AU2222901A - Aromatic diamide derivatives, chemicals for agricultural or horticultural use and usage thereof - Google Patents

Aromatic diamide derivatives, chemicals for agricultural or horticultural use and usage thereof Download PDF

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AU2222901A
AU2222901A AU22229/01A AU2222901A AU2222901A AU 2222901 A AU2222901 A AU 2222901A AU 22229/01 A AU22229/01 A AU 22229/01A AU 2222901 A AU2222901 A AU 2222901A AU 2222901 A AU2222901 A AU 2222901A
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AU773774B2 (en
Inventor
Shinsuke Fujioka
Takashi Furuya
Eiji Kohno
Hayami Nakao
Tateki Nishida
Kazuyuki Sakata
Akira Seo
Toshiaki Shimizu
Masanori Tohnishi
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Nihon Nohyaku Co Ltd
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Nihon Nohyaku Co Ltd
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Priority claimed from AU93292/98A external-priority patent/AU712421B2/en
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Priority to AU22229/01A priority Critical patent/AU773774B2/en
Priority claimed from PCT/JP2000/009146 external-priority patent/WO2001046124A1/en
Publication of AU2222901A publication Critical patent/AU2222901A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
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    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
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    • C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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    • C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/69—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
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    • C07C233/75—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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    • C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
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  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

qW 150/7 1 DESCRIPTION AROMATIC DIAMIDE DERIVATIVE, AGRICULTURAL AND HORTICULTURAL CHEMICAL AND ITS USAGE TECHNICAL FIELD The present invention relates to aromatic diamide derivatives or salts thereof; an agricultural and horticultural chemical, in particular, an 5 agricultural and horticultural insecticide, which contains said compound as an active ingredient; and a usage of the chemical. BACKGROUND ART JP-A-11-240 857 discloses a compound analogous 10 to the aromatic diamide derivative of the present invention but does not describes working examples, physical properties and the like with respect to the compound of the present invention. DISCLOSURE OF THE INVENTION 15 The production of agricultural and horti cultural crops and the like is still badly damaged by insect pests and the like, and the development of a novel agricultural and horticultural chemical, in particular, agricultural and horticultural insecticide 20 is desired because of, for example, the appearance of insect pests resistant to existing chemicals. In 2 addition, because of the increased population of aged farmers, and the like, various labor-saving application methods are desired and the development of an agri cultural and horticultural chemical having properties 5 suitable for -the application methods is desired. The present inventors earnestly investigated in order to develop a novel agricultural and horti cultural chemical, and consequently found that the aromatic diamide derivative represented by the general 10 formula (I) of the present invention is a novel compound not known in any literature, and the present inventors found a novel use of said derivative as an agricultural and horticultural chemical, in particular, an agricultural and horticultural insecticide and their 15 effective usage, whereby the present invention has been accomplished. That is, the present invention relates to an aromatic diamide derivative represented by the general formula (I): Z' A 1 -B-Rl Q2//QiN-R2 Xn - m(I) Q4 N
Z
2 R2 20 {wherein A' is a (C,-C 8 ) alkylene group; a substituted
(C
1 -C) alkylene group having one or more substituents which may be the same or different and are 3 selected from halogen atoms, cyano group, nitro group, halo (Ci-C6) alkyl groups, (C-C) alkoxy groups, halo (C1 C0) alkoxy groups, (C1-C6) alkylthio groups, halo (C C) alkylthio groups, (Cl-C 6 ) alkylsulfinyl groups, 5 halo (C1-C6) alkylsulfinyl groups, (Ci-C) alkylsulfonyl groups, halo (C-C6) alkylsulfonyl groups, (C-C6) alkyl thio (C1-C6) alkyl groups, (C 1
-C
6 ) alkoxycarbonyl groups and phenyl group; a (C 3 -C)alkenylene group; a substituted
(C
3 -C)alkenylene group having one or more substituents 10 which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo(Cl C6) alkyl groups, (C1-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C-C6) alkylthio groups, halo (C1-C) alkylthio groups, (C-C6) alkylsulfinyl groups, halo (C-C) alkyl 15 sulfinyl groups, (C-C)alkylsulfonyl groups, halo(C C6) alkylsulfonyl groups, (C1-C6) alkylthio (C-C6) alkyl groups, (C 1 -C)alkoxycarbonyl groups and phenyl group; a
(C
3 -C)alkynylene group; or a substituted (C 3 -C)alkyny lene group having one or more substituents which may be 20 the same or different and are selected from halogen atoms, cyano group, nitro group, halo(C 1
-C
6 )alkyl groups, (C1-C6) alkoxy groups, halo (C-C6) alkoxy groups, (C-C6) alkylthio groups, halo (C1-C6) alkylthio groups, (C1-C) alkylsulfinyl groups, halo (C1-C6) alkylsulfinyl 25 groups, (Ci-C6) alkylsulfonyl groups, halo (C1-C6) alkyl sulfonyl groups, (C-C6) alkylthio (C1-C) alkyl groups, ((1-C6)alkoxycarbonyl groups and phenyl group, any of the saturated carbon atoms in the 4 above-mentioned (C 1 -C) alkylene group, substituted (Ci
C
8 ) alkylene group, (C 3 -C)alkenylene group, substituted
(C
3
-C
8 ) alkenylene group, (C 3
-C
8 ) alkynylene group or substituted (C 3 -C)alkynylene group being able to have a 5 (C-C)alkylene group bonded thereto as a substituent, to form a (C 3
-C
6 )cycloalkane ring, and any two of the carbon atoms in the above-mentioned (C-C)alkylene group, substituted (Cl-C) alkylene group, (C 3 -C) alkeny lene group and substituted (C 3 -C)alkenylene group being 10 able to form a (C 3 -C) cycloalkane ring or a (C 3
-C
6 ) cyclo alkene ring together with an alkylene group or an alkenylene group, B is -0- or -N(R 4 )- (wherein R 4 is a hydrogen atom; a (Cl-C 6 ) alkyl group; a halo (C 1 -C,) alkyl group; a 15 (C 3
-C
6 ) alkenyl group; a halo (C3-C6) alkenyl group; a (C 3 C 6 ) alkynyl group; a (C 3 -C) cycloalkyl group; a (C 1 C 6 )alkylcarbonyl group; a halo (C-C6)alkylcarbonyl group; a (C-C)alkoxycarbonyl group; a phenylcarbonyl group; a substituted phenylcarbonyl group having on the ring one 20 or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1
-C
6 ) alkyl groups, halo (Cl-C) alkyl groups, (Ci
C
6 ) alkoxy groups, halo (C-C) alkoxy groups, (C-C6) alkyl thio groups, halo (C1-C) alkylthio groups, (Cl-C 6 ) alkyl 25 sulfinyl groups, halo (Ci-C 6 ) alkylsulfinyl groups, (Ci C6)alkylsulfonyl groups, halo (C-C) alkylsulfonyl groups, mono (C-C) alkylamino groups, and di (C-C6)alkylamino groups whose (C 1
-C
6 )alkyl groups may be the same or 5 different; a phenyl (C 1
-C
4 )alkoxycarbonyl group; a substituted phenyl (C 1
-C
4 )alkoxycarbonyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano 5 group, nitro group, (C-C) alkyl groups, halo (C1-C6) alkyl groups, (C-C6) alkoxy groups, halo (Cl-C) alkoxy groups, (C-C6) alkylthio groups, halo (C-C6) alkylthio groups, (C-C6) alkylsulfinyl groups, halo (C-C) alkylsulfinyl groups, (C-C6) alkylsulfonyl groups, halo (C-C6) alkyl 10 sulfonyl groups, mono (Cl-C 6 )alkylamino groups, and di(Ci
C
6 )alkylamino groups whose (C 1 -C)alkyl groups may be the same or different; a phenyl (C 1
-C
4 )alkyl group; or a substituted phenyl (C-C 4 )alkyl group having on the ring one or more substituents which may be the same or 15 different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 )alkyl groups, halo(Cl-C 6 )alkyl groups, (C1-C6) alkoxy groups, halo (C-C6) alkoxy groups, (C1-C6) alkylthio groups, halo (C 1 -C.) alkylthio groups, (C-C6) alkylsulfinyl groups, halo (C-C6) alkylsulfinyl 20 groups, (Cl-C 6 ) alkylsulfonyl groups, halo (C-C6) alkyl sulfonyl groups, mono (C-C 6 )alkylamino groups, di(Ci
C
6 )alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (C 1 -C0)alkoxycarbonyl groups), R' is a hydrogen atom; a (Cl-C,)alkyl group; a 25 halo (C-C6) alkyl group; a (Cl-C4) alkoxy (Cl-C4) alkyl group; a (C1-C4) alkylthio (Cl-C4) alkyl group; a (C2-C6) alkenyl group; a halo (C2-C6) alkenyl group; a (C 3
-C
6 )alkynyl group; a halo (C 3
-C
6 )alkynyl group; a (C 3
-C
6 ) cycloalkyl 6 group; a halo (C-C6) cycloalkyl group; a phenyl group; a substituted phenyl group having one or more substit uents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, 5 (Ci-C6) alkyl groups, halo (C-C6) alkyl groups, (C1
C
6 ) alkoxy groups, halo (Ci-C6) alkoxy groups, (C1-C) alkyl thio groups, halo (Ci-C) alkylthio groups, (Cl-C.) alkyl sulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (C C6)alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, 10 mono (Cl-C 6 )alkylamino groups, di (C 1
-C
6 )alkylamino groups whose (C 1 -c,)alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; a phenyl(Ci-C 4 )alkyl group; a substituted phenyl(C 1 -C4)alkyl group having on the ring one or more substituents which may be the same 15 or different and are selected from halogen atoms, cyano group, nitro group, (C1-C6) alkyl groups, halo (C-C6) alkyl groups, (C-C) alkoxy groups, halo (Ci-C) alkoxy groups, (C1-C6) alkylthio groups, halo (C-C6) alkylthio groups, (C-C6) alkylsulfinyl groups, halo (C-C6) alkylsulfinyl 20 groups, (C-C6) alkylsulfonyl groups, halo (Ci-C6) alkyl sulfonyl groups, mono (C-C) alkylamino groups, di (C1 C)alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (C-C0)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group 25 having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C6) alkyl groups, halo (C1-C6) alkyl groups, (C1-C6) alkoxy groups, halo (Ci-C) alkoxy groups, 7 (Cl-C6) alkylthio groups, halo (C-C6) alkylthio groups, (Cl-C,) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Cl-C 6 ) alkylsulfonyl groups, halo (Cl-C,) alkyl sulfonyl groups, mono(Cl-C 6 )alkylamino groups, di(C 5 C,)alkylamino groups whose (C 1 -C,)alkyl groups may be the same or different, and (C-C)alkoxycarbonyl groups; -P(=W) (-OR 5 ) (-OR 6 ) (wherein W1 is an oxygen atom or a sulfur atom, and each of R 5 and R', which may be the same or different, is a hydrogen atom; a (C,-C)alkyl 10 group; a halo (Cl-C,)alkyl group; a (C 1
-C
4 ) alkoxy (C 1 C 4 ) alkyl group; a (C 1
-C
4 ) alkylthio (C 1
-C
4 ) alkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro 15 group, (Cl-C.) alkyl groups, halo (Cl-C) alkyl groups, (Ci C6) alkoxy groups, halo (Cl-C.) alkoxy groups, (Cl-C 6 ) alkyl thio groups, halo (Cl-C.) alkylthio groups, (Cl-C) alkyl sulfinyl groups, halo (Cl-C6) alkylsulfinyl groups, (Ci
C
6 )alkylsulfonyl groups, halo(Cl-C 6 )alkylsulfonyl groups, 20 mono (C-C6) alkylamino groups, di (Cl-C.) alkylamino groups whose (C-C,)alkyl groups may be the same or different, and (Cl-C) alkoxycarbonyl groups; a phenyl (C1-C4) alkyl group; a substituted phenyl(Ci-C 4 )alkyl group having on the ring one or more substituents which may be the same 25 or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 )alkyl groups, halo (Cl-C.) alkyl groups, (Cl-CE) alkoxy groups, halo (Cl-C.) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (C-C6) alkylthio groups, 8 (Cl-C) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Cl-CE) alkylsulfonyl groups, halo (Cl-C) alkyl sulfonyl groups, mono(Ci-C)alkylamino groups, di(Cl
C
6 )alkylamino groups whose (C 1
-C
6 )alkyl groups may be the 5 same or different, and (Cl-C)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C) alkyl groups, halo (Cl-C 6 )alkyl 10 groups, (Cl-C) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (Cl-C 6 ) alkylthio groups,
(C
1
-C
6 ) alkylsulfinyl groups, halo (Ci-C.) alkylsulfinyl groups, (Ci-C 6 ) alkylsulfonyl groups, halo (Cl-C 6 ) alkyl sulfonyl groups, mono (CI-C) alkylamino groups, di(Cl 15 C 6 )alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (C 1 -C)alkoxycarbonyl groups, further, R 5 being able to bind to R 6 to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected 20 from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); -C (=W) -N(R 5 ) (R 6 ) (wherein W', R 5 and R 6 are as defined above, R' being able to bind to R 6 to form a 5- to 8 membered ring that may contain one or two atoms which 25 may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, and R 5 being able to bind to R 4 to form a 5- to 8-membered ring 9 that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); -C(=W)-R 5 (wherein W1 and 5 R 5 areas defined above); -C(=Wl)-W'-R' (wherein W's, which may be the same or different, are as defined above, and R' is a (Cl-C.) alkyl group; a halo (C-C6) alkyl group; a (Cl-C 4 )alkoxy(C,-C 4 )alkyl group; a (C,
C
4 ) alkylthio (Ci-C 4 )alkyl group; a phenyl group; a 10 substituted phenyl group having one or more substit uents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C 6 ) alkyl groups, halo (C-C) alkyl groups, (Cl C0) alkoxy groups, halo (C1-C6) alkoxy groups, (C-C6) alkyl 15 thio groups, halo (C-C 6 )alkylthio groups, (Cl-C 6 )alkyl sulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C C6)alkylsulfonyl groups, halo (C-C) alkylsulfonyl groups, mono (C-C6) alkylamino groups, di (C-C6) alkylamino groups whose (Cl-C)alkyl groups may be the same or different, 20 and (C1-C6)alkoxycarbonyl groups; a phenyl (C-C4)alkyl group; a substituted phenyl(Cl-C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C) alkyl groups, halo (C1-C) alkyl 25 groups, (Cl-C)alkoxy groups, halo (C 1
-C
6 )alkoxy groups, (C1-C) alkylthio groups, halo (C-C) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C-C) alkylsulfinyl groups, (C-C) alkylsulfonyl groups, halo (C-C) alkyl- 10 sulfonyl groups, mono (C-C6) alkylamino groups, di (C 1 C 6 )alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (Cl-(,)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group 5 having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1
-C
6 )alkyl groups, halo (Cl-C 6 )alkyl groups, (C-C6) alkoxy groups, halo (C-C6) alkoxy groups, (Ci-C 6 ) alkylthio groups, halo (C-C) alkylthio groups, 10 (C-C) alkylsulfinyl groups, halo (C-C) alkylsulfinyl groups, (C-C) alkylsulfonyl groups, halo (C-C 6 ) alkyl sulfonyl groups, mono(Cl-C)alkylamino groups, di(Cl C6)alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups); 15 -S0 2 -R' (wherein R' is as defined above); -S0 2
-N(R
5 ) (R 6 ) (wherein R 5 and R 6 are as defined above, R 5 being able to bind to R 6 to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur 20 atom and nitrogen atom, between adjacent carbon atoms constituting the ring, and R' being able to bind to R 4 to form a 5- to 8-membered ring that may contain three or four atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen 25 atom, between adjacent carbon atoms constituting the ring); -N(R') (R 6 ) (wherein R' and R 6 are as defined above, R 5 being able to bind to R' to form a 5- to 8 membered ring that may contain one or two atoms which 11 may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, and R' being able to bind to R' to form a 5- to 8-membered ring 5 that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); or -N=C(R 5
)R
6 (wherein R' and R 6 are as defined above, R 5 being able to bind to R 6 10 to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); in the case of B being -N(R)-, R' being able to 15 be -OR 5 (wherein R 5 is as defined above), -C(W 2
)-N(R
5
)R
6 (wherein W 2 is =CH-N0 2 , =N-N0 2 or =N-CN, and R 5 and R 6 are as defined above, R or R 6 being able to bind to R' to form a 5- to 8-membered ring that may contain two or three atoms which may be the same or different and are 20 selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring) or -C(W 2 )-W'-R' (wherein Wi, W 2 and R' are as defined above, R being able to bind to R' to form a 5 to 8-membered ring that may contain two or three atoms 25 which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring), and R' being able to bind to A' to form a 5- to 8- 12 membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, 5 each of R 2 and R 3 , which may be the same or different, is a hydrogen atom, a (C 3 -C) cycloalkyl group or -A2-R' (wherein
A
2 is -C(=O)-, -C (=S) -, -C (=NR 9 ) (wherein R' is a hydrogen atom, a (Ci-C.) alkyl group, a (Ci-C.) alkoxy group, a mono (Ci-C.) alkylamino group, a 10 di (Ci-C 6 )alkylamino group whose (C 1
-C
6 )alkyl groups may be the same or different, a (Ci-C,)alkoxycarbonyl group, a phenyl group, or a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano 15 group, nitro group, (Ci-C 6 )alkyl groups, halo (Ci-C 6 )alkyl groups, (Ci-C.) alkoxy groups, halo (Ci-C 6 ) alkoxy groups,
(C
1
-C
6 ) alkylthio groups, halo (c0-C 6 ) alkylthio groups, (Cl-C 6 ) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Ci-C 6 ) alkylsulfonyl groups, halo (Ci-C) alkyl 20 sulfonyl groups, mono (Ci-C.) alkylamino groups, di(Cl
C
6 )alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Ci-C,)alkoxycarbonyl groups), a (Cl-C) alkylene group, a halo (Ci-C 8 ) alkylene group, a
(C
3
-C
6 )alkenylene group, a halo (C 3
-C
6 )alkenylene group, a 25 (C 3 -C,)alkynylene group or a halo (C 3 -C,) alkynylene group, (1) in the case of A 2 being -C(=O)-,
-C(=S)
or -C(=NR 9 )- (wherein R' is as defined above), R is a hydrogen atom; a (Ci-C 6 ) alkyl group; a halo (Ci-C) alkyl 13 group; a (C3-C6) cycloalkyl group; a halo (C3-C6) cycloalkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano 5 group, nitro group, (C 1
-C
6 ) alkyl groups, halo (Cl-C 6 )alkyl groups, (Cl-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C1-C) alkylthio groups, halo (Cl-C 6 ) alkylthio groups, (C-CE) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (C 1 -C) alkylsulfonyl groups, halo (Cl-C) alkyl 10 sulfonyl groups, mono(C-C)alkylamino groups, di((l
C
6 )alkylamino groups whose (C 1
-C
6 )alkyl groups may be the same or different, and (C-C)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same 15 or different and are selected from halogen atoms, cyano group, nitro group, (C 1
-C
6 ) alkyl groups, halo (C1-C6) alkyl groups, (C-C6) alkoxy groups, halo (C-C6) alkoxy groups, (C1-C6) alkylthio groups, halo (C1-C) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C 1
-C
6 ) alkylsulfinyl 20 groups, (C-C6) alkylsulfonyl groups, halo (C 1
-C
6 ) alkyl sulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di (Ci
C
6 )alkylamino groups whose ((l-C 6 )alkyl groups may be the same or different, and (C-C)alkoxycarbonyl groups; or
-A
3 -R1 0 (wherein A 3 is -0-, -S- or -N(R")- (wherein R" is 25 a hydrogen atom; a ((l-C)alkylcarbonyl group; a halo(Ci C)alkylcarbonyl group; a (C0-C)alkoxycarbonyl group; a phenylcarbonyl group; a substituted phenylcarbonyl group having one or more substituents which may be the 14 same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C.) alkyl groups, halo (Ci
C
6 ) alkyl groups, (C-C6) alkoxy groups, halo (C 1
-C
6 ) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (C1-C6) alkylthio 5 groups, (C 1
-C
6 ) alkylsulfinyl groups, halo (Cl-C 6 ) alkyl sulfinyl groups, (C-C6) alkylsulfonyl groups, halo (Cl C6) alkylsulfonyl groups, mono (C-C6) alkylamino groups, di (Cl-C 6 ) alkylamino groups whose (C-C) alkyl groups may be the same or different, and (C-C0 6 )alkoxycarbonyl 10 groups; a phenyl (C 1
-C
4 )alkoxycarbonyl group; or a substituted phenyl(C-C 4 )alkoxycarbonyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C) alkyl groups, halo (C-C6) alkyl 15 groups, (C1-C6) alkoxy groups, halo (C-C) alkoxy groups, (C1-C6) alkylthio groups, halo (C1-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C-C) alkylsulfinyl groups, (C-C6) alkylsulfonyl groups, halo (C-C6) alkyl sulfonyl groups, mono (Ci-C 6 )alkylamino groups, di(Ci 20 C) alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (C-C0)alkoxycarbonyl groups), and R1 0 is a (Ci-C 6 )alkyl group; a halo (CI-C6) alkyl group; a (C3-C6) alkenyl group; a halo (C3-C6) alkenyl group; a (C3-C6) alkynyl group; a halo (C3-C) alkynyl group; a (C3 25 C.) cycloalkyl group; a halo (C 3 -C) cycloalkyl group; a (C1-C6) alkylcarbonyl group; a halo (C1-C) alkylcarbonyl group; a (C-C0)alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more substit- 15 uents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C.) alkyl groups, halo (C 1
-C
6 ) alkyl groups, (Ci C.) alkoxy groups, halo (C 1
-C
6 ) alkoxy groups, (C 1
-C
6 ) alkyl 5 thio groups, halo (C 1
-C
6 ) alkylthio groups, (C 1
-C
6 ) alkyl sulfinyl groups, halo (Ci-C.) alkylsulfinyl groups, (C 1 C 6 )alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, mono (C 1
-C
6 ) alkylamino groups, di (C 1
-C
6 ) alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, 10 and (C 1
-C
6 )alkoxycarbonyl groups; a phenyl (Cl-C 4 )alkyl group; a substituted phenyl(Ci-C 4 )alkyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C,) alkyl groups, halo (Ci-C.) alkyl groups, (C 1 15 C 6 ) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (Ci-C 6 ) alkyl thio groups, halo (Cl-C 6 ) alkylthio groups, (Ci-C,) alkyl sulfinyl groups, halo (C 1
-C
6 ) alkylsulfinyl groups, (C 1 C 6 )alkylsulfonyl groups, halo (Cl-C) alkylsulfonyl groups, mono (Ci-C.) alkylamino groups, di (Ci-C 6 ) alkylamino groups 20 whose (Cl-C 6 )alkyl groups may be the same or different, and (C-C)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, 25 (C 1 -C) alkyl groups, halo (Cl-C 6 ) alkyl groups, (C 1 C 6 ) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (Cl-C) alkyl thio groups, halo (C 1
-C
6 ) alkylthio groups, (C 1
-C
6 ) alkyl sulfinyl groups, halo (Ci-C 6 ) alkylsulfinyl groups, (C 1
-
16 C6)alkylsulfonyl groups, halo (C-C6)alkylsulfonyl groups, mono (C1-C6) alkylamino groups, di (C-C) alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (C1-C6) alkoxycarbonyl groups), 5 (2) in the case of A 2 being a (C-C)alkylene group, a halo (C,-C) alkylene group, a (C 3 -C) alkenylene group, a halo (C 3 -C)alkenylene group, a (C 3 -C) alkynylene group or a halo(C 3
-C
6 )alkynylene group, R' is a hydrogen atom; a halogen atom; a cyano group; a nitro group; a 10 (C 3
-C
6 ) cycloalkyl group; a halo (C 3
-C
6 ) cycloalkyl group; a (Cl-C)alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more substit uents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, 15 (C-C6) alkyl groups, halo (C-C6) alkyl groups, (C C6) alkoxy groups, halo (C-C6) alkoxy groups, (C1-C) alkyl thio groups, halo (C-C6) alkylthio groups, (C-C6) alkyl sulfinyl groups, halo (C-C) alkylsulfinyl groups, (C C)alkylsulfonyl groups, halo (C-C) alkylsulfonyl groups, 20 mono (C-C) alkylamino groups, di (C 1
-C
6 )alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and ((-C)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are 25 selected from halogen atoms, cyano group, nitro group, (C-C) alkyl groups, halo (C1-C6) alkyl groups, (C C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C-C6) alkyl thio groups, halo (C-C6) alkylthio groups, (C1-C) alkyl- 17 sulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (C 1 C 6 ) alkylsulfonyl groups, halo (Cl-C 6 ) alkylsulfonyl groups, mono (Ci-C.) alkylamino groups, di (C 1
-C
6 ) alkylamino groups whose (C 1 -C,)alkyl groups may be the same or different, 5 and (Cl-C,)alkoxycarbonyl groups; or -A 4 -R (wherein A 4 is -0-, -S- 1 -SO-, -SO2-, -N(R")- (wherein R" is as defined above), -C(=O)-, or -C(=N-OR 3 ) (wherein R 3 is a hydrogen atom, a (Cl-C 6 )alkyl group, a halo (C,-C 6 )alkyl group, a (C 3
-C
6 ) alkenyl group, a halo (C 3
-C
6 ) alkenyl 10 group, a (C 3
-C
6 ) alkynyl group, a halo (C 3
-C
6 ) alkynyl group, a (C 3
-C
6 ) cycloalkyl group, a phenyl (C 1
-C
4 ) alkyl group, or a substituted phenyl(Cl-C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, 15 cyano group, nitro group, (C 1
-C
6 )alkyl groups, halo(Cl
C
6 ) alkyl groups, (C 1 -C,) alkoxy groups, halo (Cl-C.) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (Cl-C 6 ) alkylthio groups, (Ci-C 6 ) alkylsulfinyl groups, halo (Cl-C.) alkyl sulfinyl groups, (Cl-C 6 ) alkylsulfonyl groups, halo (C1 20 C 6 ) alkylsulfonyl groups, mono (Cl-C.) alkylamino groups, di (Cl-C) alkylamino groups whose (Ci-C,)alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups), (i) in the case of A 4 being -0-, -S-, -SO-, -S02- or 25 -N(R")- (wherein R" is as defined above), R 12 is a hydrogen atom; a (Cl-C 6 )alkyl group; a halo (Cl-C 6 ) alkyl group; a (C 3 -C,) alkenyl group; a halo (C 3
-C
6 ) alkenyl group; a (C 3 -C,)alkynyl group; a halo (C 3 -C)alkynyl 18 group; a (C 3 -C0) cycloalkyl group; a halo (C3-C6) cycloalkyl group; a (C-C6) alkylcarbonyl group; a halo (C1-C6) alkyl carbonyl group; a (C-C6)alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more 5 substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C6) alkyl groups, halo (C 1
-C
6 ) alkyl groups, (Cl C.) alkoxy groups, halo (C-C) alkoxy groups, (Cl-C 6 ) alkyl thio groups, halo (Cl-C 6 )alkylthio groups, (Cl-C 6 )alkyl 10 sulfinyl groups, halo (C-C6) alkylsulfinyl groups, (C
C
6 )alkylsulfonyl groups, halo (C-C6)alkylsulfonyl groups, mono (C1-C6) alkylamino groups, di (Cl-C 6 ) alkylamino groups whose ((l-C 6 )alkyl groups may be the same or different, and (C1-C6) alkoxycarbonyl groups; a phenyl (C1-C4) alkyl 15 group; a substituted phenyl((l-C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1
-C
