Insecticidal compounds

Patent metadata

Field	Value
Publication number	US-9913471-B2
Application number	US-201615361838-A
Country	US
Kind code	B2
Filing date	Nov 28, 2016
Priority date	May 31, 2011
Publication date	Mar 13, 2018
Grant date	Mar 13, 2018

Abstract

The present invention provides compounds of formula (I):

wherein
A 1 , A 2 , A 3 and A 4 are independently of one another C—H, C—R 5 , or nitrogen;
B 1 —B 2 —B 3 —B 4 is —CH 2 —C═N—CH 2 —, —CH 2 —N—CH 2 —CH 2 —, —CH 2 —C═CH—O— or —CH═C—CH 2 —O—;
G 1 is oxygen or sulfur;
L is a single bond or C 1 -C 8 alkylene;
R 1 is hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkylcarbonyl-, C 1 -C 8 alkoxy, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, aryl or aryl substituted by one to three R 6 , or R 1 is heterocyclyl or heterocyclyl substituted by one to three R 6 or C 1 -C 8 alkoxycarbonyl-;
R 2 is hydrogen, C 1 -C 8 haloalkyl 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 R 4 is heterocyclyl or heterocyclyl substituted by one to three R 6 ;
Y 1 is CR 7 R 8 , C═O or C═S;
Y 2 , Y 3 and Y 4 are independently CR 7 R 8 , C═O, C═S, N—R 9 , O, S, SO or SO 2 ;
wherein at least two adjacent ring atoms in the ring formed by Y 1 , Y 2 , Y 3 and Y 4 are heteroatoms;
each R 7 and R 8 is independently hydrogen, halogen, C 1 -C 8 alkyl, or C 1 -C 8 haloalkyl;
and R 5 , R 6 , R 7 , R 8 and R 9 are as defined in the claims.

The invention also relates to processes and intermediates for preparing these compounds, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these compounds and to methods of using these compounds to control insect, acarine, nematode and mollusc pests.

First claim

The invention claimed is:

1. A compound of formula (I):

wherein
A 1 is C—R 5 ;
A 2 , A 3 and A 4 are each C—H;
B 1 —B 2 —B 3 —B 4 is —CH 2 —N—CH 2 —CH 2 —;
G 1 is oxygen;
L is a single bond;
R 1 is hydrogen;
R 2 is hydrogen;
R 3 is trifluoromethyl;
R 4 is 3,5-dichlorophenyl-;
each R 5 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, 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, C 1 -C 8 alkoxycarbonyl-, or two R 5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge;
Y 1 is C═O;
Y 2 is N—R 9 ;
Y 3 is O; and
Y 4 is CR 7 R 8 ;
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, cyano-C 1 -C 8 alkyl, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO 2 , or C 3 -C 8 cycloalkyl-C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl-C 1 -C 8 alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO 2 , or C 3 -C 8 cycloalkyl-C 1 -C 8 haloalkyl, C 1 -C 8 hydroxyalkyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, phenyl, phenyl substituted by one to three R 10 , heteroaryl, heteroaryl substituted by one to three R 10 , phenyl-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl wherein the phenyl moiety is substituted by one to three R 10 , heteroaryl-C 1 -C 4 alkyl or heteroaryl-C 1 -C 4 alkyl wherein the heteroaryl moiety is substituted by one to three R 10 , or C 1 -C 4 alkyl-(C 1 -C 4 alkyl-O—N═)C—CH 2 —;
each R 10 is independently halogen, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, or C 1 -C 8 haloalkoxy; or a salt or N-oxide thereof.

2. The compound according to claim 1 , wherein R 5 is halogen, nitro, C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, C 2 -C 4 alkenyl or C 1 -C 4 haloalkyl.

3. The compound according to claim 1 , wherein each R 5 independently is bromo, chloro, fluoro, cyclopropyl, trifluoromethyl, vinyl, or methyl.

4. The compound according to claim 1 , wherein each R 9 is independently hydrogen, cyano-C 1 -C 8 alkyl, C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO 2 , or C 1 -C 8 haloalkyl, C 1 -C 8 hydroxyalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl-C 1 -C 4 alkyl or phenyl-C 1 -C 4 alkyl wherein the phenyl moiety is substituted by one to three R 10 , 5-6 membered heteroaryl-C 1 -C 4 alkyl or 5-6 membered heteroaryl-C 1 -C 4 alkyl wherein the heteroaryl moiety is substituted by one to three R 10 , and wherein the heteroaryl is pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl or thiazolyl.

5. The compound according to claim 1 , wherein each R 9 is independently hydrogen, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, phenyl-CH 2 -alkyl- or phenyl-CH 2 — wherein the phenyl moiety is substituted by one to three R 10 , furanyl or furanyl substituted by one to three R 10 , thietanyl, oxetanyl, oxo-thietanyl, or dioxo-thietanyl.

6. A method of combating an invertebrate animal pest which comprises applying to the pest, to a locus of the pest, or to a plant susceptible to attack by the pest a pesticidally effective amount of a compound of formula (I) as defined in claim 1 .

7. A composition comprising a pesticidally effective amount of a compound of formula (I) as defined in claim 1 optionally comprising an additional pesticidally active ingredient.

8. 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 component 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 (including S-methoprene), clorsulon, pyrantel, amitraz, triclabendazole, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel, triclabendazole, epsiprantel, fipronil, lufenuron, ecdysone or tebufenozide.

Assignees

• Syngenta Participations Ag

Inventors

• Cassayre Jerome Yves
• Renold Peter
• El Qacemi Myriem
• Pitterna Thomas
• Toueg Julie Clementine

Classifications

• C07D413/14

  containing three or more hetero rings · CPC title

• A01N43/80 Primary

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• C07D411/12

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

• C07D413/12 Primary

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

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title