pyrimidin-2-ylmethyl 1,355 576.7

3-140 CI, F, CI CI H Oxetan-3-ylmethyl 1.360 554.8

3-141 Hab, H, CF₃FH CH2CF3 RMN-H (400 MHz,

CDCI): δ 7,8 (s, 1H), 7,7 (s, 1H), 7,6–7,4 (m, 4H), 6,2 (br. s, 1H), 4,55 ( m, 2H), 4,2 (d, 1H), 3,9 (d, 1H), 3,1 (m,

2H)

3-142 Hab, H, CF₃FH CH2CH3 1,430 559.7

3-143 Hab, H, CF₃F H CHs 1.383 545,6 Ej. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

3-144 Hab, H, CF₃F H CH₂S(0)₂CH₃RMN-H (400 MHz,

CDCI): δ 7,8 (s, 1H), 7,7 (s, 1H), 7,6–7,4 (m, 4H), 6,9 (br. s, 1H), 4,55 ( m, 2H), 4,2 (d, 1H), 3,9 (s, 2H), 3,85 (d, 1H), 3,05 (s, 3H)

3-145 Hab, H, CF₃FH-ethylsulfonylmethyl-H-NMR (400 MHz,

CDCI): δ 7,8 (s, 1H), 7,7 (s, 1H), 7,6–7,4 (m, 4H), 6,9 (br. s, 1H), 4,6 ( m, 2H), 4,2 (d, 1H), 3,9 (s, 2H), 3,85 (d, 1H), 3,15 (q,2H),

1,4 (t, 3H)

3-146 Hab, H, CF₃FH Cyclopropyl 1.401 568.7

3-147 Hab, H, CF₃F H n-Propyl 1.418 572,6

3-148 CI, F, CI F H CH2CF3 1.412 550,8

3-149 CI, F, CI F H Cyclopropyl 1.392 510.5

3-150 CI, F, CI F H n-Propyl 1.411 510.8

3-151 CI, F, CI F H CH2 CH3 1.402 498.5

3-152 CI, F, CI F H CH 1.371 482.8

3-153 CI, F, CI FH CA₂S(0)₂CH₃1.382 560,7

3-154 CI, F, CI F H Ethylsulfonylmethyl 1.409 574.7

3-155 Cl, F, Cl Cl H C(O)NHCH₃RMN-H (400 MHz,

CDCI): δ 7,9 (br. s, 1H), 7,8 (s, 1H), 7,6 (m, 1H), 7,5–7,3 (m, 3H), 4,6 ( m, 2H), 4,2 (d, 1H), 3,8 (d, 1H), 2,8 (m,

3H)

3-156 CI, F, CI Cl H Thietan-3-yl H RMN (400 MHz,

CDCI): δ 7,8 (s, 1H), 7,6 (m, 1H),

7,5 (m, 1H), 7,4 (m, 2H), 6,0 (br. s, 1H),

4,6 (m, 2H),4,2 (d, Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

1H), 4,0 (m, 1H), 3,8 (d, 1H), 3,6 (m, 2H), 3,2 (m, 2H)

3-157 CI, F, CI CI H 1,3-Dioxolan-2- 1,445 570,8 ylmethyl

3-158 CI, F, CI CI H 1,3-dioxan-2-ylmethyl 1.492 586.1

3-159 CI, H, FC₃CI H CH2 CH3 1.407 528.7

3-160 CI, H, CF₃CI H n-Propyl 1.425 544,6

3-161 CI, H, CF₃CI H Cyclopropyl 1.425 542.5

3-162 CI, H, FC₃CI H CH 1.365 516.5

3-163CI, H, CF₃CI H CH₂S(0)₂CH₃1.434 592,3

3-164 CI, H, FC₃CI H Ethylsulfonylmethyl 1,463 606.4

3-165 IC, H, FC₃KI HCH2CF3 1.551 582,3

3-166 F, H, CF₃KI HCH2CF3 1.503 566,4

3-167 F, H, FC₃CI H CH2 CH3 1.385 512.8

3-168 F, H, CF₃CI H CH 1,342 498.7

3-169 F, H, FC₃CI H Cyclopropyl 1.401 524.8

3-170 F, H, CF₃CI H n-Propyl 1.419 526,8

3-171 F, H, FC₃CI H CH₂S(0)₂CH₃RMN-H (400 MHz,

CDCI): δ 7,8 (s, 1H), 7,6 (d, 1H), 7,5 (m, 2H), 7,4 (d, 1H), 7,35 (d, 1H), 7 ,0 (br. s, 1H), 4,6 (m,2H), 4,2 (d, 1H), 3,95 (s, 2H), 3,85 (d, 1H), 3,1 ( s, 3H)

