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  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
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  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
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  • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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  • C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
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  • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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  • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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Definitions

• the present invention relates to an aryltetrahydropyridazine derivative or a salt thereof, an insecticide containing the compound as an active ingredient, and a method for using the same.
• Patent Document 1 reports that certain tetrahydropyridazine-3,5-dione derivatives are useful as pharmaceutical compounds. However, no compound useful as an insecticide is disclosed or suggested in such literature.
• the present inventors have made intensive studies to develop novel insecticides, especially agricultural and horticultural insecticides.
• the present inventors have found that the compound or salts thereof exhibit an excellent effect as an insecticide, and have completed the present invention.
• R1 is (a1) hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C ( a6 ) halo(C1 - C6 )alkyl group; (a7) ( C1 - C6 )alkoxy group; (a8) cyano group, ( C1 - C6 )alkoxy and (C 3 -C 6 )cycloalkyl groups, substituted (C 1 -C 6 )alkyl groups having on the chain 1 to 3 substituents independently selected from the group consisting of (a9) (C (a10) halo( C1- C6 )alkylcarbonyl group; (a11) ( C3 - C6 )cycloalkylcarbonyl group; ( a12 ) ( C
• R3 is (c1) hydrogen atom; (c2) (C 1 -C 6 ) alkyl group; (c3) (C 3 -C 6 ) cycloalkyl group; (c4) (C 1 -C 6 ) alkoxy group; or (c5) (C 1 -C 6 ) represents an alkylcarbonyl group.
• R4 is (d1) (C 1 -C 6 ) alkyl group; (d2) (C 2 -C 6 ) alkenyl group; (d3) (C 2 -C 6 ) alkynyl group; (d4) (C 3 -C 6 ) cyclo (d5) halo(C 1 -C 6 )alkyl group; (d6) halo(C 2 -C 6 )alkenyl group; (d7) halo(C 2 -C 6 )alkynyl group; (d8) substituent substituted (C 1 -C 6 ) alkyl group having 1 to 3 substituents independently selected from group B; (d9) 1 to 3 substituents independently selected from substituent group C (d10) N , N-di( C1 - C6 )alkylamino group; (d11 ) N-( C1 - C6 )alkyl- N-phenylamino group; (d12) (C 1 -C 6 ) alky
• R 3 and R 4 may combine with each other to form a ring.
• X and Y each independently represent an oxygen atom or a sulfur atom.
• Z is an OR 5 group (wherein R 5 is a hydrogen atom, (C 1 -C 6 )alkyl group, (C 1 -C 6 )alkylcarbonyl group, (C 1 -C 6 )alkoxycarbonyl group or ( C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group), S(O)nR 6 group (wherein n is 0, 1 or 2, R 6 is a hydrogen atom, ( C 1 -C 6 )alkyl group, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group or phenyl(C 1 -C 6 )alkyl group), or N(R 7 )R 8 groups (wherein R 7 and R 8 are hydrogen atom, hydroxyl group, (C 1 -C 6 )
• Substituent group A is (e1) halogen atom; (e2) cyano group; ( e3) nitro group; (e4) hydroxyl group; (e5) carboxyl group; (e6) (C 1 -C 6 ) alkyl group; ( e8 ) ( C2- C6 ) alkynyl group; (e9) ( C1 - C6 ) alkoxy group; (e10) (C3 - C6 ) cycloalkyl group; (e11) ( (e12) ( C1 - C6 ) alkylsulfinyl group ; (e13) ( C1 - C6 ) alkylsulfonyl group; (e14 ) halo( C1 - C6 ) alkyl group.
• Substituent group B is (f1) cyano group; (f2) ( C3 - C6 ) cycloalkyl group; (f3) ( C1 - C6 ) alkoxy group; (f4) (C1 - C6 ) alkylthio group; (f5) ( (f6) ( C1 - C6 ) alkylsulfonyl group ; (f7) halo(C3-C6 ) cycloalkyl group; (f8) halo( C1 - C6 ) (f9) halo(C 1 -C 6 )alkylthio group; (f10) halo(C 1 -C 6 )alkylsulfinyl group; (f11) halo(C 1 -C 6 )alkylsulfonyl group; (f12) (C 1 -C 6 ) alkoxycarbonyl group
• Substituent group C is (g1) cyano group; (g2) (C 1 -C 6 ) alkyl group; (g3) (C 2 -C 6 ) alkenyl group; (g4) (C 2 -C 6 ) alkynyl group; (g5) (C ( g6 ) ( C1 -C6) alkoxy group; (g7) ( C1 - C6 ) alkylthio group; (g8) ( C1 - C6 ) alkylsulfinyl group; ( (g9) (C 1 -C 6 )alkylsulfonyl groups; (g10) halo(C 1 -C 6 )alkyl groups; (g11) halo(C 3 -C 6 )cycloalkyl groups; (g12) halo(C 1 - ( g13 ) halo( C1 - C6 )alkylthio groups; (g14) halo( C1 - C6
• Substituent group D is (h1) halogen atom; (h2) cyano group; (h3) nitro group ; (h4) amino group; (h5) hydroxyl group; ( h6 ) carboxyl group; h8) (C 1 -C 6 ) alkoxy group; (h9) (C 3 -C 6 ) cycloalkyl group; (h10) (C 1 -C 6 ) alkylthio group; (h11) (C 1 -C 6 ) alkyl (h12) (C 1 -C 6 )alkylsulfonyl group; (h13) halo(C 1 -C 6 )alkyl group; (h14) halo(C 1 -C 6 )alkoxy group; (h15) halo( (h16) halo( C1- C6 )alkylthio group; (h17 ) halo( C1 - C6 )alkylsulfinyl group;
• R 1 , R 3 , R 4 , X, Y, Z, substituent groups A, B, C and D are the same as in [1];
• R2 is (b5) a phenyl group; (b6) a substituted phenyl group having 1 to 5 substituents on the ring independently selected from Substituent Group A; (b7) a pyridyl group; (b8) from Substituent Group A a substituted pyridyl group having 1 to 4 independently selected substituents on the ring; (b9) a pyridazinyl group; (b10) 1 to 3 substituents independently selected from Substituent Group A substituted pyridazinyl group having on the ring; (b11) pyrimidinyl group; (b12) substituted pyrimidinyl group having 1 to 3 substituents on the ring independently selected from substituent group A; (b13) pyrazinyl group; (b14) a substituted
• R 1 is (a1) hydrogen atom; (a2) (C 1 -C 6 )alkyl group; (a9) (C 1 -C 6 )alkylcarbonyl group; (a10) halo(C 1 -C 6 )alkylcarbonyl group; (a11) ) (C 3 -C 6 ) cycloalkylcarbonyl group; (a12) (C 1 -C 6 )alkoxy(C 1 -C 6 )alkylcarbonyl group; (a13) (C 1 -C 6 )alkylthio(C 1 - ( a14 ) phenylcarbonyl group; (a15) independently selected from the group consisting of halogen atom, cyano group, ( C1 - C6 ) alkyl group and ( C1 - C6 ) alkoxy group; (a16) thienylcarbonyl group; (a17) halogen atom, cyano group, (C 1 - -
• R 1 is (a1) hydrogen atom; (a9) (C 1 -C 6 ) alkylcarbonyl group; (a11) (C 3 -C 6 ) cycloalkylcarbonyl group; (a14) phenylcarbonyl group; substituted phenylcarbonyl groups having 1 to 3 independently selected substituents; (a20) (C 1 -C 6 )alkoxycarbonyl groups; (a21) halo(C 1 -C 6 )alkoxycarbonyl groups; (a22) (a25 ) ( C2 - C6 )alkenyloxycarbonyl group ; (a26) ( C2 - C6 )alkynyloxycarbonyl group ; (a27) (C 3 -C 6 ) cycloalkoxycarbonyl group; (a28) phenyloxycarbonyl group; (a29') substituted phenyloxycarbonyl group having 1 to 3 substituents each independently selected from
• R 2 , R 3 , R 4 , X, Y, Z, substituent groups A, B, C and D are the same as in [1];
• R1 is (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 -C 6 ) cyclo (a6) halo(C 1 -C 6 )alkyl; (a7) (C 1 -C 6 )alkoxy; (a8) cyano, (C 1 -C 6 )alkoxy and (C 3 - C 6 ) substituted (C 1 -C 6 )alkyl groups having on the chain 1 to 3 substituents each independently selected from the group consisting of cycloalkyl groups; (a9) (C 1 -C 6 )alkyl groups; carbonyl group; (a10) halo(C 1 -C 6
• R 1 is (a2) (C 1 -C 6 )alkyl group; (a9) (C 1 -C 6 )alkylcarbonyl group; (a10) halo(C 1 -C 6 )alkylcarbonyl group; (a11) (C 3 -C) 6 ) Cycloalkylcarbonyl group; (a12) ( C1 - C6 )alkoxy( C1 - C6 )alkylcarbonyl group; (a13) ( C1 - C6 )alkylthio( C1 - C6 )alkylcarbonyl group (a14) a phenylcarbonyl group; (a15) 1 to 5 groups each independently selected from the group consisting of a halogen atom, a cyano group, a (C 1 -C 6 )alkyl group and a (C 1 -C 6 )alkoxy group; (a16) a thienylcarbonyl group; (a17
• R 1 is (a9) (C 1 -C 6 ) alkylcarbonyl group; (a11) (C 3 -C 6 ) cycloalkylcarbonyl group; (a14) phenylcarbonyl group; (a15′) 1 each independently selected from a halogen atom (a20) (C 1 -C 6 )alkoxycarbonyl group; (a21) halo(C 1 -C 6 )alkoxycarbonyl group; (a22) (C 1 -C ( a25 ) ( C2 - C6 ) alkenyloxycarbonyl group; (a26) ( C2 - C6 ) alkynyloxycarbonyl group; ( a27 ) ( C3 —C 6 ) a cycloalkoxycarbonyl group; (a28) a phenyloxycarbonyl group; (a29′) a substituted phenyloxycarbonyl group having 1 to 3 substituents each independently
• R1 is (a1) hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C ( a6 ) halo(C1 - C6 )alkyl group; (a7) ( C1 - C6 )alkoxy group; (a8) cyano group, ( C1 - C6 )alkoxy and (C 3 -C 6 )cycloalkyl groups, substituted (C 1 -C 6 )alkyl groups having on the chain 1 to 3 substituents independently selected from the group consisting of (a9) (C (a10) halo( C1- C6 )alkylcarbonyl group; (a11) ( C3 - C6 )cycloalkylcarbonyl group; ( a12 ) ( C1 - C6 ) ( C1 - C6 ) (
• Substituent group A is (e1) halogen atom; (e2) cyano group; ( e3) nitro group; (e4) hydroxyl group; (e5) carboxyl group; (e6) (C 1 -C 6 ) alkyl group; ( e8 ) ( C2- C6 ) alkynyl group; (e9) ( C1 - C6 ) alkoxy group; (e10) (C3 - C6 ) cycloalkyl group; (e11) ( (e12) ( C1 - C6 ) alkylsulfinyl group ; (e13) ( C1 - C6 ) alkylsulfonyl group; (e14 ) halo( C1 - C6 ) alkyl group.
