US 2025/0185656 A1 · PIPERIDINONE DERIVATIVE OR SALT THEREOF, HARMFUL ORGANISM CONTROL AGENT CONTAINING SAID COMPOUND, AND METHOD FOR USING SAME

Abstract

The invention provides a compound represented by the formula (1) wherein X is CH2 or an oxygen atom, Y is an oxygen atom or a sulfur atom, R1 is a substituted phenyl group or the like, R2 is a substituted phenyl group or the like, and R3 is a hydrogen atom or the like, or salts thereof, pest control agents containing the compound as an active ingredient, and methods of use thereof. The compound can be useful, for example, as an agrohorticultural insect pest control agent in the production of crops in agriculture, an ectoparasite control agent for animals, and an endoparasite control agent for animals.

A compound represented by the formula (1)

wherein
R1 is
(a1) a (C1-C6)alkyl group;
(a2) a (C2-C6)alkenyl group;
(a3) a (C2-C6)alkynyl group;
(a4) a (C3-C6)cycloalkyl group;
(a5) a halo(C1-C6)alkyl group;
(a6) a halo(C2-C6)alkenyl group;
(a7) a halo(C2-C6)alkynyl group;
(a8) a halo(C3-C6)cycloalkyl group;
(a9) a substituted (C1-C6)alkyl group having 1 to 3 substituents each independently selected from substituent group A;
(a10) a substituted (C3-C6)cycloalkyl group having 1 to 3 substituents each independently selected from substituent group B;
(a1 l) phenyl(C1-C6)alkyl group (excluding phenylmethyl group);
(a12) a substituted phenyl(C1-C6)alkyl group having, on a ring, 1 to 5 substituents each independently selected from substituent group C;
(a13) a pyridyl(C1-C6)alkyl group;
(a14) a substituted pyridyl(C1-C6)alkyl group having, on a ring, 1 to 4 substituents each independently selected from substituent group C;
(a15) a (C1-C6)alkylcarbonyl group;
(a16) a halo(C1-C6)alkylcarbonyl group;
(a17) a substituted (C1-C6)alkylcarbonyl group having 1 to 3 substituents each independently selected from substituent group A;
(a18) a phenylcarbonyl group;
(a19) a substituted phenylcarbonyl group having, on a ring, 1 to 5 substituents each independently selected from substituent group C;
(a20) a pyridylcarbonyl group;
(a21) a substituted pyridylcarbonyl group having, on a ring, 1 to 4 substituents each independently selected from substituent group C;
(a22) a furanylcarbonyl group;
(a23) a substituted furanylcarbonyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group C;
(a24) a thienylcarbonyl group;
(a25) a substituted thienylcarbonyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group C;
(a26) a pyrazolylcarbonyl group;
(a27) a substituted pyrazolylcarbonyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group C;
(a28) a triazolylcarbonyl group;
(a29) a substituted triazolylcarbonyl group having, on a ring, 1 or 2 substituents each independently selected from substituent group C;
(a30) a dioxodihydrobenzofuranylcarbonyl group;
(a31) a substituted dioxodihydrobenzofuranylcarbonyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group C;
(a32) a dihydrobenzodioxinylcarbonyl group;
(a33) a substituted dihydrobenzodioxinylcarbonyl group having, on a ring, 1 to 7 substituents each independently selected from substituent group C;
(a34) a (C1-C6)alkoxycarbonyl group;
(a35) a halo(C1-C6)alkoxycarbonyl group;
(a36) a substituted (C1-C6)alkoxycarbonyl group having 1 to 3 substituents each independently selected from substituent group A;
(a37) a phenyl(C1-C6)alkoxycarbonyl group;
(a38) a substituted phenyl(C1-C6)alkoxycarbonyl group having 1 to 5 substituents each independently selected from substituent group C;
(a39) a (C1-C6)alkylsulfonyl group;
(a40) a (C3-C6)cycloalkylsulfonyl group;
(a41) a halo(C1-C6)alkylsulfonyl group;
(a42) a halo(C3-C6)cycloalkylsulfonyl group;
(a43) a substituted (C1-C6)alkylsulfonyl group having 1 to 3 substituents each independently selected from substituent group A;
(a44) a substituted (C3-C6)cycloalkylsulfonyl group having 1 to 3 substituents each independently selected from substituent group B;
