METHODS OF SOIL PEST CONTROL

The present invention relates to methods of soil pest control and in particular to control of corn rootworm, wireworms, grubs, in particular white grubs, termites, subterraneous stinkbugs, cutworms, millipedes and broca gigante.

Compounds that are insecticidally, acaricidally, nematicidally and/or moluscicidally active by antagnonism of the gamma-aminobutyric acid (GABA)-gated chloride channel, and which comprise a partially saturated heterocycle that is substituted by a haloalkyl substituent and one or two optionally substituted aromatic or heteroaromatic rings, represent a new class of pesticides that are described for example in Ozoe et al. Biochemical and Biophysical Research Communications, 391 (2010) 744-749. Compounds from this class are broadly described in WO 2005/085216 (EP1731512), WO 2007/123853, WO 2007/075459, WO2009/002809, WO 2008/019760, WO 2008/122375, WO 2008/128711, WO 2009/097992, WO 2010/072781, WO 2010/072781, WO 2008/126665, WO 2007/125984, WO

2008/130651, JP 2008110971, JP2008133273, JP2009108046, WO2009/022746, WO 2009/022746, WO 2010/032437, WO2009/080250, WO2010/020521, WO2010/025998, WO2010/020522,

WO2010/084067, WO2010/086225, WO2010/149506 and WO2010/108733.

It has now surprisingly been found that particular insecticides from this new class of gamma- aminobutyric acid (GABA)-gated chloride channel antagonists (disclosed in e.g. WO2009/080250, WO2010/020522, WO2010/149506, WO2011/101229 and WO2012/045700) are highly effective at controlling soil pests, in particular corn rootworm, wireworms, grubs, in particular white grubs, termites, subterraneous stinkbugs, cutworms, millipedes and broca gigante. The compounds of interest include a thietane amide derivative in which the thietane carbon ring members are unsubstituted. These compounds represent an important new solution for soil pests, particularly corn rootworm, wireworms, grubs, in particular white grubs, termites, subterraneous stinkbugs, cutworms, millipedes and broca gigante, and particularly where the soil pests are resistant to current methods.

In a first aspect the invention provides a method of controlling and/or preventing soil-dwelling pests in useful plants comprising applying to the locus of the useful plant or treating propagation material thereof, la I

wherein

cycle A is Ala or A2a

A1 a A2a

wherein A ¹ , A ² , A ³ and A ⁴ are independently C-H, or nitrogen and wherein #1 indicates the bond to X and #2 indicates the bond to cycle B;

cycle B is selected from Bl to B6

B1 B2 B3

wherein #1 indicates the bond to cycle A, #2 indicates the bond to R ⁷ and #3 indicates the bond to cycle C;

cycle C is phenyl;

R ⁵ is chloro, bromo, CF ₃ or methyl;

R ⁷ is chlorodifluoromethyl or trifluoromethyl;

each R ⁸ is independently bromo, chloro, fluoro or trifluoromethyl;

p is 1, 2 or 3; and

and X is selected from PI to P9

In a further aspect the invention provides use of a compound of formula I for the control of a soil- dwelling pest in useful plants.

Preferably the soil-dwelling pest is selected from corn rootworm, wireworms, grubs, in particular white grubs (e.g. Phyllophaga sp., Diloboderus sp., Popillia japonica), termites (in particular for sugar cane), subterraneous stinkbugs (e.g. Scaptocoris sp.) , cutworms (e.g. agrotis sp.), millipedes (e.g. Julus sp.) and broca gigante (e.g. Telchin licus).

In one embodiment the invention provides a method of controlling and/or preventing corn rootworm in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.

In one embodiment the invention provides a method of controlling and/or preventing wireworms in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.

In one embodiment the invention provides a method of controlling and/or preventing grubs, in particular white grubs, in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.

In one embodiment the invention provides a method of controlling and/or preventing

Phyllophaga sp. in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.

In one embodiment the invention provides a method of controlling and/or preventing

Diloboderus sp. in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.

In one embodiment the invention provides a method of controlling and/or preventing Popillia japonica in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.

In one embodiment the invention provides a method of controlling and/or preventing termites (in particular for sugar cane) in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.

In one embodiment the invention provides a method of controlling and/or preventing subterraneous stinkbugs (e.g. Scaptocoris sp.) in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.

In one embodiment the invention provides a method of controlling and/or preventing cutworms (e.g. agrotis sp.) in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.

In one embodiment the invention provides a method of controlling and/or preventing millipedes

(e.g. Julus sp.) in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I. In one embodiment the invention provides a method of controlling and/or preventing broca gigante (e.g. Telchin licus) in useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.

In a further aspect the invention provides a method of improving the growth of useful plants comprising applying to the locus of the useful plant or treating plant propagation material thereof, preferably a seed, with a compound of formula I.

In a further aspect the invention provides use of a compound of formula I as defined in claims 1 for improving the growth of useful plants.

In a further aspect the invention provides a method comprising applying a compound of formula I to the locus of corn plants by direct soil application. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably B 1 , cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4.

In a further aspect the invention provides a method of controlling and/or preventing corn rootworm in corn plants comprising applying a compound of formula I to the locus of corn plants by direct soil application. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably Bl, cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4.

In a further aspect the invention provides a method comprising applying a compound of formula I to the locus of corn plants by in-furrow application. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably Bl, cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4.

In a further aspect the invention provides a method of controlling and/or preventing corn rootworm in corn plants comprising applying a compound of formula I to the locus of corn plants by direct soil application. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably Bl, cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4.

In a further aspect the invention provides a method of controlling and/or preventing corn rootworm in corn plants comprising applying a compound of formula I to the locus of corn plants by in- furrow application. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably Bl, cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4.

In a further aspect the invention provides a method of controlling and/or preventing corn rootworm in useful plants comprising applying a compound of formula I to the locus of the useful plants by direct soil application. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably B 1 , cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4.

In a further aspect the invention provides a method of controlling and/or preventing corn rootworm in useful plants comprising applying a compound of formula I to the locus of the useful plants by in-furrow application. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably B 1 , cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4. In a further aspect the invention provides use of a compound of formula I for controlling and/or preventing corn rootworm in useful plants, preferably corn plants, by applying a compound of formula I to the locus of the useful plants directly to soil. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably B 1 , cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4.

In a further aspect the invention provides use of a compound of formula I for controlling and/or preventing corn rootworm in useful plants, preferably corn rootworm, by applying a compound of formula I to the locus of the useful plants and appliying the compound of formula I by in- furrow application. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably B 1 , cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4.

In a further aspect the invention provides a method comprising applying a compound of formula I to a field of corn plants, before, during or after planting, and wherein the application of the compound of formula I comprises applying the compound of formula I directly to soil. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably Bl, cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4.

In a further aspect the invention provides a method comprising applying a compound of formula I to a field of corn plants, before, during or after planting, and wherein the application of the compound of formula I comprises applying the compound of formula I by in-furrow application. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably Bl, cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4.

In a further aspect the invention provides a method of controlling and/or preventing corn rootworm in corn plants comprising applying a compound of formula I to a field of corn plants, before, during or after planting, and wherein the application of the compound of formula I comprises applying the compound of formula I directly to soil. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably B 1 , cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4.

In a further aspect the invention provides a method of controlling and/or preventing corn rootworm in corn plants comprising applying a compound of formula I to a field of corn plants, before, during or after planting, and wherein the application of the compound of formula I comprises applying the compound of formula I by in-furrow application. Prefered compounds are described below, most preferably cycle A is Ala, cycle B is Bl, or B2, preferably Bl, cycle C is phenyl, R ⁷ is trifluoromethyl and X is P2, P3 or P4.

Application before planning includes e.g. up to 1, 2, 3, 4, 5, or even up to 10 days before planting. Application after planting includes e.g. up to 1, 2, 3, 4, 5, or even up to 10 days after planting. For example application may be up to 10 days before or after planting, preferably up to 5 days before or after planting, more preferably up to up to 2 days before or after planting, most preferably up to 1 day before or after planting. Seed treatment is an example of indirect application to soil, e.g. the application of the compound of formula I by direct soil application comprises applying the compound of formula I to the soil other than via seed treatment.

In a further aspect, the invention provides a method for obtaining regulatory approval for the use of one or more of a compound of formula I to control a pest selected from corn rootworm, wireworms, grubs, in particular white grubs, termites, subterraneous stinkbugs, cutworms, millipedes and broca gigante, comprising at least one step of referring to, submitting or relying on biological data showing that said active ingredient reduces insect pressure.

The compounds of the invention may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds. The compounds of the invention may contain one or more asymmetric carbon atoms, for example, at the C(#2)#3 group, and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such. Reference to compounds of the invention also includes reference to salts and N-oxides.

Preferred values of cycle A, cycle B, cycle C, X, p, A ¹ , A ² , A ³ , A ⁴ , R ⁵ , R ⁷ and R ⁸ in compounds of formula I are, in any combination, as set out below.

Preferably cycle A is Ala.

Preferably cycle B is a cycle selected from cycle Bl, B2 and B3, more preferably cycle Bl or B2, most preferably cycle B 1.

In one group of compounds cycle B is Bl . In another group of compounds cycle B is B2. In another group of compounds cycle B is B3. In another group of compounds cycle B is B4. In another group of compounds cycle B is B5. In another group of compounds cycle B is B6.

cycle C is cycle CI

C1

More preferably cycle C is 3,5-dichlorophenyl-, 3-chloro-4-fluorophenyl-, 3-fluoro-4- chlorophenyl-, 3,4-dichlorophenyl-, 3-chloro-4-bromophenyl-, 3,5-dichloro-4-fluorophenyl-, 3,4,5- trichlorophenyl-, 3,5-dichloro-4-iodophenyl-, 3,4,5-trifluorophenyl-, 3-chloro-5-bromophenyl-, 3-chloro- 5-fluorophenyl-, 3-chloro-5-(trifluoromethyl)phenyl-, 3,4-dichloro-5-(trifluoromethyl)phenyl-, 3,5- bis(trifluoromethyl)phenyl-, 4-chloro-3,5-bis(trifluoromethyl)phenyl-, 3-(trifluoromethyl)phenyl-, more preferably 3-chloro-5-bromophenyl-, 3-chloro-5-(trifluoromethyl)phenyl-, 3,5-dichloro-4-fluorophenyl-, 3 ,4,5-trichlorophenyl-, 3 ,5 -bis(trifluoromethyl)phenyl-, 3 -(trifluoromethyl)phenyl-, 3 ,5 -dichloro-4- bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-, most preferably 3,5-dichloro-phenyl.

Preferably A ¹ is C-H or C-R ⁵ , most preferably A ¹ is C-H.

Preferably A ² is C-H or C-R ⁵ , most preferably A ² is C-H. Preferably A ³ is C-H or C-R ⁵ , most preferably A ³ is C-H.

Preferably A ⁴ is C-H or C-R ⁵ , most preferably A ⁴ is C-H.

Preferably no more than one of A ¹ and A ² is nitrogen. Preferably no more than one of A ³ and A ⁴ is nitrogen. Preferably A ¹ and A ² are both C-H. Preferably both A ³ and A ⁴ are C-H.

Preferably R ⁵ is methyl or chloro, most preferably methyl.

Preferably R ⁷ is trifiuoromethyl.

Preferably each R ⁸ is independently fluoro, bromo or chloro.

Preferably p is 2 or 3, most preferably 2.

Preferably X is P2, P3 or P4.

In one group of compounds cycle A is Ala, cycle B is Bl, B2 or B3, cycle C is phenyl.

In one group of compounds cycle A is Ala, cycle B is Bl, B2 or B3, cycle C is phenyl, R ⁷ is trifiuoromethyl.

In one group of compounds cycle A is Ala, cycle B is Bl, B2 or B3, cycle C is phenyl, R ⁷ is trifiuoromethyl and X is P2, P3 or P4.

In one group of compounds cycle A is Ala, cycle B is Bl, cycle C is phenyl, R ⁷ is trifiuoromethyl and X is P2, P3 or P4.

In one group of compounds cycle A is Ala, cycle B is B2, cycle C is phenyl, R ⁷ is trifiuoromethyl and X is P2, P3 or P4.

In one group of compounds cycle A is Ala, cycle B is B3, cycle C is phenyl, R ⁷ is trifiuoromethyl and X is P2, P3 or P4.

The following tables illustrate specific compounds of the invention:

Table 1

Table 1 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-CH, Cycle B is B 1 and R7 is trifiuoromethyl, and cycle C and X are as defined in Table P.

Table 2

Table 2 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-CH, Cycle B is B 1 and R7 is trifiuoromethyl, and cycle C and X are as defined in Table P.

Table 3

Table 3 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are N-CH, Cycle B is B 1 and R7 is trifiuoromethyl, and cycle C and X are as defined in Table P.

Table 4

Table 4 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are N-CH, Cycle B is B 1 and R7 is trifiuoromethyl, and cycle C and X are as defined in Table P.

Table 5

Table 5 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-N, Cycle B is B 1 and R7 is trifiuoromethyl, and cycle C and X are as defined in Table P.

Table 6

Table 6 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-N, Cycle B is B 1 and R7 is trifiuoromethyl, and cycle C and X are as defined in Table P.

