WO2014019951A1

WO2014019951A1 - Methods of controlling insects

Info

Publication number: WO2014019951A1
Application number: PCT/EP2013/065787
Authority: WO
Inventors: Myriem El Qacemi; Jérôme Yves CASSAYRE
Original assignee: Syngenta Participations AG
Current assignee: Syngenta Participations AG
Priority date: 2012-08-03
Filing date: 2013-07-26
Publication date: 2014-02-06
Anticipated expiration: 2015-02-03
Also published as: US20150189883A1; PH12015500222A1; CN104520287A; BR112015002375A2

Abstract

The present invention provides methods comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof,compounds including those of formula (I) wherein cycle A is A1 a or A2 a formula (II) Wherein A¹, A², A³ and A⁴ are independently C-H, or nitrogen and wherein #1 indicates the bond to X and #2 indicates the bond to cycle B; cycle B is B1 formula (III) wherein #1 indicates the bond to cycle A, #2 indicates the bond to R⁷ and #3 indicates the bond to cycle C; cycle C is phenyl; R⁵ is chloro, bromo, CF₃ or methyl; R⁷ is chlorodifluoromethyl or trifluoromethyl; each R⁸ is independently bromo, chloro, fluoro or trifluoromethyl; p is 1, 2 or 3; and X is selected from formula (P1 to P9). The methods are preferably for controlling and/or preventing infestation of stemborer, leaffolder, hoppers, Gall midge, whorl maggot, Rice bugs, and Black bugs.

Description

METHODS OF CONTROLLING INSECTS

The present invention relates to a method of controlling insects, in particular insects that infest rice.

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

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

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

It has now surprisingly been found that particular insecticides from this new class of gamma- aminobutyric acid (GABA)-gated chloride channel antagonists (disclosed in e.g. WO2009/080250, WO2010/020522, WO2010/149506, WO2011/101229 and WO2012/045700) are highly effective at controlling certain pests in rice. The compounds of interest include a thietane amide derivative in which the thietane carbon ring members are unsubstituted.

These compounds therefore represent an important new solution for safeguarding crops of useful plants, particularly rice crops, from insects that infest rice crops, particularly where the insects are resistant to current methods.

In a first aspect the invention provides a method comprising applying to a crop of rice plants, the locus th mpound of formula I

wherein

cycle A is Ala or A2a

A1 a A2a

wherein A¹, A², A³ and A⁴ are independently C-H, or nitrogen and wherein #1 indicates the bond to X and #2 indicates the bond to cycle B;

cycle B is Bl

B1

wherein #1 indicates the bond to cycle A, #2 indicates the bond to R⁷ and #3 indicates the bond to cycle C;

cycle C is phenyl;

R⁵ is chloro, bromo, CF₃ or methyl;

R⁷ is chlorodifluoromethyl or trifluoromethyl;

each R⁸ is independently bromo, chloro, fluoro or trifluoromethyl;

p is 1, 2 or 3; and

and X is selected from PI to P9

P2 P3 P4

P5 P6 P7 P8 P9 The method may be for controlling and/or preventing insects selected from the group consisting of stemborer, leaffolder, hoppers, Gall midge, whorl maggot, Rice bugs, and Black bugs.

In one embodiment the invention provides a method of controlling and/or preventing stemborer in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I. In one embodiment the invention provides use of a compound of formula I for controlling and/or preventing stemborer, particularly in rice. The stemborer may be resistant to other insecticides. Examples of stemborers include Chilo sp, Chilo suppressalis, Chilo polychrysus, Chilo auricilius, Scirpophaga spp., Scirpophaga incertulas, Scirpophaga innotata, Scirpophaga nivella Sesamia sp, Sesamia inferens. 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 stemborer, preferably in rice, comprising at least one step of referring to, submitting or relying on biological data showing that said active ingredient reduces insect pressure.

In one embodiment the invention provides a method of controlling and/or preventing leaffolder in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I. In one embodiment the invention provides use of a compound of formula I for controlling and/or preventing leaffolder, particularly in rice. The leaffolder may be resistant to other insecticides. Examples of leaffolders include Cnaphalocrocis spp., Cnaphalocrocis medinalis, Marasmia spp., Marasmia patnalis, Marasmia exigua. 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 leaffolder, preferably in rice, comprising at least one step of referring to, submitting or relying on biological data showing that said active ingredient reduces insect pressure.

In one embodiment the invention provides a method of controlling and/or preventing, hoppers in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I. In one embodiment the invention provides use of a compound of formula for controlling and/or preventing hoppers, particularly in rice. The hoppers may be resistant to other insecticides. Examples of Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus, Nephotettix malayanus, Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera. 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 hoppers, preferably in rice, comprising at least one step of referring to, submitting or relying on biological data showing that said active ingredient reduces insect pressure.

In one embodiment the invention provides a method of controlling and/or preventing Gall midge in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I. In one embodiment the invention provides use of a compound of formula for controlling and/or preventing Gall midge, particularly in rice. The Gall midge may be resistant to other insecticides. Examples of Gall midge include Orseolia sp, Orseolia oryzae. 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 Gall midge, preferably in rice, comprising at least one step of referring to, submitting or relying on biological data showing that said active ingredient reduces insect pressure.

In one embodiment the invention provides a method of controlling and/or preventing whorl maggot in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I. In one embodiment the invention provides use of a compound of formula for controlling and/or preventing whorl maggot, particularly in rice. The whorl maggot may be resistant to other insecticides. Examples of whorl maggots include Hydrellia sp, Hydrellia philippina. 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 whorl maggots, preferably in rice, comprising at least one step of referring to, submitting or relying on biological data showing that said active ingredient reduces insect pressure.

In one embodiment the invention provides a method of controlling and/or preventing Rice bugs in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I. In one embodiment the invention provides use of a compound of formula for controlling and/or preventing Rice bugs, particularly in rice. The Rice bugs may be resistant to other insecticides. Examples of rice bugs include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta. 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 Rice bugs, preferably in rice, comprising at least one step of referring to, submitting or relying on biological data showing that said active ingredient reduces insect pressure.

In one embodiment the invention provides a method of controlling and/or preventing Black bugs in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I. In one embodiment the invention provides use of a compound of formula for controlling and/or preventing Black bugs, particularly in rice. The Black bugs may be resistant to other insecticides. Examples of Black bugs include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula. 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 Black bugs, preferably in rice, comprising at least one step of referring to, submitting or relying on biological data showing that said active ingredient reduces insect pressure.

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

Preferred values of cycle A, cycle B, cycle C, X, p, A¹, A², A³, A⁴, R⁵, R⁷ and R⁸ in compounds of formula I are, in any combination, as set out below.

Preferably cycle A is Al a.

cycle C is cycle CI

C1

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

Preferably A¹ is C-H or C-R⁵, most preferably A¹ is C-H.

Preferably A² is C-H or C-R⁵, most preferably A² is C-H.

Preferably A³ is C-H or C-R⁵, most preferably A³ is C-H.

Preferably A⁴ is C-H or C-R⁵, most preferably A⁴ is C-H.

Preferably no more than one of A¹ and A² is nitrogen. Preferably no more than one of A³ and A⁴ is nitrogen. Preferably A¹ and A² are both C-H. Preferably both A³ and A⁴ are C-H

Preferably R⁵ is methyl or chloro, most preferably methyl.

Preferably R⁷ is trifiuoromethyl.

Preferably each R⁸ is independently fluoro, bromo or chloro.

Preferably p is 2 or 3, most preferably 2.

Preferably X is P2, P3 or P4, more preferably P3 or P4.

In one group of compounds cycle A is Ala.

In one group of compounds cycle A is Ala, R⁷ is trifiuoromethyl and X is P2, P3 or P4.

In one group of compounds cycle A is Ala, R⁷ is trifiuoromethyl and X is P2, P3 or P4 and cycle C is selected from 3,5-dichloro-4-fluorophenyl-, 3,4,5-trichlorophenyl-, 3,5-bis(trifluoromethyl)phenyl- and 3,5-dichloro-phenyl.

In one group of compounds X is P2, P3, P4, P5, P7 or P9.

In one group of compounds X is P3, P4, P7 or P9.

In one group of compounds X is P3 or P9.

In one group of compounds X is P3 or P4.

In one group of compounds X is P3.

In one group of compounds X is P5, P7 or P9.

In one group of compounds X is P7 or P9.

In one group of compounds X is P9.

In one group of compounds cycle C is 3,4,5-trichlorophenyl- or 3,5-dichloro-4-fluorophenyl-.

In one group of compounds cycle C is 3,4,5-trichlorophenyl-.

In one group of compounds cycle C is 3,5-dichloro-4-fluorophenyl-.

In one group of compounds cycle C is 3,5-dichloro-phenyl.

In one group of compounds cycle C is 3,4,5-trichlorophenyl- or 3,5-dichloro-4-fluorophenyl- and X is P2, P3, P4, P5, P7 or P9. In one group of compounds cycle C is 3,4,5-trichlorophenyl- or 3,5-dichloro-4-fluorophenyl- and X is P3, P4, P7 or P9.

In one group of compounds cycle C is 3,4,5-trichlorophenyl- or 3,5-dichloro-4-fluorophenyl- and X is P3 or P9.

In one group of compounds cycle C is 3,4,5-trichlorophenyl- or 3,5-dichloro-4-fluorophenyl- and

X is P3.

X is P9. The following tables illustrate specific compounds of the invention:

Table 1

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

Table 2

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

Table 3

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

Table 4

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

Table 5

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

Table 6

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

Table 7

Table 7 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-CH, Cycle B is B 1 , and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 8

Table 8 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are N-CH, Cycle B is B 1 , and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table 9

Table 9 provides 338 compounds of Formula I wherein cycle A is cycle A2a, A3 and A4 are CH-N, Cycle B is B 1 , and R7 is trifluoromethyl, and cycle C and X are as defined in Table P.

