Insecticidal compounds

Patent metadata

Field	Value
Publication number	US-10364235-B2
Application number	US-201715810438-A
Country	US
Kind code	B2
Filing date	Nov 13, 2017
Priority date	Jun 22, 2009
Publication date	Jul 30, 2019
Grant date	Jul 30, 2019

Abstract

The invention relates to compounds of formula (I):

where A 1 , A 2 , A 3 , A 4 , G, R 1 , R 2 , R 3 and R 4 are as defined in claim 1 ; or a salt or N-oxide thereof.

Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.

First claim

The invention claimed is:

1. A compound of formula (I)

where
A 1 , A 2 , A 3 and A 4 are independently of each other C—H, C—R 5 or nitrogen;
wherein no more than one of A 1 , A 2 , A 3 and A 4 is nitrogen, and
wherein no more than two of A 1 , A 2 , A 3 and A 4 is C—R 5 ;

G is oxygen or sulfur;
R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy-, C 1 -C 8 alkylcarbonyl- or C 1 -C 8 alkoxycarbonyl-;
R 2 is a group of formula (II)

where
L is a single bond or C 1 -C 6 alkylene; and
Y 1 , Y 2 and Y 3 are independently of another CR 8 R 9 , C═O, C═N—OR 10 , N—R 10 , S, SO, SO 2 , S═N—R 10 or SO═N—R 10 , provided that at least one of Y 1 , Y 2 or Y 3 is not CR 8 R 9 , C═O or C═N—OR 10 ;
R 3 is C 1 -C 8 haloalkyl;
R 4 is aryl or aryl substituted by one to five R 7 , or heteroaryl or heteroaryl substituted by one to five R 7 ;
each R 5 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkenyl, C 1 -C 8 haloalkenyl, C 1 -C 8 alkynyl, C 1 -C 8 haloalkynyl, C 3 -C 10 cycloalkyl, C 1 -C 8 alkoxy-, C 1 -C 8 haloalkoxy-, C 1 -C 8 alkylthio-, C 1 -C 8 haloalkylthio-, C 1 -C 8 alkylsulfinyl-, C 1 -C 8 haloalkylsulfinyl-, C 1 -C 8 alkylsulfonyl- or C 1 -C 8 haloalkylsulfonyl-, or
two R 5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge;
R 6 is hydrogen or C 1 -C 8 alkyl;
each R 7 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, hydroxy, C 1 -C 8 alkoxy-, C 1 -C 8 haloalkoxy-, mercapto, C 1 -C 8 alkylthio-, C 1 -C 8 haloalkylthio-, C 1 -C 8 alkylsulfinyl-, C 1 -C 8 haloalkylsulfinyl-, C 1 -C 8 alkylsulfonyl-, C 1 -C 8 haloalkylsulfonyl-, C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxycarbonyl-, aryl or aryl substituted by one to five R 11 , or heterocyclyl or heterocyclyl substituted by one to five R 11 ;
each R 8 and R 9 is independently hydrogen, halogen, C 1 -C 8 alkyl or C 1 -C 8 haloalkyl;
each R 10 is independently hydrogen, cyano, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkylcarbonyl-, 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 12 , 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 12 ;
each R 11 and R 12 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. The compound according to claim 1 , wherein A 1 is C—R 5 , A 2 is C—H, A 3 is C—H or nitrogen and A 4 is C—H or nitrogen.

3. The compound according to claim 1 , wherein G is oxygen.

4. The compound according to claim 1 , wherein R 1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-.

5. The compound according to claim 1 , wherein R 2 is a group of formula (IIc)

where
R 13 is C 1 -C 8 alkyl,
m is 0, 1, 2, 3, 4, or 5, and
Y 2 is S, SO, SO 2 , S═N—R 10 , SO═N—R 10 or C═N—OR 10 .

6. The compound according to claim 1 , wherein R 3 is chlorodifluoro-methyl or trifluoromethyl.

7. The compound according to claim 1 , wherein R 4 is phenyl or phenyl substituted by one to five R 7 .

8. The compound according to claim 1 , wherein
A 1 , A 2 , A 3 and A 4 are independently of each other C—H or C—R 5 ;
G is oxygen;
R 1 is hydrogen, methyl or ethyl;
R 2 is a group of formula (IIb)

where
L is a single bond, methylene ethylene or propylene;
one of Y 1 and Y 2 is S, SO, SO 2 , S═N—R 10 , SO═N—R 10 or C═N—OR 10 and the other is CH 2 ;
R 3 is chlorodifluoromethyl or trifluoromethyl;
R 4 is 3,5-dibromo-phenyl-, 3,5-dichloro-phenyl-, 3,5-bis-(trifluoromethyl)-phenyl-, 3,4-dichloro-phenyl-, 3,4,5-trichloro-phenyl- or 3-trifluoromethyl-phenyl-;
each R 5 is independently bromo, chloro, fluoro, methyl, trifluoromethyl or vinyl, or two R 5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge;
each R 10 is independently methyl or hydrogen; and
R 13 is hydrogen or C 1 -C 8 alkyl.

9. The compound according to claim 1 , wherein
A 1 , A 2 , A 3 and A 4 are independently of each other C—H or C—R 5 ;
G is oxygen;
R 1 is hydrogen;
R 2 is a group of formula (IIc)

where
m is 0, 1, 2, 3, 4, or 5, and
Y 2 is S, SO, SO 2 , or C═N—OR 10 ;
R 3 is chlorodifluoromethyl or trifluoromethyl;
R 4 is 3,5-dibromo-phenyl-, 3,5-dichloro-phenyl-, 3,5-bis-(trifluoromethyl)-phenyl-, 3,4-dichloro-phenyl-, 3,4,5-trichloro-phenyl- or 3-trifluoromethyl-phenyl-;
each R 5 is independently bromo, chloro, fluoro, methyl, trifluoromethyl or vinyl, or two R 5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge;
each R 10 is independently methyl or hydrogen; and
R 13 is methyl.

10. The compound according to claim 2 , wherein A 1 is C—R 5 , A 2 is C—H, A 3 is C—H, and A 4 is C—H.

Assignees

• Syngenta Crop Protection Llc
• Syngenta Ltd
• Synenta Crop Prot Llc

Inventors

• Renold Peter
• Cassayre Jerome Yves
• El Qacemi Myriem
• Pabba Jagadish
• Pitterna Thomas

Classifications

• C07F7/0812

  comprising a heterocyclic ring · CPC title

• C07D409/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D207/20

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• A01N43/36

  five-membered rings · CPC title

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title