Dihydrofuran derivatives as insecticidal compounds

Patent metadata

Field	Value
Publication number	US-9714228-B2
Application number	US-201113580626-A
Country	US
Kind code	B2
Filing date	Jan 31, 2011
Priority date	Feb 22, 2010
Publication date	Jul 25, 2017
Grant date	Jul 25, 2017

Abstract

The present invention relates to compounds of formula (I) wherein Q is Q1 or Q2 P is P1, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A 1 , A 2 , A 3 , A 4 , G 1 , Y 1 , Z, 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)

wherein
Q is Q1 or Q2

P is P1, pyrazolyl, triazolyl, or pyrazolyl substituted by one to five Z, or triazolyl substituted by one to five Z;

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;
G 1 is oxygen or sulfur;
Y 1 is CH 2 or C═O;
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 C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to five R 6 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 7 , aryl-C 1 -C 4 alkylene- or aryl-C 1 -C 4 alkylene- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-C 1 -C 4 alkylene- or heterocyclyl-C 1 -C 4 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , C 1 -C 8 alkylaminocarbonyl-C 1 -C 4 alkylene, C 1 -C 8 haloalkylaminocarbonyl-C 1 -C 4 alkylene, C 3 -C 8 cycloalkyl-aminocarbonyl-C 1 -C 4 alkylene, C 1 -C 6 alkyl-O—N═CH—, C 1 -C 6 haloalkyl-O—N═CH—,
R 3 is C 1 -C 8 haloalkyl;
R 4 is phenyl or phenyl substituted by one to five R 9 ;
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-;
each R 6 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, C 1 -C 8 alkoxy-, C 1 -C 8 haloalkoxy-, aryloxy or aryloxy substituted by one to five R 10 , aryloxy-C 1 -C 4 alkylene or aryloxy-C 1 -C 4 alkylene wherein the aryl moiety is substituted by one to five R 10 , 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 10 ;
each R 7 is independently halogen, C 1 -C 8 alkyl, C 1 -C 8 alkenyl, C 1 -C 8 alkynyl, C 1 -C 8 alkyl-O—N═, C 1 -C 8 haloalkyl-O—N═; C 1 -C 8 alkoxy, C 1 -C 8 akoxycarbonyl;
each R 8 is independently halogen, cyano, nitro, oxo, 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 8 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 alkoxycarbonyl-, aryl or aryl substituted by one to five R 10 , heterocyclyl or heterocyclyl substituted by one to five R 10 , aryl-C 1 -C 4 alkylene or aryl-C 1 -C 4 alkylene wherein the aryl moiety is substituted by one to five R 10 , heterocyclyl-C 1 -C 4 alkylene or heterocyclyl-C 1 -C 4 alkylene wherein the heterocyclyl moiety is substituted by one to five R 10 , aryloxy or aryloxy substituted by one to five R 10 , aryloxy-C 1 -C 4 alkylene or aryloxy-C 1 -C 4 alkylene wherein the aryl moiety is substituted by one to five R 10 ;
each R 9 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 10 , or heterocyclyl or heterocyclyl substituted by one to five R 10 ;
each R 10 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-;
each Z is independently halogen, C 1 -C 12 alkyl or C 1 -C 12 alkyl substituted by one to five R 6 , nitro, C 1 -C 12 alkoxy or C 1 -C 12 alkoxy substituted by one to five R 6 , cyano, C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, C 1 -C 12 haloalkylsulfinyl, C 1 -C 12 haloalkylsulfonyl, hydroxyl or thiol;
or a salt or N-oxide thereof.

2. A compound according to claim 1 wherein G 1 is oxygen.

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

4. A compound according to claim 1 wherein R 2 is C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to five R 6 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 7 , aryl-C 1 -C 4 alkylene- or aryl-C 1 -C 4 alkylene- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-C 1 -C 4 alkylene- or heterocyclyl-C 1 -C 4 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , C 1 -C 8 alkylaminocarbonyl-C 1 -C 4 alkylene, C 1 -C 8 haloalkylaminocarbonyl-C 1 -C 4 alkylene, C 3 -C 8 cycloalkyl-aminocarbonyl-C 1 -C 4 alkylene, or group A

R 11 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl-methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R 12 , or R 11 is pyridyl-methyl- or pyridyl-methyl-substituted by one to three R 12 ;
each R 12 is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy;
wherein each aryl group is a phenyl group and each heterocyclyl group is independently selected from pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrahydrothiophenyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl, benzothiazolyl, oxetanyl, thietanyl, oxo-thietanyl, dioxo-thietanyl, pyrrolidinyl, tetrahydrofuranyl, [1,3]dioxolanyl, piperidinyl, piperazinyl, [1,4]dioxanyl, and morpholinyl, 2,3-dihydro-benzofuranyl, benzo[1,3]dioxolanyl, and 2,3-dihydro-benzo[1,4]dioxinyl.

5. A compound according to claim 4 wherein R 2 is C 1 -C 8 alkyl or C 1 -C 8 alkyl substituted by one to five R 6 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 7 , phenyl-C 1 -C 4 alkylene- or phenyl-C 1 -C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-C 1 -C 4 alkylene- or pyridyl-C 1 -C 4 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , oxetanyl or oxetanyl substituted by one to five R 8 , thietanyl-C 1 -C 4 alkylene or thietanyl-C 1 -C 4 alkylene wherein the thietanyl moiety is substituted by one to five R 8 , oxo-thietanyl-C 1 -C 4 alkylene or ox

Assignees

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

Inventors

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

Classifications

• C07D307/28 Primary

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

• C07D307/58

  One oxygen atom, e.g. butenolide · CPC title

• C07D405/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D307/52

  Radicals substituted by nitrogen atoms not forming part of a nitro radical · CPC title

• C07D405/04

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