Table P

Cycle C X Stereochemistry

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

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

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

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

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

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

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

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

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

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

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

3 -trifluoromethyl-phenyl- PI _j**

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

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

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

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

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

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

3,4,5-trifluorc>-phenyl- P2 _j**

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

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

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

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

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

3 -trifluoromethyl-phenyl- P2 _j**

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

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

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

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

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

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

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

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

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

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

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

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

3 -trifluoromethyl-phenyl- P3 _j**

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

3 -trifluoromethyl-phenyl- P4 _j**

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

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

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

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

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

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

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

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

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

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

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

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

3 -trifluoromethyl-phenyl- P5 _j**

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

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

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

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

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

3 ,5 -dichloro-4-bromo -phenyl- P6 98 3,4,5-trifluoro-phenyl- P6 _j**

99 3-chloro-5-bromo-phenyl- P6 _j**

100 3-chloro-5-trifluoromethyl-phenyl- P6 _j**

101 3-chloro-4-chloro-5-trifluoromethyl-phenyl- P6 _j**

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

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

104 3 -trifluoromethyl-phenyl- P6 _j**

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

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

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

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

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

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

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

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

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

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

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

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

117 3 -trifluoromethyl-phenyl- P7 _j**

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

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

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

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

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

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

124 3,4,5-trifluoro-phenyl- P8 _j**

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

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

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

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

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

130 3 -trifluoromethyl-phenyl- P8 _j**

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

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

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

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

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

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

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

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

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

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

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

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

143 3 -trifluoromethyl-phenyl- P9 144 3,5-dichloro-phenyl- P9 (cis) _j**

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

169 3 -trifluoromethyl-phenyl- P9 (trans)

170 3,5-dichloro-phenyl- PI

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

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

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

174 3,4-dichloro-phenyl- PI

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

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

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

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

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

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

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

182 3 -trifluoromethyl-phenyl- PI

183 3,5-dichloro-phenyl- P2

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

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

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

187 3,4-dichloro-phenyl- P2

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

189 3,4,5-trifluoro-phenyl- P2 190 3-chloro-5-bromo-phenyl- P2

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

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

193 3 ,5 -di-trifluoromethyl-phenyl- P2

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

195 3 -trifluoromethyl-phenyl- P2

196 3,5-dichloro-phenyl- P3

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

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

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

200 3,4-dichloro-phenyl- P3

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

202 3,4,5 rifluoro-phenyl- P3

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

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

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

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

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

208 3 -trifluoromethyl-phenyl- P3

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

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

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

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

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

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

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

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

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

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

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

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

221 3 -trifluoromethyl-phenyl- P3 (cis)

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

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

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

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

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

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

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

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

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

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

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

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

234 3 -trifluoromethyl-phenyl- P3 (trans)

235 3,5-dichloro-phenyl- P4 236 3,4,5 -trichloro-phenyl- P4

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

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

239 3,4-dichloro-phenyl- P4

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

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

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

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

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

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

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

247 3 -trifluoromethyl-phenyl- P4

248 3 ,5 -dichloro-phenyl- P5

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

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

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

252 3,4-dichloro-phenyl- P5

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

254 3,4,5-trifluoro-phenyl- P5

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

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

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

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

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

260 3 -trifluoromethyl-phenyl- P5

261 3,5-dichloro-phenyl- P6

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

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

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

265 3,4-dichloro-phenyl- P6

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

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

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

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

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

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

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

273 3 -trifluoromethyl-phenyl- P6

274 3,5-dichloro-phenyl- P7

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

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

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

278 3,4-dichloro-phenyl- P7

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

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

281 3-chloro-5-bromo-phenyl- P7 282 3-chloro-5-trifluoromethyl-phenyl- P7

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

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

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

286 3 -trifluoromethyl-phenyl- P7

287 3,5-dichloro-phenyl- P8

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

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

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

291 3,4-dichloro-phenyl- P8

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

293 3,4,5 rifluoro-phenyl- P8

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

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

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

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

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

299 3 -trifluoromethyl-phenyl- P8

300 3,5-dichloro-phenyl- P9

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

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

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

304 3,4-dichloro-phenyl- P9

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

306 3,4,5-trifluoro-phenyl- P9

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

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

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

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

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

312 3 -trifluoromethyl-phenyl- P9

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

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

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

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

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

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

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

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

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

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

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

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

325 3 -trifluoromethyl-phenyl- P9 (cis)

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

327 3,4,5 -trichloro-phenyl- P9 (trans) 328 3,5-dichloro-4-fluoro-phenyl- P9 (trans)

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

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

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

332 3,4,5 rifluoro-phenyl- P9 (trans)

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

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

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

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

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

338 3 -trifluoromethyl-phenyl- P9 (trans)

I* * refers to compounds of formula I* * .

In one embodiment the compound of formula I is a compound selected from Tables 1 to 9.

Compounds of formula I include at least one chiral centre and may exist as compounds of formula I* or compounds of formula I**

(IB^*) (IB^**)

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

Where possible, each compound disclosed in Tables 1 to 9 represents a specific disclosure of the isomer according to the compound of formula I* and the isomer according to the compound of formula I**, as well as mixtures enriched for the compound according to the compound of formula I*, and mixtures enriched for the compound according to the compound of formula I**, as described above.

In one embodiment the invention provides a compound selected from Tables 1 to 9 for use against rice pests.

In one embodiment the invention provides a compound selected from Tables 1 to 9 for use against stemborer, particularly in rice.

Examples of stemborers include Chilo sp, Chilo suppressalis, Chilo polychrysus, Chilo auricilius, Scirpophaga spp., Scirpophaga incertulas, Scirpophaga innotata, Scirpophaga nivella

Sesamia sp, Sesamia inferens.

In one embodiment the invention provides a compound selected from Tables 1 to 9 for use against leaffolder, particularly in rice .

Examples of leaffolders include Cnaphalocrocis spp., Cnaphalocrocis medinalis, Marasmia spp., Marasmia patnalis, Marasmia exigua.

In one embodiment the invention provides a compound selected from Tables 1 to 9 for use against hoppers, particularly in rice.

Examples of Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus,

Nephotettix malayanus, Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera.

In one embodiment the invention provides a compound selected from Tables 1 to 9 for use against gallmidge, particularly in rice.

Examples of Gall midge include Orseolia sp, Orseolia oryzae.

In one embodiment the invention provides a compound selected from Tables 1 to 9 for use against whorl maggot, particularly in rice.

Examples of whorl maggots include Hydrellia sp, Hydrellia philippina.

In one embodiment the invention provides a compound selected from Tables 1 to 9 for use against Rice bugs, particularly in rice.

Examples of rice bugs include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis,

Leptocorisa acuta.

In one embodiment the invention provides a compound selected from Tables 1 to 9 for use against Black bugs, particularly in rice.

Examples of Black bugs include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula.

The compounds of the invention may be prepared as described in WO2010/149506, which is incorporated by reference. In a further aspect the present invention provides a method comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula A

wherein

G¹ is oxygen;

R¹ is hydrogen;

2 is group P

L is a bond, methylene or ethylene;

one of A¹ and A² is S, SO or S0₂ and the other is -C(R⁴)R⁴-;

R³ is hydrogen;

each R⁴ is independently hydrogen;

Y¹, Y² and Y³ are independently CH or nitrogen;

wherein no more than two of Y¹, Y² and Y³ are nitrogen and wherein Y² and Y³ are not both nitrogen; R⁵ is bromo, chloro, fluoro;

X² is C-X⁶ or nitrogen;

Χ', Χ³ and X⁶ are independently hydrogen, halogen or trihalomethyl, wherein at least two of X¹, X³ and X⁶ are not hydrogen;

X⁴ is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.

Preferred values of R², R⁵, Y¹, Y², Y³, X¹, X², X³, X⁴ and X⁶ for compounds of formula A are, in any combination, as set out below.

Preferably R² is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l-dioxo-thietan-3-yl-, thietan-3-ylmethyl-, 1- oxo-thietan-3 -ylmethyl-, 1 , 1 -dioxo-thietan-3 -ylmethyl-, thietan-2-ylmethyl-, ( 1 -oxothietan-2-yl)methyl-, (l,l-dioxothietan-2-yl)methyl-, 2-(thietan-3-yl)ethanyl, 2-(l,l-dioxothietan-3-yl)ethanyl, or 2-(l - oxothietan-3-yl)ethanyl, more preferably R² is 2-(thietan-3-yl)ethanyl, 2-(l,l-dioxothietan-3-yl)ethanyl, 2-( 1 -oxothietan-3 -yl)ethanyl, thietan-3 -ylmethyl-, 1 -oxo-thietan-3 -ylmethyl-, 1 , 1 -dioxo-thietan-3 - ylmethyl-, thietan-3 -yl-, l-oxo-thietan-3-yl-, l,l -dioxo-thietan-3-yl-. More preferably R² is thietan-3 -yl-, l-oxo-thietan-3-yl-, l,l-dioxo-thietan-3-yl-, thietan-3-ylmethyl-, l-oxo-thietan-3-ylmethyl-, or 1,1-dioxo- thietan-3-ylmethyl-, most preferably thietan-3-yl-, l-oxo-thietan-3-yl-, or l,l-dioxo-thietan-3-yl-.

Preferably Y¹ is CH, Y² is CH, Y³ is CH, or Y¹ is N, Y² is CH, Y³ is CH, or Y¹ is N, Y² is N, Y³ is CH, orY¹ is CH, Y² is N, Y³ is CH, orY¹ is CH, Y² is CH, Y³ is N. More preferably Y¹ is CH, Y² is CH, Y³ is CH.

Preferably X 1 is chloro, X2 is CH, X 3 is chloro, or X 1 is chloro, X 2 is C-F, X 3 is hydrogen, or X 1 is fluoro, X 2 is C-Cl, X 3 is hydrogen, or X 1 is chloro, X 2 is C-Cl, X 3 is hydrogen, or X 1 is chloro, X 2 is C-

Br, X 3 is chloro, or X 1 is chloro, X2 is C-F, X3 is chloro, or X 1 is chloro, X2 is C-Cl, X3 is chloro, or X 1 is chloro, X 2 is C-I, X3 is chloro, or X 1 is fluoro, X 2 is C-F, X3 is fluoro, orX 1 is chloro, X 2 is CH, X3 is bromo, or X 1 is chloro, X 2 is CH, X 3 is fluoro, orX 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, or X 1 is chloro, X 2 is C-Cl, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X² is C-Cl, X³ is trifluoromethyl, or X¹ is trifluoromethyl, X² is CH, X³ is hydrogen, or

X 1 is chloro, X 2 is N, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl. Preferably X 1 is chloro, X² is CH, X³ is chloro, or X¹ is chloro, X² is C-Cl, X³ is chloro, or X¹ is chloro, X² is C-F, X³ is chloro, or X¹ is trifluoromethyl, X² is CH, X³ is trifluoromethyl. Most preferably X¹ is chloro, X² is CH, X³ is chloro.

Preferably X⁴ is trifluoromethyl.

In one embodiment the invention provides compounds of formula A wherein R⁵ is chloro and G¹, Pv¹, R², Y¹, Y², Y³, X¹, X², X³ and X⁴ are as defined for the compound of formula A.

In one embodiment the invention provides compounds of formula A wherein R⁵ is bromo and G¹,

R¹, R², Y¹, Y², Y³, X¹, X², X³ and X⁴ are as defined for the compound of formula A.

In one embodiment the invention provides compounds of formula A wherein R⁵ is fluoro and G¹, R¹, R², Y¹, Y², Y³, X¹, X², X³ and X⁴ are as defined for the compound of formula A.

In one embodiment the invention provides compounds of formula A wherein

G¹ is oxygen;

R¹ is hydrogen;

R² is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l-dioxo-thietan-3-yl-, thietan-3-ylmethyl-, 1-oxo- thietan-3-ylmethyl-, or l,l-dioxo-thietan-3-ylmethyl-;

Y¹ is CH, Y² is CH, Y³ is CH;

R⁵ is bromo, chloro, fluoro;

X¹ is chloro, X² is CH, X³ is chloro, or X¹ is chloro, X² is C-Cl, X³ is chloro, or X¹ is chloro, X² is C-F, X³ is chloro, orX¹ is trifluoromethyl, X² is CH, X³ is trifluoromethyl; and

X⁴ is trifluoromethyl.

In one embodiment the invention provides compounds of formula Awherein

G¹ is oxygen;

R¹ is hydrogen;

R² is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l-dioxo-thietan-3-yl-; Y¹ is CH, Y² is CH, Y³ is CH;

R⁵ is chloro;

X¹ is chloro, X² is CH, X³ is chloro, X¹ is chloro, X² is C-Cl, X³ is chloro, X¹ is chloro, X² is C-F, X³ is chloro, or X¹ is trifluoromethyl, X² is CH, X³ is trifluoromethyl; and

X⁴ is trifluoromethyl.