6 ) alkyl groups, halo (Cl-C 6 ) alkyl groups, (C1-C6) alkoxy groups, halo (C1-C6) alkoxy groups, 20 (C1-C6) alkylthio groups, halo (C 1
-C
6 ) alkylthio groups, (C,-C,) alkylsulfinyl groups, halo (C-C6) alkylsulfinyl groups, (C-C6)alkylsulfonyl groups, halo (C-C6)alkyl sulfonyl groups, mono(C-C)alkylamino groups, di(C, C6)alkylamino groups whose (C-C 6 )alkyl groups may be the 25 same or different, and (Cl-C)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano 19 group, nitro group, (C 1
-C
6 ) alkyl groups, halo (Ci-C 6 ) alkyl groups, (C 1 -C,) alkoxy groups, halo (Cl-C 6 ) alkoxy groups,
(C
1 -C.) alkylthio groups, halo (Ci-C.) alkylthio groups, (Ci-C 6 ) alkylsulfinyl groups, halo (Ci-C 6 ) alkylsulfinyl 5 groups, (Ci-C 6 ) alkylsulfonyl groups, halo (C 1 -C.) alkyl sulfonyl groups, mono (Ci-C 6 )alkylamino groups, di(C 1 C 6 ) alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups, (ii) in the case of A 4 being -C(=O)- or -C(=NOR) 10 (wherein R 13 is as defined above), R is a hydrogen atom; a (C 1
-C
6 ) alkyl group; a halo (Cl-C) alkyl group; a
(C
2
-C
6 ) alkenyl group; a halo (C 2
-C
6 ) alkenyl group; a (C 3 Cj)cycloalkyl group; a halo (C 3
-C
6 )cycloalkyl group; a
(C
1
-C
6 ) alkoxy group; a halo (C 1
-C
6 ) alkoxy group; a (Cl 15 Cj)alkylthio group; a halo (C 1
-C
6 )alkylthio group; a mono (C 1
-C
6 ) alkylamino group; a di (C,-C 6 ) alkylamino group whose (Cl-C 6 )alkyl groups may be the same or different; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different 20 and are selected from halogen atoms, cyano group, nitro group, (CI-C) alkyl groups, halo (C 1
-C
6 ) alkyl groups, (C 1 C 6 ) alkoxy groups, halo (C 1
-C
6 ) alkoxy groups, (CI-C 6 ) alkyl thio groups, halo (Cl-C 6 )alkylthio groups, (Cl-C 6 )alkyl sulfinyl groups, halo (C 1
-C
6 ) alkylsulfinyl groups, (Cl 25 C 6 ) alkylsulfonyl groups, halo (Ci-C 6 ) alkylsulfonyl groups, mono (Ci-C 6 ) alkylamino groups, di (C 1
-C
6 ) alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (C 1
-C
6 )alkoxycarbonyl groups; a phenylamino group; a 20 substituted phenylamino group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 ) alkyl groups, halo (Ci-C.) alkyl groups, (C 1 5 C 6 ) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (C 1 -C,) alkyl thio groups, halo (C 1
-C
6 ) alkylthio groups, (C 1
-C
6 ) alkyl sulfinyl groups, halo (C,-C 6 ) alkylsulfinyl groups, (C 1 C 6 )alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, mono (C 1
-C
6 ) alkylamino groups, di (C-C 6 ) alkylamino groups 10 whose (Cl-C 6 )alkyl groups may be the same or different, and (C-C,)alkoxycarbonyl groups; a phenyloxy group; a substituted phenyloxy group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro 15 group, (C 1
-C
6 ) alkyl groups, halo (C 1
-C
6 ) alkyl groups, (C 1 C,) alkoxy groups, halo (C 1 -C.) alkoxy groups, (Cl-C 6 ) alkyl thio groups, halo (C 1
-C
6 ) alkylthio groups, (C 1
-C
6 ) alkyl sulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Ci
C
6 ) alkylsulfonyl groups, halo (C 1
-C
6 ) alkylsulfonyl groups, 20 mono (Cl-C 6 )alkylamino groups, di(C--C 6 )alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; a phenylthio group; a substituted phenylthio group having on the ring one or more substituents which may be the same or different 25 and are selected from halogen atoms, cyano group, nitro group, (C 1
-C
6 ) alkyl groups, halo (C 1
-C
6 ) alkyl groups, (C 1 C 6 ) alkoxy groups, halo (C 1
-C
6 ) alkoxy groups, (C 1 -C,) alkyl thio groups, halo (Ci-C 6 )alkylthio groups, (C 1
-C
6 )alkyl- 21 sulfinyl groups, halo (Cl-C.) alkylsulfinyl groups, (CI
C
6 )alkylsulfonyl groups, halo (C-C) alkylsulfonyl groups, mono (C-C) alkylamino groups, di (C,-C.) alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, 5 and (Cl-C)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 ) alkyl groups, halo (Cl-C 6 ) alkyl groups, (Cl 10 C) alkoxy groups, halo (C1-C) alkoxy groups, (C-C) alkyl thio groups, halo (C-C6) alkylthio groups, (Cl-C,) alkyl sulfinyl groups, halo(Cl-C)alkylsulfinyl groups, (C,
C
6 )alkylsulfonyl groups, halo (C,-C,) alkylsulfonyl groups, mono (C-C) alkylamino groups, di (C-C 6 ) alkylamino groups 15 whose (C,-C,)alkyl groups may be the same or different, and (C-C6) alkoxycarbonyl groups)), further, R 2 being able to bind to A' or R1 to form a 5- to 8-membered ring that may contain one to three atoms which may be the same or different and are 20 selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, each of Q1 through Q' is a carbon atom or a nitrogen atom, each of Xs, which may be the same or 25 different, is a halogen atom; a cyano group; a nitro group; a (C 3 -C) cycloalkyl group; a halo (C 3
-C
6 ) cycloalkyl group; a (Cl-C)alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more substit- 22 uents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C1-C) alkyl groups, halo (C1-C6) alkyl groups, (C1 C.) alkoxy groups, halo (C 1 -C.) alkoxy groups, (Cl-C6) alkyl 5 thio groups, halo (C-C6) alkylthio groups, (Ci-C6) alkyl sulfinyl groups, halo (C1-C) alkylsulfinyl groups, (C
C
6 )alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, mono (Ci-C) alkylamino groups, di (Ci-C.) alkylamino groups whose (C 1 -C,)alkyl groups may be the same or different, 10 and (Ci-C,)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group,
(C
1
-C
6 ) alkyl groups, halo (Ci-C 6 ) alkyl groups, (C 1 15 C 6 ) alkoxy groups, halo (C1-C) alkoxy groups, (C 1
-C
6 ) alkyl thio groups, halo (Ci-C.) alkylthio groups, (C1-C) alkyl sulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Cl C)alkylsulfonyl groups, halo (C-C6)alkylsulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di (Ci-C 6 ) alkylamino groups 20 whose (Cl-C)alkyl groups may be the same or different, and (C-C6)alkoxycarbonyl groups; or -A 5 -R (wherein A' is -0-, -S-, -SO-, -SO2-, -C(=0)-, -C(=NOR1 3 ) (wherein R1 3 is as defined above), a (Cl-C0)alkylene group, a halo (C1-C) alkylene group, a (C 2 -C)alkenylene group, a 25 halo (C 2 -C)alkenylene group, a (C 2 -C)alkynylene group or a halo (C3-C)alkynylene group, (1) in the case of A 5 being -0-, -S-, -SO- or
-SO
2 -, R' is a halo (C 3
-C
6 ) cycloalkyl group; a halo (C 3
-
23 CE)cycloalkenyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C)alkyl groups, 5 halo (C1-CE) alkyl groups, (Cl-C) alkoxy groups, halo (Cl
C
6 ) alkoxy groups, (Cl-C) alkylthio groups, halo (C 1 C6) alkylthio groups, (C-C) alkylsulfinyl groups, halo (C-C) alkylsulfinyl groups, (Cl-C) alkylsulfonyl groups, halo (Cl-C 6 ) alkylsulfonyl groups, mono (Cl 10 C 6 )alkylamino groups, di(Cl-C 6 )alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (C-C,)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are 15 selected from halogen atoms, cyano group, nitro group, (Cl-C) alkyl groups, halo (Cl-CE) alkyl groups, (Cl C6) alkoxy groups, halo (Cl-CE) alkoxy groups, (Cl-C) alkyl thio groups, halo (Cl-C) alkylthio groups, (Cl-C) alkyl sulfinyl groups, halo (Cl-C) alkylsulfinyl groups, (Cl 20 CE)alkylsulfonyl groups, halo (Cl-CE) alkylsulfonyl groups, mono (Cl-C) alkylamino groups, di (Cl-C) alkylamino groups whose (C-C)alkyl groups may be the same or different, and (C-C)alkoxycarbonyl groups; or -A 6 -R" (wherein A 6 is a (C 1
-C
6 )alkylene group, a halo (C-C 6 )alkylene group, 25 a (C3-CE) alkenylene group, a halo (C3-C) alkenylene group, a (C3-C) alkynylene group or a halo (C3-C) alkynylene group, and R1 5 is a hydrogen atom; a halogen atom; a (C3 C) cycloalkyl group; a halo (C 3 -C) cycloalkyl group; a 24
(C-C
6 )alkoxycarbonyl group; a phenyl group; a substi tuted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C, 5 C6) alkyl groups, halo (Cl-C6) alkyl groups, (Cl-C 6 ) alkoxy groups, halo (C 1 -C.) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (Cl-C 6 ) alkylthio groups, (Cl-C 6 ) alkylsulfinyl groups, halo (C 1
-C
6 ) alkylsulfinyl groups, (Cl-C 6 ) alkyl sulfonyl groups, halo (C 1
-C
6 ) alkylsulfonyl groups, 10 mono (Cl-C 6 ) alkylamino groups, di (Cl-C 6 ) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; or -A-R" (wherein A' is -0-, -S-, -SO- or -SO 2 -, and R" is a (C 1
-C
6 ) alkyl group; a halo (C 1
-C
6 ) alkyl group; a (C 3
-C
6 )alkenyl group; 15 a halo (C 3
-C
6 ) alkenyl group; a (C-C 6 )alkynyl group; a halo (C 3
-C
6 ) alkynyl group; a (C 3
-C
6 ) cycloalkyl group; a halo (C 3
-C
6 )cycloalkyl group; a phenyl group; a substi tuted phenyl group having one or more substituents which may be the same or different and are selected 20 from halogen atoms, cyano group, nitro group, (C 1 C6)alkyl groups, halo (Ci-C 6 )alkyl groups, (Cl-C 6 )alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (C 1 -C6) alkylthio groups,
(C
1 -C6) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Cl-C 6 ) alkyl 25 sulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, mono (Cl-C.) alkylamino groups, di (Cl-C.) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups; a heterocyclic group; 25 or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 ) alkyl groups, halo (C 1 -C.) alkyl groups, (C 1 5 C.) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (Cl-C.) alkyl thio groups, halo (Cl-C 6 ) alkylthio groups, (Cl-C.) alkyl sulfinyl groups, halo (C 1
-C
6 ) alkylsulfinyl groups, (Cl
C
6 ) alkylsulfonyl groups, halo (Cl-C.) alkylsulfonyl groups, mono (C 1
-C
6 ) alkylamino groups, di (C 1
-C
6 ) alkylamino groups 10 whose (Cl-C,)alkyl groups may be the same or different, and (C 1 -C) alkoxycarbonyl groups), (2) in the case of A 5 being -C(=O)- or -C(=NOR1 3 )- (wherein R" is as defined above), R is a (Cl-C 6 ) alkyl group; a halo (Cl-C 6 ) alkyl group; a (C2 15 C 6 )alkenyl group; a halo (C 2 -C,) alkenyl group; a (C 3 C,)cycloalkyl group; a halo (C 3
-C
6 )cycloalkyl group; a (Cl-C,)alkoxy group; a (Cl-C,)alkylthio group; a mono(Cl
C
6 )alkylamino group; a di(C 1 -C.)alkylamino group whose (Cl-C,)alkyl groups may be the same or different; a 20 phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C) alkyl groups, halo (Cl-CE) alkyl groups, (Ci
C
6 ) alkoxy groups, halo (Cl-C,) alkoxy groups, (Cl-C) alkyl 25 thio groups, halo (C 1 -C.) alkylthio groups, (Ci-C,)alkyl sulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (C 1 C 6 )alkylsulfonyl groups, halo (Cl-CE)alkylsulfonyl groups, mono (C 1
-C
6 ) alkylamino groups, di (C 1
-C
6 ) alkylamino groups 26 whose (Cl-C)alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups; a phenylamino group; a substituted phenylamino group having on the ring one or more substituents which may be the same or different 5 and are selected from halogen atoms, cyano group, nitro group, (Cl-C6) alkyl groups, halo (C-C6) alkyl groups, (Ci C) alkoxy groups, halo (C-C.) alkoxy groups, (Cl-C) alkyl thio groups, halo (Cl-C 6 ) alkylthio groups, (Cl-C.) alkyl sulfinyl groups, halo (Cl-C.) alkylsulfinyl groups, (Cl 10 C6) alkylsulfonyl groups, halo (Cl-C.) alkylsulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di (Ci-C6) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (C-C 6 )alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more 15 substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C) alkyl groups, halo (C1-C) alkyl groups, (Ci C0) alkoxy groups, halo (C1-C6) alkoxy groups, (Cl-C,) alkyl thio groups, halo (CI-C 6 ) alkylthio groups, (C-C0 6 )alkyl 20 sulfinyl groups, halo (C 1 -C.) alkylsulfinyl groups, (C C,) alkylsulfonyl groups, halo (C-C) alkylsulfonyl groups, mono (C-C6) alkylamino groups, di (C-C6) alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups, 25 (3) in the case of A 5 being a (Cl-C 6 )alkylene group, a halo (Cl-C6) alkylene group, a (C2-C 6 )alkenylene group, a halo (C2-C) alkenylene group, a (C2-C 6 )alkynylene group or a halo (C 3
-C
6 ) alkynylene group, R" is a hydrogen 27 atom; a halogen atom; a (C 3 -C0) cycloalkyl group; a halo (C3-C6) cycloalkyl group; a (C-C6) alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same 5 or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C 6 ) alkyl groups, halo (C 1
-C
6 ) alkyl groups, (C-C) alkoxy groups, halo (C-C) alkoxy groups, (C-C) alkylthio groups, halo (C 1
-C
6 ) alkylthio groups, (Cl-C 6 ) alkylsulfinyl groups, halo (C-C6) alkylsulfinyl 10 groups, (C-C6) alkylsulfonyl groups, halo (C-C) alkyl sulfonyl groups, mono (Ci-C 6 )alkylamino groups, di(C, C6) alkylamino groups whose
(C-C
6 )alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group 15 having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C)alkyl groups, halo(C-C 6 )alkyl groups, (C-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C-C) alkylthio groups, halo (C1-C6) alkylthio groups, 20 (C-C6) alkylsulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C1-C) alkylsulfonyl groups, halo (C-C) alkyl sulfonyl groups, mono (CI-C) alkylamino groups, di(C 1 C) alkylamino groups whose (C-C)alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; or 25 -A'-R 7 (wherein A' is -0-, -S-, -SO- or -SO2-, and R 17 is a (C 3 -C) cycloalkyl group; a halo (C 3
-C
6 ) cycloalkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different 28 and are selected from halogen atoms, cyano group, nitro group, (Cl-CE) alkyl groups, halo (Cl-C) alkyl groups, (Cl C6) alkoxy groups, halo (C 1
-C
6 ) alkoxy groups, (C-C) alkyl thio groups, halo (C-C) alkylthio groups, (Cl-CE) alkyl 5 sulfinyl groups, halo (C-C) alkylsulfinyl groups, (Ci C,) alkylsulfonyl groups, halo (C 1 -C) alkylsulfonyl groups, mono (Cl-C6) alkylamino groups, di (Cl-CE) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; a heterocyclic group; 10 a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-CE) alkyl groups, halo (C-C6) alkyl groups,
(C
C6) alkoxy groups, halo (Cl-C) alkoxy groups, (Cl-C) alkyl 15 thio groups, halo (Ci-C 6 ) alkylthio groups, (Cl-C 6 )alkyl sulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Cl CE) alkylsulfonyl groups, halo (Cl-C6) alkylsulfonyl groups, mono (Cl-C) alkylamino groups, di (C-C6) alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, 20 and (C-C 6 )alkoxycarbonyl groups; or -A'-R" (wherein A is a (C-C 6 )alkylene group, a halo (Cl-C 6 ) alkylene group, a (C 2
-C
6 )alkenylene group, a halo (C 2
-C
6 ) alkenylene group, a (C2-CE) alkynylene group or a halo (C3-C) alkynylene group, and R is a hydrogen atom; a halogen atom; a (C3 25 C 6 )cycloalkyl group; a halo (C 3
-C
6 ) cycloalkyl group; a (Cl-C,) alkoxy group; a halo (Cl-C) alkoxy group; a (Cl C)alkylthio group; a halo (C-C) alkylthio group; a (C CE) alkylsulfinyl group; a halo (Cl-C) alkylsulfinyl group; 29 a (C 1
-C
6 ) alkylsulfonyl group; a halo (C 1
-C
6 ) alkylsulfonyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano 5 group, nitro group, (Cl-C 6 )alkyl groups, halo (C 1
-C
6 )alkyl groups, (Cl-C.) alkoxy groups, halo (Ci-C 6 ) alkoxy groups,
(C
1
-C
6 ) alkylthio groups, halo (C 1
-C
6 ) alkylthio groups,
(C
1
-C
6 ) alkylsulfinyl groups, halo (C 1
-C
6 ) alkylsulfinyl groups, (C 1
-C
6 ) alkylsulfonyl groups, halo (C 1
-C
6 ) alkyl 10 sulfonyl groups, mono (C,-C) alkylamino groups, di (C 1 C6)alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; a phenyloxy group; a substituted phenyloxy group having one or more substituents which may be the same or 15 different and are selected from halogen atoms, cyano group, nitro group, (C 1
-C
6 )alkyl groups, halo (C 1
-C
6 )alkyl groups, (Cl-C6) alkoxy groups, halo (Ci-C6) alkoxy groups, (C1-C6) alkylthio groups, halo (C 1
-C
6 ) alkylthio groups, (Cl-C6) alkylsulfinyl groups, halo (Cl-C6) alkylsulfinyl 20 groups, (C 1 -C,) alkylsulfonyl groups, halo (C 1
-C
6 ) alkyl sulfonyl groups, mono (Cl-C6) alkylamino groups, di (C 1 C6)alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; a phenylthio group; a substituted phenylthio group having 25 one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 )alkyl groups, halo (Ci-C 6 )alkyl groups, (Cl-C) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, 30 (C1-C6) alkylthio groups, halo (C 1
-C
6 ) alkylthio groups, (C-C6) alkylsulfinyl groups, halo (C-C) alkylsulfinyl groups, (C1-C) alkylsulfonyl groups, halo (C-C6) alkyl sulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di (Cl 5 C) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; a heterocyclic group; or a heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro 10 group, (C1-C) alkyl groups, halo (C1-C) alkyl groups,
(C
C0) alkoxy groups, halo (C-C) alkoxy groups, (C-C6) alkyl thio groups, halo (Cl-C 6 )alkylthio groups, (Cl-C 6 )alkyl sulfinyl groups, halo (C 1
-C
6 )alkylsulfinyl groups, (C1
C
6 )alkylsulfonyl groups, halo (C-C6) alkylsulfonyl groups, 15 mono (C 1 -C) alkylamino groups, di (Cl-C) alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (C,-C 6 )alkoxycarbonyl groups)), n is an integer of 0 to 4, further, two adjacent Xs on the aromatic ring 20 being able to be taken together to represent a fused ring that may have one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C 6 )alkyl groups, halo (C-C6) alkyl groups, (C-C6) alkoxy groups, halo (Ci 25 C 6 )alkoxy groups, (Cl-C 6 )alkylthio groups, halo(C C) alkylthio groups, (C1-C) alkylsulfinyl groups, halo (C-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups, halo (C-C6) alkylsulfonyl groups, mono (C- 31 C.) alkylamino groups, di (Ci-C) alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, and (Cl-C 6 ) alkoxycarbonyl groups, each of Ys, which may be the same or 5 different, is a halogen atom; a cyano group; a nitro group; a (C 3 -C,) cycloalkyl group; a halo (C 3 -C,) cycloalkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano 10 group, nitro group, (Cl-C 6 ) alkyl groups, halo (Cl-C.) alkyl groups, (Cl-C 6 ) alkoxy groups, halo (Cl-C.) alkoxy groups, (Cl-C.) alkylthio groups, halo (Cl-C.) alkylthio groups,
(C
1 -C) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Cl-C 6 ) alkylsulfonyl groups, halo (Cl-C 6 ) alkyl 15 sulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di(Cl
C
6 ) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (C,-C,)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same 20 or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 ) alkyl groups, halo (Cl-C.) alkyl groups, (C1-C6) alkoxy groups, halo (C-C) alkoxy groups, (Cl-C,) alkylthio groups, halo (Cl-C 6 ) alkylthio groups, (C-C6) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl 25 groups, (Cl-C 6 ) alkylsulfonyl groups, halo (Cl-C.) alkyl sulfonyl groups, mono (C-C) alkylamino groups, di (Ci C) alkylamino groups whose
(C-C
6 )alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; or 32 -A-R" (wherein A 5 and R" are as defined above), further, two adjacent Ys on the aromatic ring being able to be taken together to represent a fused ring that may have one or more substituents which may 5 be the same or different and are selected from halogen atoms; (C1-C) alkyl groups; halo (C1-C6) alkyl groups; (C C0) alkoxy groups; halo (C-c6) alkoxy groups; (C1-C) alkyl thio groups; halo (Ci-C) alkylthio groups; (C-C 6 )alkyl sulfinyl groups; halo (C1-C6) alkylsulfinyl groups; (C, 10 C)alkylsulfonyl groups; halo(C 1 -C)alkylsulfonyl groups; phenyl group; substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C1-C) alkyl groups, halo (C-C6) alkyl groups, (C1 15 C) alkoxy groups, halo (C1-C) alkoxy groups, (C-C6) alkyl thio groups, halo (C-C6) alkylthio groups, (C1-C6) alkyl sulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (Cl C6)alkylsulfonyl groups, halo (C-C6) alkylsulfonyl groups, mono (C1-C) alkylamino groups, di (C1-C) alkylamino groups 20 whose (C-C)alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; heterocyclic groups; and substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, 25 (C-C6) alkyl groups, halo (C1-C6) alkyl groups, (C1 C6) alkoxy groups, halo (C1-C6) alkoxy groups, (CI-C) alkyl thio groups, halo (Ci-C6) alkylthio groups, (C1-C6) alkyl sulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C,- 33
C
6 ) alkylsulfonyl groups, halo (C 1 -C.) alkylsulfonyl groups, mono (C 1 -C.) alkylamino groups, di (Cl-C,) alkylamino groups whose (C1-C 6 )alkyl groups may be the same or different, and (Cl-C 6 ) alkoxycarbonyl groups, 5 m is an integer of 1 to 5, and each of Z' and Z2 is an oxygen atom or a sulfur atom} or a salt thereof, an agricultural and horticultural chemical containing aromatic diamide derivative as an active ingredient, and a usage of the same. 10 MODE FOR CARRYING OUT THE INVENTION In the definition of the general formula (I) shown for the aromatic diamide derivative or salt thereof of the present invention, the term "halogen atom" means a chlorine atom, a bromine atom, an iodine 15 atom or a fluorine atom. The term " (Cl-C.) alkyl" means a linear or branched alkyl group of 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl or the like. The term "halo(C 1
-C
6 )alkyl" means a substi 20 tuted and linear or branched alkyl group of 1 to 6 carbon atoms having as the substituent(s) one or more halogen atoms which may be the same or different. The term " (C 1
-C
8 ) alkylene" means a linear or branched alkylene group of 1 to 8 carbon atoms, such as 25 methylene, ethylene, propylene, trimethylene, dimethyl methylene, tetramethylene, isobutylene, dimethyl ethylene, octamethylene or the like. As "the 5- to 8- 34 membered ring which R 5 and R 6 (or R 2 and A' or R1) form by their binding to each other, i.e., the 5- to 8 membered ring that may contain one or two (or one to three) atoms which may be the same or different and are 5 selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring" or "the 5- to 8-membered ring which R 5 (or R 6 or R') and R 4 form by their binding to each other, i.e., the 5- to 8-membered ring that may contain two or 10 three, or three or four atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring", there can be exemplified azetidine ring, pyrrolidine ring, pyrroline ring, 15 piperidine ring, imidazolidine ring, imidazoline ring, oxazolidine ring, thiazolidine ring, isoxazolidine ring, isothiazolidine ring, tetrahydropyridine ring, piperazine ring, morpholine ring, thiomorpholine ring, dioxazine ring, dithiazine ring, etc. 20 The "heterocyclic group" includes, for example, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydro pyranyl group, tetrahydrothiopyranyl group, oxazolyl 25 group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group and pyrazolyl group. The "fused ring" includes, for example, naphthalene, 35 tetrahydronaphthalene, indene, indane, quinoline, quinazoline, indole, indoline, chroman, isochroman, benzodioxane, benzodioxole, benzofuran, dihydrobenzo furan, benzothiophene, dihydrobenzothiophene, 5 benzoxazole, benzothiazole, benzimidazole and indazole. The salt of the aromatic diamide derivative of the general formula (I) of the present invention includes, for example, inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate and the 10 like; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and the like; salts with a sodium ion, potassium ion, calcium ion or the like. The aromatic diamide derivative of the 15 general formula (I) or salt thereof of the present invention contains one or more asymmetric carbon atoms or asymmetric centers in its structural formula in some cases and has two or more optical isomers and diastereomers in some cases. The present invention 20 also includes all of the individual optical isomers and mixtures consisting of these isomers in any ratio. The aromatic diamide derivative of the general formula (I) or salt thereof of the present invention has two geometrical isomers due to a carbon-carbon double bond 25 or a carbon-nitrogen double bond in its structural formula in some cases. The present invention also includes all of the individual geometrical isomers and mixtures consisting of these isomers in any ratio. The 36 present invention also includes hydrates of said compound, depending on the kind of the compound. Preferable examples of the aromatic diamide derivative of the general formula (I) or salt thereof 5 of the present invention are aromatic diamide deriva tives in which A' is a (Cl-C 4 )alkylene group, B is -0- or -N(R4)- (wherein R 4 is a hydrogen atom or a (C,-C 3 )alkyl group), R' is a hydrogen atom, a (Cl-C 3 )alkyl group, a phenyl(C-C 3 )alkyl group, a substituted phenyl (Cl 10 C 3 )alkyl group, a (Cl-C 3 )alkylcarbonyl group, a halo(Cl
C
3 )alkylcarbonyl group, a (C-C 3 )alkoxycarbonyl group, a mono (Cl-C 3 ) alkylaminocarbonyl group, a di (Cl-C 3 ) alkyl aminocarbonyl group whose (C-C 3 )alkyl groups may be the same or different, a (Cl-C)alkylsulfonyl group, a 15 mono (Ci-C 3 ) alkylaminosulfonyl group, a di (C1-C 3 ) alkyl aminosulfonyl group whose (C-C 3 )alkyl groups may be the same or different, a di(C-C 3 )alkoxyphosphono group whose (Cl-C 3 )alkyl groups may be the same or different, or a di (Cl-C 3 )alkoxythiophosphono group whose (Cl 20 C,)alkyl groups may be the same or different, each of R 2 and R 3 is a hydrogen atom or a (Cl-C 3 )alkyl group, each of Q1 through Q 4 is a carbon atom, X is a halogen atom, a nitro group, a halo (C1-C.) alkyl group, a halo(Cl C,)alkoxy group or a halo(C,-C6)alkylthio group, n is an 25 integer of 0 to 2, Q' is a carbon atom or a nitrogen atom, each of Ys, which may be the same or different, is a halogen atom, a (C-C 3 )alkyl group, a halo(C, C3) alkyl group, a (C-C 3 ) alkoxy group, a halo (C,- 37
C
3 ) alkoxy group, a halo (C1-C3) alkylthio group or a halo (Cl-C 3 ) alkoxyhalo (Cl-C3) alkoxy group, m is an integer of 1 to 3, each of Z' and Z 2 is an oxygen atom; or salts thereof. 5 The aromatic diamide derivative of the general formula (I) or salt thereof of the present invention can be produced, for example, by the production process illustrated below. In the present invention, the production can be carried out also by, 10 for example, the process disclosed in JP-A-11-240857. A process for the production, however, is not limited to these production processes.