3-172 F, H, FC₃CI H-ethylsulfonylmethyl-H-NMR (400 MHz,

CDCI): δ 7,8 (s, 1H), 7,6 (d, 1H), 7,5 (m, 2H), 7,4 (d, 1H), 7,35 (d, 1H), 7 ,05 (br. s, 1H), 4,6 (m,2H), 4,2 (d, 1H), 3,9 (s, 2H), 3,85 (d, 1H), 3,15 ( q,2H), 1,4 (t,3H)

3-173 CI, F, CI CI H 1-Cyanocyclopropyl 1.480 551.6 Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

3-174 CI, F, CI CI H 2-Methoxycyclohexylo 1,575 598.8

3-175 Br, H, Br Cl H CH2CF3 1.654 638,9

3-176 Br, H, Br Cl H Ciclopropilo 1.471 596,7

3-177 Br, H, Br Cl H CH2CH3 1.450 584,6

3-178 Br, H, Br Cl H CHs 1.593 570,9

3-179 Br, H, Br CI H CH₂S(0)₂CH3 1.385 648,6

3-180 Br, H, Br Cl H Etilsulfonilmetil 1.414 662,6

3-181 CI, F, CI CI H (1,1-dioxothiolan-3-1,363 618,7yl)methyl

3-182 CI, F, CI CI H 2,2,2-Trifluoroethyl- 1,493 612,7 Sulfanylmethyl

3-183 CI, F, CI CI H Cyclobutylmethyl 1.521 554.7

3-184 CI, F, CI CI H (1,1-dioxothiethane-3-1,370 602,8yl)methyl

3-185 CI, F, CI CI H 3,3-difluorocyclobutyl 1.477 574.8

3-186 CI, F, CI CI H Vinyl 1,472 510.7

3-187 Br, H, Br Cl H n-Propil 1.525 599,0

3-188 OCF, H, H Cl H CH2CH3 1.383 510,8

3-189 OCF, H, H Cl H CH2CF3 1.415 564,8

3-190 OCF, H, H CI HCH 1.341 496,8

3-191 OCF, H, HCIHCH₂S(0)₂CH3 1.328 575,2

3-192 OCFs, H, H Cl H Etilsulfonilmetil 1.358 589,2

3-193 OCFs, H, H Cl H n-Propil 1.427 525,3

3-194 OCFs, H, H Cl H Ciclopropilo 1.407 523,3

3-195 CI, F, CI CI H 1,3-dioxolan-2-yl 1.429 558.6

3-196 CI, F, CI CI H 2,2,2-Trifluoroethyl- 1,469 644,7 Sulfonylmethyl

3-197 CI, F, CI CI H 2-Furylmethyl 1.481 566.6

3-198 CI, F, CI CI H 1-chlorocyclopropyl 1.573 560.7

3-199 CI, F, CI CI H Cyclopropylmethyl- 1.524 583.7 Carbamoyl

3-200 CI, F, CI CI H C (CH)₂KN 1.497 554,2

3-201 CI, F, CI CI H Cyclopropylmethyl 1,488 540.6

3-202 Br, H, CFs N0₂H CHs 1.368 571,6

3-203 Br, H, CFs N0₂HCH2CH3 1.409 585,7

3-204 Br, H, CFs N0₂H n-Propyl 1.443 599,7

3-205 Br, H, CFs N0₂H Cyclopropyl 1.426 597.7

3-206 Br, H, CFs N0₂HCH2CF3 1.438 639,6

3-207 Br, H, CFs N0₂HCH₂S(0)₂CH₃1.350 647,7 Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