The compounds in the Tables below illustrates compounds of the invention

Table Px

Stereochemistry at

X4 R5 R2 isoxazoline

P.l trifluoromethyl bromo 1 , 1 -dioxo-thietan-3 -yl- S

P.2 trifluoromethyl chloro 1 , 1 -dioxo-thietan-3 -yl- S

P.3 trifluoromethyl fluoro 1 , 1 -dioxo-thietan-3 -yl- s

P.4 trifluoromethyl bromo 1 , 1 -dioxo-thietan-3 -ylmethyl- s

P.5 trifluoromethyl chloro 1 , 1 -dioxo-thietan-3 -ylmethyl- s

P.6 trifluoromethyl fluoro 1 , 1 -dioxo-thietan-3 -ylmethyl- s

P.7 trifluoromethyl bromo cis-l-oxo-thietan-3-yl- s

P.8 trifluoromethyl chloro cis-l-oxo-thietan-3-yl- s

P.9 trifluoromethyl fluoro cis-l-oxo-thietan-3-yl- s

P.10 trifluoromethyl bromo cis-l-oxo-thietan-3-ylmethyl- s

P.l l trifluoromethyl chloro cis-l-oxo-thietan-3-ylmethyl- s

P.12 trifluoromethyl fluoro cis-l-oxo-thietan-3-ylmethyl- s

P.13 trifluoromethyl bromo thietan-3-yl- s

P.14 trifluoromethyl chloro thietan-3-yl- s

P.15 trifluoromethyl fluoro thietan-3-yl- s

P.16 trifluoromethyl bromo thietan-3 -ylmethyl- s

P.17 trifluoromethyl chloro thietan-3 -ylmethyl- s

P.18 trifluoromethyl fluoro thietan-3 -ylmethyl- s

P.19 trifluoromethyl bromo 1 , 1 -dioxo-thietan-3 -yl-

P.20 trifluoromethyl chloro 1 , 1 -dioxo-thietan-3 -yl-

P.21 trifluoromethyl fluoro 1 , 1 -dioxo-thietan-3 -yl-

P.22 trifluoromethyl bromo 1 , 1 -dioxo-thietan-3 -ylmethyl-

P.23 trifluoromethyl chloro 1 , 1 -dioxo-thietan-3 -ylmethyl-

P.24 trifluoromethyl fluoro 1 , 1 -dioxo-thietan-3 -ylmethyl-

P.25 trifluoromethyl bromo cis-l-oxo-thietan-3-yl-

P.26 trifluoromethyl chloro cis-l-oxo-thietan-3-yl-

P.27 trifluoromethyl fluoro cis-l-oxo-thietan-3-yl-

P.28 trifluoromethyl bromo cis-l-oxo-thietan-3-ylmethyl-

P.29 trifluoromethyl chloro cis-l-oxo-thietan-3-ylmethyl-

P.30 trifluoromethyl fluoro cis-l-oxo-thietan-3-ylmethyl-

P.31 trifluoromethyl bromo thietan-3-yl-

P.32 trifluoromethyl chloro thietan-3-yl-

P.33 trifluoromethyl fluoro thietan-3-yl-

P.34 trifluoromethyl bromo thietan-3 -ylmethyl-

P.35 trifluoromethyl chloro thietan-3 -ylmethyl- thietan-3 -ylmethyl-

Table IP

Table IP provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 2Ρ

Table 2Ρ provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 3P

Table 3P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is fluoro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 4P

Table 4P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 5P

Table 5P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 6P

Table 6P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 7P

Table 7P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Br, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 8P

Table 8P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-I, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 9P

Table 9P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, Xlis fluoro, X2 is C-F, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 10P

Table 10P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X2 is bromo, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px. Table I IP

Table I IP provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 12P

Table 12P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 13P

Table 13P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 14P

Table 14P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 15P

Table 15P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is C-CL, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Table 16P

Table 16P provides 36 compounds of Formula A-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Px.

Compounds disclosed in Tables IP, 5P, 6P and 14P are of particular interest.

In one embodiment the invention provides a compound selected from Tables IP to 16P for use against rice pests.

In one embodiment the invention provides a compound selected from Tables IP to 16P for use against stemborer, particularly in rice.

Sesamia sp, Sesamia inferens.

In one embodiment the invention provides a compound selected from Tables IP to 16P for use against leaffolder, particularly in rice.

In one embodiment the invention provides a compound selected from Tables IP to 16P for use against hoppers, particularly in rice.

In one embodiment the invention provides a compound selected from Tables IP to 16P for use against gallmidge, particularly in rice.

Examples of Gall midge include Orseolia sp, Orseolia oryzae. In one embodiment the invention provides a compound selected from Tables IP to 16P for use against whorl maggot, particularly in rice.

Examples of whorl maggots include Hydrellia sp, Hydrellia philippina.

In one embodiment the invention provides a compound selected from Tables IP to 16P for use against Rice bugs, particularly in rice.

Examples of rice bugs include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta.

In one embodiment the invention provides a compound selected from Tables IP to 16P for use against Black bugs, particularly in rice.

Examples of Black bugs include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida,

Scotinophara latiuscula.

In a further aspect the invention provides a method comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula A'

wherein

G¹ is oxygen;

R¹ is hydrogen;

R² is thietan-3-yl-, l -oxo-thietan-3-yl-, l ,l -dioxo-thietan-3-yl-, thietan-3-ylmethyl-, l -oxo-thietan-3- ylmethyl-, or l ,l -dioxo-thietan-3-ylmethyl-;

Y^ and Y³ are independently CH or nitrogen;

wherein no more than two of Y¹, Y² and Y³ are nitrogen and wherein Y² and Y³ are not both nitrogen; R⁵ is hydrogen, halogen, cyano, nitro, NH₂, Ci-C₂alkyl, Ci-C₂haloalkyl, C3-C₅cycloalkyl, d- C₂halocycloalkyl, Ci-C₂alkoxy, Ci-C₂haloalkoxy;

X² is C-X⁶;

X¹, X³ and X⁶ are independently halogen or trihalomethyl;

X⁴ is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.

Preferred values of R², R⁵, Y¹, Y², Y³, X¹, X², X³, X⁴ and X⁶ for the compound of formula A' are, in any combination, as set out below.

Preferably R² is thietan-3-yl-, l -oxo-thietan-3-yl-, or l ,l -dioxo-thietan-3-yl-.

Preferably R⁵ is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, more preferably R⁵ is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, nitro, cyano, cyclopropyl, even more preferably R⁵ is chloro, bromo, fluoro, methyl, trifluoromethyl. Most preferably R⁵ is chloro or methyl.

1 2 3 1 2 3 1

Preferably X is chloro, X is C-Br, X is chloro, or X is chloro, X is C-F, X is chloro, or X is chloro, X² is C-Cl, X³ is chloro, or X¹ is chloro, X² is C-I, X³ is chloro, or X¹ is fluoro, X² is C-F, X³ is

1 2 3 1 2 3 fluoro, or X is chloro, X is C-Cl, X is trifluoromethyl, or X is trifluoromethyl, X is C-Cl, X is

1 2 3 1 2 3 trifluoromethyl. More preferably X is chloro, X is C-Cl, X is chloro, or X is chloro, X is C-F, X is chloro.

Preferably X⁴ is trifluoromethyl.

In one embodiment the invention provides compounds of formula A' wherein

G¹ is oxygen;

R¹ is hydrogen;

R² is thietan-3-yl-, l -oxo-thietan-3-yl-, l,l -dioxo-thietan-3-yl-, thietan-3-ylmethyl-, 1-oxo- thietan-3-ylmethyl-, or l,l -dioxo-thietan-3-ylmethyl-;

Y¹ is CH, Y² is CH, Y³ is CH;

R⁵ is chloro, bromo, fluoro, methyl, trifluoromethyl;

1 2 3 1 2 3

X is chloro, X is C-Cl, X is chloro, or X is chloro, X is C-F, X is chloro; and

X⁴ is trifluoromethyl.

In another embodiment the invention provides compounds of formula A' wherein

G¹ is oxygen;

R¹ is hydrogen;

R² is thietan-3-yl-, l -oxo-thietan-3-yl-, l,l -dioxo-thietan-3-yl-;

Y¹ is CH, Y² is CH, Y³ is CH;

R⁵ is chloro, bromo, fluoro, methyl, trifluoromethyl;

1 2 3 1 2 3

X is chloro, X is C-Cl, X is chloro, or X is chloro, X is C-F, X is chloro; and

X⁴ is trifluoromethyl.

In embodiment the invention provides compounds of formula A' wherein X¹ is chloro, X² is C- Br, X³ is chloro and G¹, R¹, R², R⁵, Y¹, Y², Y³ and X⁴ are as defined for the compound of formula A'.

In embodiment the invention provides compounds of formula A' wherein X¹ is chloro, X² is C-F,

3 1 1 2 5 1 2 3 4

X^J is chloro and G , R , R R^D, Y , Y Y^J and X" are as defined for the compound of formula A'.

In embodiment the invention provides compounds of formula A' wherein X¹ is chloro, X² is C- Cl, X³ is chloro and G¹, R¹, R², R⁵, Y¹, Y², Y³ and X⁴ are as defined for the compound of formula A'.

In embodiment the invention provides compounds of formula A' wherein X¹ is chloro, X² is C-I,

3 1 1 2 5 1 2 3 4

X^J is chloro and G , R , R R^D, Y , Y Y^J and X" are as defined for the compound of formula A'. In embodiment the invention provides compounds of formula A' wherein X¹ is fluoro, X² is C-F,

3 1 1 2 5 1 2 3 4

X^J is fluoro and G , R , R R^D, Y , Y Y^J and X" are as defined for the compound of formula A'.

In embodiment the invention provides compounds of formula A' wherein X¹ is chloro, X² is C-

3 1 1 2 5 1 2 3 4

Cl, X^J is trifluoromethyl and G , R , R R^D, Y , Y Y^J and X" are as defined for the compound of formula A'.

In embodiment the invention provides compounds of formula A' wherein X¹ is trifluoromethyl, X² is C-Cl, X³ is trifluoromethyl and G¹, R¹, R², R⁵, Y¹, Y², Y³ and X⁴ are as defined for the compound of formula A'.

Table Q indicates compounds of formula A'according to the above aspect of the invention.