• R 1 and substituent group A are the same as in [12],
• R2 is (b5) a phenyl group; (b6) a substituted phenyl group having 1 to 5 substituents on the ring independently selected from Substituent Group A; (b7) a pyridyl group; (b8) from Substituent Group A a substituted pyridyl group having 1 to 4 independently selected substituents on the ring; (b9) a pyridazinyl group; (b10) 1 to 3 substituents independently selected from Substituent Group A substituted pyridazinyl group having on the ring; (b11) pyrimidinyl group; (b12) substituted pyrimidinyl group having 1 to 3 substituents on the ring independently selected from substituent group A; (b13) pyrazinyl group; (b14) a substituted pyrazinyl group having 1 to 3 substituents on the ring independently selected from Substitu
• R 1 is (a1) hydrogen atom; (a2) (C 1 -C 6 )alkyl group; (a9) (C 1 -C 6 )alkylcarbonyl group; (a10) halo(C 1 -C 6 )alkylcarbonyl group; (a11) ) (C 3 -C 6 ) cycloalkylcarbonyl group; (a12) (C 1 -C 6 )alkoxy(C 1 -C 6 )alkylcarbonyl group; (a13) (C 1 -C 6 )alkylthio(C 1 - ( a14 ) phenylcarbonyl group; (a15) independently selected from the group consisting of halogen atom, cyano group, ( C1 - C6 ) alkyl group and ( C1 - C6 ) alkoxy group; (a16) thienylcarbonyl group; (a17) halogen atom, cyano group, (C 1 - -
• R 1 is (a1) hydrogen atom; (a9) (C 1 -C 6 ) alkylcarbonyl group; (a11) (C 3 -C 6 ) cycloalkylcarbonyl group; (a14) phenylcarbonyl group; substituted phenylcarbonyl groups having 1 to 3 independently selected substituents; (a20) (C 1 -C 6 )alkoxycarbonyl groups; (a21) halo(C 1 -C 6 )alkoxycarbonyl groups; (a22) (a25 ) ( C2 - C6 )alkenyloxycarbonyl group ; (a26) ( C2 - C6 )alkynyloxycarbonyl group ; (a27) (C 3 -C 6 ) cycloalkoxycarbonyl group; (a28) phenyloxycarbonyl group; (a29') substituted phenyloxycarbonyl group having 1 to 3 substituents each independently selected from
• R 2 and substituent group A are the same as in [12],
• R1 is (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 -C 6 ) cyclo (a6) halo(C 1 -C 6 )alkyl; (a7) (C 1 -C 6 )alkoxy; (a8) cyano, (C 1 -C 6 )alkoxy and (C 3 - C 6 ) substituted (C 1 -C 6 )alkyl groups having on the chain 1 to 3 substituents each independently selected from the group consisting of cycloalkyl groups; (a9) (C 1 -C 6 )alkyl groups; carbonyl group; (a10) halo(C 1 -C 6 )alkylcarbonyl group; (a11) (C 3 -C 6 )cycl
• R 1 is (a2) (C 1 -C 6 )alkyl group; (a9) (C 1 -C 6 )alkylcarbonyl group; (a10) halo(C 1 -C 6 )alkylcarbonyl group; (a11) (C 3 -C) 6 ) Cycloalkylcarbonyl group; (a12) ( C1 - C6 )alkoxy( C1 - C6 )alkylcarbonyl group; (a13) ( C1 - C6 )alkylthio( C1 - C6 )alkylcarbonyl group (a14) a phenylcarbonyl group; (a15) 1 to 5 groups each independently selected from the group consisting of a halogen atom, a cyano group, a (C 1 -C 6 )alkyl group and a (C 1 -C 6 )alkoxy group; (a16) a thienylcarbonyl group; (a17)
• R 1 is (a9) (C 1 -C 6 ) alkylcarbonyl group; (a11) (C 3 -C 6 ) cycloalkylcarbonyl group; (a14) phenylcarbonyl group; (a15′) 1 each independently selected from a halogen atom (a20) (C 1 -C 6 )alkoxycarbonyl group; (a21) halo(C 1 -C 6 )alkoxycarbonyl group; (a22) (C 1 -C ( a25 ) ( C2 - C6 ) alkenyloxycarbonyl group; (a26) ( C2 - C6 ) alkynyloxycarbonyl group; ( a27 ) ( C3 —C 6 ) a cycloalkoxycarbonyl group; (a28) a phenyloxycarbonyl group; (a29′) a substituted phenyloxycarbonyl group having 1 to 3 substituents each independently
• R1 is (a1) hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C ( a6 ) halo(C1 - C6 )alkyl group; (a7) ( C1 - C6 )alkoxy group; (a8) cyano group, ( C1 - C6 )alkoxy and (C 3 -C 6 )cycloalkyl groups, substituted (C 1 -C 6 )alkyl groups having on the chain 1 to 3 substituents independently selected from the group consisting of (a9) (C (a10) halo( C1- C6 )alkylcarbonyl group; (a11) ( C3 - C6 )cycloalkylcarbonyl group; ( a12 ) ( C1 - C6 ) ( C1 - C6 ) al
• R11 is (i1) ( C1 - C6 )alkyl group; or (i2) ( C1 - C6 )alkoxy( C1 - C6 )alkyl group.
• Substituent group A is (e1) halogen atom; (e2) cyano group; ( e3) nitro group; (e4) hydroxyl group; (e5) carboxyl group; (e6) (C 1 -C 6 ) alkyl group; ( e8 ) ( C2- C6 ) alkynyl group; (e9) ( C1 - C6 ) alkoxy group; (e10) (C3 - C6 ) cycloalkyl group; (e11) ( (e12) ( C1 - C6 ) alkylsulfinyl group ; (e13) ( C1 - C6 ) alkylsulfonyl group; (e14 ) halo( C1 - C6 ) alkyl group.
• R 1 , R 11 and substituent group A are the same as in [19];
• R2 is (b5) a phenyl group;
• (b6) a substituted phenyl group having 1 to 5 substituents on the ring independently selected from Substituent Group A;
• (b7) a pyridyl group;
• (b8) from Substituent Group A a substituted pyridyl group having 1 to 4 independently selected substituents on the ring;
• (b14) a substituted pyrazinyl group
• R 1 is (a1) hydrogen atom; (a2) (C 1 -C 6 )alkyl group; (a9) (C 1 -C 6 )alkylcarbonyl group; (a10) halo(C 1 -C 6 )alkylcarbonyl group; (a11) ) (C 3 -C 6 ) cycloalkylcarbonyl group; (a12) (C 1 -C 6 )alkoxy(C 1 -C 6 )alkylcarbonyl group; (a13) (C 1 -C 6 )alkylthio(C 1 - ( a14 ) phenylcarbonyl group; (a15) independently selected from the group consisting of halogen atom, cyano group, ( C1 - C6 ) alkyl group and ( C1 - C6 ) alkoxy group; (a16) thienylcarbonyl group; (a17) halogen atom, cyano group, (C 1 - )
• R 1 is (a1) hydrogen atom; (a9) (C 1 -C 6 ) alkylcarbonyl group; (a11) (C 3 -C 6 ) cycloalkylcarbonyl group; (a14) phenylcarbonyl group; substituted phenylcarbonyl groups having 1 to 3 independently selected substituents; (a20) (C 1 -C 6 )alkoxycarbonyl groups; (a21) halo(C 1 -C 6 )alkoxycarbonyl groups; (a22) (a25 ) ( C2 - C6 )alkenyloxycarbonyl group ; (a26) ( C2 - C6 )alkynyloxycarbonyl group ; (a27) (C 3 -C 6 ) cycloalkoxycarbonyl group; (a28) phenyloxycarbonyl group; (a29') substituted phenyloxycarbonyl group having 1 to 3 substituents each independently selected from
• R 2 , R 11 and substituent group A are the same as in [19];
• R1 is (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 -C 6 ) cyclo (a6) halo(C 1 -C 6 )alkyl; (a7) (C 1 -C 6 )alkoxy; (a8) cyano, (C 1 -C 6 )alkoxy and (C 3 - C 6 ) substituted (C 1 -C 6 )alkyl groups having on the chain 1 to 3 substituents each independently selected from the group consisting of cycloalkyl groups; (a9) (C 1 -C 6 )alkyl groups; carbonyl group; (a10) halo(C 1 -C 6 )alkylcarbonyl group; (a11) (C 3 -
• R 1 is (a2) (C 1 -C 6 )alkyl group; (a9) (C 1 -C 6 )alkylcarbonyl group; (a10) halo(C 1 -C 6 )alkylcarbonyl group; (a11) (C 3 -C) 6 ) Cycloalkylcarbonyl group; (a12) ( C1 - C6 )alkoxy( C1 - C6 )alkylcarbonyl group; (a13) ( C1 - C6 )alkylthio( C1 - C6 )alkylcarbonyl group (a14) a phenylcarbonyl group; (a15) 1 to 5 groups each independently selected from the group consisting of a halogen atom, a cyano group, a (C 1 -C 6 )alkyl group and a (C 1 -C 6 )alkoxy group; (a16) a thienylcarbonyl group; (a17
• R 1 is (a9) (C 1 -C 6 ) alkylcarbonyl group; (a11) (C 3 -C 6 ) cycloalkylcarbonyl group; (a14) phenylcarbonyl group; (a15′) 1 each independently selected from a halogen atom (a20) (C 1 -C 6 )alkoxycarbonyl group; (a21) halo(C 1 -C 6 )alkoxycarbonyl group; (a22) (C 1 -C ( a25 ) ( C2 - C6 ) alkenyloxycarbonyl group; (a26) ( C2 - C6 ) alkynyloxycarbonyl group; ( a27 ) ( C3 —C 6 ) a cycloalkoxycarbonyl group; (a28) a phenyloxycarbonyl group; (a29′) a substituted phenyloxycarbonyl group having 1 to 3 substituents each independently
• R 1 is (a1) hydrogen atom; (a11) (C 3 -C 6 ) cycloalkylcarbonyl group; (a20) (C 1 -C 6 ) alkoxycarbonyl group; (a22) (C 1 -C 6 ) alkoxy (C 1 - (a33 ) N-(C 1 -C 6 )alkylaminocarbonyl group; (a34) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 ) the alkyls may be the same or different); (a40) N-(C 1 -C 6 )alkoxyaminocarbonyl group; (a41) N-(C 1 -C 6 )alkoxy(C 1 -C 6 ) (a42) N-(C 1 -C 6 )alkylthio(C 1 -C 6 )alkylaminocarbonyl group; (a45) pyrrol
• R1 is (a1) hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C ( a6 ) halo(C1 - C6 )alkyl group; (a7) ( C1 - C6 )alkoxy group; (a8) cyano group, ( C1 - C6 )alkoxy and (C 3 -C 6 )cycloalkyl groups, substituted (C 1 -C 6 )alkyl groups having on the chain 1 to 3 substituents independently selected from the group consisting of (a9) (C (a10) halo( C1- C6 )alkylcarbonyl group; (a11) ( C3 - C6 )cycloalkylcarbonyl group; ( a12 ) ( C1 - C6
• R11 is (i1) ( C1 - C6 )alkyl group; or (i2) ( C1 - C6 )alkoxy( C1 - C6 )alkyl group.