Table 7

Table 7 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-CH, Cycle B is B2 and R7 is trifiuoromethyl, and cycle C and X are as defined in Table P. Table 8

Table 8 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-CH, Cycle B is B2 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P. Table 9

Table 9 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are N-CH, Cycle B is B2 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 10

Table 10 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are N-CH, Cycle B is B2 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 11

Table 11 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-N, Cycle B is B2 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 12

Table 12 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-N, Cycle B is B2 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 13

Table 13 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-CH, Cycle B is B3 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 14

Table 14 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-CH, Cycle B is B3 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 15

Table 15 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are N-CH, Cycle B is B3 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 16

Table 16 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are N-CH, Cycle B is B3 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 17

Table 17 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-N, Cycle B is B3 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 18

Table 18 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-N, Cycle B is B3 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 19

Table 19 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-CH, Cycle B is B4 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P. Table 20

Table 20 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-CH, Cycle B is B4 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P. Table 21

Table 21 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are N-CH, Cycle B is B4 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 22

Table 22 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are N-CH, Cycle B is B4 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 23

Table 23 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-N, Cycle B is B4 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 24

Table 24 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-N, Cycle B is B4 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 25 Table 25 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-CH, Cycle B is B5 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 26

Table 26 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-CH, Cycle B is B5 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 27

Table 27 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are N-CH, Cycle B is B5 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 28

Table 28 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are N-CH, Cycle B is B5 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 29

Table 29 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-N, Cycle B is B5 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 30

Table 30 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-N, Cycle B is B5 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 31

Table 31 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-CH, Cycle B is B6 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P. Table 32

Table 32 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-CH, Cycle B is B6 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P. Table 33

Table 33 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are N-CH, Cycle B is B6 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 34

Table 34 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are N-CH, Cycle B is B6 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 35

Table 35 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is methyl, Al and A2 are CH-N, Cycle B is B6 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 36

Table 36 provides 338 compounds of Formula I wherein cycle A is cycle Ala, R5 is chloro, Al and A2 are CH-N, Cycle B is B6 and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 37

Table 37 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B 1 , and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 38

Table 38 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B 1 , and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 39

Table 39 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B 1 , and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 40

Table 40 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B2, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 41

Table 41 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B2, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 42

Table 42 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B2, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P. Table 43

Table 43 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B3, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 44

Table 44 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B3, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 45

Table 45 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B3, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 46

Table 46 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B4, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 47

Table 47 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B4, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 48

Table 48 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B4, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 49

Table 49 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B5, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 50

Table 50 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B5, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 51

Table 51 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B5, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 52

Table 52 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B6, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 53

Table 53 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B6, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 54

Table 54 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B6, and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table P

Cycle C X Stereochemistry

1 3,5-dichloro-phenyl- PI _j **

2 3,4,5 -trichloro-phenyl- PI _j **

3 3,5-dichloro-4-fluoro-phenyl- PI _j **

4 3-chloro-4-fluoro-phenyl- PI _j **

5 3,4-dichloro-phenyl- PI _j **

6 3 ,5 -dichloro-4-bromo -phenyl - PI _j **

7 3,4,5-trifluoro-phenyl- PI _j **

8 3-chloro-5-bromo-phenyl- PI _j **

9 3-chloro-5-trifluoromethyl-phenyl- PI _j **

10 3-chloro-4-chloro-5-trifluoromethyl-phenyl- PI 3 ,5 -di-trifluoromethyl-phenyl- Pl _j **

3 ,5 -di-trifluoromethyl-4-chloro-phenyl- PI _j **

3 -trifluoromethyl-phenyl- PI _j **

3,5-dichloro-phenyl- P2 _j **

3,4,5 -trichloro-phenyl- P2 _j **

3,5-dichloro-4-fluoro-phenyl- P2 _j **

3 -chloro-4-fluoro-phenyl- P2 _j **

3,4-dichloro-phenyl- P2 _j **

3 ,5 -dichloro-4-bromo -phenyl - P2 _j **

3,4,5 rifluoro-phenyl- P2 _j **

3-chloro-5-bromo-phenyl- P2 _j **

3-chloro-5-trifluoromethyl-phenyl- P2 _j **

3-chloro-4-chloro-5-trifluoromethyl-phenyl- P2 _j **

3 ,5 -di-trifluoromethyl-phenyl- P2 _j **

3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P2 _j **

3 -trifluoromethyl-phenyl- P2 _j **

3,5-dichloro-phenyl- P3 _j **

3,4,5 -trichloro-phenyl- P3 _j **

3,5-dichloro-4-fluoro-phenyl- P3 _j **

3 -chloro-4-fluoro-phenyl- P3 _j **

3,4-dichloro-phenyl- P3 _j **

3 ,5 -dichloro-4-bromo -phenyl - P3 _j **

3,4,5 rifluoro-phenyl- P3 _j **

3-chloro-5-bromo-phenyl- P3 _j **

3-chloro-5-trifluoromethyl-phenyl- P3 _j **

3-chloro-4-chloro-5-trifluoromethyl-phenyl- P3 _j **

3 ,5 -di-trifluoromethyl-phenyl- P3 _j **

3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P3 _j **

3 -trifluoromethyl-phenyl- P3 _j **

3,5-dichloro-phenyl- P3 (cis) _j **

3,4,5 -trichloro-phenyl- P3 (cis) _j **

3,5-dichloro-4-fluoro-phenyl- P3 (cis) _j **

3 -chloro-4-fluoro-phenyl- P3 (cis) _j **

3,4-dichloro-phenyl- P3 (cis) _j **

3 ,5 -dichloro-4-bromo -phenyl- P3 (cis) _j **

3,4,5-trifluoro-phenyl- P3 (cis) _j **

3-chloro-5-bromo-phenyl- P3 (cis) _j **

3-chloro-5-trifluoromethyl-phenyl- P3 (cis) _j **

3-chloro-4-chloro-5-trifluoromethyl-phenyl- P3 (cis) _j **

3 ,5 -di-trifluoromethyl-phenyl- P3 (cis) _j **

3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P3 (cis) _j **

3 -trifluoromethyl-phenyl- P3 (cis) _j **

3,5-dichloro-phenyl- P3 (trans) _j **

3,4,5 -trichloro-phenyl- P3 (trans) _j **

3,5-dichloro-4-fluoro-phenyl- P3 (trans) 3 -chloro-4-fluoro-phenyl- P3 (trans) _j **

3,4-dichloro-phenyl- P3 (trans) _j **

3 ,5 -dichloro-4-bromo -phenyl - P3 (trans) _j **

3,4,5 rifluoro-phenyl- P3 (trans) _j **

3-chloro-5-bromo-phenyl- P3 (trans) _j **

3-chloro-5-trifluoromethyl-phenyl- P3 (trans) _j **

3-chloro-4-chloro-5-trifluoromethyl-phenyl- P3 (trans) _j **

3 ,5 -di-trifluoromethyl-phenyl- P3 (trans) _j **

3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P3 (trans) _j **

3 -trifluoromethyl-phenyl- P3 (trans) _j **

3,5-dichloro-phenyl- P4 _j **

3,4,5 -trichloro-phenyl- P4 _j **

3,5-dichloro-4-fluoro-phenyl- P4 _j **

3 -chloro-4-fluoro-phenyl- P4 _j **

3,4-dichloro-phenyl- P4 _j **

3 ,5 -dichloro-4-bromo -phenyl - P4 _j **

3,4,5 rifluoro-phenyl- P4 _j **

3-chloro-5-bromo-phenyl- P4 _j **

3-chloro-5-trifluoromethyl-phenyl- P4 _j **

3-chloro-4-chloro-5-trifluoromethyl-phenyl- P4 _j **

3 ,5 -di-trifluoromethyl-phenyl- P4 _j **

3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P4 _j **

3 -trifluoromethyl-phenyl- P4 _j **

3,5-dichloro-phenyl- P5 _j **

3,4,5 -trichloro-phenyl- P5 _j **

3,5-dichloro-4-fluoro-phenyl- P5 _j **

3-chloro-4-fluoro-phenyl- P5 _j **

3,4-dichloro-phenyl- P5 _j **

3 ,5 -dichloro-4-bromo -phenyl- P5 _j **

3,4,5-trifluoro-phenyl- P5 _j **

3-chloro-5-bromo-phenyl- P5 _j **

3-chloro-5-trifluoromethyl-phenyl- P5 _j **

3-chloro-4-chloro-5-trifluoromethyl-phenyl- P5 _j **

3 ,5 -di-trifluoromethyl-phenyl- P5 _j **

3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P5 _j **

3 -trifluoromethyl-phenyl- P5 _j **

3,5-dichloro-phenyl- P6 _j **

3,4,5 -trichloro-phenyl- P6 _j **

3,5-dichloro-4-fluoro-phenyl- P6 _j **

3 -chloro-4-fluoro-phenyl- P6 _j **

3,4-dichloro-phenyl- P6 _j **

3 ,5 -dichloro-4-bromo -phenyl- P6 _j **

3,4,5-trifluoro-phenyl- P6 _j **

3-chloro-5-bromo-phenyl- P6 _j **

3-chloro-5-trifluoromethyl-phenyl- P6 _j **

3-chloro-4-chloro-5-trifluoromethyl-phenyl- P6 102 3 ,5 -di-trifluoromethyl-phenyl- P6 _j **

103 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P6 _j **

104 3 -trifluoromethyl-phenyl- P6 _j **

105 3 ,5 -dichloro-phenyl- P7 _j **

106 3,4,5 -trichloro-phenyl- P7 _j **

107 3,5-dichloro-4-fluoro-phenyl- P7 _j **

108 3 -chloro-4-fluoro-phenyl- P7 _j **

109 3,4-dichloro-phenyl- P7 _j **

110 3 ,5 -dichloro-4-bromo -phenyl - P7 _j **

111 3,4,5-trifluorc>-phenyl- P7 _j **

112 3-chloro-5-bromo-phenyl- P7 _j **

113 3-chloro-5-trifluoromethyl-phenyl- P7 _j **

114 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P7 _j **

115 3 ,5 -di-trifluoromethyl-phenyl- P7 _j **

116 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P7 _j **

117 3 -trifluoromethyl-phenyl- P7 _j **

118 3 ,5 -dichloro-phenyl- P8 _j **

119 3,4,5 -trichloro-phenyl- P8 _j **

120 3,5-dichloro-4-fluoro-phenyl- P8 _j **

121 3 -chloro-4-fluoro-phenyl- P8 _j **

122 3,4-dichloro-phenyl- P8 _j **

123 3 ,5 -dichloro-4-bromo -phenyl - P8 _j **

124 3,4,5-trifluorc>-phenyl- P8 _j **

125 3-chloro-5-bromo-phenyl- P8 _j **

126 3-chloro-5-trifluoromethyl-phenyl- P8 _j **

127 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P8 _j **

128 3 ,5 -di-trifluoromethyl-phenyl- P8 _j **

129 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P8 _j **

130 3 -trifluoromethyl-phenyl- P8 _j **

131 3 ,5 -dichloro-phenyl- P9 _j **

132 3,4,5 -trichloro-phenyl- P9 _j **

133 3,5-dichloro-4-fluoro-phenyl- P9 _j **

134 3-chloro-4-fluoro-phenyl- P9 _j **

135 3,4-dichloro-phenyl- P9 _j **

136 3 ,5 -dichloro-4-bromo -phenyl- P9 _j **

137 3,4,5-trifluoro-phenyl- P9 _j **

138 3-chloro-5-bromo-phenyl- P9 _j **

139 3-chloro-5-trifluoromethyl-phenyl- P9 _j **

140 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P9 _j **

141 3 ,5 -di-trifluoromethyl-phenyl- P9 _j **

142 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P9 _j **

143 3 -trifluoromethyl-phenyl- P9 _j **

144 3,5-dichloro-phenyl- P9 (cis) _j **

145 3,4,5 -trichloro-phenyl- P9 (cis) _j **

146 3,5-dichloro-4-fluoro-phenyl- P9 (cis) _j **

147 3 -chloro-4-fluoro-phenyl- P9 (cis) 148 3,4-dichloro-phenyl- P9 (cis) _j **

149 3 ,5 -dichloro-4-bromo -phenyl - P9 (cis) _j **

150 3,4,5 rifluoro-phenyl- P9 (cis) _j **

151 3-chloro-5-bromo-phenyl- P9 (cis) _j **

152 3-chloro-5-trifluoromethyl-phenyl- P9 (cis) _j **

153 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P9 (cis) _j **

154 3 ,5 -di-trifluoromethyl-phenyl- P9 (cis) _j **

155 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P9 (cis) _j **

156 3 -trifluoromethyl-phenyl- P9 (cis) _j **

157 3,5-dichloro-phenyl- P9 (trans) _j **

158 3,4,5 -trichloro-phenyl- P9 (trans) _j **

159 3,5-dichloro-4-fluoro-phenyl- P9 (trans) _j **

160 3 -chloro-4-fluoro-phenyl- P9 (trans) _j **

161 3,4-dichloro-phenyl- P9 (trans) _j **

162 3 ,5 -dichloro-4-bromo -phenyl - P9 (trans) _j **

163 3,4,5 rifluoro-phenyl- P9 (trans) _j **

164 3-chloro-5-bromo-phenyl- P9 (trans) _j **

165 3-chloro-5-trifluoromethyl-phenyl- P9 (trans) _j **

166 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P9 (trans) _j **

167 3 ,5 -di-trifluoromethyl-phenyl- P9 (trans) _j **

168 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P9 (trans) _j **

169 3 -trifluoromethyl-phenyl- P9 (trans)

