US 12,723,036 B2 · Aryltetrahydropyridazine derivative or salt thereof, insecticidal agent containing the compound, and method of use thereof

Abstract

Crop production in agriculture, horticulture, and the like has still been significantly damaged by pests and the like, and pests that are resistant to existing drugs have appeared. Due to such concerns, it is desired to develop novel insecticidal agents and acaricides. The present invention has found that a compound represented by general formula (1): wherein X and Y represent an oxygen atom or a sulfur atom, R1 represents a hydrogen atom or the like, R2 represents a substituted phenyl group or the like, R3 represents a hydrogen atom or the like, and R4 represents a phenyl group or the like, or a salt thereof has a high insecticidal effect on pests in agriculture and horticulture, and the like. The present invention provides an agricultural and horticultural insecticidal agent containing the compound or a salt thereof as an active ingredient, and a method of use thereof.

A compound represented by general formula (1):

wherein,
R1 represents
(a1) a hydrogen atom;
(a2) a (C1-C6)alkyl group;
(a3) a (C2-C6)alkenyl group;
(a4) a (C2-C6)alkynyl group;
(a5) a (C3-C6)cycloalkyl group;
(a6) a (C1-C6)alkoxy group;
(a7) a halo(C1-C6)alkyl group;
(a8) a (C1-C6)alkylcarbonyl group;
(a9) a (C1-C6)alkoxycarbonyl group;
(a10) a substituted (C1-C6)alkyl group having on the chain one to three substituents each independently selected from the group consisting of a cyano group, a (C1-C6)alkoxy group, and a (C3-C6)cycloalkyl group;
(a11) a thiazolylmethyl group;
(a12) a substituted thiazolylmethyl group having on the ring one to two substituents each independently selected from the group consisting of a halogen atom, a (C1-C6)alkyl group, and a (C1-C6)alkoxy group;
(a13) a benzyl group;
or
(a14) a substituted benzyl group having on the ring one to three substituents each independently selected from the group consisting of a halogen atom, a (C1-C6)alkyl group, and a (C1-C6)alkoxy group,
R2 represents
(b1) an aryl group;
(b2) a substituted aryl group having on the ring one or more substituents each independently selected from substituent group A;
(b3) a 5- to 10-membered ring heterocyclic group;
or
(b4) a substituted 5- to 10-membered ring heterocyclic group having on the ring one or more substituents each independently selected from the substituent group A, provided that R2 does not have a substitution with a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylsulfonyl group, an N—(C1-C6)alkylaminosulfonyl group, an N,N-di(C1-C6)alkylaminosulfonyl group, and an R6—(R7—N=)O=S group (wherein R6 represents a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, or a (C1-C6)alkoxy(C1-C6)alkyl group, and R7 represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a (C2-C6)alkylcarbonyl group, or a halo(C2-C6)alkylcarbonyl group) at an adjacent atom to an atom attached to the tetrahydropyridazine ring,
R3 represents
(c1) a hydrogen atom;
(c2) a (C1-C6)alkyl group;
(c3) a (C3-C6)cycloalkyl group;
(c4) a (C1-C6)alkoxy group;
or
(c5) a (C1-C6)alkylcarbonyl group,
R4 represents
(d1) a (C1-C6)alkyl group;
(d2) a (C2-C6)alkenyl group;
(d3) a (C2-C6)alkynyl group;
(d4) a (C3-C6)cycloalkyl group;
(d5) a halo(C1-C6)alkyl group;
(d6) a halo(C2-C6)alkenyl group;
(d7) a halo(C2-C6)alkynyl group;
(d8) a substituted (C1-C6)alkyl group having one to three substituents each independently selected from substituent group B;
(d9) a substituted (C3-C6)cycloalkyl group having on the ring one to three substituents each independently selected from substituent group C;
(d10) a (C1-C6)alkylsulfonyl group;
(d11) an N—(C1-C6)alkylsulfamoyl group;
(d12) a phenyl group;
(d13) a substituted phenyl group having on the ring one to five substituents each independently selected from substituent group D;
(d14) a phenyl(C1-C6)alkyl group;
(d15) a substituted phenyl(C1-C6)alkyl group having on the ring one to five substituents each independently selected from the substituent group D;