3-208 Br, H, CFs N0₂H-Ethylsulfonylmethyl 1,377 663.6

3-209 CFs, F, H Cl H CH2CH3 1.374 512,9

3-210 CF, F, H Cl H CH2CF3 1.406 566,8

3-211 FC, F, H Cl H CH 1.383 499,2

3-212 CFs, F, H Cl H Ciclopropilo 1.392 524,8

3-213 CF, F, HCIHCH₂S(0)₂CH3 1.347 577,2

3-214 CFs, F, H Cl H Etilsulfonilmetil 1.375 591,2

3-215 CFs, F, H CI H n-Propil 1.410 526,9

3-216 Br, H, CFs CFs H CH2CH3 1.496 609,2

3-217 Br, H, CFs CFs H CH2CF3 1.518 663,1

3-218 Br, H, CFs CFs H CHs 1.456 595

3-219 Br, H, CFs CFs H Ciclopropilo 1.511 621

3-220 Br, H, CF CF HCH₂S(0)₂CH3 1.437 673.1

3-221 Br, H, CFs CFs H Etilsulfonilmetil 1.463 687,2

3-222 Br, H, CFs CFs H n-Propil 1.529 623,1

3-223 CI, H, CI F H CH2 CH3 1.393 478.8

3-224 CI, H, CI F H CH2CF3 H NMR (400 MHz,

CDCI): δ 7,7-7,3 (m, 6H), 6,9 (br. s, 1H), 4,5 (m, 2H), 4,2 (d, 1H), 3,8 ( d, 1H), 3,2-3,0 (m,

2H)

3-225 CI, H, CI F H Cyclopropyl 1,412 490.8

3-226 CI, H, CI FH CH₂S(0)₂CH₃RMN-H (400 MHz,

CDCI): δ 7,7–7,3 (m, 6H), 7,2 (br. s, 1H), 4,6 (m,2H), 4,2 (d, 1H), 3,95 ( s, 2H), 3,85 (d, 1H),

3,1 (s, 3H)

3-227 CI, H, CI F H Ethylsulfonylmethyl 1.360 556.8

3-228 CI, H, CI F H n-Propil 1,431 492.8

3-229 CI, H, CI FH CH 1349 464.8

3-230 I, H, CFs Cl H CHs 1.450 607,1

3-231 I, H, CFs CI H CH2CH3 1.490 621,1

3-232 I, H, CFs CI H n-Propil 1.496 634,7

3-233 I, H, CFs CI H Cyclopropyl 1,478 632.7

3-234 I, H, CFs C1 H CH₂S(0)₂CH3 1.482 685,2 Bsp. R^2a, R^2b, R^2cR⁴R⁵R⁸MS-HPLC:

an MRI

3-235 I, H, CFs Cl H Etilsulfonilmetil 1.455 699,1

3-236 I, H, CFs CI H CH2CF3 1.517 675,1

3-237 IC, IC, IC IC H CH2CF3 1.546 585,1

3-238 CI, CI, CIH CH 1.484 517.2

3-239 IC, IC, IC IC H CH2CH3 1.492 530,7

3-240 CI, CI, CI CI H n-Propil 1.527 544.7

3-241 CI, CI, CI CI H Cyclopropyl 1.509 542.7

3-242 CI, CI, CI CI H CH₂S(0)₂CH3 1.428 594,7

3-243 CI, CI, CI CI H Ethylsulfonylmethyl 1.456 608.7

3-244 CI, H, CI CI H terc-butoxy 1.605 485.4

3-245 OCF, H, Br Cl H CH2CF3 1.485 644,6

3-246 OCFs, H, Br Cl H CHs 1.423 576,7

3-247 OCFs, H, Br Cl H Ciclopropilo 1.510 603,2

3-248 OCF, H, BrCl H CH₂S(0)₂CH3 1.430 655.1

3-249 OCFs, H, Br Cl H Etilsulfonilmetil 1.457 669,1

3-250 OCFs, H, Br Cl H n-Propil 1.495 604,7

3-251 OCF, H, Br Cl H CH2CH3 1.491 591,1

3-252 OCF, H, IC IC H CH2 CH3 1.451 544.8

3-253 OCF, H, CI CI H CH₂FC₃1.475 598,8

3-254 OCF, H, CI CI H CH 1.423 530.8

3-255 OCFs, H, Cl Cl H Ciclopropilo 1.467 556,8

3-256 OCF, H, CICI HCH₂S(0)₂CH 1.388 608,7

3-257 OCFs, H, Cl Cl H Etilsulfonilmetil 1.414 622,8

3-258 OCF, H, CI CI H n-Propyl 1.484 558.8

3-259 CF, H, Br CH HCH₂FC₃1.441 608,6

3-260 CFs, H, Br CHs H CH2CH3 1.412 554,7

3-261 CFs, H, Br CHs H Ciclopropilo 1.429 566,6

3-262 CF, H, Br CH HCH₂S(0)₂CH 1.350 618,6

3-263 CFs, H, Br CHs H Etilsulfonilmetil 1.379 632,6

3-264 CFs, H, Br CHs H n-Propil 1.446 568,7

3-265 CF, H, BrCH HCH 1.357 540,7

compound example

Examples of compounds 4-1 to 4-9 correspond to compounds of formula C.4: in which R^2a, R^2b, R^2c, R⁴, R^7ay R. S.⁸each synthesized compound is defined in a row in Table C.4 below.

Table C.4

B. Biology The biological activity and potency of compounds employed in the methods of the present invention can be determined, e.g. in the next test.

B.1 Green soldier bug (Nezara viridula) The active ingredient was dissolved to the desired concentration in a 1:1 (vol.) mixture of distilled water:acetone. Surfactant (Kinetic HV) was added at 0.01% (v/v). The test solution was prepared on the day of use.

Soybean pods were placed in glass Petri dishes lined with moistened filter paper and inoculated with ten late instars of N. viridula to the third instar. Approximately 2 mL of solution is sprayed into each petri dish using a handheld nebulizer. Test sands were maintained at approximately 25°C. The percentage mortality was recorded after 5 days.

In this test, the compounds 1 -1 , 1 -2, 1 -3, 1 -4, 1 -5, 1 -6, 1 -7, 1 -8, 1 -9, 1 -1 1 , 1 -14 , 1-15, 1-16, 1-19, 1-20, 1-23, 1-24, 1-25, 1-26, 1-29, 1-30, 1-31, 1-33, 1 - 37, 2-13, 2-16, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-24, 2-25, 2-26, 2-27 , 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35, 2-36, 2-37, 2-38, 2-39, 2 - 40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-47, 2-48, 2-50, 2-51, 2-52, 2-53, 2-54 , 2-55, 2-56, 2-57,

2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-69, 2-70, 2- 71, 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-81, 2-82, 2-83, 2-84, 2-86, 2-87, 2-88, 2-89, 2-90, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3- 8, 3-9, 3-10, 3-1 1, 3-12, 3-13, 3-14, 3-15, 3-17, 3-18, 3-19, 3-20, 3-21 , 3-22, 3-23, 3-24, 3-25, 3-27, 3-28, 3-29, 3-30, 3-31, 3-32, 3-34, 3-35, 3 -37, 3-40, 3-44, 3-45, 3-46, 3-48, 3-49, 3-50, 3-51, 3-63, 3-64, 3-69, 3-70 , 3-73, 3-74, 3-75, 3-76, 3-78, 3-83, 3-85, 3-86, 3-89,

3-94, 3-96, 3-98, 3-99, 3-100, 3-101, 3-102, 3-103, 3-104, 3-105, 3-106, 3-107, 3- 109, 3-1 10, 3-1 1 1, 3-1 12, 3-1 14, 3-1 19, 3-122, 3-124, 3-125, 3-129, 3-130, 3- 131, 3-133, 3-134, 3-135, 3-136, 3-139, 3-140, 3-141, 3-142, 3-143, 3-144, 3-146, 3-147, 3-148, 3-149, 3-150, 3-151, 3-152, 3-153, 3-156, 3-157, 3-158, 3-159, 3-160, 3-161, 3- 162, 3-163, 3-165, 3-166, 3-167, 3-168, 3-169, 3-170, 3-171 and 3-172 at 500 ppm showed more than 75% mortality compared to untreated controls.