170 3,5-dichloro-phenyl- PI

171 3,4,5 -trichloro-phenyl- PI

172 3,5-dichloro-4-fluoro-phenyl- PI

173 3-chloro-4-fluoro-phenyl- PI

174 3,4-dichloro-phenyl- PI

175 3 ,5 -dichloro-4-bromo -phenyl- PI

176 3,4,5-trifluoro-phenyl- PI

177 3-chloro-5-bromo-phenyl- PI

178 3-chloro-5-trifluoromethyl-phenyl- PI

179 3-chloro-4-chloro-5-trifluoromethyl-phenyl- PI

180 3 ,5 -di-trifluoromethyl-phenyl- PI

181 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- PI

182 3 -trifluoromethyl-phenyl- PI

183 3 ,5 -dichloro-phenyl- P2

184 3,4,5 -trichloro-phenyl- P2

185 3,5-dichloro-4-fluoro-phenyl- P2

186 3-chloro-4-fluoro-phenyl- P2

187 3,4-dichloro-phenyl- P2

188 3 ,5 -dichloro-4-bromo -phenyl- P2

189 3,4,5-trifluoro-phenyl- P2

190 3-chloro-5-bromo-phenyl- P2

191 3-chloro-5-trifluoromethyl-phenyl- P2

192 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P2

193 3 ,5 -di-trifluoromethyl-phenyl- P2 194 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P2

195 3 -trifluoromethyl-phenyl- P2

196 3,5-dichloro-phenyl- P3

197 3,4,5 -trichloro-phenyl- P3

198 3,5-dichloro-4-fluoro-phenyl- P3

199 3 -chloro-4-fluoro-phenyl- P3

200 3,4-dichloro-phenyl- P3

201 3 ,5 -dichloro-4-bromo -phenyl - P3

202 3,4,5 rifluoro-phenyl- P3

203 3-chloro-5-bromo-phenyl- P3

204 3-chloro-5-trifluoromethyl-phenyl- P3

205 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P3

206 3 ,5 -di-trifluoromethyl-phenyl- P3

207 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P3

208 3 -trifluoromethyl-phenyl- P3

209 3,5-dichloro-phenyl- P3 (cis)

210 3,4,5 -trichloro-phenyl- P3 (cis)

211 3,5-dichloro-4-fluoro-phenyl- P3 (cis)

212 3-chloro-4-fluoro-phenyl- P3 (cis)

213 3,4-dichloro-phenyl- P3 (cis)

214 3 ,5 -dichloro-4-bromo -phenyl - P3 (cis)

215 3,4,5-trifluoro-phenyl- P3 (cis)

216 3-chloro-5-bromo-phenyl- P3 (cis)

217 3-chloro-5-trifluoromethyl-phenyl- P3 (cis)

218 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P3 (cis)

219 3 ,5 -di-trifluoromethyl-phenyl- P3 (cis)

220 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P3 (cis)

221 3 -trifluoromethyl-phenyl- P3 (cis)

222 3,5-dichloro-phenyl- P3 (trans)

223 3,4,5 -trichloro-phenyl- P3 (trans)

224 3,5-dichloro-4-fluoro-phenyl- P3 (trans)

225 3-chloro-4-fluoro-phenyl- P3 (trans)

226 3,4-dichloro-phenyl- P3 (trans)

227 3 ,5 -dichloro-4-bromo -phenyl- P3 (trans)

228 3,4,5-trifluoro-phenyl- P3 (trans)

229 3-chloro-5-bromo-phenyl- P3 (trans)

230 3-chloro-5-trifluoromethyl-phenyl- P3 (trans)

231 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P3 (trans)

232 3 ,5 -di-trifluoromethyl-phenyl- P3 (trans)

233 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P3 (trans)

234 3 -trifluoromethyl-phenyl- P3 (trans)

235 3 ,5 -dichloro-phenyl- P4

236 3,4,5 -trichloro-phenyl- P4

237 3,5-dichloro-4-fluoro-phenyl- P4

238 3-chloro-4-fluoro-phenyl- P4

239 3,4-dichloro-phenyl- P4 240 3 ,5 -dichloro-4-bromo -phenyl - P4

241 3,4,5-trifluorc>-phenyl- P4

242 3-chloro-5-bromo-phenyl- P4

243 3-chloro-5-trifluoromethyl-phenyl- P4

244 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P4

245 3 ,5 -di-trifluoromethyl-phenyl- P4

246 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P4

247 3 -trifluoromethyl-phenyl- P4

248 3 ,5 -dichloro-phenyl- P5

249 3,4,5 -trichloro-phenyl- P5

250 3,5-dichloro-4-fluoro-phenyl- P5

251 3 -chloro-4-fluoro-phenyl- P5

252 3,4-dichloro-phenyl- P5

253 3 ,5 -dichloro-4-bromo -phenyl - P5

254 3,4,5-trifluorc>-phenyl- P5

255 3-chloro-5-bromo-phenyl- P5

256 3-chloro-5-trifluoromethyl-phenyl- P5

257 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P5

258 3 ,5 -di-trifluoromethyl-phenyl- P5

259 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P5

260 3 -trifluoromethyl-phenyl- P5

261 3 ,5 -dichloro-phenyl- P6

262 3,4,5 -trichloro-phenyl- P6

263 3,5-dichloro-4-fluoro-phenyl- P6

264 3-chloro-4-fluoro-phenyl- P6

265 3,4-dichloro-phenyl- P6

266 3 ,5 -dichloro-4-bromo -phenyl- P6

267 3,4,5-trifluoro-phenyl- P6

268 3-chloro-5-bromo-phenyl- P6

269 3-chloro-5-trifluoromethyl-phenyl- P6

270 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P6

271 3 ,5 -di-trifluoromethyl-phenyl- P6

272 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P6

273 3 -trifluoromethyl-phenyl- P6

274 3,5-dichloro-phenyl- P7

275 3,4,5 -trichloro-phenyl- P7

276 3,5-dichloro-4-fluoro-phenyl- P7

277 3 -chloro-4-fluoro-phenyl- P7

278 3,4-dichloro-phenyl- P7

279 3 ,5 -dichloro-4-bromo -phenyl- P7

280 3,4,5-trifluoro-phenyl- P7

281 3-chloro-5-bromo-phenyl- P7

282 3-chloro-5-trifluoromethyl-phenyl- P7

283 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P7

284 3 ,5 -di-trifluoromethyl-phenyl- P7

285 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P7 286 3 -trifluoromethyl-phenyl- P7

287 3,5-dichloro-phenyl- P8

288 3,4,5 -trichloro-phenyl- P8

289 3,5-dichloro-4-fluoro-phenyl- P8

290 3 -chloro-4-fluoro-phenyl- P8

291 3,4-dichloro-phenyl- P8

292 3 ,5 -dichloro-4-bromo -phenyl - P8

293 3,4,5 rifluoro-phenyl- P8

294 3-chloro-5-bromo-phenyl- P8

295 3-chloro-5-trifluoromethyl-phenyl- P8

296 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P8

297 3 ,5 -di-trifluoromethyl-phenyl- P8

298 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P8

299 3 -trifluoromethyl-phenyl- P8

300 3,5-dichloro-phenyl- P9

301 3,4,5 -trichloro-phenyl- P9

302 3,5-dichloro-4-fluoro-phenyl- P9

303 3 -chloro-4-fluoro-phenyl- P9

304 3,4-dichloro-phenyl- P9

305 3 ,5 -dichloro-4-bromo -phenyl - P9

306 3,4,5 rifluoro-phenyl- P9

307 3-chloro-5-bromo-phenyl- P9

308 3-chloro-5-trifluoromethyl-phenyl- P9

309 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P9

310 3 ,5 -di-trifluoromethyl-phenyl- P9

311 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P9

312 3 -trifluoromethyl-phenyl- P9

313 3,5-dichloro-phenyl- P9 (cis)

314 3,4,5 -trichloro-phenyl- P9 (cis)

315 3,5-dichloro-4-fluoro-phenyl- P9 (cis)

316 3-chloro-4-fluoro-phenyl- P9 (cis)

317 3,4-dichloro-phenyl- P9 (cis)

318 3 ,5 -dichloro-4-bromo -phenyl- P9 (cis)

319 3,4,5-trifluoro-phenyl- P9 (cis)

320 3-chloro-5-bromo-phenyl- P9 (cis)

321 3-chloro-5-trifluoromethyl-phenyl- P9 (cis)

322 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P9 (cis)

323 3 ,5 -di-trifluoromethyl-phenyl- P9 (cis)

324 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P9 (cis)

325 3 -trifluoromethyl-phenyl- P9 (cis)

326 3 ,5 -dichloro-phenyl- P9 (trans)

327 3,4,5 -trichloro-phenyl- P9 (trans)

328 3,5-dichloro-4-fluoro-phenyl- P9 (trans)

329 3-chloro-4-fluoro-phenyl- P9 (trans)

330 3,4-dichloro-phenyl- P9 (trans)

331 3 ,5 -dichloro-4-bromo -phenyl- P9 (trans) 332 3,4,5-trifluoro-phenyl- P9 (trans)

333 3-chloro-5-bromo-phenyl- P9 (trans)

334 3-chloro-5-trifluoromethyl-phenyl- P9 (trans)

335 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P9 (trans)

336 3 ,5 -di-trifluoromethyl-phenyl- P9 (trans)

337 3 ,5 -di-trifluoromethyl-4-chloro-phenyl- P9 (trans)

338 3 -trifluoromethyl-phenyl- P9 (trans)

I* * refers to compounds of formula Γ

In one embodiment the compound of formula I is a compound selected from Tables 1 to 54.

Compounds of formula I where cycle B is selected from Bl to B6 include at least one chiral centre and may exist as compounds of formula I* (IA*, IB*, IC*, ID*, IE*, IF*) or compounds of formula I** (IA**, IB**, IC**, ID**, IE**, IF**).

(IB ^* ) (IB ^** )

(IF ^* ) (IF ^** )

The compounds of formula I** are more biologically active than the respective compounds of formula I*. The invention includes mixtures of compounds I* and I** in any ratio e.g. in a molar ratio of 1 :99 to 99: 1, e.g. 10: 1 to 1 : 10, e.g. a substantially 50:50 molar ratio. In an enantiomerically (or epimerically) enriched mixture of formula I**, the molar proportion of compound I** compared to the total amount of both enantiomers is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%. Likewise, in enantiomerically (or epimerically) enriched mixture of formula II*, the molar proportion of the compound of formula II* compared to the total amount of both enantiomers (or epimerically) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%. Enantiomerically (or epimerically) enriched mixtures of formula I** are preferred.

Each compound disclosed in Tables 1 to 54 represents a specific disclosure of the isomer according to the compound of formula I* and the isomer according to the compound of formula I**, as indicated in the Tables as well as mixtures enriched for the compound according to the compound of formula I*, and mixtures enriched for the compound according to the compound of formula I**, as described above.

The term "soil-dwelling pest" refers to a pest that causes plant damage whilst in a life cycle phase that lives in the soil, and for example, damages plant roots. Examples of specific pests are described below. Soil dwelling pests may be insects, acarines and/or nematodes, preferably insects, or acarines, most preferably insects.

The compounds of formula I may be prepared using the information provided in

e.g.WO2009/080250, WO2010/020522, WO2010/149506, WO2011/101229 and WO2012/045700. WO2011/104089 and WO2011/154555 describe enantioselective routes to the compounds of formula I. The compounds in Scheme 1 may be prepared according to the methods described in WO2011/104089.

