AU773774B2 - 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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AU773774B2
AU773774B2 AU22229/01A AU2222901A AU773774B2 AU 773774 B2 AU773774 B2 AU 773774B2 AU 22229/01 A AU22229/01 A AU 22229/01A AU 2222901 A AU2222901 A AU 2222901A AU 773774 B2 AU773774 B2 AU 773774B2
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AU2222901A (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 claimed from PCT/JP2000/009146 external-priority patent/WO2001046124A1/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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—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
    • A01N43/04—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
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—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
    • A01N43/24—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 two or more hetero atoms
    • A01N43/26—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 two or more hetero atoms five-membered rings
    • A01N43/28—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • 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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    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • 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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    • C07C233/67—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
    • C07C233/75—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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    • C07C233/78—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 amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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    • C07C239/08—Hydroxylamino compounds or their ethers or esters
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    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—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
    • C07C271/12—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 hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—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
    • 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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    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
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    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
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    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C275/14—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
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    • C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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    • C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
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    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
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Description

E5 674 150/7 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 agricultural and horticultural insecticide, which contains said compound as an active ingredient; and a usage of the chemical.
BACKGROUND ART JP-A-1l-240857 discloses a compound analogous 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 The production of agricultural and horticultural 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 is desired because of, for example, the appearance of insect pests resistant to existing chemicals. In addition, because of the increased population of aged farmers, and the like, various labor-saving application methods are desired and the development of an agricultural and horticultural chemical having properties suitable for the application methods is desired.
The present inventors earnestly investigated in order to develop a novel agricultural and horticultural chemical, and consequently found that the aromatic diamide derivative represented by the general formula 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 effective usage, whereby the present invention has been accomplished.
That is, the present invention relates to an :aromatic diamide derivative represented by the general Sformula Z' AL-B-R
Q
4
R
20 {wherein A 1 is a (C 2 -Cs)alkylene group; a substituted (C,-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 (C,-C 6 alkyl groups, alkoxy groups, halo (Clalkoxy groups, (Cl-OG) alkylthio groups, halo (C 1 alkylthio groups, (C,-C 6 alkyjlsulfiriyl groups, halo alkylsulfinyl groups, (C 1
-C
6 alkylsulfonyl groups, halo (C,-0 6 alkylsulfonylJ groups, (CI-C 6 alkylthio (C 1
-C
6 alkyl groups, alkoxycarbonyl groups and phenyl group; a (C 3 -C )alkenylene group; a substituted (C'-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(Cl- C,).alkyl groups, (Cl-C 6 alkoxy groups,. halo 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, alkylsulfonyl groups, halo (Cl-
C
6 alkylsulfonyl groups, alkylthio (Cl-C 6 alkyl 4 groups, (Cl-C 6 )alkoxycarbonyl groups and phenyl group; a
(C
3 -C,)alkynylene group; or a substituted (C 3
-C
