3-azabicyclohexane compound, agricultural and horticultural herbicide containing compound, and method for using same

Abstract

To create a new compound. 3-Azabicyclohexane compound represented by general formula (I) and a salt thereof, wherein R1, R2, R3, R4, R5, R6, and R7 each represent a hydrogen atom or the like; X represents an oxygen atom or the like; Y represents a CH2 group or the like; A represents a substituted phenyl group or the like; and Q represents a hydroxyl group or the like.

Description

3-Azabicyclohexane compound, agricultural and horticultural herbicide containing said compound, and method of using the same

[0001] The present invention relates to a 3-azabicyclohexane compound and a salt thereof, an agricultural and horticultural herbicide containing said compound or its salt as an active ingredient, and a method for using them.

[0002] Patent Documents 1 and 2 describe that certain pyrrolidine compounds have herbicidal activity. Patent Document 3 describes that certain pyrrolidine compounds have a plant growth promoting effect. However, these documents do not suggest or disclose anything about the 3-azabicyclohexane compounds of the present invention.

[0003] International Publication No. 2022 / 200208 Pamphlet International Publication No. 2024 / 081762 Pamphlet International Publication No. 2022 / 268520 Pamphlet

[0004] A stable supply of food is essential to alleviate the food crisis that is expected to accompany the expected increase in world population in the near future. A stable food supply requires economical and efficient methods of killing or controlling weeds that interfere with crop cultivation and harvesting, and one solution to this problem is the development of novel herbicides and plant growth regulators. The present invention addresses this social need by providing novel herbicides that are highly safe for crops and have excellent herbicidal activity against weeds.

[0005] The present inventors have conducted extensive research to develop novel agricultural and horticultural herbicides, and as a result have found that the 3-azabicyclohexane compounds represented by general formula (I) of the present invention and salts thereof are useful as agricultural and horticultural herbicides, thereby completing the present invention.

[0006] That is, the present invention provides a compound according to the present invention, which comprises: [1] a compound of general formula (I): [In the formula, R １ is (a1) a hydrogen atom; or (a2) (C １ -C ６ ) alkyl group; R ２ and R ５ may be the same or different, and are (b1) a hydrogen atom; (b2) a halogen atom; or (b3) (C１ -C ６ ) alkyl group; R ３ and R ４ may be the same or different, and are (c1) a hydrogen atom; (c2) a halogen atom; or (c3) (C １ -C ６ ) alkyl group; R ６ and R ７ may be the same or different, (d1) a hydrogen atom; (d2) (C １ -C ６ ) alkyl group; (d3) (C ３ -C ６ ) cycloalkyl group; (d4) (C １ -C ６ ) haloalkyl group; or (d5) R ６ and R ７ may be bonded to each other to form a 3- to 6-membered aliphatic ring. X represents an oxygen atom or a sulfur atom, and Y represents CH, CH, CH, C(Me)H, or CHF.

[0007] A is (e1) (C ３ -C ６ ) cycloalkyl group; (e2) (C ３ -C ６ ) cycloalkyl (C １ -C ６ ) alkyl group; (e3) aryl group; (e4) may be the same or different and are selected from the group consisting of (a) halogen atom, (b) cyano group, (c) nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (e5) an aromatic heterocyclic group; (e6) which may be the same or different and which are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (e6) an aromatic heterocyclic group having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; (e7) a non-aromatic heterocyclic group; or (e8) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) a non-aromatic heterocyclic group having on the ring 1 to 3 substituents selected from alkylsulfonyl groups;

[0008] Q is (f1) a hydroxyl group; (f2) a (C1-C ６ ) alkoxy group; (f3) halo (C1-C ６) an alkoxy group; (f4) (C ２ -C6) alkenyloxy group; (f5) halo(C ２ -C ６ ) alkenyloxy group; (f6) (C2-C ６ ) alkynyloxy group; (f7) halo (C2-C ６ ) an alkynyloxy group; (f8) (C ３ -C ６ ) cycloalkyloxy group; (f9) halo (C ３ -C ６ ) cycloalkyloxy group; (f10) (C ３ -C ６ ) cycloalkyl(C-C ６ ) alkoxy group; (f11) halo (C ３ -C ６ ) cycloalkyl(C-C ６ ) alkoxy group; (f12) (C1-C ６ ) alkoxy(C1-C ６ ) alkyl group; (f13) (C1-C ６ ) alkoxycarbonyl (C-C ６ ) an alkoxy group; (f14) an aryloxy group; (f15) which may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f16) an aryloxy group having 1 to 5 substituents on the ring selected from aryl (C1-C ６ ) alkoxy group; (f17) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C６ ) aryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkoxy group; (f18) aryloxy (C1-C ６ ) alkoxy group; (f19) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryloxy (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups ６ ) alkoxy group; (f20) arylthio (C1-C ６ ) alkoxy group; (f21) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) arylthio (C1-C2) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkoxy group; (f22) aromatic heterocyclic oxy group; (f23) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f24) a non-aromatic heterocyclic oxy group; (f25) which may be the same or different and which are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f26) a non-aromatic heterocyclic oxy group having 1 to 3 substituents on the ring selected from an aromatic heterocyclic (C １ -C ６ ) alkoxy group; (f27) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６) an aromatic heterocycle (C) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; １ -C ６ ) alkoxy group; (f28) non-aromatic heterocycle (C １ -C ６ ) alkoxy group; (f29) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) a non-aromatic heterocyclic ring (C １ -C ６ ) alkoxy group; (f30) amino group; (f31) mono (C1-C ６ ) alkylamino group; (f32) di(C1-C ６) alkylamino groups (the alkyl groups may be the same or different); (f33) mono (C ２ -C ６ ) alkenylamino group; (f34) di(C ２ -C ６ ) alkenylamino group (the alkenyl groups may be the same or different); (f35) mono (C ２ -C ６ ) alkynylamino group; (f36) di(C ２ -C ６ ) alkynylamino group (the alkynyl groups may be the same or different); (f37) mono (C ３ -C ６ ) cycloalkylamino group; (f38) mono(C ３ -C ６ ) cycloalkyl(C-C ６ ) alkylamino group; (f39) N—(C1-C ６ ) alkyl-N-(C ２ -C ６ ) alkenylamino group; (f40) N—(C1-C ６ ) alkyl-N-(C ２ -C ６ ) alkynylamino group; (f41) N—(C1-C ６ ) alkyl-N-(C ３ -C ６ ) cycloalkylamino group; (f42) N—(C1-C ６ ) alkyl-N-(C ３ -C ６ ) cycloalkyl(C-C ６ ) alkylamino group; (f43) N,N-di(C1-C ６ ) alkyl (the alkyl groups may be the same or different). sulfamoylamino group; (f44) mono (C1-C ６ ) an alkylsulfonylamino group; (f45) a monoarylamino group; (f46) which may be the same or different, and which are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f47) a monoaryl (C1-C ６ ) alkylamino group; (f48) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) alkoxycarbonyl group, (j) (C １ -C ３) alkylenedioxy group, (k) halo (C １ -C3) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) monoaryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkylamino group; (f49) monoaromatic heterocyclic amino group; (f50) may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f51) a non-aromatic heterocyclic group; (f52) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) a non-aromatic heterocyclic group having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; {In the formula, R １０ (g1) a hydrogen atom; (g2) an amino group; (g3) a cyano group; (g4) (C１ -C ６ ) alkyl group; (g5) (C １ -C ６ ) alkylthio group; (g6) mono (C1-C ６ ) alkylamino group; or (g7) di(C1-C ６ ) alkylamino group (the alkyl groups may be the same or different); R １１ is (h1)(C １ -C ６ ) alkyl group; (h2) halo (C １ -C ６ ) alkyl group; (h3) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group; (h4) (C １ -C ６ ) alkoxycarbonyl group; (h5) (C １ -C ６ ) alkylthio (C １ -C ６ ) alkyl group; (h6) halo (C １ -C ６ ) alkylthio (C １ -C ６ ) alkyl group; (h7) (C １ -C ６ ) alkylsulfinyl (C １ -C ６ ) alkyl group; (h8) halo (C １ -C ６ ) alkyl(C １ -C ６ ) alkylsulfinyl group; (h9) (C １ -C ６ ) alkylsulfonyl (C １ -C ６ ) alkyl group; (h10) halo (C １ -C ６ ) alkylsulfonyl (C １ -C ６ ) alkyl group; (h11) aryl group; (h12) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (h13) an aromatic heterocyclic group; (h14) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl group, and (q) halo(C １ -C ６ ) an aromatic heterocyclic group having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; R １０ and R １１ (h14) can be bonded to form an aliphatic ring, or (h15) the aliphatic ring may be the same or different, and is (a) a halogen atom, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (i) (C １ -C ６ ) alkoxycarbonyl group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６) alkylsulfonyl groups, which may have one or more substituents selected from the group consisting of: {In the formula, R １２ and R １３ may be the same or different, (i1) a hydrogen atom; (i2) (C １ -C ６ ) alkyl group; (i3) halo (C １ -C ６ ) alkyl group; (i4) (C1-C ６ ) cycloalkyl group; (i5) aryl (C1-C ６ ) alkyl groups; (i6) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C3) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６) alkylsulfonyl group, and aryl (C1-C ６ ) alkyl group; or (i7) R １２ and R １３ may be bonded to each other to form a 3- to 6-membered aliphatic ring; １４ is (C １ -C ６ ) represents an alkyl group.} represents a group represented by the formula: • is bonded to C of the C═X group. ] and salts thereof.

[0009] [2] R １ is (a1) a hydrogen atom; or (a2) (C １ -C ６ ) alkyl group; R ２ and R ５が , which may be the same or different, (b1) a hydrogen atom; or (b3) (C １ -C ６ ) alkyl group; R ３ and R ４ may be the same or different, (c1) a hydrogen atom; or (c3) (C １ -C ６ ) alkyl group; R ６ and R ７ (d1) represents a hydrogen atom; X represents an oxygen atom; and Y represents CH ２ , C.H. ２ CH ２ , C(Me)H, or CHF;

[0010] A is (e1) (C ３ -C ６ ) cycloalkyl groups; (e4) may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (e6) an aryl group having 1 to 5 substituents on the ring selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (e6) an aromatic heterocyclic group having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; or (e7) a non-aromatic heterocyclic group;

[0011] Q is (f1) a hydroxyl group; (f2) (C1-C ６ ) alkoxy group; (f8) (C ３ -C ６ ) cycloalkyloxy group; (f12) (C1-C ６ ) alkoxy(C1-C ６ ) alkyl group; (f13) (C1-C ６ ) alkoxycarbonyl (C-C ６ ) an alkoxy group; (f15) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f17) an aryloxy group having 1 to 5 substituents on the ring selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６) alkoxy group; (f19) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryloxy (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups ６ ) alkoxy group; (f21) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) arylthio (C1-C2) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkoxy group; (f23) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) ( C １ -C ６ ) alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo(C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f27) an aromatic heterocyclic oxy group having on the ring 1 to 3 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo(C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) alkylsulfonyl group, １ -C ６ ) alkoxy group; (f29) may be the same or different, and are: (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) alkylsulfonyl group, and a non-aromatic heterocyclic ring (C １ -C ６ ) alkoxy group; (f30) amino group; (f31) mono (C1-C ６ ) alkylamino group; (f37) mono(C ３ -C ６) cycloalkylamino group; (f43) N,N-di(C1-C ６ ) alkyl (dialkyl groups may be the same or different). sulfamoylamino group; (f44) mono (C1-C ６ ) alkylsulfonylamino group; (f46) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f50) a monoarylamino group having on the ring 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f51) a non-aromatic heterocyclic group; (f52) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １-C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ a non-aromatic heterocyclic group having on the ring 1 to 5 substituents selected from: a ) alkylsulfonyl group; a group represented by general formula (II); or a group represented by general formula (III), １０ (g1) a hydrogen atom; (g2) an amino group; or (g4) (C １ -C ６ ) alkyl group; R １１ (h11) represents an aryl group; and R １２ and R １３ may be the same or different, (i1) a hydrogen atom; (i2) (C １ -C ６ ) alkyl group; (i3) halo (C １ -C ６ ) alkyl group; (i4) (C1-C ６ ) cycloalkyl group; (i5) aryl (C1-C ６ ) alkyl group; (i6) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C3) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) alkylsulfonyl group, and aryl (C1-C ６ ) alkyl group; or (i7) R １２ and R １３ may be bonded to each other to form a 3- to 6-membered aliphatic ring; １４ However, (C １ -C ６ 3-azabicyclohexane compounds and salts thereof according to [1], wherein the alkyl group is a 3-azabicyclohexane compound.

[0012] [3] R １ represents (a1) a hydrogen atom; and R ２ and R ５ represents (b1) a hydrogen atom; and R ３ and R ４ (c1) represents a hydrogen atom; and R ６ and R ７ (d1) represents a hydrogen atom; X represents an oxygen atom; and Y represents CH2;

[0013] A is (e1) (C ３ -C ６) cycloalkyl groups; (e4) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ or (e6) an aryl group having 1 to 5 substituents on the ring selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) an alkylsulfonyl group;

[0014] Q is (f1) a hydroxyl group; (f2) (C1-C ６ ) alkoxy group; (f8) (C ３ -C ６ ) cycloalkyloxy group; (f12) (C1-C ６ ) alkoxy(C1-C ６ ) alkyl group; (f13) (C1-C ６ ) alkoxycarbonyl (C-C ６ ) an alkoxy group; (f15) may be the same or different, and are: (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C１ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f17) an aryloxy group having on the ring 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) alkylsulfonyl group, and aryl (C1-C ６ ) alkoxy group; (f19) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) alkylsulfonyl group, and aryloxy (C1-C６ ) alkoxy group; (f23) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) ( C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f27) an aromatic heterocyclic oxy group having on the ring 1 to 3 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １-C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) alkylsulfonyl group, １ -C ６ ) alkoxy group; (f29) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) alkylsulfonyl group, and a non-aromatic heterocyclic ring (C １ -C ６ ) alkoxy group; (f31) mono(C1-C ６ ) alkylamino group; (f37) mono(C ３ -C ６ ) cycloalkylamino group; (f46) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) ( C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １-C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f50) a monoarylamino group having on the ring 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f51) a non-aromatic heterocyclic group; a group represented by general formula (II); or a group represented by general formula (III), wherein R １０ represents (g1) a hydrogen atom; or (g2) an amino group; and R１１ (h11) represents an aryl group; and R １２ and R １３ may be bonded to each other to form a 3- to 6-membered aliphatic ring; １４ However, (C １ -C ６ [4] an agricultural and horticultural herbicide comprising the compound or salt thereof according to any one of [1] to [3] as an active ingredient; [5] a method for using the agricultural and horticultural herbicide according to [4], which comprises applying an effective amount of the agricultural and horticultural herbicide according to [4] to weeds, soil, paddy field, field or cultivation carrier; and [6] a method for controlling weeds, which comprises applying an effective amount of the agricultural and horticultural herbicide according to [4] to weeds, soil, paddy field, field or cultivation carrier.

[0015] The 3-azabicyclohexane compound or its salt of the present invention has excellent effects as an agricultural and horticultural herbicide.

[0016] In the definition of the 3-azabicyclohexane compound represented by general formula (I) of the present invention, "halo" means a "halogen atom" and represents a chlorine atom, bromine atom, iodine atom, or fluorine atom.

[0017] "(C １ -C ６ The term "alkyl group" refers to a linear or branched alkyl group having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a normal pentyl group, an isopentyl group, a tertiary pentyl group, a neopentyl group, a 2,3-dimethylpropyl group, a 1-ethylpropyl group, a 1-methylbutyl group, a normal hexyl group, an isohexyl group, or a 1,1,2-trimethylpropyl group.