38 Production process 1. Ym
KNH
2 Z5 Qii Q2Q Xn 0 Q3 Q 41 Z 2 1-B-R1
HN-R
2 zX Q 2 Q 1 m(V) Q )m Z 2 (IV) Z A!-B-R' 1 1 2 nQ N-R 2 Xn Q N
Z
2 H (I-1) 39 wherein R', R 2 , R 3 , A', B, Q' through Q 5 , X, n, Y, m, Z' and Z 2 are as defined above. An aromatic diamide derivative of the general formula (I-1) can be obtained by allowing an aromatic 5 carboxylic acid anhydride derivative of the general formula (II) to react with an aromatic amine of the general formula (III) in the presence of an inert solvent to obtain an aromatic imide derivative of the general formula (IV), and allowing said aromatic imide 10 derivative (IV) to react with an amine of the general formula (V) after or without isolation of the aromatic imide derivative (IV). (1). General formula (II) -> general formula (IV) As the inert solvent usable in this reaction, 15 any inert solvent may be used so long as it does not markedly inhibit the progress of the reaction. There can be exemplified inert solvents including aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, 20 chloroform, carbon tetrachloride, etc.; chlorinated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; acyclic or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, etc.; esters such as ethyl acetate, etc.; amides such as dimethyl 25 formamide, dimethylacetamide, etc.; acids such as acetic acid, etc.; dimethyl sulfoxide; 1,3-dimethyl-2 imdazolidinone; and the like. These inert solvents may be used singly or as a mixture thereof.
40 Since the reaction is an equimolar reaction, it is sufficient that the reactants are used in equimolar amounts, though either of them may be used in excess. If necessary, the reaction may be carried out 5 under dehydrating conditions. As to the reaction temperature, the reaction can be carried out at room temperature to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of 10 reaction, the reaction temperature, etc., it may be properly chosen in the range of several minutes to 48 hours. After completion of the reaction, the desired compound is isolated from the reaction system contain 15 ing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced. The desired compound can be subjected to the subsequent reaction step without isolation from the 20 reaction system. The aromatic carboxylic acid anhydride derivative of the general formula (II) can be produced by any of the processes described in J. Org. Chem., 52, 129 (1987), J. Am. Chem. Soc., 51, 1865 (1 to 29), 25 ditto 63, 1542 (1941), etc. The aromatic amine of the general formula (III) can be produced by any of the processes described in J. Org. Chem., 29, 1 (1964), Angew. Chem. Int. Ed. Engl., 24, 871 (1985), Synthesis, 41 1984, 667, Journal of Chemical Society of Japan, 1973, 2351, German Patent Laid-Open DE-2606982, JP-A-1-90163, etc. (2). General formula (IV) -+ general formula (I-1) 5 As an inert solvent usable in this reaction, those exemplified as the inert solvent usable in (1) can be exemplified. Since the reaction is an equimolar reaction, it is sufficient that the reactants are used in 10 equimolar amounts, though the amine of the general formula (V) may be used in excess. As to the reaction temperature, the reaction can be carried out at room temperature to the reflux temperature of the inert solvent used. Although the 15 reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in the range of several minutes to 48 hours. After completion of the reaction, the desired 20 compound is isolated from the reaction system contain ing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced.
42 Production process 2. 0 3m 1 A!-B-Rl NH X
HN-R
2 0 0 V) (III-i) (Ii O OH ,I B-Rl QOHQi ON-R 2 N OH 0 R Ym R 3 (IV-i) I BNH (VI-2) HN-R' 5
(R
3 -H) (V) (R 2 -H) Condensing Condensing Condensing Condensing agent agent agent agent Q 0 Q 1 N-Al-B-R Q4 m a (VII-1) Q(VII-2) Ym R 3 A-B-4 B-R-R -NH
HN-R
2 ___ 1 2 -B R Q21Q N-R2 (V) XnN (IT-i) 13 Q5 0
(I)
43 wherein R', R2, R 3 , A', B, Q' through Q 5 , X, n, Y, m, Z' and Z 2 are as defined above. An aromatic diamide derivative of the general formula (I) can be produced by allowing an aromatic 5 carboxylic acid anhydride derivative of the general formula (II-1) to react with an amine of the general formula (V) in the presence of an inert solvent to obtain a phthalamide of the general formula (VI-2), and treating this aromatic amide (VI-2) as follows after or 10 without isolation. When R 2 of the aromatic amide (VI-2) is a hydrogen atom, the aromatic amide (VI-2) is subjected to condensation reaction in the presence of a condensing agent to obtain a compound of the general formula (VII-2), which is allowed to react with an 15 aromatic amine of the general formula (III-1) in the presence of an inert solvent after or without isolation of the compound (VII-2). When R 2 of the aromatic amide (VI-2) is other than a hydrogen atom, the aromatic amide (VI-2) is condensed with an aromatic amine of the 20 general formula (III-1) in the presence of a condensing agent. Alternatively, an aromatic diamide derivative of the general formula (I) can be produced by allowing an aromatic carboxylic acid anhydride derivative of the 25 general formula (II-1) to react with an aromatic amine of the general formula (III-1) in the presence of an inert solvent to obtain an aromatic amide of the general formula (VI-1), and treating the aromatic amide 44 (VI-1) as follows after or without isolation. When R 3 of the aromatic amide (VI-1) is a hydrogen atom, the aromatic amide (VI-1) is subjected to condensation reaction in the presence of a condensing agent to 5 obtain a compound of the general formula (VII-1), which is allowed to react with an amine of the general formula (V) in the presence of an inert solvent after or without isolation of the compound (VII-1). When R 3 of the aromatic amide (VI-1) is other than a hydrogen 10 atom, the aromatic amide (VI-1) is condensed with an amine of the general formula (V) in the presence of a condensing agent. (1) General formula (II-1) -+ general formula (VI-1), or general formula (II-1) -+ general formula (VI 15 2) In the case of either of these reactions, the desired compound can be produced in a manner similar to that described in production process 1-(2). (2). General formula (VII-1) or general formula (VII 20 2) -+ general formula (I) In the case of this reaction, the desired compound can be produced in a manner similar to that described in production process 1-(2). (3). General formula (VI-1) -+ general formula (VII-1), 25 or general formula (VI-2) -> general formula (VII 2) In the case of either of these reactions, the desired compound can be produced according to the 45 process described in J. Med. Chem., 10, 982 (1967). (4). General formula (VI-1) or general formula (VI-2) -+ general formula (I) The desired compound can be produced by 5 allowing an aromatic amide derivative of the general formula (VI-1) or the general formula (VI-2) to react with an amine of the general formula (V) or the general formula (III-1), respectively, in the presence of a condensing agent and an inert solvent. If necessary, 10 the reaction can be carried out in the presence of a base. The inert solvent used in the reaction includes, for example, tetrahydrofuran, diethyl ether, dioxane, methylene chloride and chloroform. 15 As the condensing agent used in the reaction, any condensing agent used in conventional amide produc tion may be used. There can be exemplified Mukaiyama reagent (2-chloro-N-methylpyridinium iodide), DCC (1,3 dicyclohexylcarbodiimide), CDI (carbonyldiimidazole) 20 and DEPC (diethyl cyanophosphate). As to the amount of the condensing agent used, the condensing agent may be used in an amount properly chosen in the range of 1 mole to excess moles per mole of the aromatic amide derivative of the general formula (VI-1) or the general 25 formula (VI-2). The base usable in the reaction includes, for example, organic bases such as triethylamine, pyridine, etc., and inorganic bases such as potassium carbonate, 46 etc. As to the amount of the base used, the base may be used in an amount properly chosen in the range of 1 mole to excess moles per mole of the aromatic amide derivative of the general formula (VI-1) or the general 5 formula (VI-2). As to the reaction temperature, the reaction can be carried out at 0 0 C to the boiling point of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction 10 temperature, etc., it ranges from several minutes to 48 hours. After completion of the reaction, the desired compound is isolated from the reaction system contain ing the desired compound by a conventional method, and 15 if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced. Typical compounds as the aromatic diamide derivative of the general formula (I) or a salt thereof 20 are listed in Table 1 or Table 2 but they are not intended in any way to limit the scope of the present invention. In the following tables, Me indicates methyl, Et ethyl, Pro propyl, Bu butyl, Ph phenyl, Pyr pyridyl, and c- an alicyclic hydrocarbon.
47 o ALB-R 3 | N-R2 4 Xn 6 5 5 M N 4 6 O R3 2 3 Table 1 (Z 1
=Z
2 =0, R 3 =H, Q'~Q 5 =C, unless otherwise specified.) Physical No. -A -B-R R2 Xn Ym property: Melting point *C 1 (CH2 )NHCO 2 Pr-i H 3-I 2-Me-4-CF(CF 3 ) 2 105 2 (CH 2
)NHCO
2 Pr-i H 3-I 2-Me-4-OCF 3 200 3 (CH 2
)NHCO
2 Et H 3-I H 175 4 (CH2)NHCO 2 Et H 3-I 4-CF 2
CF
3 180 5 (CH 2
)NHCO
2 Me H 3-I H 200 6 (CH 2
)NHCO
2 Me H 3-I 2-Me-4-CF 2
CF
3 130 7 (CH 2
)NHCO
2 Me H 3-I 2-Me-4-CF(CF 3
)
2 160 8 C(Me) 2
CH
2
NHCO
2 Et H 3-1 2-Me-4-CF(CF 3
)
2 240 9 C(Me) 2
CH
2
NHCO
2 Et H 6-I 2-Me-4-CF(CF 3 ) 2 140 10 C(Me) 2
CH
2
NHCO
2 Et H 3-I 2-Me-4-OCF 3 155 11 C(Me) 2
CH
2
NHCO
2 Et H 6-I 2-Me-4-OCF 3 220 12 C(Me) 2
CH
2
NHCO
2 Me H 3-I 2-Me-4-CF(CF 3
)
2 100 13 C(Me) 2
CH
2
NHCO
2 Me H 6-I 2-Me-4-CF(CF 3 ) 2 230 14 C(Me) 2
CH
2
NHCO
2 Pr H 3-I 2-Me-4-CF(CF 3
)
2 100 15 C(Me) 2
CH
2
NHCO
2 Me H 3-I 2-Me-4-OCF 3 95 16 C(Me) 2
CH
2
NHCO
2 Me H 6-I 2-Me-4-OCF 3 120 17 C(Me) 2
CH
2
NHCO
2 Et H 3-I 2-Me 95 18 C(Me) 2
CH
2
NHCO
2 Et H 6-I 2-Me 120 48 Table 1 (Cont'd) Physical No. -AK-B-R R 2 Xn Ym property: Melting point 0 C 19 C(Me) 2
CH
2
NHCO
2 Et H 3-I 2-Me-4-CF 2
CF
3 200 20 (CH 2 ) 3
NHCO
2 Bu-t H 3-I 2-Me-4-CF (CF 3 ) 2 145 21 (CH2) 3
NHCO
2 Me H 3-I 2-Me-4-CF (CF 3 ) 2 80 22 CH (Me) CH 2
NHCO
2 Me H 3-I 2-Me-4-CF (CF 3 ) 2 175 23 Q H 3-I 2-Me-4-CF (CF 3 ) 2 235 24 Q H 6-I 2-Me-4-CF (CF 3 ) 2 225 25 Q H 3-I 2-Me-4-OCF 3 220 26 Q H 6-I H 225 27 C(Me) 2
CH
2 NHCOPh H 3-I 2-Me-4-CF(CF 3
)
2 240 28 C(Me) 2
CH
2 NHCOMe H 3-I 2-Me-4-CF(CF 3
)
2 125 29 C(Me) 2
CH
2 NHCOPr-c H 3-I 2-Me-4-CF(CF 3
)
2 230 30 C(Me) 2
CH
2 NHCOBu-t H 3-I 2-Me-4-CF(CF 3
)
2 160 31 (CH 2 ) 2 NHCOMe H 3-I 2-Me-4-CF (CF 3 ) 2 210 32 (CH2) 2 NHCOMe H 3-I 2-Me-4-OCF 3 210 33 CH (Me) CH 2 NHCOMe H 3-I 2-Me-4-CF (CF 3 ) 2 140 34 CH (Me) CH 2 NHCOEt H 3-I 2-Me-4-CF (CF 3 ) 2 230 35 C (Me) 2
CH
2 NHCOEt H 3-I 2-Me-4-CF (CF 3 ) 2 220 36 CH (Me) CH 2 NHCOMe H 3-I 2-Me-4-OCF 3 215 37 (CH 2 ) 2 NHCON (Me) 2 H 3-I 2-Me-4-CF (CF 3 ) 2 170 38 CH(Me)CH 2 NHCON(Me) 2 H 3-I 2-Me-4-CF(CF 3
)
2 250 39 CH (Me) CH 2
NHSO
2 Me H 3-I 2-Me-4-CF (CF 3 ) 2 110 40 CH (Me) CH 2
NHSO
2 Ph H 3-I 2-Me-4-CF (CF 3 ) 2 130 41 CH (Me) CH 2
NHSO
2 Et H 3-I 2-Me-4-CF (CF 3 ) 2 155 42 CH (Me) CH 2 N (Me) SO 2 Me H 3-I 2-Me-4-CF (CF 3 2 100 43 CH (Me) CH 2 N (Me) SO 2 Me H 3-I 2-Me-4-OCF 3 200 - Cont'd - 49 Table 1 (Cont'd) Physical No. -A -B-R R2 Xn Ym property: Melting point 0C 44 CH (Me) CH 2 N (Me) SO 2 Me H 3-I H 250 45 CH(Me)CH 2
NHSO
2 N(Me) 2 H 3-I 2-Me-4-CF(CF 3
)
2 95 46 (CH2) 3 N(Me) 2 H 3-I 2-Me-4-CF(CF 3
)
2 155 47 (CH 2 ) 3 N(Me) 2 H 3-I 2-Me-4-OCF 3 115 48 CH(Me)CH 2 NH- H 3-I 2-Me-4-CF(CF 3 ) 2 175 P(=S) (OMe) 2 49 CH(Me)CH 2 NH- H 3-I 2-Me-4-OCF 3 125 P(=S) (OMe) 2 50 CH(Me)CH 2 NH- H 3-I 2-Me-4-CF(CF 3 ) 2 180 P(=S) (OEt) 2 51 CH 2 -(2,2-Me 2 -1,3- H 3-I 2-Me-4-CF(CF 3 ) 2 170 Dioxolan-4-yl) 52 CH 2 - (2, 2-Me 2 -1, 3- H 3-I 2-Me-4-OCF 3 165 Dioxolan-4-yl) 53 CH 2 -(tetrahydropyran- H 3-I 2-Me-4-OCF 3 176 4-yl) 54 CH 2 -(tetrahydropyran- H 3-I 2-Me-4-CF(CF 3 ) 2 145 4-yl) 55 CH 2 0Me Et 3-Cl 2-Me-4-CF(CF 3
)
2 136 56 CH(Me)CH 2 0Me H 3-I 2-Me-4-CF(CF 3 ) 2 136 57 CH(Me)CH 2 0Me H 3-I 2-Me-4-OCF 3 137 58 CH(Me)CH 2 OH H 3-Cl 2-Me-4-CF(CF3) 2 200 59 CH(Me) (CH2) 20Me H 3-I 2-Me-4-CF(CF 3 ) 2 164 60 C(Me) 2
CH
2 OH H 3-I 2-Me-4-CF(CF 3 ) 2 210 61 C[-(CH 2 ) 4
-ICH
2 OH H 3-I 2-Me-4-CF(CF 3 ) 2 207 - Cont'd - 50 Table 1 (Cont'd) Physical No. -A -B-R R 2 Xn Ym property: Melting point 0 C 62 CH(Me) (CH 2 ) 2 0CH 2
CF
3 H 3-I 2-Me-4-CF (CF3) 2 191 63 CH(Me) (CH 2 )20Et H 3-I 2-Me-4-CF(CF3)2 100 64 CH(Me) (CH2) 2OEt H 3-I 2-Me-4-OCF3 164 65 CH (Me) (CH 2 ) 2 0Et H 3-I 2-Cl-4-OCF 3 151 66 CH(Me) (CH 2
)
2 0- H 3-I 2-Me-4-CF(CF3)2 71
(CH
2 ) 2 0Me 67 CH (Me) CH 2 0Et H 3-I 2-Me-4-CF (CF3) 2 171 68 CH (Me) CH 2 0CH 2 Ph H 3-I 2-Me-4-CF (CF3) 2 186 69 CH (Me) CH 2 OPr H 3-I 2-Me-4-CF (CF3) 2 160 70 CH (Me) (CH 2 ) 20Pr H 3-I 2-Me-4-CF (CF3) 2 146 71 CH (Me) CH 2 0 (CH 2 ) 20Me H 3-I 2-Me-4-CF (CF3) 2 153 72 CH (Me) CH 2 OBu-i H 3-I 2-Me-4-CF (CF3) 2 188 73 CH (Me) CH 2 0Bu-i H 3-I 2-OPh 113 74 CH (Me) (CH 2 ) 2 0Bu-i H 3-I 2-Me-4-CF (CF3) 2 158 75 CH (Me) (CH 2
)
2 0BU-i H 3-I 4-Cl 204 76 CH (Me) CH 2 0 (CH 2 ) 2SMe H 3-I 2-Me-4-CF (CF3) 2 168 77 CH (Me) CH 2 0 (CH 2 ) 2 SEt H 3-I 2-Me-4-CF (CF3) 2 140 78 CH (Me) CH 2 0Ph H 3-I 2-Me-4-CF (CF3) 2 110 79 CH (Me) CH 2 OPh H 3-I H 130 80 CH (Me) CH 2 0Ph H H 2-Me-4-CF(CF3)2 Amorphous 81 CH (Me) CH 2 0 (4-Cl-Ph) H 3-I 2-Me-4-CF (CF3) 2 200 82 CH (Me) CH 2 0 (4-Cl-Ph) H 3-I 2, 4, 6- (Me) 3 220 83 CH (Me) CH 2 0 (3-CF3-Ph) H 3-I 2-Me-4-CF (CF3) 2 100 84 CH (Me) CH 2 0 (3-CF3-Ph) H 3-I 2-Me-4-OCF3 140 85 CH (Me) CH 2 0COMe H 3-I 2-Me-4-CF (CF3) 2 110 - Cont'd - 51 Table 1 (Cont'd) Physical No. -A'-B-R R2 Xn Ym property: Melting point *C 86 CH (Me) CH 2 0COMe H 3-I 2-Me-4-OCF 3 155 87 C(Me) 2
CH
2 0COMe H 3-I 2-Me-4-CF(CF 3
)
2 180 88 CH (Me) CH 2 OCON (Me) 2 H 3-I 2-Me-4-CF (CF 3 ) 2 100 89 CH (Me) CH 2 0CON (Me) 2 H 3-I 2-Me-4-OCF 3 140 90 CH (Me) CH 2 0CON (Et) 2 H 3-I 2-Me-4-CF (CF 3 ) 2 190 91 C (Me) 2
CH
2 0CON (Me) 2 H 3-I 2-Me-4-CF (CF 3 ) 2 115 92 C(Me) 2
CH
2 0CON(Me) 2 H 3-I 2-Me-4-OCF 3 150 93 CH(Me)CH 2 0CON(Pr-i) 2 H 3-I 2-Me-4-CF(CF 3
)
2 100 94 CH (Me) CH 2 0CON (Me) Ph H 3-I 2-Me-4-CF (CF 3 ) 2 105 95 CH(Me)CH 2 0CO- H 3-I 2-Me-4-CF(CF 3
)
2 255 N (-CH 2
CH
2 0CH 2
CH
2 -) 96 CH (Me) CH 2 0CONHEt H 3-I 2-Me-4-CF (CF 3 ) 2 185 97 CH (Me) CH 2 0CONHEt H 3-I 2-Me-4-OCF 3 220 98 CH (Me) CH 2 0CO- H 3-I 2-Me-4-CF (CF 3 ) 2 Amorphous N (-CH 2
CH
2
CH
2
CH
2 -) 99 CH (Me) CH 2 0CONHPr-i H 3-I 2-Me-4-CF (CF 3 ) 2 130 100 C (Me) 2
CH
2 0CONHEt H 3-I 2-Me-4-CF (CF 3 ) 2 225 101 CH (Me) CH 2 OCONHMe H 3-I 2-Me-4-CF (CF 3 ) 2 190 102 CH (Me) CH 2 0CONHMe H 3-I 2-Me-4-OCF 3 200 103 CH (Me) CH 2 0CONHPr H 3-I 2-Me-4-CF (CF 3 ) 2 175 104 CH (Me) CH 2 0CONHPr H 3-I 2-Me-4-OCF 3 205 105 CH (Me) CH 2 0CONHPr-i H 3-I 2-Me-4-CF (CF 3 ) 2 170 106 CH (Me) CH 2 0CONHPr-i H 3-I 2-Me-4-OCF 3 215 107 CH (Me) CH 2 0CONHCH 2 Ph H 3-I 2-Me-4-CF (CF 3 ) 2 175 108 CH (Me) CH 2 0CONHCH 2 Ph H 3-I 2-Me-4-OCF 3 190 - Cont'd - 52 Table 1 (Cont'd) Physical No. -A -B-R R Xn Ym property: Melting point *C 109 CH(Me)CH 2 0CONHPh H 3-I 2-Me-4-CF(CF 3 ) 2 190 110 CH (Me) CH 2 0CONHPh H 3-I 2-Me-4-OCF 3 230 111 CH(Me)CH 2 0- H 3-I 2-Me-4-CF(CF 3 ) 2 115 P(=S) (OMe) 2 112 CH(Me)CH 2 0- H 3-I 2-Me-4-CF(CF 3 ) 2 140 P(=S) (OEt) 2 113 CH(Me)CH 2 0- H 3-I 2-Me-4-OCF 3 115 P(=S) (OEt) 2 114 CH(Me)CH 2 0- H 3-I H 125 P(=S) (OEt) 2 115 CH(Me)CH 2 0- H 3-I 2-Me 95 P(=S) (OEt) 2 116 C(Me) 2
CH
2 0- H 3-I 2-Me-4-CF(CF 3
)
2 120 P(=S) (OMe) 2 117 CH(Me)CH 2 0- H 3-I 2-Me-4-CF(CF 3
)
2 Amorphous P(=O) (OEt) 2 118 CH(Me)CH 2 0- H 3-I H Amorphous P(=O) (OEt) 2 - Cont'd Note: In the table, Q denotes the following group: -CH
NCO
2 Et mw 53 Table 1 (Cont'd) Physical No. -A-B-R R 2 Xn Ym property: Melting point *C 119 CH (Me) CH 2 0COCF 3 H 3-NO 2 2-Me-4-CF(CF 3 ) 2 209 120 C(Me) 2
CH
2 0COCF 3 H 3-I 2-Me-4-CF(CF 3
)
2 190 121 C(Me) 2
CH
2 0COCF 3 H 3-I 2-Cl-4-CF(CF 3 ) 2 150 122 C(Me) 2
CH
2 0COCF 3 H 6-I 2-Cl-4-CF(CF 3
)
2 95 123 CH(Me)CH 2 0CO-Ph H 3-I 2-Me-4-CF(CF 3 ) 2 124 C(Me) 2
CH
2 0CO-Ph H 3-I 2-Me-4-CF(CF 3
)
2 125 CH(Me)CH 2 0CO- (3-Pyr) H 3-I 2-Me-4-CF(CF 3 ) 2 126 C(Me) 2
CH
2 0CO-(3-Pyr) H 3-I 2-Me-4-CF(CF 3
)
2 127 (CH 2 ) 20CONHEt Me H 2-Me-4-CF 2
CF
3 52 128 (CH2) 2 0CONHEt Me H 2-Me-4-CF(CF 3 ) 2 113 129 C(Me) 2
CH
2 0CONHPr-n H 3-I 2-Me-4-CF(CF 3 ) 2 220 130 C(Me) 2
CH
2 0CONHPr-n H 3-I 2-Cl-4-CF(CF 3
)
2 200 131 CH(Me)CH 2 0CONHPr-i H 3-I 2-Me-4-CF(CF 3 ) 2 132 C(Me) 2
CH
2 0CONHPr-i H 3-I 2-Me-4-CF(CF 3
)