8 )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 6 )alkyl groups, (C-C)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,-C 6 )alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo(Cl-C 6 )alkylsulfonyl groups, (Cl-C 6 alkylthio (Cl-C 6 alkyl groups, (Cl-C6) alkoxycarbonyl groups and phenyl group, any of the saturated carbon atoms in the above-mentioned (C2-C 8 )alkylene group, substituted (C 1 C )alkylene group, (C 3 alkenylene group, substituted
(C
3 alkenylene group, (C 3
-C
8 alkynylene group or substituted (C 3 -C,)alkynylene group being able to have a
(C,-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
2 -Cs) alkylene group, substituted (Cl-C,)alkylene group, (C 3 -CB)alkenylene group and substituted (C 3 -C,)alkenylene group being able to form a (C 3
-C
6 cycloalkane ring or a (C 3 -CS)cycloalkene ring together with an alkylene group or an alkenylene group, B is or (wherein R' is a hydrogen atom; a (Cl-C 6 )alkyl group; a halo(C 1
-C
6 )alkyl group; a
(C
3
-C
6 )alkenyl group; a halo(C 3 -C)alkenyl group; a (C 3
C
6 )alkynyl group; a (C 3
-C
6 )cycloalkyl group; a alkylcarbonyl group; a halo(Cl-C 6 alkylcarbonyl group; a (C 1
-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, (Cl-C) alkyl groups, halo (C-C6) alkyl groups, (Cl-
C
6 alkoxy groups, halo(Cl-C) alkoxy groups, (Cl-C 6 alkylthio groups, halo(Cl-C 6 )alkylthio groups, (C,-C)alkylsulfinyl groups, halo alkylsulfinyl groups, (Clalkylsulfonyl groups, halo(C-C) alkylsulfonyl groups, mono (C-C 6 alkylamino groups, and di(C-C) alkylamino groups whose (Cl-C 6 )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 group, nitro group, (C-C6)alkyl groups, halo(C-C6) alkyl groups, (C1-C6) alkoxy groups, halo(C1-C6) alkoxy groups, S. (C1-C) alkylthio groups, halo(C-C 6 alkylthio groups, S~(C-C6) alkylsulfinyl groups, halo (C-C6) alkylsulfinyl groups, (C-C6) alkylsulfonyl groups, halo(C-C,) alkylsulfonyl groups, mono(C,-C.) alkylamino groups, and di(Cl- C )alkylamino groups whose (C-C 6 )alkyl groups may be the same or different; a phenyl(C-C)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-C6) alkyl groups, halo(C 1 -C,)alkyl 6 groups, alkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C 6 alkyithia groups, halo (C-C)alkylthio groups,
(C
1
-C
6 alkylsulfinyl groups, halo (C 2
-C
6 alkylsulfinyl groups, (C-C)alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfony3. groups, mono (C,-C)al kyl amino groups, di(Cl-
C
6 )a1kylamino groups whose (C 1
-C
6 )alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups),
R
1 is a hydrogen atom; a (C 1
-C
6 )alkyl group; a halo (Cl-C 6 )alkyl group; a (Cl-C 4 )al koxy (Cl-C 4 )alkyl group; a (Cl-C 4 )alkylthio(Cl--C 4 )alkyl group; a (02-
C
6 alkenyl group; a halo (C 2
-C
6 alkenyl group; a (C 3
C
6 alkynyl group; a halo (C 3
-C
6 alkynyl group; a (03-
C
6 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, (C 1
-C
6 alkyl groups, halo (C 1
-C
6 alkyl groups, (Cl-
C
6 )alkoxy groups, halo (Cl-C6) alkoxy groups, (l-06 alkylthio groups, halo..(Cl-C 6 alkylthio groups, (Cl-C 6 )alkylsufiy grus hao.,C)aklufnlgop,(l C ysulfnyl groups, halo (Cl-C 6 alkylsulfnyl groups, 1 mono (C 1
-C
6 alkylamino groups, di (C,-C 6 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 phenyl1(CI-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 (01-06) alkyl gop, (Cl-C 6 alkoxy groups, halo (C,-C 6 alkoxy groups, alkyithia groups, halo (0 1
-C
6 alkylthio groups, (C,-0 6 alkylsulfinyl groups, halo (Cl-C 6 alkylsulf inyl.
groups, (C 1
-C
6 alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl groups, mono (Cl-C) alkylarnino groups, di(C,- C,)alkylamino groups whose (C,-C,)alkyl groups may be the same or different, and (C 1
-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 (C 1
-C
6 alkyl groups, (Cl-C 6 alkoxy groups, halo (Cl-C 6 alkoxy groups,
(CI-C
6 alkylthio groups, halo (C,-C 6 alkylthio' groups,,alkylsulfinyl groups, halo (0 1 alkylsulfinyl.
groups, alkylsulfonyl groups, halo (Cl-C 6 alkyl- .sulfonyl groups, mono (C 1
-C
6 al kyl amino groups, di(C,alkylamino groups whose (C 1
-C
6 )alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; (=Wl (R 5 (R 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 (Cl-C 6 )alkyl group; a halo (C 1
-C
6 alkyl. group; a (Cl-C 4 alkoxy (Cl-
C
4 alkyl group; a (CC-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 6 alkyl groups, halo (Cl-C 6 alkyl groups, (C 1 alkoxy groups, halo (C,0)aloygrus
(C
1
-C
6 alkyl- 8 thio groups, halo alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (C 1 -C,)alkylsulfinyl groups, (Cl-
C
6 alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, mono al kyl amino groups, di (Cl-C 6 alkylamino groups whose (C 1
-C
6 )alkyl groups may be the same or different, and alkoxycarbonyl groups; a phenyl (Cl-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 6 )alkyl groups, halo (C,-C 6 )alkyl groups, (Cl-CE) alkoxy groups, halo(C 1
-C
6 alkoxy groups,
(C
1
-C
6 )alkylthio groups, halo (C,-C,)alkylthio groups, alkylsulfinyl groups, halo alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo (C 1
-C
6 alkylsulfonyl groups, mono (C,-C 6 alkyl amirno groups, di (Clalkylamino groups whose (Cl-C 6 alkyl groups may be the same or different, and alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group :having oneor more substituent-s--which may be the same or different and are selected from halogen atoms, cyano group, nitro group, alkyl groups, halo (Cl-C 6 )alkyl groups, (C,-C 6 )alkoxy groups, halo (Cl-C 6 )alkoxy groups, (Cl-CE) alkylthio groups, halo (C,-C 6 )alkylthio groups,