(a45) a halo(C1-C6)alkoxyhalo(C1-C6)alkylsulfonyl group;
(a46) a phenylsulfonyl group;
(a47) a substituted phenylsulfonyl group having 1 to 5 substituents each independently selected from substituent group C;
(a48) a thienylsulfonyl group;
(a49) a substituted thienylsulfonyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group C;
(a50) a pyrazolylsulfonyl group;
(a51) a substituted pyrazolylsulfonyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group C;
(a52) a thiazolylsulfonyl group;
(a53) a substituted thiazolylsulfonyl group having, on a ring, 1 or 2 substituents each independently selected from substituent group C;
(a54) an isoxazolylsulfonyl group;
(a55) a substituted isoxazolylsulfonyl group having, on a ring, 1 or 2 substituents each independently selected from substituent group C;
(a56) a quinolinylsulfonyl group;
(a57) a substituted quinolinylsulfonyl group having, on a ring, 1 to 6 substituents each independently selected from substituent group C;
(a58) a phenyl(C1-C6)alkylsulfonyl group;
(a59) a substituted phenyl(C1-C6)alkylsulfonyl group having 1 to 5 substituents each independently selected from substituent group C;
(a60) an aryl group;
(a61) a substituted aryl group having, on a ring, one or more substituents each independently selected from substituent group D;
(a62) a 5- to 10-membered ring heterocyclic group;
(a63) a substituted 5- to 10-membered ring heterocyclic group having, on a ring, one or more substituents each independently selected from substituent group D;
(a64) a (C3-C6)cycloalkylcarbonyl group;
(a65) a substituted (C3-C6)cycloalkylcarbonyl group having 1 to 3 substituents each independently selected from substituent group B;
(a66) an isoxazolylcarbonyl group;
(a67) a substituted isoxazolylcarbonyl group having, on a ring, 1 or 2 substituents each independently selected from substituent group C;
(a68) a phenylaminocarbonyl group;
(a69) a substituted phenylaminocarbonyl group having, on a ring, 1 to 5 substituents each independently selected from substituent group C;
(a70) a pyrimidinylcarbonyl group;
(a71) a substituted pyrimidinylcarbonyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group C;
(a72) a pyrazinylcarbonyl group;
(a73) a substituted pyrazinylcarbonyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group C;
(a74) a pyridazinylcarbonyl group;
(a75) a substituted pyridazinylcarbonyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group C;
(a76) a naphthylcarbonyl group;
(a77) a substituted naphthylcarbonyl group having, on a ring, 1 to 7 substituents each independently selected from substituent group C;
(a78) quinolinylcarbonyl group;
or (a79) a substituted quinolinylcarbonyl group having, on a ring, 1 to 6 substituents each independently selected from substituent group C,
R2 is
(b1) an amino group;
(b2) a (C1-C6)alkyl group;
(b3) a (C2-C6)alkenyl group;
(b4) a (C2-C6)alkynyl group;
(b5) a (C3-C6)cycloalkyl group;
(b6) a halo(C1-C6)alkyl group;
(b7) a halo(C2-C6)alkenyl group;
(b8) a halo(C2-C6)alkynyl group;
(b9) a halo(C3-C6)cycloalkyl group;
(b10) a substituted (C1-C6)alkyl group having 1 to 3 substituents each independently selected from substituent group A;
(b11) a substituted (C3-C6)cycloalkyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group B;
(b12) an N—(C1-C6)alkylamino group;
(b13) an N,N-di(C1-C6)alkylamino group;
(b14) an N—(C1-C6)alkyl-N-phenylamino group;
(b15) a (C1-C6)alkylsulfonyl group;
(b16) an N—(C1-C6)alkylaminosulfonyl group;
(b17) an N,N-di(C1-C6)alkylaminosulfonyl group;
(b18) a piperidinyl group;
(b19) a morpholinyl group;
(b20) a phenyl group;
(b21) a substituted phenyl group having, on a ring, 1 to 5 substituents each independently selected from substituent group E;
(b22) a pyridyl group;
(b23) a substituted pyridyl group having, on a ring, 1 to 4 substituents each independently selected from substituent group E;
(b24) a pyridazinyl group;
