US 12,698,269 B2 · 1-aryltetrahydropyridazine-3,5-dione derivative or salt thereof and insecticidal agent containing the compound and method for using same

Abstract

For example, in agricultural and horticultural crop production, pests, etc. still cause heavy damage, and there is a demand for the development of novel agricultural and horticultural insecticidal agents due to factors such as the emergence of pests resistant to existing drugs. The present invention has found that a compound represented by the general formula (1): wherein R1 represents an alkoxycarbonyl group or the like, R2 represents a substituted phenyl group or the like, R3 represents a hydrogen atom or the like, R4 represents a substituted phenyl group or the like, R5 represents an alkyl group or the like, Y represents an oxygen atom or the like and m and n each represent 0 or 1, or a salt thereof exhibits a high insecticidal effect on pests, etc. in the agricultural and horticultural field, and provides an agricultural and horticultural insecticidal agent comprising the same as an active ingredient and a method for using the same.

A compound represented by the general formula (1) or a salt thereof:

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 halo (C1-C6) alkyl group;
(a7) a halo (C3-C6) cycloalkyl group;
(a8) a (C1-C6) alkoxy group;
(a9) a substituted (C1-C6) alkyl group having, on a 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;
(a10) a substituted (C3-C6) cycloalkyl group having one to three substituents each independently selected from the group consisting of a cyano group, a (C1-C6) alkyl group and a (C1-C6) alkoxy group;
(a11) a (C1-C6) alkylcarbonyl group;
(a12) a halo (C1-C6) alkylcarbonyl group;
(a13) a (C3-C6) cycloalkylcarbonyl group;
(a14) a (C1-C6) alkoxy (C1-C6) alkylcarbonyl group;
(a15) a (C1-C6) alkylsulfanyl (C1-C6) alkylcarbonyl group;
(a16) a phenylcarbonyl group;
(a17) a substituted phenylcarbonyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group and a (C1-C6) alkoxy group;
(a18) a thienylcarbonyl group;
(a19) a substituted thienylcarbonyl group having, on a ring, one to three substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group and a (C1-C6) alkoxy group;
(a20) a thiazolylcarbonyl group;
(a21) a substituted thiazolylcarbonyl group having, on a ring, one or two substituents each independently selected from the group consisting of a halogen atom, a cyano group, a (C1-C6) alkyl group and a (C1-C6) alkoxy group;
(a22) a (C1-C6) alkoxycarbonyl group;
(a23) a halo (C1-C6) alkoxycarbonyl group;
(a24) a (C1-C6) alkoxy (C1-C6) alkoxycarbonyl group;
(a25) a (C1-C6) alkylsulfanyl (C1-C6) alkoxycarbonyl group;
(a26) a (C1-C6) alkoxy (C1-C6) alkoxy (C1-C6) alkoxycarbonyl group;
(a27) a (C2-C6) alkenyloxycarbonyl group;
(a28) a (C2-C6) alkynyloxycarbonyl group;
(a29) a (C3-C6) cycloalkoxycarbonyl group;
(a30) a phenyloxycarbonyl group;
(a31) a substituted phenyloxycarbonyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group and a (C1-C6) alkyl group;
(a32) a phenyl (C1-C6) alkoxycarbonyl group;
(a33) a substituted phenyl (C1-C6) alkoxycarbonyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group and a (C1-C6) alkyl group;
(a34) an aminocarbonyl group;
(a35) a N—(C1-C6) alkylaminocarbonyl group;
(a36) a N,N-di-(C1-C6) alkylaminocarbonyl group (wherein the (C1-C6) alkyl moieties are the same as or different from each other);
(a37) a N-halo (C1-C6) alkylaminocarbonyl group;
(a38) a N—(C2-C6) alkenylaminocarbonyl group;
(a39) a N—(C2-C6) alkynylaminocarbonyl group;
(a40) a N—(C1-C6) alkyl-N—(C2-C6) alkynylaminocarbonyl group;
(a41) a N—(C3-C6) cycloalkylaminocarbonyl group;
(a42) a N—(C1-C6) alkoxyaminocarbonyl group;
(a43) a N—(C1-C6) alkoxy (C1-C6) alkylaminocarbonyl group;