Also in this test the compounds 1-7, 1-11, 1-15, 1-16, 1-29, 1-33, 1-37, 2-13, 2-16, 2-18, 2-19, 2 -20, 2-21, 2-22, 2-23, 2-24, 2-25, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2- 32, 2-33, 2-34, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-47, 2 -48, 2-50, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-59, 2-60, 2-61, 2- 62, 2-63, 2-64, 2-65, 2-66, 2-72, 2-74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-81,

2-82, 2-83, 2-84, 2-86, 2-87, 2-88, 2-89, 2-90, 3-2, 3-3, 3-4, 3-5, 3- 6, 3-7, 3-10, 3-12, 3-13, 3-17,

3-18, 3-19, 3-24, 3-25, 3-27, 3-28, 3-29, 3-30, 3-31, 3-32, 3-34, 3-35, 3- 37, 3-44, 3-49, 3-63, 3-64, 3-69, 3-73, 3-74, 3-78, 3-98, 3-99, 3-100, 3-102, 3-103, 3-104, 3-105, 3-106, 3-107, 3-109, 3-110, 3-112, 3-119, 3-122, 3-129, 3-130, 3- 133, 3-134, 3-135, 3-139, 3-141, 3-142, 3-143, 3-144, 3-146, 3-147, 3-148, 3-149, 3-150, 3-151, 3-152, 3-156, 3-157, 3-158, 3-159, 3-160, 3-161, 3-162, 3-165, 3-167, 3-169 and 3- 171 at 100 ppm showed greater than 75% mortality compared to untreated controls. B.2 Neotropical brown bug (Euschistus heros)

The drug was dissolved to the desired concentration in a 1:1 (vol.) mixture of distilled water: acetone. Surfactant (Kinetic HV) was added at 0.01% (v/v). The test solution was prepared on the day of use.

Soybean pods were placed in microwavable plastic cups and inoculated with ten adult E. heroes. Using a handheld spray bottle, spray approximately 1 ml of solution into each cup, insects and food present. A source of water (cotton wick with water) was provided. Each treatment was repeated twice. Test sands were maintained at approximately 25°C. The percentage mortality was recorded after 5 days.

In this test, compounds 1-33, 2-13, 2-16, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-24, 2-26, 2 -27, 2-29, 2-30, 2-31, 2-32, 2-33, 2-48, 2-50, 2-54, 2-56, 2-61, 2-62, 2- 66, 2-72, 2-74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-82, 2-84, 2-86, 2-87, 3-19, 3-27, 3-28, 3-29, 3-31, 3-49, 3-69, 3-73, 3-74, 3-83,

3-102, 3-106, 3-107, 3-109, 3-110 and 3-135 at 100 ppm showed greater than 75% mortality compared to untreated controls. B.3 Brown variegated bug (Halyomorpha halys)

Raw peanut and soybean seeds were placed in microwavable plastic cups and inoculated with H. halys at five adult stages. Using a handheld spray bottle, spray approximately 1 ml of solution into each cup, insects and food present. A source of water (cotton wick with water) was provided. Each treatment is repeated 4 times. Test sands are maintained at approximately 25°C. The percentage mortality was recorded after 5 days.

(Video) Crop Systems Approach – Managing Soybeans to Maximize Yield

In this test, compounds 2-13, 2-16, 2-18, 2-19, 2-20, 2-21, 2-24, 2-25, 2-27, 2-30, 2-32, 2 -33, 2-34, 2-35, 2-38, 2-39, 2-40, 2-41, 2-42, 2-51, 2-52, 2-54, 2-55, 2- 56, 2-57, 2-59, 2-66, 2-72, 2-76, 2-77, 2-80, 2-81, 2-82, 2-84, 2-87, 3-19, 3-24, 3-27, 3-28, 3-29, 3-98, 3-104, 3-1 10, 3-1 12, 3-1 19 and 3-135 at 100 ppm showed more than 75% of mortality compared with untreated controls.

FAQs

What is the best pesticide for soyabean? ›

Baythroid^® XL. Bayer's Baythroid XL insecticide is the complete pyrethroid for many crops, and offers fast, effective control of pests in corn, soybeans, cotton and wheat.

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What is the mode of action of BASF intrepid? ›

Intrepid uses a novel mode of action (Molt Accelerating Compound) to specifically target lepidopterous pests while not adversely affecting beneficial insects, making it ideal for Integrated Pest Management systems.

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Are pesticides used on soybeans? ›

Pesticide Use

Among herbicides, glyphosate isopropylamine salt was the most widely used active ingredient (applied to 47 percent of planted acres), followed by glyphosate potassium salt (28 percent) (Table 2).

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What is the mode of action of Hexythiazox? ›

Specifically, hexythiazox is an ovicide whose mode of action is unknown but is used for the control of mite growth through activity on eggs or early stages of development.

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What do farmers spray on soybeans? ›

Conventional farmers spray glyphosate on genetically engineered corn, oats, soybeans and wheat before it is harvested.

