Phthalamide derivatives, intermediates in the production thereof, and agricultural/horticultural insecticides and method for using the same

A heterocyclic amine derivative represented by the following formula (IV′):

• Q′—NH2 (IV′)
• wherein:
• (1) in cases where Q′ represents Q26,
• Y, which may be same or different, represents halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkyl-sulfonyl group or halo C1-C6 alkylsulfonyl group, m represents an integer of 1 to 4, and at least one of Y, of which total number is m, is perfluoro C3-C6 alkyl group;
• and
• (2) in a case where Q′ represents Q27:
• Y, which may be same or different, represents halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkyl-sulfonyl group or halo C1-C6 alkylsulfonyl group, m represents an integer of 1 to 4, and at least one of Y, of which total number is m, is perfluoro C2-C6 alkyl group, halo C1-C6 alkoxy group or halo C1-C6 alkylthio group.

An agrohorticultural insecticide containing, as an active ingredient thereof, a phthalamide derivative represented by the following formula (I):

• wherein R1, R2 and R3, which may be same or different, represent hydrogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group or —A1—(G)r (in this formula, A1 represents C1-C8 alkylene group, C3-C6 alkenylene group or C3-C6 alkynylene group;
• G, which may be same or different, represents hydrogen atom, halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, di(C1-C6)alkoxyphosphoryl group in which the (C1-C6)alkoxy groups may be same or different, di(C1-C6) alkoxythiophosphoryl group in which the (C1-C6)alkoxy groups may be same or different, diphenylphosphino group, diphenylphosphono group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group (as used herein, the term “heterocyclic group” means pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group or pyrazolyl group), substituted heterocyclic group (the term heterocyclic group is as defined above) having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —Z3—R4 (in this formula, Z3 represents —O—, —S—, —SO—, —SO2—, —N(R5)— (in this formula, R5 represents hydrogen atom, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkoxycarbonyl group, phenylcarbonyl group, substituted phenylcarbonyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, phenyl C1-C4 alkoxycarbonyl group, substituted phenyl C1-C4 alkoxycarbonyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, C1-C6 alkylsulfonyl group or halo C1-C6 alkylsulfonyl group), —C(═O)— or —C(═NOR6)— (in this formula, R6 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl C1-C4 alkyl group, or substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group), and R4 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy C1-C6 alkyl group, C1-C6 alkylthio C1-C6 alkyl group, formyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkoxycarbonyl group, mono(C1-C6)alkylaminocarbonyl group, di(C1-C6)alkylaminocarbonyl group in which the (C1-C6)alkyl groups may be same or different, mono(C1-C6)alkylaminothiocarbonyl group, di(C1-C6)alkylaminothiocarbonyl group in which the (C1-C6)alkyl groups may be same or different, di(C1-C6)alkoxyphosphoryl group in which the (C1-C6)alkoxy groups may be same or different, di(C1-C6)alkoxythiophosphoryl group in which the (C1-C6)alkoxy groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, phenyl C1-C4 alkyl group, substituted phenyl (C1-C4)alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group (the term heterocyclic group is as defined above), or substituted heterocyclic group (the term heterocyclic group is as defined above) having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group);
• and r represents an integer of 1 to 4);
• further, R1 and R2 may be taken conjointly with the N to which they are attached to form 4- to 7-membered rings which may be intercepted by 1 to 3, same or different oxygen atom, sulfur atom or nitrogen atom;
• X, which may be same or different, represents halogen atom, cyano group, nitro group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group (the term heterocyclic group is as defined above), substituted heterocyclic group (the term heterocyclic group is as defined above) having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —A2—R7
• n represents an integer of 0 to 4;
• further, X may be taken conjointly with the adjacent carbon atom on the phenyl ring to form a fused ring (as used herein, the term fused ring means naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, chroman, isochroman, indole, indoline, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole, benzimidazole or indazole), and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group (the term heterocyclic group is as defined above), and substituted heterocyclic group (the term heterocyclic group is as defined above) having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group;
• Q represents an N—, S— or O—containing, optionally substituted, heterocyclic group or fused heterocyclic group, selected from the group consisting of the following formulas Q26 to Q28 and Q46;
• (in these formulas, Y, which may be same or different, represents halogen atom, cyano group, nitro group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group (the term heterocyclic group is as defined above), substituted heterocyclic group (the term heterocyclic group is as defined above) having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, or —A2—R7 (in this formula, A2 and R7 are as defined above);
• m represents an integer of 0 to 6;
• alternatively, Y may be taken conjointly with adjacent carbon atom on the ring to form a fused ring (the fused ring is as defined above), and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group, heterocyclic group (the term heterocyclic group is as defined above), and substituted heterocyclic group (the term heterocyclic group is as defined above) having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group;
• and Z1 and Z2 represent oxygen atom or sulfur atom.