(a44) a N—(C1-C6) alkylsulfanyl (C1-C6) alkylaminocarbonyl group;
(a45) a N-phenyl (C1-C6) alkylaminocarbonyl group;
(a46) a N-substituted phenyl (C1-C6) alkylaminocarbonyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group and a (C1-C6) alkyl group;
(a47) a pyrrolidinylcarbonyl group;
(a48) a N—(C1-C6) alkylhydrazinocarbonyl group;
(a49) a N,N-di-(C1-C6) alkylhydrazinocarbonyl group (wherein the (C1-C6) alkyl moieties are the same as or different from each other);
(a50) a N-phenylaminocarbonyl group;
(a51) a N-substituted phenylaminocarbonyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a cyano group and a (C1-C6) alkyl group;
(a52) a (C1-C6) alkylsulfonyl group;
(a53) a halo (C1-C6) alkylsulfonyl group;
(a54) a N—(C1-C6) alkylaminosulfonyl group;
(a55) a N-halo (C1-C6) alkylaminosulfonyl group;
(a56) a (C1-C6) alkylthiocarbonyl group;
(a57) a halo (C1-C6) alkylthiocarbonyl group;
(a58) a (C3-C6) cycloalkylthiocarbonyl group;
(a59) a (C1-C6) alkoxy (C1-C6) alkylthiocarbonyl group;
(a60) a (C1-C6) alkylthio (C1-C6) alkylthiocarbonyl group;
(a61) a (C1-C6) alkoxythiocarbonyl group;
(a62) a halo (C1-C6) alkoxythiocarbonyl group;
(a63) a pyrrolidinylthiocarbonyl group;
(a64) a phenylthiocarbonyl group;
(a65) a substituted phenylthiocarbonyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a cyano group and a (C1-C6) alkyl group;
(a66) a phenyloxythiocarbonyl group;
(a67) a phenyl (C1-C6) alkylthiocarbonyl group;
(a68) a substituted phenyl (C1-C6) alkylthiocarbonyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a cyano group and a (C1-C6) alkyl group;
(a69) a N—(C1-C6) alkylaminothiocarbonyl group;
(a70) a N-halo (C1-C6) alkylaminothiocarbonyl group;
(a71) a N,N-di-(C1-C6) alkylaminothiocarbonyl group (wherein the (C1-C6) alkyl moieties are the same as or different from each other);
(a72) a N—(C2-C6) alkenylaminothiocarbonyl group;
(a73) a N—(C2-C6) alkynylaminothiocarbonyl group;
(a74) a N—(C1-C6) alkyl-N—(C2-C6) alkynylaminothiocarbonyl group;
(a75) a N—(C1-C6) alkylsulfanyl (C1-C6) alkylaminothiocarbonyl group;
(a76) a N—(C3-C6) cycloalkylaminothiocarbonyl group;
(a77) a N—(C1-C6) alkoxy (C1-C6) alkylaminothiocarbonyl group;
(a78) a N-phenylaminothiocarbonyl group;
(a79) a substituted N-phenylaminothiocarbonyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a cyano group and a (C1-C6) alkyl group;
(a80) a N-phenyl (C1-C6) alkylaminothiocarbonyl group;
(a81) a substituted N-phenyl (C1-C6) alkylaminothiocarbonyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a cyano group and a (C1-C6) alkyl group;
(a82) a phenyl (C1-C6) alkyl group;
(a83) a substituted phenyl (C1-C6) alkyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group and a (C1-C6) alkoxy group;
(a84) a thiazolyl (C1-C6) alkyl group;
(a85) a substituted thiazolyl (C1-C6) alkyl group having, on a ring, one or two substituents each independently selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group and a (C1-C6) alkoxy group;
(a86) a phenylsulfonyl group;
or
(a87) a substituted phenylsulfonyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group and a (C1-C6) alkoxy group,
R2 represents
(b1) an aryl group;
(b2) a substituted aryl group having, on a 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 a ring, one or more substituents each independently selected from substituent group A,
R3 represents
(c1) a hydrogen atom;
(c2) a (C1-C6) alkyl group;
(c3) a (C3-C6) cycloalkyl group;
(c4) a (C1-C6) alkoxy group;
(c5) a (C1-C6) alkylcarbonyl group;
or
(c6) a (C1-C6) alkoxycarbonyl 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 halo (C3-C6) cycloalkyl group;
(d9) a substituted (C1-C6) alkyl group having one to three substituents each independently selected from substituent group B;
