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.

5 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.

10 Compounds from this class are broadly described in WO 2005/085216 (EP1731512), WO 2007/123853, WO 2007/075459, WO 2009/002809, 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, JP2008110971, JP2008133273, JP2009108046, WO 2009/022746, WO 2009/022746, WO 2010/032437, WO 2009/080250, WO 2010/020521, WO 2010/025998, WO 2010/020522, WO

15 2010/084067, WO 2010/086225, WO 2010/149506 and WO 2010/108733.

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. WO 2009/080250, WO 2010/020522, WO 2010/149506, WO 2011/101229 and WO 2012/045700) are highly effective at controlling soil pests, in particular corn rootworm, wireworms, grubs, in particular white grubs, termites,

20 subterraneous stinkbugs, cutworms, millipedes and broca gigante. 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

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

wherein -B'-B^B ³ - is -C=N-0-, -C=N-CH ₂ - , or -N-CH ₂ -CH ₂

R ¹ is trifluoromethyl, difluoromethyl or chlorodifluoromethyl;

30 R is group X

# X ² is C-X ⁶ or nitrogen;

X ¹ , X ³ and X ⁶ are independently hydrogen, halogen or trihalomethyl, wherein at least one of X ¹ , X ³ and

X ⁶ is not hydrogen;

A is selected from Al to A5

Y ¹ is C-R ⁶ , CH or nitrogen;

Y ² and Y ³ are independently CH or nitrogen;

wherein no more than two of Y ¹ , Y ² and Y ³ are nitrogen and wherein Y ² and Y ³ are not both nitrogen; R ⁵ is hydrogen, halogen, cyano, nitro, NH ₂ , Ci-C ₄ alkyl, Ci-C ₄ haloalkyl, C3-C ₅ cycloalkyl, C ₃ - C ₅ halocycloalkyl, Ci-C ₂ alkoxy, or Ci-C ₂ haloalkoxy; providing that when A is A3 or A4 R ⁵ is not hydrogen;

R ⁶ when present together with R ⁵ forms a -CH=CH-CH=CH- bridge;

R ⁷ is C _r C ₄ alkyl;

R ⁸ is Ci-C ₄ alkyl, C _r C ₄ haloalkyl, Ci-C ₄ alkoxy(Ci-C ₄ )alkyl, Ci-C ₄ alkylthio(C _r C ₄ )alkyl, C _r

C ₄ alkylsulfmyl(Ci-C ₄ )alkyl, Ci-C ₄ alkylsulfonyl(Ci-C ₄ )alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl(C _r C ₄ )alkyl-, or tetrahydrofuranyl;

R ⁹ is Ci-C ₄ alkyl, C _r C ₄ haloalkyl, C _r C ₄ alkyl-0-CH ₂ -, Ci-C ₄ haloalkyl-0-CH ₂ -,C ₃ -C ₆ cycloalkyl, C ₃ - C ₆ cycloalkyl-CH ₂ -, C _r C ₄ alkyl-S-CH ₂ -, C _r C ₄ alkyl-S(0)-CH ₂ -, or C _r C ₄ alkyl-S(0 ₂ )-CH ₂ ;

each Z is independently halogen, Ci-Ci ₂ alkyl or Ci-Ci ₂ alkyl substituted by one to five R ¹² , nitro, Cp

Ci ₂ alkoxy or Ci-Ci ₂ alkoxy substituted by one to five R ¹² cyano, Ci-Ci ₂ alkylsulfinyl, Ci-Ci ₂ alkylsulfonyl, Ci-Ci ₂ haloalkylsulfinyl, Ci-Ci ₂ haloalkylsulfonyl, hydroxyl or thiol;

each R ¹² is halogen, cyano, nitro, hydroxy, CpCgalkoxy-, CpCghaloalkoxy-, mercapto, CpCgalkylthio-, or Ci-Cghaloalkylthio; and

k is 0, 1,2 or 3;

wherein when the pest is corn rootworm, R ⁸ is cyclopropyl when A is A2 and -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -;

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), preferably corn rootworm or wireworms, most preferably corn rootworm.

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 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 invention preferably relates to methods of controlling and/or preventing corn rootworm and/ or wireworms, most preferably corn rootworm.

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, 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.

The preferences for B ¹ , B ² , B ³ , R ¹ , R ² , Y ¹ , Y ² , Y ³ , R ⁵ , R ⁶ R ⁷ , R ⁸ , R ⁹ , R ¹² , X ¹ X ² , X ³ , X ⁶ , Z and k are, in any combination, as described below.

Preferably R ¹ is trifluoromethyl, or chlorodifluoromethyl, most preferably trifluoromethyl.

Preferably X ¹ , X ³ and X ⁶ are independently hydrogen, halogen or trifluoromethyl, wherein at least two of X ¹ , X ³ and X ⁶ are not hydrogen. More preferably X ¹ , X ³ and X ⁶ are independently hydrogen, chloro, bromo or trifluoromethyl, wherein at least two of X ¹ , X ³ and X ⁶ are not hydrogen. Preferably at least two of X ¹ , X ³ and X ⁶ are chloro, bromo or trifluoromethyl.

In one group of compounds R ² 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-, 2,6- dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3-bromo-5-(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-, 2,6-dichloro-4- pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5- (trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-, more preferably R is 3,5-dichloro- phenyl, 3,5-dichloro-4-fluorophenyl- or 3,4,5-trichloro-phenyl, most preferably 3,5-dichloro-phenyl.

Preferably Y ¹ is CH, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is CH, Y ³ is N. Most preferably Y ¹ is CH, Y ² is CH, and Y ³ is CH.

Preferably R ⁵ is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, more preferably R ⁵ is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, nitro, cyano, cyclopropyl, most preferably R ⁵ is hydrogen, cyano, chloro, bromo, fluoro, methyl, or trifluoromethyl.

Preferably R ⁸ is C _r C ₄ alkyl, C _r C ₄ haloalkyl, Ci-C ₄ alkyl-0-CH ₂ -, C _r C ₄ haloalkyl-0-CH ₂ -,C ₃ -

Cgcycloalkyl, C ₃ -C ₆ cycloalkyl-CH ₂ -, C _r C ₄ alkyl-S(0)-CH ₂ -, Ci-C ₄ alkyl-S(0 ₂ )-CH ₂ -, more preferably C _r Qalkyl, C _r C ₄ alkyl-0-CH ₂ -, C _r C ₄ alkyl-S-CH ₂ -, C _r C ₄ alkyl-SO-CH ₂ -, C _r C ₄ alkyl-S0 ₂ -CH ₂ -, C ₃ - C ₄ cycloalkyl, or C3-C ₄ cycloalkyl-CH ₂ -, most preferably R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0- CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -.

Preferably R ⁹ is C _r C ₄ alkyl, C _r C ₄ haloalkyl, C _r C ₄ alkyl-0-CH ₂ -, C _r C ₄ haloalkyl-0-CH ₂ -,C ₃ -

Cgcycloalkyl, C ₃ -C ₆ cycloalkyl-CH ₂ -, C _r C ₄ alkyl-S(0)-CH ₂ -, C _r C ₄ alkyl-S(0 ₂ )-CH ₂ -, more preferably C _r C ₄ alkyl, C _r C ₄ haloalkyl, C _r C ₄ alkyl-0-CH ₂ -, C _r C ₄ haloalkyl-0-CH ₂ -,C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl- CH ₂ -, more preferably Ci-C ₄ alkyl, Ci-C ₄ haloalkyl or C ₃ -C ₄ cycloalkyl, more preferably methyl, ethyl, n- propyl, CF ₃ CH ₂ - or cyclopropyl, even more preferably ethyl, CF ₃ CH ₂ - or cyclopropyl.

Preferably each Z is independently halogen, cyano, Ci-C ₄ alkyl, Ci-C ₄ haloalkyl, Ci-C ₄ alkoxy, or

Ci-C ₄ haloalkoxy, most preferably each Z is independently hydrogen, cyano, halogen, methyl, halomethyl, methoxy or halomethoxy, most preferably cyano or trifluoromethyl.

Each R ¹² is preferably bromo, chloro, fluoro, methoxy, or methylthio, most preferably chloro, fluoro, or methoxy

Preferably k is 0 or 1.

In one group of compounds -B ¹ -B ² -B ³ - is -C=N-0-.

In another group of compounds -B ¹ -B ² -B ³ - is -C=N-CH ₂ -.

In another group of compounds -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -.

In another group of compounds Y ¹ is C-R ⁶ and R ⁶ together with R ⁵ forms a -CH=CH-CH=CH- bridge.

In one embodiment the compound of formula I is a compound of formula IA

(IA) wherein B ¹ , B ² , B ³ , R ¹ , R ² , Y ¹ , Y ² , Y ³ , R ⁵ and R ⁸ are as defined for a compound of formula I,

wherein when the pest is corn rootworm, R ⁸ is cyclopropyl when -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -.

In compounds of formula IA preferred definitions of B ¹ , B ² , B ³ , R ¹ , R ² , Y ¹ , Y ² , Y ³ , R ⁵ and R ⁸ are, in any combination, as set out below:

Preferably R ¹ is trifluoromethyl, or chlorodifluoromethyl, most preferably trifluoromethyl.

Preferably X ¹ , X ³ and X ⁶ are independently hydrogen, halogen or trifluoromethyl, wherein at least two of X ¹ , X ³ and X ⁶ are not hydrogen. More preferably X ¹ , X ³ and X ⁶ are independently hydrogen, chloro, bromo or trifluoromethyl, wherein at least two of X ¹ , X ³ and X ⁶ are not hydrogen. Preferably at least two of X ¹ , X ³ and X ⁶ are chloro, bromo or trifluoromethyl.

In one group of compounds R ² 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-, 2,6- dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3-bromo-5-(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-, 2,6-dichloro-4- pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5- (trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-, more preferably R ² is 3,5-dichloro- phenyl or 3,4,5-trichloro-phenyl, most preferably 3,5-dichloro-phenyl.

Preferably Y ¹ is CH, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is CH, Y ³ is N. Most preferably Y ¹ is CH, Y ² is CH, and Y ³ is CH.

Preferably R ⁵ is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, more preferably R ⁵ is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, nitro, cyano, cyclopropyl, more preferably R ⁵ is hydrogen, cyano, chloro, bromo, fluoro, methyl, or trifluoromethyl, even more preferably hydrogen, chloro, bromo, methyl or trifluoromethyl, most preferably chloro, bromo, fluoro or methyl.

Preferably R ⁸ is C _r C ₄ alkyl, C _r C ₄ haloalkyl, Ci-C ₄ alkyl-0-CH ₂ -, C _r C ₄ haloalkyl-0-CH ₂ -,C ₃ - Cgcycloalkyl, C ₃ -C ₆ cycloalkyl-CH ₂ -, C _r C ₄ alkyl-S(0)-CH ₂ -, C _r C ₄ alkyl-S(0 ₂ )-CH ₂ -, more preferably C _r C ₄ alkyl, C _r C ₄ alkyl-0-CH ₂ -, C _r C ₄ alkyl-S-CH ₂ -, C _r C ₄ alkyl-SO-CH ₂ -, C _r C ₄ alkyl-S0 ₂ -CH ₂ -, C ₃ - C ₄ cycloalkyl, or C3-C ₄ cycloalkyl-CH ₂ -, more preferably R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0- CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, most preferably n-propyl or cyclopropropyl.

In one group of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-0-.

In another group of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-0- and Y ¹ is CH, Y ² is CH, Y ³ is CH. In another group of compounds of formula IA -B'-B^B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH and R ¹ is CF ₃ .

In another group of compounds of formula IA -B'-B^B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ and R ⁵ is chloro, bromo, fluoro or methyl.

In another group of compounds of formula IA -B'-B^B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is

CH, R ¹ is CF ₃ , and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl.

In another group of compounds of formula IA -B'-B^B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is chloro, bromo, fluoro or methyl and R ⁸ is methyl, ethyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably cyclopropropyl.

In another group of compounds of formula IA -B'-B^B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is chloro, bromo, fluoro or methyl, R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0- CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl, and R ² is 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-, 2,6-dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)- 4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-.

In one group of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-CH ₂ -.

In another group of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-CH ₂ - and Y ¹ is CH, Y ² is CH, Y ³ is CH.

In another group of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH and R ¹ is CF ₃ .

In another group of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ and R ⁵ is chloro, bromo, fluoro or methyl.

In another group of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ - , CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl.

In another group of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is chloro, bromo, fluoro or methyl and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ - 0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl.

In another group of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is chloro, bromo, fluoro or methyl and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ - 0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl, and R ² is 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-, 2,6-dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)- 4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-.

In one group of compounds of formula IA -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -.

In another group of compounds of formula IA -B'-B^B ³ - is -N-CH ₂ -CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH.

In another group of compounds of formula IA -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH and R ¹ is CF ₃ .

In another group of compounds of formula IA -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -, Y ¹ is CH, Y ² is CH,

Y ³ is CH, R ¹ is CF ₃ and R ⁵ is chloro, bromo, fluoro or methyl.

In another group of compounds of formula IA -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)- CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or

cyclopropropyl.

In another group of compounds of formula IA -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is chloro, bromo, fluoro or methyl and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ - , preferably n-propyl or cyclopropropyl.

In another group of compounds of formula IA -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH,

Y ³ is CH, R ¹ is CF ₃ , R ⁵ is chloro, bromo, fluoro or methyl, R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ - O-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl, and R ² is 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-, 2,6-dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)- 4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-.

In another group of compounds of formula IA R ⁵ is chloro, bromo, fluoro or methyl and

R ⁸ methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl.

In another group of compounds of formula IA R ⁵ is chloro, bromo, fluoro or methyl;

R ⁸ methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl, R ¹ is CF ₃ , -B ¹ -B ² -B ³ is -C=N-0- or -C=N-CH ₂ -, Y ¹ , Y ² and Y ³ are CH, and R ⁵ is chloro or methyl.

In a further preferred embodiment of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-0-, R ¹ is trifluoromethyl, Y ¹ , Y ² and Y ³ are CH, R ⁵ is chloro, and R ⁸ is n-propyl. In a further preferred embodiment of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-0-, R ¹ is trifluoromethyl, Y ¹ , Y ² and Y ³ are CH, R ⁵ is chloro, and R ⁸ is n-propyl.

In a further preferred embodiment of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-0-, R ¹ is trifluoromethyl, R ² is 3-bromo-5-trifluoromethylphenyl, Y ¹ , Y ² and Y ³ are CH and R ⁸ is n-propyl.

In a further preferred embodiment of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-0-, R ¹ is trifluoromethyl, R ² is 3-bromo-5-trifluoromethylphenyl, Y ¹ , Y ² and Y ³ are CH and R ⁵ is chloro.

In a further preferred embodiment of compounds of formula IA -B ¹ -B ² -B ³ - is -C=N-0-, R ¹ is trifluoromethyl, R 2 is 3-bromo-5-trifluoromethylphenyl, Y 1 , Y 2 and Y 3 are CH, R 5 is chloro, and R 8 is n- propyl.In one embodiment the compound of formula I is a compound of formula IB

wherein B 1 , RV' and R 8° are as defined for a compound of formula I

In compounds of formula IB preferred definitions of B ¹ , B ² , B ³ , R ¹ , R ² , Y ¹ , Y ² , Y ³ , R ⁷ and R ⁸ are, in any combination, as set out below.

Preferably R ¹ is trifluoromethyl, or chlorodifluoromethyl, most preferably trifluoromethyl.

Preferably X ¹ , X ³ and X ⁶ are independently hydrogen, halogen or trifluoromethyl, wherein at least two of X ¹ , X ³ and X ⁶ are not hydrogen. More preferably X ¹ , X ³ and X ⁶ are independently hydrogen, chloro, bromo or trifluoromethyl, wherein at least two of X ¹ , X ³ and X ⁶ are not hydrogen. Preferably at least two of X ¹ , X ³ and X ⁶ are chloro, bromo or trifluoromethyl.

In one group of compounds R ² 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-, 2,6- dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3-bromo-5-(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-, 2,6-dichloro-4- pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5- (trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-, more preferably R ² is 3,5-dichlorophenyl or 3,4,5-trichloro-phenyl, most preferably 3,5-dichloro-phenyl.

Preferably Y ¹ is CH, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is CH, Y ³ is N. Most preferably Y ¹ is CH, Y ² is CH, and Y ³ is CH. Preferably R ⁷ is methyl.

Preferably R ⁸ is C _r C ₄ alkyl, C _r C ₄ haloalkyl, Ci-C ₄ alkyl-0-CH ₂ -, C _r C ₄ haloalkyl-0-CH ₂ -,C ₃ - Cgcycloalkyl, C ₃ -C ₆ cycloalkyl-CH ₂ -, C _r C ₄ alkyl-S(0)-CH ₂ -, Ci-C ₄ alkyl-S(0 ₂ )-CH ₂ -, more preferably C _r Qalkyl, C _r C ₄ alkyl-0-CH ₂ -, C _r C ₄ alkyl-S-CH ₂ -, C _r C ₄ alkyl-SO-CH ₂ -, C _r C ₄ alkyl-S0 ₂ -CH ₂ -, C ₃ - C ₄ cycloalkyl, or C3-C ₄ cycloalkyl-CH ₂ -, more preferably R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0- CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, most preferably n-propyl or cyclopropyl.

In one group of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-0-.

In another group of compounds of formula IB -B'-B^B ³ - is -C=N-0- and Y ¹ is CH, Y ² is CH, Y ³ is CH.

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-0- , Y ¹ is CH, Y ² is CH, Y ³ is CH and R ¹ is CF ₃ .

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-0- , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ and R ⁷ is methyl.

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-0- , Y ¹ is CH, Y ² is CH, Y ³ is

CH, R ¹ is CF ₃ , and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl.

In another group of compounds of -B ¹ -B ² -B ³ - is -C=N-0- , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁷ is methyl and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)- CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or

cyclopropropyl.

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-0- , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁷ is methyl, R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ - S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl, and R ² is 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-, 2,6- dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5- (trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-.

In one group of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-CH ₂ -.

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-CH ₂ - and Y ¹ is CH, Y ² is CH,

Y ³ is CH.

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH and R ¹ is CF ₃ .

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ and R ⁷ is methyl. In another group of compounds of formula IB -β'-Β^Β ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ - , CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl.

In another group of compounds of formula IB -β'-Β^Β ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁷ is methyl and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl.

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁷ is methyl, R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ - S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl, and R ² is 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-, 2,6- dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5- (trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-.

In one group of compounds of formula IB -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -.

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - and Y ¹ is CH, Y ² is CH, Y ³ is CH.

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH and R ¹ is CF ₃ .

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH,

Y ³ is CH, R ¹ is CF ₃ and R ⁷ is methyl.

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)- CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or

cyclopropropyl.

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁷ is methyl and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl.

In another group of compounds of formula IB -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH,

Y ³ is CH, R ¹ is CF ₃ , R ⁷ is methyl, R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl, and R ² is 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-, 2,6- dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5- (trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-. In another group of compounds of formula IB R ⁷ is methyl, and R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl.

In another group of compounds of formula IB R ⁷ is methyl, R ⁸ is methyl, ethyl, n-propyl, isopropyl, CH ₃ -0-CH ₂ -, CH ₃ -S-CH ₂ -, CH ₃ -S(0)-CH ₂ -, CH ₃ -S0 ₂ -CH ₂ -, cyclobutyl, cyclopropyl or cyclopropyl-CH ₂ -, preferably n-propyl or cyclopropropyl, R ¹ is CF ₃ , -B ¹ -B ² -B ³ - is -C=N-0-, -C=N-CH ₂ - or -N-CH ₂ -CH ₂ -, and Y ¹ , Y ² and Y ³ are CH.