Scheme 1

Table Q provides 792 preferred substituent combinations for the compounds illustrated in Scheme 1 Table 0

R8a R8b R8c R5 L R8a R8b R8c R5 L

1 Br H H CH3 - 397 Br H H CH3 CH2

2 CI H H CH3 - 398 CI H H CH3 CH2

3 F H H CH3 - 399 F H H CH3 CH2

4 CF3 H H CH3 - 400 CF3 H H CH3 CH2

5 H Br H CH3 - 401 H Br H CH3 CH2

6 Br Br H CH3 - 402 Br Br H CH3 CH2

7 CI Br H CH3 - 403 CI Br H CH3 CH2

8 F Br H CH3 - 404 F Br H CH3 CH2

9 CF3 Br H CH3 - 405 CF3 Br H CH3 CH2

10 H CI H CH3 - 406 H CI H CH3 CH2

11 Br CI H CH3 - 407 Br CI H CH3 CH2

12 CI CI H CH3 - 408 CI CI H CH3 CH2 F CI H CH3 - 409 F CI H CH3 CH2

CF3 CI H CH3 - 410 CF3 CI H CH3 CH2

H F H CH3 - 411 H F H CH3 CH2

Br F H CH3 - 412 Br F H CH3 CH2

CI F H CH3 - 413 CI F H CH3 CH2

F F H CH3 - 414 F F H CH3 CH2

CF3 F H CH3 - 415 CF3 F H CH3 CH2

H H Br CH3 - 416 H H Br CH3 CH2

Br H Br CH3 - 417 Br H Br CH3 CH2

CI H Br CH3 - 418 CI H Br CH3 CH2

F H Br CH3 - 419 F H Br CH3 CH2

CF3 H Br CH3 - 420 CF3 H Br CH3 CH2

H Br Br CH3 - 421 H Br Br CH3 CH2

Br Br Br CH3 - 422 Br Br Br CH3 CH2

CI Br Br CH3 - 423 CI Br Br CH3 CH2

F Br Br CH3 - 424 F Br Br CH3 CH2

CF3 Br Br CH3 - 425 CF3 Br Br CH3 CH2

H CI Br CH3 - 426 H CI Br CH3 CH2

Br CI Br CH3 - 427 Br CI Br CH3 CH2

CI CI Br CH3 - 428 CI CI Br CH3 CH2

F CI Br CH3 - 429 F CI Br CH3 CH2

CF3 CI Br CH3 - 430 CF3 CI Br CH3 CH2

H F Br CH3 - 431 H F Br CH3 CH2

Br F Br CH3 - 432 Br F Br CH3 CH2

CI F Br CH3 - 433 CI F Br CH3 CH2

F F Br CH3 - 434 F F Br CH3 CH2

CF3 F Br CH3 - 435 CF3 F Br CH3 CH2

H H CI CH3 - 436 H H CI CH3 CH2

Br H CI CH3 - 437 Br H CI CH3 CH2

CI H CI CH3 - 438 CI H CI CH3 CH2

F H CI CH3 - 439 F H CI CH3 CH2

CF3 H CI CH3 - 440 CF3 H CI CH3 CH2

H Br CI CH3 - 441 H Br CI CH3 CH2

Br Br CI CH3 - 442 Br Br CI CH3 CH2

CI Br CI CH3 - 443 CI Br CI CH3 CH2

F Br CI CH3 - 444 F Br CI CH3 CH2

CF3 Br CI CH3 - 445 CF3 Br CI CH3 CH2

H CI CI CH3 - 446 H CI CI CH3 CH2

Br CI CI CH3 - 447 Br CI CI CH3 CH2

CI CI CI CH3 - 448 CI CI CI CH3 CH2

F CI CI CH3 - 449 F CI CI CH3 CH2

CF3 CI CI CH3 - 450 CF3 CI CI CH3 CH2

H F CI CH3 - 451 H F CI CH3 CH2

Br F CI CH3 - 452 Br F CI CH3 CH2

CI F CI CH3 - 453 CI F CI CH3 CH2

F F CI CH3 - 454 F F CI CH3 CH2 CF3 F CI CH3 - 455 CF3 F CI CH3 CH2

H H F CH3 - 456 H H F CH3 CH2

Br H F CH3 - 457 Br H F CH3 CH2

CI H F CH3 - 458 CI H F CH3 CH2

F H F CH3 - 459 F H F CH3 CH2

CF3 H F CH3 - 460 CF3 H F CH3 CH2

H Br F CH3 - 461 H Br F CH3 CH2

Br Br F CH3 - 462 Br Br F CH3 CH2

CI Br F CH3 - 463 CI Br F CH3 CH2

F Br F CH3 - 464 F Br F CH3 CH2

CF3 Br F CH3 - 465 CF3 Br F CH3 CH2

H CI F CH3 - 466 H CI F CH3 CH2

Br CI F CH3 - 467 Br CI F CH3 CH2

CI CI F CH3 - 468 CI CI F CH3 CH2

F CI F CH3 - 469 F CI F CH3 CH2

CF3 CI F CH3 - 470 CF3 CI F CH3 CH2

H F F CH3 - 471 H F F CH3 CH2

Br F F CH3 - 472 Br F F CH3 CH2

CI F F CH3 - 473 CI F F CH3 CH2

F F F CH3 - 474 F F F CH3 CH2

CF3 F F CH3 - 475 CF3 F F CH3 CH2

H H CF3 CH3 - 476 H H CF3 CH3 CH2

Br H CF3 CH3 - 477 Br H CF3 CH3 CH2

CI H CF3 CH3 - 478 CI H CF3 CH3 CH2

F H CF3 CH3 - 479 F H CF3 CH3 CH2

CF3 H CF3 CH3 - 480 CF3 H CF3 CH3 CH2

H Br CF3 CH3 - 481 H Br CF3 CH3 CH2

Br Br CF3 CH3 - 482 Br Br CF3 CH3 CH2

CI Br CF3 CH3 - 483 CI Br CF3 CH3 CH2

F Br CF3 CH3 - 484 F Br CF3 CH3 CH2

CF3 Br CF3 CH3 - 485 CF3 Br CF3 CH3 CH2

H CI CF3 CH3 - 486 H CI CF3 CH3 CH2

Br CI CF3 CH3 - 487 Br CI CF3 CH3 CH2

CI CI CF3 CH3 - 488 CI CI CF3 CH3 CH2

F CI CF3 CH3 - 489 F CI CF3 CH3 CH2

CF3 CI CF3 CH3 - 490 CF3 CI CF3 CH3 CH2

H F CF3 CH3 - 491 H F CF3 CH3 CH2

Br F CF3 CH3 - 492 Br F CF3 CH3 CH2

CI F CF3 CH3 - 493 CI F CF3 CH3 CH2

F F CF3 CH3 - 494 F F CF3 CH3 CH2

CF3 F CF3 CH3 - 495 CF3 F CF3 CH3 CH2

Br H H Br - 496 Br H H Br CH2

CI H H Br - 497 CI H H Br CH2

F H H Br - 498 F H H Br CH2

CF3 H H Br - 499 CF3 H H Br CH2

H Br H Br - 500 H Br H Br CH2 105 Br Br H Br - 501 Br Br H Br CH2

106 CI Br H Br - 502 CI Br H Br CH2

107 F Br H Br - 503 F Br H Br CH2

108 CF3 Br H Br - 504 CF3 Br H Br CH2

109 H CI H Br - 505 H CI H Br CH2

110 Br CI H Br - 506 Br CI H Br CH2

111 CI CI H Br - 507 CI CI H Br CH2

112 F CI H Br - 508 F CI H Br CH2

113 CF3 CI H Br - 509 CF3 CI H Br CH2

114 H F H Br - 510 H F H Br CH2

115 Br F H Br - 511 Br F H Br CH2

116 CI F H Br - 512 CI F H Br CH2

117 F F H Br - 513 F F H Br CH2

118 CF3 F H Br - 514 CF3 F H Br CH2

119 H H Br Br - 515 H H Br Br CH2

120 Br H Br Br - 516 Br H Br Br CH2

121 CI H Br Br - 517 CI H Br Br CH2

122 F H Br Br - 518 F H Br Br CH2

123 CF3 H Br Br - 519 CF3 H Br Br CH2

124 H Br Br Br - 520 H Br Br Br CH2

125 Br Br Br Br - 521 Br Br Br Br CH2

126 CI Br Br Br - 522 CI Br Br Br CH2

127 F Br Br Br - 523 F Br Br Br CH2

128 CF3 Br Br Br - 524 CF3 Br Br Br CH2

129 H CI Br Br - 525 H CI Br Br CH2

130 Br CI Br Br - 526 Br CI Br Br CH2

131 CI CI Br Br - 527 CI CI Br Br CH2

132 F CI Br Br - 528 F CI Br Br CH2

133 CF3 CI Br Br - 529 CF3 CI Br Br CH2

134 H F Br Br - 530 H F Br Br CH2

135 Br F Br Br - 531 Br F Br Br CH2

136 CI F Br Br - 532 CI F Br Br CH2

137 F F Br Br - 533 F F Br Br CH2

138 CF3 F Br Br - 534 CF3 F Br Br CH2

139 H H CI Br - 535 H H CI Br CH2

140 Br H CI Br - 536 Br H CI Br CH2

141 CI H CI Br - 537 CI H CI Br CH2

142 F H CI Br - 538 F H CI Br CH2

143 CF3 H CI Br - 539 CF3 H CI Br CH2

144 H Br CI Br - 540 H Br CI Br CH2

145 Br Br CI Br - 541 Br Br CI Br CH2

146 CI Br CI Br - 542 CI Br CI Br CH2

147 F Br CI Br - 543 F Br CI Br CH2

148 CF3 Br CI Br - 544 CF3 Br CI Br CH2

149 H CI CI Br - 545 H CI CI Br CH2

150 Br CI CI Br - 546 Br CI CI Br CH2 151 CI CI CI Br - 547 CI CI CI Br CH2

152 F CI CI Br - 548 F CI CI Br CH2

153 CF3 CI CI Br - 549 CF3 CI CI Br CH2

154 H F CI Br - 550 H F CI Br CH2

155 Br F CI Br - 551 Br F CI Br CH2

156 CI F CI Br - 552 CI F CI Br CH2

157 F F CI Br - 553 F F CI Br CH2

158 CF3 F CI Br - 554 CF3 F CI Br CH2

159 H H F Br - 555 H H F Br CH2

160 Br H F Br - 556 Br H F Br CH2

161 CI H F Br - 557 CI H F Br CH2

162 F H F Br - 558 F H F Br CH2

163 CF3 H F Br - 559 CF3 H F Br CH2

164 H Br F Br - 560 H Br F Br CH2

165 Br Br F Br - 561 Br Br F Br CH2

166 CI Br F Br - 562 CI Br F Br CH2

167 F Br F Br - 563 F Br F Br CH2

168 CF3 Br F Br - 564 CF3 Br F Br CH2

169 H CI F Br - 565 H CI F Br CH2

170 Br CI F Br - 566 Br CI F Br CH2

171 CI CI F Br - 567 CI CI F Br CH2

172 F CI F Br - 568 F CI F Br CH2

173 CF3 CI F Br - 569 CF3 CI F Br CH2

174 H F F Br - 570 H F F Br CH2

175 Br F F Br - 571 Br F F Br CH2

176 CI F F Br - 572 CI F F Br CH2

177 F F F Br - 573 F F F Br CH2

178 CF3 F F Br - 574 CF3 F F Br CH2

179 H H CF3 Br - 575 H H CF3 Br CH2

180 Br H CF3 Br - 576 Br H CF3 Br CH2

181 CI H CF3 Br - 577 CI H CF3 Br CH2

182 F H CF3 Br - 578 F H CF3 Br CH2

183 CF3 H CF3 Br - 579 CF3 H CF3 Br CH2

184 H Br CF3 Br - 580 H Br CF3 Br CH2

185 Br Br CF3 Br - 581 Br Br CF3 Br CH2

186 CI Br CF3 Br - 582 CI Br CF3 Br CH2

187 F Br CF3 Br - 583 F Br CF3 Br CH2

188 CF3 Br CF3 Br - 584 CF3 Br CF3 Br CH2

189 H CI CF3 Br - 585 H CI CF3 Br CH2

190 Br CI CF3 Br - 586 Br CI CF3 Br CH2

191 CI CI CF3 Br - 587 CI CI CF3 Br CH2

192 F CI CF3 Br - 588 F CI CF3 Br CH2

193 CF3 CI CF3 Br - 589 CF3 CI CF3 Br CH2

194 H F CF3 Br - 590 H F CF3 Br CH2

195 Br F CF3 Br - 591 Br F CF3 Br CH2

196 CI F CF3 Br - 592 CI F CF3 Br CH2 197 F F CF3 Br - 593 F F CF3 Br CH2

198 CF3 F CF3 Br - 594 CF3 F CF3 Br CH2

199 Br H H CI - 595 Br H H CI CH2

200 CI H H CI - 596 CI H H CI CH2

201 F H H CI - 597 F H H CI CH2

202 CF3 H H CI - 598 CF3 H H CI CH2

203 H Br H CI - 599 H Br H CI CH2

204 Br Br H CI - 600 Br Br H CI CH2

205 CI Br H CI - 601 CI Br H CI CH2

206 F Br H CI - 602 F Br H CI CH2

207 CF3 Br H CI - 603 CF3 Br H CI CH2

208 H CI H CI - 604 H CI H CI CH2

209 Br CI H CI - 605 Br CI H CI CH2

210 CI CI H CI - 606 CI CI H CI CH2

211 F CI H CI - 607 F CI H CI CH2

212 CF3 CI H CI - 608 CF3 CI H CI CH2

213 H F H CI - 609 H F H CI CH2

214 Br F H CI - 610 Br F H CI CH2

215 CI F H CI - 611 CI F H CI CH2

216 F F H CI - 612 F F H CI CH2

217 CF3 F H CI - 613 CF3 F H CI CH2

218 H H Br CI - 614 H H Br CI CH2

219 Br H Br CI - 615 Br H Br CI CH2

220 CI H Br CI - 616 CI H Br CI CH2

221 F H Br CI - 617 F H Br CI CH2

222 CF3 H Br CI - 618 CF3 H Br CI CH2

223 H Br Br CI - 619 H Br Br CI CH2

224 Br Br Br CI - 620 Br Br Br CI CH2

225 CI Br Br CI - 621 CI Br Br CI CH2

226 F Br Br CI - 622 F Br Br CI CH2

227 CF3 Br Br CI - 623 CF3 Br Br CI CH2

228 H CI Br CI - 624 H CI Br CI CH2

229 Br CI Br CI - 625 Br CI Br CI CH2

230 CI CI Br CI - 626 CI CI Br CI CH2

231 F CI Br CI - 627 F CI Br CI CH2

232 CF3 CI Br CI - 628 CF3 CI Br CI CH2

233 H F Br CI - 629 H F Br CI CH2

234 Br F Br CI - 630 Br F Br CI CH2

235 CI F Br CI - 631 CI F Br CI CH2

236 F F Br CI - 632 F F Br CI CH2

237 CF3 F Br CI - 633 CF3 F Br CI CH2

238 H H CI CI - 634 H H CI CI CH2

239 Br H CI CI - 635 Br H CI CI CH2

240 CI H CI CI - 636 CI H CI CI CH2

241 F H CI CI - 637 F H CI CI CH2

242 CF3 H CI CI - 638 CF3 H CI CI CH2 243 H Br CI CI - 639 H Br CI CI CH2

244 Br Br CI CI - 640 Br Br CI CI CH2