[0018] "(C ２ -C ６The term ") alkenyl group" refers to a linear or branched alkenyl group having 2 to 6 carbon atoms, such as a vinyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 2-methyl-2-propenyl group, a 1-methyl-2-propenyl group, a 2-methyl-1-propenyl group, a pentenyl group, or a 1-hexenyl group.

[0019] "(C ２ -C ６ The term "alkynyl group" refers to a straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms, such as an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 3-methyl-1-propynyl group, a 2-methyl-3-propynyl group, a pentynyl group, or a 1-hexynyl group.

[0020] "(C ３ -C ６ The term "cycloalkyl group" refers to a cyclic alkyl group having 3 to 6 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.

[0021] "(C １ -C ６ Examples of the "alkoxy group" include a linear or branched alkoxy group having 1 to 6 carbon atoms, such as a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal butoxy group, a secondary butoxy group, a tertiary butoxy group, a normal pentyloxy group, an isopentyloxy group, a tertiary pentyloxy group, a neopentyloxy group, a 2,3-dimethylpropyloxy group, a 1-ethylpropyloxy group, a 1-methylbutyloxy group, a normal hexyloxy group, an isohexyloxy group, and a 1,1,2-trimethylpropyloxy group.

[0022] "(C １ -C ６ Examples of the "alkylthio group" include a linear or branched alkylthio group having 1 to 6 carbon atoms, such as a methylthio group, an ethylthio group, a normal propylthio group, an isopropylthio group, a normal butylthio group, a secondary butylthio group, a tertiary butylthio group, a normal pentylthio group, a normal hexylthio group, and an isohexylthio group.

[0023] "(C １ -C ６ The ") alkylsulfinyl group" refers to a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a methylsulfinyl group, an ethylsulfinyl group, a normal propylsulfinyl group, an isopropylsulfinyl group, a normal butylsulfinyl group, a secondary butylsulfinyl group, a tertiary butylsulfinyl group, a normal pentylsulfinyl group, a normal hexylsulfinyl group, or an isohexylsulfinyl group.

[0024] "(C １ -C ６ Examples of the "alkylsulfonyl group" include linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, normal propylsulfonyl group, isopropylsulfonyl group, normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, normal hexylsulfonyl group, and isohexylsulfonyl group.

[0025] "(C ３ -C ６ The term "cycloalkoxy group" refers to a cyclic alkyl group having 3 to 6 carbon atoms, such as a cyclopropoxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group.

[0026] "(C １ -C ３ Examples of "halo(C) alkylenedioxy group" include a methylenedioxy group, an ethylenedioxy group, and a propylenedioxy group. １ -C ３ ) alkylenedioxy group" includes a difluoromethylenedioxy group, a tetrafluoroethylenedioxy group, and the like.

[0027] "(C １ -C ６The term "alkoxycarbonyl group" refers to, 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, a tertiary butoxycarbonyl group, a pentyloxycarbonyl group, or the like. １ -C ６ ) an alkoxycarbonyl group having 2 to 7 carbon atoms, such as an alkoxycarbonyl group having an alkoxy group.

[0028] "N,N-di (C １ -C ６ The term "a) alkyl (dialkyl groups may be the same or different) sulfamoylamino group" refers to an N,N-dialkylsulfamoylamino group having 1 to 6 carbon atoms, such as an N,N-dimethylsulfamoylamino group, an N-ethyl-N-methylsulfamoylamino group, an N,N-diethylsulfamoylamino group, or an N,N-dinormalpropylsulfamoylamino group.

[0029] The above "(C １ -C ６ ) alkyl group," "(C １ -C ６ ) alkoxy group," "(C １ -C ６ ) alkylthio group," "(C １ -C ６ ) alkylsulfinyl group”, or “(C １ -C ６ The "halo(C) alkylsulfonyl group" may be substituted with one or more halogen atoms at substitutable positions, and when there are two or more halogen atoms substituted, the halogen atoms may be the same or different. １ -C ６ ) alkyl group," "halo(C １ -C ６ ) alkoxy group," "halo(C １ -C ６ ) alkylthio group," "halo(C １ -C ６ ) alkylsulfinyl group," "halo(C １ -C ６Similarly, other substituents having "halo" may be substituted with one or more halogen atoms at substitutable positions, and when there are two or more halogen atoms substituted, the halogen atoms may be the same or different.

[0030] Also, “(C １ -C ６ )," "(C ２ -C ６ )," "(C ３ -C ６ Expressions such as "(C)" indicate the range of the number of carbon atoms of various substituents. Furthermore, the above definitions can also be applied to groups to which the above substituents are linked. For example, "(C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group" means that a straight or branched chain alkoxy group having 1 to 6 carbon atoms is bonded to a straight or branched chain alkyl group having 1 to 6 carbon atoms.

[0031] The term "aryl group" refers to an aromatic hydrocarbon group having 6 to 10 carbon atoms, such as a phenyl group, a 1-naphthyl group, or a 2-naphthyl group.

[0032] Examples of the "aromatic heterocyclic group" include aromatic heterocyclic groups such as furyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, and triazinyl.

[0033] Examples of the "non-aromatic heterocyclic group" include non-aromatic heterocyclic groups such as pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, hexamethyleneiminyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, oxazolinyl, thiazolinyl, imidazolinyl, dioxolyl, dioxolanyl, dihydrooxadiazolyl, pyranyl, tetrahydropyranyl, thiopyranyl, tetrahydrothiopyranyl, tetrahydrofuryl, dioxanyl, pyrazolidinyl, pyrazolinyl, and tetrahydropyrimidinyl.

[0034] Examples of salts of the 3-azabicyclohexane compound represented by general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, and paratoluenesulfonate; and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium.

[0035] The 3-azabicyclohexane compound represented by general formula (I) of the present invention and its salts may have one or more asymmetric centers in their structural formula, and may exist as two or more optical isomers and diastereomers. The present invention encompasses all of the optical isomers and mixtures containing them in any ratio. Furthermore, the 3-azabicyclohexane compound represented by general formula (I) of the present invention and its salts may exist as two geometric isomers derived from a carbon-carbon double bond and a carbon-nitrogen double bond in their structural formula, and the present invention encompasses all of the geometric isomers and mixtures containing them in any ratio.

[0036] In general formula (I), preferably, R １ (a1) a hydrogen atom; or (a2) (C １ -C ６ ) alkyl group; and R ２ and R ５ may be the same or different, and are (b1) a hydrogen atom; (b2) a halogen atom; or (b3) (C １ -C ６ ) alkyl group; and R ３ and R ４ may be the same or different, (c1) a hydrogen atom; (c2) a halogen atom; (c3) (C １ -C ６ ) alkyl group; and R ６ and R ７ may be the same or different, (d1) a hydrogen atom; (d2) (C １ -C ６ ) alkyl group; (d3) (C ３ -C ６) cycloalkyl group; (d4) (C １ -C ６ ) a haloalkyl group; or (d5) R ６ and R ７ may be bonded to each other to form a 3- to 6-membered aliphatic ring, X is an oxygen atom or a sulfur atom, and Y is CH ２ , C.H. ２ CH ２ , C(Me)H, or CHF;

[0037] A is (e1) (C ３－ C ６ ) cycloalkyl group; (e2) (C ３－ C ６ ) cycloalkyl (C １ -C ６ ) alkyl group; (e3) aryl group; (e4) may be the same or different and are selected from the group consisting of (a) halogen atom, (b) cyano group, (c) nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C１ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (e5) an aromatic heterocyclic group; (e6) which may be the same or different and which are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (e6) an aromatic heterocyclic group having on the ring 1 to 3 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ a non-aromatic heterocyclic group having 1 to 3 substituents on the ring selected from alkylsulfonyl groups;

[0038] Q is (f1) a hydroxyl group; (f2) (C1-C ６ ) alkoxy group; (f3) halo (C1-C ６ ) an alkoxy group; (f4) (C ２ -C ６ ) alkenyloxy group; (f5) halo (C ２ -C ６ ) alkenyloxy group; (f6) (C2-C ６ ) alkynyloxy group; (f7) halo (C2-C ６ ) an alkynyloxy group; (f8) (C ３ -C ６ ) cycloalkyloxy group; (f9) halo (C ３ -C ６) cycloalkyloxy group; (f10) (C ３ -C ６ ) cycloalkyl(C-C ６ ) alkoxy group; (f11) halo (C ３ -C ６ ) cycloalkyl(C-C ６ ) alkoxy group; (f12) (C1-C ６ ) alkoxy(C1-C ６ ) alkyl group; (f13) (C1-C ６ ) alkoxycarbonyl (C-C ６ ) an alkoxy group; (f14) an aryloxy group; (f15) which may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６(f16) an aryloxy group having 1 to 5 substituents on the ring selected from aryl (C1-C ６ ) alkoxy group; (f17) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkoxy group; (f18) aryloxy (C1-C ６ ) alkoxy group; (f19) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryloxy (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups ６ ) alkoxy group; (f20) arylthio (C1-C ６ ) alkoxy group; (f21) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C１ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) arylthio (C1-C2) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkoxy group; (f22) aromatic heterocyclic oxy group; (f23) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f24) a non-aromatic heterocyclic oxy group; (f25) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６(f26) a non-aromatic heterocyclic oxy group having 1 to 3 substituents on the ring selected from an aromatic heterocyclic (C １ -C ６ ) alkoxy group; (f27) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) an aromatic heterocycle (C) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; １ -C ６ ) alkoxy group; (f28) non-aromatic heterocycle (C １ -C ６ ) alkoxy group; (f29) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) a non-aromatic heterocyclic ring (C １ -C ６ ) alkoxy group; (f30) amino group; (f31) mono (C1-C ６ ) alkylamino group; (f32) di(C1-C ６ ) alkylamino groups (the alkyl groups may be the same or different); (f33) mono (C ２ -C ６ ) alkenylamino group; (f34) di(C ２ -C ６ ) alkenylamino group (the alkenyl groups may be the same or different); (f35) mono (C ２ -C ６ ) alkynylamino group; (f36) di(C ２-C ６ ) alkynylamino group (the alkynyl groups may be the same or different); (f37) mono (C ３ -C ６ ) cycloalkylamino group; (f38) mono(C ３ -C ６ ) cycloalkyl(C-C ６ ) alkylamino group; (f39) N—(C1-C ６ ) alkyl-N-(C ２ -C ６ ) alkenylamino group; (f40) N—(C1-C ６ ) alkyl-N-(C ２ -C ６ ) alkynylamino group; (f41) N—(C1-C ６ ) alkyl-N-(C ３ -C ６ ) cycloalkylamino group; (f42) N—(C1-C ６ ) alkyl-N-(C ３ -C ６ ) cycloalkyl(C-C ６ ) alkylamino group; (f43) N,N-di(C1-C ６ ) alkyl (dialkyl groups may be the same or different). sulfamoylamino group; (f44) mono (C1-C ６ ) an alkylsulfonylamino group; (f45) a monoarylamino group; (f46) which may be the same or different, and which are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f47) a monoaryl (C1-C ６ ) alkylamino group; (f48) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C3) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) monoaryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkylamino group; (f49) monoaromatic heterocyclic amino group; (f50) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６(f51) a non-aromatic heterocyclic group; (f52) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ a non-aromatic heterocyclic group having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; a group represented by general formula (II); or a group represented by general formula (III), wherein R １０ (g1) a hydrogen atom; (g2) an amino group; (g3) a cyano group; (g4) (C １ -C ６ ) alkyl group; (g5) (C １ -C ６ ) alkylthio group; (g6) mono (C1-C ６) alkylamino group; or (g7) di(C1-C ６ ) alkylamino groups (the alkyl groups may be the same or different); １１ is (h1) (C １ -C ６ ) alkyl group; (h2) halo (C １ -C ６ ) alkyl group; (h3) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group; (h4) (C １ -C ６ ) alkoxycarbonyl group; (h5) (C １ -C ６ ) alkylthio (C １ -C ６ ) alkyl group; (h6) halo (C １ -C ６ ) alkylthio (C １ -C ６ ) alkyl group; (h7) (C １ -C ６ ) alkylsulfinyl (C １ -C ６ ) alkyl group; (h8) halo (C １ -C ６ ) alkyl(C １ -C ６ ) alkylsulfinyl group; (h9) (C １ -C ６ ) alkylsulfonyl group (C １ -C ６ ) alkyl; (h10) halo (C １ -C ６ ) alkylsulfonyl (C １ -C ６ ) alkyl group; (h11) aryl group; (h12) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (h13) an aromatic heterocyclic group; (h14) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C１ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) an aromatic heterocyclic group having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; R １０ and R １１ (h14) can be bonded to form an aliphatic ring, or (h15) the aliphatic ring may be the same or different, and is selected from the group consisting of (a) a halogen atom, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (i) (C １ -C ６ ) alkoxycarbonyl group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) alkylsulfonyl groups, and R １２ and R １３ may be the same or different, (i1) a hydrogen atom; (i2) (C １ -C６ ) alkyl group; (i3) halo (C １ -C ６ ) alkyl group; (i4) (C1-C ６ ) cycloalkyl group; (i5) aryl (C1-C ６ ) alkyl group; (i6) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C3) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkyl group; or (i7) R １２ and R １３ may be bonded to each other to form a 3- to 6-membered aliphatic ring; and R １４ is (C １ -C ６) alkyl group.

[0039] The general formula (I) particularly preferably comprises R １ (a1) a hydrogen atom; or (a2) (C １ -C ６ ) alkyl group; and R ２ and R ５が , which may be the same or different, (b1) a hydrogen atom; or (b3) (C １－ C ６ ) alkyl group; and R ３ and R ４ may be the same or different, (c1) a hydrogen atom; or (c3) (C １ -C ６ ) alkyl group; and R ６ and R ７ (d1) a hydrogen atom; X is an oxygen atom, and Y is CH ２ , C.H. ２ CH ２ , C(Me)H, or CHF;

[0040] A is (e1) (C ３－ C ６ ) cycloalkyl groups; (e4) may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (e6) an aryl group having 1 to 5 substituents on the ring selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６(e6) an aromatic heterocyclic group having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; (e7) a non-aromatic heterocyclic group;

[0041] Q is (f1) a hydroxyl group; (f2) (C1-C ６ ) alkoxy group; (f8) (C ３ -C ６ ) cycloalkyloxy group; (f12) (C1-C ６ ) alkoxy(C1-C ６ ) alkyl group; (f13) (C1-C ６ ) alkoxycarbonyl (C-C ６ ) an alkoxy group; (f15) may be the same or different, and are: (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６(f17) an aryloxy group having 1 to 5 substituents on the ring selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkoxy group; (f19) may be the same or different, and are: (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １-C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryloxy (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups ６ ) alkoxy group; (f21) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) arylthio (C1-C2) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkoxy group; (f23) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) ( C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f27) an aromatic heterocyclic oxy group having on the ring 1 to 3 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) an aromatic heterocycle (C) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; １ -C ６ ) alkoxy group; (f29) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) a non-aromatic heterocyclic ring (C １ -C ６ ) alkoxy group; (f30) amino group; (f31) mono (C1-C ６ ) alkylamino group; (f37) mono(C ３ -C ６ ) cycloalkylamino group; (f43) N,N-di(C1-C ６ ) alkyl (dialkyl groups may be the same or different) sulfamoylamino group; (f44) mono (C1-C ６ ) alkylsulfonylamino group; (f46) may be the same or different, and are: (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo(C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f50) a monoarylamino group having on the ring 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f51) a non-aromatic heterocyclic group; (f52) which may be the same or different and which are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ a non-aromatic heterocyclic group having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; a group represented by general formula (II); or a group represented by general formula (III), wherein R １０ (g1) a hydrogen atom; (g2) an amino group; or (g4) (C １ -C ６ ) alkyl group; and R １１ is (h11) an aryl group; and R １２ and R １３ may be the same or different, (i1) a hydrogen atom; (i2) (C １ -C ６ ) alkyl group; (i3) halo (C １ -C ６ ) alkyl group; (i4) (C1-C ６ ) cycloalkyl group; (i5) aryl (C1-C ６ ) alkyl groups; (i6) may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C3) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkyl group; or (i7) R １２ and R １３ may be bonded to each other to form a 3- to 6-membered aliphatic ring; and R １４ However, (C １ -C ６ ) alkyl group.