Table 0

Stereochemistry

X4 R5 R2 at ixoszoline

Q.l trifluoromethyl bromo 1 , 1 -dioxo-thietan-3 -yl- S

Q.2 trifluoromethyl chloro 1 , 1 -dioxo-thietan-3 -yl- S

Q.3 trifluoromethyl cyano 1 , 1 -dioxo-thietan-3 -yl- s

Q.4 trifluoromethyl cyclopropyl 1 , 1 -dioxo-thietan-3 -yl- s

Q.5 trifluoromethyl ethyl 1 , 1 -dioxo-thietan-3 -yl- s

Q.6 trifluoromethyl fluoro 1 , 1 -dioxo-thietan-3 -yl- s

Q.7 trifluoromethyl hydrogen 1 , 1 -dioxo-thietan-3 -yl- s

Q.8 trifluoromethyl methoxy 1 , 1 -dioxo-thietan-3 -yl- s

Q.9 trifluoromethyl methyl 1 , 1 -dioxo-thietan-3 -yl- s

Q.10 trifluoromethyl nitro 1 , 1 -dioxo-thietan-3 -yl- s

Q.l l trifluoromethyl trifluoromethoxy 1 , 1 -dioxo-thietan-3 -yl- s

Q.12 trifluoromethyl trifluoromethyl 1 , 1 -dioxo-thietan-3 -yl- s

Q.13 trifluoromethyl bromo 1 , 1 -dioxo-thietan-3 -ylmethyl- s

Q.14 trifluoromethyl chloro 1 , 1 -dioxo-thietan-3 -ylmethyl- s

Q.15 trifluoromethyl cyano 1 , 1 -dioxo-thietan-3 -ylmethyl- s

Q.16 trifluoromethyl cyclopropyl 1 , 1 -dioxo-thietan-3 -ylmethyl- s

Q.17 trifluoromethyl ethyl 1 , 1 -dioxo-thietan-3 -ylmethyl- s

Q.18 trifluoromethyl fluoro 1 , 1 -dioxo-thietan-3 -ylmethyl- s

Q.19 trifluoromethyl hydrogen 1 , 1 -dioxo-thietan-3 -ylmethyl- s

Q.20 trifluoromethyl methoxy 1 , 1 -dioxo-thietan-3 -ylmethyl- s

Q.21 trifluoromethyl methyl 1 , 1 -dioxo-thietan-3 -ylmethyl- s

Q.22 trifluoromethyl nitro 1 , 1 -dioxo-thietan-3 -ylmethyl- s

Q.23 trifluoromethyl trifluoromethoxy 1 , 1 -dioxo-thietan-3 -ylmethyl- s

Q.24 trifluoromethyl trifluoromethyl 1 , 1 -dioxo-thietan-3 -ylmethyl- s

Q.25 trifluoromethyl bromo cis-l-oxo-thietan-3-yl- s

Q.26 trifluoromethyl chloro cis-l-oxo-thietan-3-yl- s

Q.27 trifluoromethyl cyano cis-l-oxo-thietan-3-yl- s

Q.28 trifluoromethyl cyclopropyl cis-l-oxo-thietan-3-yl- s

Q.29 trifluoromethyl ethyl cis-l-oxo-thietan-3-yl- s

Q.30 trifluoromethyl fluoro cis-l-oxo-thietan-3-yl- s

Q.31 trifluoromethyl hydrogen cis-l-oxo-thietan-3-yl- s

Q.32 trifluoromethyl methoxy cis-l-oxo-thietan-3-yl- s Q.33 trifluoromethyl methyl cis-l-oxo-thietan-3-yl- S

Q.34 trifluoromethyl nitro cis-l-oxo-thietan-3-yl- S

Q.35 trifluoromethyl trifluoromethoxy cis-l-oxo-thietan-3-yl- S

Q.36 trifluoromethyl trifluoromethyl cis-l-oxo-thietan-3-yl- S

Q.37 trifluoromethyl bromo cis-l-oxo-thietan-3-ylmethyl- S

Q.38 trifluoromethyl chloro cis-l-oxo-thietan-3-ylmethyl- S

Q.39 trifluoromethyl cyano cis-l-oxo-thietan-3-ylmethyl- S

Q.40 trifluoromethyl cyclopropyl cis-l-oxo-thietan-3-ylmethyl- S

Q.41 trifluoromethyl ethyl cis-l-oxo-thietan-3-ylmethyl- S

Q.42 trifluoromethyl fluoro cis-l-oxo-thietan-3-ylmethyl- S

Q.43 trifluoromethyl hydrogen cis-l-oxo-thietan-3-ylmethyl- S

Q.44 trifluoromethyl methoxy cis-l-oxo-thietan-3-ylmethyl- S

Q.45 trifluoromethyl methyl cis-l-oxo-thietan-3-ylmethyl- S

Q.46 trifluoromethyl nitro cis-l-oxo-thietan-3-ylmethyl- S

Q.47 trifluoromethyl trifluoromethoxy cis-l-oxo-thietan-3-ylmethyl- S

Q.48 trifluoromethyl trifluoromethyl cis-l-oxo-thietan-3-ylmethyl- S

Q.49 trifluoromethyl bromo thietan-3-yl- S

Q.50 trifluoromethyl chloro thietan-3-yl- S

Q.51 trifluoromethyl cyano thietan-3-yl- S

Q.52 trifluoromethyl cyclopropyl thietan-3-yl- S

Q.53 trifluoromethyl ethyl thietan-3-yl- S

Q.54 trifluoromethyl fluoro thietan-3-yl- S

Q.55 trifluoromethyl hydrogen thietan-3-yl- S

Q.56 trifluoromethyl methoxy thietan-3-yl- S

Q.57 trifluoromethyl methyl thietan-3-yl- S

Q.58 trifluoromethyl nitro thietan-3-yl- S

Q.59 trifluoromethyl trifluoromethoxy thietan-3-yl- s

Q.60 trifluoromethyl trifluoromethyl thietan-3-yl- s

Q.61 trifluoromethyl bromo thietan-3 -ylmethyl- s

Q.62 trifluoromethyl chloro thietan-3 -ylmethyl- s

Q.63 trifluoromethyl cyano thietan-3 -ylmethyl- s

Q.64 trifluoromethyl cyclopropyl thietan-3 -ylmethyl- s

Q.65 trifluoromethyl ethyl thietan-3 -ylmethyl- s

Q.66 trifluoromethyl fluoro thietan-3 -ylmethyl- s

Q.67 trifluoromethyl hydrogen thietan-3 -ylmethyl- s

Q.68 trifluoromethyl methoxy thietan-3 -ylmethyl- s

Q.69 trifluoromethyl methyl thietan-3 -ylmethyl- s

Q.70 trifluoromethyl nitro thietan-3 -ylmethyl- s

Q.71 trifluoromethyl trifluoromethoxy thietan-3 -ylmethyl- s

Q.72 trifluoromethyl trifluoromethyl thietan-3 -ylmethyl- s

Q.73 trifluoromethyl bromo 1 , 1 -dioxo-thietan-3-yl-

Q.74 trifluoromethyl chloro 1 , 1 -dioxo-thietan-3-yl-

Q.75 trifluoromethyl cyano 1 , 1 -dioxo-thietan-3-yl-

Q.76 trifluoromethyl cyclopropyl 1 , 1 -dioxo-thietan-3-yl-

Q.77 trifluoromethyl ethyl 1 , 1 -dioxo-thietan-3-yl-

Q.78 trifluoromethyl fluoro 1 , 1 -dioxo-thietan-3-yl- Q.79 trifluoromethyl hydrogen 1 , 1 -dioxo-thietan-3 -yl-

Q.80 trifluoromethyl methoxy 1 , 1 -dioxo-thietan-3 -yl-

Q.81 trifluoromethyl methyl 1 , 1 -dioxo-thietan-3 -yl-

Q.82 trifluoromethyl nitro 1 , 1 -dioxo-thietan-3 -yl-

Q.83 trifluoromethyl trifluoromethoxy 1 , 1 -dioxo-thietan-3 -yl-

Q.84 trifluoromethyl trifluoromethyl 1 , 1 -dioxo-thietan-3 -yl-

Q.85 trifluoromethyl bromo 1 , 1 -dioxo-thietan-3 -ylmethyl -

Q.86 trifluoromethyl chloro 1 , 1 -dioxo-thietan-3 -ylmethyl -

Q.87 trifluoromethyl cyano 1 , 1 -dioxo-thietan-3 -ylmethyl -

Q.88 trifluoromethyl cyclopropyl 1 , 1 -dioxo-thietan-3 -ylmethyl -

Q.89 trifluoromethyl ethyl 1 , 1 -dioxo-thietan-3 -ylmethyl -

Q.90 trifluoromethyl fluoro 1 , 1 -dioxo-thietan-3 -ylmethyl -

Q.91 trifluoromethyl hydrogen 1 , 1 -dioxo-thietan-3 -ylmethyl -

Q.92 trifluoromethyl methoxy 1 , 1 -dioxo-thietan-3 -ylmethyl -

Q.93 trifluoromethyl methyl 1 , 1 -dioxo-thietan-3 -ylmethyl -

Q.94 trifluoromethyl nitro 1 , 1 -dioxo-thietan-3 -ylmethyl -

Q.95 trifluoromethyl trifluoromethoxy 1 , 1 -dioxo-thietan-3 -ylmethyl -

Q.96 trifluoromethyl trifluoromethyl 1 , 1 -dioxo-thietan-3 -ylmethyl -

Q.97 trifluoromethyl bromo cis-l-oxo-thietan-3-yl-

Q.98 trifluoromethyl chloro cis-l-oxo-thietan-3-yl-

Q.99 trifluoromethyl cyano cis-l-oxo-thietan-3-yl-

Q.100 trifluoromethyl cyclopropyl cis-l-oxo-thietan-3-yl-

Q.101 trifluoromethyl ethyl cis-l-oxo-thietan-3-yl-

Q.102 trifluoromethyl fluoro cis-l-oxo-thietan-3-yl-

Q.103 trifluoromethyl hydrogen cis-l-oxo-thietan-3-yl-

Q.104 trifluoromethyl methoxy cis-l-oxo-thietan-3-yl-

Q.105 trifluoromethyl methyl cis-l-oxo-thietan-3-yl-

Q.106 trifluoromethyl nitro cis-l-oxo-thietan-3-yl-

Q.107 trifluoromethyl trifluoromethoxy cis-l-oxo-thietan-3-yl-

Q.108 trifluoromethyl trifluoromethyl cis-l-oxo-thietan-3-yl-

Q.109 trifluoromethyl bromo cis-l-oxo-thietan-3-ylmethyl-

Q.110 trifluoromethyl chloro cis-l-oxo-thietan-3-ylmethyl-

Q.l l l trifluoromethyl cyano cis-l-oxo-thietan-3-ylmethyl-

Q.112 trifluoromethyl cyclopropyl cis-l-oxo-thietan-3-ylmethyl-

Q.113 trifluoromethyl ethyl cis-l-oxo-thietan-3-ylmethyl-

Q.114 trifluoromethyl fluoro cis-l-oxo-thietan-3-ylmethyl-

Q.115 trifluoromethyl hydrogen cis-l-oxo-thietan-3-ylmethyl-

Q.116 trifluoromethyl methoxy cis-l-oxo-thietan-3-ylmethyl-

Q.117 trifluoromethyl methyl cis-l-oxo-thietan-3-ylmethyl-

Q.118 trifluoromethyl nitro cis-l-oxo-thietan-3-ylmethyl-

Q.119 trifluoromethyl trifluoromethoxy cis-l-oxo-thietan-3-ylmethyl-

Q.120 trifluoromethyl trifluoromethyl cis-l-oxo-thietan-3-ylmethyl-

Q.121 trifluoromethyl bromo thietan-3-yl-

Q.122 trifluoromethyl chloro thietan-3-yl-

Q.123 trifluoromethyl cyano thietan-3-yl-

Q.124 trifluoromethyl cyclopropyl thietan-3-yl- Q.125 trifluoromethyl ethyl thietan-3-yl-

Q.126 trifluoromethyl fluoro thietan-3-yl-

Q.127 trifluoromethyl hydrogen thietan-3-yl-

Q.128 trifluoromethyl methoxy thietan-3-yl-

Q.129 trifluoromethyl methyl thietan-3-yl-

Q.130 trifluoromethyl nitro thietan-3-yl-

Q.131 trifluoromethyl trifluoromethoxy thietan-3-yl-

Q.132 trifluoromethyl trifluoromethyl thietan-3-yl-

Q.133 trifluoromethyl bromo thietan-3 -ylmethyl-

Q.134 trifluoromethyl chloro thietan-3 -ylmethyl-

Q.135 trifluoromethyl cyano thietan-3 -ylmethyl-

Q.136 trifluoromethyl cyclopropyl thietan-3 -ylmethyl-

Q.137 trifluoromethyl ethyl thietan-3 -ylmethyl-

Q.138 trifluoromethyl fluoro thietan-3 -ylmethyl-

Q.139 trifluoromethyl hydrogen thietan-3 -ylmethyl-

Q.140 trifluoromethyl methoxy thietan-3 -ylmethyl-

Q.141 trifluoromethyl methyl thietan-3 -ylmethyl-

Q.142 trifluoromethyl nitro thietan-3 -ylmethyl-

Q.143 trifluoromethyl trifluoromethoxy thietan-3 -ylmethyl-

Q.144 trifluoromethyl trifluoromethyl thietan-3 -ylmethyl-

Table 10

Table 1Q provides 144 compounds of Formula A'-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.