2 133 CH(Me)CH 2 OCONHPr-c H 3-I 2-Me-4-CF(CF 3 ) 2 114 134 CH(Me)CH 2 OCONHPr-c H 3-I 2-Me-4-OCF 3 212 135 C(Me) 2
CH
2 0CONHPr-c H H 2-Me-4-CF(CF 3 ) 2 176 136 C(Me) 2
CH
2 0CONHPr-c H 3-I 2-Me-4-CF(CF 3
)
2 231 137 C(Me) 2
CH
2 0CONHBu-n H 3-I 2-Me-4-CF(CF 3 ) 2 138 C(Me) 2
CH
2 0CONHBu-s H 3-I 2-Me-4-CF(CF 3
)
2 139 CH(Me)CH 2 OCONHBu-t H 3-I 2-Me-4-CF(CF 3 ) 2 215 140 CH(Me)CH 2 OCONHBu-t H 3-I 2-Cl-4-CF(CF 3 ) 2 190 - Cont'd - Iw 54 Table 1 (Cont'd) Physical No. -A -B-R R2 Xn Ym property: Melting point 'C 141 C(Me) 2
CH
2 0CONHBu-c H 3-I 2-Me-4-CF(CF 3
)
2 142 CH (Me) CH 2 0CONH- H 3-I 2-Me-4-CF (CF 3 ) 2 189
CH
2
C=CH
2 143 C(Me) 2
CH
2 0CONH- H H 2-Me-4-CF (CF 3 ) 2 174 . CH 2
C=CH
2 144 C(Me) 2
CH
2 0CONH- H 3-I 2-Me-4-CF (CF 3 ) 2 181
CH
2
C=CH
2 145 C (Me) 2
CH
2 0CONH- H 3-I 2-Me-4-OCF 3 196
CH
2
C=CH
2 146 CH(Me)CH 2 0CONH- H 3-I 2-Me-4-CF (CF 3 ) 2
CH
2 C=-CH 147 C(Me) 2
CH
2 0CONH- H 3-I 2-Me-4-OCF 3
CH
2 CECH 148 CH (Me) CH 2 0CONHCH 2
CF
3 H 3-I 2-Me-4-CF (CF 3 ) 2 124 149 C(Me) 2
CH
2 0CONHCH 2
CF
3 H 3-I 2-Me-4-CF(CF 3
)
2 196 150 C(Me) 2
CH
2 0CONHCH 2 - H 3-I 2-Me-4-CF(CF 3
)
2 COOMe 151 C(Me) 2
CH
2 0CONHCH 2 - H 3-I 2-Me-4-CF(CF 3
)
2 CON(Et) 2 152 C(Me) 2
CH
2 0CONHCH 2 -Ph H 3-I 2-Me-4-CF(CF 3
)
2 170 153 C(Me) 2
CH
2 0CONHCH 2 -Ph H 3-I 2-Cl-4-CF(CF 3
)
2 185 - Cont'd - 55 Table 1 (Cont'd) Physical No. -A 1-B-R R2 Xn Ym property: Melting point *C 154 CH (Me) CH 2 0CON (CH 3 ) - H 3-I 2-Me-4-CF(CF 3
)
2 Paste
CH
2 -Ph 155 CH (Me) CH 2
OCONHCH
2 - H 3-I 2-Me-4-CF(CF 3
)
2 (2-Cl-Ph) 156 CH(Me)CH 2 0CONHCH 2 - H 3-I 2-Me-4-CF(CF 3
)
2 (3-Cl-Ph) 157 CH (Me) CH 2 0CONHCH 2 - H 3-I 2-Me-4-CF(CF 3
)
2 181 (4-Cl-Ph) 158 CH (Me) CH 2 0CONHCH 2 - H 3-I 2-Me-4-CF(CF 3
)
2 170 (2-Me-Ph) 159 CH(Me)CH 2 0CONHCH 2 - H 3-I 2-Me-4-CF(CF 3
)
2 188 (4-Me-Ph) 160 CH(Me)CH 2 0CONHCH 2 - H 3-I 2-Me-4-CF(CF3) 2 (2-OMe-Ph) 161 CH (Me) CH 2 0CONHCH 2 - H 3-I 2-Me-4-CF(CF 3
)
2 178 (4-OMe-Ph) 162 CH (Me) CH 2 0CONHCH 2 - H 3-I 2-Me-4-CF(CF 3
)
2 186 (4-CF 3 -Ph) 163 CH (Me) CH 2 0CONHCH 2 - H 3-I 2-Me-4-CF(CF 3
)
2 (2-Pyr) 164 CH (Me) CH 2
OCONHCH
2 - H 3-I 2-Me-4-CF(CF 3
)
2 [2- (3-Cl-5-CF 3 -Pyr) ] - Cont' d - 56 Table 1 (Cont'd) Physical No. -A -B-R R2 Xn Ym property: Melting point 0 C 165 CH (Me) CH 2 0CONHCH 2 - H 3-I 2-Me-4-CF(CF 3
)
2 84 (3-Pyr) 166 CH(Me)CH 2 0CONHCH 2 - H 3-I 2-Me-4-CF(CF 3
)
2 [3-(6-Cl-Pyr)] 167 CH (Me) CH 2 0CONHCH 2 - H H 2-Me-4-CF (CF 3 ) 2 137 (4-Pyr) 168 CH (Me) CH 2 0CONHCH 2 - H 3-I 2-Me-4-CF (CF 3 ) 2 140 (4-Pyr) 169 CH(Me)CH 2 0CONHCH 2 [5- H 3-I 2-Me-4-CF (CF 3 ) 2 169
CF
3 -1, 3, 4-Triadiazol -2-yl] 170 CH(Me)CH 2
OCONH(CH
2
)
2 H 3-I 2-Me-4-CF (CF 3 ) 2 Paste -OMe 171 CH (Me) CH 2 0CONH (CH 2 ) 2 H 3-I 2-Me-4-OCF 3 231 -OMe 172 C(Me) 2
CH
2 0CONH(CH 2
)
2 H 3-I 2-Me-4-CF(CF 3
)
2 184 -OMe 173 C(Me) 2
CH
2 0CONH(CH 2
)
2 H 3-I 2-Me-4-OCF 3 135 -OMe 174 CH(Me)CH 2 0CONH(CH 2
)
3 H 3-I 2-Me-4-CF (CF 3 ) 2 -OMe - Cont'd mw 57 Table 1 (Cont'd) Physical No. -A -B-R R2 Xn Ym property: Melting point 0 C 175 C(Me) 2
CH
2 OCONH(CH2) 3 H 3-I 2-Me-4-OCF 3 -OMe 176 CH(Me)CH 2
OCONH(CH
2
)
2 H 3-I 2-Me-4-CF(CF 3
)
2 -SMe 177 CH(Me)CH 2 0CONH(CH 2 )2 H 3-I 2-Me-4-OCF 3 -SMe 178 C(Me) 2
CH
2 0CONH(CH2) 2 H 3-I 2-Me-4-CF(CF 3
)
2 -SMe 179 C(Me) 2
CH
2 0CONH(CH 2
)
2 H 3-I 2-Me-4-OCF 3 -SMe 180 CH(Me)CH 2 0CONH(CH 2
)
2 H 3-I 2-Me-4-CF(CF 3
)
2 -SOMe 181 CH (Me) CH 2 0CONH (CH 2 ) 2 H 3-I 2-Me-4-OCF 3 -SOMe 182 CH (Me) CH 2 0CONH (CH 2 ) 3 H 3-I 2-Me-4-CF(CF 3
)
2 171 -SMe 183 CH(Me)CH 2 0CONH(CH 2
)
3 H 3-I 2-Me-4-OCF 3 176 -SMe 184 C(Me) 2
CH
2 0CONH(CH2) 3 H 3-I 2-Me-4-CF(CF 3
)
2 95 -SMe 185 C(Me) 2
CH
2 0CONH(CH 2
)
3 H 3-I 2-Me-4-OCHF 2 178 -SMe - Cont' d - 58 Table 1 (Cont'd) Physical No. -AR-B-R R 2 Xn Ym property: Melting point 'C 186 C(Me) 2
CH
2 0CONH(CH 2
)
3 H 3-I 2-Me-4-CF(CF 3
)
2
-SO
2 Me 187 C (Me) 2
CH
2 0CONH (CH2) 3 H 3-I 2-Me-4-OCF 3
-SO
2 Me 188 CH (Me) CH 2 0C (=S) NHEt H 3-I 2-Me-4-CF (CF 3 ) 2 189 C(Me) 2
CH
2 0C(=S)NHEt H 3-I 2-Me-4-CF(CF 3
)
2 190 CH (Me) CH 2 OP (=S) - H 3-I 2-Me-4-OCF 3 (OMe) 2 191 CH (Me) CH 2 0P (=S) - H H 2-Me-4-OCF 3 (OMe)2 192 (CH2 30CONHEt H 3-I 2-Me-4-CF (CF 3 ) 2 193 (CH2) 30CONHEt H 3-I 2-Me-4-OCF 3 194 CH(Me) (CH 2 )20CONHEt H 3-I 2-Me-4-CF(CF 3
)
2 166 195 CH(Me) (CH 2
)
2 0CO- H 3-I 2-Me-4-CF(CF 3
)
2 N(Et)2 196 CH(Me) (CH2)20CONH- H 3-I 2-Me-4-CF(CF 3
)
2
CH
2 -Ph 197 C (Me) 2 (CH 2 ) 20CONHMe H 3-I 2-Me-4-CF (CF 3 ) 2 198 (CH 2 ) 40CONHEt H 3-I 2-Me-4-CF (CF 3 ) 2 76 199 (CH2) 40CONHPr-i H 3-I 2-Me-4-CF (CF 3 ) 2 132 200 CH (Me) (CH 2 ) 30CONHEt H 3-I 2-Me-4-CF (CF 3 ) 2 - Cont' d - 59 Table 1 (Cont'd) Physical No. -A -B-R R2 Xn Ym property: Melting point *C 201 CH (Me) (CH2) 30CO- H 3-I 2-Me-4-CF (CF 3 ) 2 N(Et) 2 202 CH (Me) (CH 2
)
3 0CONH- H 3-I 2-Me-4-CF(CF 3
)
2
CH
2 -Ph 203 C(Me) 2
(CH
2 )30CONHMe H 3-I 2-Me-4-CF(CF 3
)
2 204 (CH 2 ) 5 OCONHEt H H 2-Me-4-CF 2
CF
3 138 205 (CH 2 ) 5 OCONHEt H H 2-Me-4-CF (CF 3 ) 2 136 206 CH (Me) (CH2) 40CONHEt H 3-I 2-Me-4-CF (CF 3 ) 2 207 CH (Me) (CH2) 40CO- H 3-I 2-Me-4-CF(CF 3
)
2 N(Et)2 208 CH (Me) (CH 2 ) 40CONH- H 3-I 2-Me-4-CF(CF 3
)
2
CH
2 -Ph 209 C (Me) 2 (CH 2 ) 4 0CONHMe H 3-I 2-Me-4-CF (CF 3 ) 2 210 CH (Me) CH 2 OCONHEt H 3-F 2-Me-4-CF (CF 3 ) 2 178 211 CH (Me) CH 2 0CONHEt H 3-F 2-Me-4-OCF 3 179 212 CH (Me) CH 2 0CONHCH 2 -Ph H 3-F 2-Me-4-CF (CF 3 ) 2 131 213 C(Me) 2
CH
2 0CONHMe H 3-F 2-Me-4-CF(CF 3
)
2 214 CH (Me) CH 2 0CONHEt H 3-Cl 2-Me-4-CF (CF 3 ) 2 99 215 CH (Me) CH 2 OCONHEt H 3-Cl 2-Me-4-CF 2
CF
3 145 216 CH (Me) CH 2 0CONHEt H 3-Cl 2-Me-4-OCHF 2 188 217 CH (Me) CH 2 0CONHEt H 3-Cl 2-Me-4-OCF 3 218 CH (Me) CH 2
OCONHCH
2 -Ph H 3-Cl 2-Me-4-CF (CF 3 ) 2 - Cont'd - 60 Table 1 (Cont'd) Physical No. -A -B-R R2 Xn Ym property: Melting point 0C 219 C(Me) 2
CH
2 0CONHMe H 3-Cl 2-Me-4-CF(CF 3
)
2 220 CH(Me)CH 2 0CONHEt H 4-Cl 2-Me-4-CF(CF 3 ) 2 221 CH(Me)CH 2 0CONHEt H 4-Cl 2-Me-4-OCF 3 222 CH(Me)CH 2 0CONHEt H 3-Br 2-Me-4-CF(CF 3 ) 2 164 223 CH(Me)CH 2 0CONHEt H 3-Br 2-Me-4-OCF 3 196 224 CH(Me)CH 2
OCONHCH
2 -Ph H 3-Br 2-Me-4-CF(CF 3 ) 2 225 C(Me) 2
CH
2 0CONHMe H 3-Br 2-Me-4-CF(CF 3
)
2 226 CH(Me)CH 2 0CONHEt H 4-I 2-Me-4-CF(CF 3 ) 2 227 CH(Me)CH 2 0CONHEt H 4-I 2-Me-4-OCF 3 228 CH(Me)CH 2 0CONHEt H 3,4- 2-Me-4-CF(CF 3 ) 2 Cl2 229 CH(Me)CH 2 0CONHCH 2 -Ph H 3,4- 2-Me-4-CF(CF 3 ) 2 139 C12 230 CH(Me)CH 2 OCONHEt H 3,4- 2-Me-4-OCF 3 193 C12 231 CH(Me)CH 2 OCONHEt H 3-Br 2-Me-4-CF(CF 3 ) 2 -4-Cl 232 CH(Me)CH 2 0CONHEt H 3,4- 2-Me-4-CF(CF 3 ) 2 Br 2 233 CH(Me)CH 2 OCONHEt H 3-I- 2-Me-4-CF(CF 3 ) 2 4-Cl - Cont'd - 61 Table 1 (Cont'd) Physical No. -A -B-R R2 Xn Ym property: Melting point 0C 234 CH (Me) CH 2 0CONHEt H 3, 4-12 2-Me-4-CF (CF 3 ) 2 235 CH (Me) CH 2 OCONHEt H 3-NO 2 2-Me-4-CF (CF 3 ) 2 194 236 CH (Me) CH 2 0CONHCH 2 -Ph H 3-NO 2 2-Me-4-OCF 3 151 237 CH(Me)CH 2 0CON(Et) 2 H 3-NO 2 2-Me-4-CF(CF 3
)
2 238 C(Me) 2
CH
2 0CONHMe H 3-NO 2 2-Me-4-CF(CF 3
)
2 239 CH (Me) CH 2 0CONHEt H 3-CF 3 2-Me-4-CF (CF 3 ) 2 240 CH (Me) CH 2 0CONHCH 2 -Ph H 3-CF 3 2-Me-4-OCF 3 241 CH(Me)CH 2 0CON(Et) 2 H 3-CF 3 2-Me-4-CF(CF 3
)
2 178 242 C(Me) 2
CH
2 0CONHMe H 3-CF 3 2-Me-4-OCF 3 243 CH (Me) CH 2 0CONHEt H 4-CF 3 2-Me-4-CF (CF 3 ) 2 203 244 CH (Me) CH 2 0CONHEt H 3-OCF 3 2-Me-4-OCF 3 245 CH (Me) CH 2 0CONHCH 2 -Ph H 3-OCF 3 2-Me-4-CF (CF 3 ) 2 246 CH(Me)CH 2 0CON(Et) 2 H 3-OCF 3 2-Me-4-OCF 3 247 C (Me) 2
CH
2 0CONHMe H 3-OCF 3 2-Me-4-CF (CF 3 ) 2 182 248 CH(Me)CH 2 0CONHEt H 3-SMe 2-Me-4-CF(CF 3
)
2 249 CH (Me) CH 2 0CONHEt H 3-SOMe 2-Me-4-CF (CF 3 ) 2 250 CH(Me)CH 2 0CONHEt H 3- 2-Me-4-CF(CF 3
)
2
SO
2 Me 251 CH(Me)CH 2 0CONHEt H 3-SCF 3 2-Me-4-CF(CF 3
)
2 252 CH (Me) CH 2 0CONHEt H 3- 2-Me-4-CF (CF 3 ) 2
SOCF
3 - Cont'd - 62 Table 1 (Cont'd) Physical No. -A -B-R R2 Xn Ym property: Melting point *C 253 CH(Me)CH 2 0CONHEt H 3- 2-Me-4-CF(CF 3
)
2
SO
2
CF
3 254 CH(Me)CH 2 OCONHEt H 3- 2-Me-4-CF (CF 3 ) 2 C =CH 255 CH(Me)CH 2 0CONHEt H 3-C=- 2-Me-4-OCF 3 C-Bu-t 256 CH(Me)CH 2 0CONHEt H 3-Ce 2-Me-4-CF (CF 3 ) 2 C-Ph 257 CH(Me)CH 2 0CONHEt H 3-C= 2-Me-4-OCF 3
C-CF
3 258 CH(Me)CH 2 OCONHEt H 3-Ce 2-Me-4-CF (CF 3 ) 2 C-Si (Me) 259 CH(Me)CH 2 0CONHEt H 3-CH= 2-Me-4-CF (CF 3 ) 2 207 CH-CH= CH-4 260 CH(Me)CH 2 OCONHEt H 3-CH= 2-Me-4-OCF 3 185 CH-CH= CH-4 261 CH(Me)CH 2 OCONHEt H 3-OCF 2 2-Me-4-CF (CF 3 ) 2 -0-4 - Cont' d - 63 Table 1 (Cont'd) Physical No. -A -B-R R2 Xn Ym property: Melting point 0 C 262 CH(Me)CH 2 0CONHEt H 3-OCF 2 2-Me-4-CF (CF 3 ) 2
-CF
2 0 4 263 CH(Me)CH 2 0CONHEt H 3-I 2-Me-4-Cl 202 264 CH (Me) CH 2 OCONHEt H 3-I 2-Me-4-Cl Paste
(R
3 =Me) 265 CH (Me) CH 2 OCONHEt H 3-I 2-Me-4-CF 3 217 266 CH (Me) CH 2 0CONHEt H 3-I 2-Cl-4-CF 3 208 267 CH (Me) CH 2 OCONHEt H 3-I 2-Me-4-CF 2
CF
3 163 268 CH (Me) CH 2 0CONHCH 2 -Ph H 3-I 2-Me-4-CF 2
CF
3 168 269 CH (Me) CH 2 0CONHEt H 3-I 2-Et-4-CF 2
CF
3 179 270 CH (Me) CH 2 OCONHEt H 3-I 2-F-4-CF 2
CF
3 176 271 CH (Me) CH 2 0CONHEt H 3-I 2-Cl-4-CF 2
CF
3 184 272 CH (Me) CH 2 0CONHEt H 3-I 2-Me-4-C 3
F
7 -n 173 273 CH (Me) CH 2 0CONHEt H 3-I 2-Me-4-C 4
F
9 -n 274 C(Me) 2
CH
2 0CONHMe H 3-I 2-Cl-4-CF(CF 3
)
2 140 275 CH (Me) CH 2 OCONHEt H 3-I 2-OMe-4-CF (CF 3 ) 2 168 276 CH (Me) CH 2 0CONHEt H 3-I 2-Me-4-CF (CF 3 ) CF 2
CF
3 277 CH (Me) CH 2 OCONHEt H 3-I 2-Me-3-F-4 CF (CF 3 ) 2 - Cont' d - 64 Table 1 (Cont'd) Physical No. -A -B-R R2 Xn Ym property: Melting point 0C 278 CH(Me)CH 2 0CONHEt H 3-I 2-Me-3-OMe-4- 139
CF(CF
3 ) 2 279 CH(Me)CH 2 0CONHEt H 3-I 2-Me-4-C(CF 3 ) 2 - 193 OEt 280 CH(Me)CH 2 0CONHEt H 3-I 2-Br-4-OCF 3 189 281 CH(Me)CH 2 OCONHEt H 3-I 2-Cl-4-OCF 3 282 CH(Me)CH 2 0CONHEt H 3-I 2-Me-4-OCF 2
CF
3 283 CH(Me)CH 2 0CONHEt H 3-I 2-Me-4-OC 3
F
7 -n 284 CH(Me)CH 2 0CONHEt H 3-I 2-Me-4-OCHF 2 185 285 CH(Me)CH 2 0CONHCH 2 -Ph H H 2-Me-4-OCF 2
CHF
2 141 286 CH(Me)CH 2 OCONHEt H 3-I 2-Me-4-OCF 2 CHC1F 193 287 CH(Me)CH 2 0CONHEt H 3-I 2-Me-4-OCF 2 CHF- 182
CF
3 288 CH(Me)CH 2 0CONHEt H 3-I 2-Me-4-OCF 2 CHF- 168
OCF
3 289 CH(Me)CH 2 0CONHEt H 3-I 2-Me-4-0-(3-Cl-5 200
-CF
3 -Pyr-2-yl) 290 CH(Me)CH 2 0CONHEt H 3-I 2-Me-4-SCF 3 203 291 CH(Me)CH 2 0CONHEt H 3-I 2-Me-4-SOCF 3 292 CH(Me)CH 2 0CONHEt H 3-I 2-Me-4-SO 2
CF
3 293 CH(Me)CH 2 0CONHCH 2 -Ph H H 3-OCF 2 0-4 142 294 CH(Me)CH 2 0CONHEt H 3-I 3-OCF 2 0-4 - Cont'd - 65 Table 1 (Cont'd) Physical No. -A -B-R R2 Xn Ym property: Melting point 0 C 295 CH (Me) CH 2 0CONHEt H 3-I 2-Me-3-OCF 2 0-4 296 CH (Me) CH 2 0CONHEt H 3-I 2-Cl-3-OCF 2 0-4 297 CH (Me) CH 2 OCONHEt H H 3-OCF 2
CF
2 0-4 112 298 CH (Me) CH 2 OCONHEt H 3-I 3-CF 2
CF
2 0-4 299 CH (Me) CH 2 OCONHEt H 3-I 3-OCF 2
CF
2 -4 300 CH (Me) CH 2 0CONHEt H 3-I 3-CF 2
CF
2
CF
2 -4 301 CH (Me) CH 2 OCONHEt H 3-I 3-CF 2
CF
2
CF
2
CF
2 -4 302 CH (Me) CH 2 NHCHO H 3-I 2-Me-4-CF (CF 3 ) 2 303 C (Me) 2
CH
2 NHCHO H 3-I 2-Me-4-CF (CF 3 ) 2 304 CH (Me) (CH2) 2 NHCHO H 3-I 2-Me-4-CF (CF 3
)
2 305 C (Me) 2 (CH 2 ) 2 NHCHO H 3-I 2-Me-4-CF (CF 3 ) 2 306 CH (Me) CH 2
NHCOCF
3 H 3-I 2-Me-4-CF (CF 3 ) 2 307 C(Me) 2
CH
2
NHCOCF
3 H 3-I 2-Me-4-CF(CF 3
)
2 308 C (Me) 2
CH
2
NHCOCF
3 H 3-I 2-Me-4-OCF 3 309 (CH2) 2 NHCOMe Me H 2-Me-4-CF (CF 3 ) 2 108 310 (CH2) 2
NHCOCH
2 -Ph Me H 2-Me-4-CF (CF 3 ) 2 311 (CH2 2 NHCO-Ph Me H 2-Me-4-CF (CF 3 ) 2 191 312 CH (Me) CH 2 NHC (=S) NHEt H H 2-Me-4-CF (CF 3 ) 2 185 313 C (Me) 2
CH
2
NHSO
2
CF
3 H 3-I 2-Me-4-CF (CF 3 ) 2 314 CH (Me) CH 2
NHSO
2
CF
3 H 3-I 2-Me-4-CF (CF 3 ) 2 315 C (Me) 2
CH
2
NHSO
2 -Ph H 3-I 2-Me-4-CF (CF 3 ) 2 316 CH (Me) CH 2
NHSO
2 -Ph H 3-I 2-Me-4-CF (CF 3 ) 2 - Cont' d - 66 Table 1 (Cont'd) Physical No. -A -B-R R2 Xn Ym property: Melting point *C 317 CH (Me) CH 2 NH (Me) SO 2 Me H 3-I 2-Cl-4-CF (CF 3 ) 2 190 318 (CH2) 2 N(Me)OMe H 3-I 2-Me-4-CF(CF 3
)
2 80 319 (CH2) 3 N(Me)OMe H 3-I 2-Me-4-CF(CF 3
)
2 91 320 (CH 2 ) 3 N (Me) OMe H 3-I 2-Me-4-OCF 3 154 321 (CH2) 2 NHCOMe Me H 2-Me-4-CF (CF 3 ) 2 187 322 C(Me) 2
CH
2 0CONHMe H 3-I 2-Me-4-CF(CF 3
)
2 180 67 Z' A-B-R' Qi NR Xn Xn --- Ym 3 Q 4 N ZR Table 2 (Z'=Z 2 =0, R 2
=R
3 =H) Melting No -A-B-R Q Q2 Q Q Xn Ym point OC 2-1 CH (Me) CH 2 OCONHEt N C C C C 3-Cl 2-Me-4-OCF 3 2-2 CH(Me)CH 2 0CON(Et) 2 N C C C C 3-Cl 2-Me-4-CF 2
CF
3 2-3 CH (Me) CH 2 0CONHCH 2 Ph N C C C C 3-Cl 2-Me-4-CF 2
CF
3 85 2-4 C (Me) 2
CH
2 0CONHMe N C C C C 3-Cl 2-Me-4-CF (CF 3 ) 2 2-5 CH (Me) CH 2 0CONHEt C N C C C H 2-Me-4-CF (CF 3 ) 2 100 2-6 CH(Me)CH 2 0CON(Et) 2 C N C C C 3-Br 2-Me-4-CF 3 2-7 CH (Me) CH 2 0CONHCH 2 Ph C N C C C H 2-Cl-4-CCF 3 2-8 C (Me) 2
CH
2 0CONHMe C N C C C H 2-Me-4-CF 2
CF
3 2-9 CH (Me) CH 2 OCONHEt C C N C C H 2-Me-4-OCF 3 2-10 CH (Me) CH 2 OCON (Et) 2 C C N C C H 2-Me-4-CF 2
CF
3 2-11 CH (Me) CH 2 0CONHCH 2 Ph C C N C C H 2-Me-4-CF (CF 3 ) 2 94 2-12 C (Me) 2 CH20CONHMe C C N C C H 2-Et-4-CF (CF 3 ) 2 2-13 CH (Me)CH 2 OCONHEt C C C N C H 2-Me-4-CF(CF 3
)
2 103 2-14 CH (Me) CH 2 0CON (Et) 2 C C C N C H 2-Cl-4-CF 3 2-15 CH (Me) CH 2 0CONHCH 2 Ph C C C N C H 2-Me-4-OCF 3 2-16 C(Me) 2
CH
2 0CONRMe C C C N C 3-I 2-Me-4-CF 2
CF
3 2-17 CH (Me) CH 2 OCONHEt N C N C C H 2-Me-4-OCF 3 2-18 CH(Me)CH 2 0CON(Et) 2 N C C N C H 2-Me-4-CF 2
CF
3 2-19 C(Me) 2
CH
2 0CONHMe C N C N C H 2-Me-4-CF(CF 3
)
2 - Cont' d - 1w 68 Table 2 (Cont'd) Melting No -A'-B-R' Q' Q 2
Q
3
Q
4 Q Xn Ym point 0C 2-20 CH (Me) CH 2 0CONHEt C C C C N 3-I 2-Me-4-CF 3 2-21 CH(Me)CH 2 0CON(Et) 2 C C C C N 3-I 2-Cl-4-CF 3 2-22 CH (Me) CH 2
OCONHCH
2 Ph C C C C N 3-I 2-Me-4-OCF 3 2-23 C(Me) 2
CH
2 0CONHMe C C C C N 3-I 2-Cl-4-OCF 3 2-24 CH (Me) CH 2 OCONHEt C C C C N 3-I 4-CF 2
CF
3 2-25 CH (Me) CH 2 0CON (Et) 2 C C C C N 3-I 2-Me-4-CF 2
CF
3 2-26 CH (Me) CH 2 0CONHCH 2 Ph C C C C N 3-I 2-Cl-4-CF 2
CF
3 2-27 C (Me) 2
CH
2 0CONHMe C C C C N 3-I 2-QMe-4-CF 2
CF
3 2-28 CH (Me) CH 2 OCON (Et) 2 C C C C N 3-I 4-CF (CF 3 ) 2 97 2-29 CH (Me)CH 2 0CON(Et) 2 C C C C N 6-I 4-CF(CF 3
)
2 119 2-30 CH (Me) CH 2 0CONHEt C C C C N 3-Cl 2-Me-4-CF (CF 3 ) 2 2-31 CH (Me) CH 2 0CONHEt C C C C N 3-Br 2-Me-4-CF (CF 3 ) 2 2-32 CH (Me)CH 2 0CON(Et) 2 C C C C N 3-I 2-Me-4-CF(CF 3
)
2 204 2-33 CH(Me)CH 2 0CON(Et) 2 C C C C N 6-I 2-Me-4-CF(CF 3
)
2 140 2-34 CH(Me)CH 2 0CONHCH 2 Ph C C C C N 3-I 2-Me-4-CF(CF 3
)
2 2-35 C (Me) 2
CH
2 OCONHMe C C C C N 3-I 2-Me-4-CF (CF 3 ) 2 176 2-36 CH (Me) CH 2
NHCO
2 Et C C C C N 3-I 2-Me-4-CF (CF 3 ) 2 2-37 CH (Me) CH 2 NHCOEt C C C C N 3-I 2-Me-4-CF (CF 3 ) 2 2-38 CH (Me) CH 2
NHSO
2 Et C C C C N 3-I 2-Me-4-CF (CF 3 ) 2 2-39 CH (Me) CH 2 OCONHEt C C C C N 3-I 2-Cl-4-CF (CF 3 ) 2 188 2-40 CH(Me)CH 2 0CON(Et) 2 C C C C N 3-I 2-Cl-4-CF(CF 3
)
2 2-41 CH (Me) CH 2 0CONHCH 2 Ph C C C C N 3-I 2-Cl-4-CF (CF 3 ) 2 2-42 C (Me) 2
CH
2 OCONHMe C C C C N 3-I 2-Cl-4-CF (CF 3 ) 2 2-43 CH (Me) CH 2 0CONHEt C C C C N 3-I 2-QMe-4-CF (CF 3 ) 2 - Cont'd - 1w 69 Table 2 (Cont'd) Melting No -A-B QQ 2 3
Q
4 5 Xn Ym point C 2-44 CH(Me)CH 2 0CON(Et) 2 C C C C N 3-I 2-cMe-4-CF(CF 3
)
2 2-45 CH (Me) CH 2 0CONHCH 2 Ph C C C C N 3-I 2-2Me-4-CF (CF 3 ) 2 2-46 C(Me) 2
CH
2 0CONHMe C C C C N 3-I 2-OMe-4-CF(CF 3
)
2 2-47 CH (Me) CH 2 0CONHEt C C C C N 3-I 2-Me-4-OCH (CF 3 ) 2 197 2-48 CH(Me)CH 2 0CON(Et) 2 C C C C N H 2-Me-4-OCH(CF 3
)
2 168 2-49 CH(Me)CH 2 0CON(Et) 2 C C C C N 3-I 2-Me-4-OCH(CF 3
)
2 226 2-50 CH (Me) CH 2 0CONHCH 2 Ph C C C C N 3-I 2-Me-4-OCH (CF 3 ) 2 210 2-51 C(Me) 2
CH
2 0CONHMe C C C C N 3-I 2-Me-4-OCH(CF 3
)
2 213 2-52 C (Me) 2
CH
2 0CONEMe C C C C N 6-I 2-Me-4-OCH (CF 3
)
2 222 2-53 CH (Me) CH 2
NHCO
2 Me C C C C N 3-I 2-Me-4-OCH (CF 3 ) 2 2-54 CH (Me) CH 2 NHCOMe C C C C N 3-I 2-Me-4-OCH (CF 3 ) 2 2-55 CH (Me) CH 2
NHSO
2 N (Me) 2 C C C C N 3-I 2-Me-4-OCH (CF 3 ) 2 2-56 CH (Me) CH 2 OCONEMe C C C C N 3-I 2-Me-4-OCHF 2 2-57 CH (Me) CH 2 0CON (Et) 2 C C C C N 3-I 2-Me-4-OCHF 2 2-58 CH (Me) CH 2 0CONHCH 2 Ph C C C C N 3-I 2-Me-4-CHF 2 2-59 C (Me) 2
CH
2 0CONHMe C C C C N 3-I 2-Me-4-OCF 2
CHF
2 2-60 CH (Me) CH 2 OCONHEt C C C C N 3-I 2-Me-4-OCF 2
CHF
2 2-61 CH(Me)CH 2 0CON(Et) 2 C C C C N 3-I 2-Me-4-OCF 2
CHF
2 2-62 CH (Me) CH 2 0CONHCH 2 Ph C C C C N 3-I 2-Me-4-ODCF 2
CHFCF
3 2-63 C (Me) 2
CH
2 0CONHMe C C C C N 3-I 2-Me-4-OCF 2
CHFCF
3 2-64 CH (Me) CH 2 0CONHEt C C C C N 3-I 2-Me-4-OCF 2
CHFCF
3 2-65 CH(Me)CH 2 0CON(Et) 2 C C C C N 3-I 2-Me-4-OCF 2
CHFCF
3 2-66 CH (Me) CH 2 0CONHCH 2 Ph C C C C N 3-I 2-Me-4-OCF 2
CHFCF
3 2-67 C (Me) 2
CH
2 0CONHRIe C C C C N 3-I 2-Me-4-OCF 2
CHFCF
3 - Cont'd - 70 Table 2 (Cont'd) Melting No -A-B-R Q Q2 Q Q Xn Ym point OC 2-68 CH (Me) CH 2 0CONHEt N C C C N 3-I 2-Me-4-OCF 2 2-69 CH (Me) CH 2 0CON (Et) 2 C N C C N 3-I 2-Me-4-CF 2
CF
3 2-70 CH (Me) CH 2 0CONHCH 2 Ph C C N C N 3-I 2-Me-4-CF (CF 3 ) 2 2-71 C(Me) 2
CH
2 0CONHMe C C C N N 3-I 2-Cl-4-CF(CF 3
)
2 2-72 CH (Me) CH 2 0CONH C C C C N 3-I 2-Me-4-OCH (CF 3 ) 2 201
-CH
2 (4- (aMe) -Ph) 2-73 CH (Me) CH 2 OP (=S) C C C C N 3-I 2-Me-4-OCH (CF 3 ) 2 157 -(Me) 2 2-74 CH (Me) CH 2 OP (=S) C C C C N 6-I 2-Me-4-OCH (CF 3 ) 2 134 - (OMe) 2 Table 3 shows 'H-NMR data of compounds having a physical property expressed by the word "amorphous" in Table 1.