(C
1
-C
6 alkylsulfinyl groups, halo (Cl-C 6 alkylsulfinyl groups, (C 1
-C
6 )alkylsulfonyl groups, halo (Cl-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,
R
5 being able to bind to R 6 to form a 5- to 8membered 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 constituting the ring); -CW(=W)-R 5 (wherein W 1 and
R
5 areas defined above); -C(=W 1 (wherein W's, 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 (Ci-C) alkoxy(Ci-C 4 )alkyl group; a (Cl-C 4 )alkylthio(Cl-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 6 alkyl groups, halo (Ci-C 6 alkyl groups, alkoxy groups, halo(C l C,)alkoxy groups, (C 1
-C
6 )alkylthio groups, halo(Cl-
C
6 )alkylthio groups, (Ci-C) alkylsulfinyl groups, *halo (Ci-C 6 alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo(Cl-C) alkylsulfonyl groups, mono(Cl- C,)alkylamino groups, di(C,-C,)alkylamino groups whose
(C
1
-C
6 )alkyl groups may be the same or different, and
(C-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, (C 1
-C
6 )alkyl groups, halo(C 1
-C
6 )alkyl groups, (C 1
-C
6 )alkoxy groups, halo(CI-C 6 )alkoxy groups, (C-C6) alkylthio groups, halo (Cl-C 6 alkylthio groups, (Cl-C) alkylsulfinyl groups, halo (C-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 Sgroup, nitro group, (C 1
-C
6 alkyl groups, halo(Cl-C 6 alkyl groups, (Cl-C 6 alkoxy groups, halo(Cl-CE) alkoxy groups, (C1-C6) alkylthio groups, halo (C-C6) alkylthio groups, alkylsulfinyl groups, halo(Cl-C 6 alkylsulfinyl groups, (C1-C6) alkylsulfonyl groups, halo (Cl-C6) alkylsulfonyl groups, mono(Cl-C) alkyl-amino groups, di(Cl-
C
6 )alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups); -SO2-R (wherein R 7 is as def ned above); -S0 2
-N(R
5
(R
6 (wherein R 5 and R 6 are as defined above, R 5 being able to 11 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 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 S. nitrogen atom, between adjacent carbon atoms constituting the ring); or -N=C(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 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 -OR (wherein R 5 is as defined above), -C(W 2
-N(R)R
6 (wherein
W
2 is =CH-N0 2 =N-N0 2 or =N-CN, and R 5 and R 6 are as 9 9.
12 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 7 (wherein W1, W 2 and R 7 are as defined above, R 7 being able to bind to R 4 to form a 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 8membered 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
8 (wherein A 2 is
-C(=NR
9 (wherein R 9 is a hydrogen atom, a (C 1
-C
6 )alkyl group, a (Ci-C 6 )alkoxy group, a mono(C,-C) alkylamino group, a di(C-C 6 )alkylamino group whose (Ci-C 6 )alkyl groups may be the same or different, a (C-C 6 )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, (C 1 -C6)alkyl groups, halo(C,-C 6 )alkyl groups, (Ci-C 6 alkoxy groups, halo(C 1
-C
6 )alkoxy groups, alkyithia groups, halo alkyithic groups,
(C
1
C
6 )alylslfiylgroups, halo (C,-C 6 alkylsulfinyl groups, alkylsulfonyl groups, halo alkylsulfonyl: groups, mono (C,-C 6 )alkylarnino groups, di (Cl- C.)alkylamino groups whose (C 1
-C
6 )aikyl groups may be the same or different, and (C,-C 6 )alkoxyccarbonyl groups), a (C,-Ce)alkylene group, a halo (C,-C 8 alkylene group, a
(C
3
-C
6 alkenylene group, a halo (C 3
-C
6 alkenylene group, a
(C
3
-C
6 )alkyniylene group or a halo (C 3
-C
6 alkynylene group, in the case of A' being or -C(=NR 9 (wherein R 9 is as defined above), R' is a hydrogen atom; a (Cl-C 6 alkyl group; a halo (Cl-C 6 alkyl group; a (C 3
-C
6 )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, (Cl-C 6 alkoxy groups, halo (Cl-C 6 alkoxy groups, alkylth-io. groups, halo alkylthio groups, ,)akluliy grus ao*IC6 lysli grup C-C 6 alkylsulfnyl groups, halol-C 6 alkyliy sulfonyl groups, mono (Cl-C 6 alkylainino groups, di (C 1
C
6 alkylamino groups whose (C 1
-C
6 )alkyl groups may be t .he same or different, and (Cl-C 6 )alkoxycarbonyl groups; a S 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-COalkyl. groups, halo alkyl 14 groups, (C 1 alkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C 6 alkylthio groups, halo (C 1 :Cd)alkyithic groups, alkylsulfinyl groups, halo (Cl-C 6 )alkylsulfinyl groups, (C-C 6 )alkylsulfonyl groups, halo (CI-C 6 alkylsulfonyl. groups, mono (CI-C, 6 alkylamino groups, di (C 1
C
6 )alkylamino groups whose (C,-C)alkyl groups may be the same or different, and (Cl-C)alkaxycarbony. groups; or
-A-R
10 (wherein A 3 is or -N CR 1 (wherein R 1 is a hydrogen atom; a (Cl-C 6 alkylcarbonyl group; a halo (C 1
C
6 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, (Cl-C 6 )alkyl groups, halo(Cl-
C
6 alkyl groups, (Cl-C 6 alkoxy groups, halo (Cl-C 6 alkoxy groups, alkylthio groups, halo (Cl-C 6 alkylthio groups, alkylsulfinyl groups, halo (Cl-C, 6 alkylsul finyl. groups, (Cl-C 6 alkylsul fonyl groups, halo (C 1 0. .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 (C 1 -C,)alkoxycarbonyl groups; a phenyl (Cl-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 0000 0or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 alkyl. groups, halo (Cl-C 6 alkyl.