[0042] The general formula (I) is more preferably R １ is (a1) a hydrogen atom; and R ２ and R ５ is (b1) a hydrogen atom; and R ３ and R ４ is (c1) a hydrogen atom; and R ６ and R ７ (d1) a hydrogen atom; X is an oxygen atom, and Y is CH ２ and A is (e1) (C ３－ C ６ ) cycloalkyl groups; (e4) may be the same or different, and are: (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (e6) an aryl group having 1 to 5 substituents on the ring selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６) alkylsulfinyl group, (o) halo(C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) an aromatic heterocyclic group having 1 to 3 substituents on the ring selected from alkylsulfonyl groups;

[0043] Q is (f1) a hydroxyl group; (f2) (C1-C ６ ) alkoxy group; (f8) (C ３ -C ６ ) cycloalkyloxy group; (f12) (C1-C ６ ) alkoxy(C1-C ６ ) alkyl group; (f13) (C1-C ６ ) alkoxycarbonyl (C-C ６ ) an alkoxy group; (f15) may be the same or different, and are: (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f17) an aryloxy group having 1 to 5 substituents on the ring selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６) alkoxy group; (f19) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryloxy (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups ６ ) alkoxy group; (f23) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C１ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f27) an aromatic heterocyclic oxy group having on the ring 1 to 3 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) an aromatic heterocycle (C) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; １ -C ６ ) alkoxy group; (f29) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １-C ６ ) a non-aromatic heterocyclic ring (C １ -C ６ ) alkoxy group; (f31) mono(C1-C ６ ) alkylamino group; (f37) mono(C ３ -C ６ ) cycloalkylamino group; (f46) may be the same or different, and are: (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo(C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f50) a monoarylamino group having on the ring 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C１ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f51) a non-aromatic heterocyclic group; a group represented by general formula (II); or a group represented by general formula (III), wherein R １０ is (g1) a hydrogen atom; or (g2) an amino group; and R １１ is (h11) an aryl group; or R １２ and R １３ may be bonded to each other to form a 3- to 6-membered aliphatic ring; and R １４ However, (C １ -C ６ ) alkyl group.

[0044] Representative methods for producing the 3-azabicyclohexane compound of the present invention represented by general formula (I) are shown below, but the present invention is not limited to these.

[0045] Manufacturing method 1. In the formula, R １ , R ２ , R 3 , R ４ , R ５ , R ６ , R ７ , A, Q, X and Y are as defined above, and Q ０ represents a substituent bonded to the C=X group, and R represents C １ ~C ３ represents an alkyl group.

[0046] The cyclopropane-1,2-dicarboxylic anhydride represented by general formula (2) used as a starting material is commercially available and easily available, or can be produced according to the method described in J.A.C.S. 1958, 80, 6568-6572, J.A.C.S. 1962, 84, 2246-2249, or CN115417767.

[0047] The compound represented by general formula (4) can be produced by first reacting the compound represented by general formula (2) with the compound represented by general formula (3) in an inert solvent to produce the amide-carboxylic acid compound shown in parentheses.

[0048] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include chain or cyclic ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; and halogenated aromatic hydrocarbon solvents such as fluorobenzene, chlorobenzene, dichlorobenzene, etc. These inert solvents can be used alone or in combination of two or more.

[0049] 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., but may be appropriately selected from the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, etc. Alternatively, after completion of the reaction, the inert solvent may be distilled off, and the product may be used in the next step without purification.

[0050] Next, the amide-carboxylic acid compound produced in the previous step is reacted with a dehydrating agent in the presence or absence of an inert solvent to produce an imide compound represented by general formula (4).

[0051] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; and halogenated aromatic hydrocarbon solvents such as fluorobenzene, chlorobenzene, and dichlorobenzene. These inert solvents can be used alone or in combination of two or more.

[0052] Examples of dehydrating agents that can be used in this reaction include acid anhydrides such as acetic anhydride and trifluoroacetic anhydride, and thionyl chloride. The amount of the dehydrating agent used is usually in the range of about 1.0 to 5 times the molar amount of the amide-carboxylic acid compound, but the dehydrating agent can also be used in a solvent amount, and in such cases, no solvent may be used.

[0053] The reaction temperature in this reaction may generally be in the range of about 0°C to the boiling point of the solvent or dehydrating agent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. After completion of the reaction, 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 purifying it by recrystallization, column chromatography, etc., as necessary.

[0054] A 4-hydroxy-3-azabicyclohexane compound represented by general formula (5), wherein R1 is a hydrogen atom, the imide compound represented by formula (4) can be produced by reacting it with a reducing agent in an inert solvent. The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction, and examples thereof include alcohols such as methanol and ethanol, ethers such as tetrahydrofuran and dioxane, and aromatic hydrocarbons such as benzene, toluene, and xylene. These inert solvents can be used alone or in combination of two or more.

[0055] Reducing agents that can be used in this reaction include, for example, metal hydride compounds such as sodium borohydride, lithium borohydride, and zinc borohydride. The amount of reducing agent used in this reaction can be appropriately selected from a range of about 0.25 to 10 times the molar amount of the imide compound represented by general formula (4). The reaction temperature can be selected from a range of about -20°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., but can be appropriately selected from a range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by conventional methods and purified, as needed, by recrystallization, distillation, column chromatography, etc., to produce the target product. Alternatively, after completion of this reaction, the target product can be subjected to the next reaction without isolation.

[0056] A 4-hydroxy-3-azabicyclohexane compound represented by general formula (5), R 1 When is an alkyl group, it can be produced by reacting the imide compound represented by the general formula (4) with an alkyl magnesium halide or an alkyl lithium reagent in an inert solvent.

[0057] Examples of alkylmagnesium halides that can be used in this reaction include so-called Grignard reagents such as methylmagnesium bromide and ethylmagnesium bromide. Examples of alkyllithium reagents include methyllithium and butyllithium. Any inert solvent can be used in this reaction as long as it does not significantly inhibit the progress of this reaction, and examples of such solvents include linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, and tetrahydrofuran.

[0058] The reaction temperature is generally low, preferably between -78°C and room temperature. The reaction time varies depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours. Since this reaction is an equimolar reaction, the reagents may be used in equimolar amounts, but it is also possible to use a slight excess of one of the reactants. After completion of the reaction, the target product can be isolated from the reaction system containing the product by conventional methods, and the target product can be produced by purifying it, if necessary, by recrystallization, column chromatography, or the like.

[0059] The 3-azabicyclohexanecarboxylic acid compound represented by general formula (I-1) can be synthesized by reacting a 4-hydroxy-3-azabicyclohexane compound represented by general formula (5) with ethyl diethylphosphonoacetate represented by general formula (6) in the presence of a base in an inert solvent, according to the method described in WO 2003 / 101450. The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. Examples of the inert solvent include ethers such as diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and dioxane, and aromatic hydrocarbons such as benzene, toluene, and xylene. These inert solvents can be used alone or in combination of two or more.

[0060] The amounts of ethyl diethylphosphonoacetate represented by general formula (6) and base used may be appropriately selected from a range of about 1 to 5 times the molar amount of the 4-hydroxy-3-azabicyclohexane compound represented by general formula (5). The reaction temperature may be selected from a range from about −20°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected from a range of several minutes to 48 hours. Subsequently, an aqueous solution of an inorganic base such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, or potassium bicarbonate is added to the reaction solution to carry out hydrolysis. After completion of the reaction, the target product is isolated from the reaction system containing the target product by conventional methods and purified, as necessary, by recrystallization, distillation, column chromatography, or the like, to produce an ester of a 3-azabicyclohexanecarboxylic acid compound. Alternatively, the corresponding ester can be synthesized without hydrolysis after reacting the 4-hydroxy-3-azabicyclohexane compound represented by general formula (5) with ethyl diethylphosphonoacetate represented by general formula (6).

[0061] The 3-azabicyclohexane compound represented by general formula (I) can be produced by reacting a 3-azabicyclohexanecarboxylic acid compound represented by general formula (I-1) with a compound represented by general formula (7) in an inert solvent, with a condensing agent and a base. Examples of the condensing agent used in this reaction include diethyl cyanophosphate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), chlorocarbonates, 2-chloro-1-methylpyridinium iodide, propylphosphonic anhydride solution, and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, and the amount used can be appropriately selected from the range of 1 to 1.5 times the molar amount of the carboxylic acid.

[0062] Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, and potassium hydrogencarbonate; acetates such as sodium acetate and potassium acetate; tertiary amines such as triethylamine, diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. The amount of the base used is usually in the range of 1 to 5 times the moles of the carboxylic acid represented by general formula (I-1).

[0063] The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc.; esters such as ethyl acetate, etc.; amides such as dimethylformamide, dimethylacetamide, etc.; ketones such as acetone, methyl ethyl ketone, etc. These inert solvents may be used alone or in combination of two or more.

[0064] Since this reaction is an equimolar reaction, the carboxylic acid and compound (7) may be used in equimolar amounts, although either reactant may be used in excess. The reaction temperature may range from room temperature to the boiling point of the inert solvent used, and the reaction time may vary depending on the reaction scale and reaction temperature, but may be within the range of several minutes to 48 hours. After completion of the reaction, 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 purifying it, if necessary, by recrystallization, column chromatography, or the like.

[0065] As another production method, the compound can be produced by reacting a 3-azabicyclohexanecarboxylic acid compound with thionyl chloride in the presence or absence of an inert solvent to derive the corresponding acid chloride compound, and then reacting the acid chloride compound with a compound represented by general formula (7) in the presence of an inert solvent and a base. The inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of the reaction, and examples of such inert solvents include hydrocarbons such as hexane and heptane, aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride, and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene. These inert solvents can be used alone or in combination of two or more.

[0066] Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used; however, any one of the reactants may be used in excess. The base used in this reaction may be an inorganic or organic base. Examples of inorganic bases include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, and carbonates such as sodium carbonate, potassium carbonate, and sodium bicarbonate. Examples of organic bases include triethylamine, pyridine, and DBU. The amount of base used is typically 1 to 5 times the molar amount of the carboxylic acid chloride. The reaction temperature can be from room temperature to the boiling point of the inert solvent used. The reaction time varies depending on the reaction scale and reaction temperature, but may be within a range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the product by conventional methods, and, if necessary, purified by recrystallization, column chromatography, or the like to produce the target product. Alternatively, the product can be used in the next step without purification.

[0067] Among the 3-azabicyclohexane compounds represented by general formula (I), the thiocarbonyl compound can be produced by reacting the compound represented by general formula (I) with a thiocarbonyl agent in an inert solvent. Examples of the thiocarbonyl agent that can be used in this reaction include phosphorus pentasulfide and Lawesson's reagent [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide].

[0068] The thiocarbonyl agent that can be used in this reaction can be used in the range of 0.5 to 5 equivalents relative to the 3-azabicyclohexane compound represented by general formula (I), but preferably 1 to 2 equivalents. The reaction can be carried out at temperatures from 0°C to the boiling point of the solvent, but preferably room temperature to 150°C. The inert solvent used in this reaction can be any solvent that does not significantly inhibit the progress of the reaction. Examples of inert solvents include hydrocarbons such as hexane and heptane, and aromatic hydrocarbons such as benzene, toluene, and xylene. These inert solvents can be used alone or in combination of two or more. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by conventional methods, and the target product can be produced by purification, if necessary, by recrystallization, column chromatography, or the like.

[0069] Representative examples of the 3-azabicyclohexane compound represented by general formula (I) of the present invention are shown below in Tables 1 to 8, but the present invention is not limited to these. In the tables, "Me" represents a methyl group, "Et" represents an ethyl group, "Pr" represents a propyl group, "Bu" represents a butyl group, "Pen" represents a pentyl group, "Hex" represents a hexyl group, "Ph" represents a phenyl group, "Bn" represents a benzyl group, "n-" represents normal, "i-" represents iso, "s-" represents secondary, and "c-" represents cyclo. Physical properties are melting point (°C), refractive index n Ｄ (Measurement temperature: °C) or １ H-NMR data is shown, １ H-NMR data is listed in Table 9.

[0070] Table 1

[0071] Table 2

[0072] Table 3

[0073] Table 4

[0074] Table 5

[0075] Table 6

[0076] Table 7

[0077] Table 8

[0078] Table 9

[0079] Agricultural and horticultural herbicides containing the 3-azabicyclohexane compound represented by general formula (I) of the present invention or a salt thereof as an active ingredient are excellent in environmental safety, such as physical properties suitable for various labor-saving application methods, systemic activity, and appropriate soil persistence. Furthermore, agricultural and horticultural herbicides containing the compound represented by general formula (I) of the present invention or a salt thereof as an active ingredient are excellent in safety for animals including humans.

[0080] Useful plants for which the 3-azabicyclohexane compound represented by general formula (I) of the present invention or a salt thereof can be used are not particularly limited, and examples thereof include cereals (rice, barley, wheat, rye, oats, corn, etc.), beans (soybeans, adzuki 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.), leafy vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, green onion (chives, scallions), bell peppers, eggplant, strawberries, peppers, okra, chives, etc.), and root vegetables (carrots, potatoes, sweet potatoes, taro, daikon radish, turnips, lotus roots, etc.). , burdock, garlic, shallot, etc.), processing crops (cotton, hemp, beets, hops, sugarcane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), gourds (pumpkin, cucumber, watermelon, Sakhalin gourd, melon, etc.), pasture grasses (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turfgrass (Korean grass, bentgrass, etc.), ornamental crops for perfumes and the like (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees (ginkgo, cherry trees, Japanese maple, etc.), forest trees (abies fir, spruce, pines, cypress, cedar, cypress, eucalyptus, etc.), etc. In particular, it is highly adaptable to rice, barley, and wheat.

[0081] The above-mentioned "plant" also includes plants to which tolerance has been imparted by classical breeding methods or genetic engineering techniques to 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, acetyl-CoA carboxylase inhibitors such as sethoxydim, and herbicides such as bromoxynil, dicamba and 2,4-D.

[0082] Examples of "plants" that have been conferred resistance by classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr. Rice is already sold under the trade name Clearfield (registered trademark). Similarly, soybeans that have been conferred resistance to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron methyl by classical breeding methods are already sold under the trade name STS soybean. Similarly, examples of plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors such as trione oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods include SR corn.

[0083] Plants to which resistance to acetyl-CoA carboxylase inhibitors has been imparted are described in Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), Vol. 87, pp. 7175-7179 (1990), and elsewhere. Furthermore, mutant acetyl-CoA carboxylases resistant to acetyl-CoA carboxylase inhibitors have been reported in Weed Science, Vol. 53, pp. 728-746 (2005), and plants resistant to acetyl-CoA carboxylase inhibitors can be produced by introducing such mutant acetyl-CoA carboxylase genes into plants by genetic engineering techniques or by introducing a mutation related to conferring resistance into plant acetyl-CoA carboxylase. Furthermore, chimeraplasty techniques (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: By introducing a nucleic acid with a base substitution mutation, such as those represented by the general formula (I) of the present invention, into plant cells to introduce site-specific amino acid substitution mutations into the plant's acetyl-CoA carboxylase gene, ALS gene, or the like, it is possible to produce plants that are resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, or the like, and the compound represented by the general formula (I) of the present invention or a salt thereof can be used on these plants as well. The compound represented by the general formula (I) of the present invention does not harm these useful plants.

[0084] Further examples of toxins that can be expressed in genetically modified plants include insecticidal proteins from Bacillus cereus and Bacillus popiliae; δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C from Bacillus thuringiensis, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins or insect-specific neurotoxins; fungal toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors, patatin, cystatin, etc. ribosome-inactivating proteins (RIPs) such as ricin, corn-RIP, abrin, rufin, saporin, and bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; and glucanase.