• Substituent group A is (e1) halogen atom; (e2) cyano group; ( e3) nitro group; (e4) hydroxyl group; (e5) carboxyl group; (e6) (C 1 -C 6 ) alkyl group; ( e8 ) ( C2- C6 ) alkynyl group; (e9) ( C1 - C6 ) alkoxy group; (e10) (C3 - C6 ) cycloalkyl group; (e11) ( (e12) ( C1 - C6 ) alkylsulfinyl group ; (e13) ( C1 - C6 ) alkylsulfonyl group; (e14 ) halo( C1 - C6 ) alkyl group.
• R 1 , R 11 and substituent group A are the same as in [27];
• R2 is (b5) a phenyl group;
• (b6) a substituted phenyl group having 1 to 5 substituents on the ring independently selected from Substituent Group A;
• (b7) a pyridyl group;
• (b8) from Substituent Group A a substituted pyridyl group having 1 to 4 independently selected substituents on the ring;
• (b14) a substituted pyrazinyl group
• R 1 is (a1) hydrogen atom; (a2) (C 1 -C 6 )alkyl group; (a9) (C 1 -C 6 )alkylcarbonyl group; (a10) halo(C 1 -C 6 )alkylcarbonyl group; (a11) ) (C 3 -C 6 ) cycloalkylcarbonyl group; (a12) (C 1 -C 6 )alkoxy(C 1 -C 6 )alkylcarbonyl group; (a13) (C 1 -C 6 )alkylthio(C 1 - ( a14 ) phenylcarbonyl group; (a15) independently selected from the group consisting of halogen atom, cyano group, ( C1 - C6 ) alkyl group and ( C1 - C6 ) alkoxy group; (a16) thienylcarbonyl group; (a17) halogen atom, cyano group, (C 1 - -
• R 1 is (a1) hydrogen atom; (a9) (C 1 -C 6 ) alkylcarbonyl group; (a11) (C 3 -C 6 ) cycloalkylcarbonyl group; (a14) phenylcarbonyl group; substituted phenylcarbonyl groups having 1 to 3 independently selected substituents; (a20) (C 1 -C 6 )alkoxycarbonyl groups; (a21) halo(C 1 -C 6 )alkoxycarbonyl groups; (a22) (a25 ) ( C2 - C6 )alkenyloxycarbonyl group ; (a26 ) ( C2 - C6 )alkynyloxycarbonyl group ; (a27) (C 3 -C 6 ) cycloalkoxycarbonyl group; (a28) phenyloxycarbonyl group; (a29') substituted phenyloxycarbonyl group having 1 to 3 substituents each independently selected from
• R 1 is (a1) is a hydrogen atom
• R2 is (b7) a pyridyl group; or (b8) a substituted pyridyl group having 1 to 4 substituents on the ring independently selected from substituent group A
• R11 is (i1) a ( C1 - C6 )alkyl group
• Substituent group A is (e2) the compound and salts thereof according to any one of [27] to [30], which is a cyano group; Regarding.
• the compounds of the present invention or salts thereof have excellent effects as insecticides. Moreover, it is effective not only against pests in the agricultural and horticultural field, but also against pests parasitic on pet animals such as dogs and cats, and livestock such as cattle and sheep.
• halo means "halogen atom"
• chlorine atom, bromine atom, iodine atom or fluorine atom indicates
• (C 1 -C 6 )alkyl group includes, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group and isopentyl group.
• tertiary pentyl group neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group and other linear or branched alkyl groups having 1 to 6 carbon atoms; .
• (C 2 -C 6 )alkenyl group includes, for example, vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2- linear or branched alkenyl groups having 2 to 6 carbon atoms such as propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group; and “(C 2 -C 6 )alkynyl group” includes, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl-1 -propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,3-
• (C 3 -C 6 )cycloalkyl group means a cyclic alkyl group having 3 to 6 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group
• (C 5 - C 6 ) Bridged cycloalkyl group means a bridged cycloalkyl group having 5 to 6 carbon atoms such as a bicyclo[1.1.1]pentanyl group and a bicyclo[2.1.1]hexyl group
• Examples of "(C 1 -C 6 )alkoxy group” include methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyl oxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-e
• Examples of the "(C 1 -C 6 )alkylthio group” include methylthio, ethylthio, normal-propylthio, isopropylthio, normal-butylthio, secondary-butylthio, tertiary-butylthio, normal-pentylthio, group, isopentylthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, isohexylthio group , a 1,1,2-trimethylpropylthio group or a straight or branched chain alkylthio group having 1 to 6 carbon atoms.
• Examples of "(C 1 -C 6 )alkylsulfinyl group” include methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, iso A linear or branched alkylsulfinyl group having 1 to 6 carbon
• (C 1 -C 6 )alkylsulfonyl group includes, for example, methylsulfonyl group, ethylsulfonyl group, normal propylsulfonyl group, isopropylsulfonyl group, normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, iso A linear or branched alkylsulfonyl group having 1 to 6 carbon
• (C 1 -C 6 )alkylcarbonyl group includes, for example, acetyl group, propanoyl group, butanoyl group, 2-methylpropanoyl group, pentanoyl group, 2-methylbutanoyl group, 3-methylbutanoyl group, An alkylcarbonyl group having 2 to 7 carbon atoms, such as an alkylcarbonyl group having the aforementioned (C 1 -C 6 )alkyl group such as pivaloyl group and hexanoyl group.
• (C 1 -C 6 )alkylcarbonylamino group means, for example, acetylamino group, propanoylamino group, butanoylamino group, 2-methylpropanoylamino group, pentanoylamino group, 2-methylbutanoyl alkylcarbonylamino groups having 2 to 7 carbon atoms, such as alkylcarbonylamino groups having the above (C 1 -C 6 )alkyl groups such as amino group, 3-methylbutanoylamino group, pivaloylamino group and hexanoylamino group; indicates
• Examples of "(C 1 -C 6 )alkylsulfonylamino group” include methylsulfonylamino group, ethylsulfonylamino group, normal propylsulfonylamino group, isopropylsulfonylamino group, normal butylsulfonylamino group and secondary butylsulfonylamino group.
• tertiary butylsulfonylamino group normal pentylsulfonylamino group, isopentylsulfonylamino group, tertiary pentylsulfonylamino group, neopentylsulfonylamino group, 2,3-dimethylpropylsulfonylamino group, 1-ethylpropylsulfonylamino group , 1-methylbutylsulfonylamino group, normalhexylsulfonylamino group, isohexylsulfonylamino group, 1,1,2-trimethylpropylsulfonylamino group, and other linear or branched C 1-6 alkyl groups Indicates a sulfonylamino group.
• N-(C 1 -C 6 )alkylaminocarbonyl group means, for example, N-methylaminocarbonyl group, N-ethylaminocarbonyl group, N-normalpropylaminocarbonyl group, N-isopropylaminocarbonyl group, N -normal butylaminocarbonyl group, N-isobutylaminocarbonyl group, N-secondary butylaminocarbonyl group, N-tertiary butylaminocarbonyl group, N-normalpentylaminocarbonyl group, N-isopentylaminocarbonyl group, N-tertia having a linear or branched alkyl group having 1 to 6 carbon atoms, such as a repentylaminocarbonyl group, N-neopentylaminocarbonyl group, N-normalhexylaminocarbonyl group, N-isohexylaminocarbonyl group; It represents an alky
• the "(C 1 -C 6 )alkoxycarbonyl group” includes, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, an isobutoxycarbonyl group, a secondary butoxycarbonyl group, An alkoxycarbonyl group having 2 to 7 carbon atoms, such as an alkoxycarbonyl group having the above (C 1 -C 6 )alkoxy group such as a tertiary butoxycarbonyl group and a pentyloxycarbonyl group.
• N-(C 1 -C 6 )alkylsulfamoyl group includes, for example, N-methylsulfamoyl group, N-ethylsulfamoyl group, N-normal-propylsulfamoyl group, N-isopropylsulfamoyl group, famoyl group, N-normal butylsulfamoyl group, N-isobutylsulfamoyl group, N-secondary butylsulfamoyl group, N-tertiary butylsulfamoyl group, N-normal pentylsulfamoyl group, N -isopentylsulfamoyl group, N-tertiarypentylsulfamoyl group, N-neopentylsulfamoyl group, N-(2,3-dimethylpropyl)sulfamoyl group, N-(
• N-(C 1 -C 6 )alkylaminosulfonyl group includes, for example, N-methylaminosulfonyl group, N-ethylaminosulfonyl group, N-normalpropylaminosulfonyl group, N-isopropylaminosulfonyl group, N -normal butylaminosulfonyl group, N-secondary butylaminosulfonyl group, N-tertiary butylaminosulfonyl group, N-normal pentylaminosulfonyl group, N-isopentylaminosulfonyl group, N-tertiary pentylaminosulfonyl group, N -neopentylaminosulfonyl group, N-(2,3-dimethylpropyl)aminosulfonyl group, N-(1-ethylpropyl)aminosulfonyl group, N-(1-(
• N,N-di(C 1 -C 6 )alkylaminosulfonyl group includes, for example, N,N-dimethylaminosulfonyl group, N,N-diethylaminosulfonyl group, N,N-di-n-propylaminosulfonyl group , N,N-diisopropylaminosulfonyl group, N,N-di-normalbutylaminosulfonyl group, N,N-dis-secondary-butylaminosulfonyl group, N,N-ditert-butylaminosulfonyl group, N-methyl-N-ethyl aminosulfonyl group, N-methyl-N-normal-propylaminosulfonyl group, N-methyl-N-isopropylaminosulfonyl group, N-methyl-N-normal-butylaminosulfonyl group, N-methyl-N-
• Halo(C 1 -C 6 )alkyl group "Halo(C 2 -C 6 )alkenyl group", “Halo(C 2 -C 6 )alkynyl group”, “Halo(C 1 -C 6 ) alkoxy group”, "halo( C1 - C6 )alkylthio group”, “halo( C1 - C6 )alkylsulfinyl group”, “halo( C1 - C6 )alkylsulfonyl group”, “halo( C3 —C 6 )cycloalkyl group”, “halo(C 1 -C 6 )alkylcarbonylamino group”, “halo(C 1 -C 6 )alkylsulfonylamino group”, “N-halo(C 1 -C 6 ) "alkylaminocarbonyl group” and the like.
• Aryl group refers to, for example, an aromatic hydrocarbon group having 6 to 10 carbon atoms such as a phenyl group, 1-naphthyl group, and 2-naphthyl group.
• the "5- to 10-membered heterocyclic group” is a 5- or 6-membered monocyclic aromatic ring containing 1 to 4 heteroatoms selected from oxygen atoms, sulfur atoms and nitrogen atoms in addition to carbon atoms as ring-constituting atoms.
• heterocyclic group an aromatic condensed heterocyclic group in which the monocyclic aromatic heterocycle is fused with a benzene ring or a monocyclic aromatic ring, a 4- to 6-membered monocyclic non-aromatic heterocyclic group, or the A non-aromatic condensed heterocyclic group in which a monocyclic non-aromatic heterocyclic ring is fused with a benzene ring or a monocyclic aromatic ring, and the like.
• a ring-constituting atom of the 5- to 10-membered heterocyclic group may be oxidized with an oxo group.