groups, (Cl-C 6 )alkoxy groups, halo (Cl-C 6 )alkoxy groups, alkylthio groups, halo (CI-C 6 alkylthio groups, (C1-06) alkylsulfinyl groups, halo alkylsulfinyl groups, (C 1
-C
6 alkylsulfonyl groups, halo (C,-C 6 alkylsulfonyl groups, mono (C 1
-C
6 alkylamino groups, di (Cl- 06) alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups), and R 10 is a (Cl-C 6 )alkyl group; -a halo (C,-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 hal~o(C 3 -C)alkynyl group; a (C 3
C
6 )cycloalkyl group; a halo (C 3 -C,)cycloalkyl group; a (Cl-C 6 alkylcarbonyl group; a halo (Cl-C 6 )alkylcarbonyl group; a,(Cl-C 6 )alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more substitueiits 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-
C
6 alkoxy groups, halo (01-06) alkoxy groups, (C,-C 6 alkylthio groups, halo (C 1
-C
6 )alkylthio groups, (Cl-C 6 alkylsulfiny]. groups, halo (01-06) alkylsul finyl groups, (Cl-
C
6 alkylsulfonyl groups, halo (C 1
-C
6 alkylsulfonyl groups, mono alkylamino groups, di (Cl-C 6 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.(CI-C 4 alky. 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 alkyl. groups, (C 1 alkoxy groups, halo alkoxy groups, alkyl- '00, thio groups, halo (Cl-C 6 alkylthio groups, (Cl-C) alkyl- 16 sulfinyl groups, halo alkylsulfinyl groups, (Cl-
C
6 alkylsulfonyl groups, halo (C-C 6 )alkylsulfonyl groups, mono alkylamino groups, di (Cl-C 6 alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, and (Cl-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, (Cl-C 6 alkyl groups, halo (Cl-C 6 alkyl groups, .(Clalkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C 6 alkylthio groups, halo (C 1
-C
6 alkylthio groups, (C 1
-C
6 alkylsulf inyl groups,' halo (Cl-C 6 alkylsulf inyl groups, (C 1
C
6 alk' lsulfonyl groups, halo (Cl-C 6 alkylsulfonyl groups, mono (C 1
-C
6 al1kyl amino groups, di (Cl-C 6 alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, anid (Cl-C 6 alkoxycarbonyl groups), in the case of A 2 being a (Cl-C)alkylene group, a halo (Cl-C) alkylene group, a (C 3
-C
6 allcenylefle rou, a'habICC~) (C-C 6 aiynylene :group or a halo (C 3
-C
6 alkynylene group, Re 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 alkoxycarbonyl -group; a phenyl group; a substi- V 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, (Cl- 9 CO) alkyl groups, halo (C,-C 6 alkyl groups, (C 1
-C
6 alkoxy *.groups, halo (Cl-C 6 alkoxy groups, (CI-C 6 alkylthio 17 groups, halo (Cl-C 6 alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (Cl-C 6 alkylsulfinyl groups, (Cl-C 6 )alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl groups, mono (Cl-C 6 al kyl amino groups, di alkylamino groups whose (Cl-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 (C,-C 6 ,)alkyl groups, (Cl-
C
6 alkoxy groups, halo alkoxy groups, (Cl-C 6 alkylthio groups, halo (Cl-C 6 alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (C-C 6 )alkylsulfinyl groups, (Cl-
C
6 alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl groups, mono (Cl-C 6 al kyl amino groups, di (Cl-C 6 )alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; or -A'-R 3 (wherein A 4 is -SO 2
-N(R
1 1 (wherein R" is as ~.:def ined above) -C or -C (=N-OR 3 (wherein R' 3 is a :hydrogen atom, a (C 1
-C
6 alkyl group, a halo (Cl-C 6 alkyl *group, a (C 3
-C
6 alkenyl group, a halo (C 3 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(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, alkyl groups, halo (Cl alkyl groups, (Cl-C 6 alkoxy groups, halo (Cl-C 6 alkoxy 18 groups, (C 1
-C
6 alkyithic groups, halo (C-C)alkylthio groups, (Cl-C 6 )alkylsulfinyi. groups, halo (Cl-C 6 )alkylsulfinyl groups, (Cl-C6) alkylsul fonyl groups, halo (Cl- 06) alkylsulfonyl groups,, mono alkyl amino groups, di(C 1 -0 6 )alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (C 1 -0.7 6 )alkoxycarbonyl groups), in the case of A' being -S02- or -N (R' 1 (wherein R" is as defined, above) R 1 2 is a hydrogen atom; a (C 1
-C
6 alkyl group; a halo alkyl group; a (03-06) alkenyl group; a halo (C 3 alkenyl group; a (C 3
-C
6 alkynyl group; a halo (C 3
-C
