US 10,869,477 B2 · Insecticidal compounds

Abstract

The present invention provides compounds of formula (I): wherein A1, A2, A3 and A4 are independently of one another C—H, C—R5, or nitrogen; B1-B2-B3-B4 is —CH2—C═N—CH2—, —CH2—N—CH2—CH2—, —CH2—C═CH—O— or —CH═C—CH2—O—; G1 is oxygen or sulfur; L is a single bond or C1-C8alkylene; R1 is hydrogen, C1-C8alkyl, C1-C8alkylcarbonyl-, C1-C8alkoxy, C2-C8alkenyl, C2-C8alkynyl, C1-C8alkoxy-C1-C8alkyl, aryl or aryl substituted by one to three R6, or R1 is heterocyclyl or heterocyclyl substituted by one to three R6 or C1-C8alkoxycarbonyl-; R2 is hydrogen, C1-C8haloalkyl or C1-C8alkyl; R3 is C1-C8haloalkyl; R4 is aryl or aryl substituted by one to three R6, or R4 is heterocyclyl or heterocyclyl substituted by one to three R6; Y1 is CR7R8, C—O or C═S; Y2, Y3 and Y4 are independently CR7R8, C═O, C═S, N—R9, O, S, SO or SO2; wherein at least two adjacent ring atoms in the ring formed by Y1, Y2, Y3 and Y4 are heteroatoms; each R7 and R8 is independently hydrogen, halogen, C1-C8alkyl, or C1-C8haloalkyl; and R5, R6, R7, R8 and R9 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.

Claims21

Dependent claims

A compound of formula (I)

wherein
A2, A3, and A4 are independently C—H or N, wherein no more than one of A2, A3, and A4 is N;
B1-B2-B3-B4 is —CH2—C═N—CH2— or —CH2—N—CH2—CH2—;
R5 is hydrogen, halogen, C1-C4alkyl, C3-C4cycloalkyl, C2-C4alkenyl or C1-C4haloalkyl;
each R6 is independently hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, or C1-C4haloalkoxy;
Y1 is C═O, Y2 is N—R9, Y3 is O, and Y4 is CH2;
or
Y1 is CH2, Y2 is S═O, Y3 is O, and Y4 is CH2;
and
each R9 is independently hydrogen, cyano, cyano-C1-C4alkyl, C1-C4alkyl, C1-C4haloalkyl, C3-C8cycloalkyl, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C4alkyl, C3-C8cycloalkyl-C1-C4alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C4haloalkyl, C1-C4hydroxyalkyl, C1-C4alkoxy-C1-C4alkyl, C2-C6alkenyl, C2-C4haloalkenyl, C2-C4alkynyl, C2-C4haloalkynyl, phenyl, phenyl substituted by one to three R10, heteroaryl, heteroaryl substituted by one to three R10, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R10, heteroaryl-C1-C4alkyl or heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R10, or C1-C4alkyl-(C1-C4alkyl-O—N═)C—CH2—;
each R10 is independently halogen, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, or C1-C4haloalkoxy, or a salt or N-oxide thereof.

8 more elements

A compound of formula (I)

wherein
A2, A3, and A4 are independently C—H or N, wherein no more than one of A2, A3, and A4 is N;
B1-B2-B3-B4 is —CH2—C═CH—O— or —CH═C—CH2—O—;
R5 is hydrogen, halogen, nitro, C1-C4alkyl, C3-C4cycloalkyl, C2-C4alkenyl or C1-C4haloalkyl;
each R6 is independently hydrogen, halogen, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, or C1-C4haloalkoxy;
Y1 is C═O, Y2 is N—R9, Y3 is O, and Y4 is CH2;
or
Y1 is CH2, Y2 is S═O, Y3 is O, and Y4 is CH2;
and
each R9 is independently hydrogen, cyano, cyano-C1-C4alkyl, C1-C4alkyl, C1-C4haloalkyl, C3-C8cycloalkyl, C3-C8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C4alkyl, C3-C8cycloalkyl-C1-C4alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO2, or C3-C8cycloalkyl-C1-C4haloalkyl, C1-C4hydroxyalkyl, C1-C4alkoxy-C1-C4alkyl, C2-C4alkenyl, C2-C4haloalkenyl, C2-C4alkynyl, C2-C4haloalkynyl, phenyl, phenyl substituted by one to three R10, heteroaryl, heteroaryl substituted by one to three R10, phenyl-C1-C4alkyl, phenyl-C1-C4alkyl wherein the phenyl moiety is substituted by one to three R10, heteroaryl-C1-C4alkyl or heteroaryl-C1-C4alkyl wherein the heteroaryl moiety is substituted by one to three R10, or C1-C4alkyl-(C1-C4alkyl-O—N═)C—CH2—;
each R10 is independently halogen, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, or C1-C4haloalkoxy, or a salt or N-oxide thereof providing that Y1-Y2-Y3-Y4 is not —CH2—O—N(Ra)—C(═O)—, wherein Ra 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 Rb, or Ra is pyridyl-methyl- or pyridyl-methyl-substituted by one to three Rb;
and each Rb is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy.

9 more elements

Dependencies are inferred from the claim text.

Insecticidal compounds

Life of this patent

Insecticidal compounds

Life of this patent

Abstract

Claims21