• “Monocyclic aromatic heterocyclic group” includes, for example, furyl group, thienyl group, pyridyl group, oxopyridyl group (e.g., 1,6-dihydro-6-oxo-1H-pyridyl group), pyrimidinyl group, pyridazinyl group, pyrazinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, oxopyrazolyl group (e.g., 4,5-dihydro-5-oxo-1H-pyrazolyl group), thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, isoxazolyl group, oxadiazolyl group (e.g., 1,3,4-oxadiazolyl group, 1,2,4-oxadiazolyl group), thiadiazolyl group (e.g., 1,3,4-thiadiazoly
• the "monocyclic non-aromatic heterocyclic group” includes, for example, oxetanyl, thietanyl, azetidinyl, pyrrolidinyl, pyrrolidinyl-2-one, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, hexamethyleneyl, minyl group, oxazolidinyl group, thiazolidinyl group, imidazolidinyl group, oxazolinyl group, thiazolinyl group, isoxazolinyl group, imidazolinyl group, dioxolyl group, dioxolanyl group, dihydrooxadiazolyl group, 2-oxo-pyrrolidin-1-yl group, 2-oxo pyridin-4-yl group, 2,4-dioxopyrimidin-5-yl group, 2-oxo-1,3-oxazo
• R 3 and R 4 may combine with each other to form a ring.
• the "ring” include 3- to 7-membered nitrogen-containing heterocycles such as aziridine, azetidine, pyrrolidine, piperidine, homopiperidine, piperazine, homopiperazine, morpholine and homomorpholine.
• the nitrogen-containing heterocycle may be condensed with a benzene ring.
• the nitrogen-containing heterocyclic ring and benzene ring are substituted with 1 to 6 substituents selected from the group consisting of halogen atoms, (C 1 -C 6 )alkyl groups, halo(C 1 -C 6 )alkyl groups and the like. may be
• Examples of the salts of the compounds represented by the general formulas (1), (2), (3) and (21) of the present invention include inorganic acid salts such as hydrochlorides, sulfates, nitrates and phosphates, and acetates. , fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and other organic acid salts, sodium ion, potassium ion, magnesium ion, calcium ion, trimethylammonium, etc. Salts with inorganic or organic bases can be exemplified.
• the compounds represented by general formulas (1), (2), (3) and (21) of the present invention and salts thereof may have one or more asymmetric centers in their structural formulas. , two or more optical isomers and diastereomers may exist, and the present invention encompasses each optical isomer and mixtures thereof in any ratio.
• the compounds represented by the general formulas (1), (2), (3) and (21) of the present invention and their salts contain two types of carbon-carbon double bond-derived compounds in their structural formulas.
• geometric isomers may exist, the present invention includes all geometric isomers and mixtures thereof in any proportion.
• the compounds represented by the general formulas (1), (2), (3), and (21) of the present invention and their salts may have multiple tautomers. includes all tautomers and mixtures thereof in any proportion.
• R 1 includes the above (a1), (a2), (a9), (a10), (a11), (a12), (a13), (a14), (a15), (a16), (a17), (a18), (a19), (a20), (a21), (a22), (a23), (a24), (a25), (a26), (a27), (a28 ), (a29), (a30), (a31), (a32), (a33), (a34), (a35), (a36), (a37), (a38), (a39), (a40), (a41), (a42), (a43), (a44), (a45), (a46), (a47), (a48), (a49), (a54), (a55), (a61), (a67 ), (a68), (a69), (a70), (a71), (a72), (a73), (a74), (a75), (a76), (a77), (a78), (a81), or (a82) group is
• R 1 is the above (a2), (a3), (a4), (a5), (a6), (a7), (a8), (a9) , (a10), (a11), (a12), (a13), (a14), (a15), (a16), (a17), (a18), (a19), (a20), (a21), ( a22), (a23), (a24), (a25), (a26), (a27), (a28), (a29), (a30), (a31), (a32), (a33), (a34) , (a35), (a36), (a37), (a38), (a39), (a40), (a41), (a42), (a43), (a44), (a45), (a46), ( a47), (a48), (a49), (a50), (a51), (a52), (a53), (a54), (a55), (a56), (a57), (a58), (a59) , (a60
• R 2 includes the above (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26 ), (b27), (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b46), (b47), (b48), (b49), (b50), (b51 ), (b52), (b53), (b54), (b55), (b56), (b57), (b58), (b59), (b60), (b61), (b62), (b63), (b64), (b65
• R 3 is preferably the above group (c1), (c2), (c3), (c4), or (c5), Group (c1) or (c2) above is more preferred.
• R 4 includes the above (d1), (d2), (d3), (d4), (d5), (d6), (d7), (d8), (d9), (d10), (d11), (d14), (d15), (d16), (d17), (d18), (d19), (d20), (d21), (d22), (d23), (d24 ), (d25), (d32), (d33), (d36), (d37), (d40), (d41), (d42), (d43), (d54), (d55), (d58), (d59), (d60), (d61), (d62), (d63), (d64), (d65), (d70), (d71), (d72), (d73), (d74), (d75 ), (d76), or (d77) groups are preferred, (d1), (d2), (d4), (d8), (d10), (d11), (d14), (d15), (d16), (d17), (d77), (d
• X is an oxygen atom and Y is an oxygen atom. Moreover, in the general formula (1), it is also preferable that X is an oxygen atom and Y is a sulfur atom. Moreover, in the general formula (1), it is also preferable that X is a sulfur atom and Y is an oxygen atom.
• Z is an OR 5 group (wherein R 5 is a hydrogen atom, (C 1 -C 6 )alkyl group, or (C 1 -C 6 )alkoxy(C 1 -C 6 ) alkyl group), S(O)nR 6 group (wherein n is 0, 1 or 2, R 6 is a hydrogen atom, (C 1 -C 6 ) alkyl group, (C 1 - C 6 )alkoxy(C 1 -C 6 )alkyl group or phenyl(C 1 -C 6 )alkyl group), or N(R 7 )R 8 group (wherein R 7 and R 8 are hydrogen atom, hydroxyl group, (C 1 -C 6 )alkyl group, (C 1 -C 6 )alkoxy group, or N-phenylamino group, and R 7 and R 8 may be the same or different) is preferably OR 5 group (wherein R 5 represents a hydrogen atom or (C 1 -C 6 )alkyl group
• the substituent group A includes the above (e1), (e2), (e6), (e7), (e8), (e9), (e10), (e11), (e12 ), (e13), (e14), (e17), (e19), (e20), (e21), (e22), (e26), (e27), (e32), (e33), (e36), (e37), (e40), (e41), (e42), (e43), (e44), (e45), (e46), (e47), (e50), (e51), (e54), (e55 ), (e58), (e59), (e60), (e61), (e74), (e75), (e76), (e77), (e80), (e81), (e87), (e88), preferably consisting of the groups (e89), (e92), (e93) and (e94), (e1), (e2), (e6), (e8), (e9), (e10), (e11), (e13), (e14),
• the substituent group B may consist of the above groups (f1), (f2), (f3), (f4), (f5), (f6), and (f12). preferably It is more preferable to consist of the above groups (f3), (f4) and (f12).
• the substituent group C preferably consists of the above groups (g1), (g2), (g10), and (g17).
• the substituent group D includes the above (h1), (h2), (h3), (h7), (h8), (h9), (h10), (h11), (h12 ), (h13), (h14), (h16), (h17), (h18), (h19), (h23), (h24), (h25) and (h26) groups, (h1), (h2), (h3), (h7), (h8), (h10), (h12), (h13), (h14), (h16), (h19), (h23), More preferably, it consists of groups (h24) and (h25).
• R 1 includes (a1), (a2), (a9), (a10), (a11), (a12), (a13), (a14), (a15), (a16 ), (a17), (a18), (a19), (a20), (a21), (a22), (a23), (a24), (a25), (a26), (a27), (a28), (a29), (a30), (a31), (a32), (a33), (a34), (a35), (a36), (a37), (a38), (a39), (a40), (a41 ), (a42), (a43), (a44), (a45), (a46), (a47), (a48), (a49), (a54), (a55), (a61), (a67), (a68), (a69), (a70), (a71), (a72), (a73), (a74), (a75), (a76), (a77), (a78), (a81), or ( a82) groups are preferred.
• R 1 is the above (a2), (a3), (a4), (a5), (a6), (a7), (a8), (a9) , (a10), (a11), (a12), (a13), (a14), (a15), (a16), (a17), (a18), (a19), (a20), (a21), ( a22), (a23), (a24), (a25), (a26), (a27), (a28), (a29), (a30), (a31), (a32), (a33), (a34) , (a35), (a36), (a37), (a38), (a39), (a40), (a41), (a42), (a43), (a44), (a45), (a46), ( a47), (a48), (a49), (a50), (a51), (a52), (a53), (a54), (a55), (a56), (a57), (a58), (a59) , (a60
• R 2 includes the above (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26 ), (b27), (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b46), (b47), (b48), (b49), (b50), (b51 ), (b52), (b53), (b54), (b55), (b56), (b57), (b58), (b59), (b60), (b61), (b62), (b63), (b64), (b65
• the substituent group A includes the above (e1), (e2), (e6), (e7), (e8), (e9), (e10), (e11), (e12 ), (e13), (e14), (e17), (e19), (e20), (e21), (e22), (e26), (e27), (e32), (e33), (e36), (e37), (e40), (e41), (e42), (e43), (e44), (e45), (e46), (e47), (e50), (e51), (e54), (e55 ), (e58), (e59), (e60), (e61), (e74), (e75), (e76), (e77), (e80), (e81), (e87), (e88), preferably consisting of the groups (e89), (e92), (e93) and (e94), (e1), (e2), (e6), (e8), (e9), (e10), (e11), (e13), (e14),
• R 1 includes (a1), (a2), (a9), (a10), (a11), (a12), (a13), (a14), (a15), (a16 ), (a17), (a18), (a19), (a20), (a21), (a22), (a23), (a24), (a25), (a26), (a27), (a28), (a29), (a30), (a31), (a32), (a33), (a34), (a35), (a36), (a37), (a38), (a39), (a40), (a41 ), (a42), (a43), (a44), (a45), (a46), (a47), (a48), (a49), (a54), (a55), (a61), (a67), (a68), (a69), (a70), (a71), (a72), (a73), (a74), (a75), (a76), (a77), (a78), (a81), or ( a82) groups are preferred.
• R 1 is the above (a2), (a3), (a4), (a5), (a6), (a7), (a8), (a9) , (a10), (a11), (a12), (a13), (a14), (a15), (a16), (a17), (a18), (a19), (a20), (a21), ( a22), (a23), (a24), (a25), (a26), (a27), (a28), (a29), (a30), (a31), (a32), (a33), (a34) , (a35), (a36), (a37), (a38), (a39), (a40), (a41), (a42), (a43), (a44), (a45), (a46), ( a47), (a48), (a49), (a50), (a51), (a52), (a53), (a54), (a55), (a56), (a57), (a58), (a59) , (a60
• R 2 includes the above (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26 ), (b27), (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b46), (b47), (b48), (b49), (b50), (b51 ), (b52), (b53), (b54), (b55), (b56), (b57), (b58), (b59), (b60), (b61), (b62), (b63), (b64), (b65
• R 11 is preferably (i1) (C 1 -C 6 )alkyl group.