6 alkynyl group; a (03-06) cycloalkyl group; a halo (C 3 cycloalkyl group; a (Cl-C 6 )alkylcarbonyl group; a halo (Cl-C 6 )alkylcarbonyl group; a (Cl-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 a toms, cyano group, nitro group, :(01-06) alkyl groups, -halo (01-06) alkyl groups, (Cl- 05)alkoxy groups, halo (01-06) alkoxy groups, (01-06) alkylthio groups, halo (01-06) alkyithia groups, (01-06,) alkylsulfinyl groups, halo (Cl-C.)alkyls.ulfinyl groups, (C1- C6) alkylsulfonyl groups, halo (01-06) alkylsulfonyl groups, mono al1kyl.amino groups, di (Cl-C 6 alkylamino groups whose (0 1
-C
6 )alkyl groups may'-'be the same or different, sees .4 and (01-06) alkoxycarbonyl groups; a phenyl (01-04) alkyl *group; a substituted phenyl (C -C 4 )alkyl. group having on the ring one or more substituents which may be the sm 19 or different and are selected from halogen atoms, cyano group, nitro group, alkyl groups, halo (Cl-C 6 alkyl groups, (C 1
-C
6 alkoxy groups, halo (Cl-C 6 alkoxy groups, (C-C)alkylthio groups, halo (C-C 6 )alkylthio groups,
(C
1 -C6) al kylsulfinyl groups, halo (Cl-C,)alkylsulfinyl groups, (Cl-C 6 )alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl groups, mono alkylamino groups, di (Clalkylamino groups whose (Cl-C a 1kyl groups may be the same or different, and (C 1 -C,)a-lkoxycarbonyl 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
-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,
(C-C
6 )alkylsulfinyl groups, halo(C,-C 6 )alkylsulfinyl groups, (C l-C 6 alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl. groups, mono (C 1
-C
6 alkylamrino groups, di (Ci 1 C C 6 )alkylamino groups whose (C 1
-C
6 )alkyl groups may be the same or different, and (C,-C,)alkoxycarbonyl groups, o(ii) in' the case of A' being or -C (=NOR 1 3 (wherein R' 3 is as defined above), R 12 is a hydrogen atom; a (C-C)alkyl group; a halo (Cl-C 6 )alkyl group; a
(C
2
-C
6 )alkenyl group; a halo(C 2
-C
6 )alkenyl group; a (C 3 .S 0)cycloalkyl group; a halo (C 3
-C
6 cycloalkyl. group; a alkoxy group; a halo (C-C 6 alkoxy group; a 1 eC. 6) alkylthio group; a halo (Cl-C 6 )alkylthio group; a .monio(C-C) alkylamino group; a di (Cl-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 and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 )alkyl groups, halo(C-C 6 alkyl groups, (Cl- 0 6 )alkoxy groups, halo(C 1
-C
6 )alkoxy groups, (Cl-C 6 )alkylthio groups, halo (C,-C,)alkylthio groups, (C,-C 6 alkylsulfinyl groups,,halo(Cl-C 6 alkylsulfinyl groups, (Cl- C)alkylsulfonyl groups, halo(C,-C 6 alkylsulfonyl groups, mono alkylamino groups, di(C-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, alkyl groups, halo (C,-C 6 alkyl 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(Cl-C) alkylsulfinyl groups, (C 1 CE)alkylsulfonyl 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 (C-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, (C,-C 6 alkyl groups, haloiC,-C)alkyl groups, (C 1
C
6 alkoxy groups, halo(C 1
-C
6 )alkoxy groups, (Cl-C 6 )alkyl- 21 thio groups, halo alkyithia groups., ('%Cl-C 6 alkylsulfinyl groups, halo (Cl-C,)alkylsulfny. groups, (Cl-
C
6 )alkylsulfonyl groups, halo (C-C 6 )alkylsulfonyl groups, mono (Cl-C 6 )alkylamino groups, di(C,-C 6 )alkylamino groups whose (C,-C,)alkyl groups may be the same or different, and (C 1
-C
6 )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, (Cl-C,)alkyl groups, halo (Cl-C 6 alkyl groups, (C 1
C
6 alkoxy groups, halo (C1-06) alkoxy groups, (Cl-C 6 alkylthio groups, halo (C 1
-C
6 alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (01-06) alkylsulfinyl groups, (C 1 06) alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl groups, mono (Cl-C 6 al kyl amino groups, di (Cl-Cd)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, S..(Cl-C 6 alkyl groups, halo (C1-06) alkyl groups, (C 1 06) alkoxy groups, halo (01-06) alkoxy groups, (Cl-C 6 alkylthio groups, halo (Cl-C) alkylthio groups, (C,-C 6 alkylsulfinyl groups, halo (Cl-C 6 alkylsulfinyl groups, (C 1 C 6) alkylsu~fonyl groups, halo alkylsulfonyl1 groups, .mono (Cl-C 6 al kyl amino groups, di (Cl- alkyl amino groups whose (Cl-C 6 alkyl groups may be the same or different, and (Cl-C 6 alkoxycarbonyl groups)), 22 further, R 2 being able to bind to A 1 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 Q' 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 cycloalkyl group; a halo(C 3
-C
6 cycloalkyl group; a (C-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,
(C
1
-C
6 )alkyl groups, halo(C 1
-C
6 )alkyl groups, (Ci-