How many times do you spray soybeans? ›

The best timing is R2 (full flower) to R3 (first pod) if you are only spraying one time. If you are after white mold, spray twice, about 2 weeks apart, starting immediately. Also, spraying Cobra will help reduce white mold issues, but spray that separate from fungicide.

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What are three modes of action for insecticides? ›

Mode of action of the major chemical classes of insecticides involves mainly three target sites in the nervous system: acetylcholinesterase, an enzyme of critical importance in the transmission of nerve impulse (organophosphorus and carbamates), voltage-gated sodium channels across the nerve membrane (pyrethoids and ...

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Buy Intrepid Insecticide Starting @₹448/- – BigHaat.com.

What are the major pest of soybean? ›

Major pests in soybeans are helicoverpa (heliothis), podsucking bugs, and potentially silverleaf whitefly. Other lesser and/or infrequent, but damaging pests, include loopers, grass blue butterfly, cluster caterpillar, soybean moth, soybean aphid, mirids, monolepta beetle and crickets.

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What are common pests with soybeans? ›

Miscellaneous Pests

Burrowing Bugs.
False Chinch Bugs.
Grasshoppers.
Pillbugs.
Spider Mites.
Stink Bug.

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What is the half life of Hexythiazox? ›

The elimination half-life was about 10 h at 10 mg/kg bw, and was prolonged to about 20 h at 880 mg/kg bw, presumably reflecting saturation. This was confirmed by data on excretion.

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What is the boiling point of Hexythiazox? ›

Boiling point/Boiling range:

81 °C (177.8 °F) · Flash point: 2 °C (35.6 °F) · Flammability (solid, gaseous): Not applicable.

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What chemical class is Hexythiazox? ›

belongs to the class of organic compounds known as chlorobenzenes.

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When should you spray soybeans? ›

Overall, for Roundup, Pursuit and Classic, spraying between 9 a.m. and 6 p.m. helps maximize weed control in soybean. If you're facing windy weather during those hours, Nurse advises monitoring the size of the weeds in the field.

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When should you not spray soybeans? ›

Most states say June 20 or June 30 for a cutoff. Typically, our advice is to spray before June 15, but whatever you do, make sure you find out the last spray date for your state and your situation.

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Should I spray fungicide on soybeans? ›

In soybean, fungicide applications are currently recommended for foliar diseases when soybean is at the R3 growth stage. This is called "beginning pod" and means that the pod is 3/16 inch long at one of the four uppermost nodes on the main stem with a fully developed leaf.

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How many gallons of fungicide per acre for soybeans? ›

It is recommended that ground applied fungicides be sprayed in a carrier vol ume of at least 15 gallons per acre.

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How late can you spray soybeans with glyphosate? ›

Glyphosate (Roundup Ready or glyphosate-resistant varieties only) - emergence through flowering. Can be used as a harvest aid at least 7 days before harvest and when soybean pods have set and have lost all green color and 80-90% of leaves have dropped.

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Can you spray soybeans when they are flowering? ›

Currently, glyphosate labels state that glyphosate can be applied from soybean cracking to “throughout flowering.” Throughout flowering is defined as the R2 soybean growth stage.

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What are the three initial of methods of controlling pests? ›

Plowing, crop rotation, removal of infected plant material, cleaning of greenhouse and tillage equipment, and effective manure management are all cultural practices that are employed to deprive pests of a comfortable habitat or prevent their spread.

Which of the following are the types of pest control methods? ›

4 Types of Pest Control

Chemical Pest Control. The chemical method involves uses chemical treatments to deter any kind of pest. ...
Biological Pest Control. Biological control involves the use of living organisms to control a pest population. ...
Electronic Pest Control. ...
Physical Pest Control.

Sep 7, 2017

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What are the 4 types of pesticides? ›

What are the types of pesticides? Insecticides, herbicides, rodenticides, and fungicides are examples of well-known pesticides.

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Is BASF SE a buy? ›

BASFY is currently sporting a Zacks Rank of #2 (Buy), as well as a Value grade of A. The stock holds a P/E ratio of 11.78, while its industry has an average P/E of 16.46. BASFY's Forward P/E has been as high as 12.01 and as low as 7.08, with a median of 9.11, all within the past year.

