Isoxazoline compounds and their use in pest control

An isoxazoline compound represented by the formula (1):

• wherein R1 is a C1-C4 haloalkyl group,
• R2 is a C1-C6 alkyl group unsubstituted or substituted with one or more halogen atoms, a C1-C6 alkoxy group unsubstituted or substituted with one or more halogen atoms, a halogen atom, a C1-C6 alkylsulfenyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a nitro group or a cyano group,
• R3 is a C1-C6 alkyl group, a C1-C6 alkoxy group, a nitro group or a halogen atom,
• m is an integer of 0 to 5,
• n is an integer of 0 to 4,
• M is an oxygen atom or a sulfur atom,
• R4 is a hydrogen atom;
• a C1-C12 alkyl group unsubstituted or substituted with one or more halogen atoms;
• a (C2-C5 alkoxycarbonyl)C1-C12 alkyl group;
• a C2-C12 cyanoalkyl group;
• a C3-C12 cycloalkyl group unsubstituted or substituted with one or more halogen atoms;
• a (C3-C6 cycloalkyl)C1-C6 alkyl group;
• a (C1-C6 alkoxy)C2-C6 alkyl group;
• a C2-C12 alkenyl group unsubstituted or substituted with one or more halogen atoms;
• a C2-C12 alkynyl group unsubstituted or substituted with one or more halogen atoms;
• a C1-C6 alkoxy group unsubstituted or substituted with one or more halogen atoms;
• a (C1-C6 alkoxy)C1-C6 alkoxy group;
• a C3-C6 alkenyloxy group unsubstituted or substituted with one or more halogen atoms;
• a benzyloxy group;
• a phenyl(C2-C6)alkenyl group;
• a (C1-C6 alkylamino)C1-C6 alkyl group;
• a (di(C1-C6 alkyl)amino)C1-C6 alkyl group;
• a group represented by the following formula:
• [wherein A1 is a C1-C4 alkyl group unsubstituted or substituted with one or more halogen atoms, a C1-C4 alkoxy group unsubstituted or substituted with one or more halogen atoms, a halogen atom or a cyano group,
• q is an integer of 0 to 3,
• r is an integer of 0 to 2, and
• X1, X2 and X3 represent a combination of one nitrogen atom and two CH groups, or a combination of three CH groups];
• a group represented by the following formula:
• [wherein A2 is a C1-C4 alkyl group, a halogen atom or a nitro group,
• t is an integer of 0 to 3,
• u is an integer of 0 to 2, and
• X4 is an oxygen atom, a sulfur atom or NH];
• a group represented by the following formula:
• [wherein L1 is a C1-C6 alkyl group unsubstituted or substituted with one or more halogen atoms, or a C3-C8 cycloalkyl group, and
• L2 is a hydrogen atom or a C1-C6 alkyl group unsubstituted or substituted with one or more halogen atoms, or L1 and L2, when taken together, represent a C2-C9 alkanediyl group, a CH2CH2CH(CH3)CH2CH2 group or a CH2CH2OCH2CH2 group];
• a phenyl group;
• a phenyl(C1-C4)alkyl group;
• a phenoxy group;
• a phenoxy(C1-C4)alkyl group;
• a phenylamino group or a phenyl(C1-C2)alkylamino group, wherein the benzene ring of any of said phenyl group, said phenyl(C1-C4)alkyl group, said phenoxy group, said phenoxy(C1-C4)alkyl group, said phenylamino group and said phenyl(C1-C2)alkylamino group may be substituted with 1 to 5 groups independently selected from the group consisting of C1-C6 alkyl groups unsubstituted or substituted with one or more halogen atoms, C1-C6 alkoxy groups unsubstituted or substituted with one or more halogen atoms, halogen atoms, nitro group, cyano group, C1-C6 alkylsulfenyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups, C2-C6 alkoxycarbonyl groups and benzoyl group, and
• R5 is a hydrogen atom, a C1-C12 alkyl group, a C3-C12 cycloalkyl group, a (C3-C6 cycloalkyl)C1-C6 alkyl group, a C2-C6 alkoxyalkyl group, a C3-C12 alkenyl group, a C3-C12 alkynyl group, a C1-C6 acyl group, a C2-C8 cyanoalkyl group, a nitromethyl group, a C2-C6 alkoxycarbonyl group, a C3-C8 alkoxycarbonylalkyl group, a phenyl(C1-C4)alkyl group or a benzoyl group, wherein the benzene ring of said phenyl(C1-C4)alkyl group or said benzoyl group may be substituted with 1 to 5 groups independently selected from the group consisting of C1-C6 alkyl groups unsubstituted or substituted with one or more halogen atoms, C1-C6 alkoxy groups unsubstituted or substituted with one or more halogen atoms, halogen atoms, nitro group and cyano group.