C
6 )alkoxy groups, halo(Cl-C 6 alkoxy groups, (C 1 alkylthio groups, halo(Ci-C 6 alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo(Ci-C)alkylsulfinyl groups, (C 1
C
6 )alkylsulfonyl groups, halo(C,-C.)alkylsulfonyl groups, mono (Cl-C) alkylamino groups, di(Ci-C 6 )alkylamino groups whose (Ci-Cg)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, (Ci-C 6 )alkyl groups, halo(C 1 alkyl groups, (C l
C
6 )alkoxy groups, halo(C 1
-C
6 alkoxy groups, (C-C 6 alkylthio groups, halo(Ci-C 6 alkylthio groups, (C--C 6 alkyl- 23 sulfinyl groups, halo (Cl-C 6 alkylsulfiny. 'groups, (C 1
C
6 alkylsulfonyl groups, halo (Cl-C 6 alikylsulfonyl groups, mono (Cl-C)al kyl amino groups, di (0 2
-C
6 )alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (CI-C 6 alkoxycarbony]. groups; or -A 5 7R 4 (wherein A' is -SO 2 -C -C (=NOR 1 3 (wherein
R"
3 is as defined above), a (0 1
-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 (C 2 -C)alkynylene group or a halo (03-06) alkynylene group, in the case of A' being -So- or
-SO
2
R'
4 is a halo (C 3
-C
6 cycloalky. group; a halo (C 3
C
6 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,-C,)alkyl groups, halo alkyl groups, (01-C6) alkoxy groups, halo (Cl- :C0) alkoxy groups, (01-C6) alkyithia groups, halo (Cl- 6) alkylthio groups, (C,-C,)alkylsulfinyl groups, halo (01-06) alkylsulfinyl groups, alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl groups, mono (C 1 06) alkylamino groups, di(C 1
-C
6 )alkylamino gr~qoups 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 group, nitro group, (01-06) alkyl groups, halo (01-06) alkyl groups, 24 06) alkoxy groups, halo (C,-C 5 alkoxy gro~ups, .(Cl-C 5 alkylthio groups, halo (Cl-C6) alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (C 1
-C
6 )alkylsulfinyl groups, (Cl- 06) alkyilsulfonyl groups,,. halo alkylsulfonyl groups, mono (C01-C6) al kyl amino groups, di alkylamino groups whose (C 1 C)alkyl groups may be .the same or different, and (Cl-C6) alkoxycarbonyl groups; or -A 6-R 15 (wherein A 6 is a (C 1 -C6)alkylene group, a halo (C 1 -C,)alkyJlene group, a (C 3 -C6)alkenylene group, a halo (C 3 -C6) alkenylene group, a (03-C6) alkynylene gr oup or a halo alkynylene group, and R's is a hydrogen atom; a halogen atom; a (03- C6) cycloalkyl group; a halo (C 3 -C,)cycloalkyl group; a (01-06) 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, (Cl- C6) alkyl groups, halo (01-06) alkyl groups, (Cl-C6) alkoxy groups, halo (01-06) alkoxy groups, alkylthio groups, halo (01-06) alkylthio groups, (01-06) alkylsulfinyl groups, halo (Cl-C6) alkylsulfinyl. groups, (Cl-C6) alkylsulfonyl groups, halo (Cl-Cs) alkylsulfonyl groups, mono alkylamino, groups, di alkylamino groups whose alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; or -A7-R 1 6 (wherein A7 is -SO- or _S2_ and R 16 is a (01-06) alk yl grup a aoa.C)aky ru, CC)aknlgop gru;a halo (CC alkyl group'; a (C o) alkenyl group; *ahalo (C 3
C
6 alknyl group; a (C 6 ylalkyl group; a a. 3 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- C6) alkyl groups, halo (CC 6 alky- groups, alkoxy groups, halo (Cl-C 6 alkoxy groups, (C-C 6 )alkylthio groups, halo (Cl-C 6 alkylthio groups, (C-C)alkylsulfinyl groups, halo (Cl-C 6 alkysulfinyl groups, (C,-C 6 )alkylsulfonyl groups, halo (C-C 6 )alkylsulfonyl groups, mono (C 1
-C
6 al kyl amino groups, di alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-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, alkyl groups, halo (Cl-C 6 alkyl. groups, (C 1
C
6 alkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C 6 alkyl- :thio groups, halo (C 1
-C
6 alkylthio:groups, (C 1
-C
6 )alkyl- :sulfinyl groups, alkylsulfinyl groups,
*C
6 alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl groups, mono (Cl-C 6 alkylamino groups, di alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C 6 alkoxycarbonyl groups), in the case of A 5 being -C or -C(=NOR 1 3 (wherein R 13 is as defined above), R is a *6 al.y gr up CO- alkyl group; a halo (C-C 6 alkyl group; a
:C
6 cycloalkyl group; a halo (C 3
-C
6 )cycloalkyl group; a 26 (Cl-C)alkoxy group; a (Cl-C 6 )alkylthio group; a mono(Cl-
C
6 )alkylamino group; a di 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(C,-C,)alkyl groups, (Cl- C) alkoxy groups, halo (C-C 6 alkoxy groups, (Cl-C 6 alkylthio groups, halo(C 1