(d10) a substituted (C3-C6) cycloalkyl group having, on a ring, one to three substituents each independently selected from substituent group C;
(d11) a N,N-di-(C1-C6) alkylamino group (wherein the (C1-C6) alkyl moieties are the same as or different from each other);
(d12) a N—(C1-C6) alkyl-N-phenylamino group;
(d13) a (C1-C6) alkylsulfonyl group;
(d14) a N—(C1-C6) alkylaminosulfonyl group;
(d15) a piperidinyl group;
(d16) a morpholinyl group;
(d17) a phenyl group;
(d18) a substituted phenyl group having, on a ring, one to five substituents each independently selected from substituent group D;
(d19) a pyridyl group;
(d20) a substituted pyridyl group having, on a ring, one to four substituents each independently selected from substituent group D;
(d21) a pyridazinyl group;
(d22) a substituted pyridazinyl group having, on a ring, one to three substituents each independently selected from substituent group D;
(d23) a pyrimidinyl group;
(d24) a substituted pyrimidinyl group having, on a ring, one to three substituents each independently selected from substituent group D;
(d25) a pyrazinyl group;
(d26) a substituted pyrazinyl group having, on a ring, one to three substituents each independently selected from substituent group D;
(d27) a triazinyl group;
(d28) a substituted triazinyl group having, on a ring, one or two substituents each independently selected from substituent group D;
(d29) a furanyl group;
(d30) a substituted furanyl group having, on a ring, one to three substituents each independently selected from substituent group D;
(d31) an oxazolyl group;
(d32) a substituted oxazolyl group having, on a ring, one or two substituents each independently selected from substituent group D;
(d33) an isoxazolyl group;
(d34) a substituted isoxazolyl group having, on a ring, one or two substituents each independently selected from substituent group D;
(d35) a thienyl group;
(d36) a substituted thienyl group having, on a ring, one to three substituents each independently selected from substituent group D;
(d37) a thiazolyl group;
(d38) a substituted thiazolyl group having, on a ring, one or two substituents each independently selected from substituent group D;
(d39) an isothiazolyl group;
(d40) a substituted isothiazolyl group having, on a ring, one or two substituents each independently selected from substituent group D;
(d41) a thiadiazolyl group;
(d42) a substituted thiadiazolyl group having, on a ring, one substituent each independently selected from substituent group D;
(d43) a pyrazolyl group;
(d44) a substituted pyrazolyl group having, on a ring, one to three substituents each independently selected from substituent group D;
(d45) a triazolyl group;
(d46) a substituted triazolyl group having, on a ring, one or two substituents each independently selected from substituent group D;
(d47) a tetrazolyl group;
(d48) a substituted tetrazolyl group having, on a ring, one substituent each independently selected from substituent group D;
(d49) a benzoxazolyl group;
(d50) a substituted benzoxazolyl group having, on a ring, one to four substituents each independently selected from substituent group D;
(d51) a benzothiazolyl group;
(d52) a substituted benzothiazolyl group having, on a ring, one to four substituents each independently selected from substituent group D;
(d53) a quinolinyl group;
(d54) a substituted quinolinyl group having, on a ring, one to six substituents each independently selected from substituent group D;
(d55) a naphthyl group;
(d56) a substituted naphthyl group having, on a ring, one to seven substituents each independently selected from substituent group D;
(d57) a tetrahydronaphthyl group;
(d58) a substituted tetrahydronaphthyl group having, on a ring, one to ten substituents each independently selected from substituent group D;