245 CI Br CI CI - 641 CI Br CI CI CH2

246 F Br CI CI - 642 F Br CI CI CH2

247 CF3 Br CI CI - 643 CF3 Br CI CI CH2

248 H CI CI CI - 644 H CI CI CI CH2

249 Br CI CI CI - 645 Br CI CI CI CH2

250 CI CI CI CI - 646 CI CI CI CI CH2

251 F CI CI CI - 647 F CI CI CI CH2

252 CF3 CI CI CI - 648 CF3 CI CI CI CH2

253 H F CI CI - 649 H F CI CI CH2

254 Br F CI CI - 650 Br F CI CI CH2

255 CI F CI CI - 651 CI F CI CI CH2

256 F F CI CI - 652 F F CI CI CH2

257 CF3 F CI CI - 653 CF3 F CI CI CH2

258 H H F CI - 654 H H F CI CH2

259 Br H F CI - 655 Br H F CI CH2

260 CI H F CI - 656 CI H F CI CH2

261 F H F CI - 657 F H F CI CH2

262 CF3 H F CI - 658 CF3 H F CI CH2

263 H Br F CI - 659 H Br F CI CH2

264 Br Br F CI - 660 Br Br F CI CH2

265 CI Br F CI - 661 CI Br F CI CH2

266 F Br F CI - 662 F Br F CI CH2

267 CF3 Br F CI - 663 CF3 Br F CI CH2

268 H CI F CI - 664 H CI F CI CH2

269 Br CI F CI - 665 Br CI F CI CH2

270 CI CI F CI - 666 CI CI F CI CH2

271 F CI F CI - 667 F CI F CI CH2

272 CF3 CI F CI - 668 CF3 CI F CI CH2

273 H F F CI - 669 H F F CI CH2

274 Br F F CI - 670 Br F F CI CH2

275 CI F F CI - 671 CI F F CI CH2

276 F F F CI - 672 F F F CI CH2

277 CF3 F F CI - 673 CF3 F F CI CH2

278 H H CF3 CI - 674 H H CF3 CI CH2

279 Br H CF3 CI - 675 Br H CF3 CI CH2

280 CI H CF3 CI - 676 CI H CF3 CI CH2

281 F H CF3 CI - 677 F H CF3 CI CH2

282 CF3 H CF3 CI - 678 CF3 H CF3 CI CH2

283 H Br CF3 CI - 679 H Br CF3 CI CH2

284 Br Br CF3 CI - 680 Br Br CF3 CI CH2

285 CI Br CF3 CI - 681 CI Br CF3 CI CH2

286 F Br CF3 CI - 682 F Br CF3 CI CH2

287 CF3 Br CF3 CI - 683 CF3 Br CF3 CI CH2

288 H CI CF3 CI - 684 H CI CF3 CI CH2 289 Br CI CF3 CI - 685 Br CI CF3 CI CH2

290 CI CI CF3 CI - 686 CI CI CF3 CI CH2

291 F CI CF3 CI - 687 F CI CF3 CI CH2

292 CF3 CI CF3 CI - 688 CF3 CI CF3 CI CH2

293 H F CF3 CI - 689 H F CF3 CI CH2

294 Br F CF3 CI - 690 Br F CF3 CI CH2

295 CI F CF3 CI - 691 CI F CF3 CI CH2

296 F F CF3 CI - 692 F F CF3 CI CH2

297 CF3 F CF3 CI - 693 CF3 F CF3 CI CH2

298 Br H H CF3 - 694 Br H H CF3 CH2

299 CI H H CF3 - 695 CI H H CF3 CH2

300 F H H CF3 - 696 F H H CF3 CH2

301 CF3 H H CF3 - 697 CF3 H H CF3 CH2

302 H Br H CF3 - 698 H Br H CF3 CH2

303 Br Br H CF3 - 699 Br Br H CF3 CH2

304 CI Br H CF3 - 700 CI Br H CF3 CH2

305 F Br H CF3 - 701 F Br H CF3 CH2

306 CF3 Br H CF3 - 702 CF3 Br H CF3 CH2

307 H CI H CF3 - 703 H CI H CF3 CH2

308 Br CI H CF3 - 704 Br CI H CF3 CH2

309 CI CI H CF3 - 705 CI CI H CF3 CH2

310 F CI H CF3 - 706 F CI H CF3 CH2

311 CF3 CI H CF3 - 707 CF3 CI H CF3 CH2

312 H F H CF3 - 708 H F H CF3 CH2

313 Br F H CF3 - 709 Br F H CF3 CH2

314 CI F H CF3 - 710 CI F H CF3 CH2

315 F F H CF3 - 711 F F H CF3 CH2

316 CF3 F H CF3 - 712 CF3 F H CF3 CH2

317 H H Br CF3 - 713 H H Br CF3 CH2

318 Br H Br CF3 - 714 Br H Br CF3 CH2

319 CI H Br CF3 - 715 CI H Br CF3 CH2

320 F H Br CF3 - 716 F H Br CF3 CH2

321 CF3 H Br CF3 - 717 CF3 H Br CF3 CH2

322 H Br Br CF3 - 718 H Br Br CF3 CH2

323 Br Br Br CF3 - 719 Br Br Br CF3 CH2

324 CI Br Br CF3 - 720 CI Br Br CF3 CH2

325 F Br Br CF3 - 721 F Br Br CF3 CH2

326 CF3 Br Br CF3 - 722 CF3 Br Br CF3 CH2

327 H CI Br CF3 - 723 H CI Br CF3 CH2

328 Br CI Br CF3 - 724 Br CI Br CF3 CH2

329 CI CI Br CF3 - 725 CI CI Br CF3 CH2

330 F CI Br CF3 - 726 F CI Br CF3 CH2

331 CF3 CI Br CF3 - 727 CF3 CI Br CF3 CH2

332 H F Br CF3 - 728 H F Br CF3 CH2

333 Br F Br CF3 - 729 Br F Br CF3 CH2

334 CI F Br CF3 - 730 CI F Br CF3 CH2 335 F F Br CF3 - 731 F F Br CF3 CH2

336 CF3 F Br CF3 - 732 CF3 F Br CF3 CH2

337 H H CI CF3 - 733 H H CI CF3 CH2

338 Br H CI CF3 - 734 Br H CI CF3 CH2

339 CI H CI CF3 - 735 CI H CI CF3 CH2

340 F H CI CF3 - 736 F H CI CF3 CH2

341 CF3 H CI CF3 - 737 CF3 H CI CF3 CH2

342 H Br CI CF3 - 738 H Br CI CF3 CH2

343 Br Br CI CF3 - 739 Br Br CI CF3 CH2

344 CI Br CI CF3 - 740 CI Br CI CF3 CH2

345 F Br CI CF3 - 741 F Br CI CF3 CH2

346 CF3 Br CI CF3 - 742 CF3 Br CI CF3 CH2

347 H CI CI CF3 - 743 H CI CI CF3 CH2

348 Br CI CI CF3 - 744 Br CI CI CF3 CH2

349 CI CI CI CF3 - 745 CI CI CI CF3 CH2

350 F CI CI CF3 - 746 F CI CI CF3 CH2

351 CF3 CI CI CF3 - 747 CF3 CI CI CF3 CH2

352 H F CI CF3 - 748 H F CI CF3 CH2

353 Br F CI CF3 - 749 Br F CI CF3 CH2

354 CI F CI CF3 - 750 CI F CI CF3 CH2

355 F F CI CF3 - 751 F F CI CF3 CH2

356 CF3 F CI CF3 - 752 CF3 F CI CF3 CH2

357 H H F CF3 - 753 H H F CF3 CH2

358 Br H F CF3 - 754 Br H F CF3 CH2

359 CI H F CF3 - 755 CI H F CF3 CH2

360 F H F CF3 - 756 F H F CF3 CH2

361 CF3 H F CF3 - 757 CF3 H F CF3 CH2

362 H Br F CF3 - 758 H Br F CF3 CH2

363 Br Br F CF3 - 759 Br Br F CF3 CH2

364 CI Br F CF3 - 760 CI Br F CF3 CH2

365 F Br F CF3 - 761 F Br F CF3 CH2

366 CF3 Br F CF3 - 762 CF3 Br F CF3 CH2

367 H CI F CF3 - 763 H CI F CF3 CH2

368 Br CI F CF3 - 764 Br CI F CF3 CH2

369 CI CI F CF3 - 765 CI CI F CF3 CH2

370 F CI F CF3 - 766 F CI F CF3 CH2

371 CF3 CI F CF3 - 767 CF3 CI F CF3 CH2

372 H F F CF3 - 768 H F F CF3 CH2

373 Br F F CF3 - 769 Br F F CF3 CH2

374 CI F F CF3 - 770 CI F F CF3 CH2

375 F F F CF3 - 771 F F F CF3 CH2

376 CF3 F F CF3 - 772 CF3 F F CF3 CH2

377 H H CF3 CF3 - 773 H H CF3 CF3 CH2

378 Br H CF3 CF3 - 774 Br H CF3 CF3 CH2

379 CI H CF3 CF3 - 775 CI H CF3 CF3 CH2

380 F H CF3 CF3 - 776 F H CF3 CF3 CH2 381 CF3 H CF3 CF3 - 777 CF3 H CF3 CF3 CH2

382 H Br CF3 CF3 - 778 H Br CF3 CF3 CH2

383 Br Br CF3 CF3 - 779 Br Br CF3 CF3 CH2

384 CI Br CF3 CF3 - 780 CI Br CF3 CF3 CH2

385 F Br CF3 CF3 - 781 F Br CF3 CF3 CH2

386 CF3 Br CF3 CF3 - 782 CF3 Br CF3 CF3 CH2

387 H CI CF3 CF3 - 783 H CI CF3 CF3 CH2

388 Br CI CF3 CF3 - 784 Br CI CF3 CF3 CH2

389 CI CI CF3 CF3 - 785 CI CI CF3 CF3 CH2

390 F CI CF3 CF3 - 786 F CI CF3 CF3 CH2

391 CF3 CI CF3 CF3 - 787 CF3 CI CF3 CF3 CH2

392 H F CF3 CF3 - 788 H F CF3 CF3 CH2

393 Br F CF3 CF3 - 789 Br F CF3 CF3 CH2

394 CI F CF3 CF3 - 790 CI F CF3 CF3 CH2

395 F F CF3 CF3 - 791 F F CF3 CF3 CH2

396 CF3 F CF3 CF3 - 792 CF3 F CF3 CF3 CH2

In one embodiment the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing soil pests. In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing wire worms.

In one embodiment the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing wire worms.

In one embodiment the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing wire worms.

In one embodiment the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing wire worms.

In one embodiment the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing wire worms. In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing wire worms.

In one embodiment the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing wire worms.

In one embodiment the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing wire worms.

In one embodiment the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing wire worms.

In one embodiment the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing wire worms.

In one embodiment the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing wire worms.

In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing wire worms.

In one embodiment the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing grubs, in particular white grubs. In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing Diloboderus sp.. In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing Popillia japonica. In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp.. In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing cutworms, e.g. agrotis sp.. In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 1 to 6 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 7 to 12 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 13 to 18 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 19 to 24 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 25 to 30 for use in controlling and/or preventing broca gigante, e.g. Telchin licus. In one embodiment the invention provides a compound selected from Tables 31 to 36 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 37 to 39 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 40 to 42 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 43 to 45 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 46 to 48 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 49 to 51 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 52 to 54 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the compounds of formula (I), in particular those in in Tables 1 to 54 above may be used to combat soil grubs e.g. Migdolus sp.; Phyllophaga sp.; Diloboderus sp.; Cyclocephala sp; Lyogenys fuscus; Popillia japonica; sugar cane weevils e.g. Sphenophorus levis and Metamasius hemipterus; termites e.g. Heterotermes tenuis; Heterotermes longiceps; Cornitermes cumulans;

Procornitermes triacifer; Neocapritermes opacus; Neocapritermes parvus; corn rootworms e.g.

Diabrotica sp., seed Maggot e.g. Delia platura; soil stinkbugs e.g. Scaptocoris castanea; wireworms e.g. Agriotes sp.; Athous sp.; Hipnodes bicolor; Ctenicera destructor; Limonius canu; Limonius californicus .