In a further preferred embodiment of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-0-, R ¹ is

1 2 3 5 V 8

trifluoromethyl, Y , Y and Y are CH; R is chloro, R is methyl and R is n-propyl.

In a further preferred embodiment of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-0-, R ¹ is

1 2 3 5 V 8

trifluoromethyl, Y , Y and Y are CH; R is chloro, R is methyl and R is n-propyl.

In a further preferred embodiment of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-0-, R ¹ is trifluoromethyl, R 2 is 3-bromo-5-trifluoromethylphenyl, Y 1 , Y2 and Y 3 are CH, RV is methyl and R 8 is n- propyl.

In a further preferred embodiment of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-0-, R ¹ is trifluoromethyl, R 2 is 3-bromo-5-trifluoromethylphenyl, Y 1 , Y 2 and Y 3 are CH, R 5 is chloro and R V is methyl.

In a further preferred embodiment of compounds of formula IB -B ¹ -B ² -B ³ - is -C=N-0-, R ¹ is trifluoromethyl, R 2 is 3-bromo-5-trifluoromethylphenyl, Y 1 , Y 2 and Y 3 are CH, R 5 is chloro, R V is methyl and R ⁸ is n-propyl.

In one embodiment the compound of formula I is a compound of formula IC

wherein B 1 , 5

R ^D Z and k are as defined for a compound of formula I

In compounds of formula IC preferred definitions of B ¹ , B ² , B ³ , R ¹ , R ² , Y ¹ , Y ² , Y ³ , R ⁵ , Z and k are, in any combination, as set out below.

Preferably R ¹ is trifluoromethyl, or chlorodifluoromethyl, most preferably trifluoromethyl.

Preferably X ¹ , X ³ and X ⁶ are independently hydrogen, halogen or trifluoromethyl, wherein at least two of X ¹ , X ³ and X ⁶ are not hydrogen. More preferably X ¹ , X ³ and X ⁶ are independently hydrogen, chloro, bromo or trifluoromethyl, wherein at least two of X ¹ , X ³ and X ⁶ are not hydrogen. Preferably at least two of X ¹ , X ³ and X ⁶ are chloro, bromo or trifluoromethyl.

In one group of compounds R ² 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-, 2,6- dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3-bromo-5-(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-, 2,6-dichloro-4- pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5- (trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-, more preferably R ² is 3,5-dichloro- phenyl or 3,4,5-trichloro-phenyl, most preferably 3,5-dichloro-phenyl.

Preferably Y ¹ is CH, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is CH, Y ³ is N. Most preferably Y ¹ is CH, Y ² is CH, and Y ³ is CH.

Preferably R ⁵ is chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, more preferably R ⁵ is chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, nitro, cyano, cyclopropyl, even more preferably R ⁵ is cyano, chloro, bromo, fluoro, methyl, or trifluoromethyl, most preferably cyano.

Preferably each Z is independently halogen, cyano, Ci-C ₄ alkyl, Ci-C ₄ alkoxy, or Ci-C ihaloalkoxy, more preferably each Z is independently hydrogen, cyano, halogen, methyl, halomethyl, methoxy or halomethoxy, most preferably cyano or trifluoromethyl.

Preferably k is 0 or 1.

In one group of compounds of formula IC -B ¹ -B ² -B ³ - is -C=N-0-.

In another group of compounds of formula IC -B ¹ -B ² -B ³ - is -C=N-0-and Y ¹ is CH, Y ² is CH, Y ³ is CH.

In another group of compounds of formula IC -B ¹ -B ² -B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH and R ¹ is CF ₃ .

In another group of compounds of formula IC -B ¹ -B ² -B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ and R ⁵ is cyano.

In another group of compounds of formula IC -B ¹ -B ² -B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , and k is 0 or k is 1 and Z is cyano or trifluoromethyl.

In another group of compounds of formula IC -B ¹ -B ² -B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is

CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 and Z is cyano or trifluoromethyl.

In another group of compounds of formula IC -B ¹ -B ² -B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 and Z is cyano or trifluoromethyl and R ² is 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-, 2,6-dichloro-4-pyridyl-, 2,6- bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5- dibromophenyl-, or 3,4-dichlorophenyl-. In one group of compounds of formula IC -B ¹ -B ² -B ³ - is -C=N-CH ₂ -.

In another group of compounds of formula IC -B'-B^B ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH.

In another group of compounds of formula IC -B'-B^B ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH and R ¹ is CF ₃ .

In another group of compounds of formula IC -B'-B^B ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ and R ⁵ is cyano.

In another group of compounds of formula IC -B'-B^B ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , and k is 0 or k is 1 and Z is cyano or trifluoromethyl.

In another group of compounds of formula IC -B'-B^B ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 and Z is cyano or trifluoromethyl.

In another group of compounds of formula IC -B'-B^B ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 and Z is cyano or trifluoromethyl and R ² is 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-, 2,6-dichloro-4-pyridyl-, 2,6- bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5- dibromophenyl-, or 3,4-dichlorophenyl-.

In one group of compounds of formula IC -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -.

In another group of compounds of formula IC -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - and Y ¹ is CH, Y ² is CH, Y ³ is CH.

In another group of compounds of formula IC -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -, Y ¹ is CH, Y ² is CH, Y is CH and R ¹ is CF ₃ .

In another group of compounds of formula IC -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -, Y ¹ is CH, Y ² is CH, Y is CH, R ¹ is CF ₃ and R ⁵ is cyano.

In another group of compounds of formula IC -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -, Y ¹ is CH, Y ² is CH, Y is CH, R ¹ is CF ₃ , and k is 0 or k is 1 and Z is cyano or trifluoromethyl.

In another group of compounds of formula IC -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 and Z is cyano or trifluoromethyl.

In another group of compounds of formula IC -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 and Z is cyano or trifluoromethyl and R ² is 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-, 2,6-dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-.

In another group of compounds of formula IC R ⁵ is cyano, k is 0 or 1 and Z is cyano or trifluoromethyl. In another group of compounds of formula IC R ⁵ is cyano, R ¹ is CF ₃ , -B ¹ -B ² -B ³ - is -C=N-0- or - C=N-CH ₂ -, Y ¹ , Y ² and Y ³ are CH, and k is 0.

In one embodiment the compound of formula I is a compound of formula ID

wherein B 1 , B2, R5 ^D Z and k are as defined for a compound of formula I

In compounds of formula ID preferred definitions of B ¹ , B ² , B ³ , R ¹ , R ² , Y ¹ , Y ² , Y ³ , R ⁵ Z and k are, in any combination, as set out below.

Preferably R ¹ is trifluoromethyl, or chlorodifluoromethyl, most preferably trifluoromethyl.

Preferably X ¹ , X ³ and X ⁶ are independently hydrogen, halogen or trifluoromethyl, wherein at least two of X ¹ , X ³ and X ⁶ are not hydrogen. More preferably X ¹ , X ³ and X ⁶ are independently hydrogen, chloro, bromo or trifluoromethyl, wherein at least two of X ¹ , X ³ and X ⁶ are not hydrogen. Preferably at least two of X ¹ , X ³ and X ⁶ are chloro, bromo or trifluoromethyl.

In one group of compounds R ² 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-, 2,6- dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3-bromo-5-(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-, 2,6-dichloro-4- pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5- (trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-, more preferably R ² is 3,5-dichlorophenyl or 3,4,5-trichloro-phenyl, most preferably 3,5-dichloro-phenyl.

Preferably Y ¹ is CH, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is CH, Y ³ is N. Most preferably Y ¹ is CH, Y ² is CH, and Y ³ is CH.

Preferably R ⁵ is chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, more preferably R ⁵ is chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, nitro, cyano, cyclopropyl, even more preferably R ⁵ is cyano, chloro, bromo, fluoro, methyl, or trifluoromethyl, most preferably cyano. Preferably each Z is independently halogen, cyano, Ci-C ₄ alkyl, Ci-C ₄ alkoxy, or Ci-C ihaloalkoxy, more preferably each Z is independently hydrogen, cyano, halogen, methyl, halomethyl, methoxy or halomethoxy, most preferably cyano or trifluoromethyl.

Preferably k is 0 or 1 , more preferably 1. When k is 1 preferably Z is attached to the 4 position of the imidazole moiety as indicated below:

In one group of compounds of formula ID -B ¹ -B ² -B ³ - is -C=N-0-.

In another group of compounds of formula ID -B'-B^B ³ - is -C=N-0-and Y ¹ is CH, Y ² is CH, Y ³ is CH.

In another group of compounds of formula ID -B'-B^B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is

CH and R ¹ is CF ₃ .

In another group of compounds of formula ID -B'-B^B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ and R ⁵ is cyano.

In another group of compounds of formula ID -B'-B^B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , and k is 0 or k is 1 and Z is cyano or trifluoromethyl.

In another group of compounds of formula ID -B'-B^B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 and Z is cyano or trifluoromethyl.

In another group of compounds of formula ID -B'-B^B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 , preferably 1 , and Z is cyano or trifluoromethyl, and when k is 1 , Z is attached to the 4 position of the imidazole moiety.

In another group of compounds of formula ID -B'-B^B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 and Z is cyano or trifluoromethyl and R ² is 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-, 2,6-dichloro-4-pyridyl-, 2,6- bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5- dibromophenyl-, or 3,4-dichlorophenyl-.

another group of compounds of formula ID -B ¹ -B ² -B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or 1 or k is 1, preferably 1, and Z is cyano or trifluoromethyl and R ² is 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-, 2,6-dichloro-4-pyridyl-,

2.6- bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-, and when k is 1, Z is attached to the 4 position of the imidazole moiety.

In one group of compounds of formula ID -B ¹ -B ² -B ³ - is -C=N-CH ₂ -. In another group of compounds of formula ID -B'-B^B ³ - is -C=N-CH ₂ - and Y ¹ is CH, Y ² is CH, Y ³ is CH.

In another group of compounds of formula ID -β'-Β^Β ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH and R ¹ is CF ₃ .

In another group of compounds of formula ID -β'-Β^Β ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ and R ⁵ is cyano.

In another group of compounds of formula ID -β'-Β^Β ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , and k is 0 or k is 1 and Z is cyano or trifluoromethyl.

In another group of compounds of formula ID -β'-Β^Β ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 and Z is cyano or trifluoromethyl.

In another group of compounds of formula ID -β'-Β^Β ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 , preferably 1 , and Z is cyano or trifluoromethyl, and when k is 1 , Z is attached to the 4 position of the imidazole moiety.

In another group of compounds of formula ID -β'-Β^Β ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 and Z is cyano or trifluoromethyl and R ² is 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-, 2,6-dichloro-4-pyridyl-, 2,6- bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5- dibromophenyl-, or 3,4-dichlorophenyl-.

In another group of compounds of formula ID -B ¹ -B ² -B ³ - is -C=N-CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 , preferably 1 , and Z is cyano or trifluoromethyl and R ² is 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-, 2,6-dichloro-4-pyridyl-,

2.6- bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-, and when k is 1, Z is attached to the 4 position of the imidazole moiety.

In one group of compounds of formula ID -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -.

In another group of compounds of formula ID -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - and Y ¹ is CH, Y ² is CH, Y ³ is CH.

In another group of compounds of formula ID -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH,

Y ³ is CH and R ¹ is CF ₃ .

In another group of compounds of formula ID -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ and R ⁵ is cyano.

In another group of compounds of formula ID -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , and k is 0 or k is 1 and Z is cyano or trifluoromethyl.

In another group of compounds of formula ID -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 and Z is cyano or trifluoromethyl. In another group of compounds of formula ID -B'-B^B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 , preferably 1 , and Z is cyano or trifluoromethyl, and when k is 1 , Z is attached to the 4 position of the imidazole moiety.

In another group of compounds of formula ID -B'-B^B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 and Z is cyano or trifluoromethyl and R ² is 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-, 2,6-dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-,

3.5- dibromophenyl-, or 3,4-dichlorophenyl-.

In another group of compounds of formula ID -B'-B^B ³ - is -N-CH ₂ -CH ₂ - , Y ¹ is CH, Y ² is CH,

Y ³ is CH, R ¹ is CF ₃ , R ⁵ is cyano and k is 0 or k is 1 , preferably 1 , and Z is cyano or trifluoromethyl and R ² is 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-, 2,6-dichloro-4-pyridyl-,

2.6- bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-, and when k is 1, Z is attached to the 4 position of the imidazole moiety.

In another group of compounds of formula D R ⁵ is cyano, k is 0 or 1 and Z is cyano or trifluoromethyl.

In another group of compounds of formula ID R ⁵ is cyano, k is 0 or 1 , preferably 1 , and Z is cyano or trifluoromethyl, and when k is 1 , Z is attached to the 4 position of the imidazole moiety.

In another group of compounds of formula ID R ⁵ is cyano, k is 0 or 1 and Z is cyano or trifluoromethyl, R ¹ is CF ₃ , -B ¹ -B ² -B ³ - is -C=N-0- or -C=N-CH ₂ -, Y ¹ , Y ² and Y ³ are CH.

In another group of compounds of formula ID R ⁵ is cyano, k is 0 or 1 , preferably 1 , and Z is cyano or trifluoromethyl, R ¹ is CF ₃ , -B ¹ -B ² -B ³ - is -C=N-0- or -C=N-CH ₂ -, Y ¹ , Y ² and Y ³ are CH, and when k is 1 , Z is attached to the 4 position of the imidazole moiety.

In one embodiment the compound of formula I is a compound of formula IE

wherein B 1 , and Y 3 ^J are as defined for a compound of formula I

In compounds of formula ID preferred definitions of B 1, B2, B3, R 1, R2, R9, Y1, Y2, Y3, are, in any combination, as set out below

Preferably R ¹ is trifluoromethyl, or chlorodifluoromethyl, most preferably trifluoromethyl. Preferably X ¹ , X ³ and X ⁶ are independently hydrogen, halogen or trifluoromethyl, wherein at least two of X ¹ , X ³ and X ⁶ are not hydrogen. More preferably X ¹ , X ³ and X ⁶ are independently hydrogen, chloro, bromo or trifluoromethyl, wherein at least two of X ¹ , X ³ and X ⁶ are not hydrogen. Preferably at least two of X ¹ , X ³ and X ⁶ are chloro, bromo or trifluoromethyl.

In one group of compounds R ² 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-, 2,6- dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3-bromo-5-(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-, 2,6-dichloro-4- pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5- (trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-, more preferably R ² is 3,5-dichloro- phenyl or 3,4,5-trichloro-phenyl, most preferably 3,5-dichloro-phenyl.

Preferably Y ¹ is CH, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is CH, Y ³ is N. Most preferably Y ¹ is CH, Y ² is CH, and Y ³ is CH.

Preferably R ⁹ is C _r C ₄ alkyl, C _r C ₄ haloalkyl, Ci-C ₄ alkyl-0-CH ₂ -, C _r C ₄ haloalkyl-0-CH ₂ -,C ₃ - Cgcycloalkyl, C ₃ -C ₆ cycloalkyl-CH ₂ -, C _r C ₄ alkyl-S(0)-CH ₂ -, Ci-C ₄ alkyl-S(0 ₂ )-CH ₂ -, more preferably C _r C ₄ alkyl, C _r C ₄ haloalkyl, C _r C ₄ alkyl-0-CH ₂ -, C _r C ₄ haloalkyl-0-CH ₂ -,C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl- CH ₂ -, more preferably Ci-C ₄ alkyl, Ci-C ₄ haloalkyl or C ₃ -C ₄ cycloalkyl, more preferably methyl, ethyl,propyl, CF ₃ CH ₂ - or cyclopropyl, even more preferably ethyl, CF ₃ CH ₂ - or cyclopropyl.

Preferably Y ¹ is CH, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is CH, Y ³ is CH, or Y ¹ is N, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is N, Y ³ is CH, or Y ¹ is CH, Y ² is CH, Y ³ is N. Preferably Y ¹ is CH, Y ² is CH, and Y ³ is CH.

In one group of compounds of formula IE -B ¹ -B ² -B ³ - is -C=N-0-.

In another group of compounds of formula IE -B ¹ -B ² -B ³ - is -C=N-0-and Y ¹ is CH, Y ² is CH, Y ³ is CH.

In another group of compounds of formula IE -B ¹ -B ² -B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is

CH and R ¹ is CF ₃ .

In another group of compounds of formula IE -B ¹ -B ² -B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ and R ⁹ is C _r C ₄ alkyl.

In another group of compounds of formula IE -B ¹ -B ² -B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , and R ⁹ is C _r C ₄ haloalkyl.

In another group of compounds of formula IE -B ¹ -B ² -B ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁹ is C ₃ -C ₄ cycloalkyl. In another group of compounds of formula IE -β'-Β^Β ³ - is -C=N-0-, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁹ is Ci-C ₄ alkyl, Ci-C ₄ haloalkyl or C3-C ₄ cycloalkyl and R ² is 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-, 2,6-dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)- 4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-.

In one group of compounds of formula IE -B ¹ -B ² -B ³ - is -C=N-CH ₂ -.

In another group of compounds of formula IE -B'-B^B ³ - is -C=N-CH ₂ - and Y ¹ is CH, Y ² is CH, Y ³ is CH.

In another group of compounds of formula IE -β'-Β^Β ³ - is -C=N-CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH and R ¹ is CF ₃ .

In another group of compounds of formula IE -β'-Β^Β ³ - is -C=N-CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ and R ⁹ is C _r C ₄ alkyl.

In another group of compounds of formula IE -β'-Β^Β ³ - is -C=N-CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , and R ⁹ is C _r C ₄ haloalkyl.

In another group of compounds of formula IE -β'-Β^Β ³ - is -C=N-CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁹ is C ₃ -C ₄ cycloalkyl.

In another group of compounds of formula IE -β'-Β^Β ³ - is -C=N-CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁹ is Ci-C ₄ alkyl, Ci-C ₄ haloalkyl or C ₃ -C ₄ cycloalkyl and R ² is 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-, 2,6-dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-

4- pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-.

In one group of compounds of formula IE -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -.

In another group of compounds of formula IE -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ - and Y ¹ is CH, Y ² is

CH, Y ³ is CH.

In another group of compounds of formula IE -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH and R ¹ is CF ₃ .

In another group of compounds of formula IE -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ and R ⁹ is C _r C ₄ alkyl.

In another group of compounds of formula IE -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , and R ⁹ is C _r C ₄ haloalkyl.

In another group of compounds of formula IE -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁹ is C ₃ -C ₄ cycloalkyl.

In another group of compounds of formula IE -B ¹ -B ² -B ³ - is -N-CH ₂ -CH ₂ -, Y ¹ is CH, Y ² is CH, Y ³ is CH, R ¹ is CF ₃ , R ⁹ is Ci-C ₄ alkyl, Ci-C ₄ haloalkyl or C ₃ -C ₄ cycloalkyl and R ² is 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-, 2,6-dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)- 4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-.

The following compounds of formula 1-1, 1-2 and 1-3 illustrate the compounds of formula I when -B'-B^B ³ - is -C=N-0-, -C=N-CH ₂ - , or -N-CH ₂ -CH ₂ - respectively.

(1-1 ) (I-2)

Tables 1 to 30 below illustrate compounds of the invention.

Table 1

Table 1 provides 304 compounds of formula la wherein R5 is hydrogen, B1-B2-B3 is C=N-0, and R2 and R8 are as defined in Table P.

Table 2

Table 2 provides 304 compounds of formula la wherein R5 is methyl, B1-B2-B3 is C=N-0, and R2 and R8 are as defined in Table P.