(b25) a substituted pyridazinyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group E;
(b26) a pyrimidinyl group;
(b27) a substituted pyrimidinyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group E;
(b28) a pyrazinyl group;
(b29) a substituted pyrazinyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group E;
(b30) a triazinyl group;
(b31) a substituted triazinyl group having, on a ring, 1 or 2 substituents each independently selected from substituent group E;
(b32) a furanyl group;
(b33) a substituted furanyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group E;
(b34) an oxazolyl group;
(b35) a substituted oxazolyl group having, on a ring, 1 or 2 substituents each independently selected from substituent group E;
(b36) an isoxazolyl group;
(b37) a substituted isoxazolyl group having, on a ring, 1 or 2 substituents each independently selected from substituent group E;
(b38) a thienyl group;
(b39) a substituted thienyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group E;
(b40) a thiazolyl group;
(b41) a substituted thiazolyl group having, on a ring, 1 or 2 substituents each independently selected from substituent group E;
(b42) an isothiazolyl group;
(b43) a substituted isothiazolyl group having, on a ring, 1 or 2 substituents each independently selected from substituent group E;
(b44) a thiadiazolyl group;
(b45) a substituted thiadiazolyl group having, on a ring, one substituent each independently selected from substituent group E;
(b46) a pyrazolyl group;
(b47) a substituted pyrazolyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group E;
(b48) a triazolyl group;
(b49) a substituted triazolyl group having, on a ring, 1 or 2 substituents each independently selected from substituent group E;
(b50) a tetrazolyl group;
(b51) a substituted tetrazolyl group having, on a ring, one substituent each independently selected from substituent group E;
(b52) a benzoxazolyl group;
(b53) a substituted benzoxazolyl group having, on a ring, 1 to 4 substituents each independently selected from substituent group E;
(b54) a benzothiazolyl group;
(b55) a substituted benzothiazolyl group having, on a ring, 1 to 4 substituents each independently selected from substituent group E;
(b56) a quinolinyl group;
(b57) a substituted quinolinyl group having, on a ring, 1 to 6 substituents each independently selected from substituent group E;
(b58) a naphthyl group;
(b59) a substituted naphthyl group having, on a ring, 1 to 7 substituents each independently selected from substituent group E;
(b60) a tetrahydronaphthyl group;
(b61) a substituted tetrahydronaphthyl group having, on a ring, 1 to 10 substituents each independently selected from substituent group E;
(b62) a phenyl(C1-C6)alkyl group;
(b63) a substituted phenyl(C1-C6)alkyl group having, on a ring, 1 to 5 substituents each independently selected from substituent group E;
(b64) a pyridyl(C1-C6)alkyl group;
(b65) a substituted pyridyl(C1-C6)alkyl group having, on a ring, 1 to 4 substituents each independently selected from substituent group E;
(b66) a pyrazinyl(C1-C6)alkyl group;
(b67) a substituted pyrazinyl(C1-C6)alkyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group E;
(b68) a pyrimidinyl(C1-C6)alkyl group;
(b69) a substituted pyrimidinyl(C1-C6)alkyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group E;
(b70) a furanyl(C1-C6)alkyl group;
(b71) a substituted furanyl(C1-C6)alkyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group E;
(b72) a thienyl(C1-C6)alkyl group;
(b73) a substituted thienyl(C1-C6)alkyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group E;
(b74) a tetrahydrofuranyl(C1-C6)alkyl group;
(b75) a substituted tetrahydrofuranyl(C1-C6)alkyl group having, on a ring, 1 to 3 substituents each independently selected from substituent group E;
(b76) a benzimidazolyl group;
or (b77) a substituted benzimidazolyl group having, on a ring, 1 to 5 substituents each independently selected from substituent group E,