(d59) a phenyl (C1-C6) alkyl group;
(d60) a substituted phenyl (C1-C6) alkyl group having, on a ring, one to five substituents each independently selected from substituent group D;
(d61) a pyridyl (C1-C6) alkyl group;
(d62) a substituted pyridyl (C1-C6) alkyl group having, on a ring, one to four substituents each independently selected from substituent group D;
(d63) a pyrazinyl (C1-C6) alkyl group;
(d64) a substituted pyrazinyl (C1-C6) alkyl group having, on a ring, one to three substituents each independently selected from substituent group D;
(d65) a pyrimidinyl (C1-C6) alkyl group;
(d66) a substituted pyrimidinyl (C1-C6) alkyl group having, on a ring, one to three substituents each independently selected from substituent group D;
(d67) a furanyl (C1-C6) alkyl group;
(d68) a substituted furanyl (C1-C6) alkyl group having, on a ring, one to three substituents each independently selected from substituent group D;
(d69) a thienyl (C1-C6) alkyl group;
or
(d70) a substituted thienyl (C1-C6) alkyl group having, on a ring, one to three substituents each independently selected from substituent group D,
R3 and R4 are optionally bonded to each other to form a ring,
R5 represents
(e1) a (C1-C6) alkyl group;
(e2) a (C2-C6) alkenyl group;
(e3) a (C2-C6) alkynyl group;
(e4) a (C3-C6) cycloalkyl group;
(e5) a halo (C1-C6) alkyl group;
(e6) a halo (C2-C6) alkenyl group;
(e7) a halo (C2-C6) alkynyl group;
(e8) a halo (C3-C6) cycloalkyl group;
(e9) a substituted (C1-C6) alkyl group having, on a chain, one to three substituents each independently selected from the group consisting of a cyano group, a (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkylcarbonyl group, a (C3-C6) cycloalkylcarbonyl group, a phenylcarbonyl group, a (C1-C6) alkoxycarbonyl group, an aminocarbonyl group, a halo (C1-C6) alkylcarbonyl group, a (C1-C6) alkylsulfanyl group, a tri-(C1-C6) alkylsilyl (C1-C6) alkoxy group (wherein the (C1-C6) alkyl groups are the same as or different from each other), and a tri-(C1-C6) alkylsilyl group (wherein the (C1-C6) alkyl groups are the same as or different from each other);
(e10) a substituted (C3-C6) cycloalkyl group having one to three substituents each independently selected from the group consisting of a cyano group, a (C1-C6) alkyl group, and a (C1-C6) alkoxy group;
(e11) a phenyl (C1-C6) alkyl group;
(e12) a substituted phenyl (C1-C6) alkyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group, a halo (C1-C6) alkoxy group, a (C3-C6) cycloalkyl group, a (C1-C6) alkoxycarbonyl group, a (C1-C6) alkylsulfanyl group, a (C1-C6) alkylsulfinyl group, a (C1-C6) alkylsulfonyl group, a halo (C1-C6) alkylsulfanyl group, a diphenylamino group, a phenoxy group, and a methylenedioxy group formed by two adjacent substituents together;
(e13) a pyridyl (C1-C6) alkyl group;
(e14) a substituted pyridyl (C1-C6) alkyl group having, on a ring, one to four substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group, a halo (C1-C6) alkoxy group, a (C1-C6) alkoxycarbonyl group and a halo (C1-C6) alkylsulfanyl group;
(e15) a thiazolyl (C1-C6) alkyl group;
(e16) a substituted thiazolyl (C1-C6) alkyl group having, on a ring, one or two substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group, a halo (C1-C6) alkoxy group, a (C1-C6) alkoxycarbonyl group and a halo (C1-C6) alkylsulfanyl group;
(e17) an oxadiazolyl (C1-C6) alkyl group;
(e18) a substituted oxadiazolyl (C1-C6) alkyl group having a pyridyl group on a ring;
(e19) a naphthyl (C1-C6) alkyl group;
(e20) a substituted naphthyl (C1-C6) alkyl group having, on a ring, one to seven substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group, a halo (C1-C6) alkoxy group, a (C1-C6) alkoxycarbonyl group and a halo (C1-C6) alkylsulfanyl group;