Table 3

Table 3 provides 304 compounds of formula la wherein R5 is trifluoromethyl, B1-B2-B3 is C=N-0, and R2 and R8 are as defined in Table P.

Table 4

Table 4 provides 304 compounds of formula la wherein R5 is chloro, B1-B2-B3 is C=N-0, and R2 and R8 are as defined in Table P.

Table 5

Table 5 provides 304 compounds of formula la wherein R5 is bromo, B1-B2-B3 is C=N-0, and R2 and R8 are as defined in Table P.

Table 6

Table 6 provides 304 compounds of formula la wherein R5 is hydrogen, B1-B2-B3 is C=N-CH2, and R2 and R8 are as defined in Table P.

Table 7

Table 7 provides 304 compounds of formula la wherein R5 is methyl, B1-B2-B3 is C=N-CH2, and R2 and R8 are as defined in Table P.

Table 8

Table 8 provides 304 compounds of formula la wherein R5 is trifluoromethyl, B1-B2-B3 is C=N-CH2, and R2 and R8 are as defined in Table P.

Table 9

Table 9 provides 304 compounds of formula la wherein R5 is chloro, B1-B2-B3 is C=N-CH2, and R2 and R8 are as defined in Table P. Table 10

Table 10 provides 304 compounds of formula la wherein R5 is bromo, B1-B2-B3 is C=N-CH2, and R2 and R8 are as defined in Table P.

Table 11

Table 11 provides 304 compounds of formula la wherein R5 is hydrogen, B1-B2-B3 is N-CH2-CH2, and R2 and R8 are as defined in Table P.

Table 12

Table 12 provides 304 compounds of formula la wherein R5 is methyl, B1-B2-B3 is N-CH2-CH2, and R2 and R8 are as defined in Table P.

Table 13

Table 13 provides 304 compounds of formula la wherein R5 is trifluoromethyl, B1-B2-B3 is N-CH2- CH2, and R2 and R8 are as defined in Table P.

Table 14

Table 14 provides 304 compounds of formula la wherein R5 is chloro, B1-B2-B3 is N-CH2-CH2, and R2 and R8 are as defined in Table P.

Table 15

Table 15 provides 304 compounds of formula la wherein R5 is bromo, B1-B2-B3 is N-CH2-CH2, and R2 and R8 are as defined in Table P.

Table P

R2 R8

1 3,5- dichloropheny 1 methyl

2 3 -chloro-4-fluorophenyl methyl

3 3-fluoro-4-chlorophenyl methyl

4 3 ,4-dichlorophenyl methyl

5 3 -chloro-4-bromophenyl methyl

6 3,5-dichloro-4-fluorophenyl methyl

7 3,4,5-trichlorophenyl methyl

8 3,5-dichloro-4-iodophenyl methyl

9 3,4,5-trifluorophenyl methyl

10 3-chloro-5-bromophenyl methyl

11 3-chloro-5-fluorophenyl methyl

12 3-chloro-5-(trifluoromethyl)phenyl methyl

13 3,4-dichloro-5-(trifluoromethyl)phenyl methyl

14 3 , 5 -bis(trifluoromethyl)phenyl methyl

15 4-chloro-3,5-bis(trifluoromethyl)phenyl methyl

16 3 -(trifluoromethyl)phenyl methyl

17 2,6-dichloro-4-pyridyl methyl

18 2,6-bis(trifluoromethyl)-4-pyridyl methyl

19 3-bromo-5-trifluoromethylphenyl methyl

20 3,5- dichloropheny 1 ethyl

21 3 -chloro-4-fluorophenyl ethyl

22 3-fluoro-4-chlorophenyl ethyl

23 3 ,4-dichlorophenyl ethyl

24 3 -chloro-4-bromophenyl ethyl

25 3,5-dichloro-4-fluorophenyl ethyl

26 3,4,5-trichlorophenyl ethyl 3,5-dichloro-4-iodophenyl ethyl

3,4,5-trifluorophenyl ethyl

3-chloro-5-bromophenyl ethyl

3-chloro-5-fluorophenyl ethyl

3-chloro-5-(trifluoromethyl)phenyl ethyl

3,4-dichloro-5-(trifluoromethyl)phenyl ethyl

3 , 5 -bis(trifluoromethyl)phenyl ethyl

4-chloro-3,5-bis(trifluoromethyl)phenyl ethyl

3 -(trifluoromethyl)phenyl ethyl

2,6-dichloro-4-pyridyl ethyl

2,6-bis(trifluoromethyl)-4-pyridyl ethyl

3-bromo-5-trifluoromethylphenyl ethyl

3,5- dichloropheny 1 propyl

3 -chloro-4-fluorophenyl propyl

3-fluoro-4-chlorophenyl propyl

3 ,4-dichlorophenyl propyl

3 -chloro-4-bromophenyl propyl

3,5-dichloro-4-fluorophenyl propyl

3,4,5-trichlorophenyl propyl

3,5-dichloro-4-iodophenyl propyl

3,4,5-trifluorophenyl propyl

3-chloro-5-bromophenyl propyl

3-chloro-5-fluorophenyl propyl

3-chloro-5-(trifluoromethyl)phenyl propyl

3,4-dichloro-5-(trifluoromethyl)phenyl propyl

3 , 5 -bis(trifluoromethyl)phenyl propyl

4-chloro-3,5-bis(trifluoromethyl)phenyl propyl

3 -(trifluoromethyl)phenyl propyl

2,6-dichloro-4-pyridyl propyl

2,6-bis(trifluoromethyl)-4-pyridyl propyl

3-bromo-5-trifluoromethylphenyl propyl

3,5- dichloropheny 1 isopropyl

3 -chloro-4-fluorophenyl isopropyl

3-fluoro-4-chlorophenyl isopropyl

3 ,4-dichlorophenyl isopropyl

3 -chloro-4-bromophenyl isopropyl

3,5-dichloro-4-fluorophenyl isopropyl

3,4,5-trichlorophenyl isopropyl

3,5-dichloro-4-iodophenyl isopropyl

3,4,5-trifluorophenyl isopropyl

3-chloro-5-bromophenyl isopropyl

3-chloro-5-fluorophenyl isopropyl

3-chloro-5-(trifluoromethyl)phenyl isopropyl

3,4-dichloro-5-(trifluoromethyl)phenyl isopropyl

3 , 5 -bis(trifluoromethyl)phenyl isopropyl

4-chloro-3,5-bis(trifluoromethyl)phenyl isopropyl 73 3 -(trifluoromethyl)phenyl isopropyl

74 2,6-dichloro-4-pyridyl isopropyl

75 2,6-bis(trifluoromethyl)-4-pyridyl isopropyl

76 3-bromo-5-trifluoromethylphenyl isopropyl

77 3,5- dichloropheny 1 CH3CH2CH(CH3)-

78 3 -chloro-4-fluorophenyl CH3CH2CH(CH3)-

79 3-fluoro-4-chlorophenyl CH3CH2CH(CH3)-

80 3 ,4-dichlorophenyl CH3CH2CH(CH3)-

81 3 -chloro-4-bromophenyl CH3CH2CH(CH3)-

82 3,5-dichloro-4-fluorophenyl CH3CH2CH(CH3)-

83 3,4,5-trichlorophenyl CH3CH2CH(CH3)-

84 3,5-dichloro-4-iodophenyl CH3CH2CH(CH3)-

85 3,4,5-trifluorophenyl CH3CH2CH(CH3)-

86 3-chloro-5-bromophenyl CH3CH2CH(CH3)-

87 3-chloro-5-fluorophenyl CH3CH2CH(CH3)-

88 3-chloro-5-(trifluoromethyl)phenyl CH3CH2CH(CH3)-

89 3,4-dichloro-5-(trifluoromethyl)phenyl CH3CH2CH(CH3)-

90 3 , 5 -bis(trifluoromethyl)phenyl CH3CH2CH(CH3)-

91 4-chloro-3,5-bis(trifluoromethyl)phenyl CH3CH2CH(CH3)-

92 3 -(trifluoromethyl)phenyl CH3CH2CH(CH3)-

93 2,6-dichloro-4-pyridyl CH3CH2CH(CH3)-

94 2,6-bis(trifluoromethyl)-4-pyridyl CH3CH2CH(CH3)-

95 3-bromo-5-trifluoromethylphenyl CH3CH2CH(CH3)-

96 3,5- dichloropheny 1 CH30CH2-

97 3 -chloro-4-fluorophenyl CH30CH2-

98 3-fluoro-4-chlorophenyl CH30CH2-

99 3 ,4-dichlorophenyl CH30CH2-

100 3 -chloro-4-bromophenyl CH30CH2-

101 3,5-dichloro-4-fluorophenyl CH30CH2-

102 3,4,5-trichlorophenyl CH30CH2-

103 3,5-dichloro-4-iodophenyl CH30CH2-

104 3,4,5-trifluorophenyl CH30CH2-

105 3-chloro-5-bromophenyl CH30CH2-

106 3-chloro-5-fluorophenyl CH30CH2-

107 3-chloro-5-(trifluoromethyl)phenyl CH30CH2-

108 3,4-dichloro-5-(trifluoromethyl)phenyl CH30CH2-

109 3 , 5 -bis(trifluoromethyl)phenyl CH30CH2-

110 4-chloro-3,5-bis(trifluoromethyl)phenyl CH30CH2-

111 3 -(trifluoromethyl)phenyl CH30CH2-

112 2,6-dichloro-4-pyridyl CH30CH2-

113 2,6-bis(trifluoromethyl)-4-pyridyl CH30CH2-

114 3-bromo-5-trifluoromethylphenyl CH30CH2-

115 3,5- dichloropheny 1 CH30CH2CH2-

116 3 -chloro-4-fluorophenyl CH30CH2CH2-

117 3-fluoro-4-chlorophenyl CH30CH2CH2-

118 3 ,4-dichlorophenyl CH30CH2CH2- 119 3 -chloro-4-bromophenyl CH30CH2CH2-

120 3,5-dichloro-4-fluorophenyl CH30CH2CH2-

121 3,4,5-trichlorophenyl CH30CH2CH2-

122 3,5-dichloro-4-iodophenyl CH30CH2CH2-

123 3,4,5-trifluorophenyl CH30CH2CH2-

124 3-chloro-5-bromophenyl CH30CH2CH2-

125 3-chloro-5-fluorophenyl CH30CH2CH2-

126 3-chloro-5-(trifluoromethyl)phenyl CH30CH2CH2-

127 3,4-dichloro-5-(trifluoromethyl)phenyl CH30CH2CH2-

128 3 , 5 -bis(trifluoromethyl)phenyl CH30CH2CH2-

129 4-chloro-3,5-bis(trifluoromethyl)phenyl CH30CH2CH2-

130 3 -(trifluoromethyl)phenyl CH30CH2CH2-

131 2,6-dichloro-4-pyridyl CH30CH2CH2-

132 2,6-bis(trifluoromethyl)-4-pyridyl CH30CH2CH2-

133 3-bromo-5-trifluoromethylphenyl CH30CH2CH2-

134 3,5- dichloropheny 1 CH30CH(CH3)CH2-

135 3 -chloro-4-fluorophenyl CH30CH(CH3)CH2-

136 3-fluoro-4-chlorophenyl CH30CH(CH3)CH2-

137 3 ,4-dichlorophenyl CH30CH(CH3)CH2-

138 3 -chloro-4-bromophenyl CH30CH(CH3)CH2-

139 3,5-dichloro-4-fluorophenyl CH30CH(CH3)CH2-

140 3,4,5-trichlorophenyl CH30CH(CH3)CH2-

141 3,5-dichloro-4-iodophenyl CH30CH(CH3)CH2-

142 3,4,5-trifluorophenyl CH30CH(CH3)CH2-

143 3-chloro-5-bromophenyl CH30CH(CH3)CH2-

144 3-chloro-5-fluorophenyl CH30CH(CH3)CH2-

145 3-chloro-5-(trifluoromethyl)phenyl CH30CH(CH3)CH2-

146 3,4-dichloro-5-(trifluoromethyl)phenyl CH30CH(CH3)CH2-

147 3 , 5 -bis(trifluoromethyl)phenyl CH30CH(CH3)CH2-

148 4-chloro-3,5-bis(trifluoromethyl)phenyl CH30CH(CH3)CH2-

149 3 -(trifluoromethyl)phenyl CH30CH(CH3)CH2-

150 2,6-dichloro-4-pyridyl CH30CH(CH3)CH2-

151 2,6-bis(trifluoromethyl)-4-pyridyl CH30CH(CH3)CH2-

152 3-bromo-5-trifluoromethylphenyl CH30CH(CH3)CH2-

153 3,5- dichloropheny 1 cyclopropyl

154 3 -chloro-4-fluorophenyl cyclopropyl

155 3-fluoro-4-chlorophenyl cyclopropyl

156 3 ,4-dichlorophenyl cyclopropyl

157 3 -chloro-4-bromophenyl cyclopropyl

158 3,5-dichloro-4-fluorophenyl cyclopropyl

159 3,4,5-trichlorophenyl cyclopropyl

160 3,5-dichloro-4-iodophenyl cyclopropyl

161 3,4,5-trifluorophenyl cyclopropyl

162 3-chloro-5-bromophenyl cyclopropyl

163 3-chloro-5-fluorophenyl cyclopropyl

164 3-chloro-5-(trifluoromethyl)phenyl cyclopropyl 165 3,4-dichloro-5-(trifluoromethyl)phenyl cyclopropyl

166 3 , 5 -bis(trifluoromethyl)phenyl cyclopropyl

167 4-chloro-3,5-bis(trifluoromethyl)phenyl cyclopropyl

168 3 -(trifluoromethyl)phenyl cyclopropyl

169 2,6-dichloro-4-pyridyl cyclopropyl

170 2,6-bis(trifluoromethyl)-4-pyridyl cyclopropyl

171 3-bromo-5-trifluoromethylphenyl cyclopropyl

172 3,5- dichloropheny 1 Cyclopropyl-CH2-

173 3 -chloro-4-fluorophenyl Cyclopropyl-CH2-

174 3-fluoro-4-chlorophenyl Cyclopropyl-CH2-

175 3 ,4-dichlorophenyl Cyclopropyl-CH2-

176 3 -chloro-4-bromophenyl Cyclopropyl-CH2-

177 3,5-dichloro-4-fluorophenyl Cyclopropyl-CH2-

178 3,4,5-trichlorophenyl Cyclopropyl-CH2-

179 3,5-dichloro-4-iodophenyl Cyclopropyl-CH2-

180 3,4,5-trifluorophenyl Cyclopropyl-CH2-

181 3-chloro-5-bromophenyl Cyclopropyl-CH2-

182 3-chloro-5-fluorophenyl Cyclopropyl-CH2-

183 3-chloro-5-(trifluoromethyl)phenyl Cyclopropyl-CH2-

184 3,4-dichloro-5-(trifluoromethyl)phenyl Cyclopropyl-CH2-

185 3 , 5 -bis(trifluoromethyl)phenyl Cyclopropyl-CH2-

186 4-chloro-3,5-bis(trifluoromethyl)phenyl Cyclopropyl-CH2-

187 3 -(trifluoromethyl)phenyl Cyclopropyl-CH2-

188 2,6-dichloro-4-pyridyl Cyclopropyl-CH2-

189 2,6-bis(trifluoromethyl)-4-pyridyl Cyclopropyl-CH2-

190 3-bromo-5-trifluoromethylphenyl Cyclopropyl-CH2-

191 3,5- dichloropheny 1 cyclobutyl

192 3 -chloro-4-fluorophenyl cyclobutyl

193 3-fluoro-4-chlorophenyl cyclobutyl

194 3 ,4-dichlorophenyl cyclobutyl

195 3 -chloro-4-bromophenyl cyclobutyl

196 3,5-dichloro-4-fluorophenyl cyclobutyl

197 3,4,5-trichlorophenyl cyclobutyl

198 3,5-dichloro-4-iodophenyl cyclobutyl

199 3,4,5-trifluorophenyl cyclobutyl

200 3-chloro-5-bromophenyl cyclobutyl

201 3-chloro-5-fluorophenyl cyclobutyl

202 3-chloro-5-(trifluoromethyl)phenyl cyclobutyl

203 3,4-dichloro-5-(trifluoromethyl)phenyl cyclobutyl

204 3 , 5 -bis(trifluoromethyl)phenyl cyclobutyl

205 4-chloro-3,5-bis(trifluoromethyl)phenyl cyclobutyl

206 3 -(trifluoromethyl)phenyl cyclobutyl

207 2,6-dichloro-4-pyridyl cyclobutyl

208 2,6-bis(trifluoromethyl)-4-pyridyl cyclobutyl

209 3-bromo-5-trifluoromethylphenyl cyclobutyl

210 3,5- dichloropheny 1 CH3-S-CH2- 211 3 -chloro-4-fluorophenyl CH3-S-CH2-

212 3-fluoro-4-chlorophenyl CH3-S-CH2-

213 3 ,4-dichlorophenyl CH3-S-CH2-

214 3 -chloro-4-bromophenyl CH3-S-CH2-

215 3,5-dichloro-4-fluorophenyl CH3-S-CH2-

216 3,4,5-trichlorophenyl CH3-S-CH2-

217 3,5-dichloro-4-iodophenyl CH3-S-CH2-

218 3,4,5-trifluorophenyl CH3-S-CH2-

219 3-chloro-5-bromophenyl CH3-S-CH2-

220 3-chloro-5-fluorophenyl CH3-S-CH2-

221 3-chloro-5-(trifluoromethyl)phenyl CH3-S-CH2-

222 3,4-dichloro-5-(trifluoromethyl)phenyl CH3-S-CH2-

223 3 , 5 -bis(trifluoromethyl)phenyl CH3-S-CH2-

224 4-chloro-3,5-bis(trifluoromethyl)phenyl CH3-S-CH2-

225 3 -(trifluoromethyl)phenyl CH3-S-CH2-

226 2,6-dichloro-4-pyridyl CH3-S-CH2-

227 2,6-bis(trifluoromethyl)-4-pyridyl CH3-S-CH2-

228 3-bromo-5-trifluoromethylphenyl CH3-S-CH2-

229 3,5- dichloropheny 1 CH3-S(0)-CH2-

230 3 -chloro-4-fluorophenyl CH3-S(0)-CH2-

231 3-fluoro-4-chlorophenyl CH3-S(0)-CH2-

232 3 ,4-dichlorophenyl CH3-S(0)-CH2-

233 3 -chloro-4-bromophenyl CH3-S(0)-CH2-

234 3,5-dichloro-4-fluorophenyl CH3-S(0)-CH2-

235 3,4,5-trichlorophenyl CH3-S(0)-CH2-

236 3,5-dichloro-4-iodophenyl CH3-S(0)-CH2-

237 3,4,5-trifluorophenyl CH3-S(0)-CH2-

238 3-chloro-5-bromophenyl CH3-S(0)-CH2-

239 3-chloro-5-fluorophenyl CH3-S(0)-CH2-

240 3-chloro-5-(trifluoromethyl)phenyl CH3-S(0)-CH2-

241 3,4-dichloro-5-(trifluoromethyl)phenyl CH3-S(0)-CH2-

242 3 , 5 -bis(trifluoromethyl)phenyl CH3-S(0)-CH2-

243 4-chloro-3,5-bis(trifluoromethyl)phenyl CH3-S(0)-CH2-

244 3 -(trifluoromethyl)phenyl CH3-S(0)-CH2-

245 2,6-dichloro-4-pyridyl CH3-S(0)-CH2-

246 2,6-bis(trifluoromethyl)-4-pyridyl CH3-S(0)-CH2-

247 3-bromo-5-trifluoromethylphenyl CH3-S(0)-CH2-

248 3,5- dichloropheny 1 CH3-S(02)-CH2-

249 3 -chloro-4-fluorophenyl CH3-S(02)-CH2-

250 3-fluoro-4-chlorophenyl CH3-S(02)-CH2-

251 3 ,4-dichlorophenyl CH3-S(02)-CH2-

252 3 -chloro-4-bromophenyl CH3-S(02)-CH2-

253 3,5-dichloro-4-fluorophenyl CH3-S(02)-CH2-

254 3,4,5-trichlorophenyl CH3-S(02)-CH2-

255 3,5-dichloro-4-iodophenyl CH3-S(02)-CH2-

256 3,4,5-trifluorophenyl CH3-S(02)-CH2- 257 3-chloro-5-bromophenyl CH3-S(02)-CH2-