In another embodiment the compounds of formula (I), in particular those in in Tables 1 to 54 above may be used for seed applications at least on the following: soil grubs for corn, soybeans, sugarcane: e.g. Migdolus sp.; Phyllophaga sp.; Diloboderus sp.; Cyclocephala sp.; Lyogenys fuscus; Popillia japonica; termites for soybeans, sugarcane, pasture: e.g. Heterotermes tenuis; Heterotermes longiceps; Cornitermes cumulans; Procornitermes triacifer; Neocapritermes opacus; Neocapritermes parvus; corn rootworms for corn and potatoes: e.g. Diabrotica sp., rice water weevil e.g. Lissorhoptrus oryzophilus; red legged earth mites e.g. Halotydeus destructor.

In one embodiment the compounds of formula (I), in particular those in Tables 1 to 54 above, may be used for soil applications, including as a seed application, to target at least the following: sucking pests such as aphids, thrips, brown plant hopper (e.g. on rice), sting bugs, white flies (e.g. on cotton and vegetables), mites; on soil pests such as corn rootworm, wireworms, white grubs, zabrus, termites (e.g. on sugar cane, soy, pasture), maggots, cabbage root fly, red legged earth mite; on lepidoptera, such as spodoptera, cutworms, elasmoplpus, plutella (e.g. brassica), stem borers, leaf miners, flea beetle, Sternechus; on nematicides, such as Heterodera glycines (e.g. on soybean), Pratylenchus brachyurus (e.g. on corn), P. zeae (e.g. oncorn), P. penetrans (e.g. on corn), Meloidogyne incognita (e.g. on vegetables), Heterodera schachtii (e.g. on sugar beet), Rotylenchus reniformis (e.g. on cotton), Heterodera avenae (e.g. on cereals), Pratylenchus neglectus (e.g. on cereals), thornei (e.g. on cereals).

In one embodiment the methods and uses of the invention are for controlling and/or preventing infestation of useful plants by corn rootworm, wireworms, grubs, in particular white grubs, termites, subterraneous stinkbugs, cutworms, millipedes and broca gigante that are resistant to other insecticides. Corn rootworm, wireworms, grubs and whitefly that are "resistant" to a particular insecticide refers e.g. to strains of corn rootworm, wireworms, grubs and whitefly that are less sensitive to that insecticide compared to the expected sensitivity of the same species of the respective pest. The expected sensitivity can be measured using e.g. a strain that has not previously been exposed to the insecticide.

Useful plants include soybean, corn, sugarcane, alfalfa, brassicas, oilseed rape (e.g. canola), potatoes (including sweet potatoes), cotton, rice, coffee, citrus, almonds, fruiting vegetables, cucurbits and pulses (e.g. tomatoes, pepper, chili, eggplant, cucumber, squash etc.), tea, bulb vegetables (e.g. onion, leek etc.), grapes, pome fruit (e.g. apples, pears etc.), stone fruit (e.g. pears, plums etc.), and cereals.

The term "locus" of a useful plant as used herein is intended to embrace the place on which the useful plants are growing, where the plant propagation materials of the useful plants are sown or where the plant propagation materials of the useful plants will be placed into the soil. An example for such a locus is a field, on which crop plants are growing.

The term "plant propagation material" is understood to denote generative parts of a plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably "plant propagation material" is understood to denote seeds.

Application of the compound of formula I may be before infestation or before the pest is present, or may be after the presence of the pest or at the time of infestation.

The compound of formula I may be applied directly to soil or may be applied to soil by treating plant propagation material, e.g. a seed, with the compound of formula I.

Methods of applying to the soil can be via any suitable method, which ensures that the combination penetrates the soil, for example, nursery tray application, in furrow application, soil drenching, soil injection, drip irrigation, application through sprinklers or central pivot, incorporation into soil (broad cast or in band) are such methods. Alternatively or in addition one or more materials may be applied on a suitable substrate, for example a seed which is not intended for germination, and "sowing" the treated substrate with the plant propagation material. A preferred method of applying to soil is in- furrow at sowing, e.g. as liquid spray or as granule. An extension to in-furrow application is so-called t- band application at sowing in which some of the spray or granule is additionally deposited at the soil surface. Methods for applying or treating active ingredients on to plant propagation material, especially seeds, are known in the art, and include dressing, coating, pelleting and soaking application methods of the propagation material. Conventional treating techniques and machines can be used, such as fluidized beds, roller mills, rotostatic seed treaters, drum coaters, and spouted beds.

Even distribution of ingredients and good adherence is particularly desired for seed treatment.

Treatment could vary from a thin film or dressing of the formulation, for example, a mixture of active ingredients, on a plant propagation material, such as a seed, where the original size and/or shape are recognizable to an intermediary state to a thicker film such as pelleting with many layers of different materials (such as carriers, for example, clays; different formulations, such as of other active ingredients; polymers; and colourants) where the original shape and/or size of the seed is no longer recognisable.

Application onto plant propagation material can include controlled release coatings, wherein the ingredients of the combinations are incorporated into materials that release the ingredients over time. Examples of controlled release technologies are generally known in the art and include polymer films and waxes, wherein the ingredients may be incorporated into the controlled release material or applied between layers of materials, or both.

The compounds of the invention are suitable for use on any 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 infestation by plant pests.

The term "plants" are to be understood as also including those plants which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO- and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering. An example of a plant that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer rape (canola). Examples of plants that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate -resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®.

Compounds of formula I may be used on transgenic plants (including cultivars) obtained by genetic engineering methods and/or by conventional methods. These are understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive "synergistic") effects.

Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.

The preferred transgenic plants or plant cultivars which are to be treated according to the invention include all plants which, by virtue of the genetic modification, received genetic material which imparts particularly advantageous, useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products.

Further and particularly emphasized examples of such traits are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds.

Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soybean, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes).

Compounds of formula I may be used on transgenic plants that are capable of producing one or more pesticidal proteins which confer upon the transgenic plant tolerance or resistance to harmful pests, e.g. insect pests, nematode pests and the like. Such pesticidal proteins include, without limitation, Cry proteins from Bacillus thuringiensis CrylAb, CrylAc, CrylF, Cry2Ab, Cry2Ae, Cry3A, Cry3Bb, or Cry9C; engineered proteins such as modified Cry3A ( US Patent 7,030,295) or CrylA.105; or vegetative insecticidal proteins such as Vipl, Vip2 or Vip3. A full list of Bt Cry proteins and VIPs useful in the invention can be found on the worldwide web at Bacillus thuringiensis Toxin Nomenclature Database maintained by the University of Sussex {see also, Crickmore et al. (1998) Microbiol. Mol. Biol. Rev. 62:807-813). Other pesticidal proteins useful in the invention include proteins of bacteria colonizing nematodes, e.g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome- inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. Further examples of such pesticidal proteins or transgenic plants capable of synthesizing such proteins are disclosed, e.g., in EP-A 374753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451878, WO 03/18810 and WO 03/52073. The methods for producing such transgenic plants are generally known to the person skilled in the art and some of which are commercially available such as Agrisure®CB (PI) (corn producing CrylAb), Agrisure®RW (P2) (corn producing mCry3A), Agrisure® Viptera (P3) (corn hybrids producing Vip3Aa); Agrisure300GT (P4) (corn hybrids producing Cryl Ab and mCry3A); YieldGard® (P5) (corn hybrids producing the Cryl Ab protein), YieldGard® Plus (P6) (corn hybrids producing CrylAb and Cry3Bbl), Genuity® SmartStax® (P7) (corn hybrids with CrylA.105, Cry2Ab2, CrylF, Cry34/35, Cry3Bb) ; Herculex® I (P8) (corn hybrids producing CrylFa) and Herculex®RW (P9) (corn hybrids producing Cry34Abl, Cry35Abl and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]) ; NuCOTN®33B (P10) (cotton cultivars producing CrylAc), Bollgard®I (PI 1) (cotton cultivars producing CrylAc), Bollgard®II (P12) (cotton cultivars producing CrylAc and Cry2Ab2) and VIPCOT® (P13) (cotton cultivars producing a Vip3Aa). Soybean Cyst Nematode resistance soybean (SCN® - Syngenta (PI 4)) and soybean with Aphid resistant trait (AMT® (PI 5)) are also of interest.

Further examples of such transgenic crops are:

1. Btll Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 (P16). Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer {Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylA(b) toxin. Btl 1 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

2. Btl 76 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 (PI 7). Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer {Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylA(b) toxin. Btl 76 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 (PI 8). Maize which has been rendered insect-resistant by transgenic expression of a modified CrylllA toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-D-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.

4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-l 150 Brussels, Belgium, registration number C/DE/02/9 (P19). MON 863 expresses a CrylllB(bl) toxin and has resistance to certain Coleoptera insects.

5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-l 150 Brussels,

Belgium, registration number C/ES/96/02. (P20)

6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-l 160 Brussels, Belgium, registration number C/NL/00/10. (P21) Genetically modified maize for the expression of the protein CrylF for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.

7. NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,

B-l 150 Brussels, Belgium, registration number C/GB/02/M3/03 . Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 ^χ MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylA(b) toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.

Further examples of transgenic plants, and of very high interest, are those carrying traits conferring resistance to 2.4D (e.g. Enlist®) (e.g. WO 2011066384) (, glyphosate (e.g. Roundup Ready® (P24), Roundup Ready 2 Yield® (P25)), sulfonylurea (e.g. STS®) (P26), glufosinate (e.g. Liberty Link® (P27), Ignite® (P28)), Dicamba (P29) (Monsanto), HPPD tolerance (P30) (e.g. isoxaflutole herbicide) (Bayer CropScience, Syngenta). Double or triple stacks of any of the traits described here are also of interest, including glyphosate and sulfonyl-urea tolerance ((e.g. Optimum GAT®) (P31), plants stacked with STS® and Roundup Ready® (P32) or plants stacked with STS® and Roundup Ready 2 Yield® (P33)), dicamba and glyphosate tolerance (P34) (Monsanto). Of particular interest are soybean plants carrying trains conferring resistance to 2.4D (e.g. Enlist®), glyphosate (e.g. Roundup Ready®, Roundup Ready 2 Yield®), sulfonylurea (e.g. STS®), glufosinate (e.g. Liberty Link®, Ignite®), Dicamba

(Monsanto) HPPD tolerance (e.g. isoxaflutole herbicide) (Bayer CropScience, Syngenta).

Transgenic crops of insect-resistant plants are also described in BATS (Zentrum fur Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003,

(http://bats.ch).

Herbicide -resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield(®) (for example maize).

These statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which plant cultivars will be developed and/or marketed in the future.

A compound of the invention may be used in mixtures with fertilizers (for example nitrogen-, potassium- or phosphorus-containing fertilizers). Suitable formulation types include granules of fertilizer. The mixtures preferably contain up to 25% by weight of the compound of the invention.

The invention therefore also provides a fertilizer composition comprising a fertilizer and a compound of the invention.

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

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

The compound of formula (I) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, e.g. a insecticide, fungicide or herbicide, or a synergist or plant growth regulator where appropriate. An additional active ingredient may provide a composition having a broader spectrum of activity or increased persistence at a locus; synergize the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of formula (I); or help to overcome or prevent the development of resistance to individual components. The particular additional active ingredient will depend upon the intended utility of the composition. Examples of suitable pesticides include the following:

a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin and gamma cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, S-bioallethrin, fenfluthrin, prallethrin, acrinathirin, etofenprox or

5-benzyl-3-furylmethyl-(E)-(l R,3 S)-2,2-dimethyl- 3 -(2-oxothiolan-3 -ylidenemethyl)cyclopropane carboxylate;

b) Organophosphates, such as profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s -methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate or diazinon; c) Carbamates (including aryl carbamates), such as pirimicarb, triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb, aldicarb, thiofurox, carbosulfan, bendiocarb, fenobucarb, propoxur, methomyl or oxamyl;

d) Benzoyl ureas, such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron, diafenthiuron, lufeneron, novaluron, noviflumuron or chlorfluazuron;

e) Organic tin compounds, such as cyhexatin, fenbutatin oxide or azocyclotin;

f) Pyrazoles, such as tebufenpyrad, tolfenpyrad, ethiprole, pyriprole, fipronil, and fenpyroximate;

g) Macrolides, such as avermectins or milbemycins, for example abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad, azadirachtin, milbemectin, lepimectin or spinetoram;

h) Hormones or pheromones;

i) Organochlorine compounds, such as endosulfan (in particular alpha-endosulfan), benzene hexachloride,

DDT, chlordane or dieldrin;

j) Amidines, such as chlordimeform or amitraz;

k) Fumigant agents, such as chloropicrin, dichloropropane, methyl bromide or metam;

1) Neonicotinoid compounds, such as imidacloprid, thiacloprid, acetamiprid, nitenpyram, dinotefuran, thiamethoxam, clothianidin, or nithiazine;

m) Diacylhydrazines, such as tebufenozide, chromafenozide or methoxyfenozide;

n) Diphenyl ethers, such as diofenolan or pyriproxifen;

o) Ureas such as Indoxacarb or metaflumizone;

p) Ketoenols, such as Spirotetramat, spirodiclofen or spiromesifen;

q) Diamides, such as flubendiamide, chlorantraniliprole (Rynaxypyr®) or cyantraniliprole;

r) Essential oils such as Bugoil® - (Plantlmpact); or s) a comopund selected from buprofezine, flonicamid, acequinocyl, bifenazate, cyenopyrafen, cyflumetofen, etoxazole, flometoquin, fluacrypyrim, fluensulfone, flufenerim, flupyradifuone, harpin, iodomethane, dodecadienol, pyridaben, pyridalyl, pyrimidifen, flupyradifurone, 4-[(6-Chloro-pyridin-3- ylmethyl)-(2,2-difluoro-ethyl)-amino]-5H-furan-2-one (DE 102006015467), CAS: 915972-17-7

(WO 2006129714; WO2011/147953; WO2011/147952), CAS: 26914-55-8 (WO 2007020986), chlorfenapyr, pymetrozine, sulfoxaflor and pyrifluqinazon.