R3 is
(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,
R2 and R3 are optionally bonded to each other to form a ring,
X is CH2 or an oxygen atom,
Y is an oxygen atom or a sulfur atom,
substituent group A consists of
(d1) a cyano group;
(d2) a (C1-C6)alkyl group;
(d3) a (C2-C6)alkenyl group;
(d4) a (C2-C6)alkynyl group;
(d5) a (C3-C6)cycloalkyl group;
(d6) a (C1-C6)alkoxy group;
(d7) a (C1-C6)alkylsulfanyl group;
(d8) a (C1-C6)alkylsulfinyl group;
(d9) a (C1-C6)alkylsulfonyl group;
(d10) a halo(C1-C6)alkyl group;
(d11) a halo(C3-C6)cycloalkyl group;
(d12) a halo(C1-C6)alkoxy group;
(d13) a halo(C1-C6)alkylsulfanyl group;
(d14) a halo(C1-C6)alkylsulfinyl group;
(d15) a halo(C1-C6)alkylsulfonyl group;
(d16) a phenylsulfanyl group;
(d17) an aminocarbonyl group;
(d18) a morpholinyl group;
(d19) a phenylcarbonyl group;
(d20) a substituted phenylcarbonyl group having, on a ring, 1 to 5 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(d21) a pyrazolyl group;
(d22) a substituted pyrazolyl group having, on a ring, 1 to 3 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(d23) a thienyl group;
and (d24) a substituted thienyl group having, on a ring, 1 to 3 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group,
substituent group B consists of
(e1) a cyano group;
(e2) a (C1-C6)alkyl group;
(e3) a (C2-C6)alkenyl group;
(e4) a (C2-C6)alkynyl group;
(e5) a (C3-C6)cycloalkyl group;
(e6) a (C1-C6)alkoxy group;
(e7) a (C1-C6)alkylsulfanyl group;
(e8) a (C1-C6)alkylsulfinyl group;
(e9) a (C1-C6)alkylsulfonyl group;
(e10) a halo(C1-C6)alkyl group;
(e11) a halo(C3-C6)cycloalkyl group;
(e12) a halo(C1-C6)alkoxy group;
(e13) a halo(C1-C6)alkylsulfanyl group;
(e14) a halo(C1-C6)alkylsulfinyl group;
(e15) a halo(C1-C6)alkylsulfonyl group;
(e16) an aminocarbonyl group;
and (e17) a phenyl group,
substituent group C consists of
(f1) a halogen atom;
(f2) a cyano group;
(f3) a nitro group;
(f4) a hydroxyl group;
(f5) a carboxyl group;
(f6) a (C1-C6)alkyl group;
(f7) a (C2-C6)alkenyl group;
(f8) a (C2-C6)alkynyl group;
(f9) a (C1-C6)alkoxy group;
(f10) a (C3-C6)cycloalkyl group;
(f11) a (C1-C6)alkylsulfanyl group;
(f12) a (C1-C6)alkylsulfinyl group;
(f13) a (C1-C6)alkylsulfonyl group;
(f14) a halo(C1-C6)alkyl group;
(f15) a halo(C2-C6)alkenyl group;
(f16) a halo(C2-C6)alkynyl group;
(f17) a halo(C1-C6)alkoxy group;
(f18) a halo(C3-C6)cycloalkyl group;
(f19) a halo(C1-C6)alkylsulfanyl group;
(f20) a halo(C1-C6)alkylsulfinyl group;
(f21) a halo(C1-C6)alkylsulfonyl group;
(f22) a (C1-C6)alkylcarbonyl group;
(f23) a (C1-C6)alkoxycarbonyl group;
(f24) a phenyl group;
(f25) a substituted phenyl group having, on a ring, 1 to 5 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(f26) a phenoxy group;
(f27) a substituted phenoxy group having, on a ring, 1 to 5 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(f28) a methylenedioxy group formed by two adjacent substituents together and optionally substituted by 1 or 2 substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6)alkyl group;
(f29) a (C1-C6)alkylcarbonylamino group;
(f30) a halo(C1-C6)alkylcarbonylamino group;
and (f31) a (C1-C6)alkylsulfanyl(C1-C6)alkylaminocarbonyl group,
substituent group D consists of
(g1) a halogen atom;
(g2) a cyano group;
(g3) a nitro group;
(g4) a hydroxyl group;
(g5) a carboxyl group;
(g6) a (C1-C6)alkyl group;
(g7) a (C2-C6)alkenyl group;
(g8) a (C2-C6)alkynyl group;
(g9) a (C1-C6)alkoxy group;
(g10) a (C3-C6)cycloalkyl group;
(g11) a (C1-C6)alkylsulfanyl group;
(g12) a (C1-C6)alkylsulfinyl group;
(g13) a (C1-C6)alkylsulfonyl group;
(g14) a halo(C1-C6)alkyl group;
(g15) a halo(C2-C6)alkenyl group;
(g16) a halo(C2-C6)alkynyl group;
(g17) a halo(C1-C6)alkoxy group;
(g18) a halo(C3-C6)cycloalkyl group;
(g19) a halo(C1-C6)alkylsulfanyl group;
(g20) a halo(C1-C6)alkylsulfinyl group;
(g21) a halo(C1-C6)alkylsulfonyl group;