258 3-chloro-5-fluorophenyl CH3-S(02)-CH2-

259 3-chloro-5-(trifluoromethyl)phenyl CH3-S(02)-CH2-

260 3,4-dichloro-5-(trifluoromethyl)phenyl CH3-S(02)-CH2-

261 3 , 5 -bis(trifluoromethyl)phenyl CH3-S(02)-CH2-

262 4-chloro-3,5-bis(trifluoromethyl)phenyl CH3-S(02)-CH2-

263 3 -(trifluoromethyl)phenyl CH3-S(02)-CH2-

264 2,6-dichloro-4-pyridyl CH3-S(02)-CH2-

265 2,6-bis(trifluoromethyl)-4-pyridyl CH3-S(02)-CH2-

266 3-bromo-5-trifluoromethylphenyl CH3-S(02)-CH2-

267 3 , 5 -dichlorophenyl tetrahydrofuran-2-yl

268 3 -chloro-4-fluorophenyl tetrahydrofuran-2-yl

269 3-fluoro-4-chlorophenyl tetrahydrofuran-2-yl

270 3 ,4-dichlorophenyl tetrahydrofuran-2-yl

271 3 -chloro-4-bromophenyl tetrahydrofuran-2-yl

272 3,5-dichloro-4-fluorophenyl tetrahydrofuran-2-yl

273 3,4,5-trichlorophenyl tetrahydrofuran-2-yl

274 3,5-dichloro-4-iodophenyl tetrahydrofuran-2-yl

275 3,4,5-trifluorophenyl tetrahydrofuran-2-yl

276 3-chloro-5-bromophenyl tetrahydrofuran-2-yl

277 3-chloro-5-fluorophenyl tetrahydrofuran-2-yl

278 3-chloro-5-(trifluoromethyl)phenyl tetrahydrofuran-2-yl

279 3,4-dichloro-5-(trifluoromethyl)phenyl tetrahydrofuran-2-yl

280 3 , 5 -bis(trifluoromethyl)phenyl tetrahydrofuran-2-yl

281 4-chloro-3,5-bis(trifluoromethyl)phenyl tetrahydrofuran-2-yl

282 3 -(trifluoromethyl)phenyl tetrahydrofuran-2-yl

283 2,6-dichloro-4-pyridyl tetrahydrofuran-2-yl

284 2,6-bis(trifluoromethyl)-4-pyridyl tetrahydrofuran-2-yl

285 3-bromo-5-trifluoromethylphenyl tetrahydrofuran-2-yl

286 3,5- dichlorophenyl tetrahydrofuran-3 -yl

287 3 -chloro-4-fluorophenyl tetrahydrofuran-3 -yl

288 3-fluoro-4-chlorophenyl tetrahydrofuran-3 -yl

289 3 ,4-dichlorophenyl tetrahydrofuran-3 -yl

290 3 -chloro-4-bromophenyl tetrahydrofuran-3 -yl

291 3,5-dichloro-4-fluorophenyl tetrahydrofuran-3 -yl

292 3,4,5-trichlorophenyl tetrahydrofuran-3 -yl

293 3,5-dichloro-4-iodophenyl tetrahydrofuran-3 -yl

294 3,4,5-trifluorophenyl tetrahydrofuran-3 -yl

295 3-chloro-5-bromophenyl tetrahydrofuran-3 -yl

296 3-chloro-5-fluorophenyl tetrahydrofuran-3 -yl

297 3-chloro-5-(trifluoromethyl)phenyl tetrahydrofuran-3 -yl

298 3,4-dichloro-5-(trifluoromethyl)phenyl tetrahydrofuran-3 -yl

299 3 , 5 -bis(trifluoromethyl)phenyl tetrahydrofuran-3 -yl

300 4-chloro-3,5-bis(trifluoromethyl)phenyl tetrahydrofuran-3 -yl

301 3 -(trifluoromethyl)phenyl tetrahydrofuran-3 -yl

302 2,6-dichloro-4-pyridyl tetrahydrofuran-3 -yl 303 2,6-bis(trifluoromethyl)-4-pyridyl tetrahydrofuran-3 -yl

304 3-bromo-5-trifluoromethylphenyl tetrahydrofuran-3 -yl

Table 16

Table 16 provides 304 compounds of formula lb wherein B1-B2-B3 is C=N-0, and R2 and R8 are as defined in Table P.

Table 17

Table 17 provides 304 compounds of formula lb wherein B1-B2-B3 is C=N-CH2, and R2 and R8 are as defined in Table P.

Table 18

Table 18 provides 304 compounds of formula lb wherein B1-B2-B3 is N-CH2-CH2, and R2 and R8 are as defined in Table P.

Table 19

Table 19 provides 19 compounds of formula Ic wherein B1-B2-B3 is C=N-0, and R2 is as defined in Table Q.

Table 20

Table 20 provides 19 compounds of formula Ic wherein B1-B2-B3 is C=N-CH2, and R2 is as defined in Table Q.

Table 21

Table 21 provides 19 compounds of formula Ic wherein B1-B2-B3 is N-CH2-CH2, and R2 is as defined in Table Q.

Table 22 Table 22 provides 19 compounds of formula Id wherein k is CN, B1-B2-B3 is C=N-0 and R2 is as defined in Table Q.

Table 23

Table 23 provides 19 compounds of formula Id wherein k is CF3, B1-B2-B3 is C=N-0 and R2 is as defined in Table Q.

Table 24

Table 24 provides 19 compounds of formula Id wherein k is CN, B1-B2-B3 is C=N-CH2 and R2 is as defined in Table Q.

Table 25

Table 25 provides 19 compounds of formula Id wherein k is CF3, B1-B2-B3 is C=N-CH2 and R2 is as defined in Table Q.

Table 26

Table 26 provides 19 compounds of formula Id wherein k is CN, B1-B2-B3 is N-CH2-CH2 and R2 is as defined in Table Q.

Table 27

Table 27 provides 19 compounds of formula Id wherein k is CF3, B1-B2-B3 is N-CH2-CH2 and R2 is as defined in Table Q.

Table 0

R2

1 3,5- dichloropheny 1

2 3 -chloro-4-fluorophenyl

3 3-fluoro-4-chlorophenyl

4 3 ,4-dichlorophenyl

5 3 -chloro-4-bromophenyl

6 3,5-dichloro-4-fluorophenyl

7 3,4,5-trichlorophenyl

8 3,5-dichloro-4-iodophenyl

9 3,4,5-trifluorophenyl

10 3-chloro-5-bromophenyl

11 3-chloro-5-fluorophenyl

12 3-chloro-5-(trifluoromethyl)phenyl

13 3,4-dichloro-5-(trifluoromethyl)phenyl

14 3 , 5 -bis(trifluoromethyl)phenyl

15 4-chloro-3,5-bis(trifluoromethyl)phenyl

16 3 -(trifluoromethyl)phenyl

17 2,6-dichloro-4-pyridyl

18 2,6-bis(trifluoromethyl)-4-pyridyl

19 3-bromo-5-trifluoromethylphenyl

Table 28

Table 28 provides 114 compounds of formula le wherein B1-B2-B3 is C=N-0, and R2 and R9 are as defined in Table S.

Table 29

Table 29 provides 114 compounds of formula le wherein B1-B2-B3 is C=N-CH2, and R2 and R9 are as defined in Table S.

Table 30

Table 30 provides 114 compounds of formula le wherein B1-B2-B3 is N-CH2-CH2, and R2 and R9 are as defined in Table S.

Table S

R2 R9

1 3,5- dichloropheny 1 methyl

2 3 -chloro-4-fluorophenyl methyl

3 3-fluoro-4-chlorophenyl methyl

4 3 ,4-dichlorophenyl methyl

5 3 -chloro-4-bromophenyl methyl

6 3,5-dichloro-4-fluorophenyl methyl

7 3,4,5-trichlorophenyl methyl

8 3,5-dichloro-4-iodophenyl methyl

9 3,4,5-trifluorophenyl methyl

10 3-chloro-5-bromophenyl methyl

11 3-chloro-5-fluorophenyl methyl

12 3-chloro-5-(trifluoromethyl)phenyl methyl

13 3,4-dichloro-5-(trifluoromethyl)phenyl methyl

14 3 , 5 -bis(trifluoromethyl)phenyl methyl

15 4-chloro-3,5-bis(trifluoromethyl)phenyl methyl

16 3 -(trifluoromethyl)phenyl methyl

17 2,6-dichloro-4-pyridyl methyl

18 2,6-bis(trifluoromethyl)-4-pyridyl methyl

19 3-bromo-5-trifluoromethylphenyl methyl

20 3,5- dichloropheny 1 ethyl

21 3 -chloro-4-fluorophenyl ethyl

22 3-fluoro-4-chlorophenyl ethyl

23 3 ,4-dichlorophenyl ethyl

24 3 -chloro-4-bromophenyl ethyl

25 3,5-dichloro-4-fluorophenyl ethyl 3,4,5-trichlorophenyl ethyl

3,5-dichloro-4-iodophenyl ethyl

3,4,5-trifluorophenyl ethyl

3-chloro-5-bromophenyl ethyl

3-chloro-5-fluorophenyl ethyl

3-chloro-5-(trifluoromethyl)phenyl ethyl

3,4-dichloro-5-(trifluoromethyl)phenyl ethyl

3 , 5 -bis(trifluoromethyl)phenyl ethyl

4-chloro-3,5-bis(trifluoromethyl)phenyl ethyl

3 -(trifluoromethyl)phenyl ethyl

2,6-dichloro-4-pyridyl ethyl

2,6-bis(trifluoromethyl)-4-pyridyl ethyl

3-bromo-5-trifluoromethylphenyl ethyl

3,5- dichloropheny 1 cyclopropyl

3 -chloro-4-fluorophenyl cyclopropyl

3-fluoro-4-chlorophenyl cyclopropyl

3 ,4-dichlorophenyl cyclopropyl

3 -chloro-4-bromophenyl cyclopropyl

3,5-dichloro-4-fluorophenyl cyclopropyl

3,4,5-trichlorophenyl cyclopropyl

3,5-dichloro-4-iodophenyl cyclopropyl

3,4,5-trifluorophenyl cyclopropyl

3-chloro-5-bromophenyl cyclopropyl

3-chloro-5-fluorophenyl cyclopropyl

3-chloro-5-(trifluoromethyl)phenyl cyclopropyl

3,4-dichloro-5-(trifluoromethyl)phenyl cyclopropyl

3 , 5 -bis(trifluoromethyl)phenyl cyclopropyl

4-chloro-3,5-bis(trifluoromethyl)phenyl cyclopropyl

3 -(trifluoromethyl)phenyl cyclopropyl

2,6-dichloro-4-pyridyl cyclopropyl

2,6-bis(trifluoromethyl)-4-pyridyl cyclopropyl

3-bromo-5-trifluoromethylphenyl cyclopropyl

3,5- dichloropheny 1 CF3CH2-

3 -chloro-4-fluorophenyl CF3CH2-

3-fluoro-4-chlorophenyl CF3CH2-

3 ,4-dichlorophenyl CF3CH2-

3 -chloro-4-bromophenyl CF3CH2-

3,5-dichloro-4-fluorophenyl CF3CH2-

3,4,5-trichlorophenyl CF3CH2-

3,5-dichloro-4-iodophenyl CF3CH2-

3,4,5-trifluorophenyl CF3CH2-

3-chloro-5-bromophenyl CF3CH2-

3-chloro-5-fluorophenyl CF3CH2-

3-chloro-5-(trifluoromethyl)phenyl CF3CH2-

3,4-dichloro-5-(trifluoromethyl)phenyl CF3CH2-

3 , 5 -bis(trifluoromethyl)phenyl CF3CH2- 72 4-chloro-3,5-bis(trifluoromethyl)phenyl CF3CH2-

73 3 -(trifluoromethyl)phenyl CF3CH2-

74 2,6-dichloro-4-pyridyl CF3CH2-

75 2,6-bis(trifluoromethyl)-4-pyridyl CF3CH2-

76 3-bromo-5-trifluoromethylphenyl CF3CH2-

77 3,5- dichloropheny 1 cyclopropyl-CH2-

78 3 -chloro-4-fluorophenyl cyclopropyl-CH2-

79 3-fluoro-4-chlorophenyl cyclopropyl-CH2-

80 3 ,4-dichlorophenyl cyclopropyl-CH2-

81 3 -chloro-4-bromophenyl cyclopropyl-CH2-

82 3,5-dichloro-4-fluorophenyl cyclopropyl-CH2-

83 3,4,5-trichlorophenyl cyclopropyl-CH2-

84 3,5-dichloro-4-iodophenyl cyclopropyl-CH2-

85 3,4,5-trifluorophenyl cyclopropyl-CH2-

86 3-chloro-5-bromophenyl cyclopropyl-CH2-

87 3-chloro-5-fluorophenyl cyclopropyl-CH2-

88 3-chloro-5-(trifluoromethyl)phenyl cyclopropyl-CH2-

89 3,4-dichloro-5-(trifluoromethyl)phenyl cyclopropyl-CH2-

90 3 , 5 -bis(trifluoromethyl)phenyl cyclopropyl-CH2-

91 4-chloro-3,5-bis(trifluoromethyl)phenyl cyclopropyl-CH2-

92 3 -(trifluoromethyl)phenyl cyclopropyl-CH2-

93 2,6-dichloro-4-pyridyl cyclopropyl-CH2-

94 2,6-bis(trifluoromethyl)-4-pyridyl cyclopropyl-CH2-

95 3-bromo-5-trifluoromethylphenyl cyclopropyl-CH2-

96 3,5- dichloropheny 1 isopropyl

97 3 -chloro-4-fluorophenyl isopropyl

98 3-fluoro-4-chlorophenyl isopropyl

99 3 ,4-dichlorophenyl isopropyl

100 3 -chloro-4-bromophenyl isopropyl

101 3,5-dichloro-4-fluorophenyl isopropyl

102 3,4,5-trichlorophenyl isopropyl

103 3,5-dichloro-4-iodophenyl isopropyl

104 3,4,5-trifluorophenyl isopropyl

105 3-chloro-5-bromophenyl isopropyl

106 3-chloro-5-fluorophenyl isopropyl

107 3-chloro-5-(trifluoromethyl)phenyl isopropyl

108 3,4-dichloro-5-(trifluoromethyl)phenyl isopropyl

109 3 , 5 -bis(trifluoromethyl)phenyl isopropyl

110 4-chloro-3,5-bis(trifluoromethyl)phenyl isopropyl

111 3 -(trifluoromethyl)phenyl isopropyl

112 2,6-dichloro-4-pyridyl isopropyl

113 2,6-bis(trifluoromethyl)-4-pyridyl isopropyl

114 3-bromo-5-trifluoromethylphenyl isopropyl Compounds of formula I include at least one chiral centre and may exist as compounds of formula I* or compounds of formula I**. Compounds I* and I** are enantiomers if there is no other chiral center or epimers otherwise.

(I*) (I**)

Generally compounds of formula I** are more biologically active than 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 (or epimers) 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 mixtures of formula I*, the molar proportion of the compound of formula I* compared to the total amount of both enantiomers (or epimers) 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 30 represents a disclosure of a compound according to the compound of formula I* and a compound according to the compound of formula I**.

Likewise, group A2 may be group A2* or A2**.

(A2*) (A2**)

The invention includes mixtures of compounds of formula I with A2 as A2* and A2** 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 with A2 as A2*, the molar proportion of formula I with A2 as A2* compared to the total amount of both enantiomers (or epimers) 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 I with A2 as A2**, the molar proportion of the compound of formula I with A2 as A2**, compared to the total amount of both enantiomers (or epimers) 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 with A2 as A2** are preferred. Each compound disclosed in Tables 16 to 18 represents a disclosure of I with A2 as A2* and a compound I with A2 as A2**. Each compound disclosed in Tables 16 to 18 represents a disclosure of a compound according to formula I* with A2 as A2*. Each compound disclosed in Tables 16 to 18 represents a disclosure of a compound according to formula I** with A2 as A2*. Each compound 5 disclosed in Tables 16 to 18 represents a disclosure of a compound according to formula I* with A2 as A2**. Each compound disclosed in Tables 16 to 18 represents a disclosure of a compound according to formula I** with A2 as A2**. Enantiomerically (or epimerically) enriched mixtures of formula I** with A2 as A2** are preferred.

Likewise, group A5 may be A5* or A5

10 (A5*) (A5**)

The invention includes mixtures of compounds of formula I with A5 as A5* and A5** 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 with A5 as A5*, the molar proportion of formula I with A5 as A5* compared to the total amount of both enantiomers (or epimers) is for example

15 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 I with A5 as A5**, the molar proportion of the compound of formula I with A5 as A5**, compared to the total amount of both enantiomers (or epimers) 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%. Compounds of formula A5* are preferred.

20 Each compound disclosed in Tables 28 to 30 represents a disclosure of I with A5 as A5* and a compound I with A5 as A5**. Each compound disclosed in Tables 28 to 30 represents a disclosure of a compound according to formula I* with A5 as A5*. Each compound disclosed in Tables 28 to 30 represents a disclosure of a compound according to formula I** with A5 as A5*. Each compound disclosed in Tables 28 to 30 represents a disclosure of a compound according to formula I* with A5 as

25 A5**. Each compound disclosed in Tables 28 to 30 represents a disclosure of a compound according to formula I** with A5 as A5**.

The compounds of formula I may be prepared as described in WO08128711, WO10043315, The compounds of formula I may be prepared as described in WO 2008/128711, WO 2010/043315, WO 2011/051455, WO 2007/105814, WO 2008/122375, WO 2009/035004, WO 2009/045999, WO

30 2009/072621, WO 2009/097992, WO 2010/133336, WO 2010/043315, WO 2011/051455, WO 2011/080211, ^2010235590^2011037817^2011178724 _a _CN102210317 _a _CNl 02246777, WO 2009/07261, WO 2009/097992, WO 2009/051956, each of which is incorporated herein by reference.

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.

In one embodiment the invention provides a compound selected from Tables 1 to 15 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 16 to 18 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 19 to 21 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 22 to 27 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 28 to 30 for use in controlling and/or preventing soil pests.

In one embodiment the invention provides a compound selected from Tables 1 to 15 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 16 to 18 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 19 to 21 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 22 to 27 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 28 to 30 for use in controlling and/or preventing corn rootworm.

In one embodiment the invention provides a compound selected from Tables 1 to 15 for use in controlling and/or preventing wireworms.

In one embodiment the invention provides a compound selected from Tables 16 to 18 for use in controlling and/or preventing wireworms.

In one embodiment the invention provides a compound selected from Tables 19 to 21 for use in controlling and/or preventing wireworms.

In one embodiment the invention provides a compound selected from Tables 22 to 27 for use in controlling and/or preventing wireworms.