In addition to the major chemical classes of pesticide listed above, other pesticides having particular targets may be employed in the composition, if appropriate for the intended utility of the composition. For instance, selective insecticides for particular crops, for example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such as buprofezin) for use in rice may be employed. Alternatively insecticides or acaricides specific for particular insect species/stages may also be included in the compositions (for example acaricidal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or tetradifon; acaricidal motilicides, such as dicofol or propargite; acaricides, such as bromopropylate or chlorobenzilate; or growth regulators, such as hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron).

Examples of fungicidal compounds which may be included in the composition of the invention are (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-metho xy-iminoacetamide (SSF-129), 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole- l -sulfonamide,

a-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]-y-butyrolac tone, 4-chloro-2-cyano-N,N-dimethyl-5-/?- tolylimidazole-1 -sulfonamide (IKF-916, cyamidazosulfamid), 3-5-dichloro-N-(3-chloro-l-ethyl-l -methyl-

2- oxopropyl)-4-methylbenzamide (RH-7281 , zoxamide), N-allyl-4,5,-dimethyl-2-trimethylsilylthiophene-

3- carboxamide (ΜΟΝ65500), N-(l -cyano-1 ,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propionamide (AC382042), N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide, acibenzolar (CGA245704) (e.g. acibenzolar-S-methyl), alanycarb, aldimorph, anilazine, azaconazole, azoxystrobin, benalaxyl, benomyl, benthiavalicarb, biloxazol, bitertanol, bixafen, blasticidin S, boscalid, bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chlorothalonil, chlorozolinate, clozylacon, copper containing compounds such as copper oxychloride, copper oxyquinolate, copper sulfate, copper tallate and Bordeaux mixture, cyclufenamid, cymoxanil, cyproconazole, cyprodinil, debacarb, di-2-pyridyl disulfide 1,1 '-dioxide, dichlofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, difenzoquat, diflumetorim,

OjO-di-wo-propyl-S-benzyl thiophosphate, dimefluazole, dimetconazole, dimethomorph, dimethirimol, diniconazole, dinocap, dithianon, dodecyl dimethyl ammonium chloride, dodemorph, dodine, doguadine, edifenphos, epoxiconazole, ethirimol, ethyl-(Z)-N-benzyl-N-([methyl(methyl-thioethylideneamino- oxycarbonyl)amino]thio)- -alaninate, etridiazole, famoxadone, fenamidone (RPA407213), fenarimol, fenbuconazole, fenfuram, fenhexamid (KBR2738), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, fluopyram,

fluoxastrobin, fluoroimide, fluquinconazole, flusilazole, flutolanil, flutriafol, fluxapyroxad, folpet, fuberidazole, furalaxyl, furametpyr, guazatine, hexaconazole, hydroxyisoxazole, hymexazole, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb (SZX0722), isopropanyl butyl carbamate, isoprothiolane, isopyrazam, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, mandipropamid, maneb, mefenoxam, metalaxyl, mepanipyrim, mepronil, metalaxyl, metconazole, metiram, metiram-zinc, metominostrobin, myclobutanil, neoasozin, nickel dimethyldithiocarbamate, nitrothal-wopropyl, nuarimol, ofurace, organomercury compounds, oxadixyl, oxasulfuron, oxolinic acid, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, penthiopyrad, phenazin oxide, phosetyl-Al, phosphorus acids, phthalide, picoxystrobin (ZA1963), polyoxinD, polyram, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, propionic acid, prothioconazole, pyrazophos, pyrifenox, pyrimethanil, pyraclostrobin, pyroquilon, pyroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinomethionate, quinoxyfen, quintozene, sedaxane, sipconazole (F-155), sodium pentachlorophenate, spiroxamine, streptomycin, sulfur, tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, thifluzamid, 2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl, thiram, timibenconazole, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, tricyclazole, tridemorph, trifloxystrobin (CGA279202), triforine, triflumizole, triticonazole, validamycin A, vapam, vinclozolin, zineb and ziram, N- [9 -(dichloromethylene) -1,2,3,4 -tetrahydro- 1 ,4 -methanonaphthalen-5 -yl] -3 -(difluoromethyl) - 1 -methyl- lH-pyrazole-4-carboxamide [1072957-71 -1], l-methyl-3 -difluoromethyl- lH-pyrazole-4-carboxylic acid (2-dichloromethylene-3 -ethyl- 1 -methyl -indan-4-yl) -amide, and l -methyl-3-difluoromethyl-4H-pyrazole- 4-carboxylic acid [2-(2,4-dichloro-phenyl)-2-methoxy-l -methyl-ethyl] -amide.

In addition, biological agents may be included in the composition of the invention e.g. Baciullus species such as Bacillus firmus, Bacillus cereus, Bacillus subtilis, and Pasteuria species such as Pasteuria penetrans and Pasteuria nishizawae. A suitable Bacillus firmus strain is strain CNCM 1-1582 which is commercially available as BioNem™. A suitable Bacillus cereus strain is strain CNCM 1-1562. Of both Bacillus strains more details can be found in US 6,406,690. Other biological organisms that may be included in the compositions of the invention are bacteria such as Streptomyces spp. such as S.

avermitilis, and fungi such as Pochonia spp. such as P. chlamydosporia. Also of interest are Metarhizium spp. such as M. anisopliae; Pochonia spp. such as P. chlamydosporia.

Preferred mixing partners are abamectin and/or pymetrozine.

The compounds of the invention may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required.

An example of a rice selective herbicide which may be included is propanil. An example of a plant growth regulator for use in cotton is PIX™. Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) formulation.

For soil applications using compounds of formula I on sugar cane, including application on sugar cane propogation material such as buds, the following mixing partners are of particular interest:

insecticides selected from neonicotinoids, in particular thiamethoxam, imidacloprid and clothianidin, sulfoxaflor, abamectin, carbofuran, tefluthrin, fipronil, ethiprole, spinosad, lamda-cyhalothrin, bisamides, in particular chlorantraniliprole, cyantraniliprole, flubendiamide; optionally with fungicides selected from azoxystrobin, cyproconazole, thiabendazole, fluazinam, fludioxonil, mefenoxam, Sedaxane. Particular combinations of interest for sugar cane, particularly on sugar cane propogation material such as buds, include a compound of formula I with thiamethoxam and abamectin, a compound of formula I with thiamethoxam and cyantraniliprole, a compound of formula I with thiamethoxam and chlorantraniliprole. Further combinations of particular interestfor sugar cane include a compound selected from Tables 1 to 54 + thiamethoxam + abamectin + mefenoxam + fludioxonil + azoxystrobin + thiabendazole; a compound selected from Tables 1 to 54 + abamectin + mefenoxam + fludioxonil + azoxystrobin + thiabendazole, a compound selected from Tables 1 to 54+ thiamethoxam + mefenoxam + fludioxonil + azoxystrobin + thiabendazole, a compound selected from Tables 1 to 54+ thiamethoxam + abamectin + mefenoxam + fludioxonil + azoxystrobin + thiabendazole, a compound selected from Tables 1 to 54 + thiamethoxam + abamectin + fludioxonil + azoxystrobin + thiabendazole, a compound selected from Tables 1 to 54 + thiamethoxam + abamectin + mefenoxam + azoxystrobin + thiabendazole, a compound selected from Tables 1 to 54 + thiamethoxam + abamectin + mefenoxam + fludioxonil + thiabendazole, a compound selected from Tables 1 to 54 + thiamethoxam + abamectin + mefenoxam + fludioxonil + azoxystrobin. Example of ratios are below.

Unless otherwise stated the weight ratio of the compound of I with an additional active ingredient may generally be between 1000 : 1 and 1 : 1000. In other embodiments that weight ratio of A to B may be between 500 : 1 to 1 : 500, for example between 100 : 1 to 1 : 100, for example between 1 : 50 to 50 : 1, for example 1 : 20 to 20 : 1, for example 1 : 10 to 10: 1, for example 1 :5 to 5: 1, for example 1 :1, 1 :2, 1 :3, 1 :4, 1 :5, 2:1, 3: 1, 4: 1, or 5: 1.

In general, mixtures thiamethoxam, imidacloprid and clothianidin are of particular interest, as well as with pymetrozine and abamectin.

Compositions of the invention include those prepared by premixing prior to application, e.g. as a readymix or tankmix, or by simultaneous application or sequential application to the plant. In order to apply a compounds of the invention as an insecticide, acaricide, nematicide or molluscicide to a pest, a locus of pest, or to a plant susceptible to attack by a pest, compounds of the invention is usually formulated into a composition which includes, in addition to the compound of the invention, a suitable inert diluent or carrier and, optionally, a surface active agent (SFA). SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting). It is preferred that all compositions (both solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%>, of a compound of the invention. The composition is generally used for the control of pests such that a compound of the invention is applied at a rate of from O.lg to 10kg per hectare, preferably from lg to 6kg per hectare, more preferably from lg to 1kg per hectare.

Compositions comprising a compound of the invention can be chosen from a number of formulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro- emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations. The formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of the invention.

Dustable powders (DP) may be prepared by mixing a compound of the invention with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.

Soluble powders (SP) may be prepared by mixing a compound of the invention with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water

dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).

Wettable powders (WP) may be prepared by mixing a compound of the invention with one or more solid diluents or carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water dispersible granules (WG). Granules (GR) may be formed either by granulating a mixture of a compound of the invention and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of the invention (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of the invention (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if necessary. Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).

Dispersible Concentrates (DC) may be prepared by dissolving a compound of the invention in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent crystallization in a spray tank).

Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may be prepared by dissolving a compound of the invention in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as Cg-Cio fatty acid dimethylamide) and chlorinated hydrocarbons. An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment. Preparation of an EW involves obtaining a compound of the invention either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.

Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation. A compound of the invention is present initially in either the water or the solvent/SFA blend. Suitable solvents for use in MEs include those hereinbefore described for use in ECs or in EWs. An ME may be either an oil-in-water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation. An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion. Suspension concentrates (SC) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of the invention. SCs may be prepared by ball or bead milling the solid compound of the invention in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound. One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle. Alternatively, a compound of the invention may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.

Aerosol formulations comprise a compound of the invention and a suitable propellant (for example n-butane). A compound of the invention may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non- pressurized, hand-actuated spray pumps.

A compound of the invention may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.

Capsule suspensions (CS) may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerization stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of the invention and, optionally, a carrier or diluent therefor. The polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure. The compositions may provide for controlled release of the compound of the invention and they may be used for seed treatment. A compound of the invention may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.

A composition may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of the invention). Such additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of the invention).

A compound of the invention may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS). The preparations of DS, SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above. Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).

Wetting agents, dispersing agents and emulsifying agents may be surface SFAs of the cationic, anionic, amphoteric or non-ionic type. Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.

Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (for example sodium lauryl sulfate), salts of sulfonated aromatic compounds (for example sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalene sulfonate and mixtures of sodium di-z ^' opropyl- and tri-wopropyl-naphthalene sulfonates), ether sulfates, alcohol ether sulfates (for example sodium laureth-3 -sulfate), ether carboxylates (for example sodium laureth-3- carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally these products may be ethoxylated), sulfosuccinamates, paraffin or olefine sulfonates, taurates and lignosulfonates.

Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.

Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide);

alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.

Suitable suspending agents include hydrophilic colloids (such as polysaccharides,

polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).

Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use. These concentrates, which may include DCs, SCs, ECs, EWs, MEs, SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment. Such aqueous preparations may contain varying amounts of a compound of the invention (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.

A seed dressing formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in suitable seed dressing formulation form, e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds. Such seed dressing formulations are known in the art. Seed dressing formulations may contain the single active ingredients or the combination of active ingredients in encapsulated form, e.g. as slow release capsules or microcapsules. A typical a tank-mix formulation for seed treatment application comprises 0.25 to 80%, especially 1 to 75 %>, of the desired ingredients, and 99.75 to 20 %>, especially 99 to 25 %>, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40 %>, especially 0.5 to 30 %>, based on the tank-mix formulation. A typical pre -mix formulation for seed treatment application comprises 0.5 to 99.9 %>, especially 1 to 95 %>, of the desired ingredients, and 99.5 to 0.1 %>, especially 99 to 5 %>, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %>, especially 0.5 to 40 %>, based on the pre-mix formulation.

The rates of application of a plant propagation material treatment varies, for example, according to type of use, type of crop, the specific compound(s) and/or agent(s) used, and type of plant propagation material. The suitable rate is an effective amount to provide the desired action (such as disease or pest control) and can be determined by trials and routine experimentation known to one of ordinary skill in the art.

Generally for soil treatments, application rates can vary from 0.05 to 3 kg per hectare (g/ha) of ingredients. Generally for seed treatments, application rates can vary from 0.5 to l OOOg / 100kg of seeds of ingredients.