[0085] Toxins expressed in such genetically modified plants also include hybrid toxins, truncated toxins, and modified toxins of δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, and insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A. Hybrid toxins are produced using recombinant technology by combining different domains of these proteins in new ways. A known example of a truncated toxin is Cry1Ab, which lacks a portion of its amino acid sequence. Modified toxins have one or more amino acids substituted in the native toxin. Examples of these toxins and recombinant plants capable of synthesizing these toxins are described in EP 0374753, WO 93 / 07278, WO 95 / 34656, EP 0427529, EP 0451878, WO 03 / 052073, etc.

[0086] The toxins contained in these recombinant plants confer resistance to Coleoptera, Hemiptera, Diptera, Lepidoptera, and nematodes, among others. The agricultural and horticultural herbicides of the present invention can be used in combination with or as a system with these technologies.

[0087] Weeds that can be controlled by the 3-azabicyclohexane compound represented by general formula (I) of the present invention or its salts include, as dicotyledonous weed genera, morning glory (Ipomoea), morning glory (Lindernia), American hornbeam (Sesbania), velvetleaf (Abutilon), chamomile (Matricaria), dog-eared mustard (Rorippa), nettle (Urtica), dead nettle (Lamium), cocklebur (Xanthium), mustard (Sinapis), ball-weed (Rotala), stag beetle (Veronica), poppy (Papaver), pigweed (Chenopodium), white clover (Trifolium), purslane (Portulaca), violet-leaf weed. Examples of suitable herbs include Viola, Pharbitis, Galeopsis, Datura, Solanum, Capsella, Cirsium, Sonchus, Galinsoga, Stellaria, Senecio, Amaranthus, Ambrosia, Kochia, Lamium, Leipidium, Polygonum, Galium, Centaurea, and Artemisia.

[0088] Monocotyledonous weed genera include Leptochloa, Phleum, Poa, Bolboschoenus, Festuca, Setaria, Eleusine, Sagittaria, Agropyron, Ischaemum, Cyperus, and Avena. , Bromus, Panicum, Cynodon, Monochoria, Alopecurus, Paspalum, Commelina, Fimbristylis, Lolium, Brachiaria, Agrostis, Eleocharis, Echinochloa esculenta, Scirpus, Schoenoplectus, Digitaria, Sorghum, and the like.

[0089] Specific examples of other weeds include Spirogyra, Amaranthus retroflexus, Amaranthus viridis, Setaria faberi, Leersia japonica, Leptochloa chinensis, Lindernia angustifolia, Lindernia procumbens, Dopatrium junceum, Ipomoea hederacea, Lindernia dubia, Sida spinosa, Polygonum pensylvanicum, Sesbania exaltata, Geranium carolinense, and Chenopodium ambrosioides, ragweed (Conyza bonariensis), foxtail (Setaria italica), burlap ragweed (Amaranthus powellii), knotweed (Polygonum cuspidatum), velvetleaf (Abutilon theophrasti), chamomile (Matricaria perforata), Japanese knotweed (Polygonum longisetum), persimmon (Veronica polita), barnyard grass (Echinochloa crus-galli), black-eyed jasmine (Amaranthus lividus), nightshade (Solanum nigrum), night burdock (Schoenoplectus juncoides (Roxb.) Palla), barnyard grass (Bromus catharticus), warbler (Murdannia keisak), and float clubweed (Bolboschoenus fluviatilis), Floating Crab (Scirpus maritimus), Bromus tectorum, Sagittaria pygmaea Miq, Rumex obtusifolius, Leersia oryzoides(L.) Sw.), green foxtail (Setaria viridis), sickleweed (Cassia obtusifolia), giant ragweed (Conyza sumatrensis), common persian violet (Veronica persica), duckweed (Spirodela polyrhiza), cocklebur (Xanthium canadens), goldenrod (Coreopsis lanceolata), common morning glory (Panicum dichotomiflorum), giant milkweed (Asclepias syriaca), celery (Euphorbia maculata), plantain (Plantago asiatica), common red snapper (Rudbeckia laciniata), common amaranthus (Amaranthus palmeri), oats (Avena sativa), cocklebur (Xanthium strumarium, wild oat (Avena sterilis), goosegrass (Eleusine indica), arrowhead (Sagittaria trifolia), Dutch buttercup (Erodium cicutarium), Dutch earwort (Cerastium glomeratum), Oriental daisy (Matricaria matricarioides), chamomile (Matricaria chamomilla), vetch (Vicia angustifolia), vetch (Bromus secalinus), wild oat (Avena fatua), Japanese knotweed (Rotala indica Koehne), Rumex japonicus, Japanese knotweed (Paspalum distichum), foxglove (Bromus remotiflorus), yellow nutsedge (Cyperus esculentus), and burdock (Galium kinuta), Setaria glauca, Pueraria lobata, Eleocharis kuroguwai Ohwi, Sagittaria trifolia Caerulea, Ambrosia trifida, Hydrillaverticillata), Siberian clubweed (Bolboschoenus maritimus (L.) Palla), Corn marigold (Chrysanthemum segetum), Japanese sedge (Cyperus iria), Monochoria vaginalis, Echinochloa colona, ​​Japanese sedge (Alisma plantago-aquatica), Weedy rice (Oryza sativa), Polygonum lapathifolium, Finger millet (Eleusine coracana), Siberian sedge (Schoenoplectus nipponicus), Siberian sedge (Cyperus malaccensis), Quackgrass (Agropyron repens), Shattercane (Sorghum vulgare), Silky bentgrass (Apera spica-venti), Chenopodium album, white clover (Trifolium repens), white morning glory (Datura stramonium), horsetail (Equisetum arvense), annual bluegrass (Poa annua), annual bromegrass (Bromus japonicus), annual foxtail (Alopecurus aequalis), purslane (Portulaca oleracea), goldenrod (Solidago altissima), common sorghum (Sorghum halepense), common mustard (Brassica juncea), common dandelion (Taraxacum officinale), common bindweed (Convolvulus arvensis), water parsley (Oenanthe javanica), bindweed (Polygonum convolvulus), barnyardgrass (Echinochloa oryzicola Vasing, Taiwan ivy (Ischaemum rugosum), Veronica arvensis, Cyperus difformis L., Amaranthus rudis, Timothy (Phleumpratense, Clove Polygonum (Ludwigia prostrata Roxburgh), Dayflower (Commelina communis), Texas Panicum (Panicum texanum), Spurge (Euphorbia helioscopia), Spotted Tit (Festuca parvigluma), Rumex crispus, Shepherd's Purse (Capsella bursa-pastoris), Calendula (Euphorbia pseudochamaesyce), Heart Millet (Brachiaria plantaginea), Lolium multiflorum, Field Thistle (Cirsium japonicum), Black-legged Foxtail (Alopecurus myosuroides), Field Mustard (Sinapis arvensis), Groundnut (Senecio vulgaris), and Galinsoga ciliata, Amaranthus tricolor, Chickweed (Stellaria media), Papyrus (Cyperus papyrus), Cyperus rotundus, Amaranthus spinosus, Polygonum persicaria, Senecio cannabifolius, Cyperus flaccidus, Corn poppy (Papaver rhoeas), Sunflower (Helianthus annuus), Lamium purpureum, Kyllinga gracillima, Lythrum salicaria (Ammannia multiflora), Artemisia canadensis (Erigeron canadensis), Pondweed (Potamogeton distinctus A. Benn), Water hyacinth (Amaranthus tuberculatus), field pansy (Viola arvensis), Japanese thistle (Cirsium purpuratum), ragweed (Ambrosia artemisiifolia), Japanese ragweed (Schoenoplectus tabernaemontani), Japanese ragweed (Veronicahederaefolia, blackgrass (Alopecurus myosuroides), Florida beggarweed (Desmodium tortuosum), plantain (Plantago lanceolata), kochia (Kochia scoparia), burdock (Lolium rigidum), loose-leaved ryegrass (Ammannia coccinea), loose-leaved ryegrass (Lolium perenne), bulrush (Scirpus juncoides Roxburgh), henbit (Lamium amplexicaule), ash grass (Najas graminea), red amaranthus (Amaranthus hybridus), pine needles (Eleocharis acicularis L.), portulaca grandiflora, morning glory (Ipomoea lacunosa), round morning glory (Ipomoea purpurea, common morning glory (Ipomoea hederacea var integriuscula), common dayflower (Commelina bengharensis), black-eared water laurel (Monochoria korsakowii), common serotinus (Cyperus serotinus Rottboel), common chickweed (Elatine triandra Schk), large crabgrass (Digitaria ciliaris), large crabgrass (Digitaria sanguinalis), sorghum (Sorghum bicolor), cleaver (Galium aparine), mugwort (Artemisia princeps), wild pansy (Viola tricolor), wild radish (Raphanus raphanistrum), forget-me-not (Myosotis arvensis), and arrowhead (Alisma canaliculatum). The 3-azabicyclohexane compound represented by the general formula (I) of the present invention or a salt thereof inhibits the growth of these weeds.

[0090] The compound represented by general formula (I) of the present invention or a salt thereof is generally formulated into a convenient form for use according to a conventional method for formulating agrochemicals. That is, the 3-azabicyclohexane compound represented by general formula (I) of the present invention or a salt thereof may be formulated into an appropriate dosage form, such as a suspension, emulsifiable concentrate, solution, wettable powder, water dispersible granule, granule, dust, tablet, pack, etc., by blending the compound with an appropriate inert carrier, or optionally an adjuvant, in an appropriate ratio, and then dissolving, separating, suspending, mixing, impregnating, adsorbing, or attaching the compound to the carrier.

[0091] The composition (agricultural and horticultural herbicide) of the present invention may contain, in addition to the active ingredient, additives commonly used in pesticide formulations or agricultural and horticultural herbicides, as needed. Examples of such additives include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, adhesives, antifreeze agents, anticaking agents, disintegrants, and antidecomposition agents. Other additives, such as preservatives and plant fragments, may also be used as needed. These additives may be used alone or in combination of two or more.

[0092] Examples of solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride, organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose, and plant powders (e.g., sawdust, coconut shells, corn cobs, and tobacco stalks), plastic carriers such as polyethylene, polypropylene, and polyvinylidene chloride, urea, inorganic hollow bodies, plastic hollow bodies, and fumed silica (fumed silica, white carbon). These may be used alone or in combination of two or more.

[0093] Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol; 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; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; ethers such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, and tetrahydrofuran; normal paraffin, naphthene, isopropyl alcohol, and the like. Examples of suitable solvents include aliphatic hydrocarbons such as paraffin, kerosene, and mineral oil, aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate, lactones such as γ-butyrolactone, amides such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, and N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethyl sulfoxide, 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.

[0094] Examples of surfactants used as dispersants, wetting agents, spreading agents and spreaders include 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 ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formalin condensates, polyoxyethylene polyoxypropylene block copolymers, polystyrene polyoxyethylene block polymers, alkyl polyoxyethylene polypropylene block copolymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bisphenyl ethers, polyalkylene benzyl phenyl ethers, polyoxyalkylene styryl phenyl ethers, acetylenic diols, polyoxyalkylene-added acetylenic diols, polyoxyethylene ether-type silicones, and ester-type silicones. nonionic surfactants such as fluorine-based surfactants, polyoxyethylene castor oil, and polyoxyethylene hydrogenated castor oil; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, alkyl benzene sulfonates, alkyl aryl sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkyl naphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkyl naphthalene sulfonic acid, fatty acid salts, polycarboxylates, polyacrylates, N-methyl-fatty acid sarcosinates, resinates, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkyl phenyl ether phosphates; cationic surfactants such as alkyl amine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, and alkyldimethylbenzalkonium chloride;Amphoteric surfactants such as amino acid type or betaine type surfactants may be used alone or in combination of two or more types.

[0095] Examples of 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, polyethylene glycol having an average molecular weight of 6,000 to 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipids (for example, cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidone, copolymers of maleic acid and styrenes, (meth)acrylic acid copolymers, half esters of polymers composed of polyhydric alcohols and dicarboxylic acid anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffin, terpene, polyamide resins, polyacrylates, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, and synthetic resin emulsions.

[0096] Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, diutan gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, and polysaccharides, and inorganic fine powders such as high-purity bentonite and fumed silica (white carbon).

[0097] Examples of colorants 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.

[0098] Examples of antifreezing agents include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0099] Examples of adjuvants for preventing caking or promoting disintegration include polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, metal stearates, cellulose powder, dextrin, methacrylic acid ester copolymers, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers, and starch-polyacrylonitrile graft copolymers.

[0100] Examples of anti-decomposition agents include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol compounds, amine compounds, sulfur compounds, and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.

[0101] Examples of preservatives include potassium sorbate and 1,2-benzothiazolin-3-one.

[0102] Furthermore, other adjuvants such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreeze agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers may also be used as needed.

[0103] 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 herbicide of the present invention. For example, when the agricultural and horticultural herbicide is formulated as a dust, granule, emulsifiable concentrate or wettable powder, the blending ratio is suitably 0.01 to 50% by weight based on the total weight of the agricultural and horticultural herbicide.

[0104] The amount of the 3-azabicyclohexane compound represented by general formula (I) of the present invention or a salt thereof to be used will vary depending on various factors, such as the purpose, target weeds, crop growth conditions, weed infestation tendency, weather, environmental conditions, formulation, application method, application location, application time, etc., but may be appropriately selected depending on the purpose from a range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, of the active ingredient compound per 10 ares.

[0105] The agricultural and horticultural herbicide of the present invention containing the 3-azabicyclohexane compound represented by general formula (I) or a salt thereof as an active ingredient can be directly sprayed onto the foliage of weeds in an amount effective for weed control, either as it is or after being appropriately diluted or suspended in water or the like, in order to control various weeds. In addition, the agricultural and horticultural herbicide can also be used by treating the soil or a cultivation carrier, for example, by immersing seeds in the herbicide, seed dressing, seed treatment of useful plants such as calper treatment, incorporation into the entire soil layer, row application, incorporation into bed soil, treatment with cell seedlings, treatment in planting holes, treatment at the base of plants, top dressing, treatment in rice boxes, application on the water surface, etc.

[0106] Methods for treating seeds of useful plants include, for example, a method in which seeds are soaked in a liquid or solid formulation, diluted or undiluted, to allow the agent to penetrate the seeds, a method in which a solid or liquid formulation is mixed with seeds and coated onto the seed surface, a method in which the formulation is mixed with an adhesive carrier such as a resin or polymer and then coated onto the seeds, a method in which the formulation is sprayed around the seeds at the same time as planting, etc. The "seeds" to be treated in this way refer to plant bodies in the early stages of cultivation used for propagating useful plants, and include, in addition to seeds, bulbs, tubers, seed potatoes, sprouts, bulbils, bulbs, or plant bodies for vegetative propagation for cutting cultivation.

[0107] When carrying out the method of use of the present invention, the term "soil" or "cultivation carrier" for plants refers to a support for cultivating crops, particularly a support for growing roots. The material is not particularly limited, and any material capable of growing useful plants may be used, such as soil, a seedling mat, or water. Specific examples of the material include sand, pumice, vermiculite, diatomaceous earth, agar, a gel-like substance, a polymeric substance, rock wool, glass wool, wood chips, and bark.

[0108] For application to rice seedling boxes, the formulation may vary depending on the application time, such as application at the time of sowing, application during the greening period, or application at the time of transplanting, but may be in the form of a dust, water dispersible granule, granule, or the like. Application can also be by mixing with the culture soil, and the culture soil can be mixed with a dust, water dispersible granule, or granule, for example, by mixing with the bed soil, mixing with the covering soil, or mixing with the entire culture soil. Application can also be simply by layering the culture soil and various formulations alternately.