Table 20

Table 2Q provides 144 compounds of Formula A'-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.

Table 30

Table 3Q provides 144 compounds of Formula A'-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Br, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.

Table 40

Table 4Q provides 144 compounds of Formula A'-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-I, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.

Table 50 Table 5Q provides 144 compounds of Formula A'-A wherein Gl is oxygen, Rl is hydrogen, Xlis fluoro, X2 is C-F, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.

Table 60

Table 6Q provides 144 compounds of Formula A'-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.

Table 70

Table 7Q provides 144 compounds of Formula A'-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is C-CL, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.

Compounds in Tables 1 Q and 2Q are of particular interest.

In one embodiment the invention provides a compound selected from Tables 1Q to 7Q for use against rice pests.

In one embodiment the invention provides a compound selected from Tables 1Q to 7Q for use against stemborer, particularly in rice.

Sesamia sp, Sesamia inferens.

In one embodiment the invention provides a compound selected from Tables 1Q to 7Q for use against leaffolder, particularly in rice.

In one embodiment the invention provides a compound selected from Tables 1Q to 7Q for use against hoppers, particularly in rice.

In one embodiment the invention provides a compound selected from Tables 1Q to 7Q for use against gallmidge, particularly in rice.

Examples of Gall midge include Orseolia sp, Orseolia oryzae.

In one embodiment the invention provides a compound selected from Tables 1Q to 7Q for use against whorl maggot, particularly in rice.

Examples of whorl maggots include Hydrellia sp, Hydrellia philippina.

In one embodiment the invention provides a compound selected from Tables 1Q to 7Q for use against Rice bugs, particularly in rice.

Leptocorisa acuta.

In one embodiment the invention provides a compound selected from Tables 1Q to 7Q for use against Black bugs, particularly in rice.

Examples of Black bugs include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula. In a further aspect the invention provides a method comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula A"

G¹ is oxygen;

R¹ is hydrogen;

R² is thietan-3-ylmethyl-, l -oxo-thietan-3-ylmethyl-, l , l -dioxo-thietan-3-ylmethyl-;

Y¹, Y² and Y³ are independently CH or nitrogen;

wherein no more than two of Y¹, Y² and Y³ are nitrogen and wherein Y² and Y³ are not both nitrogen; R⁵ is hydrogen, halogen, cyano, nitro, NH₂, Ci-C₂alkyl, Ci-C₂haloalkyl, C₃-C₅cycloalkyl, C_r

C₂halocycloalkyl, Ci-C₂alkoxy, Ci-C₂haloalkoxy;

X² is C-X⁶ or nitrogen;

X⁴ is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.

Preferred values of R², R⁵, Y¹, Y², Y³, X¹, X², X³, X⁴ and X⁶ for compounds of formula A" are, in any combination, as set out below.

Preferably X¹ is chloro, X² is CH, X³ is chloro, or X¹ is chloro, X² is C-F, X³ is hydrogen, or X¹

2 3 1 2 3 1 2 is fluoro, X is C-Cl, X is hydrogen, or X is chloro, X is C-Cl, X is hydrogen, or X is chloro, X is C-

3 1 2 3 1 2 3 1

Br, X is chloro, or X is chloro, X is C-F, X is chloro, or X is chloro, X is C-Cl, X is chloro, or X is

2 3 1 2 3 1 2 3 chloro, X is C-I, X is chloro, or X is fluoro, X is C-F, X is fluoro, orX is chloro, X is CH, X is

1 2 3 1 2 3 1 bromo, or X is chloro, X is CH, X is fluoro, orX is chloro, X is CH, X is trifluoromethyl, or X is

2 3 1 2 3 1 chloro, X is C-Cl, X is trifluoromethyl, or X is trifluoromethyl, X is CH, X is trifluoromethyl, or X is trifluoromethyl, X² is C-Cl, X³ is trifluoromethyl, or X¹ is trifluoromethyl, X² is CH, X³ is hydrogen, or X 1 is chloro, X2 is N, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl. Preferably X 1 is chloro, X² is CH, X³ is chloro, or X¹ is chloro, X² is C-Cl, X³ is chloro, or X¹ is chloro, X² is C-F, X³ is chloro, or X¹ is trifluoromethyl, X² is CH, X³ is trifluoromethyl. Most preferably X¹ is chloro, X² is CH, X³ is chloro.

Preferably X⁴ is trifluoromethyl.

In one embodiment the invention provides compounds of formula A" wherein

G¹ is oxygen;

Pv¹ is hydrogen;

R² is thietan-3-ylmethyl-, l-oxo-thietan-3-ylmethyl-, or l,l -dioxo-thietan-3-ylmethyl-;

Y¹ is CH, Y² is CH, Y³ is CH;

R⁵ is chloro, bromo, fluoro, methyl, trifluoromethyl;

X⁴ is trifluoromethyl.

In embodiment the invention provides compounds of formula A" wherein R² is thietan-3- ylmethyl- and G¹, R¹, R⁵, Y¹, Y², Y³, X¹, X², X³ and X⁴ are as defined for the compound of formula A" .

In embodiment the invention provides compounds of formula A" wherein R² is l-oxo-thietan-3- ylmethyl- and G¹, R¹, R⁵, Y¹, Y², Y³, X¹, X², X³ and X⁴ are as defined for the compound of formula A" .

In embodiment the invention provides compounds of formula A" wherein R² is 1 ,1-dioxo- thietan-3-ylmethyl- and G¹, R¹, R⁵, Y¹, Y², Y³, X¹, X², X³ and X⁴ are as defined for the compound of formula A" .

Table S indicates compounds according to the above aspect of the invention.

Table S

Stereochemistry at

X4 R5 R2 isoxaozline

S.l trifluoromethyl bromo 1 , 1 -dioxo-thietan-3 -ylmethyl- S

S.2 trifluoromethyl chloro 1 , 1 -dioxo-thietan-3 -ylmethyl- S

S.3 trifluoromethyl cyano 1 , 1 -dioxo-thietan-3 -ylmethyl- s

S.4 trifluoromethyl cyclopropyl 1 , 1 -dioxo-thietan-3 -ylmethyl- s

S.5 trifluoromethyl ethyl 1 , 1 -dioxo-thietan-3 -ylmethyl- s

S.6 trifluoromethyl fluoro 1 , 1 -dioxo-thietan-3 -ylmethyl- s

S.7 trifluoromethyl hydrogen 1 , 1 -dioxo-thietan-3 -ylmethyl- s

S.8 trifluoromethyl methoxy 1 , 1 -dioxo-thietan-3 -ylmethyl- s

S.9 trifluoromethyl methyl 1 , 1 -dioxo-thietan-3 -ylmethyl- s

S.10 trifluoromethyl nitro 1 , 1 -dioxo-thietan-3 -ylmethyl- s

S.l l trifluoromethyl trifluoromethoxy 1 , 1 -dioxo-thietan-3 -ylmethyl- s

S.12 trifluoromethyl trifluoromethyl 1 , 1 -dioxo-thietan-3 -ylmethyl- s

S.13 trifluoromethyl bromo cis-1 -oxo-thietan-3-ylmethyl- s

S.14 trifluoromethyl chloro cis-1 -oxo-thietan-3-ylmethyl- s

S.15 trifluoromethyl cyano cis-1 -oxo-thietan-3-ylmethyl- s

S.16 trifluoromethyl cyclopropyl cis-1 -oxo-thietan-3-ylmethyl- s S.17 trifluoromethyl ethyl cis-1 -oxo -thietan-3 -ylmethyl- S