• the substituent group A includes the above (e1), (e2), (e6), (e7), (e8), (e9), (e10), (e11), (e12 ), (e13), (e14), (e17), (e19), (e20), (e21), (e22), (e26), (e27), (e32), (e33), (e36), (e37), (e40), (e41), (e42), (e43), (e44), (e45), (e46), (e47), (e50), (e51), (e54), (e55 ), (e58), (e59), (e60), (e61), (e74), (e75), (e76), (e77), (e80), (e81), (e87), (e88), preferably consisting of the groups (e89), (e92), (e93) and (e94), (e1), (e2), (e6), (e8), (e9), (e10), (e11), (e13), (e14),
• R 1 includes (a1), (a2), (a9), (a10), (a11), (a12), (a13), (a14), (a15), (a16 ), (a17), (a18), (a19), (a20), (a21), (a22), (a23), (a24), (a25), (a26), (a27), (a28), (a29), (a30), (a31), (a32), (a33), (a34), (a35), (a36), (a37), (a38), (a39), (a40), (a41 ), (a42), (a43), (a44), (a45), (a46), (a47), (a48), (a49), (a54), (a55), (a61), (a67), (a68), (a69), (a70), (a71), (a72), (a73), (a74), (a75), (a76), (a77), (a78), (a81), or ( a82) groups are
• R 2 includes the above (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26 ), (b27), (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b46), (b47), (b48), (b49), (b50), (b51 ), (b52), (b53), (b54), (b55), (b56), (b57), (b58), (b59), (b60), (b61), (b62), (b63), (b64), (b5), (b60
• R 11 is preferably (i1) (C 1 -C 6 )alkyl group.
• the substituent group A includes the above (e1), (e2), (e6), (e7), (e8), (e9), (e10), (e11), (e12 ), (e13), (e14), (e17), (e19), (e20), (e21), (e22), (e26), (e27), (e32), (e33), (e36), (e37), (e40), (e41), (e42), (e43), (e44), (e45), (e46), (e47), (e50), (e51), (e54), (e55 ), (e58), (e59), (e60), (e61), (e74), (e75), (e76), (e77), (e80), (e81), (e87), (e88), preferably consisting of the groups (e89), (e92), (e93) and (e94), (e1), (e2), (e6), (e8), (e9), (e10), (e11), (e) (e
• Manufacturing method 1 The compounds represented by the general formulas (1-1) and (1-2) of the present invention can be produced from the compound represented by the general formula (3-1) by the following steps [a] and [b]. can be done.
• R 1 , R 2 , R 3 , R 4 and R 11 are the same as above.
• L represents, for example, a leaving group such as chlorine, bromine, (C 1 -C 6 )alkoxycarbonyloxy group.
• step [a] The compound represented by general formula (3-1) is reacted with the compound represented by general formula (4) in the presence of an inert solvent to obtain the general formula (1) of the present invention. -1) can be produced.
• the inert solvent used in this reaction may be one that does not significantly hinder the progress of this reaction.
• Examples include linear or cyclic saturated hydrocarbons such as pentane, hexane and cyclohexane, Chains of aromatic hydrocarbons, halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc.
• inert solvents such as amorphous or cyclic ethers, nitriles such as acetonitrile and propionitrile, esters such as methyl acetate, ketones such as acetone and methyl ethyl ketone, N,N-dimethylformamide, N,N-dimethylacetamide, Aprotic polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, propanol, butanol and 2-propanol; They can be used singly or in combination of two or more.
• the amount to be used may be appropriately selected from the range of usually 0.1 to 100 L per 1 mol of the compound represented by general formula (3-1).
• reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. It should be selected as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary. Alternatively, it can be subjected to the next step without isolation.
• step [b] By reacting a compound represented by general formula (1-1) with a compound represented by general formula (5) in the presence of a base and an inert solvent, the general formula of the present invention is obtained.
• a compound represented by (1-2) can be produced.
• Examples of the base that can be used in this reaction include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, hydrides of alkali metal atoms such as sodium hydride and potassium hydride, sodium ethoxide, potassium t- Alkali metal salts of alcohols such as butoxide; inorganic bases such as carbonates such as sodium carbonate, potassium carbonate and sodium hydrogen carbonate; organic bases such as triethylamine, pyridine, N,N-dimethyl-4-aminopyridine and DBU; The amount used is generally in the range of 1 to 10 mol per mol of the compound represented by formula (1-1).
• the inert solvent that can be used in this reaction may be one that does not significantly hinder the progress of this reaction.
• inert solvents such as amorphous or cyclic ethers, nitriles such as acetonitrile and propionitrile, esters such as methyl acetate, ketones such as acetone and methyl ethyl ketone, N,N-dimethylformamide, N,N-dimethylacetamide, Aprotic polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, propanol, butanol and 2-propanol; They can be used singly or in combination of two or more.
• the amount to be used may be appropriately selected from the range of usually 0.1 to 100 L per 1 mol of the compound represented by formula (1-1).
• reaction temperature in this reaction may generally be in the range of 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary.
• Manufacturing method 2 The compound represented by general formula (1-3) of the present invention can be produced from the compound represented by general formula (1-1) by the following step [c].
• R 2 , R 3 and R 4 are the same as above.
• Q represents an oxygen atom or a sulfur atom.
• R 1' is a hydrogen atom, (C 1 -C 6 )alkyl group, halo(C 1 -C 6 )alkyl group, (C 2 -C 6 )alkenyl group, (C 2 -C 6 )alkynyl group, ( C 3 -C 6 )cycloalkyl group, (C 1 -C 6 )alkoxy group, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group, (C 1 -C 6 )alkylthio(C 1 - 1 to 5 independently selected from the group consisting of C 6 )alkyl groups, phenyl(C 1 -C 6 )alkyl groups, halogen atoms, cyano groups, nitro groups and (C 1 -C 6 )alkyl groups; substituted phenyl
• step [c] By reacting a compound represented by general formula (1-1) with a compound represented by general formula (6) in the presence of a base and an inert solvent, the general formula of the present invention is obtained.
• a compound represented by (1-3) can be produced.
• Bases that can be used in this reaction include, for example, hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide. alkoxides such as side, alkali metal hydrides such as sodium hydride and potassium hydride, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate, cesium carbonate, etc.
• hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide.
• alkoxides such as side
• alkali metal hydrides such as sodium hydride and potassium hydride
• lithium carbonate lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate
• Acetates such as carbonates, lithium acetate, sodium acetate and potassium acetate, organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and N,N-diisopropylethylamine, etc., and the amount used is determined by the general formula: It is usually used in the range of 1 to 10 times the molar amount of the compound represented by (1-1).
• the inert solvent that can be used in this reaction may be one that does not significantly hinder the progress of this reaction.
• inert solvents such as amorphous or cyclic ethers, nitriles such as acetonitrile and propionitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolidinone, etc. and alcohols such as methanol, ethanol, propanol, butanol and 2-propanol.
• inert solvents can be used alone or in combination of two or more.
• the amount to be used may be appropriately selected from the range of usually 0.1 to 100 L per 1 mol of the compound represented by formula (1-1).
• reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. It should be selected as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary.
• Manufacturing method 3 The compound represented by general formula (1-3) of the present invention can be produced from the compound represented by general formula (1-1) by the following step [d].
• R 2 , R 3 and R 4 are the same as above.
• Q represents an oxygen atom or a sulfur atom.
• L represents, for example, a leaving group such as chlorine, bromine, imidazolyl group or trichloromethoxy group.
• R 1′ is the same as above and may be the same or different.
• a compound represented by general formula (1-1) is treated with a compound represented by general formula (7) and general formula (8) in the presence or absence of an inert solvent and a base.
• a compound represented by the general formula (1-3) can be produced by reacting it with a reactant with the represented compound.
• Bases that can be used in this reaction include, for example, hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide. alkoxides such as side, alkali metal hydrides such as sodium hydride and potassium hydride, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate, cesium carbonate, etc.
• hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide.
• alkoxides such as side
• alkali metal hydrides such as sodium hydride and potassium hydride
• lithium carbonate lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate
• Acetates such as carbonates, lithium acetate, sodium acetate and potassium acetate, organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and N,N-diisopropylethylamine, etc., and the amount used is determined by the general formula: It is usually used in the range of 1 to 10 times the molar amount of the compound represented by (1-1).
• the inert solvent that can be used in this reaction may be one that does not significantly hinder the progress of this reaction.
• the amount to be used may be appropriately selected from the range of usually 0.1 to 100 L per 1
• reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. It should be selected as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary.
• Manufacturing method 4 The compound represented by general formula (1-4) of the present invention can be produced from the compound represented by general formula (2) by the following step [c].
• the reaction conditions for [c] are the same as above.
• n' is 1 or 2;
• L represents, for example, a leaving group such as chlorine, bromine or iodine.
• a compound represented by general formula (1-5) is produced by reacting a compound represented by general formula (1-4) with a sulfurizing agent in the presence of an inert solvent. be able to.
• Sulfurizing agents that can be used in this reaction include, for example, Lawesson's Reagent and phosphorus pentasulfide. is usually used in the range of 1.0 to 10 times the molar amount.
• This reaction may or may not use a solvent, but the solvent that can be used in this reaction may be any solvent that does not significantly hinder the progress of this reaction.
• aromatic hydrocarbons such as cyclic saturated hydrocarbons, benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; diethyl ether; inert solvents such as cyclic ethers; nitriles such as acetonitrile and propionitrile; Examples include protic polar solvents, alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, and these inert solvents can be used alone or in combination of two or more.
• the amount to be used may be appropriately selected from the range of usually 0.1 to 100 L per 1 mol of the compound represented by formula (1-4).
• the reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. It should be selected as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary. Alternatively, it can be subjected to the next step without isolation.
• a compound represented by general formula (1-7) is produced by reacting a compound represented by general formula (1-6) with an oxidizing agent in the presence of an inert solvent. be able to.
• oxidizing agent examples include hydrogen peroxide solution, perbenzoic acid, and peroxides such as meta-chloroperbenzoic acid. It can be appropriately selected from the range of 1 to 5 times the molar amount of the compound represented by 6).
• the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction. , methylene chloride, chloroform, carbon tetrachloride and other halogenated hydrocarbons; chlorobenzene, dichlorobenzene and other halogenated aromatic hydrocarbons; acetonitrile and other nitriles; ethyl acetate and other esters; Polar solvents such as acids, N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, and water can be mentioned. A mixture of the above can be used.
• the amount of the inert solvent to be used is not particularly limited as long as it is an amount capable of dissolving the reaction reagent. good.
• the reaction temperature in this reaction may be appropriately selected from the range of -10°C to the reflux temperature of the inert solvent used.
• the reaction time varies depending on the scale of reaction, reaction temperature, etc., and may be appropriately selected from the range of several minutes to 48 hours.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, or the like.
• Manufacturing method 7 The compound represented by general formula (1-3) of the present invention can be produced from the compound represented by general formula (3-2) by the following step [a].
• the reaction conditions for [a] are the same as above.
• R 2 , R 3 , R 4 and R 11 are the same as above.
• Q represents an oxygen atom or a sulfur atom.