In one embodiment the invention provides a compound selected from Tables 28 to 30 for use in controlling and/or preventing wireworms. In one embodiment the invention provides a compound selected from Tables 1 to 15 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 16 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 21 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 22 to 27 for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides a compound selected from Tables 28 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 1 to 15 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 16 to 18 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 19 to 21 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 22 to 27 for use in controlling and/or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 28 to 30 for use in controlling and/ or preventing Phyllophaga sp..

In one embodiment the invention provides a compound selected from Tables 1 to 15 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 16 to 18 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 19 to 21 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 22 to 27 for use in controlling and/or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 28 to 30 for use in controlling and/ or preventing Diloboderus sp..

In one embodiment the invention provides a compound selected from Tables 1 to 15 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 16 to 18 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 19 to 21 for use in controlling and/or preventing Popillia japonica. In one embodiment the invention provides a compound selected from Tables 22 to 27 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 28 to 30 for use in controlling and/or preventing Popillia japonica.

In one embodiment the invention provides a compound selected from Tables 1 to 15 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 16 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 21 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 22 to 27 for use in controlling and/or preventing termites, e.g. for sugarcane.

In one embodiment the invention provides a compound selected from Tables 28 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 1 to 15 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 16 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 21 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 22 to 27 for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris sp..

In one embodiment the invention provides a compound selected from Tables 28 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 1 to 15 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 16 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 21 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 22 to 27 for use in controlling and/or preventing cutworms, e.g. agrotis sp..

In one embodiment the invention provides a compound selected from Tables 28 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 1 to 15 for use in controlling and/or preventing millipedes, e.g. Julus sp.. In one embodiment the invention provides a compound selected from Tables 16 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 21 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 22 to 27 for use in controlling and/or preventing millipedes, e.g. Julus sp..

In one embodiment the invention provides a compound selected from Tables 28 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 1 to 15 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 16 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 21 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 22 to 27 for use in controlling and/or preventing broca gigante, e.g. Telchin licus.

In one embodiment the invention provides a compound selected from Tables 28 to 30 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 30 above may be used to combat soil grubs e.g. Migdolus sp.; Phyllophaga sp.; Diloboderus sp.; Cydocephala 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 califomicus.

In another embodiment the compounds of formula (I), in particular those in in Tables 1 to 30 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.; Cydocephala 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 30 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.

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. The compound of formula I may be a compound of formula IA (e.g. compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16-18), IC (e.g.

compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g. compounds from Tables 28-30).

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. The compound of formula I may be a compound of formula IA (e.g. compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16-18), IC (e.g. compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g. compounds from Tables 28-30).

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. The compound of formula I may be a compound of formula IA (e.g. compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16-18), IC (e.g.

compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g. compounds from Tables 28-30).

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. The compound of formula I may be a compound of formula IA (e.g. compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16-18), IC (e.g. compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g. compounds from Tables 28-30).

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. The compound of formula I may be a compound of formula IA (e.g. compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16-18), IC (e.g. compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g. compounds from Tables 28-30). 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. The compound of formula I may be a compound of formula IA (e.g.

compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16-18), IC (e.g. compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g. compounds from Tables 28-30).

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. The compound of formula I may be a compound of formula IA (e.g. compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16-18), IC (e.g. compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g. compounds from Tables 28-30).

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. The compound of formula I may be a compound of formula IA (e.g. compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16-18), IC (e.g. compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g. compounds from Tables 28-30).

In a further aspect the invention provides use of a compound of formula I for controlling and/or preventing 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. The compound of formula I may be a compound of formula IA (e.g. compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16-18), IC (e.g. compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g.

compounds from Tables 28-30).

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. The compound of formula I may be a compound of formula IA (e.g. compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16- 18), IC (e.g. compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g. compounds from Tables 28-30).

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. The compound of formula I may be a compound of formula IA (e.g. compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16-18), IC (e.g. compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g. compounds from Tables 28-30).

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. The compound of formula I may be a compound of formula IA (e.g. compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16-18), IC (e.g. compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g. compounds from Tables 28-30).

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. The compound of formula I may be a compound of formula IA (e.g. compounds from Tables 1 to 15), IB (e.g. compounds from Tables 16-18), IC (e.g.

compounds from Tables 19 to 21), ID (e.g. compounds from Tables 22 to 27) or IE (e.g. compounds from Tables 28-30).

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 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 directly to soil comprises applying the compound of formula I to the soil other than via seed treatment.

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 CrylAb and mCry3A); YieldGard® (P5) (corn hybrids producing the CrylAb 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® (PI 3) (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. Btl76 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 (P18). 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 Cry IF 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 x 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).

Examples of cotton transgenic events include MON 531 / 757 / 1076 (Bollgard I ® - Monsanto), MON1445 (Roundup ready cotton ®- Monsanto), MON531 x MON1445 (Bollgard I + RR ®- Monsanto), MON15985 (Genuity Bollgard II cotton ®- Monsanto), MON88913 (Genuity RR FLEX cotton ®- Monsanto), MON15985 x MON1445 (Genuity Bollgard II + RR FELX cotton ®- Monsanto), MON15983 x MON88913 (Genuity Bollgard II + RR FLEX cotton ® - Monsanto), MON15985

(FibreMax Bollgard II Cotton ® - Monsanto), LL25 (FibreMax LL cotton ® - BCS Stoneville), GHB614 (FibreMax GlyTol cotton ®- BCS Stoneville), LL25 x MON15985 (FibreMax LL Bollgard II cotton ® - BCS Stoneville / Monsanto), GHB614 x LL25 (FibreMax LL GlyTol cotton ® - BCS Stoneville), GHB614 x LL25 x MON15985 (FibreMax RR GlyTol Bollgard II cotton ® - BCS Stoneville),

MON88913 x MON15985 (FibreMax LL GlyTol Bollgard II cotton ® - Monsanto), MON88913 (FibreMax RR Flex cotton ® - Monsanto), GHB119 + T304-40 (Twinlink ® - BCS Stoneville), GHB119 + T304-40 x LL25 x GHB614 (Twinlink LL GT ® - BCS Stoneville), 3006-210-23 x 281-24-236 (PhytoGen Widestrike Insect Protection ® - Dow), 3006-210-23 x 281-24-236 x MON88913 (PhytoGen Widestrike Insect Protection + RR FLEX - ® Dow / Monsanto), 3006-210-23 x 281-24-236 x MON1445 ((PhytoGen Widestrike Insect Protection + RR ® - Dow / Monsanto), MON1445 (PhytoGen Roundup Ready ® - Monsanto), MON88913 (PhytoGen Roundup Ready FLEX ® - Monsanto), COT102 x COT67B (Vipcot ® - Syngenta), COT102 x COT67B x MON88913 (Vipcot RR FLEX ® - Syngenta / Monsanto), 281-24-236 (Dow), 3006-210-23 (Dow), COT102 (Syngenta), COT67B (Syngenta), T304-40 (BCS Stoneville).

Examples of Soy transgenic events include MON87701 x MON89788 (Genuity Roundup ready 2

Yield soybeans® - Monsanto), MON89788 (Roundup Ready2Yield®, RR2Y® - Monsanto), MON87708 (Monsanto), 40-3-2 (Roundup Ready®, RRl® - Monsanto), MON87701 (Monsanto), DAS-68416 (Enlist Weed Control System® - Dow), DP356043 (Optimum GAT® - Pioneer), A5547-127 (LibertyLink soybean® - Bayercropscience), A2704-12 (Bayercropscience), GU262 (Bayercropscience), W62 W98 (Bayercropscience), CRV127 (Cultivance® - BASF / EMBRAPA), SYHT0H2 (WO2012/082548).

Examples of Maize transgenic events include T25 (LibertyLink®, LL® - Bayerscropscience), DHT-1 (Dow), TCI 507 (Herculex I® - Dow), DAS59122-7 (Herculex RW® - Dow), TCI 507 + DAS59122-7 - Herculex Xtra® - Dow), TCI 507 x DAS-59122-7 x NK603 (Herculex Xtra + RR® - Dow), TC1507 x DAS-59122- x MON88017 x MON89034 (Genuity Smartstax corn®, Genuity

Smartstax RIB complete® - Monsanto / Dow), MON89034 x NK603 (Genuity VT double PRO® -

Monsanto), MON89034 + MON88017 (Genuity VT Triple PRO® - Monsanto), NK603 (Roundup Ready 2®, RR2® - Monsanto), MON810 (YieldGard BT®, Yieldgard cornborer® - Monsanto), MON810 x NK603 (YieldGard cornborer RR Corn 2® - Monasnto), MON810 x MON863 (YieldGard Plus® - Monsanto), MON863 x MON810 x NK603 (YieldGard Plus + RR Corn2® / YieldGard RR Maize® - Monsanto), MON863 x NK603 (YieldGard Rotworm + RR Corn 2® - Monsanto), MON863 (YieldBard RW® - Monsanto), MON89034 (YieldGard RW® - Monsanto), MON88017 (YieldGard VT RW® - Monsanto), MON810 + MON88017 (YieldGard VT Triple® - Monsanto), MON88017 + MON89034 (YieldGard VT Triple Pro® - Monsanto), Btl 1 + MIR604 + GA21 (Agrisure 3000® - Syngenta), Btl 1 + TC1507 + MIR604 + 5307 + GA21 (Syngenta), Btl 1 + TC1507 + MIR604 + DAS59122 + GA21 (Agrisure 3122® - Syngenta), BT11 (Agrisure CB® - Syngenta), GA21 - (Agrisure GT® - Syngenta), MIR604 (Agrisure RW® - Syngenta), Btl 1 + MIR162 (Agrisure TL VIP® - Syngenta), BT11 + MIR162 + GA21 (Agrisure Viptra 3110® - Syngenta), BT11 + MIR162 + MIR604 (Agrisure TM 3100® - Syngenta), Event3272 + BT11 + MIR604 + GA21 (Syngenta), BT11 + MIR1692 + MIR604 + GA21 (Agrisure Viptera 3111® - Syngenta), BT11 + MIR 162 + TC1507 + GA21 (Agrisure Viptera 3220® - Syngenta), BT11 + MIR162 + TC1507 + MIR604 + 5307 + GA21 (Agrisure Viptera 3222® - Syngenta), MIR162 (Syngenta), BT11 + GA21 + MIR162 + MIR604 + 5307 (Syngenta), 5307 (Syngenta). 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)-(lR,3S)-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- 1 -sulfonamide, a

-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]-y-butyrolactone , 4-chloro-2-cyano-N,N-dimethyl-5-/ tolylimidazole- 1 -sulfonamide (IKF-916, cyamidazosulfamid), 3 -5-dichloro-N-(3 -chloro- 1 -ethyl- 1 -methyl- 2- oxopropyl)-4-methylbenzamide (RH-7281 , zoxamide), N-allyl-4,5,-dimethyl-2-trimethylsilylthiophene-

3- carboxamide (MON65500), N-(l -cyano-l ,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,

O _j O-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, LY21 1795, 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-l -methyl- indan-4-yl)-amide, and l -methyl-3-difluoromethyl-4H-pyrazole-

4- carboxylic acid [2-(2,4-dichloro-phenyl)-2-methoxy- 1 -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 30 + thiamethoxam + abamectin + mefenoxam + fludioxonil + azoxystrobin + thiabendazole; a compound selected from Tables 1 to 30 + abamectin + mefenoxam + fludioxonil + azoxystrobin + thiabendazole, a compound selected from Tables 1 to 30+ thiamethoxam + mefenoxam + fludioxonil + azoxystrobin + thiabendazole, a compound selected from Tables 1 to 30+ thiamethoxam + abamectin + mefenoxam + fludioxonil + azoxystrobin + thiabendazole, a compound selected from Tables 1 to 30 + thiamethoxam + abamectin + fludioxonil + azoxystrobin + thiabendazole, a compound selected from Tables 1 to 30 + thiamethoxam + abamectin + mefenoxam + azoxystrobin + thiabendazole, a compound selected from Tables 1 to 30 + thiamethoxam + abamectin + mefenoxam + fludioxonil + thiabendazole, a compound selected from Tables 1 to 30 + 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 lOOOg / 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.

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

active ingredients 40 %

propylene glycol 5 % copolymer butanol PO/EO 2 %

Tristyrenephenole with 10-20 moles EO 2 %

l ,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 %

monoazo-pigment calcium salt 5 %

Silicone oil (in the form of a 75 % emulsion in water) 0.2 %

Water 45.3 %

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 Examples illustrate but do not limit the invention.

Example 1 : Preparation of N-[(l S)-l -r4-[3-r3,5-bis(trifluoromethyl)phenyll-3- (trifluorometh l)pyrrolidin-l -yllphenyllethyllcyclopropanecarboxamide

To a solution of 3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrol idine (0.15 g, 0.4271 mmol, prepared as described in WO 2008/12871 1) and N-[(l S)-l -(4- bromophenyl)ethyl]cyclopropanecarboxamide (0.134 g, 0.4997 mmol, prepared as described in WO 2012/001 107) in Toluene (6.03 mL), stirred under argon were added tris(dibenzylideneacetone)dipalladium(0) (9 mg), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (18 mg) and sodium tert-butoxide (96 mg). The mixture was heated in a microwave at 130°C for 15 min. The reaction was then diluted with ethylacetate and water then brine and then the mixture was extracted with ethyl acetate. The organic layers were combined and dried over magnesium sulphate, filtered then concentrated under reduced pressure to give a yellow oil which was purified by chromatography on a column (cyclohexane/EtOAc as solvent) to afford the desired product as a white foam (172 mg).

lU NMR (CDC13, 400MHz): d = 7.92 (s, 1 H), 7.86 (s, 2 H), 7.27 (m, 2 H), 6.63 (d, J=8.4 Hz, 2 H), 5.74 (d, J=7.7 Hz, 1 H), 5.09 (t, J=7.3 Hz, 1 H), 4.16 (d, J=10.3 Hz, 1 H), 3.85 (d, J=10.3 Hz, 1 H), 3.60 (d, J=8.1 Hz, 1 H), 3.51 (d, J=2.9 Hz, 1 H), 2.91 - 3.03 (m, 1 H), 2.61 (d, J=13.6 Hz, 1 H), 1.50 (d, J=7.0 Hz, 3 H), 1.17 - 1.34 (m, 1 H), 0.90 - 1.04 (m, 2 H), 0.63 - 0.80 ppm (m, 2 H)

Example 2: Preparation of N-[(l S)-l-r4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidi n-l - llphenyllethyllcyclopropanecarboxamide

Tris(dibenzylideneacetone)dipalladium(0) (32 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (61 mg) and sodium tert-butoxide (190 mg) were added to a solution of 3-(3,5-dichlorophenyl)-3- (trifluoromethyl)pyrrolidine (520 mg, prepared as described in WO 2008/128711) and N-[(lS)-l-(4- bromophenyl)ethyl]cyclopropanecarboxamide (prepared as described in WO 2012/001107, 520 mg) in toluene (15 mL) under argon atmosphere. The mixture was heated in a microwave at 130°C for 30 min. The reaction was then diluted with ethylacetate and water then brine and then the mixture was extracted with ethyl acetate. The organic layers were combined and dried over sodium sulphate, filtered then concentrated under reduced pressure to give a yellow oil which was purified by chromatography on column (Heptane/EtOAc as solvent (10/0 to 0/10) to afford the desired product as a white foam (650 mg). ^l U NMR (CDC13, 400MHz): d = 7.40 (s, 1 H), 7.31 (s, 2 H), 7.26 (m, 2 H), 6.62 (d, 2 H), 5.73 (d, 1 H), 5.09 (t, 1 H), 4.06 (d, 1 H), 3.85 (d, 1 H), 3.57 (m, 1 H), 3.50 (m, 1 H), 2.84 (m, 1 H), 2.56 (m, 1 H), 1.50 (d, 3 H), 1.2 (m, 1 H), 0.99 (m, 2 H), 0.72 ppm (m, 2 H)

Example 3: Preparation of N-[(l S)-l-r4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxa zol-3- yllphenyl] ethyl] acetamide

Step 1 :

To a suspension of N-[(lS)-l-(4-acetylphenyl)ethyl]acetamide (3 g) and l-(3,5-dichlorophenyl)-2,2,2- trifluoro-ethanone (3.6 g) in 1 ,2-dichloroethane (40 niL) was added triethylamine (0.2 mL) and potassium carbonate (1 g). The solution was stirred at 80°C. After 40 minutes more potassium carbonate (1 g) was added. The solution was heated at 80°C for another 20 minutes then more potassium carbonate (1 g) was added and the suspension was refluxed for 16 hours. The mixture was then cooled to room temperature, and water was added. The mixture was extracted with dichloromethane then washed with brine. The organic layers were combined and dried over magnesium sulphate, filtered then concentrated under reduced pressure to give a yellow oil which was purified by chromatography on column (Heptane/EtOAc as solvent (1/0 to 3/7) to afford the desired product as a yellow oil (5 g).

1H NMR (CDC13, 400MHz): d = 7.78 - 7.87 (m, 2 H), 7.42 - 7.40 (m, 2 H), 7.33 (m, 1 H), 7.16 (d, 2 H), 5.69 (d, 1 H), 5.02 - 5.26 (m, 1 H), 2.02 (s, 3 H), 1.48 - 1.51 ppm (d, 3 H)

Step 2:

To a solution of N-[(lS)-l-[4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2-e noyl]phenyl]ethyl]acetamide (100 mg) in 1 ,2-dichloroethane (4 mL) was added tetrabutylammonium hydrobromide (40 mg), hydroxylamine (0.03 mL, 50% in water) and sodium hydroxide (0.46 mL, 1M) at room temperature. The solution was stirred at room temperature for 6 hours then a solution of saturated ammonium chloride was added. The mixture was extracted with DCM then washed with brine. The organic layers were combined and dried over magnesium sulphate, filtered then concentrated under reduced pressure to give a yellow oil which was purified by chromatography on column (Heptane/EtOAc as solvent (1/0 to 1/1) to afford the desired product as a yellow oil (77 mg).

lU NMR (CDC13, 400MHz): d = 7.59 - 7.69 (m, 2 H), 7.49 - 7.57 (m, 2 H), 7.43 (t, J=1.8 Hz, 1 H), 7.34 - 7.41 (m, J=8.4 Hz, 2 H), 5.65 (d, J=7.3 Hz, 1 H), 5.15 (t, J=7.2 Hz, 1 H), 4.01 - 4.13 (m, 1 H), 3.68 (d, J=17.2 Hz, 1 H), 2.01 (s, 3 H), 1.50 (d, J=7.0 Hz, 3 H), 1.27 ppm (t, J=7.2 Hz, 1 H).

Example 4: Preparation of 2-(l ,2,4-triazol-l -yl)-5-r3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-2,4- dihydropyrrol-5-yllbenzonitrile Step 1 : Preparation of 3-bromo-4-fluoro-N-(trimethylsilylmethyl)benzamide

To a solution of 3-bromo-4-fluoro-benzoic acid (500 mg, 2.2830 mmol) in dichloromethane (15 niL) was added N,N-dimethylpyridin-4-amine (28mg, 0.22830 mmol) , EDCI HC1 (570mg, 2.9679 mmol). To this was added trimethylsilylmethanamine (260mg, 2.51 13 mmol) and the reaction was stirred at room temperature under nitrogen atmosphere overnight and monitored by TLC. The reaction mass was diluted with water (10 mL) and extracted with DCM (3 x 50 niL). The combined organic layer was dried over sodium sulphate and concentrated under vacuum. Purification by chromatography (hexane/ethyl acetate) provided 3-bromo-4-fluoro-N-(trimethylsilylmethyl)benzamide (550 mg, ).