S.18 trifluoromethyl fluoro cis-1 -oxo -thietan-3 -ylmethyl- S

S.19 trifluoromethyl hydrogen cis-1 -oxo -thietan-3 -ylmethyl- S

S.20 trifluoromethyl methoxy cis-1 -oxo -thietan-3 -ylmethyl- S

S.21 trifluoromethyl methyl cis-1 -oxo -thietan-3 -ylmethyl- S

S.22 trifluoromethyl nitro cis-1 -oxo -thietan-3 -ylmethyl- S

S.23 trifluoromethyl trifluoromethoxy cis-1 -oxo -thietan-3 -ylmethyl- S

S.24 trifluoromethyl trifluoromethyl cis-1 -oxo -thietan-3 -ylmethyl- S

S.25 trifluoromethyl bromo thietan-3 -ylmethyl- S

S.26 trifluoromethyl chloro thietan-3 -ylmethyl- S

S.27 trifluoromethyl cyano thietan-3 -ylmethyl- S

S.28 trifluoromethyl cyclopropyl thietan-3 -ylmethyl- S

S.29 trifluoromethyl ethyl thietan-3 -ylmethyl- S

S.30 trifluoromethyl fluoro thietan-3 -ylmethyl- S

S.31 trifluoromethyl hydrogen thietan-3 -ylmethyl- S

S.32 trifluoromethyl methoxy thietan-3 -ylmethyl- S

S.33 trifluoromethyl methyl thietan-3 -ylmethyl- S

S.34 trifluoromethyl nitro thietan-3 -ylmethyl- S

S.35 trifluoromethyl trifluoromethoxy thietan-3 -ylmethyl- S

S.36 trifluoromethyl trifluoromethyl thietan-3 -ylmethyl- S

P.37 trifluoromethyl bromo 1 , 1 -dioxo -thietan-3 -ylmethyl-

P.38 trifluoromethyl chloro 1 , 1 -dioxo -thietan-3 -ylmethyl-

P.39 trifluoromethyl cyano 1 , 1 -dioxo -thietan-3 -ylmethyl-

P.40 trifluoromethyl cyclopropyl 1 , 1 -dioxo -thietan-3 -ylmethyl-

P.41 trifluoromethyl ethyl 1 , 1 -dioxo -thietan-3 -ylmethyl-

P.42 trifluoromethyl fluoro 1 , 1 -dioxo -thietan-3 -ylmethyl-

P.43 trifluoromethyl hydrogen 1 , 1 -dioxo -thietan-3 -ylmethyl-

P.44 trifluoromethyl methoxy 1 , 1 -dioxo -thietan-3 -ylmethyl-

P.45 trifluoromethyl methyl 1 , 1 -dioxo -thietan-3 -ylmethyl-

P.46 trifluoromethyl nitro 1 , 1 -dioxo -thietan-3 -ylmethyl-

P.47 trifluoromethyl trifluoromethoxy 1 , 1 -dioxo -thietan-3 -ylmethyl-

P.48 trifluoromethyl trifluoromethyl 1 , 1 -dioxo -thietan-3 -ylmethyl-

P.49 trifluoromethyl bromo cis-1 -oxo -thietan-3 -ylmethyl-

P.50 trifluoromethyl chloro cis-1 -oxo -thietan-3 -ylmethyl-

P.51 trifluoromethyl cyano cis-1 -oxo -thietan-3 -ylmethyl-

P.52 trifluoromethyl cyclopropyl cis-1 -oxo -thietan-3 -ylmethyl-

P.53 trifluoromethyl ethyl cis-1 -oxo -thietan-3 -ylmethyl-

P.54 trifluoromethyl fluoro cis-1 -oxo -thietan-3 -ylmethyl-

P.55 trifluoromethyl hydrogen cis-1 -oxo -thietan-3 -ylmethyl-

P.56 trifluoromethyl methoxy cis-1 -oxo -thietan-3 -ylmethyl-

P.57 trifluoromethyl methyl cis-1 -oxo -thietan-3 -ylmethyl-

P.58 trifluoromethyl nitro cis-1 -oxo -thietan-3 -ylmethyl-

P.59 trifluoromethyl trifluoromethoxy cis-1 -oxo -thietan-3 -ylmethyl-

P.60 trifluoromethyl trifluoromethyl cis-1 -oxo -thietan-3 -ylmethyl-

P.61 trifluoromethyl bromo thietan-3 -ylmethyl-

P.62 trifluoromethyl chloro thietan-3 -ylmethyl-

Table I S

Table I S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 2S

Table 2S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 3S

Table 3S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is fluoro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 4S

Table 4S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 5S

Table 5S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 6S

Table 6S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 7S

Table 7S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Br, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 8S

Table 8S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-I, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 9S

Table 9S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, Xlis fluoro, X2 is C-F, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table IPS

Table 10S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X2 is bromo, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table U S

Table 1 I S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 12S

Table 12S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 13S

Table 13S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 14S

Table 14S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 15S

Table 15S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is C-Cl, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Table 16S

Table 16S provides 72 compounds of Formula A"-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.

Compounds disclosed in Tables I S, 5S, 6S and 14S are of particular interest.

In one embodiment the invention provides a compound selected from Tables IS to 16S for use against rice pests.

In one embodiment the invention provides a compound selected from Tables IS to 16S for use against stemborer, particularly in rice.

Sesamia sp, Sesamia inferens.

In one embodiment the invention provides a compound selected from Tables IS to 16S for use against leaffolder, particularly in rice.

In one embodiment the invention provides a compound selected from Tables IS to 16S for use against hoppers, particularly in rice. Examples of Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus, Nephotettix malayanus, Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera.

In one embodiment the invention provides a compound selected from Tables IS to 16S for use against gallmidge, particularly in rice.

Examples of Gall midge include Orseolia sp, Orseolia oryzae.

In one embodiment the invention provides a compound selected from Tables IS to 16S for use against whorl maggot, particularly in rice.

Examples of whorl maggots include Hydrellia sp, Hydrellia philippina.

In one embodiment the invention provides a compound selected from Tables IS to 16S for use against Rice bugs, particularly in rice.

In one embodiment the invention provides a compound selected from Tables IS to 16S for use against Black bugs, particularly in rice.

Scotinophara latiuscula.

In one embodiment the invention provides a compound selected from Tables IS to 16S for use against plutella spp..

In one embodiment the invention provides a compound selected from Tables IS to 16S for use against Plutella xylostella, particularly in brassica crops.

In one embodiment the invention provides a method of controlling and/or preventing infestation of hoppers in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A".

In one embodiment the invention provides a method of controlling and/or preventing infestation of hoppers in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A".

In one embodiment the invention provides a method of controlling and/or preventing infestation of stemborer in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A".

In one embodiment the invention provides a method of controlling and/or preventing infestation of stemborer in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A".

In one embodiment the invention provides a method of controlling and/or preventing infestation of leaffolder in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof. In one embodiment the invention provides a method of controlling and/or preventing infestation of leaffolder in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A".

In one embodiment the invention provides a method of controlling and/or preventing infestation of gallmidge in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A" .

In one embodiment the invention provides a method of controlling and/or preventing infestation of Gallmidge in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A".

In one embodiment the invention provides a method of controlling and/or preventing infestation of whorl maggot in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A".

In one embodiment the invention provides a method of controlling and/or preventing infestation of whorl maggot in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A" .

In one embodiment the invention provides a method of controlling and/or preventing infestation of Rice bugs in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A".

In one embodiment the invention provides a method of controlling and/or preventing infestation of Rice bugs in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A".

In one embodiment the invention provides a method of controlling and/or preventing infestation Black bugs in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A".

In one embodiment the invention provides a method of controlling and/or preventing infestation of Black bugs in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A".

The compounds of formula I, A, A' and A" may be prepared using the information provided in e.g.WO2009/080250, WO2010/020522 and WO2010/149506. WO2011/104089 and WO2011/154555 describe enantioselective routes to the compounds of formula I. The compounds in Scheme 1 may be prepared according to the methods described in WO2011/104089.