[0109] Application to paddy fields typically involves spraying solid formulations such as jumbo, pack, granule, and water dispersible granules, or liquid formulations such as flowable and emulsifiable concentrates, onto flooded paddy fields. Additionally, appropriate formulations can be sprayed or injected directly into the soil at the time of rice planting, or mixed with fertilizer. Furthermore, labor-saving application can be achieved by using emulsions, flowables, and other chemical solutions at the source of water flow into paddy fields, such as water inlets and irrigation systems, along with the water supply. When spraying equipment is used, any commonly used equipment can be used, including pancrusher sprayers, manned helicopters, radio-controlled helicopters, radio-controlled boats, drones, one-shot sprayers, powered (manual or automatic) sprayers, carry-type power sprayers, backpack-type power sprayers, and manual sprayers.

[0110] The 3-azabicyclohexane compound represented by general formula (I) of the present invention or a salt thereof can be used in combination with other herbicides, plant growth regulators, phytotoxicity safeners, soil conditioners, fertilizers, etc. in order to extend the range of weeds to be controlled or the optimum control period, or for the purpose of reducing the dosage, and can also be used in combination with agricultural and horticultural insecticides, miticides, nematicides, fungicides, biological pesticides, etc. depending on the application site. Representative compounds are shown below as examples, but the present invention is not limited to these.

[0111] Other agricultural and horticultural insecticides, acaricides, and nematicides used for such purposes include, for example, 3,5-xylyl methylcarbamate (XMC), fenobucarb (BPMC), Bt toxin-based insecticides, CPCBS (chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1,3-dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate (DSP), and O-ethyl O-4-nitrophenyl Phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, acinonapyr, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet idoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isamidofos, isoxathion, isocycloseram, isofenphos, isoprocarbMIPC, epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin, imicyafos, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, esfenvalerate, ethiofen Carb (ethiofencarb), ethion (ethion), ethiprole (ethiprole), etoxazole (etoxazole), etofenprox (ethofenprox), ethoprophos (ethoprophos), etrimfos (etrimfos), emamectin (emamectin), emamectin-benzoate (emamectin-benzoate), endosulfan (endosulfan), empenthrin (empenthrin), oxazosulfyl (oxazosulfyl), oxamyl (oxamyl), oxydemeton-methyl (oxydemeton-methyl), oxydeprofos (oxydeprofos: ESP), oxibendazole (oxibendazole), oxfendazole (oxfendazole), potassium oleate (potassium oleate), sodium oleate (sodium oleate),

[0112] Cadusafos, kappa-bifenthrin, cartap, carbaryl, carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionate, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole lorantraniliprole, chlorethoxyfos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, dicofol, salithion, cyhalodiamide, cyanophosCYAP), diafenthiuron, diamidaphos, cyantraniliprole, theta-cypermethrin, dienochlor, cyetpyrafen, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, diclofenthion (ECP), cycloprothrin, dichlorvos (dichlorvos) DDVP), dichloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofen, diflovidazin, cyproflanilide, cyhexatin, cypermethrin, dimethylvinphos, dimethoate, dimpropyridaz, dimefluthrin, silafluofen, cyromazine, spidoxamat, spinetoram, spinosad, spirodiclofen, spirotetramat, spiropidione, spirobudifen, spiromesifen, sulfiflumin, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin,

[0113] Diazinon, tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap-sodium, thionazin, thiometon, thiolanthraniliprole, DEET, dieldrin, tetrachlorantraniliprole, tyclopyrazoflor, tetrachlorvinphos, tetradifon, tetranil Prole (tetraniliprole), tetramethylfluthrin (tetramethylfluthrin), tetramethrin (tetramethrin), tebupirimfos (tebupirimfos), tebufenozide (tebufenpyrad), tefluthrin (tefluthrin), teflubenzuron (teflubenzuron), demeton-S-methyl (demeton-S-methyl), temephos (temephos), deltamethrin (deltamethrin), terbufos (terbufos), doramectin (doramectin), tralopyril (tralopyril), tralomethrin (tralomethrin), transfluthrin (transfluthrin), triazamate (triazamate), triazuron (triazuron), trichlamide (trichlamide), trichlorphon (trichlorphon: DEP), trifluenfuronate, triflumezopyrium, triflumuron, tolfenpyrad, naledBRP), nicofluprole, nithiazine, nitenpyram, novaluron, noviflumuron,

[0114] Hydroprene, vaniliprole, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxypropyl starch starch, binapacryl, pyflubumide, bifenazate, bifenthrin, pymetrozine, pyraclofos, pyrafluprole, pyridaphenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole role), pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins, fipronil, fenazaquin, fenamiphos, phenisobromorate, fenitrothion (MEP), fenoxycarb, fenothiocarb, fenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoatePAP), fenvalerate, fenpyroximate, fenpropathrin, fenbendazole, fenmezoditiaz, fosthiazate, formetanate, butathiofos , buprofezin, furathiocarb, prallethrin, fluacrypyrim, furazaindolizine, fluazinam, fluazuron, fluensulfone, fluxametamide, fluchlordiniliprole, flucycloxuron, flucythrinate, fluvalinate, flupyradifurone, flufiprole, flupyradifurone, flupyrazofos, flupirimin, flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenprox, flupyroxystrobin, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flupentiofenox, flumethrin, flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite: BPPS), profenofos, broflanilide, profluthrin, propoxur (propoxur: PHC), flometoquin, alpha-bromadiolone, bromopropylate, beta-cyfluthrin, hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiaz, bendiocarb, benzpyrimoxan, bensultap, benzoximate, benfuracarb,

[0115] Phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (PMP), polynactins, formetanate, formothion, phorate, machine oil oil), malathion, milbemycin, milbemycin A, milbemectin, mecarbam, mesulfenphos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam-sodium, methiocarb, methidathionDMTP), methylisothiocyanate, methylneodecanamide, methylparathion, metoxadiazone, methoxychlor, methoxyfenozide, metofluthrin, methoprene, metolcarb, meperfluthrin thrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin, ryanodine, lufenuron, rescalure, resmethrin, lepimectin, rotenone, levamisole hydrochloride Examples of such antihistamines include cyclohexyltin hydrochloride, fenbutatin oxide, morantel tartarate, methyl bromide, tricyclohexyltin hydroxide, calcium cyanamide, calcium polysulfide, sulfur, and nicotine sulfate.

[0116] Agricultural and horticultural fungicides used for similar purposes include, for example, aureofungin, azaconazole, azithiram, acipetax, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, and allyl alcohol.alcohol), aldimorph, amobam, isotianil, isovaledione, isopyrazam, isofetamide, isofetamid, isoflucipram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin n), iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, inpyrfluxam, uniconazole uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole, ethaboxam, ethirimol, etem, ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxiconazole poxiconazole, oxadixyl, oxathiapiprolin, oxycarboxin, copper-8-quinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate, oxolinic acidacid), octhilinone, ofurace, orysastrobin, carbam (metam-sodium), kasugamycin, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamid, quinacetol, quinoxyfen, quinofumelin, chinomethionate , quinomethionate), captafol, captan, chiralaxyl, quinconazole, quintozene, guazatine, cufraneb, cuprobam, coumoxystrobin, glyodin, griseofulvin, climbazole, cresol, kresoxim-methyl, chlozoline chlorzolinate, clotrimazole, chlobenthiazone, chloraniformethan, chloranil, chlorquinox, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, chloroneb,

[0117] Salicylanilide, zalilamid, cyazofamid, diethyl pyrocarbonate, diethofencarb, cyclafuramid, diclocymet, dichlozoline, diclobutrazol, cyclobutrifluram, dichlofluanid, cycloheximide, dichlobentia zox), diclomezine, dicloran, dichlorophen, diclone, disulfiram, ditalimfos, dithianon, diniconazole, diniconazole-M, zineb, dinocap, dinocton, zinos Dinosulfon, dinoterbone, dinobuton, dinopenton, dipymetitrone, dipyrithione, diphenylamine, difenoconazole, cyflufenamid, diflumetorim, cyproconazole zole), cyprodinil, cyprofuram, cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin,Spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazin, tiadinil, thiadifluor, thiabendazole, tioximid, thiochlorfenphim, thiophanate, thiazole ... Thiophanate-methyl, thifluzamide, thicyofen, thioquinox, thiram, decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid acid, tebuconazole, tebufloquin, dodicin, dodine, dodecylbenzenesulfonate bisethylenediamine copper complex(II) (DBEDC), dodemorph, drazoxolon, triadimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol, trichlamide, triclopyricarb, tricyclazole, triticonazole, tridemorph, tributyltin oxide oxide), triflumizole, trifloxystrobin, triforine, tolylfluanid,tolclofos-methyl, tolprocarb,

[0118] Natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin, valifenalate, harpin protein protein), picarbutrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroxyisoxazole-potassium, binapacryl, biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyrazinium Flumid (pyraziflumid), pyrazophos (pyrazophos), pyrapropoin (pyrapropoyne), pyrametostrobin (pyrametostrobin), pyriophenone (pyriofenone), pyridinitril (pyridinitril), pyridiflumetofen (pydiflumetofen), pyrisoxazole (pyrisoxazole), pyridaclomethyl (pyridachlometyl), pyrifenox (pyrifenox), pyribencarb (pyribencarb), pyriminostrobin (pyriminostrobin), pyrimethanil (pyrimethanil), pyroxychlor (pyroxychlor), pyroxyfur (pyroxyfur), pyroquilon (pyroquilon), vinclozolin (vinclozolin), Ferbam (ferbam),Famoxadone, fenapanil, fenamidone, fenaminosulf, phenaminestrobin, fenarimol, fenitropan, fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpicoxamide icoxamid, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate, fuberidazole, blasticidin S (blasticidin-S), furametpyr, furalaxyl, fluacrypyrim, fluazinam, fluindapyr, fluoxastrobin, fluoxapiprolin, fluoxytioconazole, fluotrimazole, fluopicolide, Fluopimomide, fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinconazole, fluconazole, fluconazole-cis, fludioxonil, flusilazole, flusulfamide,Flutianil, flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, furfural, flubeneteram, furmecyclox, flumethylsulfonim, flumetover, flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole, pronitridine, propamocarb, propiconazole onazole, propineb, furophanate, probenazole, bromuconazole, florylpicoxamid, hexachlorobutadiene, hexaconazole, hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox, penconazole, benzamorph, pencycuron, benzohydroxamic acid acid), benzovindiflupyr, bentaluron, benthiazole, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad,penflufen,

[0119] Boscalid, phosdiphen, fosetyl, fosetyl-aluminum, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil oil), maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, methasulfocarb, metazoxolone, metam, metam-sodium, metalaxyl, metalaxyl-M, metarylpicoxamid, metiram, methyl isothiocyanate isothiocyanate, methyldinocap, methyltetraprole, metconazole, metsulfovax, metofuroxam, metominostrobin, metrafenone, mepanipyrim, mefenoxam, mefentrifluconazole, meptyldinocap, mepronil, mebenil, methyl iodide, rabenzazole, methyl bromide, benzalkonium chloride, basic copper chloride, basic copper sulfateExamples of suitable disinfectants include inorganic disinfectants such as copper sulfate and metallic silver, sodium hypochlorite, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, inorganic sulfur, copper compounds such as copper sulfate anhydride, nickel dimethyldithiocarbamate, and 8-hydroxyquinoline copper, zinc sulfate, and copper sulfate pentahydrate.

[0120] Other herbicides used for such purposes include, for example, 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-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, icafolin, aclonifen, azafenidin, Acifluorfen, Aziprotryne, Azimsulfuron, Asulam, Acetochlor, Atrazine, Atraton, Anisuron, Anilofos, Aviglycine, Abscisic Acidacid, amicarbazone, amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amivudine, amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor , alloxydim, arorac, iofensulfuron, isouron, isocarbamide, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isop Isopropalin, isopolinate, isomethiozin, inabenfide, ipazine, iptriazopyrid, ipfencarbazone, iprimidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazamethapyr Imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolauxipyr, indolauxipyr-cyanomethyl, indolebutyric acidacid), uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron-methyl, ethalfluralin, ethalfluralin, ethiolate, ethychlozate ethyl, ethidimuron, ethinofen, ethephon, ethoxysulfuron, ethoxyfen, etnipromid, etofumesate, etobenzanid, epirifenacil, epronaz, erbo n), endothal, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron, oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb,

[0121] Cafenstrole, cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop, quizalofop-P, quizalofop-ethyl lofop-ethyl), xylachlor, quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron, clacyfos, cliodinate, glyphosate, glufosinate, glufosinate-P, credazine, cletodi clethodim, cloxyfonac, clodinafop, clodinafop-propargyl, chlortoluron, clopyralid, cloproxydim, cloprop, chlorbromuron, clofop, clomazone, chlomethoxynil ), chlormethoxyfen, clomeprop, chlorazifop, chlorazine, chlorasulam, chloranocryl, chloramben, chloransulam-methyl, chloridazon, chlorimuron, chlorimuron-ethyl,Chlorsulfuron, chlorthal, chlorthiamid, chlornitrofen, chlorfenac, chlorfenprop, chlorbufam, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil, chloroxuron, chloropon,

[0122] Saflufenacil, cyanazine, cyanatrin, di-allate, diuron, diethamquat, dioxopyritrione, dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron ), cyclopyranil, cyclopyrimorate, dichlorprop, dichlorprop-P, dichlobenil, diclofop, diclofop-methyl, dichromate, dichloralurea, diquat, cisanilide, disul, cis siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, cypyrafluone, diphenamid, difenox Diphenoxuron, difenopenten, difenzoquat, cybutryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine,Dimexano, dimesulfazet, dimethachlor, dimidazon, dimethametryn, dimethenamid, simetryn, simeton, dimepiperate, dimefuron, cinmethylin, swep, s Sulglycapin, sulcotrione, sulfalate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton, sethoxydim, sebuthylazine,

[0123] Terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr, thiafenacil, thiencarbazone, thiencarbazone-methyl, thiocarbazil, thioclorim, thiobencarb, thidiadiamine diazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet, tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumet on), tepraloxydim, tefuryltrione, tembotrione, delachlor, terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, triaziflam, topramezone, riasulfuron, triafamone, triallate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron, tripyrasulfone, trifludimoxazin, triflusulfuron,triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron-methyl, tribenuron, triphop, trifopsime, trimeturon, tolpyralate,

[0124] Naptalam, naproanilide, napropamide, nicosulfuron, nitralin, nitrofen, nitrofluorfen, nipyraclofen, neburon, norflurazon, noruron, barban, paclobutrazol, Paraquat, parafluron, haloxydine, haloxifen, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, bixlozone, picloram , picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, pydanon, pinoxaden, bipyrazone, bifenox, piperophos, hymexazol, pyraquinate, pyraclonil, pyrasulfotole pyrasulfotole, pyrazoxyfen, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, bilanafos, pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium,Pyridate, pyriftalid, pyributicarb, pyriflubenzoxim, pyribenzoxim, pyrimisulfan, pyrimisulfuron, pyriminobac-methyl, fludulfinam, broclozone, pyroxasulfone, pyroxsulam,

[0125] Fenasulam, fenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenothiol, fenoprop, phenobenzuron, fenquinotrione, Fenthiaprop, fenteracol, fentrazamide, fenpyrazone, phenmedipham, phenmedipham-ethyl, butachlor, butafenacil, butamifos, buthiuron, buthidazole, butyrate tylate, buturon, butenachlor, butoxydim, butralin, flazasulfuron, flamprop, furyloxyfen, prinachlor, primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop butyl (fluazifop-butyl), fluazolate, fluchloraminopyr, fluchloraminopyr-tefuryl, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen,Fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium, fluchloralin, flucetosulfuron, fluthiacet, fluthiacet-methyl, flupyrsulfuron, flufenacet cet), flufenoximacil, flufenican, flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn, flumezin, Fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proglinazine, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb (prosulfocarb), propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin,Prohexadione calcium, propoxycarbazone, propoxycarbazone sodium, profoxydim, bromacil, brompyrazone, prometryn, prometon, bromoxynil, bromofenoxim, bromobutide, bromobonil, florasulam, florpyrauxifen,

[0126] Hexachloroacetone, hexazinone, pethoxamid, benazolin, penoxsulam, pebulate, beflubutamid, beflubutamid-M, vernolate, perfluidone, bencarbazone, benquitrione, benzadox, benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide sulide, bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazidehydrazide), mecoprop (mecoprop), mecoprop-P (mecoprop-P), medinoterb (medinoterb), mesosulfuron (mesosulfuron), mesosulfuron-methyl (mesosulfuron-methyl), mesotrione (mesotrione), mesoprazine (mesoprazine), mesoprothrin (methoprotryne), metazachlor (metazachlor), methazole (methazole), metazosulfuron (metazosulfuron), methabenzthiazuron (methabenzthiazuron), metamitron (metamitron), metamifop (metamifop), metam (metam), methalpropalin (methalpropalin), methiuron (methiuron), methio Zolin (methiozolin), methiobencarb (methiobencarb), methyldymron (methyldymron), metoxuron (metoxuron), metoslam (metosulam), metsulfuron (metsulfuron), metsulfuron methyl (metsu1furon-methy1), metflurazon (metflurazon), metobromuron (metobromuron), metobenzuron (metobenzuron), methometon (methometon), metolachlor (metolachlor), metribuzin (metribuzin), mepiquat chloride (mepiquat-chloride), mefenacet (mefenacet), mefluidide (mefluidide), metproxybicyclone (metproxybicyclone),

[0127] Examples of such an antibacterial agent include monalide, monisouron, monunuron, monochloroacetic acid, monolinuron, molinate, morphamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, lancotrione, linuron, rimisoxafen, rimsulfuron, lenacil, rhodethanil, calcium peroxide, and methyl bromide. It can also be used in combination with a biological pesticide such as Xanthomonas campestris, which is used as a herbicide.