71 Table 3 No. H-NMR[CDCl 3 /TMS, 5 values (ppm)] 80 1.33(d,3H), 2.37(s,3H), 3.91(dd,lH), 3.96(dd,1H), 4.55(m,1H), 6.32(d,1H), 6.78(d,2H), 6.94(dd,1H), 7.22(m,3H), 7.39(d,1H), 7.41(s,1H), 7.81(d,1H), 7.99(d,1H), 8.21(d,1H), 8.41(s,1H). 98 1.17(d,3H), 1.75-1.90(m,4H), 2.40(s,3H), 3.10-3.42 (m,4H), 4.02(dd,1H), 4.22(dd,1H), 4.32(m,1H), 6.89(d,lH), 7.22(dd,1H), 7.42(s,1H), 7.44(d,1H), 7.81(d,1H), 7.97(d,1H), 8.34(d,1H), 8.48(s,1H). 117 1.26(dt,6H), 1.28(d,3H), 2.38(s,3H), 4.08(m,6H), 4.39(s,1H), 6.79(d,1H), 7.23(dd,1H), 7.41(s,1H), 7.43(d,1H), 7.81(d,1H), 7.99(d,1H), 8.31(d,1H), 8.42(s,1H). Agricultural and horticultural chemicals, in particular, agricultural and horticultural insecti cides, which contain as an active ingredient the aromatic diamide derivative of the general formula (I) 5 or salt thereof of the present invention are suitable for controlling various insect pests such as agri cultural insect pests, forest insect pests, horti cultural insect pests, stored grain insect pests, sanitary insect pests, nematodes, etc., which are 10 injurious to paddy rice, fruit trees, vegetables, other crops, flowers and ornamental plants, and the like. They have a powerful insecticidal effect, for example, on LEPIDOPTERA including summer fruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix 72 (Adoxophyes sp.), Manchurian fruit moth (Grapholita inopinata), oriental fruit moth (Grapholita molesta), soybean pod borer (Leguminivora glycinivorella), mulberry leafroller (Olethreutes mori), tea leafroller 5 (Caloptilia thevivora), Caloptilia sp. (Caloptilia zachrysa), apple leafminer (Phyllonorycter ringoniella), pear barkminer (Spulerrina astaurota), common white (Piers rapae crucivora), tabacco budworm (Heliothis sp.), codling moth (Laspey resia pomonella), 10 diamondback moth (Plutella xylostella), apple fruit moth (Argyresthia conjugella), peach fruit moth (Carposina niponensis), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis), tabacco moth (Ephestia elutella), mulberry 15 pyralid (Glyphodes pyloalis), yellow rice borer (Scirpophaga incertulas), rice skipper (Parnara guttata), rice armyworm (Pseudaletia separata), pink borer (Sesamia inferens), common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), etc.; 20 HEMIPTERA including aster leafhopper (Macrosteles fascifrons), green rice leafhopper (Nephotettix cincticeps), brown rice planthopper (Nilaparvata lugens), whitebacked rice planthopper (Sogatella furcifera), citrus psylla (Diaphorina citri), grape 25 whitefly (Aleurolobus taonabae), sweetpotato whitefly (Bemisia tabaci), greenhouse whitefly (Trialeurodes vaporariorum), turnip aphid (Lipaphis erysimi), green peach aphid (Myzus persicae), Indian wax scale 73 (Ceroplastes ceriferus), cottony citrus scale (Pulvinaria aurantii), camphor scale (Pseudaonidia duplex), San Jose scale (Comstockaspis perniciosa), arrowhead scale (Unaspis yanonensis), etc.; COLEOPTERA 5 including root-lesion nematode (Pratylenchus sp.), soybean beetle (Anomala rufocuprea), Japanese beetle (Popillia japonica), tobacco beetle (Lasioderma serricorne), powderpost beetle (Lyctus brunneus), twenty-eight-spotted ladybird (Epilachna vigintiocto 10 punctata), adzuki bean weevil (Callosobruchus chinensis), vegetable weevil (Listroderes costiro stris), maize weevil (Sitophilus zeamais), boll weevil (Anthonomus gradis gradis), rice water weevil (Lissorhoptrus oryzophilus), cucurbit leaf beetle 15 (Aulacophora femoralis), rice leaf beetle (Oulema oryzae), striped flea beetle (Phyllotreta striolata), pine shoot beetle (Tomicus piniperda), Colorado potate beetle (Leptinotarsa decemlineata), Mexican beetle (Epilachna varivestis), corn rootworm (Diabrotica sp.), 20 etc.; DIPTERA including melon fly (Dacus(Zeugodacus) cucurbitae), oriental fruit fly (Dacus(Bactrocera) dorsalis), rice leafminer (Agromyza oryzae), onion maggot (Delia antiqua), seedcorn maggot (Delia platura), soybean pod gall midge (Asphondylia sp.), 25 muscid fly (Musca domestica), house mosquito (Culex pipiens pipiens), etc.; and TYLENCHIDA including coffee root-lesion nematode (Pratylenchus coffeae), potato cyst nematode (Globodera rostochiensis), root-knot 74 nematode (Meloidogyne sp.), citrus nematode (Tylenchulus semipenetrans), Aphelenchus sp. (Aphelenchus avenae), chrysanthemum foliar nematode (Aphelenchoides ritzemabosi), etc. 5 The agricultural and horticultural chemical, in particular, agricultural and horticultural insecticide, which contains as an active ingredient the aromatic diamide derivative of the general formula (I) or salt thereof of the present invention has a marked 10 insecticidal effect on the above-exemplified insect pests injurious to paddy field crops, upland crops, fruit trees, vegetables, other crops, flowers and ornamental plants, and the like. Therefore, the desired effect of the agricultural and horticultural 15 chemical, in particular, agricultural and horticultural insecticide of the present invention can be obtained by applying the agricultural and horticultural chemical to the paddy field water, stalks and leaves of fruit trees, vegetables, other crops, flowers and ornamental 20 plants, soil, etc., at a season at which the insect pests are expected to appear, before their appearance or at the time when their appearance is confirmed. The agricultural and horticultural chemical of the present invention is generally prepared into 25 conveniently usable forms according to an ordinary manner for preparation of agrochemicals. That is, the aromatic diamide derivative of the general formula (I) or a salt thereof and, 75 optionally, an adjuvant are blended with a suitable inert carrier in a proper proportion and prepared into a suitable preparation form such as a suspension, emulsifiable concentrate, soluble concentrate, wettable 5 powder, granules, dust, tablets or the like through dissolution, dispersion, suspension, mixing, impregna tion, adsorption or sticking. The inert carrier usable in the present invention may be either solid or liquid. As a material 10 usable as the solid carrier, there can be exemplified soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residue of vegetables, powdered synthetic polymers or resins, 15 clays (e.g. kaolin, bentonite, and acid clay), talcs (e.g. talc and pyrophyllite), silica powders or flakes (e.g. diatomaceous earth, silica sand, mica and white carbon [synthetic, high-dispersion silicic acid, also called finely divided hydrated silica or hydrated 20 silicic acid, some of commercially available products contain calcium silicate as the major component]), activated carbon, powdered sulfur, pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate, calcium phosphate and other 25 inorganic or mineral powders, chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride), and compost. These carriers may be used alone or as a mixture 76 thereof. A material usable as the liquid carrier is selected from materials that have solubility in themselves or which are without such solubility but are 5 capable of dispersing an active ingredient with the aid of an adjuvant. The following are typical examples of the liquid carrier and can be used alone or as a mixture thereof: water, alcohols (e.g. methanol, ethanol, isopropanol, butanol and ethylene glycol), 10 ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone), ethers (e.g. ethyl ether, dioxane, Cellosolve, dipropyl ether and tetrahydrofuran), aliphatic hydrocarbon (e.g. kerosene and mineral oils), aromatic hydrocarbons (e.g. 15 benzene, toluene, xylene, solvent naphtha and alkyl naphthalenes), halogenated hydrocarbons (e.g. dichloro ethane, chloroform, carbon tetrachloride and chloro benzene), esters (e.g. ethyl acetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate), 20 amides (e.g. dimethylformamide, diethylformamide and dimethylacetamide), nitriles (e.g. acetonitrile), and dimethyl sulfoxide. The following are typical examples of the adjuvant, which are used depending upon purposes and 25 used alone or in combination is some cases, or need not to be used at all. To emulsify, disperse, dissolve and/or wet a compound as active ingredient, a surfactant is used.
77 As the surfactant, there can be exemplified polyoxy ethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resonates, polyoxyethylene sorbitan 5 monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalene sulfonic acid condensation products, ligninsulfonates and higher alcohol sulfate esters. Further, to stabilize the dispersion of a 10 compound as active ingredient, tackify it and/or bind it, the adjuvants exemplified below may also be used, namely, there may also be used adjuvants such as casein, gelatin, starch, methyl cellulose, carboxy methyl cellulose, gum arabic, poly(vinyl alcohol)s, 15 turpentine, bran oil, bentonite and ligninsulfonates. To improve the flowability of a solid product, the following adjuvants may also be used, namely, there may.be used adjuvants such as waxes, stearates, alkyl phosphates, etc. 20 Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for dispersible products. Adjuvants such as silicone oils may also be used as a defoaming agent. 25 The content of the compound as active ingredient may be varied as required, and the compound as active ingredient may be used in a proportion properly chosen in the range of 0.01 to 90 parts by 78 weight per 100 parts of the agricultural and horti cultural insecticide. For example, in dusts or granules, the suitable content of the compound as active ingredient is from 0.01 to 50 % by weight. In 5 emulsifiable concentrates or flowable wettable powders, it is also from 0.01 to 50 % by weight. The agricultural and horticultural chemical, in particular, agricultural and horticultural insecti cide of the present invention is used to control a 10 variety of insect pests in the following manner: it is applied to a crop on which the insect pests are expected to appear, or a site where appearance or growth of the insect pests is undesirable, as it is or after being properly diluted with or suspended in water 15 or the like, in an amount effective for control of the insect pests. The applying dosage of the agricultural and horticultural insecticide of the present invention is varied depending upon various factors such as a 20 purpose, insect pests to be controlled, a growth state of a plant, tendency of insect pests appearance, weather, environmental conditions, a preparation form, an application method, an application site and application time. It may be properly chosen in the 25 range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, (in terms of the compound as active ingredient) per 10 ares depending upon purposes. The agricultural and horticultural chemical, 79 in particular, agricultural and horticultural insecti cide of the present invention may be used in admixture with other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, biotic pesticides 5 or the like in order to expand both spectrum of controllable insect pest species and the period of time when effective application are possible or to reduce the dosage. Furthermore, the agricultural and horticultural chemical of the present invention may be 10 used in admixture with herbicides, plant growth regulators, fertilizers or the like, depending upon application situations. As the other agricultural and horticultural insecticides, acaricides and nematicides, which are 15 used for the above purpose, there can be exemplified agricultural and horticultural insecticides, acaricides and nematicides, such as Ethion, Trichlorfon, Metamidophos, Acephate, Dichlorvos, Mevinphos, Monocrotophos, Malathion, Dimethoate, Formothion, 20 Mecarbam, Vamidothion, Thiometon, Disulfoton, Oxydeprofos, Naled, Methylpatathion, Fenitrothion, Cyanophos, Propaphos, Fenthion, Prothiofos, Profenofos, Isofenphos, Temephos, Phenthoate, Dimethylvinphos, Chlorfenvinphos, Tetrachlorvinphos, Phoxim, Isoxathion, 25 Pyraclofos, Methidathion, Chlorpyrifos, Chlorpyrifos methyl, Pyridaphenthion, Diazinon, Pirimiphosmethyl, Phosalone, Phosmet, Dioxabenzophos, Quinalphos, Terbuphos, Ethoprophos, Cadusafos, Mesulfenfos, DPS 'Rw 80 (NK-0795), Phosphocarb, Fenamiphos, Isoamidophos, Fosthiazate, Isazophos, Ethoprophos, Fostietane, Dichlofenthion, Thionazin, Sulprofos, Fensulfothion, Diamidafos, Pyrethrin, Allethrin, Prallethrin, 5 Resmethrin, Permethrin, Tefluthrin, Bifenthrin, Fenpropathrin, Cypermethrin, c-Cypermethrin, Cyhalothrin, X-Cyhalothrin, Deltamethrin, Acrinathrin, Fenvalerate, Esfenvalerate, Flucythrinate, Fluvalinate, Cycloprothrin, Ethofenprox, Halfenprox, Silafluofen, 10 Fluvalinate, Methomyl, Oxamyl, Thiodicarb, Aldicarb, Alanycarb, Cartap, Metolcarb, Xylylcarb, Propoxur, Phenoxycarb, Fenobucarb, Ethiophencarb, Fenothiocarb, Bifenazate, BPMC, Carbaryl, Pirimicarb, Carbofuran, Carbosulfan, Furathiocarb, Benfuracarb, Aldoxycarb, 15 Diafenthiuron, Diflubenzuron, Teflubenzuron, Hexaflumuron, Novaluron, Lufenuron, Flufenoxuron, Chlorfluazuron, Fenbutatin oxide, tricyclohexyltin hydroxide, sodium oleate, potassium oleate, Methoprene, Hydroprene, Binapacryl, Amitraz, Dicofol, Chroro 20 benzilate, Bromopropylate, Tetradifon, Bensultap, Benzoximate, Tebufenozide, Methoxyfenozide, Chromafenozide, Propargite, Acequinosyl, Endosulfan, Diofenolan, Chlorfenapyl, Fenpyroximate, Tolfenpyrad, Fipronil, Tebufenpyrad, Triazamate, Etoxazole, 25 Hexythiazox, nicotine sulfate, Nitenpyram, Acetamiprid, Thiacloprid, Imidacloprid, Thiamethoxam, Clothianidin, Nidinotefuran, Fluazinam, Pyriproxyfen, Hydramethylnon, Pyrimidifen, Pyridaben, Cyromazin, TPIC (tripropyl 81 isocyanurate), Pymetrozin, Clofentezin, Buprofedin, Thiocyclam, Fenazaquin, Chinomethionate, Indoxacarb, Polynactin complexes, Milbemectin, Abamectin, Emamectin-benzoate, Spinosad, BT (Bacillus 5 thuringiensis), Azadirachtin, Rotenone, hydroxypropyl starch, Levamisole hydrochloride, Metam-sodium, Morantel tartrate, Dazomet, Trichlamide, Pasteuria penetrans, Monacrosporium-phymatophagum, etc. As the agricultural and horticultural fungicides used for the 10 same purpose as above, there can be exemplified agricultural and horticultural fungicides such as sulfur, lime sulfur, copper sulfate basic, Iprobenfos, Edifenfos, Tolclofos-methyl, Thiram, Polycarbamate, Zineb, Maneb, Mancozeb, Propineb, Thiophanate, 15 Thiophanate methyl, Benomyl, Iminoctadin acetate, Iminocutadin albecylate, Mepronil, Flutolanil, Pencycuron, Furametpyl, Thifluzamide, Metalaxyl, Oxadixyl, Carpropamid, Dichlofluanid, Flusulfamide, Chlorothalonil, Kresoxim-methyl, Fenoxanil (NNF-9425), 20 Himexazol, Etridiazol, Fluoroimide, Procymidone, Vinclozolin, Iprodione, Triadimefon, Triflumizole, Bitertanol, Ipconazole, Fluconazole, Propiconazole, Diphenoconazole, Myclobutanil, Tetraconazole, Hexaconazole, Tebuconazole, Imibenconazole, Prochloraz, 25 Pefurazoate, Cyproconazole, Isoprothiolane, Fenarimol, Pyrimetanil, Mepanipyrim, Pyrifenox, Fluazinam, Triforine, Diclomezine, Azoxystrobin, Thiadiazin, Captan, Probenazole, Acibenzolar-S-methyl (CGA- 82 245704), Fthalide, Tricyclazole, Pyroquilon, Chinomethionat, Oxolinic acid, Dithianon, Kasugamycin, Validamycin, Polyoxin, Blasticidin, Streptomycin, etc. Similarly, as the herbicides, there can be exemplified 5 herbicides such as Glyphosate, Sulfosate, Glyfosinate, Bialaphos, Butamifos, Esprocarb, Prosulcarb, Benthiocarb, Pyributycarb, Asulam, Linulon, Dymron, Bensulfuron methyl, Cyclosulfamuron, Cinosulfuron, Pyrazosulfuron ethyl, Azimsulfuron, Imazosulfuron, 10 Tenylchlor, Alachlor, Pretilachlor, Clomeprop, Etobenzanid, Mefenacet, Pendimethalin, Bifenox, Acifluorfen, Lactfen, Cyhalofop-butyl, Ioxynil, Bromobutide, Alloxydim, Setoxydim, Napropamide, Indanofan, Pyrazolate, Benzofenap, Pyraflufen-ethyl, 15 Imazapyl, Sulfentrazone, Cafenstrole, Bentoxazon, Oxadiazon, Paraquat, Diquat, Pyriminobac, Simazine, Atrazine, Dimethametryn, Triazyflam, Benflesate, Flutiacet-methyl, Quizalofop-ethyl, Bentazon, calcium peroxide, etc. 20 As to the biotic pesticides, the same effect as above can be expected by using the agricultural and horticultural chemical of the present invention in admixture with, for example, viral formulations obtained from nuclear polyhedrosis virus (NPV), 25 granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), entomopox virus (EPV), etc.; microbial pesti cides utilized as insecticides or nematicides, such as Monacrosporium phymatophagum, Steinernema carpocapsae, 83 Steinernema kushidai, Pasteuria penetrans, etc.; microbial pesticides utilized as fungicides, such as Trichoderma lignorum, Agrobacterium radiobactor, nonpathogenic Erwinia carotovora, Bacillus subtilis, 5 etc.; and biotic pesticides utilized as herbicides, such as Xanthomonas campestris, etc. In addition, the agricultural and horti cultural chemical of the present invention can be used in combination with biotic pesticides including natural 10 enemies such as Parasitic wasp (Encarsia formosa), Parasitic wasp (Aphidius colemani), Gall-mildge (Aphidoletes aphidimyza), Parasitic wasp (Diglyphus isaea), Parasitic mite (Dacnusa sibirica), Predatory mite (Phytoseiulus persimilis), Predatory mite 15 (Amblyseius cucumeris), Predatory bug (Orius sauteri), etc.; microbial pesticides such as Beauveria brongniartii, etc.; and pheromones such as (Z)-10 tetradecenyl=acetate- (E,Z)-4,10-tetradecadienyl= acetate- (Z)-8-dodecenyl=acetate- (Z)-11-tetradecenyl= 20 acetate- (Z)-13-icosen-10-one, (Z)-8-dodecenyl= acetate- (Z)-11-tetradecenyl=acetate- (Z)-13-icosen-10 one-14-methyl-l-octadecene, etc. Typical examples of the present invention are described below but they should not be construed as 25 limiting the scope of the invention.
84 EXAMPLES Production Example 1 (1-1). Production of 3-iodo-N-(4-heptafluoroisopropyl 2-methylphenyl)phthalamic acid 5 A solution of 3.5 g of 4-heptafluoro isopropyl-2-methylaniline in 3 ml of acetonitrile was slowly dropped into a suspension of 3.5 g of 1 iodophthalic anhydride in 30 ml of acetonitrile under ice-cooling. After completion of the dropwise 10 addition, the reaction was carried out with stirring at room temperature for 3 hours. After completion of the reaction, the crystals precipitated were collected by filtration and washed with a small volume of aceto nitrile to obtain 4.0 g of the desired compound. 15 Physical property: m.p. 174 - 181'C. Yield: 57%. (1-2). Production of 3-iodo-N-(4-heptafluoroisopropyl 2-methylphenyl)phthalisoimide To a suspension of 2.0 g of 3-iodo-N-(4 heptafluoroisopropyl-2-methylphenyl)phthalamic acid in 20 10 ml of toluene was added 1.1 g of trifluoroacetic anhydride, and the reaction was carried out with stirring at room temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 2.0 g of a crude 25 product as the desired product. The desired product obtained was used in the subsequent reaction without purification.
85 'H-NMR [CDCl 3 /TMS, 6 values (ppm)] 2.4(s, 3H), 7.3(d, 1H), 7.4(m, 2H), 7.5(t, 1H), 8.1(d, 1H), 8.2(d, 1H) (1-3). Production of 3-iodo-N'-(4-heptafluoroisopropyl 5 2-methylphenyl)-N 2 -[1-methyl-2-(N,N-dimethyl sulfamoylamino)ethyl]phthalamide (compound No. 45) In 30 ml of acetonitrile was dissolved 0.4 g of 3-iodo-N-(4-heptafluoroisopropyl-2-methylphenyl) 10 phthalisoimide, followed by adding thereto 0.2 g of N,N-dimethylamino-N'-(2-aminopropyl)sulfonamide, and the resulting mixture was stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was poured into ice water, followed by 15 extraction with ethyl acetate. The organic layer was washed with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent, and the resulting residue was purified by silica gel column 20 chromatography to obtain 0.2 g of the desired compound. Physical property: m.p. 95*C. Yield: 40%. Production Example 2 Production of 3-iodo-N'-(4-heptafluoro isopropyl-2-methylphenyl)-N 2 -[1-methyl-2-(ethylamino 25 carbonyloxy)ethyl]phthalamide (compound No. 96) In 30 ml of acetonitrile was dissolved 0.55 g of 6-iodo-N-[1-methyl-2-(ethylaminocarbonyloxy)ethyl]- 86 phthalisoimide, followed by adding thereto 0.38 g of 4 heptafluoroisopropyl-2-methylaniline, and the resulting mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture 5 was poured into ice water, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent, and the resulting 10 residue was purified by silica gel column chromato graphy to obtain 0.36 g of the desired compound. Physical property: m.p. 185*C. Yield: 38%. Production Example 3 (3-1). Production of 3-iodo-N-(4-heptafluoroisopropyl 15 2-methylphenyl)phthalimide To a suspension of 2.7 g of 3-iodophthalic anhydride in 30 ml of acetic acid was added 2.7 g of 4 heptafluoroisopropyl-2-methylaniline, and the resulting mixture was heated under reflux for 3 hours. 20 After completion of the reaction, the solvent was distilled off under reduced pressure from the reaction mixture, and the resulting residue was purified by silica gel column chromatography to obtain 4.8 g of the desired compound. 25 Yield: 89%.
87 (3-2). Production of 3-iodo-N'-(4-heptafluoroisopropyl 2-methylphenyl)-N 2 -[3-t-butoxycarbonyl aminopropyl)phthalamide (compound No. 20) 5 In 20 ml of dioxane was dissolved 0.5 g of 3 iodo-N-(4-heptafluoroisopropyl-2-methylphenyl) phthalimide, followed by adding thereto 0.25 g of t butyl N-(3-aminopropyl)carbamate and two drops of trifluoroacetic acid, and the resulting mixture was 10 stirred at room temperature for 10 hours. After completion of the reaction, the reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous sodium chloride solution, dried over anhydrous 15 magnesium sulfate and then distilled under reduced pressure to remove the solvent, and the resulting residue was purified by silica gel column chromato graphy to obtain 0.2 g of the desired compound. Physical property: m.p. 145*C. Yield: 30%. 20 Typical formulation examples and test examples of the present invention are described below but they should not be construed as limiting the scope of the invention. In the formulation examples, parts are all by 25 weight.
88 Formulation Example 1 Each compound listed in Table 1 50 parts or Table 2 Xylene 40 parts 5 Mixture of polyoxyethylene 10 parts nonylphenyl ether and calcium alkylbenzenesulfonate An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect 10 dissolution. Formulation Example 2 Each compound listed in Table 1 3 parts or Table 2 Clay powder 82 parts 15 Diatomaceous earth powder 15 parts A dust was prepared by mixing uniformly and grinding the above ingredients. Formulation Example 3 Each compound listed in Table 1 5 parts 20 or Table 2 Mixed powder of bentonite and clay 90 parts Calcium lignin sulfonate 5 parts Granules were prepared by mixing the above ingredients uniformly, and kneading the resulting 25 mixture together with a suitable amount of water, followed by granulation and drying.