Scheme 1

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

Table Qs

R8a R8b R8c R5 L R8a R8b R8c R5 L

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

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

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

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

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

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

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

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

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

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

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

12 CI CI H CH3 - 408 CI CI H CH3 CH2

13 F CI H CH3 - 409 F CI H CH3 CH2 CF3 CI H CH3 - 410 CF3 CI H CH3 CH2

H F H CH3 - 411 H F H CH3 CH2

Br F H CH3 - 412 Br F H CH3 CH2

CI F H CH3 - 413 CI F H CH3 CH2

F F H CH3 - 414 F F H CH3 CH2

CF3 F H CH3 - 415 CF3 F H CH3 CH2

H H Br CH3 - 416 H H Br CH3 CH2

Br H Br CH3 - 417 Br H Br CH3 CH2

CI H Br CH3 - 418 CI H Br CH3 CH2

F H Br CH3 - 419 F H Br CH3 CH2

CF3 H Br CH3 - 420 CF3 H Br CH3 CH2

H Br Br CH3 - 421 H Br Br CH3 CH2

Br Br Br CH3 - 422 Br Br Br CH3 CH2

CI Br Br CH3 - 423 CI Br Br CH3 CH2

F Br Br CH3 - 424 F Br Br CH3 CH2

CF3 Br Br CH3 - 425 CF3 Br Br CH3 CH2

H CI Br CH3 - 426 H CI Br CH3 CH2

Br CI Br CH3 - 427 Br CI Br CH3 CH2

CI CI Br CH3 - 428 CI CI Br CH3 CH2

F CI Br CH3 - 429 F CI Br CH3 CH2

CF3 CI Br CH3 - 430 CF3 CI Br CH3 CH2

H F Br CH3 - 431 H F Br CH3 CH2

Br F Br CH3 - 432 Br F Br CH3 CH2

CI F Br CH3 - 433 CI F Br CH3 CH2

F F Br CH3 - 434 F F Br CH3 CH2

CF3 F Br CH3 - 435 CF3 F Br CH3 CH2

H H CI CH3 - 436 H H CI CH3 CH2

Br H CI CH3 - 437 Br H CI CH3 CH2

CI H CI CH3 - 438 CI H CI CH3 CH2

F H CI CH3 - 439 F H CI CH3 CH2

CF3 H CI CH3 - 440 CF3 H CI CH3 CH2

H Br CI CH3 - 441 H Br CI CH3 CH2

Br Br CI CH3 - 442 Br Br CI CH3 CH2

CI Br CI CH3 - 443 CI Br CI CH3 CH2

F Br CI CH3 - 444 F Br CI CH3 CH2

CF3 Br CI CH3 - 445 CF3 Br CI CH3 CH2

H CI CI CH3 - 446 H CI CI CH3 CH2

Br CI CI CH3 - 447 Br CI CI CH3 CH2

CI CI CI CH3 - 448 CI CI CI CH3 CH2

F CI CI CH3 - 449 F CI CI CH3 CH2

CF3 CI CI CH3 - 450 CF3 CI CI CH3 CH2

H F CI CH3 - 451 H F CI CH3 CH2

Br F CI CH3 - 452 Br F CI CH3 CH2

CI F CI CH3 - 453 CI F CI CH3 CH2

F F CI CH3 - 454 F F CI CH3 CH2

CF3 F CI CH3 - 455 CF3 F CI CH3 CH2 H H F CH3 - 456 H H F CH3 CH2

Br H F CH3 - 457 Br H F CH3 CH2

CI H F CH3 - 458 CI H F CH3 CH2

F H F CH3 - 459 F H F CH3 CH2

CF3 H F CH3 - 460 CF3 H F CH3 CH2

H Br F CH3 - 461 H Br F CH3 CH2

Br Br F CH3 - 462 Br Br F CH3 CH2

CI Br F CH3 - 463 CI Br F CH3 CH2

F Br F CH3 - 464 F Br F CH3 CH2

CF3 Br F CH3 - 465 CF3 Br F CH3 CH2

H CI F CH3 - 466 H CI F CH3 CH2

Br CI F CH3 - 467 Br CI F CH3 CH2

CI CI F CH3 - 468 CI CI F CH3 CH2

F CI F CH3 - 469 F CI F CH3 CH2

CF3 CI F CH3 - 470 CF3 CI F CH3 CH2

H F F CH3 - 471 H F F CH3 CH2

Br F F CH3 - 472 Br F F CH3 CH2

CI F F CH3 - 473 CI F F CH3 CH2

F F F CH3 - 474 F F F CH3 CH2

CF3 F F CH3 - 475 CF3 F F CH3 CH2

H H CF3 CH3 - 476 H H CF3 CH3 CH2

Br H CF3 CH3 - 477 Br H CF3 CH3 CH2

CI H CF3 CH3 - 478 CI H CF3 CH3 CH2

F H CF3 CH3 - 479 F H CF3 CH3 CH2

CF3 H CF3 CH3 - 480 CF3 H CF3 CH3 CH2

H Br CF3 CH3 - 481 H Br CF3 CH3 CH2

Br Br CF3 CH3 - 482 Br Br CF3 CH3 CH2

CI Br CF3 CH3 - 483 CI Br CF3 CH3 CH2

F Br CF3 CH3 - 484 F Br CF3 CH3 CH2

CF3 Br CF3 CH3 - 485 CF3 Br CF3 CH3 CH2

H CI CF3 CH3 - 486 H CI CF3 CH3 CH2

Br CI CF3 CH3 - 487 Br CI CF3 CH3 CH2

CI CI CF3 CH3 - 488 CI CI CF3 CH3 CH2

F CI CF3 CH3 - 489 F CI CF3 CH3 CH2

CF3 CI CF3 CH3 - 490 CF3 CI CF3 CH3 CH2

H F CF3 CH3 - 491 H F CF3 CH3 CH2

Br F CF3 CH3 - 492 Br F CF3 CH3 CH2

CI F CF3 CH3 - 493 CI F CF3 CH3 CH2

F F CF3 CH3 - 494 F F CF3 CH3 CH2

CF3 F CF3 CH3 - 495 CF3 F CF3 CH3 CH2

Br H H Br - 496 Br H H Br CH2

CI H H Br - 497 CI H H Br CH2

F H H Br - 498 F H H Br CH2

CF3 H H Br - 499 CF3 H H Br CH2

H Br H Br - 500 H Br H Br CH2

Br Br H Br - 501 Br Br H Br CH2 106 CI Br H Br - 502 CI Br H Br CH2

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

150 Br CI CI Br - 546 Br CI CI Br CH2

151 CI CI CI Br - 547 CI CI CI Br CH2 152 F CI CI Br - 548 F CI CI Br CH2

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

197 F F CF3 Br - 593 F F CF3 Br CH2 198 CF3 F CF3 Br - 594 CF3 F CF3 Br CH2

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

242 CF3 H CI CI - 638 CF3 H CI CI CH2

243 H Br CI CI - 639 H Br CI CI CH2 244 Br Br CI CI - 640 Br Br CI CI CH2

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

288 H CI CF3 CI - 684 H CI CF3 CI CH2

289 Br CI CF3 CI - 685 Br CI CF3 CI CH2 290 CI CI CF3 CI - 686 CI CI CF3 CI CH2

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

335 F F Br CF3 - 731 F F Br CF3 CH2 336 CF3 F Br CF3 - 732 CF3 F Br CF3 CH2

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

380 F H CF3 CF3 - 776 F H CF3 CF3 CH2

381 CF3 H CF3 CF3 - 777 CF3 H CF3 CF3 CH2 382 H Br CF3 CF3 - 778 H Br CF3 CF3 CH2

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

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

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

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

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

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

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

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

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

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

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

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

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

396 CF3 F CF3 CF3 - 792 CF3 F CF3 CF3 CH2 he 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 may be before infestation or when the pest is present. Application of the compounds of the invention can be performed according to any of the usual modes of application, e.g. foliar, drench, soil, in furrow etc. However, control of Anthonomus grandis s is usually achieved by foliar application, which is the preferred mode of application according to the invention.

Application of the compounds of the invention is preferably to a crop of cotton plants, the locus thereof or propagation material thereof.

The compounds of the invention may be applied to plant parts. Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds. Treatment according to the invention of the plants and plant parts with the active compounds can be carried out directly or by allowing the compounds to act on their surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injecting and, in the case of propagation material, in particular in the case of seed, also by applying one or more coats.

The compounds of the invention are suitable for use on any plant (preferably cotton 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 "plant" as used herein includes seedlings, bushes and trees. Crops are to be understood as also including those crops 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 crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer rape (canola). Examples of crops 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). Transgenic cotton is of particular interest.

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 (PI 2) (cotton cultivars producing CrylAc and Cry2Ab2) and VIPCOT® (P13) (cotton cultivars producing a Vip3Aa). Soybean Cyst Nematode resistance soybean (SCN® - Syngenta (PI 4)) and soybean with Aphid resistant trait (AMT® (PI 5)) are also of interest.

Further examples of such transgenic crops are: 1. Btll Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 (P16). Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer {Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylA(b) toxin. Btl 1 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

2. Btl 76 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 (PI 7). Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer {Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylA(b) toxin. Btl 76 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 (PI 8). Maize which has been rendered insect-resistant by transgenic expression of a modified CrylllA toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-D-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.

4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-l 150 Brussels, Belgium, registration number C/DE/02/9 (P19). MON 863 expresses a CrylllB(bl) toxin and has resistance to certain Coleoptera insects.

5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-l 150 Brussels, Belgium, registration number C/ES/96/02. (P20)

6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-l 160 Brussels, Belgium, registration number C/NL/00/10. (P21) Genetically modified maize for the expression of the protein 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 ^χ MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylA(b) toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.

Further examples of transgenic plants, and of very high interest, are those carrying traits conferring resistance to 2.4D (e.g. Enlist®) (e.g. WO 2011066384) (, glyphosate (e.g. Roundup Ready® (P24), Roundup Ready 2 Yield® (P25)), sulfonylurea (e.g. STS®) (P26), glufosinate (e.g. Liberty Link® (P27), Ignite® (P28)), Dicamba (P29) (Monsanto), HPPD tolerance (P30) (e.g. isoxaflutole herbicide) (Bayer CropScience, Syngenta). Double or triple stacks of any of the traits described here are also of interest, including glyphosate and sulfonyl-urea tolerance ((e.g. Optimum GAT®) (P31), plants stacked with STS® and Roundup Ready® (P32) or plants stacked with STS® and Roundup Ready 2 Yield® (P33)), dicamba and glyphosate tolerance (P34) (Monsanto). Of particular interest are soybean plants carrying trains conferring resistance to 2.4D (e.g. Enlist®), glyphosate (e.g. Roundup Ready®, Roundup Ready 2 Yield®), sulfonylurea (e.g. STS®), glufosinate (e.g. Liberty Link®, Ignite®), Dicamba

(Monsanto) HPPD tolerance (e.g. isoxaflutole herbicide) (Bayer CropScience, Syngenta).

Transgenic crops of insect-resistant plants are also described in BATS (Zentrum fur Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003,

(http://bats.ch).

Herbicide -resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield(®) (for example maize).

These statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which plant cultivars will be developed and/or marketed in the future.

The compounds of the invention are suitable for use on any cotton 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, e.g. BT cotton.

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 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-methoxy-iminoacetamide (SSF-129), 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-l -sulfonamide,

a-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]-y-butyrolactone, 4-chloro-2-cyano-N,N-dimethyl-5-f>- 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-1 ,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propionamide (AC382042), N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide, acibenzolar (CGA245704) (e.g. acibenzolar-S-methyl), alanycarb, aldimorph, anilazine, azaconazole, azoxystrobin, benalaxyl, benomyl, benthiavalicarb, biloxazol, bitertanol, bixafen, blasticidin S, boscalid, bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chlorothalonil, chlorozolinate, clozylacon, copper containing compounds such as copper oxychloride, copper oxyquinolate, copper sulfate, copper tallate and Bordeaux mixture, cyclufenamid, cymoxanil, cyproconazole, cyprodinil, debacarb, di-2-pyridyl disulfide 1,1 '-dioxide, dichlofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, difenzoquat, diflumetorim,

OjO-di-wo-propyl-S-benzyl thiophosphate, dimefluazole, dimetconazole, dimethomorph, dimethirimol, diniconazole, dinocap, dithianon, dodecyl dimethyl ammonium chloride, dodemorph, dodine, doguadine, edifenphos, epoxiconazole, ethirimol, ethyl-(Z)-N-benzyl-N-([methyl(methyl-thioethylideneamino- oxycarbonyl)amino]thio)- -alaninate, etridiazole, famoxadone, fenamidone (RPA407213), fenarimol, fenbuconazole, fenfuram, fenhexamid (KBR2738), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, fluopyram,

fluoxastrobin, fluoroimide, fluquinconazole, flusilazole, flutolanil, flutriafol, fluxapyroxad, folpet, fuberidazole, furalaxyl, furametpyr, guazatine, hexaconazole, hydroxyisoxazole, hymexazole, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb (SZX0722), isopropanyl butyl carbamate, isoprothiolane, isopyrazam, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, mandipropamid, maneb, mefenoxam, metalaxyl, mepanipyrim, mepronil, metalaxyl, metconazole, metiram, metiram-zinc, metominostrobin, myclobutanil, neoasozin, nickel dimethyldithiocarbamate, nitrothal-wopropyl, nuarimol, ofurace, organomercury compounds, oxadixyl, oxasulfuron, oxolinic acid, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, penthiopyrad, phenazin oxide, phosetyl-Al, phosphorus acids, phthalide, picoxystrobin (ZA1963), polyoxinD, polyram, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, propionic acid, prothioconazole, pyrazophos, pyrifenox, pyrimethanil, pyraclostrobin, pyroquilon, pyroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinomethionate, quinoxyfen, quintozene, sedaxane, sipconazole (F-155), sodium pentachlorophenate, spiroxamine, streptomycin, sulfur, tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, thifluzamid, 2-(thiocyanomethylthio)benzothiazole, thiophanate -methyl, thiram, timibenconazole, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, tricyclazole, tridemorph, trifloxystrobin (CGA279202), triforine, triflumizole, triticonazole, validamycin A, vapam, vinclozolin, zineb and ziram, N- [9 -(dichloromethylene) -1,2,3,4 -tetrahydro- 1 ,4 -methanonaphthalen-5 -yl] -3 -(difluoromethyl) - 1 -methyl- lH-pyrazole-4-carboxamide [1072957-71 -1], l-methyl-3 -difluoromethyl- lH-pyrazole-4-carboxylic acid (2-dichloromethylene-3 -ethyl- 1 -methyl -indan-4-yl) -amide, and l -methyl-3-difluoromethyl-4H-pyrazole- 4-carboxylic acid [2-(2,4-dichloro-phenyl)-2-methoxy- 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.

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. 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 the compound of formula I to the additional active ingredient 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.

Mixtures with pyrethroids, in particular pymetrozine, are of particular interest for the present invention.

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.

In one embodiment the compounds of the invention are used for pest control on cotton at 1 :500 g/ha, for example 10-70g/ha. However, it should be noted that due to the very damaging effect of the Anthonomus grandis (quantity and quality on yield), sprays are often very intense and at very low threshold levels and can be down to almost zero tolerance.

When used in a seed dressing, a compound of the invention is used at a rate of 0.000 lg to lOg (for example O.OOlg or 0.05g), preferably 0.005g to lOg, more preferably 0.005g to 4g, per kilogram of seed.

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).

A compound of the invention may be applied by any of the known means of applying pesticidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapor or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water- soluble bag) in soil or an aqueous environment.

A compound of the invention may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.

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.

The following Examples do not limit the invention.

Biological Examples

Table A provides compounds of formula (la) wherein R^8a, R^8b, R^8c, A¹, R^5a, R^5b, A² and X have the definitions shown below.

No R8a R8b R8c Al B R5a R5b A2 X

A01 CI H CI CH2 N CH3 H CH P5

A02 CI H CI CH2 N CH3 H CH P2

A03 CI H CI CH2 N CH3 H CH P3 (cis)

A04 CI H CI CH2 N CH3 H CH P5

A05 CI CI CI O N CH3 H CH P4

A06 CI F CI O N CH3 H CH P4

A07 CI H CI O N CH3 H CH P7

A08 CI CI CI O N CH3 H CH P3 (cis)

A09 CI H CI O N CH3 H N P3 (cis)

A10 CI H CI O N CI H CH P3 (cis)

Al l CI H CI O N CH3 H CH P2

A12 CI H CI 0 N CH3 H CH P4 A13 CI CI CI 0 N CI H CH P3 (cis)

A14 CI F CI 0 N CI H CH P3 (cis)

A15 CI F CI 0 N CH3 H CH P3 (cis)

A16 CI F CI 0 N CH3 H CH P2

A17 CI CI CI 0 N CH3 H CH P2

A18 CF3 F H 0 N CH3 H CH P3 (cis)

A19 CF3 F H 0 N CH3 H CH P4

A20 CI F CI 0 N CI H CH P2

A21 CF3 H CI 0 N CH=CH-CH=CH CH P3 (cis)

A22 CF3 H H 0 N CH3 H CH P3 (cis)

A23 CI H CI 0 N CH3 H CH P3 (cis)

Table B provides compounds of formula (lb) wherein R^8a, R^8b, R^8c, A¹, R^5a, R^5b, A² and X have the definitions shown below.

