Insecticidal compounds
A compound of Formula (I): where A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , G 1 , L, R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 and Y 3 are as defined in claim 1 ; or a sail or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising compounds of formula (I) and to methods of using compounds of formula (I) to combat and control insect, acarine, mollusc and nematode pests.
1. A compound of formula (I)
where
A 1 , A 2 , A 3 , A 4 , A 5 , and A 6 are independently of another C—H, C—R 5 , or nitrogen;
G 1 is oxygen or sulfur;
L is a single bond, or C 1 -C 6 alkylene;
R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl-, or C 1 -C 8 alkoxycarbonyl-;
R 2 is hydrogen, or C 1 -C 8 alkyl;
R 3 is C 1 -C 8 haloalkyl;
R 4 is aryl or aryl substituted by one to three R 6 , or heteroaryl or heteroaryl substituted by one to three R 6 ;
Y 1 , Y 2 and Y 3 are independently of another CR 7 R 8 , C═O, C═N—OR 9 , N-R 9 , O, S, SO, SO 2 , S═N-R 9 , or SO═N-R 9 , provided that at least one of Y 1 , Y 2 or Y 3 is not CR 7 R 8 ;
each R 5 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, or C 1 -C 8 alkoxycarbonyl-, aryl or aryl optionally substituted by one to three R 10 , or heteroaryl or heteroaryl optionally substituted by one to three R 10 ;
each R 6 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, or C 1 -C 8 alkoxycarbonyl-;
each R 7 and R 8 is independently hydrogen, halogen, C 1 -C 8 alkyl, or C 1 -C 8 haloalkyl;
each R 9 is independently hydrogen, cyano, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkyl-carbonyl-, C 1 -C 8 haloalkylcarbonyl,- C 1 -C 8 alkoxycarbonyl-, C 1 -C 8 haloalkoxycarbonyl-, C 1 -C 8 alkylsulfonyl-, C 1 -C 8 haloalkylsulfonyl-, aryl-C 1 -C 4 alkylene- or aryl-C 1 -C 4 alkylene- where the aryl moiety is substituted by one to three R 11 , or heteroaryl-C 1 -C 4 alkylene- or heteroaryl-C 1 -C 4 alkylene- where the heteroaryl moiety is substituted by one to three R 11 ; and
each R 10 and R 11 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, or C 1 -C 8 alkoxycarbonyl-; or a salt or N-oxide thereof.
2. A compound according to claim 1 where A 1 , A 2 , A 3 , A 4 , A 5 , and A 6 are independently of each other C—H or C—R 5 .
3. A compound according to claim 1 where G 1 is oxygen.
4. A compound according to claim 1 where L is a single bond.
5. A compound according to claim 1 where R 1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-.
6. A compound according to claim 1 where R 2 is hydrogen or methyl.
7. A compound according to claim 1 where R 3 is chlorodifluoromethyl or trifluoromethyl.
8. A compound according to claim 1 where R 4 is aryl or aryl substituted by one to three R 6 .
9. A compound according to claim 1 where Y 1 , Y 2 and Y 3 are independently of another CR 7 R 8 , N—R 9 , O, S, SO, SO 2 , S═N—R 9 , or SO═N—R 9 , provided that one of Y 1 , Y 2 or Y 3 is not CR 7 R 8 .
10. A compound according to claim 1 where Y 2 is C═O, C═N—OR 9 , N—R 9 , O, S, SO, SO 2 , S═N—R 9 , or SO═N—R 9 , and Y 1 and Y 3 are independently of another CR 7 R 8 .
11. A compound according to claim 1 where Y 2 is O, S, SO, SO 2 , S═N—R 9 , or SO═N—R 9 , and Y 1 and Y 3 are independently of another CR 7 R 8 .
12. A compound according to claim 1 , wherein
each R 5 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, or C 1 -C 8 alkoxycarbonyl-;
each R 6 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, or methoxycarbonyl-;
each R 7 and R 8 is independently hydrogen or methyl;
each R 9 is independently hydrogen, cyano, methyl, trifluoromethyl, methylcarbonyl-, trifluoromethylcarbonyl-, methoxycarbonyl-, trifluoromethoxycarbonyl-, methylsulfonyl-, trifluoromethylsulfonyl-, or benzyl or benzyl where the phenyl moiety is substituted by one to three R 10 ;
each R 10 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, or methoxycarbonyl-; and
each R 11 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, or methoxycarbonyl-.
13. A compound according to claim 1 , wherein the compound is a compound of formula (I′)
wherein
A 1 , A 2 , A 3 , A 4 , A 5 , and A 6 are independently of one another C—H or C—R 5 ;
L is a single bond;
Y 1 , Y 2 and Y 3 are independently of one another O, S, SO or SO 2 , or CR 7 R 8 , provided that at least two of Y 1 , Y 2 and Y 3 are CR 7 R 8 ;
R 1 is hydrogen, methyl, or ethyl;
R 2 is hydrogen or methyl;
R 3 is chlorodifluoromethyl or trifluoromethyl;
R 5 , R 7 , R 8 , R 12 and R 13 are independently of one another hydrogen, halogen C 1 -C 4 alkyl or C 1 -C 4 haloalkyl.
14. A compound according to claim 13 , wherein
A 1 , A 2 , A 3 , A 4 , A 5 , and A 6 are independently of one another C—H or C—R 5 ;
L is a single bond;
Y 1 , and Y 3 are independently of one another CR 7 R 8 ;
Y 2 is O, S, SO or SO 2 ;
R 1 is hydrogen;
R 2 is hydrogen or methyl;
R 3 is trifluoromethyl;
R 5 , is hydrogen, halogen or methyl;
R 7 , R 8 are independently of one another hydrogen or methyl;
R 12 and R 13 are independently of one another fluorine, chlorine or bromine.
15. A compound of formula (XI)
where A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , G 1 , L, R 1 , R 2 , Y 1 , Y 2 and Y 3 are as defined in claim 1 ; or a salt or N-oxide thereof; or
a compound of formula (XII)
where A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , G 1 , L, R 1 , R 2 , Y 1 , Y 2 and Y 3 are as defined in claim 1 ; or a salt or N-oxide thereof; or
a compound of formula (XIII)
where A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , G 1 , L, R 1 , R 2 , Y 1 , Y 2 and Y 3 are as defined in claim 1 and X B is a leaving group; or a salt or N-oxide thereof; or
a compound of formula (XIV)
where A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , G 1 , L, R 1 , R 2 , Y 1 , Y 2 and Y 3 are as defined in claim 1 ; or a salt or N-oxide thereof; or
a compound of formula (XV)
where A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , G 1 , L, R 1 , R 2 , Y 1 , Y 2 and Y 3 are as defined in claim 1 ; or a salt or N-oxide thereof.
16. A method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in claim 1 .
17. An insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in claim 1 .