¾ NMR (400MHZ, CDC13): 7.94(dd,lH); 7.65(m,lH); 7.15(t, 1H); 5.9(brs, 1H); 2.94(d, 2H); 0.12(s, 9H), LCMS (methanol, ESI): retention time = 2.06, m/z = 302.0(M-H)

Step 2: Preparation of 3-cyano-4-fluoro-N-(trimethylsilylmethyl)benzamide

In a sealed tube was taken a solution of 3-bromo-4-fluoro-N-(trimethylsilylmethyl)benzamide (10 g, 32.870 mmol) in N,N-dimethylformamide (60 mL) was added zinc formonitrile (7.85 g, 65.740 mmol) followed by palladium(0)tetrakis(triphenylphosphine) (7.61 g, 6.5740 mmol) . The reaction was degassed and purged with nitrogen and stirred at 100°C for 4-5 hours. The reaction was diluted with water (100 mL) extracted with ethylacetate (3 x 100 mL), and washed with sodium bicarbonate (50 mL) . The combined organic layer was dried over sodium sulphate and concentrated under vacuum. Purification by chromatography (hexane/ethyl acetate) provided 3-cyano-4-fluoro-N- (trimethylsilylmethyl)benzamide(6.7 g)

¾ NMR (400MHZ, CDC13): 7.98-8.02(m, 2H); 7.3(m, 1H); 5.94(brs, 1H); 2.95-2.98(m, 2H); 0.13(s, 9H). LCMS (methanol, APCI): retention time = 4.1 1 , m/z = 249.09(M-H) Step 3: Preparation of 3-cyano-4-fluoro-N-(trimethylsilylmethyl)benzenecarbothioami de

A solution of 3-cyano-4-fluoro-N-(trimethylsilylmethyl)benzamide (6.5 g, 26 mmol) and 2,4-bis(4- methoxyphenyl)-2,4-dithioxo-l,3,2,4-dithiadiphosphetane (1 lg, 26 mmol) in tetrahydrofuran (75 mL) was refluxed for 2 hours. The reaction mass was concentrated to remove THF, diluted with water (50 mL), and extracted with ethylacetate (3 x 100 mL). The combined organic layer was dried over sodium sulphate and concentrated under vacuum. Purification by chromatography (hexane/ethyl acetate) provided 3-cyano-4-fluoro-N-(trimethylsilylmethyl) benzenecarbothioamide (4.8g).

¾ NMR (400MHZ, CDC13): 8.2(m,lH); 7.93-7.99(m,lH); 7.64(brs, lH);7.22(m,lH); 3.52(d, 2H); 0.18(s, 9H), LCMS (methanol, APCI): retention time = 4.55, m/z = 265.45(M-H). Step 4: Preparation of 2-fluoro-5-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-2, 4-dihydropyrrol-5- ljbenzonitrile

To a solution of 3-cyano-4-fluoro-N-(trimethylsilylmethyl)benzenecarbothioami de (4 g, 15.02 mmol) in N,N-dimethylformamide (40 mL) was added dipotassium carbonic acid (5.26 g, 37.54 mmol). To this was added iodomethane (21.31 g, 150.2 mmol). The reaction mass was stirred at room temperature for 3 hours and monitored by TLC. The reaction mass was quenched with water (10 mL) and extracted with ethylacetate (3 x 50mL). The combined organic layer was dried over sodium sulphate and concentrated under vacuum to give methyl-3-cyano-4-fluoro-N-(trimethylsilylmethyl) benzenecarboximidothioate. To a -5°C cooled solution of methyl-3-cyano-4-fluoro-N-(trimethylsilylmethyl)

benzenecarboximidothioate (4 g, 14.27 mmol) and l,2,3-trichloro-5-[l-(trifluoromethyl)vinyl]benzene (3.97g., 14.41 mmol) in tetrahydrofuran (5 mL) was slowly added tetrabutylammonium hydrofluoride (7.13 mL, 7.133 mmol, 1 mol/L) . The reaction was stirred at -5°C for 30 mins, then allowed to come to room temperature, and stirred at room temperature for 2 hours under nitrogen atmosphere. The reaction was diluted with water (50 mL) and extracted with ethylacetate (3 x 100 mL). The combined organic layer was dried over sodium sulphate and concentrated under vacuum. Purification by chromatography (hexane/ethyl acetate) provided 2-fluoro-5-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-2, 4- dihydropyrrol-5-yl]benzonitrile (2.5 g).

lU NMR(400MHz, CDC1 ₃ ): 8.04-8.13(m, 2H); 7.37(s, 2H); 7.35(m, 1H); 4.82(dd, 1H); 4.36(d, 1H); 3.7(dd, 1H); 3.35(d, 1H) ,LCMS (methanol, APCI): retention time = 5.05, m/z = 434.88(M+H)

Step 5: Preparation of 2-(l ,2,4-triazol-l-yl)-5-[3-(3,4,5-trichlorophenyl)-3-(trifluoro methyl)-2,4- dihydropyrrol-5-yl]benzonitrile

A solution of 2-fluoro-5-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-2, 4-dihydropyrrol-5- yljbenzonitrile (1.0 g, 2.3 mmol) , dipotassium carbonic acid (390 mg, 2.8 mmol) and lH-l,2,4-triazole (190mg, 2.8 mmol) were heated at 120 C for 2-3 hours and monitored by TLC. The reaction was diluted with water (10 mL) and extracted with ethylacetate (3 x 30 mL). The combined organic layer was dried over sodium sulphate and concentrated under vacuum. Purification by chromatography (hexane/ethyl acetate) provided 2-(l ,2,4-triazol-l-yl)-5-[3-(3,4,5-trichlorophenyl)-3-(trifluoro methyl)-2,4- dihydropyrrol-5-yl]benzonitrile as solid (950 mg). Melting point: 162-164 C.

'H NMR (400MHZ, CDC1 ₃ ): 8.9(S, lH), 8.29-8.34(m, 2H); 8.21(s, 1H); 7.93(d, 1H); 7.40(s, 2H); 4.94(d, 1H); 4.51(d, 1H); 3.84(d, 1H); 3.54(d, 1H);, LCMS (methanol, APCI): retention time =4.96, m/z = 483.94(M+H)

Example 5: Preparation of N-[(l S)-l-r4-[5-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-2,4-d ihydropyrrol- 3-yllphenyllethyllcyclopropanecarboxamide

Ste 1 : Preparation of tert-butyl N-[(lS)-l-(4-bromophenyl)ethyl ^" |carbamate

To a stirring solution of compound (l S)-l-(4-bromophenyl)ethanamine (50 mmol) in a 50 mL roundbottom flask and tert-butoxycarbonyl tert-butyl carbonate (50 mmol) was added over period of 20 min and stirring was continued vigorously, After 5 min solid was precipitated out from reaction mass and thus obtained solid was filtered and washed with hexane and dried under vacuum. Weight: 13 g

'H-NMR (400 MHz, CDC1 ₃ ): 7.45(2H, d), 7.18(2H, d), 4.74(1H, m), 1.40-1.48 (12H, m).

Step 2: Preparation of 4-[(lS)-l-(tert-butoxycarbonylamino)ethyl]benzoic acid

To a stirring solution of compound tert-butyl N-[(lS)-l-(4-bromophenyl)ethyl]carbamate (1 g, 3.331 mmol) in THF (30 mL) cooled to -78°C, methyl lithium (5.33 mmol, 1.6 eq.) was added drop wise under nitrogen atmosphere and stirring was continued for 15 mins followed by addition of butyllithium (5.33 mmol, 1.6 eq.) drop wise and stirring was continued for 30 mins. Dry carbon dioxide was added and stirring continued for 1 hour at -70 C to room temperature. The reaction mass was quenched with water (50 mL) and the compound was extracted with ethylacetate (30 mL x 2) in order to remove debromo compound. The aqueous layer was acidified with ammonium chloride and extracted with ethylacetate (30 mL x 2). The combined organic layers were dried with sodium sulfate and evaporated off under vacuum and dried under vacuum. Weight: 0.61 g

¾-NMR (400 MHz, CDC1 ₃ ): 7.86(2H, d), 7.37(2H, d), 4.64(1H, m), 1.28-1.31 (12H, m). LC-MS (methanol, ESI): m/z =264(M-H), RT 1.95-2.07.

Ste 3: Preparation of tert-butyl N-[(l S)-l-[4-(trimethylsilylmethylcarbamoyl)phenyl]ethyl]carbamat e

To a stirring solution of 4-[(lS)-l -(tert-butoxycarbonylamino)ethyl]benzoic acid (1 g, 3.769 mmol), 1- hydroxybenzotriazole hydrate (542 mg, 3.5mmol) in DMF (5 mL), in DCM (30 mL),

trimethylsilylmethanamine (0.38 g, 3.7 mmol), trimethylsilylmethanamine (0.38 g, 3.7 mmol) and the reaction mass was cooled to 0°C and 3-(ethyliminomethyleneamino)-N,N-dimethyl-propan-l-amine hydrochloride (848 mg, 4.4234 mmol) was added and the reaction was stirred at 0°C to room temperature overnight. TLC showed the reaction was completed. The reaction mass was quenched with water (30 mL) and extracted with DCM (35 mL x 2) and the combined organic layer was washed with water (20 mL x 2) and dried with sodium sulfate and evaporated of under reduced pressure and compound was purified by combiflash. Weight: 0.93 g

¾-NMR (400 MHz, CDC1 ₃ ): 7.68 (2H, d), 7.34(2H, d), 5.93(1H, m). 4.81 (2H, d), 2.95(2H, d), 1.40-1.45 (12H, m). LC-MS (methanol, ESI): m/z =349(M-H), RT 1.95-2.07 . Step 4: Preparation of tert-but l N-[(l S)-l -[4(trimethylsilylmethylcarbamothioyl)phenyl]ethyl]carbamate

To a solution of tert-butyl N-[(l S)-l -[4-(trimethylsilylmethylcarbamoyl)phenyl]ethyl]carbamate (1 g, 2.853 mmol) in THF (25 niL) was added 2,4-bis(4-methoxyphenyl)-l ,3,2,4-dithiadiphosphetane-2,4- disulfide (1 eq, 2.853 mmol,) and reaction mass was stirred at 65 °C for 4hours. TLC showed the reaction was completed. The solvent was removed from the reaction mass on a rotary evaporator and the resultant reaction mass was diluted with ethylacetate and washed with water (twice). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude mass thus obtained was purified by combiflash (silica gel). Weight: 0.8 g

'H-NMR (400 MHz, CDC1 ₃ ): 7.65 (2H, d), 7.51 -7.52 (1H, m), 7.30(2H, d), 4.76-4.81 (2H, m), 3.51 (2H, d), 1.40-1.45 (12H, m). LC-MS (methanol, ESI): m/z =365 (M-H), RT 2.51 -2.57.

Step 5: Preparation of tert-butyl N-[(l S)-l -[4-[5-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-2,4- dihydropyrrol-3-yl]phenyl]ethyl]carbamate

To stirring solution of compound tert-butyl N-[(l S)-l -[4-

(trimethylsilylcarbamothioyl)phenyl] ethyl] carbamate (0.5 g, 1 mmol) in DMF (25 mL), potassium carbonate (2 eq., 2 mmol) was added followed by addition of iodomethane (10 eq., 10 mmol) over period of 1 hour and stirring was continued for 3 ours. After completion of the reaction (monitored by TLC), the reaction mass was diluted with ethylacetate and washed with water (20 mL x 3) and dried with sodium sulphate and evaporated off under vacuum. The obtained reaction mass was taken into THF (25 mL) and l ,2,3-trichloro-5-[l -(trifluoromethyl)vinyl] benzene (1 eq., 1 mmol) was added into it. The mixture was cooled to 0°C, TBAF (1 eq, 1 mmol) was added and stirring was continued for 3 hours at room temperature. After completion of the reaction (monitored by TLC), the solvent was evaporated off under vacuum and the reaction mass was diluted with ethylacetate and washed with water (30 mL x 2) and dried with sodium sulphate and evaporated off under vacuum. The compound was purified by combiflash, (25-30% EtOAC-hexane). Weight: 0.1 lg 'H-NMR (400 MHz, CDC1 ₃ ): 7.97 (2H, d), 7.33-7.56 (4H, m), 4.85-4.92 (2H, m), 4.50 (1H, dd), 3.91 (1H, dd), 3.58 (1H, dd), 1.40-1.45 (12H, m). LC-MS (methanol, ESI): m/z = 533 (M-H), RT 2.51 -2.57.

Step 6: Preparation of N-[(l S)-l -[4-[5-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-2,4-dihyd ropyrrol-3- yl]phenyl]ethyl]cyclopropanecarboxamide

To a solution of tert-butyl N-[(l S)-l -[4-[5-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-2,4-dihyd ropyrrol- 3 -yl]phenyl] ethyl] carbamate (0.35 g) in DCM (20 mL) was added 2,2,2-trifluoroacetic acid (3 eq.) and the reaction mass was stirred for 5 hours at room temperature. After completion of the reaction, the solvent was removed under vacuum and the compound thus obtained was directly taken for the next step. A Solution of (l S)-l -[4-[5-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-2,4-dihyd ropyrrol-3- yl]phenyl]ethanamine TFA salt ( 0.3 g, 0.7 mmol), in DCM (20 mL) was cooled at 0°C. To the cooled mixture was added triethylamine (2.2 eq, 1.54 mmol) followed by dropwise addition of cyclopropane carboxylic acid chloride (1 eq., 0.7 mmol) over period of 5 min and stirring was continued overnight. After completion of the reaction (monitored by TLC), the reaction mass was diluted with DCM (20 mL) and washed with water (20 mL). The organic layer was then dried over anhydrous sodium sulphate, and the solvent was removed under vacuum. The compound was purified by Combiflash (35 % EtOAC- hexane). Weight: 0.2 g, melting point: 80-82°C.

'H-NMR (400 MHz, CDCI ₃ ): 7.82(2H, d), 7.35-7.41 (4H, m), 6.05 (1H, m), 5.13 (1H, m), 4.86 (1H, dd), 4.42 (1H, dd), 3.78 (1H, dd), 3.45 (1H, dd). 1.46-1.50 (4H, m), 0.93-0.96 (2H, m), 0.72-0.731 (2H, m) LC-MS (methanol, ESI): m/z = 501 (M-H), RT 2.23-2.30.

Example 6: Preparation of N- {2-bromo-4- | ^" 4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro-3H- pyrrol-2yll -benzyl} acetamide. Step 1 : Bromination of 3-bromo-4-methyl benzoic acid.

3-bromo-4-methyl benzoic acid (10 g, 46.72 mmol), NBS (8.7 g, 49.15 mmol)) and benzoylperoxide (0.5 g, 2 mmol)) were suspended in CCI ₄ and then heated to reflux for 5 hours. After completion of the reaction (TLC monitoring) water was added to the reaction mixture. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated in vaccuo. The crude mixture thus obtained containing 3-bromo-4-bromomethyl benzoic acid and the 3-bromo-4-dibromomethyl benzoic acid was taken directly into the next step.

LC-MS (methanol, ESI): m/z =291 (M-H) and 368 (M-H)

Step 2: Preparation of 3-bromo-4-(dibromomethyl)-N-[(trimethylsilyl)methyl]benzamid e.

A mixture of of 3-bromo-4-(bromomethyl)-N-[(trimethylsilyl)methyl]benzamide and 3-bromo-4- (dibromomethyl)-N-[(trimethylsilyl)methyl]benzamide (19 g, 51 mmol), 1 -(trimethylsilyl)methylamine (5.78 g, 56 mmol), N,N-dimethylaminopyridine (0.1 g) and N-(3-dimethylaminopropyl)-N'- ethylcarbodiimide.HCl (12.74 g, 66 mmol) was dissolved in tetrahydrofuran solvent and stirred for 1 hour at room temperature. After completion of the reaction (TLC monitoring), the reaction mixture was concentrated on a rotary evaporator. Water was added to the reaction mixture, followed by extraction with ethylacetate. The organic layer was separated and dried using sodium sulphate. The residue was purified by silica gel chromatography to obtain 3-bromo-4-(dibromomethyl)-N-[(trimethylsilyl) methyl] benzamide (16 g).

LC-MS (methanol, ESI): m/z =456 (M+H).

IH-NMR (400 MHz, CDC13): 8.01 (1H, dd), 7.87(1H, d), 7.04(1H, dd), 6.13(lH,bs) , 3.51 (2H, d), 0.17 (9H,s).

Step 3: Preparation of 3-bromo-4-formyl-N-[(trimethylsilyl)methyl]benzamide.

3-bromo-4-(dibromomethyl)-N-[(trimethylsilyl)methyl]benzamid e (0.25 g, 0.69 mmol) was taken in acetone (5 mL) and water (2.5 mL). Silver nitrate (0.3 g, 1.7 mmol) was added to the reaction mixture. The reaction was stirred at room termperature for 6 hours. The reaction mass was then concentrated and extracted with ethylacetate. The organic layer was separated and dried using sodium sulphate. The organic layer was concentrated to obtain the product 3-bromo-4-formyl-N- [(trimethylsilyl)methyl]benzamide. (0.15 g).

LC-MS (methanol, ESI): m/z =314(M+H).

1H-NMR (400 MHz, CDC13): 10.33(lH,s),7.90 (1H, m), 7.60 (1H, dd), 7.56 (1H, m), 5.99(lH,s),2.99 (2H, d), 0.17 (9H,s).

Step 4: Preparation of 3-bromo-4-hydroxymethyl-N-[trimethylsilaylmethyl] benzamide.

3-bromo-4-formyl-N-[(trimethylsilyl)methyl]benzamide(0.1 g, 0.3 mmol) was dissolved in methanol and to this was added NaBH ₄ (0.014 g, 0.38 mmol). The reaction was stirred at room temperature for 1 hour. Methanol was removed under vaccuo and water was added to the reaction mass which was then extracted using ethyl acetate. The organic layer was separated and dried using sodium sulphate followed by concentration to get the product 3-bromo-4-hydroxymethyl-N-[trimethylsilaylmethyl] benzamide (0.05 g).

LC-MS (methanol, ESI): m/z =316 (M+H).

1H-NMR (400 MHz, CDC13): 7.90 (1H, m), 7.60 (1H, m), 7.53 (1H, m), 6.02(1H, s),4.75

(2H,s),2.99(2H,s), 0.17 (9H,s).

Step 5: Preparation of Acetic acid 2-bromo-4- (trimethylsilanylmethyl-carbamoyl)-benzylester.

3-bromo-4-hydroxymethyl-N-[trimethylsilaylmethyl] benzamide (0.25 g, 0.7 mmol) was dissolved in DMF solvent, triethyl amine (0.159 g, 1.5 mmol) and acetyl chloride (0.061 g, 0.8 mmol) were added to the reaction mixture at room temperature. The reaction was stirred at room temperature for 30 min. Water was added and the reaction mass was then extracted with ethyl acetate. The organic layer was separated, dried using sodium sulphate and concentrated to get the product: acetic acid 2-bromo-4- (trimethylsilanylmethyl-carbamoyl)-benzylester (0.15 g).

LC-MS (methanol): m/z =358 (M+H).

'H-NMR (400 MHz, CDC13): 7.90 (1H, m), 7.60 (1H, m), 7.38 (1H, m), 6.14(1H, bs), 5.11(2H, s), 2.99 (2H, d), 2.15 (3H, s), 0.17 (9H, s). Step 6: Preparation of 3-bromo-4-(2-oxo-propyl)-N-trimethylsilanylmethyl-thiobenzam ide.