(e21) a quinolinyl (C1-C6) alkyl group;
(e22) a substituted quinolinyl (C1-C6) alkyl group having, on a ring, one to six substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group, a halo (C1-C6) alkoxy group, a (C1-C6) alkoxycarbonyl group and a halo (C1-C6) alkylsulfanyl group;
(e23) a thienyl (C1-C6) alkyl group;
(e24) a substituted thienyl (C1-C6) alkyl group having, on a ring, one to three substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group, a halo (C1-C6) alkoxy group, a (C1-C6) alkoxycarbonyl group and a halo (C1-C6) alkylsulfanyl group;
(e25) a pyrazolyl (C1-C6) alkyl group;
(e26) a substituted pyrazolyl (C1-C6) alkyl group having, on a ring, one to three substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group, a halo (C1-C6) alkoxy group, a (C1-C6) alkoxycarbonyl group and a halo (C1-C6) alkylsulfanyl group;
(e27) an oxazolyl (C1-C6) alkyl group;
(e28) a substituted oxazolyl (C1-C6) alkyl group having, on a ring, one or two substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group, a halo (C1-C6) alkoxy group, a (C1-C6) alkoxycarbonyl group and a halo (C1-C6) alkylsulfanyl group;
(e29) an imidazolyl (C1-C6) alkyl group;
(e30) a substituted imidazolyl (C1-C6) alkyl group having, on a ring, one to three substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group, a halo (C1-C6) alkoxy group, a (C1-C6) alkoxycarbonyl group and a halo (C1-C6) alkylsulfanyl group;
(e31) a pyridyl group;
(e32) a substituted pyridyl group having, on a ring, one to four substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group, a halo (C1-C6) alkoxy group, a (C1-C6) alkoxycarbonyl group and a halo (C1-C6) alkylsulfanyl group;
(e33) a phenyl group;
(e34) a substituted phenyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6) alkyl group, a (C1-C6) alkoxy group, a halo (C1-C6) alkyl group, a halo (C1-C6) alkoxy group, a (C1-C6) alkoxycarbonyl group and a halo (C1-C6) alkylsulfanyl group;
(e35) a (C1-C6) alkylcarbonyl group;
or
(e36) a hydrogen atom,
R3 and R5 are optionally bonded to each other to form a 5- or 6-membered ring, when R5 is (e36) a hydrogen atom, a group derived from R3 by the removal of an arbitrary hydrogen atom is directly bonded to the sulfur atom bonded to R5 from which the hydrogen atom is removed to form a 5- or 6-membered ring,
Y represents an oxygen atom or NR6 (wherein R6 represents 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, a halo (C1-C6) alkylcarbonyl group, a (C1-C6) alkoxycarbonyl group, a phenylsulfonyl group, or a phenylsulfonyl group having, on a ring, one to five substituents each independently selected from the group consisting of a halogen atom, a cyano group, and a (C1-C6) alkyl group),
m represents 0 or 1,
n represents 0 or 1,
substituent group A 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 N,N-di-(C1-C6) alkylaminosulfonyl group (wherein the (C1-C6) alkyl moieties are the same as or different from each other);
(f23) a substituted (C3-C6) cycloalkyl group having, on a 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;
(f24) a SF5 group;
(f25) a (C1-C6) alkoxy (C1-C6) alkyl group;
(f26) a (C1-C6) alkoxy (C1-C6) alkoxy group;
(f27) a (C1-C6) alkylcarbonylamino group;
(f28) a halo (C1-C6) alkylcarbonylamino group;
(f29) a (C1-C6) alkylsulfonylamino group;
(f30) a halo (C1-C6) alkylsulfonylamino group;
(f31) a (C1-C6) alkoxycarbonyl group;
(f32) a methylenedioxy group formed by two adjacent substituents together and optionally substituted by one or two substituents each selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6) alkyl group;
(f33) a (C1-C6) alkylaminocarbonyl group;
(f34) a N-halo (C1-C6) alkylaminocarbonyl group;
(f35) a furanyl group;