-C
6 alkylthio groups, (Cl-C) alkylsulfinyl groups, halo(C,-C) alkylsulfinyl groups, (Cl-
C
6 alkylsulfonyl groups, halo(Cl-C 6 )alkylsulfonyl 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 1 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(C 1
-C
6 ,)alkyl groups, (C 1
C
6 alkoxy groups, halo(C-C 6 alkoxy groups, (Cl-C 6 alkyl- :thio groups, halo(Cl-C 6 )alkylthio groups, (Cl-C)alkylsulfinyl groups, halo(C-C) alkylsulfinyl groups, (C-
C
6 alkylsulfonyl groups, halo(Cl-C)alkylsulfonyl groups, mono (Cl-C 6 alkylamino groups, di(Cl-C 6 )alkylamino groups whose (CI-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, 27 (Cl-C 6 alkyl groups, halo (Cl-C 6 alkyl groups, (Cl-
C
6 alkoxy groups, halo (C 1
-C
6 alkoxy groups, (C,-C 6 alkylthio groups, halo (C 1
-C
6 alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (C,-C 6 alkylsulfinyl groups, (Cl-
C
6 alkylsulfonyl groups, halo (CI-C 6 alkylsulfonyl groups, mono al kyi amino groups, di alkylamin-o groups whose (C,-,C)alkyl groups may be the same or different, and alkoxycarbonyl groups, in the case of A' being a (Cl-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 (C 2 alkynylene group or a halo (C 3 alkynylene group, R' 4 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 )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, (Cl-C)alkyl groups, halo (Cl-C 6 )alkyl groups,. (C-C 6 )alkoxy groups, halo (C 1
-C
6 )alkoxy groups, (Cl-C 6 alkylthio groups, halo (Cl-C 6 alkylthio groups, (Cl-C 6 )a'lkylsulfinyl groups, halo (Cl-C 6 alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl groups, mono (Cl- C 6 al kyl amino groups, di (Clalkylamino groups whose (Cl-C 6 )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 28 group, nitro group, (0 1 -C,)alkyl groups, halo (Cl-C 6 alkyl groups, alkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C6) alkylthio groups, halo (Cl-C 6 alkylthio groups, alkylsulfinyl groups, halo (01-06) alkylsulfinyl groups, (C-C 6 )alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, mono alkyl amino groups, di(Cl- 0 6 alkylamino groups whose (Cl-C 6 alkyl groups may be the same or different, and (C-C 6 )alkoxycarbonyl groups; or
-A--R
1 7 (wherein A' is -So- or -S0 2 and R" 7 is a (C 3
-C
6 cycloalkyl group; a halo (0 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 (CI-C 6 alkyl groups, (Cl-
C
6 alkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C 6 alkylthio groups, halo (Cl-C 6 alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (C-C 6 )alkylsulfinyl groups, (Cl- C6) alkylsulfonyl groups, halo (C,-C 6 )alkylsulfonyl groups, mono (Cl-C 6 )alkylamino groups, di alkyl amino groups :whose (C 1
-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 V, selected from halogen atoms, cyaria group, nitro group,
(C
1
-C
6 alkyl groups, halo (C 1
-C
6 alkyl groups, (Cl- 06) alkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C 6 alkylthio groups, halo (Cl-C 6 alkylthio groups, (Cl-C 6 alkyl- *.:sulfinyl groups, halo (Cl-C 6 )alkylsulfinyl groups, (C 1
-I
29 06) alkylsulfonyl groups, halo alkylsulfony). groups, mono (01-06) al kyl amino groups, di (Cl7C)alkylamino groups whose (C-C)alkyl groups may be the same or different, anid (Cl-C 6 alkoxycarbonyl groups; or -A 9
-R
6 (wherein A' is a (C-C,)alkylene group, a halo (Cl-C 6 alkylene group, a (02-06) alkenylene group, a halo (02-C6) alkenylene group, a (C 2 -C)alkynyiene group or a halo (C 3
-C
6 alkynylene group, and R" 9 is a hydrogen atom; a halogen atom; a (03-
C
6 cycloalkyl group; a halo (C 3
-C
6 cycloalkyl group; a (Cl-C 6 )alkoxy group; a halo (Cl-C 6 alkoxy group; a (Cl-
C
6 )alkylthio group; a halo (C 1
-C
6 alkylthio group; a (Cl- 06) alkylsulf inyl group; a halo (Cl- 6 alkylsulf inyl group; a (01-06) alkylsulfonyl group; a halo (01-CE) 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, (Cl-CE) alkyl groups, halo (Cl-06) alkyl groups, (Cl-CE) alkoxy groups, halo (Cl-C 6 )alkoxy groups, (0-C 6 alkylthio groups, halo (0-C 6 alkylthio groups, :(01-06) alkylsulf inyl groups, halo (Cl-CE) alkylsulf inyl .:groups,, (01-06) alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl groups, mono (01-CE) alkyl amino groups, di (Cl- 06) alkylamino groups whose (Cl-0 6 alkyl groups may be the same or different, and (0 1 -0 6 )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, (01-06) alkyl groups, halo (01-06) alkyl groups, (Cl-C 6 alkoxy groups, halo (Cl-C 6 alkoxy groups, (C106 alkylt-io groups, halo (Cl-C 6 alkylthio groups,