• R 1' is a hydrogen atom, (C 1 -C 6 )alkyl group, halo(C 1 -C 6 )alkyl group, (C 2 -C 6 )alkenyl group, (C 2 -C 6 )alkynyl group, ( C 3 -C 6 )cycloalkyl group, (C 1 -C 6 )alkoxy group, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group, (C 1 -C 6 )alkylthio(C 1 - 1 to 5 independently selected from the group consisting of C 6 )alkyl groups, phenyl(C 1 -C 6 )alkyl groups, halogen atoms, cyano groups, nitro groups and (C 1 -C 6 )alkyl groups; substituted
• R 1 , R 2 and R 11 are the same as above.
• L represents, for example, a leaving group such as chlorine, bromine, (C 1 -C 6 )alkoxycarbonyloxy group.
• R' represents, for example, a (C 1 -C 6 )alkyl group such as a methyl group or an ethyl group, or a phenyl group, and may be the same or different.
• R'' represents, for example, a (C 1 -C 6 )alkyl group such as a methyl group or an ethyl group.
• step [g] A compound represented by the general formula (11) is reacted with sodium nitrite in concentrated hydrochloric acid, and then reduced with a reducing agent to obtain a compound represented by the general formula (12). can be manufactured.
• reducing agent used in this reaction for example, sodium sulfite, tin chloride, etc. can be exemplified. It may be used by appropriately selecting from the range of 10-fold moles.
• the reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. It should be selected as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary. Alternatively, it can be subjected to the next step without isolation.
• step [h] A compound represented by the general formula (12) is reacted with a compound represented by the formula (13) in the presence or absence of an acid in the presence of an inert solvent to obtain a compound represented by the general formula ( 14) can be produced.
• Examples of the acid used in this reaction include carboxylic acids such as formic acid, acetic acid, propionic acid and trifluoroacetic acid, and sulfonic acids such as methanesulfonic acid, p-toluenesulfonic acid and trifluoromethylsulfonic acid.
• carboxylic acids such as formic acid, acetic acid, propionic acid and trifluoroacetic acid
• sulfonic acids such as methanesulfonic acid, p-toluenesulfonic acid and trifluoromethylsulfonic acid.
• the amount used is usually in the range of 1.0 to 10 mol per 1 mol of the compound represented by the general formula (12).
• the inert solvent used in this reaction may be one that does not significantly hinder the progress of this reaction.
• Examples include linear or cyclic saturated hydrocarbons such as pentane, hexane and cyclohexane, Chains of aromatic hydrocarbons, halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc.
• inert solvents such as amorphous or cyclic ethers, nitriles such as acetonitrile and propionitrile, esters such as methyl acetate, ketones such as acetone and methyl ethyl ketone, N,N-dimethylformamide, N,N-dimethylacetamide, Aprotic polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, propanol, butanol and 2-propanol; They can be used singly or in combination of two or more.
• the amount to be used may be appropriately selected from the range of usually 0.1 to 100 L per 1 mol of the compound represented by the general formula (12).
• reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. It should be selected as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary. Alternatively, it can be subjected to the next step without isolation.
• step [i] The compound represented by the general formula (14) is reacted with the compound represented by the general formula (15) in the presence of a base and an inert solvent to obtain the compound represented by the general formula (16). can be produced.
• Examples of the base used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide, Examples include alkoxides such as side, alkali metal hydrides such as sodium hydride and potassium hydride, and the amount used is usually 1 to 10 times the molar amount of the compound represented by the general formula (14). used in the range of
• the inert solvent used in this reaction may be one that does not significantly hinder the progress of this reaction.
• Examples include linear or cyclic saturated hydrocarbons such as pentane, hexane and cyclohexane, Aromatic hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, acetonitrile, propionitrile Nitriles such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone.
• the active solvent can be used alone or in combination of two or more. The amount to be used may be appropriately selected from the range of usually 0.1 to 100 L per 1 mol of the compound represented by the
• reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. It should be selected as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary. Alternatively, it can be subjected to the next step without isolation.
• a compound represented by the general formula (17) can be produced by hydrolyzing the compound represented by the general formula (16) in the presence of an acid and an inert solvent.
• Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid; carboxylic acids such as formic acid, acetic acid, propionic acid and trifluoroacetic acid; methanesulfonic acid, p-toluenesulfonic acid, trifluoromethylsulfone; Sulfonic acids such as acids can be mentioned, and the amount thereof to be used is usually in the range of 1.0 to 10 mol per 1 mol of the compound represented by the general formula (16).
• the inert solvent used in this reaction may be one that does not significantly hinder the progress of this reaction.
• Examples include linear or cyclic saturated hydrocarbons such as pentane, hexane and cyclohexane, Aromatic hydrocarbons, methylene chloride, chloroform, carbon tetrachloride and other halogenated hydrocarbons, chlorobenzene, dichlorobenzene and other halogenated aromatic hydrocarbons, diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, 2- inert solvents such as linear or cyclic ethers such as methyltetrahydrofuran, nitriles such as acetonitrile and propionitrile, esters such as methyl acetate, ketones such as acetone and methyl ethyl ketone, N,N-dimethylformamide, N, Aprotic polar solvents such as N-dimethylacetamide,
• the reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. It should be selected as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary. Alternatively, it can be subjected to the next step without isolation.
• step [k] The compound represented by the general formula (17) and the compound represented by the general formula (18) are condensed by an amidation method commonly used in organic synthesis to obtain the compound represented by the general formula ( 19) can be produced.
• a compound represented by general formula (3-1) is produced by subjecting a compound represented by general formula (19) to a cyclization reaction in the presence of a base and an inert solvent. be able to.
• Examples of the base used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide, alkoxides such as side; alkali metal hydrides such as sodium hydride and potassium hydride; carbonates such as lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate and magnesium carbonate; Acetates such as lithium acetate, sodium acetate, and potassium acetate, organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and diisopropylethylamine, and the like, and the amount used is represented by the general formula (19). It is usually used in the range of 1 to 10 times the molar amount of the compound.
• the inert solvent used in this reaction may be one that does not significantly hinder the progress of this reaction.
• Examples include linear or cyclic saturated hydrocarbons such as pentane, hexane and cyclohexane, Aromatic hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, acetonitrile, propionitrile Nitriles such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone, methanol, ethanol, propanol, butanol, 2 -Alcohols such as propanol can be mentioned, and these inert solvents can be used alone or
• the reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. It should be selected as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary.
• a compound represented by general formula (2-1) is produced by reacting a compound represented by general formula (3-1) under heating conditions in the presence of an inert solvent. be able to.
• the inert solvent used in this reaction may be one that does not significantly hinder the progress of this reaction.
• Examples include linear or cyclic saturated hydrocarbons such as pentane, hexane and cyclohexane, Aromatic hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, acetonitrile, propionitrile Nitriles such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone, methanol, ethanol, propanol, butanol, 2 -Alcohols such as propanol, water, etc. can be exemplified, and these in
• the reaction temperature in this reaction may generally be in the range of about 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. It should be selected as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary. Alternatively, it can be subjected to the next step without isolation.
• R 1 , R 2 and R 11 are the same as above.
• L represents, for example, a leaving group such as chlorine, bromine, (C 1 -C 6 )alkoxycarbonyloxy group.
• R 2 and R 11 are the same as above.
• Q represents an oxygen atom or a sulfur atom.
• R 1' is a hydrogen atom, (C 1 -C 6 )alkyl group, halo(C 1 -C 6 )alkyl group, (C 2 -C 6 )alkenyl group, (C 2 -C 6 )alkynyl group, ( C 3 -C 6 )cycloalkyl group, (C 1 -C 6 )alkoxy group, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group, (C 1 -C 6 )alkylthio(C 1 - 1 to 5 each independently selected from the group consisting of C 6 )alkyl groups, phenyl(C 1 -C 6 )alkyl groups, halogen atoms, cyano groups, nitro groups and (C 1 -C 6 )alkyl groups; Substituted phenyl
• R 2 and R 11 are the same as above.
• R'' represents, for example, a (C 1 -C 6 )alkyl group such as a methyl group or an ethyl group.
• Agricultural and horticultural insecticides containing the compound represented by the general formula (1) of the present invention or a salt thereof as an active ingredient are various agricultural and forestry, horticultural and grain storage insect pests that damage paddy rice, fruit trees, vegetables, other crops and flowering plants. It is suitable for pest control such as sanitary pests and nematodes.
• the agricultural and horticultural insecticide containing the compound represented by the general formula (1) of the present invention or a salt thereof as an active ingredient has physical properties suitable for various labor-saving application methods, systemic activity, suitable soil Excellent environmental safety such as persistence.
• the agricultural and horticultural insecticide containing the compound represented by the general formula (1) of the present invention or a salt thereof as an active ingredient has an effect on natural enemies, useful insects such as honeybees and bumblebees, and environmental organisms such as midges. Less is.
• Lepidoptera pests such as Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapularis, Spodoptera exempta, and American white chick (Hyphantria cunea), Ostrinia furnacalis, Pseudaletia separata, Tinea translucens, Bactra furfuryla, Parnara guttata, Marasmia exigua, Sesamia inferens, Imokibaga (Brachmia triannulella), Monema flavescens, Trichoplusia ni, Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Cephonodes hylas, Helicoverpa armigera , Phalerodonta manleyi, Eumeta
• Hemiptera pests such as Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, etc.
• Aeschynteles maculatus Creontiades pallidifer, Dysdercus cingulatus, Chrysophalus ficus, Aonidiella aurantii, Graptopsaltria nigrofuscata, Blissusleucopter us), Iselya Scale insect (Icerya purchasi), Japanese stink bug (Piezodorus hybneri), Rice stink bug (Lagynotomus elongatus), Rice leafhopper (Thaia subrufa), Rice black stink bug (Scotinophara lurida), Thorny aphid (Sitobion ibarae), Stink bug (Stariodes iwa) sakii) , Aspidiotus destructor,
• Coleoptera pests such as Xystrocera globosa, Paederus fuscipes, Eucetonia roelofsi, Callosobruchus chinensis, Cylas formicarius, Alfalfa weevil (Hypera postica), rice weevil (Echinocnemus squameus), rice weevil (Oulema oryzae), rice leaf beetle (Donacia proposti), rice water weevil (Lissorhoptrus oryzophilus), colasposoma dauricum, potato weevil (Euscepes postfasciatus), kidney beetle (E) pilachna varivestis), kidney bean Weevil (Acanthoscelides obtectus), Western corn rootworm (Diabrotica virgifera virgifera), Plum weevil (Involvulus cupreus), Cucumber beetle (Aulacophora femoralis), Pe
• Diptera pests such as Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, and rice flies Hydrellia sasakii, Agromyza oryzae, Hydrellia griseola, Ophiomyia phaseoli, Dacus cucurbitae, Drosophila suzukii, Rhaco chlaena japonica ), Muscina stabulans, Megaselia spiralis and other flea flies, Clogmia albipunctata, Tipula aino, Phormia regina, Culex tritaeniorhynchus, China anopheles mosquito (A nopheles Sinensis), Daikon Bae (Hylemya Brassicae), Dais Sayata Mabae (ASPHONDYLIA SP.), Delia Platura (Delia PLATURA),
• Hymenoptera pests such as Pristomyrmex ponnes, Antidae, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Dryocosmus kuriphilus, Formica fusca japonica , Wasps, Athalia infumata infumata, Arge pagana, Athalia japonica, Acromyrmex spp., Fire ants (Solenopsis spp.), Arge mali (Ochetellusglaber) and the like.