(d16) a pyridyl group;
(d17) a substituted pyridyl group having on the ring one to four substituents each independently selected from the substituent group D;
(d18) a pyridazinyl group;
(d19) a substituted pyridazinyl group having on the ring one to three substituents each independently selected from the substituent group D;
(d20) a pyrimidinyl group;
(d21) a substituted pyrimidinyl group having on the ring one to three substituents each independently selected from the substituent group D;
(d22) a pyrazinyl group;
(d23) a substituted pyrazinyl group having on the ring one to three substituents each independently selected from the substituent group D;
(d24) a pyrazolyl group;
(d25) a substituted pyrazolyl group having on the ring one to three substituents each independently selected from the substituent group D;
(d26) an isoxazolyl group;
(d27) a substituted isoxazolyl group having on the ring one to two substituents each independently selected from the substituent group D;
(d28) an isothiazolyl group;
(d29) a substituted isothiazolyl group having on the ring one to two substituents each independently selected from the substituent group D;
(d30) an oxazolyl group;
(d31) a substituted oxazolyl group having on the ring one to two substituents each independently selected from the substituent group D;
(d32) a thiazolyl group;
(d33) a substituted thiazolyl group having on the ring one to two substituents each independently selected from the substituent group D;
(d34) a triazolyl group;
(d35) a substituted triazolyl group having on the ring one to two substituents each independently selected from the substituent group D;
(d36) a thiadiazolyl group;
(d37) a substituted thiadiazolyl group having on the ring one substituent each independently selected from the substituent group D;
(d38) a tetrazolyl group;
(d39) a substituted tetrazolyl group having on the ring one substituent each independently selected from the substituent group D;
(d40) a triazinyl group;
(d41) a substituted triazinyl group having on the ring one to two substituents each independently selected from the substituent group D;
(d42) a furyl(C1-C6)alkyl group;
(d43) a substituted furyl(C1-C6)alkyl group having on the ring one to three substituents each independently selected from the substituent group D;
(d44) a thienyl(C1-C6)alkyl group;
(d45) a substituted thienyl(C1-C6)alkyl group having on the ring one to three substituents each independently selected from the substituent group D;
(d46) a quinolinyl group;
(d47) a substituted quinolinyl group having on the ring one to six substituents each independently selected from the substituent group D;
(d48) a benzothiazolyl group;
(d49) a substituted benzothiazolyl group having on the ring one to four substituents each independently selected from the substituent group D;
(d50) a pyridyl(C1-C6)alkyl group;
(d51) a substituted pyridyl(C1-C6)alkyl group having on the ring one to four substituents each independently selected from the substituent group D;
(d52) a pyrazinyl(C1-C6)alkyl group;
(d53) a substituted pyrazinyl(C1-C6)alkyl group having on the ring one to three substituents each independently selected from the substituent group D;
(d54) a naphthyl group;
(d55) a substituted naphthyl group having on the ring one to seven substituents each independently selected from the substituent group D;
(d56) a tetrahydronaphthyl group;
or
(d57) a substituted tetrahydronaphthyl group having on the ring one to ten substituents each independently selected from the substituent group D,
X and Y each independently represent an oxygen atom or a sulfur atom,
the substituent group A consists of
(e1) a halogen atom;
(e2) a cyano group;
(e3) a nitro group;
(e4) a hydroxyl group;
(e5) a carboxyl group;
(e6) a (C1-C6)alkyl group;
(e7) a (C2-C6)alkenyl group;
(e8) a (C2-C6)alkynyl group;
(e9) a (C1-C6)alkoxy group;
(e10) a (C3-C6)cycloalkyl group;
(e11) a (C1-C6)alkylthio group;
