Dihydrobenzofuran derivatives as insecticidal compounds

Patent metadata

Field	Value
Publication number	US-9598389-B2
Application number	US-201414771600-A
Country	US
Kind code	B2
Filing date	Mar 6, 2014
Priority date	Mar 6, 2013
Publication date	Mar 21, 2017
Grant date	Mar 21, 2017

Abstract

Provided are compounds of formula (I) and methods of 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).

First claim

The invention claimed is:

1. A compound of formula I

wherein
G 1 is oxygen or sulfur;
Y 1 is oxygen, sulfur, C(O), CHOR or CH 2 ;
Y 2 , Y 3 and Y 4 are each independently C—H, C—R 5 or nitrogen, wherein no more than one of Y 2 , Y 3 and Y 4 is C—R 5 ;
Y 5 is C—H, C—F or nitrogen;
Y 6 is C—H, C—R 6a or nitrogen;
Y 7 is C—H, C—R 6b or nitrogen;
Y 8 is C—H, C—R 6c or nitrogen;
R is hydrogen, C 1 -C 8 alkyl;
R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylcarbonyl, O 3 —C 8 cycloalkylcarbonyl or C 1 -C 8 alkoxycarbonyl;
R 2 is C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to five R 7 , C 2 -C 8 alkenyl or C 2 -C 8 alkenyl substituted by one to five R 7 , C 2 -C 8 alkynyl or C 2 -C 8 alkynyl substituted by one to five R 7 , C 1 -C 8 alkoxy-C 1 -C 8 alkyl or C 1 -C 8 alkoxy-C 1 -C 8 alkyl substituted by one to five R 7 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 8 , C 3 -C 10 cycloalkyl-C 1 -C 4 alkylene or C 3 -C 10 cycloalkyl-C 1 -C 4 alkylene substituted by one to five R 8 , aryl-C 1 -C 4 alkylene- or aryl-C 1 -C 4 alkylene- substituted by one to five R 9 , heterocyclyl-C 1 -C 4 alkylene- or heterocyclyl-C 1 -C 4 alkylene- substituted by one to five R 9 , aryl or aryl substituted by one to five R 9 , heterocyclyl or heterocyclyl substituted by one to five R 9 ;

or R 1 and R 2 form a four to six membered ring together with the atoms to which they are attached substituted by one to five R 7
R 3 is C 1 -C 8 haloalkyl;
R 4 is aryl or aryl substituted by one to five R 10 , or heteroaryl or heteroaryl substituted by one to five R 10 ;
each R 5 is independently halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R 6a is halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R 6b is fluoro or chloro;
R 6c is halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
each R 7 is independently halogen, cyano, nitro, hydroxy, amino, C 1 -C 8 alkylamino, (C 1 -C 8 alkyl) 2 amino, C 1 -C 8 alkylcarbonylamino, C 1 -C 8 haloalkylcarbonylamino, carbonylamino, (carbonyl)(C 1 -C 8 alkyl)amino, (C 1 -C 8 alkylcarbonyl)(C 1 -C 8 alkyl)amino, (C 1 -C 8 haloalkylcarbonyl)(C 1 -C 8 alkyl)amino, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 alkylcarbonyl, C 1 -C 8 alkoxycarbonyl, 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, aryl-C 1 -C 4 alkylthio or aryl-C 1 -C 4 alkylthio wherein the aryl moiety is substituted by one to five R 11 , or R 7 is OH—N═ or C 1 -C 6 alkoxy-N═;
each R 8 is independently halogen, cyano, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 alkoxy, or C 1 -C 8 akoxycarbonyl;
each R 9 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 cyanoalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 5 haloalkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkyl-C 1 -C 4 alkylene, 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 alkylaminosulfonyl, (C 1 -C 8 alkyl) 2 aminosulfonyl, C 1 -C 8 alkylcarbonyl, C 1 -C 8 haloalkylcarbonyl, C 1 -C 8 alkoxycarbonyl, C 1 -C 8 haloalkoxycarbonyl;
each R 10 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, or C 1 -C 8 alkoxycarbonyl;
each R 11 is independently halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, or C 1 -C 4 haloalkoxy;
or a salt or N-oxide thereof.