• Orthoptera Grasshopper order pests such as Homorocoryphus lineosus, Gryllotalpa sp., Oxya hyla intricata, Oxya yezoensis, Locusta migratoria, Oxya japonica (Homorocoryphus jezoensis), and Emma cricket (Teleogryllus emma).
• Thrips pests include Selenothrips rubrocinctus, Stenchaetothrips biformis, Haplothrips aculeatus, Ponticulothrips diospyrosi, Thrips flavus, Thrips flavus ( Anaphothrips obscurus) , Liothrips floridensis, Gladiolus simplex, Thrips nigropilosus, Heliothrips haemorrhoidalis, Pseudodendrothrips mori, Microcephalothrips abdominalis Long-tailed thrips ( Leeuwenia pasanii), Litotetothrips pasaniae, Scirtothrips citri, Haplothrips chinensis, Mycterothrips glycines, Thrips setosus, Scirtoth rips dorsalis ), Dendrothrips minowai, Haplothrips niger, Thrips tabaci, Thrip
• Examples of acarid pests include Leptotrombidium akamushi, Tetranychus ludeni, Dermacentor variabilis, Tetranychus truncatus, Ornithonyssus bacoti, Demodex canis, and Ticks such as Tetranychus viennensis, Tetranychus kanzawai, Rhipicephalus sanguineus, Cheyletus malaccensis, Tyrophagus putrescentiae, Dermatophagoides farinae, Redback spider (Latrodectus hasseltii), Latrodectus Dermacentor taiwanicus, Acaphylla theavagrans, Polyphagotarsonemus latus, Aculops lycopersici, Ornithonyssus sylvairum, Tetranychus urticae, Eriophyes chibaensis , Sarcoptes scabiei, Haemaphysalis long
• termite pests include Reticulitermes miyatakei, Incisitermes minor, Coptotermes forsanus, Hodotermopsis japonica, Reticulitermes sp., Reticulitermes flaviceps amamianus , Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus, Taiwan termites (O dontotermes forosanus) , Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes speratus.
• Cockroach pests such as Periplaneta fuliginosa, Blattella germanica, Blatta orientalis, Periplaneta brunnea, Blattella lituricollis, Periplaneta japonica, and Periplaneta japonica (Periplaneta americana) and the like.
• Flea order examples include the human flea (Pulex irritans), the cat flea (Ctenocephalides felis), and the chicken flea (Ceratophyllus gallinae).
• Nematodes include Nothotylenchus acris, Aphelenchoides besseyi, Pratylenchus penetrans, Meloidogyne hapla, Meloidogyne incognita, Globodera rostochiensis), Java root nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), Minaminegusare nematode (Pratylenchus coffeae), wheat negus nematode (Pratylenchus neglectus), and orange nematode (Tylenchus semipenetrans) and the like.
• molluscs examples include Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Lehmannina valentiana, Limax flavus, and Acusta despecta sieboldiana. is mentioned.
• the agricultural and horticultural insecticide of the present invention also has a strong insecticidal effect against another pest, Tuta absoluta.
• animal parasitic ticks that are one of the objects to be controlled include Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, and Haemaphysalis campanulata.
• fleas to be controlled include, for example, ectoparasitic wingless insects belonging to the order Siphonaptera, more specifically fleas belonging to the family Pulicidae and Ceratephyllus.
• fleas belonging to the family Ctenophylidae include dog flea (Ctenocephalides canis), cat flea (Ctenocephalides felis), human flea (Pulex irritans), chicken lift flea (Echidnophaga gallinacea), cheops rat flea (Xenopsylla cheopis), mole flea ( Leptopsylla segnis), European rat flea (Nosopsyllus fasciatus), and black rat flea (Monopsyllus anisus).
• Still other ectoparasites to be controlled include, for example, bovine lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), cow lice (Linognathus vituli), pig lice (Haematopinus suis), pubic lice (Phthirus pubis), and head lice (Pediculus capitis), and lice such as dog lice (Trichodectes canis), bullflies (Tabanus trigonus), culicoides schultzei (Culicoides schultzei), and blood sucking diptera (Simulium ornatum) pests, etc.
• nematodes such as lungworms, trichophylls, nodular worms, gastric parasites, roundworms, and heartworms
• Tapeworms such as tapeworms, tapeworms, tapeworms, tapeworms, and tapeworms
• flukes such as Schistosoma japonicum, and liver flukes, as well as coccidia, malaria parasites, intestinal sarcosporidia, toxoplasma , and protozoa such as Cryptosporidium.
• the agricultural and horticultural insecticide containing the compound represented by the general formula (1) of the present invention or a salt thereof as an active ingredient is an insect pest that damages paddy field crops, field crops, fruit trees, vegetables, other crops and flowers. Since it has a remarkable control effect against pests, it can be applied to nursery facilities, paddy fields, fields, fruit trees, vegetables, other crops, The intended effect of the agricultural and horticultural insecticide of the present invention can be obtained by treating seeds such as flowering plants, paddy water, stems and leaves, soil and other cultivation carriers.
• the compound of the present invention is absorbed from the roots, with or without the soil, by treating it with seedling soil for crops, flowers, etc., planting hole soil at the time of transplanting, stock base, irrigation water, cultivation water in hydroponics, etc.
• a preferred form of use is application utilizing the so-called systemic migration property by allowing the composition to evaporate.
• Useful plants to which the agricultural and horticultural insecticide of the present invention can be applied are not particularly limited. red beans, broad beans, peas, kidney beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables (cabbage, Tomatoes, spinach, broccoli, lettuce, onions, green onions, bell peppers, eggplants, strawberries, peppers, okra, chives, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, Japanese radish, turnips, lotus roots, burdock roots) , garlic, shallots, etc.), processed crops (cotton, hemp, beets, hops, sugarcane, sugar beet, olives, rubber, coffee, tobacco, tea, etc.), gourds (pumpkin, cucumber, watermelon, makuwa melon, melon, etc.) ), pasture grasse
• plants include HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, and sethoxydim. Also included are plants that have been given tolerance to herbicides such as acetyl-CoA carboxylase inhibitors, bromoxynil, dicamba, and 2,4-D by classical breeding methods or genetic recombination techniques.
• HPPD inhibitors such as isoxaflutole
• ALS inhibitors such as imazethapyr and thifensulfuron-methyl
• EPSP synthase inhibitors such as glyphosate
• glutamine synthase inhibitors such as glufosinate
• sethoxydim plants that have been given tolerance to herbicides such as acetyl-CoA carboxylase inhibitors, bromoxynil, dicamba
• plants that have been made tolerant by classical breeding methods are rape, wheat, sunflower and rice that are tolerant to imidazolinone ALS-inhibiting herbicides such as imazethapyr, under the trade name of Clearfield®. is already on sale.
• soybeans that are tolerant to sulfonylurea-based ALS-inhibiting herbicides such as thifensulfuron-methyl by classical breeding methods and are already on the market under the trade name of STS soybeans.
• SR corn and the like are examples of plants that have been made tolerant to acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides by classical breeding methods.
• acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides by classical breeding methods.
• plants endowed with resistance to acetyl-CoA carboxylase inhibitors are listed in the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA) Vol. 87, pp. 7175-7179 (1990).
• Mutant acetyl-CoA carboxylase resistant to acetyl-CoA carboxylase inhibitors has been reported in Weed Science, Vol. 53, pp. 728-746 (2005).
• a plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing a plant acetyl-CoA carboxylase-related mutation into a plant acetyl-CoA carboxylase. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318. By introducing substitution mutations, plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, etc. can be produced, and the agricultural and horticultural insecticide of the present invention can also be used for these plants. .
• toxins expressed in transgenic plants insecticidal proteins derived from Bacillus cereus and Bacillus popiliae; insecticidal proteins such as endotoxin, VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIPs) such as ricin, maize-RIP, abrin, rufin, saporin, bryozin; Steroid metabolizing enzymes such as hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitors; HMG-CoA reduc
• Toxins expressed in such transgenic plants include ⁇ -endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab, VIP1, VIP2, VIP3 or VIP3A. Also included are insecticidal protein hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are created using recombinant techniques by new combinations of different domains of these proteins. As a partially deleted toxin, Cry1Ab with partially deleted amino acid sequence is known. A modified toxin has one or more of the amino acids of the native toxin substituted.
• the toxins contained in these recombinant plants especially confer resistance to Coleoptera pests, Hemiptera pests, Diptera pests, Lepidoptera pests, and nematodes.
• the agricultural and horticultural insecticide of the present invention can be used in combination with those techniques or systematized.
• the agricultural and horticultural insecticide of the present invention is used as it is, or in the form of being diluted with water or the like as appropriate, or in the form of being suspended, in an amount effective for controlling pests or nematodes.
• pests and nematodes that occur in fruit trees, grains, vegetables, etc.
• seed immersion in chemicals, seed dressing, culper treatment Seed treatment, soil all layer mixing, row application, bed soil mixing, cell seedling treatment, planting hole treatment, stock base treatment, top dressing, rice box treatment, water surface application, etc. It can also be used after being absorbed.
• the agricultural and horticultural insecticide of the present invention may be used as it is, or in a form in which it is diluted or suspended with water or the like and used in an effective amount for controlling pests in a place where the occurrence of the pests is expected.
• it in addition to spraying on grain storage pests, house pests, sanitary pests, forest pests, etc., it can also be used for application to building materials, smoke, bait, and the like.
• Seed treatment methods include, for example, a method of immersing seeds in a liquid or undiluted liquid state to allow the drug to permeate, a method of mixing solid or liquid preparations with seeds, and a method of dressing. Examples include a method of treating and adhering to the surface of seeds, a method of coating seeds by mixing with an adhesive carrier such as resin or polymer, and a method of spraying near seeds at the same time as planting.
• the "seed" to be subjected to the seed treatment means a plant body in the early stage of cultivation used for plant propagation. Mention may be made of plants for vegetative propagation.
• the "soil” or “cultivation carrier” for plants when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that allows plants to grow may be used, such as so-called soil, seedling mats, water, etc. Specific materials include sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, high It may be a molecular substance, rock wool, glass wool, wood chips, bark, or the like.
• liquid formulations such as emulsion concentrates and flowable formulations, or solid formulations such as wettable powders or wettable granules, should be diluted with water as appropriate.
• a method of spraying a method of spraying dust, or smoking.
• a method of applying to soil for example, a method of applying a liquid formulation to the stock of a plant or a seedling nursery without diluting it with water, or a method of applying granules to the stock of a plant or a seedling for raising Method of spraying on seedbeds, etc., method of spraying powders, wettable powders, wettable granules, granules, etc. before sowing or transplanting and mixing them with the entire soil, before sowing or before planting plants, Examples thereof include a method of spraying powders, wettable powders, wettable granules, granules, etc. on the strips.
• the dosage form may differ depending on the application period, such as application at the time of sowing, application at the time of greening, and application at the time of transplanting. It should be applied in a mold. It can also be applied by mixing with potting soil, and mixing potting soil with powders, wettable granules, granules, etc., for example, mixing with bed soil, mixing with covering soil, mixing with the whole potting soil, etc. Can be done. Simply alternating layers of potting soil and various formulations may be applied.