(e12) a (C1-C6)alkylsulfinyl group;
(e13) a (C1-C6)alkylsulfonyl group;
(e14) a halo(C1-C6)alkyl group;
(e15) a halo(C2-C6)alkenyl group;
(e16) a halo(C2-C6)alkynyl group;
(e17) a halo(C1-C6)alkoxy group;
(e18) a halo(C3-C6)cycloalkyl group;
(e19) a halo(C1-C6)alkylthio group;
(e20) a halo(C1-C6)alkylsulfinyl group;
(e21) a halo(C1-C6)alkylsulfonyl group;
(e22) a (C1-C6)alkylcarbonylamino group;
(e23) a halo(C1-C6)alkylcarbonylamino group;
(e24) a (C1-C6)alkylsulfonylamino group;
(e25) a halo(C1-C6)alkylsulfonylamino group;
(e26) an SF5 group;
(e27) a (C1-C6)alkoxy(C1-C6)alkyl group;
(e28) an N—(C1-C6)alkylcarboxamide group;
(e29) an N-halo(C1-C6)alkylcarboxamide group;
(e30) an oxadiazolyl group;
(e31) a substituted oxadiazolyl group having on the ring one substituent each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(e32) a (C1-C6)alkoxycarbonyl group;
(e33) a methylenedioxy group formed by two adjacent substituents, wherein the methylenedioxy group is optionally substituted with one to two substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6)alkyl group;
(e34) an N—(C1-C6)alkylaminosulfonyl group;
(e35) an N,N-di(C1-C6)alkylaminosulfonyl group;
(e36) an R6—(R7—N=)O=S group, wherein R6 represents a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, or a (C1-C6)alkoxy(C1-C6)alkyl group, and R7 represents a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a (C2-C6)alkylcarbonyl group, or a halo(C2-C6)alkylcarbonyl group;
and
(e37) a substituted (C3-C6)cycloalkyl group having on the ring one to three substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, and a (C1-C6)alkylcarbonyl group,
the substituent group B consists of
(f1) a cyano group;
(f2) a (C3-C6)cycloalkyl group;
(f3) a (C1-C6)alkoxy group;
(f4) a (C1-C6)alkylthio group;
(f5) a (C1-C6)alkylsulfinyl group;
(f6) a (C1-C6)alkylsulfonyl group;
(f7) a halo(C3-C6)cycloalkyl group;
(f8) a halo(C1-C6)alkoxy group;
(f9) a halo(C1-C6)alkylthio group;
(f10) a halo(C1-C6)alkylsulfinyl group;
(f11) a halo(C1-C6)alkylsulfonyl group;
(f12) a carboxamide group;
and
(f13) a phenylcarbonyl group,
the substituent group C consists of
(g1) a cyano group;
(g2) a (C1-C6)alkyl group;
(g3) a (C3-C6)cycloalkyl group;
(g4) a (C1-C6)alkoxy group;
(g5) a (C1-C6)alkylthio group;
(g6) a (C1-C6)alkylsulfinyl group;
(g7) a (C1-C6)alkylsulfonyl group;
(g8) a halo(C3-C6)cycloalkyl group;
(g9) a halo(C1-C6)alkoxy group;
(g10) a halo(C1-C6)alkylthio group;
(g1l) a halo(C1-C6)alkylsulfinyl group;
(g12) a halo(C1-C6)alkylsulfonyl group;
(g13) a halo(C1-C6)alkyl group;
(g14) a carboxamide group;
(g15) a (C2-C6)alkynyl group;
and
(g16) a phenyl group,
the substituent group D consists of
(h1) a halogen atom;
(h2) a cyano group;
(h3) a hydroxyl group;
(h4) a carboxyl group;
(h5) a (C1-C6)alkyl group;
(h6) a (C1-C6)alkoxy group;
(h7) a (C3-C6)cycloalkyl group;
(h8) a (C1-C6)alkylthio group;
(h9) a (C1-C6)alkylsulfinyl group;
(h10) a (C1-C6)alkylsulfonyl group;
(h11) a halo(C1-C6)alkyl group;
(h12) a halo(C1-C6)alkoxy group;
(h13) a halo(C3-C6)cycloalkyl group;
(h14) a halo(C1-C6)alkylthio group;
(h15) a halo(C1-C6)alkylsulfinyl group;
(h16) a halo(C1-C6)alkylsulfonyl group;
(h17) a (C1-C6)alkoxycarbonyl group;
(h18) an N—(C1-C6)alkylcarboxamide group;
(h19) an N-halo(C1-C6)alkylcarboxamide group;
(h20) a methylenedioxy group formed by two adjacent substituents, wherein the methylenedioxy group is optionally substituted with one to two substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6)alkyl group;
(h21) a nitro group;
(h22) an amino group;
and
(h23) a benzyloxycarbonyl group,
or a salt thereof.

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Aryltetrahydropyridazine derivative or salt thereof, insecticidal agent containing the compound, and method of use thereof

Life of this patent

Aryltetrahydropyridazine derivative or salt thereof, insecticidal agent containing the compound, and method of use thereof

Life of this patent

Abstract

Claims17