89 Formulation Example 4 Each compound listed in Table 1 20 parts or Table 2 Mixture of kaolin and synthetic, 75 parts 5 high-dispersion silicic acid Mixture of polyoxyethylene 5 parts nonylphenyl ether and calcium alkylbenzenesulfonate A wettable powder was prepared by mixing 10 uniformly and grinding the above ingredients. Test Example 1 Insecticidal effect on diamondback moth (Plutella xylostella) Adult diamondback moths were released and 15 allowed to oviposit on a Chinese cabbage seedling. Two days after the release, the seedling having eggs deposited thereon was immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Table 1 or Table 2, 20 as an active ingredient to adjust the concentration to 50 ppm. After air-drying, the seedling was allowed to stand in a room thermostated at 25 0 C. Six days after the immersion in the liquid chemical, the hatched insects were counted and the 25 mortality was calculated according to the following equation, whereby the insecticidal effect was judged according to the criterion shown below. The test was 90 carried out with three replications of 10 insects. Number of Number of hatched insects hatched insects in untreated - in treated group group Corrected mortality (%)= x 100 Number of hatched insects in untreated group Criterion for judgment A --- mortality 100% B --- mortality 99% to 90% 5 C --- mortality 89% to 80% D --- mortality 79% to 50% As a result of the above test, it was found that the following compounds had an insecticidal activity rated B or higher: compound Nos. 1 to 122, 127 10 to 130, 133 to 136, 139, 140, 142 to 145, 148, 149, 152, 153, 157, 161, 165, 167 to 173, 182 to 185, 194, 198, 199, 204, 205, 210 to 212, 214 to 216, 222, 223, 229, 230, 235, 236, 243, 247, 259, 260, 263 to 272, 274, 275, 278 to 280, 284 to 290, 293, 297, 308, 311, 15 312, 317 to 322, 2-3, 2-5, 2-11, 2-13, 2-28, 2-29, 2 32, 2-33, 2-35, 2-39, 2-47 to 2-52, 2-72, 2-73 and 2 74. Test Example 2 Insecticidal effect on common cutworm (Spodoptera 20 litura) 91 A piece of cabbage leaf (cultivar: Shikidori) was immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Table 1 or Table 2, as an active 5 ingredient to adjust the concentration to 50 ppm. After air-drying, the piece was placed in a plastic Petri dish with a diameter of 9 cm and inoculated with second-instar larvae of common cutworm, after which the dish was closed and then allowed to stand in a room 10 thermostated at 25*C. Eight days after the inoculation, the dead and alive were counted and the mortality was calculated according to the following equation, whereby the insecticidal effect was judged according to the criterion shown in Test Example 1. The test was 15 carried out with three replications of 10 insects. Number of Number of alive insects alive insects in untreated - in treated group J group J Corrected mortality (%)= g u100 Number of alive insects in untreated group I As a result of the above test, it was found that the following compounds had an activity rated B or higher: compound Nos. 1, 2, 6 to 9, 12 to 16, 19, 22, 28, 29, 33 to 36, 38 to 45, 48, 50, 51, 54 to 57, 59, 20 62 to 72, 74, 76 to 78, 81 to 86, 88, 90 to 113, 116, 117, 129, 130, 133, 134, 139, 142, 144, 148, 152, 153, 172, 184, 229, 247, 272, 274, 279, 286, 287, 289, 290, 92 2-32, 2-35, 2-39, 2-47, 2-49 to 2-51, 2-72 and 2-73. Test Example 3 Insecticidal effect on smaller tea tortrix (Adoxophyes sp.) 5 Tea leaves were immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Table 1 or Table 2, as an active ingredient to adjust the concentration to 50 ppm. After air-drying, the tea leaves were placed 10 in a plastic Petri dish with a diameter of 9 cm and inoculated with larvae of smaller tea tortrix, after which the dish was allowed to stand in a room thermo stated at 250C and having a humidity of 70%. Eight days after the inoculation, the dead and alive were counted 15 and the insecticidal effect was judged according to the criterion shown in Test Example 1. The test was carried out with three replications of 10 insects. As a result of the above test, it was found that the following compounds had an activity rated B or 20 higher: compound Nos. 1 to 4, 6 to 10, 12 to 16, 19 to 26, 28 to 45, 48 to 51, 54 to 60, 62 to 72, 74 to 78, 80 to 117, 129, 130, 133 to 136, 139, 140, 142, 144, 145, 148, 149, 152, 153, 170, 182, 184, 210, 247, 265, 272, 274, 279, 284, 286, 287, 289, 290, 317, 322, 2-32, 25 2-35, 2-39, 2-47, 2-49 to 2-51, 2-72 and 2-73.

Claims (4)

1. An aromatic diamide derivative represented by the general formula (I): z 1 -B-R 1 L 2 Q.5 Q N-R2 Xn---- Ym (I) Q1 Z2 R 3Q {wherein A' is a (Cl-C) alkylene group; a substituted (C 1 -C)alkylene group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo (Cl-C.) alkyl groups, (Cl-C.) alkoxy groups, halo (C, C 6 ) alkoxy groups, (Cl-C,) alkylthio groups, halo (Cl C 6 ) alkylthio groups, (Cl-C) alkylsulfinyl groups, halo (Cl-c,) alkylsulfinyl groups, (C1-C) alkylsulfonyl groups, halo (C1-C6) alkylsulfonyl groups, (C-C6) alkyl thio(C 1 -C)alkyl groups, (C-C,)alkoxycarbonyl groups and phenyl group; a (C 3 -C)alkenylene group; a substituted (C 3 -C)alkenylene group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo(C 1 C 6 ) alkyl groups, (Cl-C) alkoxy groups, halo (Cl-C) alkoxy groups, (Cl-CE) alkylthio groups, halo (Cl-C.) alkylthio groups, (Cl-CE) alkylsulfinyl groups, halo (C-C6) alkyl sulfinyl groups, (C1-C6) alkylsulfonyl groups, halo (Cl C0) alkylsulfonyl groups, (C-C) alkylthio (C-C6) alkyl 94 groups, (C 1 -C) alkoxycarbonyl groups and phenyl group; a (C 3 -C)alkynylene group; or a substituted (C 3 -C,)alkyny lene group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo (Cl-C 6 ) alkyl groups, (C 1 -C.) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (C 1 -C 6 ) alkylthio groups, halo (Cl-C.) alkylthio groups, (C 1 -C 6 ) alkylsulfinyl groups, halo (Ci-C 6 ) alkylsulfinyl groups, (Cl-Cs) alkylsulfonyl groups, halo (Cl-C 6 ) alkyl sulfonyl groups, (C 1 -C,) alkylthio (Ci-C,) alkyl groups, (Cl-C,) alkoxycarbonyl groups and phenyl group, any of the saturated carbon atoms in the above-mentioned (Cl-C)alkylene group, substituted (Cl C 8 ) alkylene group, (C 3 -C)alkenylene group, substituted (C 3 -C) alkenylene group, (C 3 -C)alkynylene group or substituted (C 3 -C)alkynylene group being able to have a (C 2 -C 5 )alkylene group bonded thereto as a substituent, to form a (C 3 -C,) cycloalkane ring, and any two of the carbon atoms in the above-mentioned (Cl-C) alkylene group, substituted (Ci-C) alkylene group, (C 3 -C,) alkeny lene group and substituted (C 3 -C)alkenylene group being able to form a (C 3 -C,) cycloalkane ring or a (C 3 -C 6 ) cyclo alkene ring together with an alkylene group or an alkenylene group, B is -0- or -N(R 4 )- (wherein R 4 is a hydrogen atom; a (Ci-C.) alkyl group; a halo (Cl-C.) alkyl group; a (C 3 -C 6 ) alkenyl group; a halo (C 3 -C,) alkenyl group; a (C 3 C.) alkynyl group; a (C 3 -C,) cycloalkyl group; a (C 1 - 95 C 6 ) alkylcarbonyl group; a halo (Cl-C.) alkylcarbonyl group; a (Ci-C 6 )alkoxycarbonyl group; a phenylcarbonyl group; a substituted phenylcarbonyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C.) alkyl groups, halo (Cl-C.) alkyl groups, (Ci C 6 ) alkoxy groups, halo (Cl-C) alkoxy groups, (Cl-C) alkyl thio groups, halo (Cl-C) alkylthio groups, (C 1 -C 6 ) alkyl sulfinyl groups, halo (Cl-C) alkylsulfinyl groups, (Cl C 6 ) alkylsulfonyl groups, halo (Cl-C) alkylsulfonyl groups, mono (C-C 6 )alkylamino groups, and di (Ci-C 6 ) alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different; a phenyl(Cl-C 4 )alkoxycarbonyl group; a substituted phenyl (C 1 -C 4 )alkoxycarbonyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano. group, nitro group, (Cl-C 6 ) alkyl groups, halo (C 1 -C 6 ) alkyl groups, (Cl-C) alkoxy groups, halo (Ci-C.) alkoxy groups, (C1-C6) alkylthio groups, halo (Cl-C 6 ) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (C-C6) alkylsulfonyl groups, halo (C-C6) alkyl sulfonyl groups, mono (Ci-C 6 )alkylamino groups, and di(C 1 C 6 ) alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different; a phenyl (C 1 -C 4 )alkyl group; or a substituted phenyl (C 1 -C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C) alkyl groups, halo (C-C) alkyl 96 groups, (Cl-C) alkoxy groups, halo (Ci-CE) alkoxy groups, (Cl-Cs) alkylthio groups, halo (C1-C6) alkylthio groups, (C-C6) alkylsulfinyl groups, halo (C1-C6) alkylsulfinyl groups, (C-C6) alkylsulfonyl groups, halo (Cl-C) alkyl sulfonyl groups, mono (C 1 -C 6 )alkylamino groups, di(C, C 6 ) alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (C 1 -C,)alkoxycarbonyl groups), R' is a hydrogen atom; a (Ci-C)alkyl group; a halo (Ci-C) alkyl group; a (C-C4) alkoxy (C 1 -C 4 ) alkyl group; a (C 1 -C 4 )alkylthio (C 1 -C 4 )alkyl group; a (C2 CE) alkenyl group; a halo (C2-C6) alkenyl group; a (C3 C 6 )alkynyl group; a halo (C 3 -C6)alkynyl group; a (C3 C) cycloalkyl group; a halo (C3-C6) cycloalkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C6) alkyl groups, halo (Cl-C) alkyl groups, (Cl C0) alkoxy groups, halo (Cl-C) alkoxy groups, (Cl-C) alkyl thio groups, halo (Cl-C) alkylthio groups, (Cl-CE) alkyl sulfinyl groups, halo (Cl-C) alkylsulfinyl groups, (Cl CE) alkylsulfonyl groups, halo (Cl-C) alkylsulfonyl groups, mono (Cl-C) alkylamino groups, di (Cl-C) alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (Cl-CE) alkoxycarbonyl groups; a phenyl (C1-C4) alkyl group; a substituted phenyl (C-C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 )alkyl groups, halo (C-C 6 )alkyl 97 groups, (Cl-C) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (Cl-C,) alkylthio groups, halo (C1-C6) alkylthio groups, (C,-C,) alkylsulfinyl groups, halo (Ci-C) alkylsulfinyl groups, (C1-C) alkylsulfonyl groups, halo (Ci-C) alkyl sulfonyl groups, mono (Cl-C6) alkylamino groups, di (Cl C0)alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C 6 )alkyl groups, halo (Ci-C 6 )alkyl groups, (Cl-C,) alkoxy groups, halo (Cl-C) alkoxy groups, (C-C6) alkylthio groups, halo (Cl-C) alkylthio groups, (Cl-C6) alkylsulfinyl groups, halo (C-C6) alkylsulfinyl groups, (C-C6) alkylsulfonyl groups, halo (Cl-C6) alkyl sulfonyl groups, mono (Cl-C.) alkylamino groups, di(C C,)alkylamino groups whose (Ci-C,)alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; -P(=Wl) (-OR 5 ) (-OR 6 ) (wherein W1 is an oxygen atom or a sulfur atom, and each of R 5 and R 6 , which may be the same or different, is a hydrogen atom; a (Cl-C 6 )alkyl group; a halo (Cl-C.) alkyl group; a (C 1 -C 4 ) alkoxy (Cl C 4 )alkyl group; a (C-C 4 )alkylthio (C 1 -C 4 )alkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C) alkyl groups, halo (Cl-C6) alkyl groups, (Cl C6) alkoxy groups, halo (Cl-C.) alkoxy groups, (Cl-C) alkyl- 98 thio groups, halo (C 1 -C 6 ) alkylthio groups, (C-C) alkyl sulfinyl groups, halo (Ci-C) alkylsulfinyl groups, (C, C0) alkylsulfonyl groups, halo (C-C6) alkylsulfonyl groups, mono (Ci-C) alkylamino groups, di (C-C6) alkylamino groups whose (Ci-C)alkyl groups may be the same or different, and (C-C6) alkoxycarbonyl groups; a phenyl (C1-C4) alkyl group; a substituted phenyl (C 1 -C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C) alkyl groups, halo (C1-C6) alkyl groups, (C1-C) alkoxy groups, halo (C-C6) alkoxy groups, (C1-C6) alkylthio groups, halo (C1-C) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C-C) alkylsulfinyl groups, (C1-C) alkylsulfonyl groups, halo (C1-C) alkyl sulfonyl groups, mono (Ci-C) alkylamino groups, di(C 1 C) alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (C 1 -C 6 )alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C1-C6) alkyl groups, halo (C1-C6) alkyl groups, (C-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C-C6) alkylthio groups, halo (C1-C6) alkylthio groups, (C1-C) alkylsulfinyl groups, halo (C1-C) alkylsulfinyl groups, (C-C6) alkylsulfonyl groups, halo (C1-C6) alkyl sulfonyl groups, mono (C 1 -C) alkylamino groups, di(Ci C6) alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (Ci-C 6 )alkoxycarbonyl groups, 99 further, R 5 being able to bind to R 6 to form a
5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); -C (=W) -N (R') (R 6 ) (wherein W', R 5 and R6 are as defined above, R 5 being able to bind to R 6 to form a 5- to 8 membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, and R 5 being able to bind to R 4 to form a 5- to 8-membered ring that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); -C(=W)-R (wherein W1 and R 5 are as defined above) ; -C (=Wl) -W'-R' (wherein Wis, which may be the same or different, are as defined above, and R 7 is a (C 1 -C 6 )alkyl group; a halo (C 1 -C 6 )alkyl group; a (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl group; a (C 1 -C 4 ) alkyl thio (C 1 -C 4 )alkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 )alkyl groups, halo (Cl-C 6 ) alkyl groups, (Cl-C 6 ) alkoxy groups, halo (Ci C 6 ) alkoxy groups, (Ci-C 6 )alkylthio groups, halo(C 1 C 6 )alkylthio groups, (C,-C 6 )alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Cl-C,) alkylsulfonyl 100 groups, halo (Ci-C,) alkylsulfonyl groups, mono (Cl C.) alkylamino groups, di (Ci-C 6 ) alkylamino groups whose (C 1 -C,)alkyl groups may be the same or different, and (Cl-CE) alkoxycarbonyl groups; a phenyl (C 1 -C 4 ) alkyl group; a substituted phenyl (C 1 -C 4 ) alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C.) alkyl groups, halo (C 1 -C6) alkyl groups, (Ci-C 6 ) alkoxy groups, halo (Cl-C6) alkoxy groups, (C 1 -C 6 ) alkylthio groups, halo (Ci-C 6 ) alkylthio groups, (Cl-C 6 ) alkylsulfinyl groups, halo (C,-C6) alkylsulfinyl groups, (Cl-C) alkylsulfonyl groups, halo (Cl-C) alkyl sulfonyl groups, mono (C 1 -C.) alkylamino groups, di(Cl CE) alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 )alkyl groups, halo (C 1 -CE) alkyl groups, (Cl-C) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (Cl-CE) alkylthio groups, halo (Cl-C) alkylthio groups, (Cl-C) alkylsulfinyl groups, halo (Cl-CE) alkylsulfinyl groups, (Cl-C) alkylsulfonyl groups, halo (Cl-C) alkyl sulfonyl groups, mono (Cl-C) alkylamino groups, di(Ci CE) alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups); -S0 2 -R' (wherein R' is as defined above); -S0 2 -N(R') (R) (wherein R' and RE are as defined above, R' being able to 101 bind to R 6 to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, and R' being able to bind to R 4 to form a 5- to 8-membered ring that may contain three or four atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); -N(R5) (R 6 ) (wherein R 5 and R 6 are as defined above, R 5 being able to bind to R 6 to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, and R' being able to bind to R 4 to form a 5- to 8-membered ring that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms consti tuting the ring); or -N=C(R 5 )R 6 (wherein R 5 and R 6 are as defined above, R' being able to bind to R 6 to form a 5 to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); in the case of B being -N(R 4 )-, R' being able to be -OR5 (wherein R 5 is as defined above), -C(W 2 )-N(R 5 )R 6 (wherein W2 is =CH-N0 2 , =N-N0 2 or =N-CN, and R5 and R6 are as 102 defined above, R 5 or R 6 being able to bind to R 4 to form a 5- to 8-membered ring that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring) or -C(W 2 )-W'-R 7 (wherein Wi, W 2 and R 7 are as defined above, R 7 being able to bind to R 4 to form a 5 to 8-membered ring that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring), and R' being able to bind to A' to form a 5- to 8 membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, each of R 2 and R 3 , which may be the same or different, is a hydrogen atom, a (C 3 -C 6 )cycloalkyl group or -A 2 -R' (wherein A2 is -C(=O)-, -C(=S)-, -C(=NR 9 ) (wherein R 9 is a hydrogen atom, a (CI-C 6 )alkyl group, a (C,-C 6 ) alkoxy group, a mono (C1-C 6 ) alkylamino group, a di (Cl-C 6 ) alkylamino group whose (C-C 6 ) alkyl groups may be the same or different, a (C,-C,)alkoxycarbonyl group, a phenyl group, or a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C1-C 6 ) alkyl groups, halo (Cl-C.) alkyl groups, (Cl-C.) alkoxy groups, halo (Cl-C) alkoxy groups, 103 (Cl-C6) alkylthio groups, halo (C,-C 6 ) alkylthio groups, (C 1 -C 6 ) alkylsulfinyl groups, halo (C 1 -C 6 ) alkylsulfinyl groups, (C 1 -C 6 ) alkylsulfonyl groups, halo (C-C 6 ) alkyl sulfonyl groups, mono (Cl-C)alkylamino groups, di(C 1 C)alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (Ci-C)alkoxycarbonyl groups), a (Cl-C)alkylene group, a halo (Cl-C 8 ) alkylene group, a (C 3 -C,)alkenylene group, a halo (C 3 -C 6 )alkenylene group, a (C 3 -C 6 )alkynylene group or a halo (C 3 -C 6 )alkynylene group, (1) in the case of A2 being -C(=O)-, -C(=S) or -C(=NR 9 )- (wherein R' is as defined above), R' is a hydrogen atom; a (C 1 -C) alkyl group; a halo (C 1 -C6)alkyl group; a (C 3 -C) cycloalkyl group; a halo (C 3 -C) cycloalkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 ) alkyl groups, halo (Cl-C.) alkyl groups, (C 1 -C) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (Cl-C6) alkylthio groups, halo (C 1 -C 6 ) alkylthio groups, (C 1 -C 6 ) alkylsulfinyl groups, halo (Ci-C 6 ) alkylsulfinyl groups, (C 1 -C,) alkylsulfonyl groups, halo (Cl-C 6 ) alkyl sulfonyl groups, mono (Ci-C 6 )alkylamino groups, di(C 1 C 6 ) alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (CI-C 6 )alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 )alkyl groups, halo(Ci-C.)alkyl 104 groups, (Ci-C6) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (C 1 -C 6 ) alkylthio groups, halo (Ci-C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (Ci-C6) alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups, halo (C 1 -C 6 ) alkyl sulfonyl groups, mono (C 1 -C) alkylamino groups, di(C 1 C 6 ) alkylamino groups whose (C-C)alkyl groups may be the same or different, and (C-C 6 )alkoxycarbonyl groups; or -A-R 0 (wherein A3 is -0-, -S- or -N(R")- (wherein R" is a hydrogen atom; a (C1-C6) alkylcarbonyl group; a halo (C1 C6) alkylcarbonyl group; a (Cl-C 6 )alkoxycarbonyl group; a phenylcarbonyl group; a substituted phenylcarbonyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C 6 )alkyl groups, halo(Ci C6) alkyl groups, (C1-C6) alkoxy groups, halo (C1-C) alkoxy groups, (C1-C) alkylthio groups, halo (C1-C6) alkylthio groups, (C-C6) alkylsulfinyl groups, halo (C1-C6) alkyl sulfinyl groups, (C,-C,)alkylsulfonyl groups, halo(C 1 C6) alkylsulfonyl groups, mono (C-C6) alkylamino groups, di (C 1 -C 6 ) alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (C 1 -C 6 )alkoxycarbonyl groups; a phenyl(C 1 -C 4 )alkoxycarbonyl group; or a substituted phenyl(C 1 -C 4 )alkoxycarbonyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C1-C) alkyl groups, halo (C1-C6) alkyl groups, (C1-C) alkoxy groups, halo (C1-C6) alkoxy groups, (CC6) alkylthio groups, halo (C1-C6) alkylthi-o groups, 105 (Ci-C 6 ) alkylsulfinyl groups, halo (Cl-C6) alkylsulfinyl groups, (C-C 6 ) alkylsulfonyl groups, halo (C-C6) alkyl sulfonyl groups, mono (Cl-C) alkylamino groups, di(Cl C) alkylamino groups whose (C1-C,)alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups), and R1 0 is a (Cl-C 6 )alkyl group; a halo (C-C) alkyl group; a (C3-C) alkenyl group; a halo (C3-C6) alkenyl group; a (C3-C) alkynyl group; a halo (C3-C6) alkynyl group; a (C3 C6) cycloalkyl group; a halo (C3-C) cycloalkyl group; a (C1-C6) alkylcarbonyl group; a halo (Cl-C6) alkylcarbonyl group; a (C-C 6 )alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more substit uents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C6) alkyl groups, halo (C-C6) alkyl groups, (C C) alkoxy groups, halo (CI-C) alkoxy groups, (C-C,) alkyl thio groups, halo (Cl-C6) alkylthio groups, (C-C6) alkyl sulfinyl groups, halo (C-C 6 )alkylsulfinyl groups, (C C) alkylsulfonyl groups, halo (C-C) alkylsulfonyl groups, mono (C-C.) alkylamino groups, di (C,-C6) alkylamino groups whose (C-C)alkyl groups may be the same or different, and (Cl-C) alkoxycarbonyl groups; a phenyl (C-C4) alkyl group; a substituted phenyl (C-C4) alkyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C) alkyl groups, halo (C-C6) alkyl groups, (C C6) alkoxy groups, halo (C-C6) alkoxy groups, (C,-C) alkyl thio groups, halo (Cl-C) alkylthio groups, (Cl-C) alkyl- 106 sulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Cl C,) alkylsulfonyl groups, halo (Cl-C 6 ) alkylsulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di (Cl-C,) alkylamino groups whose (C-C,)alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 ) alkyl groups, halo (C 1 -C 6 ) alkyl groups, (Cl C0) alkoxy groups, halo (Cl-C) alkoxy groups, (C 1 -C,) alkyl thio groups, halo (Cl-C.) alkylthio groups, (Cl-C,) alkyl sulfinyl groups, halo (C 1 -C) alkylsulfinyl groups, (C 1 C 6 )alkylsulfonyl groups, halo (Cl-C 6 ) alkylsulfonyl groups, mono (Ci-C 6 ) alkylamino groups, di (Cl-C 6 ) alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (Cl-C,) alkoxycarbonyl groups), (2) in the case of A2 being a (C-C,)alkylene group, a halo (C 1 -C) alkylene group, a (C 3 -C,)alkenylene group, a halo (C 3 -C) alkenylene group, a (C 3 -C,)alkynylene group or a halo (C 3 -C 6 ) alkynylene group, R' is a hydrogen atom; a halogen atom; a cyano group; a nitro group; a (C 3 -C 6 ) cycloalkyl group; a halo (C 3 -C 6 ) cycloalkyl group; a (C-C)alkoxycarbonyl group; a phenyl group; a substi tuted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 C 6 ) alkyl groups, halo (C 1 -C 6 ) alkyl groups, (C 1 -C 6 ) alkoxy groups, halo (C 1 -C 6 ) alkoxy groups, (C 1 -C 6 ) alkylthio 107 groups, halo (Cl-C.) alkylthio groups, (Ci-C,) alkylsulfinyl groups, halo (Cl-C.) alkylsulfinyl groups, (Ci-C 6 ) alkyl sulfonyl groups, halo (Ci-C 6 ) alkylsulfonyl groups, mono (C 1 -C.) alkylamino groups, di (C 1 -C 6 ) alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C) alkyl groups, halo (Ci-C 6 ) alkyl groups, (Cl C 6 ) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (C 1 -C 6 ) alkyl thio groups, halo (Cl-C,) alkylthio groups, (Cl-C 6 ) alkyl sulfinyl groups, halo (Cl-C,) alkylsulfinyl groups, (Ci C,) alkylsulfonyl groups, halo (C,-C,) alkylsulfonyl groups, mono (Cl-CE) alkylamino groups, di (Cl-CE) alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (C-C 6 ) alkoxycarbonyl groups; or -A 4 -R" (wherein A 4 is -0-, -S-, -SO-, -S02-, -N(R")- (wherein R" is as defined above), -C(=O)-, or -C(=N-OR 3 ) (wherein R" is a hydrogen atom, a (C-C,) alkyl group, a halo (Ci-C) alkyl group, a (C 3 -C 6 )alkenyl group, a halo (C 3 -C 6 ) alkenyl group, a (C 3 -C 6 ) alkynyl group, a halo (C 3 -C 6 ) alkynyl group, a (C 3 -C 6 ) cycloalkyl group, a phenyl (C 1 -C 4 ) alkyl group, or a substituted phenyl(Cl-C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 )alkyl groups, halo(C 1 C,) alkyl groups, (Ci-C 6 ) alkoxy groups, halo (Ci-C 6 ) alkoxy 108 groups, (Ci-C.) alkylthio groups, halo (C 1 -C 6 ) alkylthio groups, (Cl-C,) alkylsulfinyl groups, halo (C 1 -C.) alkyl sulfinyl groups, (Cl-C,) alkylsulfonyl groups, halo (Cl C,) alkylsulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di (C,-C 6 ) alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (Ci-C,)alkoxycarbonyl groups), (i) in the case of A 4 being -0-, -S-, -SO-, -SO 2 - or -N(R")- (wherein R"is as defined above), R1 2 is a hydrogen atom; a (Cl-C,) alkyl group; a halo (C 1 -C.) alkyl group; a (C 3 -C,) alkenyl group; a halo (C3-C) alkenyl group; a (C 3 -C,)alkynyl group; a halo (C3-C6) alkynyl group; a (C 3 -C 6 )cycloalkyl group; a halo (C 3 -C,) cycloalkyl group; a (Cl-C 6 )alkylcarbonyl group; a halo (C 1 -C 6 ) alkyl carbonyl group; a (C 1 -C 6 )alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C1-C) alkyl groups, halo (C1-C6) alkyl groups, (C 1 C 6 ) alkoxy groups, halo (Ci-C,) alkoxy groups, (C1-C) alkyl thio groups, halo (Ci-C 6 ) alkylthio groups, (Ci-C,) alkyl sulfinyl groups, halo (C 1 -C) alkylsulfinyl groups, (Ci C6) alkylsulfonyl groups, halo (C1-C6) alkylsulfonyl groups, mono (C1-CE) alkylamino groups, di (C 1 -C 6 ) alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, and (C1-C) alkoxycarbonyl groups; a phenyl (C1-C4) alkyl group; a substituted phenyl(Ci-C 4 )alkyl group having on the ring one or more substituents which may be the same 109 or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C,) alkyl groups, halo (C-C6) alkyl groups, (Cl-C) alkoxy groups, halo (Cl-C) alkoxy groups, (Cl-C) alkylthio groups, halo (Cl-C6) alkylthio groups, (Cl-C 6 ) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Cl-C) alkylsulfonyl groups, halo (Ci-C 6 ) alkyl sulfonyl groups, mono (Ci-C)alkylamino groups, di(Ci C 6 )alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (C-C,)alkoxycarbonyl groups; a heterocyclic group; or a substitute heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C.) alkyl groups, halo (Cl-C.) alkyl groups, (Cl-CE) alkoxy groups, halo (Cl-C.) alkoxy groups, (Cl-C) alkylthio groups, halo (Cl-C6) alkylthio groups, (Cl-CE) alkylsulfinyl groups, halo (C 1 -C 