In general, the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20%> agriculturally acceptable surfactant and 10 to 99.99%) solid or liquid formulation inerts and adjuvant(s), the active agent consisting of at least the compound of formula I together with a compound of component B, and optionally other active agents, particularly microbiocides or conservatives or the like.

Concentrated forms of compositions generally contain in between about 2 and 80%>, preferably between about 5 and 70% by weight of active agent. Application forms of formulation may for example contain from 0.01 to 20%> by weight, preferably from 0.01 to 5% by weight of active agent. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations. Formulation Examples

The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

Dusts a) b) c)

Active ingredients 5 % 6 % 4 %

Talcum 95 % - - Kaolin - 94 % - mineral filler - - 96 %

Ready- for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.

Suspension concentrate

The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, seeds can be treated and protected against infestation by spraying, pouring or immersion.

Flowable concentrate for seed treatment

The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, seeds can be treated and protected against infestation by spraying, pouring or immersion.

The invention further pertains to a product for use in agriculture or horticulture comprising a capsule wherein at least a seed treated with the inventive compound is located. In another embodiment, the product comprises a capsule wherein at least a treated or untreated seed and the inventive compound are located.

Slow Release Capsule Suspension 28 parts of the inventive compound are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8: 1). This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredient. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in a suitable apparatus. The following non- limiting Examples illustrate the invention.

Table P provides compounds of formula la wherein R ^8a , R ^8b , R ^8c , A ¹ , B, R ^5a , R ^5b , A ² and X are defined in Table P

Table P

No R8a R8b R8c Al B R5a R5b A2 X

Al CI H CI 0 N CH3 H CH P3

A2 CI H CI CH2 N CH3 H CH P4

A3 CI CI CI O N CH3 H CH P4

A4 CI F CI O N CH3 H CH P4

A5 CI H CI O N CH3 H CH P7

A6 CI CI CI 0 N CH3 H CH P3

A7 CI H CI 0 N CI H CH P3

A8 CI CI CI 0 N Br H CH P7

A9 CI CI CI 0 N Br H CH P2

A10 CI H CI 0 N CF3 H CH P7

Al l CI CI CI 0 N CF3 H CH P7

A12 CF3 H H 0 N CH3 H CH P4

A13 CI CI CI 0 N CF3 H CH P2

A14 CI CI CI 0 N CF3 H CH P3

A15 CI CI CI 0 N CF3 H CH P4

A16 CI H CI 0 N CF3 H CH P3 A17 CI H CI 0 N CF3 H CH P4

A18 CI CI CI 0 N Br H CH P4

A19 CI CI CI 0 N Br H CH P3

A20 CI H CI 0 N Br H CH P2

A21 CI H CI 0 N Br H CH P4

A22 CI H CI 0 N Br H CH P3

A23 CF3 H H 0 N CH3 H CH P3

A24 CH=CH-

CF3 H CI 0 N CH P3

CH=CH

A25 CI F CI 0 N CI H CH P2

A26 CF3 F H 0 N CH3 H CH P4

A27 CF3 F H 0 N CH3 H CH P3

A28 CF3 F H 0 N CH3 H CH P2

A29 CI CI CI 0 N CH3 H CH P2

A30 CI F CI 0 N CH3 H CH P2

A31 CI H CI 0 N CI H CH P2

A32 CI F CI 0 N CH3 H CH P3

A33 CI F CI 0 N CI H CH P3

A34 CI CI CI 0 N CI H CH P3

A35 CI F CI 0 N CI H CH P4

A36 CI F CI 0 N CI H CH P7

A37 CI H CI 0 N CI H CH P4

A38 CI H CI CH2 N CH3 H CH P2

A39 CI H CI CH2 N CH3 H CH P3

A40 CI H CI CH2 N CH3 H CH P5

A41 CI H CI 0 N CF3 H CH P2

A42 CI CI CI 0 N CI H CH P4

A43 CI H CI 0 N CH3 H N P3

Table Q provides compounds of formula lb wherein R ^8a , R ^8b , R ^8c , R ⁷ , A ¹ , B, R ^5a , R ^5b , A ² and X are defined in Table Q

Table 0

No R8a R8b R8c R7 Al B R5a R5b A2 X

Bl CI H CI CF3 0 CH CH3 H CH P4

B2 CI H CI CF3 0 CH CH3 H CH P3

B3 CI H CI CF3 0 CH CH3 H CH P2

B4 CI H CI CF2C1 0 N CH3 H CH P4

B5 CI H CI CF2C1 0 N CH3 H CH P3

B6 CI H CI CF2C1 CH2 N CH3 H CH P4

B7 CI H CI CF2C1 CH2 N CH3 H CH P2

B8 CI H CI CF2C1 0 N CH3 H CH P2

B9 CI H CI CF3 0 N CH3 H CH P3

BIO CI H CI CF3 0 N Br H CH P4

Bl l CI CI CI CF3 CH2 N CH3 H CH P7

B12 CI Br CI CF3 0 N CH3 H CH P3

B13 CI Br CI CF3 0 N CH3 H CH P4

B14 CI H CI CF3 0 N CH3 H CH P2

B15 CI F CI CF3 CH2 N CH3 H CH P4

B16 CI F CI CF3 CH2 N CH3 H CH P3

B17 CI F CI CF3 CH2 N CH3 H CH P2

B18 CI CI CI CF3 CH2 N CH3 H CH P3

B19 CI F CI CF3 0 N CH3 H CH P4

B20 CI CI CI CF3 0 N CH3 H CH P2

B21 CI CI CI CF3 0 N CH3 H CH P3

B22 CI CI CI CF3 0 N CH3 H CH P4

B23 CI H CI CF3 0 N CH3 H CH P4

B24 CF3 H CF3 CF3 0 N CH3 H CH P3

B25 CI H CI CF3 0 N Br H CH P3

B26 CI Br CI CF3 0 N CH3 H CH P2

B27 CF3 CH=CH-

CI H CI 0 N CH P4

CH=CH

B28 CF3 H H CF3 0 N CH3 H CH P2 B29 CF3 H H CF3 0 N CH3 H CH P3

B30 CF3 H CF3 CF3 0 N CH3 H CH P2

B31 CI H CI CF3 0 N Br H CH P2

B32 CI H CI CF3 0 N CI H CH P2

B33 CI CI CI CF3 CH2 N CH3 H CH P5

B34 CI H CI CF3 CH2 N CH3 H CH P9

B35 CI H CI CF3 CH2 N CH3 H CH P7

B36 CF3 N CH=CH-

CI H CI CH2 CH P2

CH=CH

B37 CF3 N CH=CH-

CI H CI CH2 CH P3

CH=CH

B38 CI H CI CF3 0 N CF3 H CH P3

B39 CI H CI CF3 CH2 N CI H CH P4

B40 CI CI CI CF3 CH2 N CH3 H CH P4

B41 CI CI CI CF3 CH2 N CH3 H CH P2

B42 CI H CI CF3 0 N CH3 H CH P7

B43 Br H CI CF3 0 N CH3 H CH P3

B44 CF3 H CI CF3 0 N CH3 H CH P3

B45 CI CI H CF3 0 N CH3 H CH P3

B46 CI H CI CF3 0 N CI H CH P3

B47 CI H CI CF3 CH2 N CH3 H CH P3

B48 CI H F CF3 0 N CH3 H CH P3

B49 CF3 CH=CH-

CI H CI 0 N CH P3

CH=CH

B50 CF3 CH=CH-

CI H CI 0 N CH P2

CH=CH

B51 CI H F CF3 0 N CH3 H CH P2

B52 CI H CI CF3 0 N CF3 H CH P2

B53 CF3 H CI CF3 0 N CH3 H CH P4

B54 CF3 H CI CF3 0 N CH3 H CH P2

B55 CI H CI CF3 0 N CH3 H CH P9

B56 CI CI CI CF3 CH2 N CH3 H CH P9

B57 CF3 CI CF3 CF3 0 N CH3 H CH P2

B58 CF3 CI CF3 CF3 0 N CH3 H CH P3

B59 CF3 CI CF3 CF3 0 N CH3 H CH P4

B60 CI H CI CF3 CH2 N CH=CH- CH P4 CH=CH

B61 CI H CI CF3 CH2 N CI H CH P3

B62 CF3 H CF3 CF3 CH2 N CH3 H CH P3

B63 CI CI CF3 CF3 0 N CH3 H CH P2

B64 CI CI CF3 CF3 0 N CH3 H CH P3

B65 CI CI CF3 CF3 0 N CH3 H CH P4

B66 CF3 H CF3 CF3 CH2 N CH3 H CH P4

B67 CI H CI CF3 CH2 N CI H CH P2

B68 CI F CI CF3 0 N CH3 H CH P3

B69 CI F CI CF3 0 N CH3 H CH P2

B70 CI H CI CF3 0 N CH3 H CH P5

B71 Br H CI CF3 0 N CH3 H CH P2

B72 Br H CI CF3 0 N CH3 H CH P4

B73 F F F CF3 0 N CH3 H CH P2

B74 CI CI H CF3 0 N CH3 H CH P2

B75 CI CI H CF3 0 N CH3 H CH P4

B76 CI H CI CF3 0 N CI H CH P4

B77 CI F H CF3 0 N CH3 H CH P2

B78 CI F H CF3 0 N CH3 H CH P3

B79 CI F H CF3 0 N CH3 H CH P4

B80 F H CI CF3 0 N CH3 H CH P4

B81 CI H CI CF3 0 N CH3 H N P3

B82 CI H CI CF3 0 N CH3 H N P4

B83 CI H CI CF3 0 N CH3 H N P2

Table R provides compounds of formula Ic wherein R ^8a , R ^8b , R ^8c , R ^5a , R ^5b , A ² and X are defined in Table R

Table R

Example 1

Agriotes sp. (Wireworms)

Plastic beakers are prepared with 100 ml drench soil. Afterwards 12.5 ml compound solution is mixed in each plastic beaker and three maize seedlings are added. At the same day five wireworms are placed into each plastic beaker and these are covered up with a lid. Fourteen days after treatment the number of dead and moribund wireworms are evaluated. Wireworms are assessed as moribund if they were not able to burry into the soil in one hour after having been put onto the soil surface. The results show that the compounds of the invention are significantly more active against wireworms than structurally similar compounds.

Table A

Compound of the invention Reference compound

Table B

Com ound of the invention Reference compound

Compound Test Application rate | Control / / ppm %

Compound of the invention Agriotes sp. (Wireworms) 3 40

12.5 100

Reference compound Agriotes sp. (Wireworms) 3 0

12.5 0

Table C

Compound of the invention Reference compound

The following compounds gave at least 80% control against wireworms at an application rate of 12.5 ppm or less according to the above method: Al, A2, A3, A4, A5, A6, A7, Bl . B9, B23. (B9 and B23 were evaluated at 7 days after application.) No additional compounds from Table P, Q or R were tested against wireworms.

Example 2

Diabrotica balteata (Corn rootworm):

A 24-well microtiter plate (MTP) with artificial diet was treated with test solutions at an application rate of 200 ppm (concentration in well 18 ppm) by pipetting. After drying, the MTPs were infested with L2 larvae (6-10 per well). After an incubation period of 5 days, samples were checked for larval mortality.

The results show that the compounds of the invention are significantly more active against Diabrotica balteata than structurally similar compounds. Table E

Com ound of the invention

Table F

Compound of the invention Reference compound

Table G

Compound of the invention Diabrotica balteata (Corn 3 65

rootworm) 12.5 100

Reference compound Diabrotica balteata (Corn 3 nt

rootworm)

12.5 50

All compounds from Tables P (Al to A43), Q (Bl to B83) and R (CI to C5) gave at least 80% control against Diabrotica balteata at an application rate of 12.5 ppm or less according to the above method. Example 3

Diabrotica balteata (Corn rootworm):

Plastic boxes (17 x 27 x 22 cm) are filled with 8 L of drench soil and 6 maize seeds are sown into a furrow. 10ml of spray solution are applied with a hand sprayer into the furrow on the planted seeds and the furrow is closed afterwards. Two weeks after sowing each box is infested with 15 Diabrotica balteata L2 larvae. 6 days after infestation the plant damage is assessed. Plants are considered as either damaged or healthy. Dead plants, plants with hollow stems or entry holes are considered as damaged. The test is carried out with five replicates (boxes) per treatment. For in- furrow application the control is replicated five times with the application of water.

For the assessment as seed treatment 6 treated seeds are planted 0.5 cm deep into the soil. Exactly the same setup is used as with the in furrow treatment described above except that no spray solution is applied. For seed treatment the control is replicated five times without seed coating.

As six seeds are used per replicate, the total amount of active ingredient applied in furrow is six times the rate per seed in the seed treatment test. In that way the total amount of active ingredient used in both test system is adjusted to be directly comparable.

The results show that the potency is significantly higher when the active ingredient is applied in-furrow compared to as a seed treatment.

Compound Application rate / nig AI Reduction in plant Reduction in plant per seed damage compared to damage compared to control (in-furrow control (seed application) / % treatment) / %

Compound 1 0.5 95 64

0.1 52 30 Compound 2 0.5 95 20

0.1 79 10

Compound 3 0.5 100 35

0.1 100 15