(g22) a substituted (C3-C6)cycloalkyl group having, on a ring, 1 to 3 substituents each independently selected from the group consisting of a cyano group, a (C1-C6)alkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkoxy group, and a (C1-C6)alkylcarbonyl group;
(g23) a (C1-C6)alkoxy(C1-C6)alkyl group;
(g24) a (C1-C6)alkoxy(C1-C6)alkoxy group;
(g25) a (C1-C6)alkylcarbonylamino group;
(g26) a halo(C1-C6)alkylcarbonylamino group;
(g27) a (C1-C6)alkylsulfonylamino group;
(g28) a halo(C1-C6)alkylsulfonylamino group;
(g29) a (C1-C6)alkoxycarbonyl group;
(g30) an N—(C1-C6)alkylaminocarbonyl group;
(g31) an N,N-di(C1-C6)alkylaminocarbonyl group;
(g32) an N-halo(C1-C6)alkylaminocarbonyl group;
(g33) an N—(C1-C6)alkylaminosulfonyl group;
(g34) an N,N-di(C1-C6)alkylaminosulfonyl group;
(g35) a furanyl group;
(g36) a substituted furanyl group having, on a ring, 1 to 3 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g37) an oxazolyl group;
(g38) a substituted oxazolyl group having, on a ring, 1 or 2 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g39) an isoxazolyl group;
(g40) a substituted isoxazolyl group having, on a ring, 1 or 2 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g41) an oxadiazolyl group;
(g42) a substituted oxadiazolyl group having, on a 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 halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g43) a thienyl group;
(g44) a substituted thienyl group having, on a ring, 1 to 3 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, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g45) a thiazolyl group;
(g46) a substituted thiazolyl group having, on a ring, 1 or 2 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g47) an isothiazolyl group;
(g48) a substituted isothiazolyl group having, on a ring, 1 or 2 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g49) a thiadiazolyl group;
(g50) a substituted thiadiazolyl group having, on a 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 halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g51) a pyrrolyl group;
(g52) a substituted pyrrolyl group having, on a ring, 1 to 3 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g53) a pyrazolyl group;
(g54) a substituted pyrazolyl group having, on a ring, 1 or 2 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g55) an imidazolyl group;
(g56) a substituted imidazolyl group having, on a ring, 1 or 2 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g57) a triazolyl group;
(g58) a substituted triazolyl group having, on a 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 halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g59) a tetrazolyl group;
(g60) a substituted tetrazolyl group having, on a 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 halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g61) an oxazolinyl group;
(g62) a substituted oxazolinyl group having, on a ring, 1 to 4 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g63) a thiazolinyl group;
(g64) a substituted thiazolinyl group having, on a ring, 1 to 4 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g65) an isoxazolinyl group;
(g66) a substituted isoxazolinyl group having, on a ring, 1 to 4 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g67) an isothiazolinyl group;
(g68) a substituted isothiazolinyl group having, on a ring, 1 to 4 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g69) a pyrrolidinyl group;
(g70) a substituted pyrrolidinyl group having, on a ring, 1 to 4 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g71) an imidazolinyl group;
(g72) a substituted imidazolinyl group having, on a ring, 1 to 4 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g73) a phenyl group;
(g74) a substituted phenyl group having, on a ring, 1 to 5 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, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g75) a pyridyl group;