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Who is BASF owned by? ›

75% of the BASF shares are held by institutional investors (BlackRock more than 5%). 36% of the shares are held in Germany, 11% in the UK and 17% in the U.S.

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Why is BASF successful? ›

BASF becomes known for a strategy based on innovation and even wins a Nobel Prize. Application technology of BASF is founded in 1891 and involves more than mere contact with customers from the very beginning. Instead, it offers intensive support and advice which leads BASF to develop an explicit customer focus.

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Is BASF the largest chemical company in the world? ›

In 2018, sales of the top fifty companies amounted to US$951,000,000,000, an increase of 11.8% compared to the top fifty producers of 2017.
...
Top fifty producers by sales (2021)

Rank	1
Company	BASF
Chemical sales in 2018 USD millions	74,066
Change from 2017 in percent	2.4
Headquarters	Ludwigshafen, Germany

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What are the most important products of BASF? ›

The most important of the division's product groups include amines, diols, polyalcohols, acids and specialties.

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Is BASF the largest chemical company? ›

The German chemical company BASF was ranked number one in the ranking of the world's leading chemical companies based on revenue, generating a revenue of approximately 84.64 billion U.S. dollars in 2021.

Do farmers use pesticides on soybeans? ›

Today, U.S. farmers use more than twice as much herbicide to grow soybeans as they did before Roundup Ready crops were introduced.

How do you control aphids on soybeans? ›

Good insecticide coverage and penetration is required for optimal control of soybean aphid, as many aphids feed on the undersides of the leaves and within the canopy. Use high water volume and pressure. Aerial application works well when high water volume is used (5 gallons of water per acres recommended).

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How do you control pests in soybeans? ›

With IPM, pest management occurs from pre-plant to post-harvest and is prevention-based. This includes selecting disease-resistant or insect tolerant varieties, using cultural methods such as crop rotation; planting date; residue management, and good agronomic practices to encourage competitive crop growth.

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How do you control stem borer in soybeans? ›

Stem borer adults are attracted to a number of large stemmed weed species. Control of within field weeds such as sunflowers, ragweed, and cocklebur will reduce these alternate hosts and consequently the number of borers in the field. Another control method is to plant a trap crop of sunflowers next to a soybean field.

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What is the most common pest? ›

1. Ants. In California and all around the country, ants are considered to be one of the most common bugs found in homes by pest control companies. No matter whether you live in an apartment in the East Bay Area or own a home in the North Bay Area, you've likely dealt with an ant problem at some point.

What are three major pests of soybean? ›

Pests that destroy soybean leaves include whitefly ( Bemisia tabaci G.), aphids ( Aphis glycines ), red mites ( Tetranychus cinnabarinus ), soybean green leafhoppers ( Empoasca spp.), Armyworms ( S.

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How do you control wireworms in soybeans? ›

Management Guidelines

Replanted soybean may receive an equivalent level of wireworm damage as the original planting so if possible, plant a different crop and apply a wireworm- labeled soil insecticide. Seed treatments only protect the seed, not the seedling, therefore control may be variable with these products.

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Which fungicide is used in soybeans? ›

Contact fungicides used for soybean seed treatment include captan, fludioxonil, PCNB, and thiram. Systemic fungicides used for soybean seed treatment include azoxystrobin, caroboxin, mefenoxam, metalaxyl, trifloxystrobin, and thiabendazole.

What is the meaning of Hexythiazox? ›

EXPLANATION. Hexythiazox is a non-systemic insecticide and miticide first evaluated by the 1991 JMPR and a number of times subsequently. It was recently reviewed for toxicology by the 2008 JMPR within the periodic review program of the CCPR. An ADI of 0–0.03 mg/kg bw was established.

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What is the active ingredient in imidacloprid? ›

Imidacloprid is a systemic insecticide belonging to a class of chemicals called the neonicotinoids which act on the central nervous system of insects.
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Imidacloprid.

Names
IUPAC name N-{1-[(6-Chloro-3-pyridyl)methyl]-4,5-dihydroimidazol-2-yl}nitramide
Identifiers
CAS Number	138261-41-3
3D model (JSmol)	Interactive image

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Is Spinosad a pesticide? ›

It is a mixture of two chemicals called spinosyn A and spinosyn D. It is used to control a wide variety of pests. These include thrips, leafminers, spider mites, mosquitoes, ants, fruit flies and others. Spinosad has been registered for use in pesticides by the US Environmental Protection Agency (EPA) since 1997.