• solid formulations such as jumbo formulations, pack formulations, granules and wettable granules, and liquid formulations such as flowables and emulsions are usually sprayed over flooded paddy fields.
• an appropriate formulation can be sprayed or injected into the soil as it is or mixed with fertilizer.
• chemical solutions such as emulsions and flowables at water inlets, irrigation systems, and other water inflow sources into paddy fields, it is possible to apply the chemicals in a labor-saving manner along with the supply of water.
• the treatment can be applied to seeds or cultivation carriers close to plants during the period from seeding to seedling raising.
• the agent for plants that are directly sown in a field, it is preferable to apply the agent directly to the seeds as well as to the base of the plant under cultivation.
• Spray treatment using granules, or irrigation treatment in the form of a liquid diluted or undiluted drug can be performed. It is also a preferred treatment to mix the granules with the cultivation carrier before sowing and then sowing.
• the irrigation treatment of liquid chemicals or the spraying treatment of granules to the nursery bed for raising seedlings is preferable.
• the agricultural and horticultural insecticide of the present invention is generally used after being formulated into a form convenient for use according to a conventional method for agricultural chemical formulations. That is, the compound represented by the general formula (1) of the present invention or a salt thereof is mixed with a suitable inert carrier or, if necessary, an adjuvant in an appropriate proportion, dissolved, separated, suspended.
• Turbidity, mixing, impregnation, adsorption or adhesion may be used by formulating into appropriate dosage forms such as suspensions, emulsions, liquids, wettable powders, wettable granules, granules, powders, tablets, packs, etc. Good luck.
• composition of the present invention can contain, in addition to the active ingredient, additive components commonly used in agricultural chemical formulations or animal parasite control agents, if necessary.
• additive components include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreaders, spreading agents, antifreeze agents, , anti-caking agents, disintegrants, anti-degradants and the like.
• antiseptics, plant pieces, etc. may be used as additive components. These additive components may be used alone or in combination of two or more.
• solid carriers examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. , synthetic silicic acid, synthetic silicates, starch, cellulose, organic solid carriers such as plant powders (e.g.
• plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea
• examples include inorganic hollow bodies, plastic hollow bodies, fumed silica (white carbon), and the like. These may be used alone or in combination of two or more.
• liquid carriers examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerin.
• polyhydric alcohol compounds such as propylene glycol ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, ketones such as cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, THF, etc.
• ethers normal paraffin, naphthene, isoparaffin, kerosene, mineral oil and other aliphatic hydrocarbons, benzene, toluene, xylene, solvent naphtha, alkylnaphthalene and other aromatic hydrocarbons, dichloromethane, chloroform, carbon tetrachloride, etc.
• Halogenated hydrocarbons esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate, lactones such as ⁇ -butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, and N-alkylpyrrolidinone nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water. These may be used alone or in combination of two or more.
• Surfactants used as dispersants and wetting agents include, for example, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol,
• binders and tackifiers include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and average molecular weights of 6,000 to 20,000.
• cephalin, lecithin, etc. cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, crosslinked polyvinylpyrrolidone, copolymer of maleic acid and styrenes coalescence, (meth)acrylic acid-based copolymer, half ester of polyhydric alcohol polymer and dicarboxylic acid anhydride, water-soluble salt of polystyrene sulfonic acid, paraffin, terpene, polyamide resin, polyacrylate, polyoxy Ethylene, wax, polyvinyl alkyl ether, alkylphenol-formalin condensate, synthetic resin emulsion and the like.
• thickening agents examples include xanthan gum, guar gum, daiyutan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compounds, water-soluble polymers such as polysaccharides, high-purity bentonite, fumed silica (fumed Inorganic fine powders such as silica, white carbon) and the like are included.
• coloring agents include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.
• Antifreeze agents include, for example, polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
• Auxiliaries for caking prevention and disintegration promotion include, for example, starch, polysaccharides such as alginic acid, mannose and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, copolymer of methacrylic acid ester, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene/isobutylene/maleic anhydride copolymer, starch/polyacrylonitrile graft copolymer A polymer etc. are mentioned.
• antidegradants examples include drying agents such as zeolite, quicklime and magnesium oxide, antioxidants such as phenol compounds, amine compounds, sulfur compounds and phosphoric compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. be done.
• Preservatives include, for example, potassium sorbate, 1,2-benzothiazolin-3-one and the like. Furthermore, if necessary, other aids such as functional spreaders, activity enhancers such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers. agents can also be used.
• the blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight per 100 parts by weight of the agricultural and horticultural insecticide of the present invention. , 0.01 to 50 parts by weight (0.01 to 50% by weight with respect to the total weight of the agricultural and horticultural insecticide) is suitable for powders, granules, emulsions or wettable powders.
• the amount of the agricultural and horticultural insecticide of the present invention to be used depends on various factors such as purpose, target pests, growth conditions of crops, tendency of occurrence of pests, weather, environmental conditions, dosage form, method of application, place of application, time of application, and the like. Although it varies, it may be appropriately selected according to the purpose from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, per 10 ares of the active ingredient compound.
• the agricultural and horticultural insecticide of the present invention can be used with other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, fungicides, and other agricultural and horticultural insecticides for the purpose of expanding the pests to be controlled, the appropriate period for control, or reducing the amount of the drug. It can be used by mixing with biopesticides and the like, and it is also possible to use by mixing with herbicides, plant growth regulators, fertilizers and the like depending on the situation of use.
• Agricultural and horticultural fungicides used for similar purposes e.g., aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar-S-methyl ), azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isotianil (isotianil), isovaledione, isopyrazam, isofetamid, isofrucypram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin ), iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-albesilate, iminoctadine-triacetate ), imibenconazole, inpyrfluxam, unicon
• herbicides e.g. 4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, asulam, acetochlor, Atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole, amino cyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor, alloxydim ( alloxydim), alorac, iofensulfuron, isouron, isocarbamid, isox
• NPV nuclear polyhedrosis virus
• GV granulosis virus
• CPV cytoplasmic polyhedrosis virus
• EPV entomopoxi virus
• insecticides or nematicides such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans, etc.
• Microbial pesticides used as agents as fungicides such as Trichoderma lignorum, Agrobacterium radiobacter, non-pathogenic Erwinia carotovora, Bacillus subtilis
• fungicides such as Trichoderma lignorum, Agrobacterium radiobacter, non-pathogenic Erwinia carotovora, Bacillus subtilis
• a similar effect can be expected by mixing with a microbial pesticide used, a biopesticide used as a herbicide such as Xanthomonas campestris, and the like.
• biological pesticides such as Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isea, Dacnusa sibirica, Phytoseiulus persimilis), Amblyseius cucumeris, natural enemy organisms such as Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl acetate, (E, Z )-4,10-tetradecadinyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-icosen-10-one, 14-methyl-1 - Can be used in combination with pheromones such as octadecene.
• pheromones such as octadecene.
• N-(4-fluorophenyl)-5-hydroxy-3-oxo-1-(6-(trifluoromethyl)pyridin-3-yl)-1,2,3,6-tetrahydropyridazine-4-carboxamide (0 .50 g, 1.3 mmol) in chloroform (8.8 mL) was added with ethyl isocyanate (0.11 mL, 1.4 mmol) and N,N-diisopropylethylamine (0.26 mL, 1.5 mmol) in that order. Stirred for an hour. Hydrochloric acid was added to the reaction solution, and the mixture was extracted with ethyl acetate three times.
• N-(4-fluorophenyl)-5-hydroxy-3-oxo-1-(6-(trifluoromethyl)pyridin-3-yl)-1,2,3,6-tetrahydropyridazine-4-carboxamide (0 .20 g, 0.50 mmol) in tetrahydrofuran (2.5 mL) was added with 1,1′-thiocarbonyldiimidazole (98 mg, 0.55 mmol) and stirred at room temperature for 1 hour. Subsequently, methylamine (40% methanol solution, 61 ⁇ L, 0.6 mmol) was added and stirred at room temperature for 6 hours.
• Toluene (5 .5 mL) solution was added with 4-fluoroaniline (0.19 mL, 1.9 mmol) and heated under reflux for 2 hours. After allowing to cool to room temperature, 1N aqueous sodium hydroxide solution was added, and the mixture was washed with ethyl acetate. 1N Hydrochloric acid was added under ice-cooling, and the mixture was extracted with ethyl acetate.
• 5-Amino-2-trifluoromethylpyridine (30.0 g, 185 mmol) was dissolved in concentrated hydrochloric acid (185 mL), and an aqueous solution (92.5 mL) of sodium nitrite (14.0 g, 204 mmol) was added under ice cooling. It was slowly added dropwise over 30 minutes while controlling the internal temperature not to exceed 10°C. After completion of dropping, the mixture was stirred at the same temperature for 1 hour to prepare a diazonium salt solution.
• tin (II) chloride 73.7 g, 389 mmol was dissolved in concentrated hydrochloric acid (92.5 mL), and the prepared diazonium salt solution was added thereto under ice-cooling to an internal temperature of 10°C. It was slowly dripped over 30 minutes while adjusting so as not to exceed it. After completion of dropping, the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, an aqueous solution (300 mL) of sodium hydroxide (160 g, 4.00 mol) was added while stirring under ice-cooling to neutralize the reaction solution, ethyl acetate (500 mL) was added, and the mixture was filtered through celite.
• Formulation example 1 The compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above are uniformly mixed and dissolved to form an emulsion.
• Formulation example 2 The compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to obtain powders.
• Formulation example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts Calcium lignosulfonate 5 parts The above are uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to form granules.
• Formulation example 4 The compound of the present invention 20 parts kaolin and synthetic highly dispersed silicic acid 75 parts A mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above are uniformly mixed and pulverized to obtain a wettable powder.
• Test example 1 Insecticidal test against diamondback moth (Plutella xylostella) Adults of diamondback moth were released to Chinese cabbage seedlings to lay eggs. It was immersed for about 30 seconds in a chemical solution diluted to 50 ppm or 500 ppm with a drug as an active ingredient, air-dried, and then left in a constant temperature room at 25°C. After 6 days of immersion in the chemical solution, the number of surviving insects was investigated, the corrected dead insect rate was calculated by the following formula, and judgment was made according to the following criteria. 1 ward 10 horses 3 consecutive system.
• Test example 2 Insecticidal test against Laodelphax striatellus
• the compound represented by the general formula (1) of the present invention or a salt thereof is dispersed in water and diluted into a chemical solution of 50 ppm or 500 ppm, and rice seedlings (variety: Nipponbare) are added to the chemical solution. Immersed for 30 seconds, air-dried, placed in a glass test tube, inoculated with 10 each of the 3rd instar green leafhopper planthopper, and then plugged with cotton. It was calculated and judged according to the judgment criteria of Test Example 1.
• Test example 3 Insecticidal test against Frankliniella occidentalis
• Leaf discs of kidney bean were inoculated with female adult thrips occidentalis occidentalis Occidentalis occidentalis Occidentalis occidentalis occidentalis thrips occidentalis spp.
• a chemical solution containing the compound shown in Tables 1 to 6 as an active ingredient diluted to 50 ppm or 500 ppm was sprayed.
• the number of surviving larvae of this species was investigated, and the corrected mortality rate was calculated according to the following formula. Double system.
• the compound of the present invention or its salt has excellent effects as an insecticide.

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