(f36) a substituted furanyl group having, on a 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, a halo (C1-C6) alkyl group and a halo (C1-C6) alkoxy group;
(f37) an oxazolyl group;
(f38) a substituted oxazolyl group having, on a ring, one or two 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;
(f39) an isoxazolyl group;
(f40) a substituted isoxazolyl group having, on a ring, one or two 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;
(f41) an oxadiazolyl group;
(f42) 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;
(f43) a thienyl group;
(f44) a substituted thienyl group having, on a 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, a (C3-C6) cycloalkyl group, a halo (C1-C6) alkyl group and a halo (C1-C6) alkoxy group;
(f45) a thiazolyl group;
(f46) a substituted thiazolyl group having, on a ring, one or two 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;
(f47) an isothiazolyl group;
(f48) a substituted isothiazolyl group having, on a ring, one or two 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;
(f49) a thiadiazolyl group;
(f50) 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;
(f51) a pyrrolyl group;
(f52) a substituted pyrrolyl group having, on a 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, a halo (C1-C6) alkyl group and a halo (C1-C6) alkoxy group;
(f53) a pyrazolyl group;
(f54) a substituted pyrazolyl group having, on a ring, one or two 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;
(f55) an imidazolyl group;
(f56) a substituted imidazolyl group having, on a ring, one or two 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;
(f57) a triazolyl group;
(f58) 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;
(f59) a tetrazolyl group;
(f60) 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;
(f61) an oxazolinyl group;
(f62) a substituted oxazolinyl group having, on a ring, one to four 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;
(f63) a thiazolinyl group;
(f64) a substituted thiazolinyl group having, on a ring, one to four 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;
(f65) an isoxazolinyl group;
(f66) a substituted isoxazolinyl group having, on a ring, one to four 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;
(f67) an isothiazolinyl group;
(f68) a substituted isothiazolinyl group having, on a ring, one to four 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;
(f69) a pyrrolidinyl group;
(f70) a substituted pyrrolidinyl group having, on a ring, one to four 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;
(f71) an imidazolinyl group;
(f72) a substituted imidazolinyl group having, on a ring, one to four 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;
(f73) a phenyl group;
(f74) a substituted phenyl group having, on a ring, one to five 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;
(f75) a pyridyl group;
(f76) a substituted pyridyl group having, on a ring, one to four 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;
(f77) a pyridazinyl group;
(f78) a substituted pyridazinyl group having, on a 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, a halo (C1-C6) alkyl group and a halo (C1-C6) alkoxy group;
(f79) a pyrimidinyl group;
(f80) a substituted pyrimidinyl group having, on a 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, a halo (C1-C6) alkyl group and a halo (C1-C6) alkoxy group;
(f81) a pyrazinyl group;
(f82) a substituted pyrazinyl group having, on a 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, a halo (C1-C6) alkyl group and a halo (C1-C6) alkoxy group;
(f83) a triazinyl group;
(f84) a substituted triazinyl group having, on a ring, one or two 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;
(f85) a dihydrofuranyl group;