[0128] Furthermore, as a safener, for example, 1,8-naphthalic anhydride, isoxadifen-ethyl, furilazole, cyprosulfamide, cyometrinil, dichlormid, dimepiperate, thiencarbazone-methyl, fenchlorazole-ethyl, fenclorim, fluxofenim, flurazole, benoxacor, metcamifen, mefenpyr-diethyl, and the like can also be used in combination.

[0129] Examples of biological pesticides include Agrobacterium radiobacter (e.g., "Galltrol-A (registered trademark)" manufactured by AgBioChem, CA using strain K84, and "Nogall (registered trademark)" manufactured by Becker Underwood, US using strain K1026), Agrobacterium radiobacter (e.g., "Bacteroise (registered trademark)" manufactured by Nippon Nohyaku Co., Ltd. using strain 84), Ampelomyces quisqualis (e.g., "AQ10 (registered trademark)" manufactured by IntrachemBio Italia & Co. KG using strain AQ10), Aspergillus flavus (e.g., "Afla-Guard (registered trademark)" manufactured by Syngenta and "Arizona Cotton Research and Protection (Arizona Cotton Research and Protection)" using strain AF36), and AF36® from Council, US, Afla-Guard from Syngenta using NRRL 21882), Aureobasidium pullulans (e.g., Botector® from bio-ferm, GmbH, which is a mixture of blastospores of strain DSM 14940 and blastospores of strain DSM 14941),

[0130] Bacillus amyloliquefaciens (e.g., Impression Clear (registered trademark) manufactured by Idemitsu Agri Co., Ltd. using strain AT-332, and Avogreen (registered trademark) manufactured by University of Pretoria using strain B246), strain D747 (e.g., Bacstar (registered trademark) manufactured by Etec Crop Solutions, NZ, Shelter (registered trademark) manufactured by Dagutat Biolab, ZA using strain DB101, Artemis (registered trademark) manufactured by Dagutat Biolab, ZA using strain DB102, RhizoVital (registered trademark) manufactured by ABiTEP, DE using strain FZB42, Kodiak (registered trademark) manufactured by Bayer Crop Science AG, DE using strain GB03, and Becker (registered trademark) manufactured by Bayer Crop Science AG, DE using strain MBI600) are also known. Subtilex® from Underwood, US, Amplitude from Marrone Bio Innovations, Inc. using strain F727), Bacillus cepacia (e.g., Deny Stine® from Microbial Products), Bacillus cereus (e.g., Mepichlor® from Arysta, US using strain BP01), Bacillus firmus (e.g., BioNeem® from AgoGreen using strain I-1582),

[0131] Bacillus lacticola (e.g., from Micro Flo Company), Bacillus lactimorbus (e.g., from Micro Flo Company), Bacillus lactis (e.g., from Micro Flo Company), Bacillus laterosporus (e.g., from Agro-Organics, SA under the trademark Bio-Tode), Bacillus licheniformis (e.g., from Novozymes under the trademark EcoGuard Biofungicide using strain SB3086), Bacillus maroccanus (e.g., from Micro Flo Company), Bacillus megaterium (e.g., from Bio Fungicide using strain YFM3.25), Bacillus lacticola (e.g., from Micro Flo Company), Bacillus lactimorbus (e.g., from Micro Flo Company), Bacillus lactis ... Bioarc® from BioArc), Bacillus metiens (e.g., from Micro Flo Company), Bacillus mojavensis (e.g., from Probelte, Sa using strain SR11), Bacillus mycoides (e.g., BmJ® from Certis USA using isolate J.),

[0132] Bacillus nigrificans (e.g., manufactured by Micro Flo Company), Bacillus popilliae (e.g., "Cronox®" manufactured by Bio Crop, CO), Bacillus pumilus (e.g., "Integral F-33®" manufactured by Becker Underwood, US using strain BUF-33, "Yield Shield®" manufactured by Bayer Crop Science AG, DE using strain GB34, "Sonata®" manufactured by Bayer CropScience LP, US using strain QST2808), Bacillus simplex (e.g., "Momiphope Wettable Powder®" manufactured by Arista Life Sciences, Inc. using strain CGF2856), Bacillus sphaericus sphaericus) (e.g., VectoLex® from Valent BioSciences, US, using the serotype H5a5b strain 2362),

[0133] Bacillus subtilis (e.g., "Botokilla Wettable Powder (registered trademark)" manufactured by Idemitsu Agri Co., Ltd., "Taegro (registered trademark)" manufactured by Novozyme Biologicals, Inc. US using strain FZB24, "SERENADE (registered trademark)" manufactured by Bayer CropScience LP, US using strain QST713 / AQ713) MAX (registered trademark), Serenade-DPZ (registered trademark) using strain AQ30002, Ecoshot (registered trademark) manufactured by Kumiai Chemical Co., Ltd. using strain D747, Agrocare Wettable Powder (registered trademark) manufactured by Nisso Green Co., Ltd. using strain HAI-0404, Botopika Wettable Powder (registered trademark) manufactured by Idemitsu Kosan Co., Ltd. using strain MBI600, Batistar Wettable Powder (registered trademark) manufactured by Arista Life Sciences Co., Ltd. using strain Y1336, Companion Biological Fungicide Wettable Powder (registered trademark) manufactured by Growth Products Ltd. using strain GB03), Bacillus thuringiensis (e.g., VectoBac (registered trademark) manufactured by Valent BioSciences, US using strain AM65-52), Bacillus thuringiensis aizawai (Bacillus thuringiensis aizawai) (for example, "XenTari (registered trademark)" manufactured by "Bayer Crop Science AG, DE" using strain ABTS-1857, or "Valent BioSciences,"Florbac WG" manufactured by Certis USA using strain GC-91, "Agree WG Biological Insecticide" manufactured by Certis USA using strain GC-91, Bacillus thuringiensis subspecies. Aegypti (e.g., "Agerin"); Bacillus thuringiensis israelensis (e.g., "Aquabac" manufactured by Becker Microbial Products IL using strain BMP144);

[0134] Bacillus thuringienses kurstaki (e.g., strain BMP 123 manufactured by Becker Microbial Products, IL; strain HD-1 manufactured by Valent BioSciences, US; BMP 123 manufactured by Becker Microbial Products; strain BMP144 / Aquabac manufactured by Becker Microbial Products; strain ABTS-351 manufactured by Valent U.S.A. LLC; strain EG2348 manufactured by Certis USA; strain EG7841 manufactured by Certis USA; strain SA-12 ... Insecticide, Bioprotec PLUS from AEF Global using strain EVB-113-19), Bacillus thuringiensis galleriae (e.g., beetleGONE! from Phyllom BioProducts and boreGONE! from Phyllom BioProducts using strain SDS-502),

[0135] Bacillus thuringiensis var. Colmeri (e.g., TianBaoBTc® from Changzhou Jianghai Chemical Factory), Bacillus thuringienses tenebrionis (e.g., Novodor FC® from BioFa DE using strain NB176), Bacillus thuringiensis var. san diego (e.g., M-One® from Bacillus thuringiensis var. san diego), Beauveria bassiana (e.g., Naturalis® from Intrachem Bio Italia and Bove® from Novozymes using strain CG716), Bacillus thuringiensis var. san diego (e.g., Naturalis® from Intrachem Bio Italia and Bove® from Novozymes using strain CG716), Bacillus thuringiensis var. san diego (e.g., M-One® from Bacillus thuringiensis var. san diego), Bacillus thuringiensis var. san diego (e.g., Naturalis® from Intrachem Bio Italia and Bove® from Novozymes using strain CG716), Bacillus thuringiensis var. san diego (e.g., ... Max (registered trademark), Biolisa Madara (registered trademark) manufactured by Idemitsu Kosan Co., Ltd. using strain F-263, BotaniGard Wettable Powder (registered trademark) manufactured by ARYSTA using strain GHA, balEnce manufactured by Terragena, Inc. using strain HF23, BotaniGard ES manufactured by BioWorks Inc. using strain GHA, and BioCeres WP manufactured by BioSafe Systems using strain ANT-03.

[0136] Beauveria brongniartii (e.g., Beaupro® from Andermatt Biocontrol AG), Bradyrhizobium japonicum (e.g., Optimize® from Novozymes), Burkholderia spp. (e.g., MBI-206 TGAI® from Marrone Bio Innovations using strain A396), Candida oleophila (e.g., Aspire® from Ecogen Inc., US using strain I-82 and Nexy® from BioNext using strain O), Candida saitoana (e.g., Micro Flo Company, US (BASF BIOCURE® from AgriLife), Chaetomium cupreum (e.g., BIOKUPRUM™ from AgriLife), Chaetomium globosum (e.g., Rivadiom® from Rivale), Chromobacterium subtsugae (e.g., Grandevo® from Marrone Bio Innovations using strain PRAA4-1T),

[0137] Cladosporium cladosporioides (e.g., manufactured by Cladosporium cladosporioides), Clonostachys rosea f. catenulate (e.g., manufactured by Verdera, Finland in the form of PRESTOP® using strain J1446), Colletotrichum gloeosporioides (e.g., manufactured by Agriultural Research Initiatives in the form of Collego®), Coniothyrium minitans (e.g., manufactured by Encore Technologies, LLC in the form of Contans® using strain CON / M / 91-08), Cryptococcus albidus (e.g., manufactured by Anchor Bio Technologies, ZA), Delftia acidovorans (e.g., BioBoost® from Brett Young Seeds using strain RAY209), Dilophosphora alopecuri (e.g., Twist Fungus®), Drechsrela monoceras (e.g., Tasmart Herbicide® from Mitsui Chemicals Agro Inc. using strain MTB-951), Entomophthora virulenta (e.g., Vektor® from Ecomic), Fusarium oxysporum oxysporum (e.g., "Marcalite" manufactured by Eisai Seikaken Co., Ltd. using strain 101-2), Fusarium oxysporum (e.g., "Fusaclean (registered trademark)" manufactured by Natural Plant Protection using strain Fo47),

[0138] Gliocladium spp. (e.g., Prestop (registered trademark) manufactured by AgBio Inc. using strain J1446 and W.F. Stoneman Company LLC using strain 321U), Hirsutella thompsonii (e.g., Mycohit (registered trademark) manufactured by Agro Biotech Research Centre, IN), Lactobacillus acidophilus (e.g., Fruitsan (registered trademark) manufactured by Inagrosa Industrias Agrobiologicas, S.A.), Lactobacillus plantarum (e.g., Lactoguard Wettable Powder manufactured by Meiji Seika Pharma Co., Ltd. using strain BY), Lecanicillium lecanii lecanii) (e.g., "Mycotal (registered trademark)" manufactured by Koppert / Arysta using conidia of the strain KV01), Metarhizium anisopliae (e.g., "BIO 1020 (registered trademark)" manufactured by Bayer CropScience using the strain F52, "Pirate Granules (registered trademark)" manufactured by Arysta LifeSciences Inc. using the strain SMZ-2000, and "Bio-Blast" manufactured by LidoChem Inc. using the strain ESC1),

[0139] Metarhizium anisopliae var. acridum (e.g., "Green Muscle®" manufactured by Biological Control Products, and "Becker Underwood,US), Metschnikowia fructicola (e.g., Shemer® from Bayer CropScience), Microdochium dimerum (e.g., ANTIBOT® from Agrauxine, France), Microsphaeropsis ochracea (e.g., Microx® from Prophyta), Monacrosporium phymatopagum (e.g., Nemahiton® from Tomoe Chemical Industry Co., Ltd.), Mucor haemelis (e.g., BioAvard® from Indore Biotech Inputs & Research), Muscodor albus (e.g., strain QST 20799), Myrothecium verrucaria (e.g., "DiTera™" manufactured by Valent Biosciences using strain AARC-0255), Paecilomyces fumosoroseus (e.g., "PreFeRal™ WG" manufactured by Biobest using strain apopka 97, "Preferred Wettable Powder" manufactured by Tokai Bussan Co., Ltd., "No Fly™" manufactured by Natural Industries Inc. (Novozymes company) using strain FE9901), Paecilomyces lilacinus (e.g., "BioAct WG™" manufactured by Prophyta using strain 251),

[0140] Paecilomyces tenuipes (e.g., Gotz A® manufactured by Idemitsu Kosan Co., Ltd. using strain T1), Paecilomyces variotii (e.g., Nemaquim® manufactured by Quimia, MX using strain Q-09), Paenibacillus polymyxa (e.g., Topseed® manufactured by Green Biotech Company Ltd. using strain AC-1), Paenibacillus poppiliae (e.g., Milky spore disease® manufactured by St. Gabriel Laboratories), Pasteuria nishizawae (e.g., Pasteuria "oyacystLF / ST (registered trademark)" manufactured by Pasteuria Bioscience, and "Clariva pn" manufactured by Syngenta using strain Pn1), Pasteuria penetrans (e.g., "Pasteuria (registered trademark)" manufactured by Pasteuria Bioscience), Pasteuria usagae (e.g., "Econem (registered trademark)" manufactured by Pasteuria Bioscience),