2. A compound according to claim 1 , wherein Y 1 is oxygen.

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

4. A compound according to claim 1 , wherein Y 2 and Y 4 are C—H, and Y 3 is C—H or C—R 5 .

5. A compound according to claim 4 , wherein R 5 is halogen, cyano, methyl, halomethyl, methoxy or halomethoxy.

6. A compound according to claim 1 , wherein Y 5 , Y 7 and Y 8 are C—H or nitrogen and Y 6 is C—H, C—R 6a or nitrogen, wherein no more than two of Y 5 , Y 6 , Y 7 and Y 8 are nitrogen.

7. A compound according to claim 6 , wherein R 6a is halogen, cyano, methyl, halomethyl, methoxy or halomethoxy.

8. A compound according to claim 1 , wherein R 2 is C 1 -C 6 alkyl or C 1 -C 6 alkyl substituted by one to five R 7 , C 2 -C 6 alkenyl or C 2 -C 6 alkenyl substituted by one to five R 12 , C 2 -C 6 alkynyl or C 2 -C 6 alkynyl substituted by one to five R 7 , C 1 -C 6 alkoxy-C 1 -C 6 alkyl or C 1 -C 6 alkoxy-C 1 -C 6 alkyl substituted by one to five R 7 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 8 , C 3 -C 10 cycloalkyl-C(R 12 )(R 13 )— or C 3 -C 10 cycloalkyl-C(R 12 )(R 13 )— substituted by one to five R 9 , aryl-C(R 12 )(R 13 )— or aryl-C(R 12 )(R 13 )— substituted by one to five R 9 , heterocyclyl-C(R 12 )(R 13 )— or heterocyclyl-C(R 12 )(R 13 )— substituted by one to five R 9 , aryl or aryl substituted by one to five R 9 , heterocyclyl or heterocyclyl substituted by one to five R 9 ;
wherein aryl is phenyl;
wherein heterocyclyl is a 4- to 7-membered heterocyclic ring containing one to four heteroatoms independently selected from O, S, SO, SO 2 , N and N(R 14 ) as ring atoms; and
wherein R 12 and R 13 are independently hydrogen, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 3 -C 6 cycloalkyl;
wherein R 14 is hydrogen or R 9 .

9. A compound according to claim 1 , wherein R 3 is chlorodifluoromethyl, difluoromethyl or trifluoromethyl.

10. A compound according to claim 1 , wherein R 4 is group A

wherein X 2 is C—X 4 or nitrogen and X 1 , X 3 and X 4 are independently hydrogen, halogen or trihalomethyl, providing that at least one of X 1 , X 3 and X 4 is not hydrogen, wherein # is the attachment point.

11. 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 .

12. An insecticidal, acaricidal, nematicidal or molluscicidal composition according to claim 11 comprising at least one additional compound having biological activity.

13. A combination product comprising a pesticidally effective amount of a component A and a pesticidally effective amount of component B, wherein component A is a compound of formula (I) as defined in claim 1 , and compound B is imidacloprid, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, fipronil, ivermectin, omeprazole, tiamulin, benazepril, milbemycin, cyromazine, thiamethoxam, pyriprole, deltamethrin, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, metaflumizone, moxidectin, methoprene, clorsulon, pyrantel, amitraz, triclabendazole, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, nemadectin, albendazo

Assignees

• Syngenta Participations Ag

Inventors

• Lu Long
• Cassayre Jerome Yves
• Luksch Torsten
• El Qacemi Myriem
• Berthon Guillaume
• Wu Yaming

Classifications

• C07D307/79 Primary

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

• C07D333/54

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

• A01N43/54

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title

• C07D405/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07C233/25

  having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton · CPC title