Acetic acid 2-bromo-4- (trimethylsilanylmethyl-carbamoyl)-benzylester (2.4 g, 7.6 mmol) and Lawesson reagent (2.7 g,6.6 mmol) were suspended in THF. The mixture was heated to reflux for 3 hours, concentrated, washed with water and extracted with ethyl acetate. The organic layer was separated and dried using sodium sulphate. The residue was purified by silica gel chromatography to obtain 3-bromo-4- (2-oxo-propyl)-N-trimethylsilanylmethyl-thiobenzamide (1.8 g).

LC-MS (methanol, ESI): m/z =374(M+H).

'H-NMR (400 MHz, CDC13): 7.90 (1H, m), 7.60 (1H, m), 7.38 (1H, m), 6.01(1H, br s), 5.11 (2H, d), 2.99 (2H, d), 2.15 (3H, s), 0.17 (9H, s)

Step 7: Preparation of Acetic acid 2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro- 3H-pyrrol-2yl] -benzylester.

A mixed solution of methyliodide (0.69 g,4.8 mmol), potassium carbonate (0.80 g, 5.7 mmol) and 3- bromo-4-(2-oxo-propyl)-N-trimethylsilanylmethyl-thiobenzamid e (1.8 g, 5.4 mmol) in DMF (25 mL) was stirred at 0°C for 4 hours.The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layer was separated, dried using sodium sulphate and concentrated to get the crude acetic acid 2-bromo-4 {methylsulfanyl-[(E)- trimethylsilanylmethylimino]-methyl} -benzyl ester.(0.95g) which was dissolved in THF and cooled to 0°C under nitrogen atmosphere. A solution of TBAF (1.0 M in THF) (0.56 mL) was added gradually into it and reaction mixture was stirred for 8 hours at room temperature. The reaction mass was then concentrated and extracted with ethylacetate. The organic layer was separated and dried using sodium sulphate. The resulting mixture was then purified by silica gel chromatography to obtain acetic acid 2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro- 3H-pyrrol-2yl] -benzylester ( 1.1 g).

LC-MS (methanol, ESI): m/z =508 (M+H).

'H-NMR (400 MHz, CDC13): 8.07 (1H, m), 7.71 (1H, m), 7.47 (1H, m), 7.38 (1H, m), 7.24(2H, m), 5.23(2H, s), 4.90 (1H, m),4.43 (1H, d), 3.75 (1H, m), 3.43 (1H, d), 2.17 (3H, s). Step 8: Preparation of 2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2yl]- phen l-methanol.

To a solution of acetic acid 2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro-3H- pyrrol-2yl]-benzylester (1.1 g, 2.1 mmol) in methanol (20 mL) was added sodium methoxide (0.1 g, 1.85 mmol) and the solution was stirred for 1 hour at room temperature. The reaction mass was then concentrated and extracted with ethylacetate. The organic layer was separated and dried using sodium sulphate. The resulting mixture was then purified by silica gel chromatography to obtain 2-bromo-4- [4- (3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2yl]-phenyl-methan ol (0.95g).

LC-MS (methanol, ESI): m/z =466 (M+H).

'H-NMR (400 MHz, CDC13): 8.07 (1H, m), 7.78 (1H, m), 7.59 (1H, m), 7.38 (3H, m), 4.90 (3H, d),4.43 (1H, d), 3.75 (1H, m), 3.43 (1H, d). Step 9: Preparation of Methanesulfonic acid-2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5- dih dro-3H-pyrrol-2yl]-benzylester.

To a solution of 2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2yl]- phenyl-methanol (0.95 g, 2 mmol) and triethylamine (0.4 g, 4.0 mmol) in THF was added

methanesulfonyl chloride (0.35 g, 3.0 mmol) gradually. The mixture was stirred for 1 hour at room temperature. The reaction mixture was washed with water. The organic layer was separated and dried using sodium sulphate. The organic layer was evaporated to obtain the solid compound methanesulfonic acid-2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2yl]-benzylester (0.9 g).

LC-MS (methanol, ESI): m/z =544 (M+H).

'H-NMR (400 MHz, CDC13): 8.13 (1H, m), 7.81 (1H, m), 7.58 (1H, m), 7.38 (1H, m),

7.24(2H,m),5.36(2H, s), 4.90 (1H, m),4.43 (1H, d), 3.75 (1H, m), 3.43 (1H, d), 3.04 (3H,s). Step 10: Preparation of 2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro-3H-pyrrol- 2 l] -benzylamine.

To a solution of methanesulfonic acid-2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5- dihydro-3H-pyrrol-2yl]-benzylester (1.0 g,1.8 mmol) in THF (30 mL) and MeOH (30 mL) was added dropwise to a mixed solution of aq. ammonia (30%), 30 mL, and the reaction was stirred for 12 hours at room temperature. The reaction mass was then concentrated and extracted with ethylacetate. The organic layer was separated and dried using sodium sulphate. The organic layer was evaporated to provide the gummy compound 2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2yl]- benzylamine.

LC-MS (methanol, ESI): m/z = 467(M+H).

'H-NMR (400 MHz, CDC13): 8.07 (1H, m), 7.71 (1H, m), 7.59 (1H, m), 7.38 (1H, m), 7.24(2H,m), 4.90 (1H, d),4.43 (3H, m), 3.75 (1H, m), 3.43 (1H, d). Step 1 1 : Preparation of N- {2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro-3H- pyrrol-2yl] -benzyl} acetamide.

To a solution of 2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2yl]- benzylamine (0.15 g, 0.32 mmol) in THF was added acetic anhydride (0.04 g, 0.39 mmol) and the mixture was stirred at room temperature for 1 hour. The reaction mass was then concentrated under reduced pressure and extracted with ethylacetate. The organic layer was separated and dried using sodium sulphate. The resulting mixture was then purified by silica gel chromatography to obtain N- {2-bromo-4- [4-(3,5-dichlorophenyl )-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2yl]-benzyl} acetamide.

LC-MS (methanol,ESI): m/z = 509 (M+H).

'H-NMR (400 MHz, CDC13): 8.07 (1H, m), 7.71 (1H, m), 7.47 (1H, m), 7.38 (1H, m),

7.24(2H,m),5.98(lH, s), 4.90 (1H, d),4.43 (3H, m), 3.75 (1H, m), 3.43 (1H, d), 2.04 (3H,s).

Example 7: Preparation of N- {4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidinl -yll- 2-methyl- benzyPacetamide.

Step 1 : Preparation of l-Benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidi ne.

To a cooled solution of l,3-dichloro-5(l-trifluoromethyl)vinyl)benzene (0.5 g, 2.0 mmol) and N-benzyl- l-methoxy-N-9trimethylsilyl)methyl)methanamine (0.4 g, 2.0 mmol) in DCM (10 mL) was added dropwise a solution of TFA (0.024 g, 0.2 mmol) in DCM (1 mL). The reaction mixture was stirred for 3 hours at room temperature. The organic layer was washed with water (2 x 10 mL) and 10% aq sodium carbonate solution (10 mL). The organic layer was separated, dried with sodium sulphate and concentrated under reduced pressure The residue was purified by silica gel chromatography to yield 1- Benzyl-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (0.5 g).

LC-MS (methanol, ESI): m/z = 374 (M+H).

'H-NMR (400 MHz, CDC13): 7.36 (4H, m), 7.30(2H, m), 7.23 (2H, m), 3.67 (2H, s), 3.08 (2H, dd), 2.69 (2H,m), 2.53 (1H, m), 2.27(lH,m).

Step 2: Preparation of 3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine.

To a solution of l-benzyl-3-( -(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (0.22 g, 0.59 mmol) and l-chloroethylchloroformate(0.17 g, 1.2 mmol) in DCM was heated for reflux for 3 hours. The mixture was cooled to room temperature and concentrated under reduced pressure. Methanol was added to the residue which was then heated with stirring for 3 hours at 60°C. The mixture was concentrated and water was added to it. The residue was extracted with ethylacetate (20 mL x 3) washed with brine, dried over sodium sulphate and concentrated under reduced pressure. Purification over silica gel yielded 3- (3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (4.2 g).

LC-MS (methanol, ESI): m/z = 284 (M+H).

'H-NMR (400 MHz, CDC13): 7.35 (1H, t), 7.25 (2H, d), 3.74 (1H, d), 3.19 (2H, m), 2.97(lH,m),2.53 (1H, m), 2.27(lH,m). Step 3: Preparation of N-(4-bromo-2-methyl-benzyl)acetamide.

4-bromo-2-methyl benzonitrile (2.0 g, 0.01 mol) was taken in methanol along with Νί(¾ (2.41 g, 0.01 mol). In the same pot acetic anhydride was taken (2.0 g, 0.020 mol). The reaction was cooled to 0°C. NaBH ₄ (2.7 g, 0.07 mol) was added slowly to the reaction while stirring at the same temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and was extracted with ethylacetate. The organic layer was separated, dried using sodium sulphate and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography to yield N-(4-bromo-2-methyl- benzyl)acetamide.(l . l g).

LC-MS (methanol, ESI): m/z = 242 (M+H).

1H-NMR (400 MHz, CDC13): 7.71 (1H, m), 7.47 (1H, m), 7.38 (1H, m), 5.98(1H, s), 3.75 (1H, m), 3.43 (1H, d), 2.31 (3H, s),2.04 (3H, s).

Step 4: Preparation of N- {4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidinl-yl ]- 2-methyl- benz l)acetamide.

To the mixture of 3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (0.25 g, 0.88 mmol) and the N- (4-bromo-2-methyl-benzyl)acetamide (0.8 g, 0.7 mmol) in anhydrous toluene under nitrogen atmosphere was added tris(dibenzylidineacetone)dipalladium (0.02 g, 0.02 mmol) and the ligand xanthphos (0.03 g, 0.053 mmol) followed by the addition of sodium tertiary butoxide (0.127 g, 1.3 mmol). The reaction mixture was heated at 80°C for 3hours. After completion of the reaction (TLC monitoring), the reaction mass was filtered over celite. The filtrate was concentrated and purified using column chromatography. LC-MS (methanol, ESI): m/z = 445 (M+H).

1H-NMR (400 MHz, CDC13): 7.37 (1H, d), 7.29 (2H, m), 7.11 (1H, d), 6.41 (2H, m), 5.45(lH,b s), 4.35 (2H, s),4.01 (1H, d), 3.75 (1H, d), 3.43 (2H, m), 2.81 (lH,d),2.51 (lH,d),2.31 (3H,s),1.97 (3H,s).

The following examples were prepared according to methods described in US 2009/0156643 and were analysed by the LCMS methods described below: Method A: ZQ Mass Spectrometer from Waters (Single quadrupole mass spectrometer)

Instrument Parameter:

Ionization method: Electrospray

Polarity: positive and negative ions

Capillary: 3.00 kV

Cone: 30.00 V

Extractor: 2.00 V

Source Temperature: 100°C,

Desolvation Temperature: 250°C

Cone Gas Flow: 50 L/Hr

Desolvation Gas Flow: 400 L/Hr

Mass range: 100 to 900 Da HP 1100 HPLC from Agilent:

Solvent degasser, quaternary pump, heated column compartment and diode-array detector.

Type of column: Phenomenex Gemini CI 8; Column length: 30 mm; Internal diameter of column: 3 mm;

Particle Size: 3 micron; Temperature: 60°C.

DAD Wavelength range (nm): 210 to 500

Solvent Gradient:

A = H20 + 5% MeOH + 0.05 % HCOOH

B= Acetonitril + 0.05 % HCOOH

Time A% B% Flow (mL/min)

0.00 100 0 1.700

2.00 0 100.0 1.700

2.80 0 100.0 1.700

2.90 100 0 1.700

3.00 100 0 1.700 Method B:

ACQUITY SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer)

Ionisation method: Electrospray

Polarity: positive ions

Capillary (kV) 3.00, Cone (V) 20.00, Extractor (V) 3.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 400, Cone Gas Flow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700

Mass range: 100 to 800 Da DAD Wavelength range (nm): 210 to 400

Method Waters ACQUITY UPLC with the following HPLC gradient conditions

(Solvent A: Water/Methanol 9: 1,0.1% formic acid and Solvent B: Acetonitrile,0.1%> formic acid ) Time (minutes) A (%) B (%) Flow rate (mL/min)

0 100 0 0.75

2.5 0 100 0.75

2.8 0 100 0.75

3.0 100 0 0.75

Type of column: Waters ACQUITY UPLC BEH C18; Column length: 50 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.7 micron; Temperature: 60°C.

Example 8:

Method A, retention time 2.17 min, MH+ 511

Example 9:

Method B, retention time 1.98 min, MH+ 479 The following Example was prepared according to methods described in WO 2008/150393. Example 11 :

Method A, retention time 2.1 min, MH+ 470 The following Example was prepared according to methods described in WO 2009/051956.

Example 12:

1H NMR in CDC13: 3.73 ppm (d, 1H), 4.12 ppm (d, 1H), 7.58 ppm (d, 2H), 7.93 (m, 1H), 8.07-8.12 (m, 3H), 8.62 (s, 1H)

Example 13: Preparation of 5-bromo-N-hydroxyindan-l-imine:

A solution of 5-bromoindane-l-one (10.0 g, 47.38 mmol) in methanol (50 mL), treated with

hydroxylamine hydrochloride (3.65 g, 52.17 mmol) and sodium acetate (4.27 g, 52.17 mmol) and stirred at room temperature for 20 hours. The solvent was evaporated, and the residue was treated with water (25 mL) and extracted with ethylacetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate and concentrated to give 5-bromo-N-hydroxyindan-l -imine (10 g). 'H-NMR (400 MHz, CDC1 ₃ ): 7.65 (1H d), 7.5 (1H, s), 7.4 (1H, d), 3.05 (2H, m), 3.10 (2H, m). LC-MS (methanol, ESI): m/z = 227 (M+H, retention time = 1.75).

Example 14: Preparation ofter-butyl (5-bromo-2,3-dihydro-lH-inde-l-yl)carbamate:

A solution of 5-bromo-N-hydroxyindan-l-imine (16 g, 70.77 mmol) in methanol (400 mL) and dioxane (200 mL) was treated with di-ter-butyl bicarbonate (31 g, 141.55mmol) and nickel chloride (4.68 g, 35.39 mmol). The reaction mixture was cooled to -20 C, sodium borohydride (10.7 g, 283.1 mmol) was added slowly and stirred for lhour. The reaction mixture was then treated with diethylenetriamine (16 mL), and stirred for 30 min. The reaction mixture was diluted by adding water, extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated and purified by column chromatography (hexane/ethylacetate 1 :9 as eluent) to give ter-butyl (5-bromo-2,3-dihydro-lH-inde-l- yl)carbamate (10.5 g). 'H-NMR (400 MHz, CDC1 ₃ ): 7.1 (1H, d), 7.2 (1H, s), 7.3 (1H, d), 5.15 (1H, m), 4.7 (1H, m), 2.9 (1H, m), 2.8 (1H, m), 2.5 (1H, m), 1.8 (1H, m), 1.45 (s, 9H).

Example 15: Preparation of l-(tert-butoxycarbonylamino)indane-5-carboxylic acid:

A solution of ter-butyl (5-bromo-2,3-dihydro-lH-inde-l-yl)carbamate (10 g, 32 mmol) in tetrahydrofuran (200 mL) was cooled to -78 °C, treated dropwise with methyl lithium (16 mL, 48 mmol) and stirred for 10 min, followed by addition of n-BuLi (29 mL, 64 mmol) and further stirred for 1 hour. The reaction mixture was treated with dry ice slowly and stirred for 30 min. It was then quenched with a saturated solution of ammonium chloride and extracted with ethylacetate (2 x 50 mL). The combined organic layers were dried over sodium sulfate, concentrated under reduced pressure to afford crude solid material, and then triturated with hexane/diethyl ether to afford pure l-(tert-butoxycarbonylamino)indane-5-carboxylic acid (3.8 g). 'H-NMR (400 MHz, DMSO): 7.8 (1H, s), 7.3 (1H, m), 7.2 (1H, m), 5.00 (1H, m), 2.9 (1H, m), 2.8 (1H, m), 2.31 (1H, m), 1.8 (1H, m), 1.45 (s, 9H). LC-MS (methanol, ESI): m/z = 276 (M-H, retention time = 1.74).

Example 16: Preparation of tert-butyl N-[5-(trimethylsilylmethylcarbamoyl)indan-l -yllcarbamate:

A solution of l-(tert-butoxycarbonylamino)indane-5-carboxylic acid (2.1 g, 7.6 mmol) in

dichloromethane (20 mL), was treated trimethylsilyl methylamine (0.88 g, 8.3 mmol), EDCI (1.4 g, 9.1 mmol) and a catalytic amount of DMAP (0.09 g, 0.76 mmol), and stirred for 20 hours. The reaction mixture was then treated with water (10 mL) and extracted with dichloromethane (2 x 25 mL). The combined organic layers were dried over sodium sulfate, concentrated, and purified by column chromatograph (hexane/ethylacetate as eluent) to afford tert-butyl N-[5-

(trimethylsilylmethylcarbamoyl)indan-l-yl]carbamate (1.9 g). 'H-NMR (400 MHz, CDC13): 7.6 (IH, s), 7.53 (IH, d), 7.33 (IH, d), 6.00 (IH, m), 5.2 (IH, m), 4.8 (IH, m), 3.0 (IH, m), 2.9 (2H, d), 2.8 (IH, m), 2.6 (IH, m), 1.8 (IH, m), 1.45 (s, 9H), 0.2 (s, 9H). LC-MS (methanol, ESI): m/z = 363 (M+H, retention time = 2.05).

Example 17: Preparation of tert-butyl N-[5-(trimethylsilylmethylcarbamothioyl)indan-l-yllcarbamate :

A solution of tert-butyl N-[5-(trimethylsilylmethylcarbamoyl)indan-l-yl]carbamate (2.2 g, 6.1 mmol) in toluene (25 mL), was treated with lawessons reagent (2.8 g, 6.7 mmol), and heated at 120 C for 2 hours. The toluene was evaporated and the residue was treated with water (25 mL) and extracted with ethylacetate (25 mL). The combined organic layers were dried over sodium sulfate, concentrated, and purified by column chromatography (hexane/ethylacetate as eluent) to afford tert-butyl N-[5- (trimethylsilylmethylcarbamothioyl)indan-l -yl]carbamate (1.8 g). 'H-NMR (400 MHz, CDC13): 7.6 (IH, s), 7.53 (IH, brs), 7.45 (IH, d), 7.30 (IH, d), 5.2 (IH, brs), 4.7 (IH, brs), 3.5 (2H, d), 3.00 (IH, m), 2.8 (IH, m), 2.6 (IH, m), 1.8 (IH, m), 1.45 (s, 9H) 0.2 (s, 9H). LC-MS (methanol, ESI): m/z = 379 (M+H, retention time =2.27). Example 18: Preparation of tert-butyl N-[5-r3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4- dihydropyrrol-5-yllindan- 1 -yl ^" |carbamate:

A solution of tert-butyl N-[5-(trimethylsilylmethylcarbamothioyl)indan-l -yl]carbamate (1.2 g, 3.2 mmol) in dimethyl formanide (10 mL) at 0 C, was treated with potassium carbonate (0.9 g, 6.3 mmol) and methyl iodide (4.5 g, 32 mmol) added in three portions, and stirred for 3 hours. To the reaction mixture water (10 mL) was added, followed by extraction with ethylacetate (2 x 25mL). The combined organic layers were dried over sodium sulfate, concentrated to afford crude material. The crude material was diluted with tetrahydrofuran (20 mL), cooled at 0 C, treated with l ,3-dichloro-5-[l - (trifluoromethyl)vinyl]benzene and TBAB, and stirred for 20 hours. Tetrahydrofuran was removed under reduced pressure, diluted with water (25 mL), and extracted with ethylacetate (2 x 25mL). The combined organic layers were dried over sodium sulfate, concentrated and purified by column chromatography (hexane/ethyl acetate) gave tert-butyl N-[5-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4- dihydropyrrol-5-yl]indan-l -yl]carbamate (0.7 g). 'H-NMR (400 MHz, CDC13): 7.8 (2H, s), 7.7 (1H, m), 7.35 (2H, s), 7.25 (1H, d), 5.9 (1H, brs), 5.6 (1H, brs), 4.9 (1H, d), 4.4 (1H, d), 4.8 (1H, d), 3.40 (1H, d), 3.00 (1H, m), 2.90 (1H, m), 2.6 (1H, m), 2.00 (1H, m), 1.45 (s, 9H). LC-MS (methanol, ESI): m/z = 513 (M+H, retention time =2.50).