(g76) a substituted pyridyl group having, on a ring, 1 to 4 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g77) a pyridazinyl group;
(g78) a substituted pyridazinyl group having, on a ring, 1 to 3 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g79) a pyrimidinyl group;
(g80) a substituted pyrimidinyl group having, on a ring, 1 to 3 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g81) a pyrazinyl group;
(g82) a substituted pyrazinyl group having, on a ring, 1 to 3 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g83) a triazinyl group;
(g84) a substituted triazinyl group having, on a ring, 1 or 2 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g85) a dihydrofuranyl group;
(g86) a dihydropyranyl group;
(g87) a phenyloxy group;
(g88) a substituted phenyloxy group having, on a ring, 1 to 5 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g89) a phenyl(C1-C6)alkoxy group;
(g90) a substituted phenyl(C1-C6)alkoxy group having, on a ring, 1 to 5 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(g91) a methylenedioxy group formed by two adjacent substituents together and optionally substituted by 1 or 2 substituents selected from the group consisting of a halogen atom, a phenyl group, and a (C1-C6)alkyl group;
and (g92) an R4—(R5—N═)O═S group (wherein R4 is 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, R5 is a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkylcarbonyl group, or a halo(C1-C6)alkylcarbonyl group)), and
substituent group E consists of
(h1) a halogen atom;
(h2) a cyano group;
(h3) a nitro group;
(h4) an amino group;
(h5) a hydroxyl group;
(h6) a carboxyl group;
(h7) a (C1-C6)alkyl group;
(h8) a (C1-C6)alkoxy group;
(h9) a (C3-C6)cycloalkyl group;
(h10) a (C1-C6)alkylsulfanyl group;
(h11) a (C1-C6)alkylsulfinyl group;
(h12) a (C1-C6)alkylsulfonyl group;
(h13) a halo(C1-C6)alkyl group;
(h14) a halo(C1-C6)alkoxy group;
(h15) a halo(C3-C6)cycloalkyl group;
(h16) a halo(C1-C6)alkylsulfanyl group;
(h17) a halo(C1-C6)alkylsulfinyl group;
(h18) a halo(C1-C6)alkylsulfonyl group;
(h19) a (C1-C6)alkoxycarbonyl group;
(h20) a phenyl(C1-C6)alkoxycarbonyl group;
(h21) a (C1-C6)alkylaminocarbonyl group;
(h22) an N-halo(C1-C6)alkylaminocarbonyl group;
(h23) a phenyl group;
(h24) a substituted phenyl group having, on a ring, 1 to 5 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
(h25) a methylenedioxy group formed by two adjacent substituents together and optionally substituted by 1 or 2 substituents selected from the group consisting of a halogen atom and a (C1-C6)alkyl group;
(h26) a (C1-C6)alkylsulfonylamino group;
(h27) a (C1-C6)alkylaminosulfonyl group;
(h28) a (C1-C6)alkylcarbonylamino group;
(h29) a phenoxy group;
(h30) a substituted phenoxy group having, on a ring, 1 to 5 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, a halo(C1-C6)alkyl group, and a halo(C1-C6)alkoxy group;
and (h31) an SF5 group,
provided that, in (a61) a substituted aryl group and (a63) a substituted 5- to 10-membered ring heterocyclic group for R1, an atom adjacent to a bonding atom to a piperidine ring is not substituted by 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, or an R4—(R5—N═)O═S group (wherein R4 is 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 R5 is a hydrogen atom, a cyano group, a (C1-C6)alkyl group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a (C1-C6)alkylcarbonyl group, or a halo(C1-C6)alkylcarbonyl group), and
provided that the compounds represented by the following structural formulas are excluded:
or a salt thereof.

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Piperidinone derivative or salt thereof, harmful organism control agent containing said compound, and method for using same

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Piperidinone derivative or salt thereof, harmful organism control agent containing said compound, and method for using same

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Abstract

Claims11