(f86) a dihydropyranyl group;
(f87) a phenyloxy group;
(f88) a substituted phenyloxy group having, on a ring, one to five 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;
(f89) a phenyl (C1-C6) alkoxy group;
(f90) a substituted phenyl (C1-C6) alkoxy group having, on a ring, one to five 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;
(f91) a phenyl (C1-C6) alkylsulfanyl group;
(f92) a substituted phenyl (C1-C6) alkylsulfanyl group having, on a ring, one to five 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;
(f93) a 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 (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 (C1-C6) alkylcarbonyl group, or a halo (C1-C6) alkylcarbonyl group);
and
(f94) an aminocarbonyl group,
substituent group B consists of
(g1) a cyano group;
(g2) a (C3-C6) cycloalkyl group;
(g3) a (C1-C6) alkoxy group;
(g4) a (C1-C6) alkylsulfanyl group;
(g5) a (C1-C6) alkylsulfinyl group;
(g6) a (C1-C6) alkylsulfonyl group;
(g7) a halo (C3-C6) cycloalkyl group;
(g8) a halo (C1-C6) alkoxy group;
(g9) a halo (C1-C6) alkylsulfanyl group;
(g10) a halo (C1-C6) alkylsulfinyl group;
(g11) a halo (C1-C6) alkylsulfonyl group;
(g12) a (C1-C6) alkoxycarbonyl group;
(g13) an aminocarbonyl group;
and
(g14) a phenylcarbonyl group,
substituent group C consists of
(h1) a cyano group;
(h2) a (C1-C6) alkyl group;
(h3) a (C2-C6) alkenyl group;
(h4) a (C2-C6) alkynyl group;
(h5) a (C3-C6) cycloalkyl group;
(h6) a (C1-C6) alkoxy group;
(h7) a (C1-C6) alkylsulfanyl group;
(h8) a (C1-C6) alkylsulfinyl group;
(h9) a (C1-C6) alkylsulfonyl group;
(h10) a halo (C1-C6) alkyl group;
(h11) a halo (C3-C6) cycloalkyl group;
(h12) a halo (C1-C6) alkoxy group;
(h13) a halo (C1-C6) alkylsulfanyl group;
(h14) a halo (C1-C6) alkylsulfinyl group;
(h15) a halo (C1-C6) alkylsulfonyl group;
(h16) an aminocarbonyl group;
and
(h17) a phenyl group, and
substituent group D consists of
(i1) a halogen atom;
(i2) a cyano group;
(i3) a nitro group;
(i4) an amino group;
(i5) a hydroxyl group;
(i6) a carboxyl group;
(i7) a (C1-C6) alkyl group;
(i8) a (C1-C6) alkoxy group;
(i9) a (C3-C6) cycloalkyl group;
(i10) a (C1-C6) alkylsulfanyl group;
(i11) a (C1-C6) alkylsulfinyl group;
(i12) a (C1-C6) alkylsulfonyl group;
(i13) a halo (C1-C6) alkyl group;
(i14) a halo (C1-C6) alkoxy group;
(i15) a halo (C3-C6) cycloalkyl group;
(i16) a halo (C1-C6) alkylsulfanyl group;
(i17) a halo (C1-C6) alkylsulfinyl group;
(i18) a halo (C1-C6) alkylsulfonyl group;
(i19) a (C1-C6) alkoxycarbonyl group;
(i20) a phenyl (C1-C6) alkoxycarbonyl group;
(i21) a (C1-C6) alkylaminocarbonyl group;
(i22) a N-halo (C1-C6) alkylaminocarbonyl group;
(i23) a phenyl group;
(i24) a substituted phenyl group having, on a ring, one to five 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
(i25) a methylenedioxy group formed by two adjacent substituents together and optionally substituted by one or two substituents each selected from the group consisting of a halogen atom, a phenyl group and a (C1-C6) alkyl group, on the proviso that in R2, an adjacent atom of an atom bonded to the tetrahydropyridazine ring is not substituted by a (C1-C6) alkylsulfonyl group, a halo (C1-C6) alkylsulfonyl group, N—(C1-C6) alkylaminosulfonyl group, N,N-di-(C1-C6) alkylaminosulfonyl group, and 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 (C1-C6) alkylcarbonyl group, or a halo (C1-C6) alkylcarbonyl group).

374 more elements

1-aryltetrahydropyridazine-3,5-dione derivative or salt thereof and insecticidal agent containing the compound and method for using same

Life of this patent

1-aryltetrahydropyridazine-3,5-dione derivative or salt thereof and insecticidal agent containing the compound and method for using same

Life of this patent

Abstract

Claims7