Example 19: General procedure for the preparation of N-[5-r3-(3,5-dichlorophenyl)-3-(trifluoromethyl)- 2.4-dihvdropyrrol-5-yl1indan-l -yl1amides: (a) R = Me. (b) R = Et. (c) R = cPr. (d) = CF ₃

A solution of tert-butyl N-[5-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydro pyrrol-5-yl]indan-l - yl]carbamate (1 mmol) in dichloromethane (5 mL), was treated with TFA ( 4 eq.), and stirred for 5 hours. The reaction mixture was concentrated under reduced pressure, diluted with dichloromethane (5 mL), and treated with triethylamine (5 eq.) and the appropriate carboxylic acid chloride (1.1 eq.) and stirred for 16 hours. The reaction mixture was concentrated and purified by column chromatography (hexane/ethyl acetate) to give:

(a) N- [5 - [3-(3 ,5 -dichlorophenyl)-3 -(trifluoromethyl)-2 ,4-dihydropyrrol-5 -yl] indan- 1 - yl]acetamide: 0.12 g, 1H-NMR (400 MHz, CDC13): 7.8 (1H, m), 7.7 (1H, m), 7.30 (1H, m), 7.20 (1H, m), 6.1 (1H, m), 5.5 (1H, m), 4.8 (1H, d), 4.4 (1H, d), 3.8 (1H, d), 3.45 (1H, d), 3.00 (1H, m), 2.90 (1H, m), 2.6 (1H, m), 2.00 (3H, s), 1.8 (1H, m). LC-MS (methanol, ESI): m z = 455 (M+H, retention time = 2.11).

(b) N- [5 - [3-(3 ,5 -dichlorophenyl)-3 -(trifluoromethyl)-2 ,4-dihydropyrrol-5 -yl] indan- 1 - yl]propanamide: 0.12 g, 1H-NMR (400 MHz, CDC13): 7.9 (1H, m), 7.8 (1H, m), 7.40 (2H, m), 7.30 (2H, m), 5.70 (1H, m), 5.50 (1H, m), 4.90 (1H, d), 4.50 (1H, d), 3.90 (1H, d), 3.60 (1H, d), 3.00 (1H, m), 2.90 (1H, m), 2.6 (1H, m), 2.3 (2H, d), 1.8 (1H, m). 1.2 (3H, t) LC-MS (methanol, ESI): m z = 469 (M+H, retention time = 2.17).

(c) N- [5 - [3-(3 ,5 -dichlorophenyl)-3 -(trifluoromethyl)-2 ,4-dihydropyrrol-5 -yl] indan- 1 - yl]cyclopropanecarboxamide: 70 mg, 1H-NMR (400 MHz, CDC13): 7.8 (1H, m), 7.77 (1H, m), 7.40 (2H, m), 7.30 (2H, m), 5.90 (1H, m), 5.50 (1H, m), 4.90 (1H, d), 4.45 (1H, d), 3.85 (1H, d), 3.50 (1H, d), 3.00 (1H, m), 2.90 (1H, m), 2.6 (1H, m), 1.8 (1H, m). 1.0 (2H, m), 0.8 (2H, m), LC-MS (methanol, ESI): m z = 481 (M+H, retention time = 2.22)

(d) N- [5 - [3-(3 ,5 -dichlorophenyl)-3 -(trifluoromethyl)-2 ,4-dihydropyrrol-5 -yl] indan- 1 -yl] - 2,2,2-trifluoro-acetamide: 120 mg, 1H-NMR (400 MHz, CDC13): 7.9 (1H, m), 7.8 (1H, m), 7.35 (2H, m), 7.25 (2H, m), 6.60 (1H, m), 5.50 (1H, m), 4.90 (1H, d), 4.50 (1H, d), 3.80 (1H, d), 3.50 (1H, d), 3.10 (1H, m), 3.00 (1H, m), 2.70 (1H, m), 2.00 (1H, m), LC- MS (methanol, ESI): m/z = 509 (M+H, retention time = 2.37)

Example 20: Preparation of 5-r3-r3,5-bis(trifluoromethyl phenyll-3-(trifluoromethyl pyrrolidin-l- yl ^" |indan- 1 -amine

To a solution of 3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrol idine (0.260 g, prepared as described in WO 2008/128711) and tert-butyl N-(5-bromoindan-l-yl)carbamate (0.231 g) in toluene (5.2 niL) stirred under argon were added tris(dibenzylideneacetone)dipalladium(0) (13.6 mg), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (22.1 mg) and sodium tert-butoxide (147 mg).

The mixture was heated in the microwave at 130°C for 15 min. The reaction was then diluted with ethylacetate and water then brine and then the mixture was extracted with ethyl acetate. The organic layers were combined and dried over magnesium sulphate, filtered then concentrated under reduced pressure to give a brown oil which was purified by chromatography on column (cyclohexane/EtOAc as solvent) to afford the desired product as a white foam (245 mg). 1H NMR (CDC13, 400MHz): d = 7.92 (s, 1 H), 7.86 (s, 2 H), 7.27 (m, 1 H), 6.47 - 6.58 (m, 2 H), 4.35 (m, 1 H), 4.05 - 4.23 (m, 1 H), 3.85 (m, 1 H), 3.60 (m, 1 H), 3.51 (m, 1 H), 2.90 - 3.03 (m, 2 H), 2.71 - 2.86 (m, 1 H), 2.55 - 2.66 (m, 1 H), 2.50 (dt, J=7.2, 4.3 Hz, 1 H), 1.83 - 2.13 (m, 2 H), 1.72 ppm (dd, J=12.5, 8.1 Hz, 1 H)

Example 21 : Preparation of N-[5-r3-r3,5-bis(trifluoromethyl)phenyll-3-(trifluoromethyl) pyrrolidin-l - yl ^" |indan- 1 -yl ^" |propanamide

To a solution of 5-[3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyr rolidin-l-yl]indan-l -amine (100 mg), in dichloromethane (3.0 mL) and triethylamine (0.088 mL) stirred at room temperature, was added propanoyl chloride (0.027 mL) and the solution was stirred for 3 hours. The reaction was then diluted with ethylacetate and water and then the mixture was extracted with ethyl acetate. The organic layers were combined and dried over magnesium sulphate, filtered then concentrated under reduced pressure to give a yellow solid which was purified by chromatography on column (cyclohexane/EtOAc as solvent) to afford the desired product as a beige solid (87 mg). 1H NMR (CDC13, 400MHz): d = 7.92 (s, 1 H), 7.86 (s, 2 H), 7.21 (d, J=8.1 Hz, 1 H), 6.45 - 6.58 (m, 2 H), 5.56 (d, J=8.1 Hz, 1 H), 5.37 - 5.49 (m, 1 H), 4.16 (d, J=9.2 Hz, 1 H), 3.85 (d, J=10.6 Hz, 1 H), 3.46 - 3.60 (m, 2 H), 2.91 - 3.04 (m, 2 H), 2.78 - 2.91 (m, 1 H), 2.52 - 2.70 (m, 2 H), 2.24 (q, J=7.7 Hz, 2 H), 1.76 - 1.87 (m, 1 H), 1.13 - 1.24 ppm (m, 3 H)

Example 22

The synthesis was as described in WO2009/112275.

Melting point: 103-105 °C

LC-MS: retention time = 1.95, (M ⁺ H) ⁺ = 471 (measured) (Method B)

To a solution of l-[4-(bromomethyl)-3-chloro-phenyl]ethanone (1 g, 4.04mmol) in N,N- dimethylformamide was added (1, 3-dioxoisoindolin-2-yl) potassium (823 mg, 4.44mmol). The reaction mixture was refluxed for 5-6 hours, while being monitored by Thin Layer Chromatography (TLC). The reaction mixture was then diluted with water (20 niL), extracted with ethylacetate (3 x 30 mL). The combined organic layers were dried over sodium sulphate then concentrated under reduced pressure. The residue obtained was purified by column chromatography to afford the desired product 2-[(4-acetyl-2- chloro-phenyl)methyl]isoindoline-l,3-dione (870 mg)

ESI-MS: m/z = 313.9 [M+H] ⁺ .

lH NMR (400 MHz, CDC1 ₃ ): δ 7.85-7.90(m, 1H), 7.80-7.85 (m, 1H), 7.68-7.71 (m, 4H), 7.21-7.23 (m, 1H 4.96 (s, 2H), 2.50 (s, 3H)

To a solution of 2-[(4-acetyl-2-chloro-phenyl)methyl]isoindoline-l,3-dione (670 mg, 2.13 mmol) and 1- [3-bromo-5-(trifluoromethyl)phenyl]-2,2,2-trifluoro-ethanone (685 mg, 2.13 mmol) in acetonitrile (10 mL) was added potassium carbonate (150 mg, 1.06 mmol). The reaction mixture was refluxed at 120°C overnight. It was then diluted with water (10 mL) and extracted with ethylacetate (3 x 30 mL). The combined organic layers were dried over sodium sulphate then concentrated under reduced pressure. The residue obtained was purified by column chromatography to afford the desired product 2-[[4-[(Z)-3-[3- bromo-5-(trifluoromethyl)phenyl]-4,4,4-trifluoro-but-2-enoyl ]-2-chloro-phenyl]methyl]isoindoline- dione (550 mg)

ESI-MS: m/z = 614.76 [M-H] ⁺ .

lH NMR (400 MHz, CDC1 ₃ ): δ 7.87-7.93 (m, 3H), 7.73-7.83 (m, 4H), 7.52-7.65 (m, 2H), 7.38-7.42 (m, 1H 7.27-7.31 (m, 1H), 5.00-5.02 (d, 2H)

To a solution of 2-[[4-[(Z)-3-[3-bromo-5-(trifluoromethyl)phenyl]-4,4,4-trifl uoro-but-2-enoyl]-2-chloro- phenyl]methyl]isoindoline-l,3-dione (500 mg, 0.813 mmol) in isopropyl alcohol (5 mL) was added a solution of sodium hydroxide (98 mg, 2.44 mmol) in water (2 mL) followed by 50% hydroxylamine solution (322 mg, 4.88 mmol). The reaction mixture was refluxed for 6-7 hours, while being monitored by TLC. The reaction mixture was concentrated under reduced pressure, diluted with water (10 mL) and extracted with ethylacetate (3 x 30 mL). The combined organic layers were dried over sodium sulphate then concentrated under reduced pressure. The residue obtained was purified by column chromatography to afford the desired product [4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl )-4H-isoxazol- 3-yl]-2-chloro-phenyl]methanamine (170 mg)

ESI-MS: m/z = 500.84 M+H] ⁺ .

To a solution of [4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl )-4H-isoxazol-3-yl]-2- chloro-phenyl]methanamine (100 mg, 0.2 mmol) in dichloromethane (4 mL) at 0°C was added triethylamine (0.05 mL, 0.3 mmol), followed by butyryl chloride (32 mg, 0.3 mmol). The reaction mixture was stirred at room temperature for lhour. It was then diluted with water (5 mL) and extracted with dichloromethane (3 x 20 mL). The combined organic layers were dried over sodium sulphate then concentrated under reduced pressure. The residue obtained was purified by column chromatography to afford the desired product N-[[4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-5-(trifluoromet hyl)-4H- isoxazol-3-yl]-2-chloro-phenyl]methyl]butanamide (50 mg)

ESI-MS: m/z = 570.88 [M+H] ⁺ . ^l H NMR (400 MHz, CDC1 ₃ ): δ 7.88 (m, IH), 7.77 (m, IH), 7.72 (m, IH), 7.62-7.63 (m, IH), 7.38-7.46 (m, 2H), 5.89 (br s, IH), 4.46-4.48 (d, 2H), 4.01-4.05 (d, IH), 3.60-3.64 (d, IH), 2.12-2.15 (m, 2H), 1.57- 1.65 (m, 2H), 0.85-0.89 (m, 3H) Biological Examples Table A

1 2 3 2 5 8

Tables A provides compounds of formula la wherein B , B , B , R , R , and R are as described below

B1-B2-B3 R2 R5 R8

Al C=N-0 3,5- dichloropheny 1 chloro methylsulfanylmethyl

A2 C=N-0 3,5- dichloropheny 1 chloro isopropyl

A3 C=N-0 3,5- dichloropheny 1 chloro ethyl

A4 N-CH ₂ -CH ₂ 3,5- dichloropheny 1 methyl methyl

A5 C=N-CH ₂ 3,5- dichloropheny 1 bromo methyl

A6 C=N-CH ₂ 3,5- dichloropheny 1 bromo ethyl

A7 C=N-CH ₂ 3,5- dichloropheny 1 bromo cyclopropyl

A8 C=N-0 3,5- dichloropheny 1 methyl methyl

A9 C=N-0 3,5- dichloropheny 1 methyl isopropyl

A10 C=N-0 3,5- dichloropheny 1 methyl methylsulfanylmethyl

Al l C=N-0 3,5- dichloropheny 1 methyl tetrahydrofuran-2-yl

A12 C=N-0 3,5- dichloropheny 1 hydrogen isopropyl

A13 C=N-0 3,5- dichloropheny 1 hydrogen methylsulfanylmethyl

A14 C=N-0 3 , 5 -dichloropheny 1 chloro 1 -bromopropan- 1 -yl

A15 C=N-0 3,5- dichloropheny 1 chloro tetrahydrofuran-2-yl

A16 C=N-0 3,5- dichloropheny 1 hydrogen ethyl

A17 C=N-0 3,5- dichloropheny 1 hydrogen 1 -bromopropan- 1 -yl

A18 C=N-0 3,5- dichloropheny 1 hydrogen tetrahydrofuran-2-yl

A19 C=N-0 3,5- dichloropheny 1 chloro methylsulfonylmethyl

A20 C=N-0 3,5- dichloropheny 1 chloro methylsulfinylmethyl

A21 C=N-0 3-bromo-5- chloro n-propyl trifluorophenyl

Table B

Tables B provides compounds of formula lb* wherein B ¹ , B ² , B ³ , R ² and R ⁸ are as described below

Table C

Tables C provides compounds of formula Ic wherein B ¹ , B ² , B ³ , R ² and R ⁵ are as described below

B1-B2-B3 R2 R5

CI N-CH2-CH2 3,5- dichloropheny 1 cyano

C2 C=N-CH ₂ 3,4,5-trichlorophenyl cyano

C3 C=N-0 3,5-dichloro-4-fluorophenyl cyano

C4 C=N-0 3,5- dichloropheny 1 cyano

C5 C=N-0 3,5- dichloropheny 1 methyl

C6 C=N-0 3,4,5-trichlorophenyl cyano

C7 C=N-0 3,5- dichloropheny 1 cyano Table D

Tables D provides compounds of formula Id wherein B 1,B2,B3,R2,R5,Z1,Z2 and Z 3 are as described below

Table E

Tables E provides compounds of formula Ie wherein B ¹ , B ² , B ³ , R ² , and R ⁹ are as described below

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 is 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.

Diabrotica balteata (Banded Cucumber Beetle)

Treated corn seeds are sown in a 350 ml pot filled with soil. Two weeks after sowing phytotoxicity (lack of shoot - missing emergence) in comparison to the control is estimated and expressed in percentage. Furthermore, corn seedlings are infested with 3 ^rd stage larvae of Diabrotica balteata. After an incubation period of 6 days survived larvae are counted and larval growth is assessed. Larval growth indicates the the number of larvae with size differences between the larvae in the control and treatments, expressed in percentage.

C2 0.3 44

C3 1 83

C4 1 100

Dl 1 100

D2 1 100

El 0.3 83

E7 0.3 60

Agriotes sp. (Wireworms)

Treated corn seeds are sown in a 350 ml pot filled with soil. One week after sowing phytotoxicity (lack of shoot - missing emergence) in comparison to the control is estimated and expressed in percentage.

5 Furthermore, corn seedlings are infested with all larval stages of Agriotes sp. (wireworm) After an incubation period of 14 days healthy and affected larvae (intoxicated, moribund, dead) are counted.

Diabrotica balteata (Corn rootworm)

A 24-well microtiter plate (MTP) with artificial diet is treated with test solutions at an application rate of 10 200 ppm (concentration in well 18 ppm) by pipetting. After drying, the MTP's are infested with L2 larvae (6-10 per well). After an incubation period of 5 days, samples are checked for larval mortality.

The following compounds were tested and gave at least 80% control of Diabrotica balteata at 200ppm: A2*, A3*, A4*, A5*, A6*, A7*, A8*, A9*, A10* Al l, A12, A13* A14* A15, A16* A17* A18, A19* A20*, Bl * B2*, B3*, B4*, CI, C2*, C3*, C4*, C5*, Dl *, D2*, D4, D6*, D7*, D8*, D9*, El *, 15 E2*, E3*, E4*, E5*, E6*, E7*, E8*. D5 gave lower control at 200ppm. No activity was found for D10 and Dl l .

* = gave at least 80% control at 50ppm or less

Diabrotica balteata (Corn rootworm)

20 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

25 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.

Termites

Washed sand is treated with the experimental compound in a volatile solvent, so as to deliver the desired concentration w/w in the solvent free sand. Once the solvent has evaporated, the sand is thoroughly mixed and made up with deionised water to 3% w/w moisture content. The treated sand is packed into a glass tube (internal diameter of 13.5 mm, length 120 mm) so that a 5 cm column of treated sand is formed in the tube, leaving ca. 1 cm free from one open end. A small section of filter paper is placed on the soil surface nearest the tube end, and sealed with a rubber bung or with aluminium foil. A ca. 2 cm bung of 7% agar is cut and pushed into the open end of the tube until it is in contact with the treated sand. Another section of filter paper is placed on the agar bung and ca. 40 worker termites, with not more than one soldier, are placed on the filter paper. The open end of the tube is then sealed with a rubber bung or aluminium foil. The so prepared tubes are held under similar conditions to their culture colony. The mortality of the termites, any unusual behaviour or symptomology, and the distance they have tunnelled into the treated soil, is recorded daily for up to 21 days.

Comparative Example

Compounds are tested according to the above method. The results show that the compounds of the invention are significantly more active against Diabrotica balteata (Corn rootworm) than structurally similar compounds, particularly at low rates of application.

Comparative Table 1

Compound of the invention Reference compound

Compound Test Application rate Control /

/ ppm %

Compound of the invention Diabrotica balteata (Corn 12.5 100

rootworm)

3 100

Reference compound Diabrotica balteata (Corn 12.5 65 rootworm) 3 nt nt = not tested

The compound of the invention and reference compound are compounds 3-6 and 3-643 respectively from WO 2009/1 12275.

Comparative Table 2

The compound of the invention and reference compound are compounds 42 and 9 respectively from WO 2007/075459.