No R8a R8b R8c Al B R5a R5b A2 X

B01 CI F CI CH2 N CH3 H CH P4

B02 CI F CI CH2 N CH3 H CH P3 (cis)

B03 CI F CI CH2 N CH3 H CH P2

B04 CI CI CI CH2 N CH3 H CH P5

B05 CI H CI CH2 N CH3 H CH P3 (cis)

B06 CI H F 0 N CH3 H CH P3 (cis)

B07 CI H F 0 N CH3 H CH P2

B08 CI H CI 0 N CF3 H CH P2

B09 CF3 H CF3 0 N CH3 H CH P2

BIO CI H CI 0 N Br H CH P2

Bl l CI H CI 0 N CF3 H CH P3 (cis)

B12 CI Br CI 0 N CH3 H CH P3 (cis)

B13 CI H CI 0 N CI H CH P3 (cis)

B14 CI H CI 0 N CI H N P4

B15 CI H CI 0 N CI H N P3 (cis)

B16 CF3 H CI 0 N CH3 H CH P3 (cis)

B17 CI CI H 0 N CH3 H CH P3 (cis)

B18 Br H CI 0 N CH3 H CH P3 (cis)

B19 CI Br CI 0 N CH3 H CH P2

B20 CI CI CI 0 N CH3 H CH P3 (cis)

B21 CI CI CI 0 N CH3 H CH P2

B22 CI F CI 0 N CH3 H CH P4

B23 CI H CI 0 N CH3 H CH P2

B24 CI H CI 0 N CH3 H CH P3 (cis)

P3

B25 CI H CI 0 N CH3 H CH (trans) B26 CI H CI 0 N CH=CH-CH=CH CH P2

B27 CF3 H CF3 0 N CH3 H CH P3 (cis)

B28 CF3 H H 0 N CH3 H CH P3 (cis)

B29 CI H CI CH2 N CH3 H CH P4

B30 CI H CI CH2 N CH3 H CH P2

B31 CI CI CI CH2 N CH3 H CH P2

B32 CI CI CI CH2 N CH3 H CH P4

B33 CI CI CI CH2 N CH3 H CH P3 (cis)

B34 CI H CI CH2 N CH=CH-CH=CH CH P3 (cis)

B35 CI H CI CH2 N CH=CH-CH=CH CH P2

B36 CI H CI CH2 N CH3 H CH P7

B37 CI H CI CH2 N CH3 H CH P9

B38 CI H CI 0 N CH3 H CH P4

Nephotettix virescens (Green leafhopper)

Rice seedlings are treated with the diluted test solutions in a spray chamber. After drying, plants are infested with 10 N₅ nymphs (3 replicates). 5 days after the treatment samples are checked for mortality. The following compounds showed at least 80% control at 50 ppm: A3

Nilaparvata lugens (Brown plant hopper)

Rice seedlings are treated with the diluted test solutions in a spray chamber. After drying, plants are infested with 20 N₃ nymphs (2 replicates). 6-12 days after the treatment samples are checked for mortality.

The following compounds showed at least 80% control at 50 ppm: A01, A02, A03, A04, A06, A07, A08, A10, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23

The following compounds showed at least 80% control at 200 ppm: A01, A02, A03, A04, A06, A07, A08, A10, Al l, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, B01, B02, B03, B04, B05, B06, B07, B08, B09, B10, Bl l, B12, B13, B14, B15, B16, B17, B18, B19, B20, B21 , B22, B23, B24, B25, B26, B27, B28, B29, B30, B31 , B32, B33, B34, B35, B36, B37

Chilo suppressalis (Rice stem borer)

Rice seedlings are treated and after drying the leaves are cut and transferred into a petri dish coated with wet filter paper. 10 larvae (L2) are added and the dish is covered with a filter tissue and a plastic lid. 5 days after treatment the percentage mortality is assessed (3 replicates per concentration).

The following compounds showed at least 80%> control at 0.8 ppm: A23, Bl l, B26, B38 (other than the compounds below no additional compounds were tested). Examples

The data in the comparative Examples below were obtained using the methods described above. The results show that the compounds of the invention are significantly more active against the indicated rice pests than structurally similar compounds, particularly at low rates of application.

Comparative Table 1

Comparative Table 2

Comparative Table 3

/ ppm %

Compound of the invention Chilo suppressalis (Rice stem 0.8 100 borer) 0.2 97

Reference compound Chilo suppressalis (Rice stem 0.8 60

borer)

0.2 23

Comparative Table 4

Compound of the invention Reference compound

Compound Test Application rate Control /

/ ppm %

Compound of the invention Chilo suppressalis (Rice stem 0.8 100 borer) 0.2 97

Reference compound Chilo suppressalis (Rice stem 0.8 80

borer)

0.2 40

Comparative Table 5

Comparative Table 6

Compound of the invention Reference compound

Compound Test Application rate Control /

/ ppm %

Compound of the invention Nilaparvata lugens (Brown 50 79

plant hopper) 25 44

Reference compound Nilaparvata lugens (Brown 50 0

plant hopper)

25 0

Comparative Table 7

Comparative Table 8

plant hopper) 25 0

Comparative Table 9

Compound of the invention Reference compound

Compound Test Application rate Control /

/ ppm %

Compound of the invention Nilaparvata lugens (Brown 50 80

plant hopper) 25 30

Reference compound Nilaparvata lugens (Brown 50 0

plant hopper)

25 0

Comparative Table 10

Compound of the invention Reference compound

Compound Test Application rate Control /

/ ppm %

Compound of the invention Nilaparvata lugens (Brown 50 45

plant hopper)

25 15

Reference compound Nilaparvata lugens (Brown 50 30

plant hopper)

25 0

Claims

1. A method comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I

wherein

cycle A is Ala or A2a

A1 a A2a

cycle B is Bl

cycle C is phenyl;

R⁵ is chloro, bromo, CF₃ or methyl;

R⁷ is chlorodifluoromethyl or trifluoromethyl;

each R⁸ is independently bromo, chloro, fluoro or trifluoromethyl;

p is 1, 2 or 3; and

and X is selected from PI to P9

2. A method according to claim 1 , wherein the method is a method of controlling and/or preventing infestation stemborer in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I as defined in claim 1.

3. A method of controlling and/or preventing infestation of stemborer in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula I as defined in claim 1.

4. A method according to claim 1, wherein the method is a method of controlling and/or preventing infestation leaffolder in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I as defined in claim 1.

5. A method of controlling and/or preventing infestation of leaffolder in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula I as defined in claim 1.

6. A method according to claim 1 , wherein the method is a method of controlling and/or preventing infestation hoppers in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I as defined in claim 1.

7. A method of controlling and/or preventing infestation of hoppers in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula I as defined in claim 1.

8. A method according to claim 1 , wherein the method is a method of controlling and/or preventing infestation gallmidge in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I as defined in claim 1.

9. A method of controlling and/or preventing infestation of gall midge in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula I as defined in claim 1.

5 10. A method according to claim 1 , wherein the method is a method of controlling and/or preventing infestation whorl maggot in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I as defined in claim 1.

11. A method of controlling and/or preventing infestation of whorl maggot in a crop of useful plants 10 comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a

compound of formula I as defined in claim 1.

12. A method according to claim 1 , wherein the method is a method of controlling and/or preventing infestation Rice bugs in rice comprising applying to a crop of rice plants, the locus thereof, or propagation

15 material thereof, a compound of formula I as defined in claim 1.

13. A method of controlling and/or preventing infestation of Rice bugs in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula I as defined in claim 1.

20

14. A method according to claim 1 , wherein the method is a method of controlling and/or preventing infestation Black bugs in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula I as defined in claim 1.

25 15. A method of controlling and/or preventing infestation of Black bugs in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula I as defined in claim 1.

16. A method or use of a compound of formula I according to any one of claims 1 to 15, wherein the 30 compound of formula I is a mixture of the compound of formula I* and the compound of formula I**

I^* ** wherein the substituents are as defined in claim 1 , and wherein said mixture is enriched for the compound of formula I**.

17. A method or use according to any one of claims 1 to 16, wherein X is P2, P3 or P4.

18. A method or use according to any one of claims 1 to 17, wherein cycle A is cycle Al a.

19. A method for obtaining regulatory approval for the use of one or more of a compound of formula I as defined in any one of claims 1 and 16 to 18 to control insects selected from the group consisting of stemborer, leaffolder, hoppers, Gall midge, whorl maggot, Rice bugs, and Black bugs, comprising at least one step of referring to, submitting or relying on biological data showing that said active ingredient reduces insect pressure.

20. A method comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula A

G¹ is oxygen;

R¹ is hydrogen;

L is a bond, methylene or ethylene;

one of A¹ and A² is S, SO or S0₂ and the other is -C(R⁴)R⁴-;

R³ is hydrogen;

each R⁴ is independently hydrogen;

Y¹, Y² and Y³ are independently CH or nitrogen;

wherein no more than two of Y¹, Y² and Y³ are nitrogen and wherein Y² and Y³ are not both nitrogen; R⁵ is chloro, bromo, fluoro;

X² is C-X⁶ or nitrogen;

X⁴ is trifluoromethyl, difluoromethyl or chlorodifluoromethyl; or a compound of formula A'

wherein

G¹ is oxygen;

R¹ is hydrogen;

R² is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l -dioxo-thietan-3-yl-, thietan-3-ylmethyl-, l-oxo-thietan-3- ylmethyl-, or l,l -dioxo-thietan-3-ylmethyl-;

Y¹, Y² and Y³ are independently CH or nitrogen;

C₂halocycloalkyl, Ci-C₂alkoxy, Ci-C₂haloalkoxy;

X² is C-X⁶;

Χ', Χ³ and X⁶ are independently halogen or trihalomethyl;

X⁴ is trifluoromethyl, difluoromethyl or chlorodifluoromethyl; or a compound of formula A"

wherein G¹ is oxygen;

R¹ is hydrogen;

R² is thietan-3-ylmethyl-, l -oxo-thietan-3-ylmethyl-, l,l -dioxo-thietan-3-ylmethyl-;

Y¹, Y² and Y³ are independently CH or nitrogen;

5 wherein no more than two of Y¹, Y² and Y³ are nitrogen and wherein Y² and Y³ are not both nitrogen; R⁵ is hydrogen, halogen, cyano, nitro, NH₂, Ci-C₂alkyl, Ci-C₂haloalkyl, C3-C₅cycloalkyl, d- C₂halocycloalkyl, Ci-C₂alkoxy, Ci-C₂haloalkoxy;

X² is C-X⁶ or nitrogen;

Χ', Χ³ and X⁶ are independently hydrogen, halogen or trihalomethyl, wherein at least two of X¹, X³ and 10 X⁶ are not hydrogen;

X⁴ is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.

21. A method according to claim 20, wherein the method is a method of controlling and/or preventing infestation of hoppers in rice comprising applying to a crop of rice plants, the locus thereof, or

15 propagation material thereof, a compound of formula A, A' or A" .

22. A method of controlling and/or preventing infestation of hoppers in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A" as defined in claim 20.

20

23. A method according to claim 20, wherein the method is a method of controlling and/or preventing infestation of stemborer in rice comprising applying to a crop of rice plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A".

25 24. A method of controlling and/or preventing infestation of stemborer in a crop of useful plants comprising applying to a crop of useful plants, the locus thereof, or propagation material thereof, a compound of formula A, A' or A' ' as defined in claim 20.