[0141] Pantoea agglomerans (e.g., Bloomtime Biological FD Biopesticide manufactured by Nufarm US using strain E325), Pectobacterium carotovorum (e.g., Biokeeper manufactured by Nissan Chemical Co., Ltd. and Ecomate manufactured by Kumiai Chemical Co., Ltd. using strain CGE234M403), Phoma macrostroma (e.g., Phoma H manufactured by Scotts, US using strain 94-44B), Penicillium bilaii (e.g., Jump Start manufactured by Novozymes), Phlebiopsis gigantea (e.g., strain FOC PG B22 / SP1190 / 3.2 (ROTSOP® from Verdera, Finland), Pochonia chlamydosporia var. catenulata (e.g., The National Center of Animal and Plant Health (CENSA);Pseudomonas aureofaciens (e.g., Spot-Less Biofungicide® from EcoSoils Systems, CA using strain TX-1), Pseudomonas chlororaphis (e.g., ATEze® from EcoSoil Systems using strain 63-28 or Cedomon® from Bioagri, S using strain MA342), Pseudomonas fluorescens (e.g., Frostban® from Frost Technology Corp using strain 1629RS), D (registered trademark), "Blightban (registered trademark)" manufactured by "Blightban" using strain A506, "Konae Fukudo (registered trademark)" manufactured by "Taki Chemical Co., Ltd." using strain FPT-9601, "Cell Nae Genki (registered trademark)" manufactured by "Taki Chemical Co., Ltd." which is a mixture of strains FPT-9601 and FPH-9601, "Vegetable Keeper (registered trademark)" manufactured by "Arysta Life Sciences Inc." using strain G7090), Pseudomonas proradix (for example, [Proradix (registered trademark] manufactured by "Sourcon Padena");

[0142] Pseudomonas resinovorans (e.g., Solanacure® from Agricultural Research Council, SA), Pseudomonas syringae (e.g., Biosave® from EcoScience, US using strain MA-4, Frostban C from Frost Technology Corp® using strain 742RS, Bio-save 10LP Biological Fungicide from Jet Harvest Systems using strain ESC10, and Bio-Save 11 LP Biological Fungicide from Jet Harvest Systems using strain ESC11), Pseudomonas spp.) (for example, "Masterpiece Wettable Powder (registered trademark)" manufactured by Nippon Soda Co., Ltd. using strain HAI-0804, and "Momigenki Wettable Powder (registered trademark)" manufactured by Nissan Chemical Industries, Ltd. using strain CAB-02), Pseudozyma aphidis (for example, manufactured by Yissum Research Development Company of the Hebrew University of Jerusalem), Pseudozyma flocculosa (for example, "Sporodex L (registered trademark)" manufactured by Plant Products Co. Ltd, CA using strain PF-A22 UL), Pythium oligandrum (for example, "Polyversum (registered trademark)" manufactured by Bioprepraty, CZ using strain DV74 or M1), Reynoutria sacrinensis sachlinensis) (e.g., REGALIA (registered trademark) manufactured by Marrone BioInnovations, US),

[0143] Rhizopogon amylopogon (e.g., Myco-Sol® from Helena Chemical Company), Rhizopogon fulvigleba (e.g., Myco-Sol® from Helena Chemical Company), Saccharomyces cerevisiae (e.g., Lesaffre et Compagnie, FR), Sclerotinia minor (e.g., Sarritor® from Agrium Advanced Technologies), Serratia entomophila (e.g., Invade® from Wrightson Seeds), Sporothrix insectorum (e.g., Sporothrix Es (registered trademark)"), Steinernema carpocapsae (e.g., Biosafe (registered trademark) manufactured by SDS Biotech Co., Ltd.), Steinernema kushidai (e.g., Shibaichinema manufactured by Kubota Corporation), Steinernema glaseri (e.g., Biotopia (registered trademark) manufactured by Arista Life Sciences Co., Ltd.), Streptomyces acidiscabies (e.g., MBI-005EP (registered trademark) manufactured by Marrone Bioinnovations, CA using strain RL-110T), Streptomyces candidus (e.g., BioBac (registered trademark) manufactured by Biontech, TW using strain Y21007-2),

[0144] Streptomyces galbus (e.g., Mycostop® manufactured by Verdera, strain K61), Streptomyces lydicus (e.g., ACTINOVATE® manufactured by Natural Industries, US, using strain WYEC108), Streptomyces saraceticus (e.g., Clanda® manufactured by A&A Group (Agro Chemical Corp.)), Talaromyces flavus (e.g., FirKeeper® manufactured by Central Glass Co., Ltd., using strain B-422, ToughBlock® manufactured by Idemitsu Kosan Co., Ltd., using strain SAY-Y-94-01, and PROTUS® manufactured by Prophyta, DE, using strain V117b). WG), Trichoderma asperellum (e.g., Isagro using strain ICC 012, T34 Biocontrol® using strain T34 from Biocontrol Technologies, ES, ECO-HOPE® using strain SKT-1 from Kumiai Chemical Industry Co., Ltd.), Trichoderma atroviride (e.g., Esquive® WP from Agrauxine, FR, Tenet® or SENTINEL® using strain LC52 from Agrimm Technologies Ltd, NZ, ECO-HOPE DJ® using strain SKT-1 from Kumiai Chemical Industry Co., Ltd.), Trichoderma gamsii (e.g., Bayer "BIO-TAM™ (registered trademark)" manufactured by CropScience LP, US

[0145] Trichoderma harzianum (e.g., T-Gro 7456 (registered trademark) manufactured by Dagutat Biolab using strain DB103, Trianum-P (registered trademark) manufactured by Koppert using strain ITEM908, Trichoplus (registered trademark) manufactured by Biological Control Products, SA using strain KD, and ROOT PRO (registered trademark) manufactured by Mycontrol Ltd. using strain TH-35), Trichoderma harzianum rifai (e.g., PLANTSHIELD T-22G (registered trademark) manufactured by Firma BioWorks Inc. US using strain T-22 and TRICHODEX (registered trademark) manufactured by Makhteshim Ltd, US using strain T-39), Trichoderma lignorm (e.g., Trichoderma lignorum (e.g., Mycotric® from Futureco Bioscience, ES using strain TL-0601), Trichoderma polysporum (e.g., Binab TF WP® from BINAB Bio-Innovation AB, Sweden), Trichoderma stromaticum (e.g., TRICOVAB® from Ceplac, Brazil), Trichoderma virens (e.g., SOILGARD® from Certis LLC, US using strain GL-21),

[0146] Trichoderma viride (e.g., REMEDIER® WP manufactured by Isagro Ricerca, ITALY using the strain ICC080 and Trianum-P® manufactured by Koppert using the strain TV1), Tsukamurella paurometabola (e.g., HeberNem® manufactured by the strain C-924), Ulocladium oudemansii (e.g., Botry-Zen Ltd. using the strain HRU3),NZ's "Botry-Zen®" and "BotryStop" manufactured by BioWorks Inc. using strain U3), Variovorax paradoxus (e.g., "Field Keeper Wettable Powder®" manufactured by Central Glass using strain CGF4526), ​​VA (Vesicular-Arbuscular Mycorrhiza) mycorrhizal fungi (e.g., "Dr. Kinkon®" manufactured by Idemitsu Agri), Verticillium alboatrum (e.g., "Dutch Trig®" manufactured by Tree Care Innovations using strain WCS850), Verticillium lecanii (e.g., "Vertalec®" manufactured by Arysta Life Sciences Inc. using strain IMI 179172 and "BotryStop" manufactured by BioWorks Inc. using strain IMI 179172), 263817), Xanthomonas campestris (for example, "Camperico Liquid" manufactured by Taki Chemical Co., Ltd.), Xanthomonas campestris pv. poae, Heterorhabditis bacteriophora, Steinernema feltiae, Steinernema kraussei, Steinernema riobrave, Steinernema scapterici, scapterisci), or mutants of these strains that possess all of the distinguishing characteristics of the respective strains, or metabolites produced by the respective strains that exhibit activity against plant pathogenic fungi.

[0147] Representative examples of the present invention will be given below, but the present invention is not limited to these.

[0148] Example 1. Preparation of {3-(2,3-difluorobenzyl)-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl}acetic acid (Compound No. 1-32) To a solution of triethyl phosphonoacetate (4.2 g, 19 mmol) in 2-methyltetrahydrofuran (100 mL), 60% oil-based sodium hydride (0.75 g, 19 mmol) was added in an ice bath and the mixture was allowed to react for 30 minutes. 3-(2,3-Difluorobenzyl)-4-hydroxy-3-azabicyclo[3.1.0]hexan-2-one (1.5 g, 6.3 mmol) was added to the mixture, and the reaction was continued at 80 °C for 4 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was mixed with methanol (3.0 mL), THF (3.0 mL), water (6.0 mL), and lithium hydroxide monohydrate (0.8 g, 19 mmol). After stirring at room temperature for 14 hours, the mixture was concentrated under reduced pressure, and the aqueous layer was washed with ethyl acetate. 2N hydrochloric acid was added until the aqueous layer reached a pH of 4 or less, and the mixture was extracted with chloroform. The organic layer was concentrated and then purified by silica gel column chromatography to obtain {3-(2,3-difluorobenzyl)-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl}acetic acid (1.2 g, 4.3 mmol, trans / cis mixture). Yield: 68%

[0149] Example 2 Preparation of {3-(2,3-difluorobenzyl)-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl}acetic acid 2-(4-methylphenoxy)ethyl ester (Compound No. 1-37) A mixture of {3-(2,3-difluorobenzyl)-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl}acetic acid (0.28 g, 1.0 mmol), 4-dimethylaminopyridine (12 mg, 0.1 mmol), triethylamine (0.7 mL, 5.0 mmol), 2-(4-methylphenoxy)ethanol (0.15 g, 1.5 mmol), propylphosphonic anhydride (50% wt. % ethyl acetate solution, 0.5 mL, 0.94 mmol) and chloroform (3.0 mL) was reacted at room temperature for 14 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was concentrated and then purified by silica gel column chromatography to obtain {3-(2,3-difluorobenzyl)-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl}acetic acid 2-(4-methylphenoxy)ethyl ester (0.29 g, 0.7 mmol trans / cis mixture). Yield: 70%

[0150] Example 3. Preparation of {3-(3-chloro-2-fluorobenzyl)-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl}-N-(1-methyl-1H-1,2,4-triazol-5-yl)acetic acid amide (Compound No. 1-6) A mixture of {3-(2,3-difluorobenzyl)-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl}acetic acid (0.19 g, 0.64 mmol), 4-dimethylaminopyridine (16 mg, 0.13 mmol), triethylamine (0.44 mL, 3.2 mmol), 1-methyl-1H-1,2,4-triazol-5-amine (63 mg, 0.95 mmol), propylphosphonic anhydride (50% wt. % ethyl acetate solution, 0.8 mL, 1.5 mmol), and chloroform (5.0 mL) was reacted at room temperature for 14 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was concentrated and then purified by silica gel column chromatography to give {3-(3-chloro-2-fluorobenzyl)-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl}-N-(1-methyl-1H-1,2,4-triazol-5-yl)acetic acid amide (0.13 g, 0.34 mmol trans / cis mixture). Yield: 52%

[0151] Example 4 Preparation of 3-(3-chloro-2-fluorobenzyl)-4-[2-({(E)-[(4-methylthiophenyl)methylidene]amino}oxy)-2-oxoethyl]-3-azabicyclo[3.1.0]hexan-2-one (Compound No. 1-43) A mixture of {3-(2,3-difluorobenzyl)-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl}acetic acid (0.3 g, 1.0 mmol), 4-dimethylaminopyridine (12 mg, 0.1 mmol), triethylamine (0.7 mL, 5.0 mmol), 4-methylthiobenzaldehyde oxime (0.17 g, 1.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.29 g, 1.5 mmol) and chloroform (5.0 mL) was reacted at room temperature for 14 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was concentrated and then purified by silica gel column chromatography to obtain 3-(3-chloro-2-fluorobenzyl)-4-[2-({(E)-[(4-methylthiophenyl)methylidene]amino}oxy)-2-oxoethyl]-3-azabicyclo[3.1.0]hexan-2-one (0.18 g, 0.42 mmol, trans / cis mixture). Yield: 42%

[0152] Example 5. Method for producing 1-(2-(4-oxo-3-(2,3,6-trifluorobenzyl)-3-azabicyclo[3.1.0]hexan-2-yl)acetic acid amide)cyclopropanecarboxylic acid ethyl ester (Compound No. 1-101) To a mixture of (4-oxo-3-(2,3,6-trifluorobenzyl)-3-azabicyclo[3.1.0]hexan-2-yl)acetic acid (0.3 g, 1.0 mmol), N,N-dimethylformamide (0.15 mL), and chloroform (5.0 mL) was added oxalyl chloride (0.17 mL, 2.0 mmol) in an ice bath, and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated and then dissolved in chloroform (5.0 mL). This solution was added to a mixture of ethyl 1-aminocyclopropanecarboxylate hydrochloride (0.2 g, 1.2 mmol), triethylamine (0.7 mL, 5.0 mmol), and chloroform (5.0 mL) in an ice bath, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was concentrated and then purified by silica gel column chromatography to give 1-(2-(4-oxo-3-(2,3,6-trifluorobenzyl)-3-azabicyclo[3.1.0]hexan-2-yl)acetic acid amide)cyclopropanecarboxylic acid ethyl ester (0.18 g, 0.45 mmol, trans / cis mixture). Yield: 45%

[0153] Reference Example 1. Preparation of 3-(2,3-difluorobenzyl)-3-azabicyclo[3.1.0]hexane-2,4-dione A mixture of 3-oxabicyclo[3.1.0]hexane-2,4-dione (3.7 g, 33.3 mmol), 2,3-difluorobenzylamine (5.0 g, 35 mmol), and chloroform (60 mL) was reacted at 50°C for 2 hours. The reaction solution was concentrated under reduced pressure, and acetic anhydride (30 mL) was added to the residue, followed by reaction at 110°C for 4 hours. The reaction solution was returned to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 7.1 g (30 mmol) of 3-(2,3-difluorobenzyl)-3-azabicyclo[3.1.0]hexane-2,4-dione. Yield: 90%

[0154] Reference Example 2. Preparation of 3-(2,3-difluorobenzyl)-4-hydroxy-3-azabicyclo[3.1.0]hexan-2-one Sodium tetrahydroborate (0.6 g, 16 mmol) was added to a solution of 3-(2,3-difluorobenzyl)-3-azabicyclo[3.1.0]hexane-2,4-dione (3.0 g, 13 mmol) in methanol (66 mL) in an ice bath. After reacting for 1 hour, sodium tetrahydroborate (0.6 g, 16 mmol) was added in an ice bath and reacted for 1 hour. After completion of the reaction, ice-cooled water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was evaporated. The residue was washed with hexane to obtain 3-(2,3-difluorobenzyl)-4-hydroxy-3-azabicyclo[3.1.0]hexan-2-one (3.0 g, 13 mmol). Yield: 99%

[0155] Representative formulation examples and test examples of the present invention are shown below, but the present invention is not limited to these. In the formulation examples, parts are parts by weight.

[0156] Formulation Example 1 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 ingredients are mixed and dissolved uniformly to prepare an emulsifiable concentrate.

[0157] Formulation Example 2: Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above ingredients are uniformly mixed and pulverized to give a dust.

[0158] Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts Calcium lignosulfonate 5 parts The above ingredients are uniformly mixed, and an appropriate amount of water is added, followed by kneading, granulation and drying to give granules.

[0159] Formulation Example 4: Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above ingredients are uniformly mixed and pulverized to give a wettable powder.

[0160] Test Example 1. Test of herbicidal effect on paddy field weeds after emergence. Scirpus juncoides was sown in a test tube containing a hydroponic solution and grown in an artificial growth chamber. Then, a drug containing the compound of the present invention as an active ingredient, prepared according to Formulation Example 1, was diluted with water to a predetermined active ingredient concentration and applied dropwise. The plants were then grown in the artificial growth chamber at 30°C under full light conditions, and the herbicidal effect was investigated 6 days after the drug treatment. The herbicidal effect was evaluated according to the following criteria:

[0161] Criteria for judging herbicidal effect (degree of growth inhibition) 4: 90% to 100% herbicidal effect 3: 70% to 89% herbicidal effect 2: 40% to 69% herbicidal effect 1: 1% to 39% herbicidal effect 0: 0% herbicidal effect

[0162] As a result, the compounds of compound numbers 1-1, 1-2, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-11, 1-12, 1-13, 1-15, 1-16, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-32, 1-34, 1-35, 1-36, 1-37, 1-38, 1-39, 1-42, 1-43, 1-44, 1-45, 1-46, 1-47, and 1-50 exhibited herbicidal effects of 2 points or more according to the above-mentioned evaluation criteria at an active ingredient concentration of 1 ppm.