6 ) alkylsulfinyl groups, (Cl-C 6 ) alkylsulfonyl groups, halo (C 1 -C 6 ) alkyl sulfonyl groups, mono (Ci-C 6 )alkylamino groups, di(C 1 C 6 ) alkylamino groups whose (C 1 -C,)alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups, (ii) in the case of A 4 being -C(=O)- or -C(=NOR) (wherein R is as defined above) , R is a hydrogen atom; a (Ci-C 6 ) alkyl group; a halo (Ci-C 6 ) alkyl group; a (C 2 -C 6 ) alkenyl group; a halo (C 2 -C 6 ) alkenyl group; a (C 3 C 6 ) cycloalkyl group; a halo (C 3 -C 6 ) cycloalkyl group; a (Cl-C 6 ) alkoxy group; a halo (Cl-C.) alkoxy group; a (Cl C 6 )alkylthio group; a halo (C,-C 6 )alkylthio group; a mono (Cl-C 6 ) alkylamino group; a di (Cl-C 6 )alkylamino group 110 whose (C,-C,)alkyl groups may be the same or different; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C 6 ) alkyl groups, halo (C 1 -C 6 ) alkyl groups, (C 1 C 6 ) alkoxy groups, halo (C 1 -C.) alkoxy groups, (Cl-C,) alkyl thio groups, halo (C 1 -C 6 ) alkylthio groups, (Cl-C 6 )alkyl sulfinyl groups, halo (Cl-C.) alkylsulfinyl groups, (C 1 C 6 )alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, mono (C 1 -C 6 ) alkylamino groups, di (Cl-C 6 ) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; a phenylamino group; a substituted phenylamino group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C) alkyl groups, halo (C 1 -C 6 ) alkyl groups, (C 1 C 6 ) alkoxy groups, halo (C 1 -C 6 ) alkoxy groups, (Cl-C 6 ) alkyl thio groups, halo (C 1 -C 6 ) alkylthio groups, (C 1 -C 6 )alkyl sulfinyl groups, halo (C 1 -C 6 ) alkylsulfinyl groups, (Ci C 6 ) alkylsulfonyl groups, halo (C 1 -C.) alkylsulfonyl groups, mono (C 1 -C 6 ) alkylamino groups, di (C 1 -C) alkylamino groups whose (C,-C)alkyl groups may be the same or different, and (C 1 -C 6 ) alkoxycarbonyl groups; a phenyloxy group; a substituted phenyloxy group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C 6 ) alkyl groups, halo (Ci-C) alkyl groups, (C 1 C 6 ) alkoxy groups, halo (C 1 -C 6 ) alkoxy groups, (Cl-C 6 ) alkyl- 111 thio groups, halo (Cl-C,) alkylthio groups, (C 1 -C,) alkyl sulfinyl groups, halo (C 1 -C.) alkylsulfinyl groups, (C, C 6 )alkylsulfonyl groups, halo (Ci-C,) alkylsulfonyl groups, mono (C 1 -C.) alkylamino groups, di (Cl-C 6 ) alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (C-C)alkoxycarbonyl groups; a phenylthio group; a substituted phenylthio group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C 6 ) alkyl groups, halo (C 1 -C.) alkyl groups, (Cl C 6 ) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (C 1 -C 6 ) alkyl thio groups, halo (Cl-C 6 ) alkylthio groups, (Ci-C,) alkyl sulfinyl groups, halo (C 1 -C.) alkylsulfinyl groups, (Cl C 6 )alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, mono (Cl-CE) alkylamino groups, di (C 1 -C 6 ) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Ci-C)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C) alkyl groups, halo (C 1 -C.) alkyl groups, (Cl C 6 ) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (Cl-C 6 ) alkyl thio groups, halo (C 1 -C 6 )alkylthio groups, (Cl-C 6 )alkyl sulfinyl groups, halo(C 1 -C 6 )alkylsulfinyl groups, (C C 6 )alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, mono (C 1 -C) alkylamino groups, di (Ci-C.) alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (Ci-C) alkoxycarbonyl groups)), 112 further, R 2 being able to bind to A' or R to form a 5- to 8-membered ring that may contain one to three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, each of Q1 through Q 5 is a carbon atom or a nitrogen atom, each of Xs, which may be the same or different, is a halogen atom; a cyano group; a nitro group; a (C 3 -C 6 ) cycloalkyl group; a halo (C 3 -C 6 ) cycloalkyl group; a (C1-C 6 )alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more substit uents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C,) alkyl groups, halo (Cl-C) alkyl groups, (Ci C 6 ) alkoxy groups, halo (C-C 6 ) alkoxy groups, (Ci-C,) alkyl thio groups, halo (CI-C 6 ) alkylthio groups, (Cl-C 6 ) alkyl sulfinyl groups, halo (Cl-C.) alkylsulfinyl groups, (C1 C 6 ) alkylsulfonyl groups, halo (C1-C 6 ) alkylsulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di (Cl-C,) alkylamino groups whose (Ci-C,)alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C,-C 6 ) alkyl groups, halo (C1-C 6 ) alkyl groups, (C, C 6 ) alkoxy groups, halo (C1-C 6 ) alkoxy groups, (C,-C) alkyl thio groups, halo (C,-C 6 ) alkylthio groups, (Cl-C 6 )alkyl- 113 sulfinyl groups, halo (Ci-C) alkylsulfinyl groups, (Cl C,)alkylsulfonyl groups, halo (CCC0) alkylsulfonyl groups, mono (C1-C) alkylamino groups, di (C-C) alkylamino groups whose (C-C)alkyl groups may be the same or different, and (C-C) alkoxycarbonyl groups; or -A 5 -R" (wherein A5 is -0-, -S-, -SO-, -502-, -C(=O)-, -C(=NOR1 3 ) (wherein R1 3 is as defined above), a (Cl-C)alkylene group, a halo (C-C6) alkylene group, a (C 2 -C)alkenylene group, a halo (C2-C) alkenylene group, a (C 2 -C)alkynylene group or a halo (C 3 -C) alkynylene group, (1) in the case of A 5 being -0-, -S-, -SO- or -SO 2 -, R' is a halo (C3-C6) cycloalkyl group; a halo (C3 C)cycloalkenyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C,)alkyl groups, halo (C1-C) alkyl groups, (C1-C) alkoxy groups, halo (C C0) alkoxy groups, (C1-C) alkylthio groups, halo (Cl C) alkylthio groups, (CI-C) alkylsulfinyl groups, halo (C-C6) alkylsulfinyl groups, (C-C6) alkylsulfonyl groups, halo (C-C) alkylsulfonyl groups, mono (C C6)alkylamino groups, di (C-C) alkylamino groups 'whose (0,-C6)alkyl groups may be the same or different, and (0,-C6)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C6) alkyl groups, halo (C-C) alkyl groups, (C,- 114 C.) alkoxy groups, halo (C1-C6) alkoxy groups, (C1-C) alkyl thio groups, halo (C1-C) alkylthio groups, (C1-C) alkyl sulfinyl groups, halo (C-C) alkylsulfinyl groups, (Ci C6) alkylsulfonyl groups, halo (C1-C) alkylsulfonyl groups, mono (C1-C) alkylamino groups, di (C1-C6) alkylamino groups whose (C-C)alkyl groups may be the same or different, and (C 1 -C 6 )alkoxycarbonyl groups; or -A-Rl' (wherein A 6 is a (Ci-C)alkylene group, a halo (C 1 -C 6 ) alkylene group, a (C 3 -C 6 )alkenylene group, a halo (C 3 -C 6 )alkenylene group, a (C3-C6) alkynylene group or a halo (C3-C6) alkynylene group, and R" is a hydrogen atom; a halogen atom; a (C3 C0) cycloalkyl group; a halo (C3-C6) cycloalkyl group; a (C 1 -C 6 )alkoxycarbonyl group; a phenyl group; a substi tuted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C C0) alkyl groups, halo (C-C6) alkyl groups, (C-C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C1-C6) alkylthio groups, halo (C-C) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (C-C6) alkylsulfinyl groups, (C-C6) alkyl sulfonyl groups, halo (C1-C6) alkylsulfonyl groups, mono (C1-C6) alkylamino groups, di (C-C6) alkylamino groups whose (C 1 -C)alkyl groups may be the same or different, and (C-C) alkoxycarbonyl groups; or -A'-R 1 6 (wherein A' is -0-, -S-, -SO- or -S02-, and R 6 is a (C-C 6 )alkyl group; a halo (C1-C6) alkyl group; a (C3-C6) alkenyl group; a halo (C3-C6) alkenyl group; a (C3-C) alkynyl group; a halo (C 3 -C 6 )alkynyl group; a (C 3 -C) cycloalkyl group; a 115 halo(C 3 -C 6 )cycloalkyl group; a phenyl group; a substi tuted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C, C 6 ) alkyl groups, halo (Cl-CE) alkyl groups, (Ci-C) alkoxy groups, halo (Cl-C) alkoxy groups, (C,-C) alkylthio groups, halo (C 1 -C 6 ) alkylthio groups, (Cl-C) alkylsulfinyl groups, halo (Cl-C) alkylsulfinyl groups, (C 1 -C,) alkyl sulfonyl groups, halo (Cl-C) alkylsulfonyl groups, mono (Cl-C) alkylamino groups, di (Cl-C 6 ) alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (C-C)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C) alkyl groups, halo (C-C6) alkyl groups, (Cl CE) alkoxy groups, halo (C-C6) alkoxy groups, (C 1 -C,) alkyl thio groups, halo (Cl-C) alkylthio groups, (Ci-C 6 ) alkyl sulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Ci C6)alkylsulfonyl groups, halo (C 1 -C 6 )alkylsulfonyl groups, mono (Cl-C) alkylamino groups, di (Cl-C) alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (Cl-C) alkoxycarbonyl groups), (2) in the case of A 5 being -C(=O)- or -C(=NOR 3 ) - (wherein R 3 is as defined above), R" is a (Cl-C) alkyl group; a halo (Cl-CE) alkyl group; a (C2 CE) alkenyl group; a halo (C2-C) alkenyl group; a (C3 C) cycloalkyl group; a halo (C3-C) cycloalkyl group; a 116 (Cl-C 6 ) alkoxy group; a (C 1 -C,) alkylthio group; a mono (Cl C,) alkylamino group; a di(C 1 -C 6 )alkylamino group whose (C,-C 6 )alkyl groups may be the same or different; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 ) alkyl groups, halo (Cl-C 6 ) alkyl groups, (C 1 C.) alkoxy groups, halo (Cl-C) alkoxy groups, (C 1 -C 6 ) alkyl thio groups, halo (Ci-C 6 ) alkylthio groups, (C 1 -C 6 ) alkyl sulfinyl groups, halo (C 1 -C 6 )alkylsulfinyl groups, (Cl C6)alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, mono (Ci-C 6 ) alkylamino groups, di (C 1 -C.) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (C-C)alkoxycarbonyl groups; a phenylamino group; a substituted phenylamino group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 ) alkyl groups, halo (Ci-C 6 ) alkyl groups, (C 1 C.) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (Ci-C 6 ) alkyl thio groups, halo (Cl-C 6 ) alkylthio groups, (C 1 -C 6 ) alkyl sulfinyl groups, halo (C 1 -C.) alkylsulfinyl groups, (Ci C 6 ) alkylsulfonyl groups, halo (Ci-C 6 ) alkylsulfonyl groups, mono (C 1 -C 6 ) alkylamino groups, di (Ci-C 6 ) alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (C-C)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, 117 (C 1 -C 6 ) alkyl groups, halo (C 1 -C 6 ) alkyl groups, (Ci C.) alkoxy groups, halo (C 1 -C 6 ) alkoxy groups, (Ci-C,) alkyl thio groups, halo (Cl-C.) alkylthio groups, (Cl-C) alkyl sulfinyl groups, halo (Ci-C 6 ) alkylsulfinyl groups, (C1 C 6 ) alkylsulfonyl groups, halo (C 1 -C 6 ) alkylsulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di (Cl-C 6 ) alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (C 1 -C,)alkoxycarbonyl groups, (3) in the case of A 5 being a (Cl-C,)alkylene group, a halo (C 1 -C 6 ) alkylene group, a (C 2 -C 6 )alkenylene group, a halo (C 2 -C,) alkenylene group, a (C 2 -C 6 )alkynylene group or a halo (C 3 -C 6 ) alkynylene group, R" is a hydrogen atom; a halogen atom; a (C 3 -C 6 )cycloalkyl group; a halo (C 3 -C 6 ) cycloalkyl group; a (C 1 -C,) alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 )alkyl groups, halo (Cl-C.) alkyl groups, (Ci-C 6 ) alkoxy groups, halo (Ci-C.) alkoxy groups, (Ci-C 6 ) alkylthio groups, halo (C 1 -C.) alkylthio groups, (CI-C,) alkylsulfinyl groups, halo (C 1 -C 6 ) alkylsulfinyl groups, (Ci-C,) alkylsulfonyl groups, halo (Cl-C 6 ) alkyl sulfonyl groups, mono (Cl-C) alkylamino groups, di(Cl C 6 ) alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano 118 group, nitro group, (Ci-C) alkyl groups, halo (Ci-C 6 ) alkyl groups, (Cl-C.) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (C 1 -C.) alkylthio groups, (Ci-C 6 ) alkylsulfinyl groups, halo (Ci-C 6 ) alkylsulfinyl groups, (Ci-C 6 ) alkylsulfonyl groups, halo (Ci-C 6 ) alkyl sulfonyl groups, mono (Ci-C 6 )alkylamino groups, di(Cl C 6 ) alkylamino groups whose (Ci-C,)alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; or -A 8 -R 7 (wherein A' is -0-, -S-, -SO- or -S02-, and R" is a (C 3 -C,) cycloalkyl group; a halo (C 3 -C 6 ) cycloalkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 ) alkyl groups, halo (Cl-C 6 ) alkyl groups, (C 1 C 6 ) alkoxy groups, halo (Cl-C.) alkoxy groups, (Cl-C,) alkyl thio groups, halo (Ci-C.) alkylthio groups, (Ci-C) alkyl sulfinyl groups, halo (C 1 -C 6 ) alkylsulfinyl groups, (Cl C 6 ) alkylsulfonyl groups, halo (Ci-C,) alkylsulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di (C 1 -C 6 ) alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (Ci-C)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 ) alkyl groups, halo (Ci-C 6 ) alkyl groups, (Cl C0) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (Cl-C 6 ) alkyl thio groups, halo (Cl-C 6 )alkylthio groups, (Cl-C,)alkyl sulfinyl groups, halo (Ci-C.) alkylsulfinyl groups, (C 1 - -119 C 6 ) alkylsulfonyl groups, halo (C 1 -C 6 ) alkylsulfonyl groups, mono (Cl-C.) alkylamino groups, di (Ci-C.) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C 6 ) alkoxycarbonyl groups; or -A 9 -R" (wherein A 9 is a (C-C 6 )alkylene group, a halo (C 1 -C 6 )alkylene group, a (C 2 -C 6 ) alkenylene group, a halo (C 2 -C 6 ) alkenylene group, a (C 2 -C 6 ) alkynylene group or a halo (C 3 -C 6 ) alkynylene group, and R" is a hydrogen atom; a halogen atom; a (C 3 C 6 ) cycloalkyl group; a halo (C 3 -C) cycloalkyl group; a (Cl-C 6 ) alkoxy group; a halo (C 1 -C 6 ) alkoxy group; a (C 1 C 6 ) alkylthio group; a halo (C 1 -C.) alkylthio group; a (C 1 C 6 ) alkylsulfinyl group; a halo (C 1 -C 6 ) alkylsulfinyl group; a (C 1 -C,) alkylsulfonyl group; a halo (C 1 -C 6 ) alkylsulfonyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 ) alkyl groups, halo (Cl-C 6 ) alkyl groups, (C 1 -C 6 ) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (C 1 -C 6 ) alkylthio groups, (Cl-C,) alkylsulfinyl groups, halo (C 1 -C.) alkylsulfinyl groups, (Cl-C 6 ) alkylsulfonyl groups, halo (C 1 -C 6 ) alkyl sulfonyl groups, mono (Cl-C 6 )alkylamino groups, di(Cl C) alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups; a phenyloxy group; a substituted phenyloxy group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C,)alkyl groups, halo (Cl-C 6 )alkyl 120 groups, (C 1 -C.) alkoxy groups, halo (C 1 -C 6 ) alkoxy groups., (C 1 -C 6 ) alkylthio groups, halo (C-C6) alkylthio groups, ((1-C6)alkylsulfinyl groups, halo (Cl-C) alkylsulfinyl groups, (C1-C) alkylsulfonyl groups, halo (C-C) alkyl sulfonyl groups, mono(Cl-C 6 )alkylamino groups, di(C 1 C6)alkylamino groups whose (C-C)alkyl groups may be the same or different, and (C 1 -C)alkoxycarbonyl groups; a phenylthio group; a substituted phenylthio group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C,-C,)alkyl groups, halo (C 1 -C 6 ) alkyl groups, (C 1 -C 6 ) alkoxy groups, halo (Cl-C) alkoxy groups, (Cl-C)alkylthio groups, halo (Cl-C) alkylthio groups, (Cl-C6) alkylsulfinyl groups, halo (Cl-C) alkylsulfinyl groups, (Cl-C 6 ) alkylsulfonyl groups, halo (C 1 -C 6 ) alkyl sulfonyl groups, mono(C-C 6 )alkylamino groups, di(C, C 6 )alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (C 1 -C,)alkoxycarbonyl groups; a heterocyclic group; or a heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C,-C) alkyl groups, halo (Cl-C 6 ) alkyl groups, (C 1 C6) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (Cl-C 6 ) alkyl thio groups, halo (Ci-C 6 ) alkylthio groups, (C 1 -C 6 ) alkyl sulfinyl groups, halo (Ci-C 6 ) alkylsulfinyl groups, (C 1 CE)alkylsulfonyl groups, halo (Cl-C) alkylsulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di (Cl-C.) alkylamino groups whose (Cl-C)alkyl groups may be the same or different, 121 and (Ci-C 6 )alkoxycarbonyl groups)), n is an integer of 0 to 4, further, two adjacent Xs on the aromatic ring being able to be taken together to represent a fused ring that may have one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 )alkyl groups, halo (Cl-C 6 ) alkyl groups, (C 1 -C 6 ) alkoxy groups, halo (Cl C) alkoxy groups, (C-C) alkylthio groups, halo (Cl C6) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (Cl-CE) alkylsulfinyl groups, (Cl-C) alkylsulfonyl groups, halo (Cl-C6) alkylsulfonyl groups, mono (C, C,) alkylamino groups, di (Cl-C 6 ) alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, and (Cl-C6) alkoxycarbonyl groups, each of Ys, which may be the same or different, is a halogen atom; a cyano group; a nitro group; a (C 3 -C 6 ) cycloalkyl group; a halo (C3-C) cycloalkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C) alkyl groups, halo (Cl-C6) alkyl groups, (Cl-C.) alkoxy groups, halo (Cl-C) alkoxy groups, (Cl-C6) alkylthio groups, halo (C 1 -C 6 ) alkylthio groups, (Cl-C) alkylsulfinyl groups, halo (Cl-C.) alkylsulfinyl groups, (Cl-C 6 ) alkylsulfonyl groups, halo (C 1 -C 6 ) alkyl sulfonyl groups, mono (Ci-C 6 ) alkylamino groups, di (C 1 CE) alkylamino groups whose (Cl-C 6 )alkyl groups may be -the 122 same or different, and (C 1 -C,)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C.) alkyl groups, halo (C 1 -C 6 ) alkyl groups, (Cl-C6) alkoxy groups, halo (C 1 -C.) alkoxy groups, (Cl-C6) alkylthio groups, halo (Cl-C6) alkylthio groups, (Cl-C6) alkylsulfinyl groups, halo (Ci-C) alkylsulfinyl groups, (Cl-C 6 ) alkylsulfonyl groups, halo (Ci-C,) alkyl sulfonyl groups, mono (C 1 -C 6 )alkylamino groups, di(Ci C 6 )alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; or -A-R" (wherein A 5 and R' are as defined above), further, two adjacent Ys on the aromatic ring being able to be taken together to represent a fused ring that may have one or more substituents which may be the same or different and are selected from halogen atoms; (Cl-CE) alkyl groups; halo (C 1 -C 6 ) alkyl groups; (Cl C6) alkoxy groups; halo (Ci-C 6 ) alkoxy groups; (Cl-C) alkyl thio groups; halo (Cl-C.) alkylthio groups; (Cl-C) alkyl sulfinyl groups; halo (Cl-C 6 )alkylsulfinyl groups; (Ci C6)alkylsulfonyl groups; halo (Cl-C6)alkylsulfonyl groups; phenyl group; substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C1-C6) alkyl groups, halo (Cl-C.) alkyl groups, (Cl C6) alkoxy groups, halo (C-C6) alkoxy groups, (C-C6) alkyl thio groups, halo (C 1 -C 6 )alkylthio groups, (C-C 6 )alkyl- 123 sulfinyl groups, halo (C1-C.) alkylsulfinyl groups, (Cl C,) alkylsulfonyl groups, halo (Cl-C.) alkylsulfonyl groups, mono (Ci-C 6 ) alkylamino groups, di (C-C) alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (Ci-C)alkoxycarbonyl groups; heterocyclic groups; and substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 ) alkyl groups, halo (Cl-C) alkyl groups, (Ci C 6 ) alkoxy groups, halo (C-C,) alkoxy groups, (Cl-C,) alkyl thio groups, halo (Cl-C.) alkylthio groups, (Ci-C)alkyl sulfinyl groups, halo (C,-C 6 ) alkylsulfinyl groups, (Ci C 6 ) alkylsulfonyl groups, halo (Ci-C.) alkylsulfonyl groups, mono (Ci-C 6 ) alkylamino groups, di (C1-C) alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (Ci-C 6 )alkoxycarbonyl groups, m is an integer of 1 to 5, and each of Z' and Z2 is an oxygen atom or a sulfur atom} or a salt thereof. 2. An aromatic diamide derivative or a salt thereof according to claim 1, wherein A' is a (Cl C,)alkylene group; a substituted (Ci-C)alkylene group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo (Cl-C 6 ) alkyl groups, (C, C 6 ) alkoxy groups, halo (C-C) alkoxy groups, (C-C) alkyl thio groups, halo (C1-C.) alkylthio groups, (Cl-C) alkyl sulfinyl groups, halo (Ci-C 6 ) alkylsulfinyl groups, (C,- 124 C 6 )alkylsulfonyl groups, halo (Cl-C 6 ) alkylsulfonyl groups, (Cl-C) alkylthio (Cl-C 6 ) alkyl groups, (C 1 -C,) alkoxycarbonyl groups and phenyl group; a (C 3 -C)alkenylene group; a substituted (C 3 -C,)alkenylene group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo (C 1 -C 6 ) alkyl groups, (C 1 -C,) alkoxy groups, halo (C 1 C 6 ) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (Ci C6)alkylthio groups, (Cl-C 6 )alkylsulfinyl groups, halo (Ci-C 6 )alkylsulfinyl groups, (C-C,)alkylsulfonyl groups, halo (Cl-C.) alkylsulfonyl groups, (Cl-C 6 ) alkyl thio (C 1 -C 6 ) alkyl groups, (C 1 -C 6 ) alkoxycarbonyl groups and phenyl group; a (C 3 -C)alkynylene group; or a substi tuted (C 3 -C)alkynylene group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo (C 1 -C) alkyl groups, (C 1 -C 6 ) alkoxy groups, halo (C 1 C.) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (C 1 C 6 )alkylthio groups, (Cl-C 6 )alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (C 1 -C 6 ) alkylsulfonyl groups, halo (Cl-C 6 ) alkylsulfonyl groups, (Ci-C 6 ) alkyl thio (C 1 -C 6 ) alkyl groups, (Cl-C 6 ) alkoxycarbonyl groups and phenyl group, any of the saturated carbon atoms in the above-mentioned (C 1 -C)alkylene group, substituted (C 1 C 8 ) alkylene group, (C 3 -C)alkenylene group, substituted (C 3 -C) alkenylene group, (C 3 -C) alkynylene group or substituted (C 3 -C)alkynylene group being able to have a 125 (C 2 -C 5 )alkylene group bonded thereto as a substituent, to form a (C 3 -C 6 )cycloalkane ring, and any two of the carbon atoms in the above-mentioned (C,-C.)alkylene group, substituted (C 1 -C.) alkylene group, (C 3 C)alkenylene group and substituted (C 3 -C)alkenylene group being able to form a (C 3 -C,)cycloalkane ring or a (C 3 -Cs)cycloalkene ring together with an alkylene group or an alkenylene group, B is -0- or -N(R 4 )- (wherein R 4 is a hydrogen atom; a (Cl-C 6 ) alkyl group; a halo (C 1 -C.) alkyl group; a (C 3 -C 6 ) alkenyl group; a halo (C 3 -C,) alkenyl group; a (C 3 C6) alkynyl group; a (C 3 -C) cycloalkyl group; a (Cl C,)alkylcarbonyl group; a halo(Cl-C)alkylcarbonyl group; a (C-C,)alkoxycarbonyl group; a phenylcarbonyl group; a substituted phenylcarbonyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C) alkyl groups, halo (C 1 -C 6 ) alkyl groups, (C 1 C 6 ) alkoxy groups, halo (Cl-C.) alkoxy groups, (Cl-C 6 ) alkyl thio groups, halo (Cl-C) alkylthio groups, (Ci-C.) alkyl sulfinyl groups, halo (Cl-C.) alkylsulfinyl groups, (Ci C 6 )alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, mono (Cl-C 6 ) alkylamino groups, and di (C 1 -C.) alkylamino groups whose (Cl-C)alkyl groups may be the same or different; a phenyl(Cl-C 4 )alkoxycarbonyl group; a substituted phenyl(Cl-C 4 )alkoxycarbonyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano 126 group, nitro group, (Cl-C 6 ) alkyl groups, halo (C 1 -C 6 ) alkyl groups, (Ci-C 6 ) alkoxy groups, halo (CI-C 6 ) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (Cl-CE) alkylthio groups, (C 1 -C 6 ) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Cl-C 6 ) alkylsulfonyl groups, halo (Cl-C) alkyl sulfonyl groups, mono(Cl-C)alkylamino groups, and di(Cl C)alkylamino groups whose (Cl-C,)alkyl groups may be the same or different; a phenyl(Cl-C 4 )alkyl group; or a substituted phenyl(Cl-C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 ) alkyl groups, halo (Cl-C6)alkyl groups, (Cl-C) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (CI-C 6 ) alkylthio groups, halo (Ci-C.) alkylthio groups, (Cl-C 6 ) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Cl-C) alkylsulfonyl groups, halo (Cl-C) alkyl sulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di(Ci CE)alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups), R1 is a hydrogen atom; a (Ci-C)alkyl group; a halo (Cl-C) alkyl group; a (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl group; a (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl group; a (C 2 CE) alkenyl group; a halo (C 2 -C6) alkenyl group; a (C 3 C6)alkynyl group; a halo (C 3 -C 6 ) alkynyl group; a (C 3 CE) cycloalkyl group; a halo (C 3 -CE) cycloalkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro 127 group, (C 1 -C) alkyl groups, halo (C,-C,) alkyl groups, (C 1 C.) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (C 1 -C 6 ) alkyl thio groups, halo (Ci-C) alkylthio groups, (C 1 -C.) alkyl sulfinyl groups, halo (C 1 -C 6 )alkylsulfinyl groups, (C, C 6 ) alkylsulfonyl groups, halo (C 1 -C 6 ) alkylsulfonyl groups, mono (C 1 -C) alkylamino groups, di (Cl-C.) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C 6 ) alkoxycarbonyl groups; a phenyl (Cl-C 4 ) alkyl group; a substituted phenyl(Cl-C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C)alkyl groups, halo (Ci-C 6 ) alkyl groups, (Cl-C) alkoxy groups, halo (Ci-C.) alkoxy groups, (Cl-C) alkylthio groups, halo (Cl-C.) alkylthio groups, (Cl-C 6 ) alkylsulfinyl groups, halo (Cl-C) alkylsulfinyl groups, (C 1 -C 6 ) alkylsulfonyl groups, halo (Cl-C 6 ) alkyl sulfonyl groups, mono (C 1 -C.) alkylamino groups, di(Cl C 6 ) alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (Ci-C 6 )alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 ) alkyl groups, halo (Cl-C) alkyl groups, (C 1 -C 6 ) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (C 1 -C 6 ) alkylthio groups, halo (Cl-C 6 ) alkylthio groups, (C 1 -C 6 ) alkylsulfinyl groups, halo (Ci-C 6 ) alkylsulfinyl groups, (Cl-C 6 ) alkylsulfonyl groups, halo (Cl-C 6 ) alkyl sulfonyl groups, mono (Cl-C) alkylamino groups, di(Cl- 128 C 6 ) alkylamino groups whose (Ci-C.) alkyl groups may be the same or different, and (Ci-C 6 )alkoxycarbonyl groups; -P (=W) (-OR') (-OR 6 ) (wherein W1 is an oxygen atom or a sulfur atom, and each of R' and R 6 , which may be the same or different, is a hydrogen atom; a (C 1 -C,)alkyl group; a halo (Cl-C 6 ) alkyl group; a (C 1 -C 4 ) alkoxy (Ci C 4 )alkyl group; a (C 1 -C 4 )alkylthio (C 1 -C 4 )alkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C 6 ) alkyl groups, halo (Cl-C 6 ) alkyl groups, (Ci C.) alkoxy groups, halo (C-C6) alkoxy groups, (Ci-C 6 ) alkyl thio groups, halo (Cl-C) alkylthio groups, (Ci-C) alkyl sulfinyl groups, halo (C,-C 6 )alkylsulfinyl groups, (C 1 C 6 ) alkylsulfonyl groups, halo (Cl-C) alkylsulfonyl groups, mono (Ci-C.) alkylamino groups, di (Cl-C 6 ) alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (Cl-C.) alkoxycarbonyl groups; a phenyl (C 1 -C 4 ) alkyl group; a substituted phenyl (Cl-C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C.) alkyl groups, halo (Cl-C 6 )alkyl groups, (Cl-C.) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (C 1 -C 6 ) alkylthio groups, (CI-C 6 ) alkylsulfinyl groups, halo (C 1 -C 6 ) alkylsulfinyl groups, (C 1 -C 6 ) alkylsulfonyl groups, halo (Cl-C 6 ) alkyl sulfonyl groups, mono (Cl-C 6 )alkylamino groups, di(C 1 C 6 ) alkylamino groups whose (Cl-C 6 )alkyl groups may be the 129 same or different, and (Cl-C,)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C.) alkyl groups, halo (Cl-C 6 ) alkyl groups, (Cl-C.) alkoxy groups, halo (Cl-C.) alkoxy groups, (Cl-C6) alkylthio groups, halo (Cl-C.) alkylthio groups, (Ci-C 6 ) alkylsulfinyl groups, halo (C-C) alkylsulfinyl groups, (Cl-CE) alkylsulfonyl groups, halo (Cl-C 6 ) alkyl sulfonyl groups, mono (Cl-C.) alkylamino groups, di(Cl C 6 )alkylamino groups whose (C-C,)alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups, R' being able to bind to R 6 to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); -C(=W')-N(R 5 ) (R 6 ) (wherein W', R 5 and R 6 are as defined above, R 5 being able to bind to R 6 to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, and R 5 being able to bind to R 4 to form a 5- to 8 membered ring that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); -C(=Wl)-R 5 (wherein W1 and R5 are as defined above); -C(=W)-W-R' 130 (wherein W's, which may be the same or different, are as defined above, and R' is a (C 1 -C 6 )alkyl group; a halo (C, C 6 ) alkyl group; a (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl group; a (Cl C 4 )alkylthio (C 1 -C 4 )alkyl group; a phenyl group; a substituted phenyl group having one or more substit uents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 ) alkyl groups, halo (Cl-C.) alkyl groups, (Cl C 6 ) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (Cl-C6) alkyl thio groups, halo (Ci-C)alkylthio groups, (Cl-C 6 )alkyl sulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Ci C0) alkylsulfonyl groups, halo (C 1 -C 6 ) alkylsulfonyl groups, mono (C1-C6) alkylamino groups, di (Cl-C 6 ) alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (C 1 -C 6 ) alkoxycarbonyl groups; a phenyl (C 1 -C 4 ) alkyl group; a substituted phenyl (Cl-C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 )alkyl groups, halo(Cl-C 6 )alkyl groups, (Cl-C6) alkoxy groups, halo (Cl-C.) alkoxy groups, (C 1 -C 6 ) alkylthio groups, halo (Cl-C 6 ) alkylthio groups, (Cl-C 6 ) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (Cl-C6) alkylsulfonyl groups, halo (C-C6) alkyl sulfonyl groups, mono (Cl-CE) alkylamino groups, di (Ci CE) alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (C 1 -C)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same 131 or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C6) alkyl groups, halo (C1-C) alkyl groups, (Ci-C,) alkoxy groups, halo (C1-C6) alkoxy groups, (Cl-Cs) alkylthio groups, halo (Cl-C.) alkylthio groups, (C1-C6) alkylsulfinyl groups, halo (Cl-C) alkylsulfinyl groups, (Cl-C6) alkylsulfonyl groups, halo (Ci-C.) alkyl sulfonyl groups, mono(Cl-C.)alkylamino groups, di(Cl C 6 )alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups); -SO 2 -R7 (wherein R' is as defined above); -S0 2 -N (R') (R 6 ) (wherein R 5 and R 6 are as defined above, R 5 being able to bind to R 6 to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, and R 5 being able to bind to R 4 to form a 5- to 8-membered ring that may contain three or four atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); -N(R 5 ) (R 6 ) (wherein R 5 and R 6 are as defined above, R 5 being able to bind to R 6 to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, and R' being able to bind to R 4 to form a 5- to 8-membered ring that may contain two or three atoms which may be the same or different 132 and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms consti tuting the ring); or -N=C(R')R5 (wherein R' and R' are as defined above, R 5 being able to bind to R 6 to form a 5 to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); in the case of B being -N(R 4 )- (wherein R 4 is as defined above), R' being able to be -OR' (wherein R 5 is as defined above), -C (W 2 ) -N(R 5 )R 6 (wherein W 2 is =CH-N0 2 , =N-N0 2 or =N-CN, and R 5 and R 6 are as defined above, R 5 or R 6 being able to bind to R 4 to form a 5- to 8-membered ring that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring) or -C(W2)-W'-R' (wherein W1, W 2 and R' are as defined above, R 7 being able to bind to R 4 to form a 5- to 8-membered ring that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring), and R' being able to bind to A' to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, 133 each of R 2 and R 3 , which may be the same or different, is a hydrogen atom or a (C 1 -C 3 )alkyl group, each of Q' through Q' is a carbon atom or a nitrogen atom, each of Xs, which may be the same or different, is a halogen atom, a nitro group, a (Cl-C,)alkyl group, a halo (Cl-C.) alkyl group, a (C 2 -C)alkenyl group, a halo (C 2 -C6)alkenyl group, a (C 2 -C,)alkynyl group, a halo (C 2 -C 6 ) alkynyl group, a (C 1 -C,) alkoxy group, a halo (Cl-C.) alkoxy group, a (C 1 -C,) alkylthio group, a halo (C 1 -C 6 ) alkylthio group, a (C 1 -C 6 ) alkylsulfinyl group, a halo (C 1 -C 6 ) alkylsulfinyl group, a (Cl-C 6 ) alkylsulfonyl group or a halo (Cl-C 6 )alkylsulfonyl group, two adjacent Xs on the aromatic ring being able to be taken together to represent a fused ring that may have one or more substituents which may be the same or different and are selected from halogen atoms, nitro group, (Cl-C,) alkyl groups, halo (C,-C.) alkyl groups, (Cl-C 6 ) alkoxy groups, halo (Cl-C) alkoxy groups, (Cl-C,) alkylthio groups, halo (Cl-CE) alkylthio groups, (C 1 -C 6 ) alkylsulfinyl groups, halo (C 1 -C 6 ) alkylsulfinyl groups, (Cl-C,) alkylsulfonyl groups and halo (Cl-C) alkyl sulfonyl groups, n is an integer of 0 to 2, each of Ys, which may be the same or different, is a halogen atom; a cyano group; a nitro group; a (C 3 -C 6 ) cycloalkyl group; a halo (C 3 -C,) cycloalkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano 134 group, nitro group, (Ci-C 6 ) alkyl groups, halo (Cl-C 6 ) alkyl groups, (Cl-CE) alkoxy groups, halo (Cl-C) alkoxy groups, (C 1 -C 6 ) alkylthio groups, halo (Cl-CE) alkylthio groups, (Cl-C,) alkylsulfinyl groups, halo (Cl-C) alkylsulfinyl groups, (C 1 -C 6 ) alkylsulfonyl groups, halo (C 1 -C.) alkyl sulfonyl groups, mono (Ci-C 6 )alkylamino groups, di(Cl C 6 )alkylamino groups whose (Cl-C6)alkyl groups may be the same or different, and (C,-C 6 )alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 )alkyl groups, halo (Ci-C.) alkyl groups, (C 1 -C 6 ) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (C 1 -C 6 ) alkylthio groups, halo (C 1 -C 6 ) alkylthio groups, (C 1 -C 6 ) alkylsulfinyl groups, halo (C 1 -C 6 ) alkylsulfinyl groups, (Cl-C 6 ) alkylsulfonyl groups, halo (Ci-C.) alkyl sulfonyl groups, mono (C 1 -C.) alkylamino groups, di(Cl C 6 )alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; or -A 5 -R" (wherein A' and R are as defined above), two adjacent Ys on the aromatic ring being able to be taken together to represent a fused ring that may have one or more substituents which may be the same or different and are selected from halogen atoms; (C 1 -C 6 ) alkyl groups; halo (Cl-C 6 ) alkyl groups; (Ci C 6 ) alkoxy groups; halo (Ci-C) alkoxy groups; (Cl-C.) alkyl thio groups; halo (Cl-C 6 )alkylthio groups; (Cl-C 6 )alkyl sulfinyl groups; halo (Cl-C 6 ) alkylsulfinyl groups; (C 1 - 135 C,)alkylsulfonyl groups; halo (C-C6) alkylsulfonyl groups; phenyl group; substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C-C6) alkyl groups, halo (Ci-C) alkyl groups, (C 1 C6) alkoxy groups, halo (C1-C6) alkoxy groups, (C1-C) alkyl thio groups, halo (C 1 -C 6 )alkylthio groups, (C 1 -C 6 )alkyl sulfinyl groups, halo (C 1 -C 6 ) alkylsulfinyl groups, (C1 C6)alkylsulfonyl groups, halo (C 1 -C 6 ) alkylsulfonyl groups, mono (C-C6) alkylamino groups, di (C 1 -C 6 ) alkylamino groups whose ((l-C 6 )alkyl groups may be the same or different, and (C-C)alkoxycarbonyl groups; heterocyclic groups; and substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C1-C6) alkyl groups, halo (C1-C6) alkyl groups, (Cl C6) alkoxy groups, halo (C-C6) alkoxy groups, (C1-C6) alkyl thio groups, halo (C-C) alkylthio groups, (C-C6) alkyl sulfinyl groups, halo (C-C6) alkylsulfinyl groups, (Ci C6)alkylsulfonyl groups, halo (C1-(6) alkylsulfonyl groups, mono (C1-C6) alkylamino groups, di (C1-C6) alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and ((-C)alkoxycarbonyl groups, m is an integer of 1 to 5, and each of Z' and Z 2 is an oxygen atom or a sulfur atom. 3. An aromatic diamide derivative or a salt thereof according to claim 2, wherein A' is a (C C)alkylene group; a substituted (C-C)alkylene group 136 having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo (Cl-C,) alkyl groups, (Cl C0) alkoxy groups, halo (Ci-C.) alkoxy groups, (Ci-C.) alkyl thio groups, halo (Cl-C 6 )alkylthio groups, (C-C 6 )alkyl sulfinyl groups, halo (Cl-CE) alkylsulfinyl groups, (C C6) alkylsulfonyl groups, halo (Cl-C6) alkylsulfonyl groups, (Cl-C) alkylthio (Ci-C 6 ) alkyl groups, (C 1 -C,) alkoxycarbonyl groups and phenyl group; a (C 3 -C)alkenylene group; a substituted (C 3 -C)alkenylene group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo (C 1 -C 6 ) alkyl groups, (C1-C6) alkoxy groups, halo (Ci C6) alkoxy groups, (Cl-C) alkylthio groups, halo (C 1 C 6 ) alkylthio groups, (Cl-C 6 )alkylsulfinyl groups, halo (Ci-C,) alkylsulfinyl groups, (C 1 -C,) alkylsulfonyl groups, halo (C 1 -C 6 ) alkylsulfonyl groups, (Ci-C 6 ) alkyl thio (Cl-C) alkyl groups, (Cl-C 6 ) alkoxycarbonyl groups and phenyl group; a (C 3 -C)alkynylene group; or a substi tuted (C 3 -C)alkynylene group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo (Cl-C) alkyl groups, (C1-C6) alkoxy groups, halo (C1 C6) alkoxy groups, (C1-C6) alkylthio groups, halo (Cl C) alkylthio groups, (Cl-C) alkylsulfinyl groups, halo (Cl-C6) alkylsulfinyl groups, (Cl-C6) alkylsulfonyl groups, halo (Cl-C6) alkylsulfonyl groups, (Cl-C6) alkyl thio (Cl-C 6 )alkyl groups, (Cl-C 6 )alkoxycarbonyl groups and 137 phenyl group, any of the saturated carbon atoms in the above-mentioned (Cl-C)alkylene group, substituted (Cl C 8 ) alkylene group, (C 3 -C)alkenylene group, substituted (C 3 -C 8 ) alkenylene group, (C 3 -C 8 ) alkynylene group or substituted (C 3 -C)alkynylene group being able to have a (C 2 -C 5 )alkylene group bonded thereto as a substituent, to form a (C 3 -C,)cycloalkane ring, and any two of the carbon atoms in the above-mentioned (C 1 -C)alkylene group, substituted (C 1 -C) alkylene group, (C3 C) alkenylene group and substituted (C 3 -C)alkenylene group being able to form a (C 3 -C 6 )cycloalkane ring or a (C 3 -C 6 )cycloalkene ring together with an alkylene group or an alkenylene group, B is -0- or -N(R 4 )- (wherein R 4 is a hydrogen atom; a (C 1 -C 6 ) alkyl group; a halo (C1-C) alkyl group; a (C 3 -C 6 ) alkenyl group; a halo (C 3 -C 6 ) alkenyl group; a (C3 C 6 ) alkynyl group; a (C3-C6) cycloalkyl group; a (Cl C6)alkylcarbonyl group; a halo (C-C6)alkylcarbonyl group; a (C-C,)alkoxycarbonyl group; a phenylcarbonyl group; a substituted phenylcarbonyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C) alkyl groups, halo (Cl-C6) alkyl groups, (Ci C.) alkoxy groups, halo (C1-C6) alkoxy groups, (C-C6) alkyl thio groups, halo (Ci-C) alkylthio groups, (C1-C6) alkyl sulfinyl groups, halo (C-C6) alkylsulfinyl groups, (Ci C6)alkylsulfonyl groups, halo (Cl-C) alkylsulfonyl groups, 138 mono (Cl-C.) alkylamino groups, and di (Cl-C) alkylamino groups whose (Cl-C.) alkyl groups may be the same or different; a phenyl(C 1 -C 4 )alkoxycarbonyl group; a substituted phenyl(C 1 -C 4 )alkoxycarbonyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 )alkyl groups, halo(C 1 -C 6 )alkyl groups, (Cl-C) alkoxy groups, halo (C-C6) alkoxy groups, (C,-C 6 ) alkylthio groups, halo (Cl-CE) alkylthio groups, (Cl-C) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (C,-C 6 ) alkylsulfonyl groups, halo (C 1 -C 6 ) alkyl sulfonyl groups, mono (Cl-C.) alkylamino groups, and di(Cl C,)alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different; a phenyl(C 1 -C 4 )alkyl group; or a substituted phenyl(C 1 -C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C,) alkyl groups, halo (Cl-C6) alkyl groups, (Cl-C) alkoxy groups, halo (C 1 -C.) alkoxy groups, (Cl-C) alkylthio groups, halo (Cl-C 6 ) alkylthio groups, (Cl-C) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (C 1 -C 6 ) alkylsulfonyl groups, halo (Cl-C) alkyl sulfonyl groups, mono (C 1 -C 6 )alkylamino groups, di(Cl CE) alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups), R is a hydrogen atom; a (Ci-C6)alkyl group; a halo (Cl-C 6 ) alkyl group; a (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl group; a (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl group; a (C 2 - 139 C.) alkenyl group; a halo (C 2 -C,) alkenyl group; a (C 3 C 6 ) alkynyl group; a halo (C 3 -C 6 ) alkynyl group; a (C 3 C,)cycloalkyl group; a halo (C 3 -C 6 ) cycloalkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (CI-C) alkyl groups, halo (Cl-C) alkyl groups, (Cl C.) alkoxy groups, halo (Cl-C) alkoxy groups, (Ci-C) alkyl thio groups, halo (Ci-C)alkylthio groups, (Ci-C 6 )alkyl sulfinyl groups, halo (C 1 -C 6 )alkylsulfinyl groups, (Cl C 6 )alkylsulfonyl groups, halo (Ci-C 6 )alkylsulfonyl groups, mono (Cl-C 6 ) alkylamino groups, di (C 1 -C 6 ) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C 6 ) alkoxycarbonyl groups; a phenyl (C 1 -C 4 ) alkyl group; a substituted phenyl(C-C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 )alkyl groups, halo(C 1 -C 6 )alkyl groups, (Ci-C 6 ) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (Cl-C 6 ) alkylthio groups, (C 1 -C 6 ) alkylsulfinyl groups, halo (C 1 -C 6 ) alkylsulfinyl groups, (Cl-C 6 ) alkylsulfonyl groups, halo (Ci-C.) alkyl sulfonyl groups, mono (Ci-C 6 )alkylamino groups, di(Cl C 6 )alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano 140 group, nitro group, (Ci-C 6 ) alkyl groups, halo (C 1 -C 6 ) alkyl groups, (Cl-C 6 ) alkoxy groups, halo (C 1 -C 6 ) alkoxy groups, (C 1 -C 6 ) alkylthio groups, halo (C 1 -C 6 ) alkylthio groups, (C 1 -C 6 ) alkylsulfinyl groups, halo (Cl-C 6 ) alkylsulfinyl groups, (C 1 -C 6 ) alkylsulfonyl groups, halo (Ci-C.) alkyl sulfonyl groups, mono(C-C.)alkylamino groups, di(Cl C 6 )alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Ci-C)alkoxycarbonyl groups; -P(=W) (-OR') (-OR') (wherein W1 is an oxygen atom or a sulfur atom, and each of R 5 and R 6 , which may be the same or different, is a hydrogen atom; a (C 1 -C 6 )alkyl group; a halo (C 1 -C) alkyl group; a (C 1 -C 4 )alkoxy(Cj C 4 ) alkyl group; a (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C1-C,) alkyl groups, halo (C 1 -C 6 ) alkyl groups, (Cl C 6 ) alkoxy groups, halo (Ci-C 6 ) alkoxy groups, (C 1 -C,) alkyl thio groups, halo (Ci-C 6 ) alkylthio groups, (Ci-C,)alkyl sulfinyl groups, halo (C 1 -C 6 ) alkylsulfinyl groups, (Ci C 6 )alkylsulfonyl groups, halo (Cl-C 6 ) alkylsulfonyl groups, mono (C 1 -C 6 ) alkylamino groups, di (Cl-C 6 ) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (C 1 -C) alkoxycarbonyl groups; a phenyl (C 1 -C 4 ) alkyl group; a substituted phenyl(C 1 -C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C,)alkyl groups, halo (Cl-C 6 ) alkyl 141 groups, (Cl-C) alkoxy groups, halo (C-C) alkoxy groups, (Cl-C) alkylthio groups, halo (Cl-C) alkylthio groups, (Cl-C) alkylsulfinyl groups, halo (Cl-C) alkylsulfinyl groups, (Cl-C) alkylsulfonyl groups, halo (C-C) alkyl sulfonyl groups, mono (Cl-C) alkylamino groups, di(Cl CE)alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C1-C) alkyl groups, halo (Cl-C) alkyl groups, (C-C) alkoxy groups, halo (Cl-C) alkoxy groups, (C,-C) alkylthio groups, halo (Cl-C) alkylthio groups, (Cl-C) alkylsulfinyl groups, halo (Ci-C 6 ) alkylsulfinyl groups, (Cl-C) alkylsulfonyl groups, halo (Cl-C) alkyl sulfonyl groups, mono (Ci-C 6 ) alkylamino groups, di(C 1 CE)alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (C 1 -C)alkoxycarbonyl groups, R' being able to bind to R 6 to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring) ; -C (=Wl) -N (R 5 ) (R 6 ) (wherein W 1 , R 5 and R 6 are as defined above, R' being able to bind to R 6 to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the 142 ring, and R' being able to bind to R 4 to form a 5- to 8 membered ring that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); -C(=W')-R 5 (wherein W1 and R 5 are as defined above); -C (=W) -W'-R' (wherein W's, which may be the same or different, are as defined above, and R' is a (Cl-C)alkyl group; a halo(Cl C,)alkyl group; a (C-C 4 )alkoxy(C 1 -C 4 )alkyl group; a (C 1 C 4 )alkylthio(C-C 4 )alkyl group; a phenyl group; a substituted phenyl group having one or more substit uents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 ) alkyl groups, halo (C 1 -C.) alkyl groups, (C 1 C,) alkoxy groups, halo (Ci-C.) alkoxy groups, (C 1 -C,) alkyl thio groups, halo (C 1 -C,) alkylthio groups, (Ci-C,)alkyl sulfinyl groups, halo (C 1 -C 6 ) alkylsulfinyl groups, (C1 C 6 )alkylsulfonyl groups, halo (C 1 -C.) alkylsulfonyl groups, mono (Ci-C 6 ) alkylamino groups, di (C 1 -C 6 ) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C,) alkoxycarbonyl groups; a phenyl (C 1 -C 4 ) alkyl group; a substituted phenyl(C-C 4 )alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C) alkyl groups, halo (Cl-C.) alkyl groups, (Cl-C,) alkoxy groups, halo (Cl-C 6 ) alkoxy groups, (Ci-C 6 ) alkylthio groups, halo (Ci-C 6 ) alkylthio groups, (Ci-C6) alkylsulfinyl groups, halo (C 1 -C,) alkylsulfinyl 143 groups, (Ci-C 6 ) alkylsulfonyl groups, halo (Ci-C) alkyl sulfonyl groups, mono(Cl-CO)alkylamino groups, di(C 1 C 6 )alkylamino groups whose (C 1 -C,)alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C,)alkyl groups, halo (C 1 -C 6 ) alkyl groups, (Cl-C 6 ) alkoxy groups, halo (Cl-C) alkoxy groups, (C 1 -C 6 ) alkylthio groups, halo (Cl-C.) alkylthio groups, (Cl-C 6 ) alkylsulfinyl groups, halo (Ci-C) alkylsulfinyl groups, (C 1 -C 6 ) alkylsulfonyl groups, halo (Cl-C) alkyl sulfonyl groups, mono (C 1 -C 6 ) alkylamino groups, di(C 1 C,)alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups); -S0 2 -R' (wherein R 7 is as defined above); -S0 2 -N(R 5 ) (R 6 ) (wherein R 5 and R 6 are as defined above, R 5 being able to bind to R 6 to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, and R' being able to bind to R 4 to form a 5- to 8-membered ring that may contain three or four atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); -N(R 5 ) (R 6 ) (wherein R 5 and R6 are as defined above, R 5 being able to bind to R6 to form a 5- to 8-membered 144 ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, and R' being able to bind to R 4 to form a 5- to 8-membered ring that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms consti tuting the ring); or -N=C(R)R 6 (wherein R 5 and R 6 are as defined above, R 5 being able to bind to R 6 to form a 5 to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring); in the case of B being -N(R 4 )- (wherein R 4 is as defined above), R1 being able to be -OR 5 (wherein R 5 is as def ined above) , -C (W 2 ) -N (R 5 )R 6 (wherein W 2 is =CH-N0 2 , =N-N0 2 or =N-CN, and R 5 and R 6 are as defined above, R 5 or R 6 being able to bind to R 4 to form a 5- to 8-membered ring that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring) or -C(W2)-W-R7 (wherein W', W 2 and R' are as defined above, R 7 being able to bind to R 4 to form a 5- to 8-membered ring that may contain two or three atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms 145 constituting the ring), and R' being able to bind to A' to form a 5- to 8-membered ring that may contain one or two atoms which may be the same or different and are selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring, each of R2 and R 3 , which may be the same or different, is a hydrogen atom or a (Cl-C 3 )alkyl group, each of Q' through Q 4 is a carbon atom, each of Xs, which may be the same or different, is a halogen atom, a nitro group, a (Ci-C,) alkyl group, a halo (Cl-C 6 ) alkyl group, a (C 2 -C)alkenyl group, a halo (C 2 -C 6 ) alkenyl group, a (C 2 -C)alkynyl group, a halo (C 2 -C 6 ) alkynyl group, a (C,-CE) alkoxy group, a halo (C1-C.) alkoxy group, a (Ci-C 6 )alkylthio group, a halo (Cl-C) alkylthio group, a (C1-C 6 ) alkylsulfinyl group, a halo (Cl-C) alkylsulfinyl group, a (Cl-C) alkylsulfonyl group or a halo (Cl C,)alkylsulfonyl group, two adjacent Xs on the aromatic ring being able to be taken together to represent a fused ring that may have one or more substituents which may be the same or different and are selected from halogen atoms, nitro group, (Cl-C) alkyl groups, halo (Cl-CE) alkyl groups, (Cl-C) alkoxy groups, halo (Cl-C) alkoxy groups, (Cl-C 6 ) alkylthio groups, halo (Cl-C) alkylthio groups, (Cl-CE) alkylsulfinyl groups, halo (Cl-C) alkylsulfinyl groups, (Cl-C) alkylsulfonyl groups and halo (Cl-C) alkyl sulfonyl groups, n is an integer of 0 to 2, 146 Q' is a carbon atom or a nitrogen atom, each of Ys, which may be the same or different, is a halogen atom; a (Cl-C6) alkyl group; a halo (C1-C6) alkyl group; a (C 3 -C,) cycloalkyl group; a halo (C 3 -C.) cycloalkyl group; a (Cl-C) alkoxy group; a halo (Cl-C6) alkoxy group; a (Cl C6) alkylthio group; a halo (Cl-C6) alkylthio group; a (Ci C,) alkylsulfinyl group; a halo (Ci-C 6 ) alkylsulfinyl group; a (C-C6) alkylsulfonyl group; a halo (C1-C) alkylsulfonyl group; a halo (Cl-C) alkoxyhalo (Cl-C 6 ) alkoxy group; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, halo (C1-C) alkyl groups, halo (Cl-C 6 ) alkoxy groups, halo (Cl-C) alkylthio groups, halo (Cl-C6) alkylsulfinyl groups and halo (Cl-C)alkylsulfonyl groups; a phenyloxy group; a substituted phenyloxy group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, halo(Cl C,) alkyl groups, halo (Cl-C) alkoxy groups, halo (Ci C 6 )alkylthio groups, halo(Cl-C 6 )alkylsulfinyl groups and halo (Cl-C) alkylsulfonyl groups; a pyridyloxy group; or substituted pyridyloxy group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, halo(Cl CE) alkyl groups, halo (Cl-C) alkoxy groups, halo (Cl C,)alkylthio groups, halo(Cl-C)alkylsulfinyl groups and halo (Cl-CE)alkylsulfonyl groups, two adjacent Ys on the aromatic ring being 147 able to be taken together to represent a fused ring that may have one or more substituents which may be the same or different and are selected from halogen atoms, (Ci-C.) alkyl groups, halo (C 1 -C 6 ) alkyl groups, (Ci C 6 ) alkoxy groups, halo (cC0-6) alkoxy groups, (C1-C6) alkyl thio groups, halo (Cl-C) alkylthio groups, (Cl-C6) alkyl sulfinyl groups, halo (C1C6) alkylsulfinyl groups, (Ci C 6 )alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, phenyl group, and substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, halo(Cl-C 6 )alkyl groups, halo (Cl-C,) alkoxy groups, halo (C-C6) alkylthio groups, halo(C-C 6 ,)alkylsulfinyl groups and halo(C1 C6)alkylsulfonyl groups, m is an integer of 1 to 3, and each of Z' and Z 2 is an oxygen atom. 4. An agricultural and horticultural chemical comprising an aromatic diamide derivative or a salt thereof according to any one of claims 1 to 3 as an active ingredient. 5. An agricultural and horticultural chemical according to claim 4, which is an agricultural and horticultural insecticide.
6. A method for applying an agricultural and horticultural chemical, characterized by applying an agricultural and horticultural chemical according to claim 4 to a crop to be protected or the growth environment of the crop to be protected, in an effective dosage for protecting useful crops against 148 insect pests.
7. A method for applying an agricultural and horticultural chemical according to claim 5 which is an agricultural and horticultural insecticide.
AU22229/01A 1998-11-20 2000-12-22 Aromatic diamide derivatives, chemicals for agricultural or horticultural use and usage thereof Ceased AU773774B2 (en)

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AU93292/98A AU712421B2 (en) 1997-11-25 1998-11-20 Phthalic acid diamide derivatives, agricultural and horticultural insecticides, and a method for application of the insecticides
JP11-365408 1999-12-22
JP36540899 1999-12-22
PCT/JP2000/009146 WO2001046124A1 (en) 1999-12-22 2000-12-22 Aromatic diamide derivatives, chemicals for agricultural or horticultural use and usage thereof
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