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Can water boil past100? ›

It seems like one of those basic science facts: Water boils at 212 degrees Fahrenheit (100 degrees Celsius), right? Well, not always. It depends on where you're doing the boiling. In fact, water will boil at about 202 degrees in Denver, due to the lower air pressure at such high elevations.

What temperature is high boil? ›

A liquid in a partial vacuum, i.e., under a lower pressure, has a lower boiling point than when that liquid is at atmospheric pressure. Because of this, water boils at 99.97 °C (211.95 °F) under standard pressure at sea level, but at 93.4 °C (200.1 °F) at 1,905 metres (6,250 ft) altitude.

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What is the boiling point of c18h38? ›

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density:	0.8±0.1 g/cm³
Boiling Point:	316.3±5.0 °C at 760 mmHg
Vapour Pressure:	0.0±0.3 mmHg at 25°C
Enthalpy of Vaporization:	53.5±0.8 kJ/mol
Flash Point:	165.6±0.0 °C

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Is triazine a chemical? ›

SHORT-TERM HEALTH HAZARDS - The triazine pesticides listed above are slightly to moderately poisonous compounds. - All these chemicals can be absorbed through the skin, especially through cuts and scratches, so direct contact should be avoided.

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What type of amine is dipropylamine? ›

Dipropylamine is a flammable, highly toxic, corrosive amine.

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Is thiamethoxam a chemical? ›

Thiamethoxam is a nicotinoid compound with broad-spectrum insecticidal properties. It is registered for use on numerous crops in many countries against sucking and chewing insects in vegetables, ornamentals, field crops, deciduous fruits, citrus, cotton and rice.

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What do farmers spray before planting soybeans? ›

For best results, apply soybean inoculant (not just a seed coating) to the seed just prior to planting. contains only Glyphosate and no other active ingredient. Roundup PowerMax and Weath- erMax are the best products; follow label directions.

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What can I spray soybeans to keep deer away? ›

Chemical repellents are one tool available to growers for controlling wildlife crop damage. Putrescent egg solids have been used successfully as a deer repellent and included as an active ingredient in several commercial repellent products.

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What stage do you spray fungicide on soybeans? ›

In soybean, fungicide applications are currently recommended for foliar diseases when soybean is at the R3 growth stage. This is called "beginning pod" and means that the pod is 3/16 inch long at one of the four uppermost nodes on the main stem with a fully developed leaf.

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Can I spray 24d on soybeans? ›

If you apply 2,4-D post to Xtend soybean it will severely injure or kill them, this same is true if you spray dicamba on E3 soybeans.

What is the best pre emergent for soybeans? ›

TriActor EZ is the best pre-emergent herbicide for IP soybeans providing triple action on a wide range of grass and broadleaf weeds. Fierce EZ is a liquid pre-emergent residual herbicide that offers extended activity on emerging spring broadleaf and grassy weeds for soybeans and wheat.

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Does it pay to spray fungicide on soybeans? ›

In trials where disease was present a fungicide application at the R3 stage resulted in an average yield gain of 1.8 bushels per acre.

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How do you keep weeds out of soybeans? ›

The most effective way to manage weeds in soybeans is to use an integrated weed-management program that includes crop rotation, good crop production practices, cultural weed-control practices, and a diversified herbicide program.

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Do they spray soybeans with Roundup? ›

With conventional tillage, it is recommended that glyphosate (Roundup PowerMax, Durango DMA, Touchdown Total, etc.) be applied to glyphosate-resistant soybeans 24 to 30 days after planting.

How do commercial farmers keep deer away? ›

Fencing. Fencing, the construction of a barrier between the crop and the deer, is the most effective long-term solution to deer damage. The basics of fencing apply to both electric and non-electric fencing. It is important to understand that deer can easily jump a fence 10 feet high, but much prefer not to.

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Will deer eat treated soybeans? ›

Deer and other wildlife will readily consume soybean forage, and depending on the native diet, may prove critical in supporting yearling deer growth.

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How late can I spray liberty on soybeans? ›

APPLICATION GUIDELINES

Apply Liberty at 32 fl oz/A over the top of LibertyLink soybeans from emergence to 14 days after crop emergence or when weeds are no more than 3 inches tall.

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