[0163] Test Example 2. Field pre-emergence treatment test 25 cm ２Cultivation pots were filled with field soil, and seeds of black-edge amaryllis were sown in each pot and uniformly covered with soil. The day after sowing, the emulsion obtained in Formulation Example 1 was diluted to a predetermined concentration and sprayed uniformly onto the soil surface using a small power pressurized sprayer. After the treatment, the pots were cultivated in a greenhouse and the herbicidal effect was investigated 3 weeks after the treatment. The criteria for herbicidal effect were the same as those in Test Example 1. As a result, the compounds of compound numbers 1-4, 1-5, 1-8, 1-9, 1-11, 1-15, 1-16, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-32, 1-34, 1-36, 1-37, 1-38, 1-39, 1-42, and 1-45 showed herbicidal effects of 2 points or more according to the above-mentioned evaluation criteria at a treatment dose of 400 g / ha.

[0164] Test Example 3. Post-emergence treatment test in upland fields 25 cm ２ Cultivation pots were filled with field soil, and seeds of black-edge amaryllis were sown in each pot and covered with soil. The plants were then cultivated in a greenhouse, and when the test weeds reached the one-leaf stage, the emulsion obtained in Formulation Example 1 was diluted to a predetermined concentration and sprayed uniformly onto the plants using a small power pressurized sprayer. The plants were then cultivated in the greenhouse, and the herbicidal effect was investigated three weeks after the chemical treatment. The criteria for judging the herbicidal effect were the same as those in Test Example 1.

[0165] As a result, the compounds of compound numbers 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-11, 1-12, 1-13, 1-15, 1-16, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-32, 1-34, 1-35, 1-36, 1-37, 1-38, 1-39, 1-42, 1-43, 1-44, and 1-45 exhibited herbicidal effects of 2 points or more according to the above-mentioned evaluation criteria at a treatment dose of 400 g / ha.

[0166] The 3-azabicyclohexane compound represented by the general formula (I) of the present invention or a salt thereof has excellent effects as an agricultural and horticultural herbicide.

Claims

1. General formula (1) [In the formula, R １ is (a1) a hydrogen atom; or (a2) (C １ -C ６ ) alkyl group; R ２ and R ５ may be the same or different, and are (b1) a hydrogen atom; (b2) a halogen atom; or (b3) (C １ -C ６ ) alkyl group; R ３ and R ４ may be the same or different, (c1) a hydrogen atom; (c2) a halogen atom; (c3) (C １ -C ６ ) alkyl group; R ６ and R ７ may be the same or different, (d1) a hydrogen atom; (d2) (C １ -C ６ ) alkyl group; (d3) (C ３ -C ６ ) cycloalkyl group; (d4) (C １ -C ６ ) a haloalkyl group; or (d5) R ６ and R ７ may be bonded to each other to form a 3- to 6-membered aliphatic ring. X represents an oxygen atom or a sulfur atom, and Y represents CH ２ , C.H. ２ CH ２ , C(Me)H, or CHF. A represents (e1) (C ３ -C ６ ) cycloalkyl group; (e2) (C ３ -C ６ ) cycloalkyl (C １ -C ６ ) alkyl group; (e3) aryl group; (e4) may be the same or different and are selected from the group consisting of (a) halogen atom, (b) cyano group, (c) nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (e5) an aromatic heterocyclic group; (e6) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (e6) an aromatic heterocyclic group having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; (e7) a non-aromatic heterocyclic group; or (e8) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ Q is a non-aromatic heterocyclic group having 1 to 3 substituents on the ring selected from (f1) a hydroxyl group; (f2) a (C1-C ６ ) alkoxy group; (f3) halo (C1-C ６ ) alkoxy group; (f4) (C ２ -C ６ ) alkenyloxy group; (f5) halo (C ２ -C ６ ) alkenyloxy group; (f6) (C2-C ６ ) alkynyloxy group; (f7) halo (C2-C ６ ) an alkynyloxy group; (f8) (C ３ -C ６ ) cycloalkyloxy group; (f9) halo (C ３ -C ６ ) cycloalkyloxy group; (f10) (C ３ -C ６ ) cycloalkyl(C-C ６ ) alkoxy group; (f11) halo (C ３ -C ６ ) cycloalkyl(C-C ６ ) alkoxy group; (f12) (C1-C ６ ) alkoxy(C1-C ６ ) alkyl group; (f13) (C1-C ６ ) alkoxycarbonyl (C-C ６ ) an alkoxy group; (f14) an aryloxy group; (f15) which may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f16) an aryloxy group having 1 to 5 substituents on the ring selected from aryl (C1-C ６ ) alkoxy group; (f17) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkoxy group; (f18) aryloxy (C1-C ６ ) alkoxy group; (f19) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryloxy (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups ６ ) alkoxy group; (f20) arylthio (C1-C ６ ) alkoxy group; (f21) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) arylthio (C1-C2) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkoxy group; (f22) aromatic heterocyclic oxy group; (f23) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f24) a non-aromatic heterocyclic oxy group; (f25) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f26) a non-aromatic heterocyclic oxy group having 1 to 3 substituents on the ring selected from an aromatic heterocyclic (C １ -C ６ ) alkoxy group; (f27) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) an aromatic heterocycle (C) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; １ -C ６ ) alkoxy group; (f28) non-aromatic heterocycle (C １ -C ６ ) alkoxy group; (f29) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) a non-aromatic heterocyclic ring (C １ -C ６ ) alkoxy group; (f30) amino group; (f31) mono (C1-C ６ ) alkylamino group; (f32) di(C1-C ６ ) alkylamino groups (the alkyl groups may be the same or different); (f33) mono (C ２ -C ６ ) alkenylamino group; (f34) di(C ２ -C ６ ) alkenylamino group (the alkenyl groups may be the same or different); (f35) mono (C ２ -C ６ ) alkynylamino group; (f36) di(C ２ -C ６ ) alkynylamino group (the alkynyl groups may be the same or different); (f37) mono (C ３ -C ６ ) cycloalkylamino group; (f38) mono(C ３ -C ６ ) cycloalkyl(C-C ６ ) alkylamino group; (f39) N—(C1-C ６ ) alkyl-N-(C ２ -C ６ ) alkenylamino group; (f40) N—(C1-C ６ ) alkyl-N-(C ２ -C ６ ) alkynylamino group; (f41) N—(C1-C ６ ) alkyl-N-(C ３ -C ６ ) cycloalkylamino group; (f42) N—(C1-C ６ ) alkyl-N-(C ３ -C ６ ) cycloalkyl(C-C ６ ) alkylamino group; (f43) N,N-di(C1-C ６ ) alkyl (dialkyl groups may be the same or different). sulfamoylamino group; (f44) mono (C1-C ６ ) an alkylsulfonylamino group; (f45) a monoarylamino group; (f46) which may be the same or different and which are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) ( C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f47) a monoarylamino group having 1 to 5 substituents on the ring selected from a monoaryl (C1-C ６ ) alkylamino group; (f48) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C3) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) monoaryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkylamino group; (f49) monoaromatic heterocyclic amino group; (f50) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f51) a non-aromatic heterocyclic group; (f52) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) a non-aromatic heterocyclic group having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; , a non-aromatic heterocyclic group represented by general formula (II): {In the formula, R １０ (g1) a hydrogen atom; (g2) an amino group; (g3) a cyano group; (g4) (C １ -C ６ ) alkyl group; (g5) (C １ -C ６ ) alkylthio group; (g6) mono (C1-C ６ ) alkylamino group; or (g7) di(C1-C ６ ) alkylamino group (the alkyl groups may be the same or different); R １１ is (h1) (C １ -C ６ ) alkyl group; (h2) halo (C １ -C ６ ) alkyl group; (h3) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group; (h4) (C １ -C ６ ) alkoxycarbonyl group; (h5) (C １ -C ６ ) alkylthio (C １ -C ６ ) alkyl group; (h6) halo (C １ -C ６ ) alkylthio (C １ -C ６ ) alkyl group; (h7) (C １ -C ６ ) alkylsulfinyl (C １ -C ６ ) alkyl group; (h8) halo (C １ -C ６ ) alkyl(C １ -C ６ ) alkylsulfinyl group; (h9) (C １ -C ６ ) alkylsulfonyl group (C １ -C ６ ) alkyl; (h10) halo (C １ -C ６ ) alkylsulfonyl (C １ -C ６ ) alkyl group; (h11) aryl group; (h12) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (h13) an aromatic heterocyclic group; (h14) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) an aromatic heterocyclic group having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; R １０ and R １１ (h14) can be bonded to form an aliphatic ring, or (h15) the aliphatic ring may be the same or different, and is (a) a halogen atom, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (i) (C １ -C ６ ) alkoxycarbonyl group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) alkylsulfonyl groups; or a group represented by general formula (III): {In the formula, R １２ and R １３ may be the same or different, (i1) a hydrogen atom; (i2) (C １ -C ６ ) alkyl group; (i3) halo (C １ -C ６ ) alkyl group; (i4) (C1-C ６ ) cycloalkyl group; (i5) aryl (C1-C ６ ) alkyl groups; (i6) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) ( C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C3) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkyl group; or (i7) R １２ and R １３ may be bonded to each other to form a 3- to 6-membered aliphatic ring; １４ is (C １ -C ６ ) represents an alkyl group.} represents a group represented by the formula: • is bonded to C of the C═X group. ] and salts thereof.

2. R １ (a1) a hydrogen atom; or (a2) (C １ -C ６ ) alkyl group; R ２ and R ５が , which may be the same or different, (b1) a hydrogen atom; or (b3) (C １ -C ６ ) alkyl group; R ３ and R ４ may be the same or different, (c1) a hydrogen atom; or (c3) (C １ -C ６ ) alkyl group; R ６ and R ７ (d1) represents a hydrogen atom; X represents an oxygen atom; and Y represents CH ２ , C.H. ２ CH ２ , C(Me)H, or CHF, and A is (e1) (C ３ -C ６ ) cycloalkyl groups; (e4) may be the same or different and are selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (e6) an aryl group having 1 to 5 substituents on the ring selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f2) (C1-C6) alkylsulfonyl group; or (e7) a non-aromatic heterocyclic group; ６ ) alkoxy group; (f8) (C ３ -C ６ ) cycloalkyloxy group; (f12) (C1-C ６ ) alkoxy(C1-C ６ ) alkyl group; (f13) (C1-C ６ ) alkoxycarbonyl (C-C ６ ) an alkoxy group; (f15) may be the same or different, and are: (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo(C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f17) an aryloxy group having 1 to 5 substituents on the ring selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkoxy group; (f19) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryloxy (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups ６ ) alkoxy group; (f21) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) arylthio (C1-C2) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkoxy group; (f23) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f27) an aromatic heterocyclic oxy group having on the ring 1 to 3 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) an aromatic heterocycle (C) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; １ -C ６ ) alkoxy group; (f29) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) a non-aromatic heterocyclic ring (C １ -C ６ ) alkoxy group; (f30) amino group; (f31) mono (C1-C ６ ) alkylamino group; (f37) mono(C ３ -C ６ ) cycloalkylamino group; (f43) N,N-di(C1-C ６ ) alkyl (dialkyl groups may be the same or different) sulfamoylamino group; (f44) mono (C1-C ６ ) alkylsulfonylamino group; (f46) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f50) a monoarylamino group having on the ring 1 to 5 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f51) a non-aromatic heterocyclic group; (f52) which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo(C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ a non-aromatic heterocyclic group having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; a group represented by general formula (II); or a group represented by general formula (III), １０ (g1) a hydrogen atom; (g2) an amino group; or (g4) (C １ -C ６ ) alkyl group; R １１ (h11) represents an aryl group; and R １２ and R １３ may be the same or different, (i1) a hydrogen atom; (i2) (C １ -C ６ ) alkyl group; (i3) halo (C １ -C ６ ) alkyl group; (i4) (C1-C ６ ) cycloalkyl group; (i5) aryl (C1-C ６ ) alkyl group; (i6) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C3) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkyl group; or (i7) R １２ and R １３ may be bonded to each other to form a 3- to 6-membered aliphatic ring; １４ However, (C １ -C ６ 2. The 3-azabicyclohexane compound and salts thereof according to claim 1, wherein:

3. R １ represents (a1) a hydrogen atom; and R ２ and R ５ represents (b1) a hydrogen atom; and R ３ and R ４ (c1) represents a hydrogen atom; and R ６ and R ７ (d1) represents a hydrogen atom; X represents an oxygen atom; and Y represents CH ２ A indicates that (e1) (C ３ -C ６ ) cycloalkyl groups; (e4) may be the same or different, and are: (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo(C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (e6) an aryl group having 1 to 5 substituents on the ring selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f1) an aromatic heterocyclic group having 1 to 3 substituents on the ring selected from (f2) (C1-C ６ ) alkoxy group; (f8) (C ３ -C ６ ) cycloalkyloxy group; (f12) (C1-C ６ ) alkoxy(C1-C ６ ) alkyl group; (f13) (C1-C ６ ) alkoxycarbonyl (C-C ６ ) an alkoxy group; (f15) may be the same or different, and are: (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f17) an aryloxy group having 1 to 5 substituents on the ring selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryl (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups; ６ ) alkoxy group; (f19) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) aryloxy (C1-C2) having 1 to 5 substituents on the ring selected from alkylsulfonyl groups ６ ) alkoxy group; (f23) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f27) an aromatic heterocyclic oxy group having on the ring 1 to 3 substituents selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) an aromatic heterocycle (C) having 1 to 3 substituents on the ring selected from alkylsulfonyl groups; １ -C ６ ) alkoxy group; (f29) may be the same or different, and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ ) a non-aromatic heterocyclic ring (C １ -C ６ ) alkoxy group; (f31) mono(C1-C ６ ) alkylamino group; (f37) mono(C ３ -C ６ ) cycloalkylamino group; (f46) may be the same or different and are (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f50) a monoarylamino group having 1 to 5 substituents on the ring selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) (C １ -C ６ ) alkyl group, (e) halo (C １ -C ６ ) alkyl group, (f) (C １ -C ６ ) alkoxy group, (g) halo (C １ -C ６ ) alkoxy group, (h) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group, (i) (C １ -C ６ ) an alkoxycarbonyl group, (j) (C １ -C ３ ) alkylenedioxy group, (k) halo (C １ -C ３ ) alkylenedioxy group, (l) (C １ -C ６ ) alkylthio group, (m) halo (C １ -C ６ ) alkylthio group, (n) (C １ -C ６ ) alkylsulfinyl group, (o) halo (C １ -C ６ ) alkylsulfinyl group, (p) (C １ -C ６ ) alkylsulfonyl groups, and (q) halo(C １ -C ６ (f51) a non-aromatic heterocyclic group; a group represented by general formula (II); or a group represented by general formula (III), wherein R １０ represents (g1) a hydrogen atom; or (g2) an amino group; and R １１ (h11) represents an aryl group; and R １２ and R １３ may be bonded to each other to form a 3- to 6-membered aliphatic ring; １４ However, (C １ -C ６ 2. The 3-azabicyclohexane compound and salts thereof according to claim 1, wherein:

4. An agricultural and horticultural herbicide comprising the compound or salt thereof according to claim 1 as an active ingredient.

5. A method for using an agricultural and horticultural herbicide, which comprises applying an effective amount of the agricultural and horticultural herbicide according to claim 4 to weeds, soil, paddy fields, fields or cultivation carriers.

6. A method for controlling weeds, which comprises applying an effective amount of the agricultural and horticultural herbicide according to claim 4 to weeds, soil, paddy fields, fields or cultivation carriers.

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