(C-C
6 )alkylsulfinyl groups, halo (C-C 6 )alkylsulfinyl groups, alkylsulfonyl groups, halo (C C 6 alkylsulfonyl groups, mono (CI-C 6 )alkylamino groups, di (Cl- 06) alkylamino groups whose (Cl-C 6 alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; a phenylthio group; a substituted phenyithic group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, alkyl groups, halo (Cl-C 6 alkyl groups, (01-06) alkoxy groups, halo (C 1
-C
6 alkoxy groups, alkylthio groups,. halo (Cl-C 6 alkylthio groups,
(C
1
-C
6 )alkylsulfinyl groups, halo (Cl-C 6 alkylsulfinyl groups, (Cl-C 6 )alkylsulfonyl groups, halo (Cl-C 6 alkylsul fontyl groups, mono (C 1
-C
6 alkylamino groups, di (C 1 06 )alkylamino groups whose (C 1
-C
6 )alkyl groups may be the same or different, and (01-C6) alkoxycarbonyl groups; a S *.*heterocyclic-group; or a heterocyclic group having one *5:5 :or more substituents which may be the same or different :and are selected from halogen atoms, cyano group, nitro group, (Cl-C6) alkyl groups, halo (C 1
C
6 alkyl groups, (Cl- 06) alkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C6) alkylthio groups, halo alkylthio groups, (Cl-Cs) alkylsulfinyl groups, halo al.kylsulfinyl groups, (CI- 06) alkylsulfonyl groups, halo alkylsulfonyl groups, S.:mono alkylamino giroups, di (01-0C6) alkylamino groups :whose (Cl-C 6 )alkyl groups may be the same or different, 31 and (C-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, (C-C 6 ,)alkyl groups, halo (Cl-C 6 alkyl groups, alicoxy groups, halo(C,- C )alkoxy groups, (C,-C.)alkylthio groups, halo(Cl-
C
6 alkylthio groups, (Cl-C) alkylsulfinyl groups, halo (Cl-C alkylsulfinyl groups, (C-C 6 alkylsulfonyl groups, halo(Cl-C 6 alkylsulfonyl groups, mono(C 1
C
6 )alkylamino groups, di(Cl-C 6 )alkylamino groups whose (C-C)alkyl groups may be the same or different, and
(C
1
-C
6 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(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(C-C 6 ,)alkyl groups, (C,-C 6 )alkoxy groups, halo(C 1
-C
6 )alkoxy groups,
(C
1
-C
6 alkylthio groups, halo(Cl-C.) alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo(C 1 -C,)alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo alkyla .sulfonyl groups, mono(Cl-C)alkylamino groups, di(Clg C,)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 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(Cl-C.)alkyl groups, (Cl-C) alkoxy groups, halo alkoxy groups,
(C
1
-C
6 alkylthio groups, halo(Cl-C) alkylthio groups,
(C-C
6 alkylsulfinyl groups, halo(C-C) alkylsulfinyl groups, (Cl-C) alkylsulfonyl groups, halo alkylsulfonyl groups, mono(Cl-C) alkylamino groups, di(Cl-
C
6 )alkylamino groups whose (C,-C)alkyl groups may be the same or different, and (C,-C)alkoxycarbonyl groups; or
-A
5 -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-C) alkyl groups; halo alkyl groups; (C 1 alkoxy groups; halo(Cl-C) alkoxy groups; (C,-C 6 alkylthio groups; halo(C,-C.) alkylthio groups; (Cl-C 6 alkylsulfinyl groups; halo(C-C)alkylsulfinyl groups; (Cl-
C
6 )alkylsulfonyl groups; halo(Cl-C 6 alkylsulfonyl groups; phenyl group; substituted phenyl groups having one or more substituents which may be the same or different 9 and are selected from halogen atoms, cyano group, nitro group, (C 1 alkyl groups, halo (Cl-C 6 alkyl groups, (Cl- *C,)alkoxy groups, halo(Cl-C 6 )alkoxy groups, (Cl-C,)alkylthio groups, halo(Cl-C 6 alkylthio groups, alkyl- 32A sulfinyl groups, halo (Cl-C 6 alkyl.sulfinyl groups, (Cl-
C
6 alkylsulfonyl groups, halo (C 2
-C
6 alkylsulfonyl groups., mono (Cl-C 6 )al kyl amino groups, di(Cl-C 6 )alkylamino groups whose (Cl-C 6 )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, (Cl-C 6 alkyl groups, halo (C,-C 6 alkyl groups,-,(Cl-
C
6 )alkoxy groups, halo (C,-C 6 )alkoxy groups, (C-C 6 )alkylthio groups, halo (C,-C 6 alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (C,-C 6 alkylsulfinyl groups, (Cl-
C
6 alkylsulfonyl groups, halo alkylsulfonyl groups, mono (Cl-C 6 alkylamino groups, di alkylamino groups whose (C,-C,)alkyl groups may be the same or different, and alkoxycarbonyl groups, m is an integer of 1 to 5, and each of Z' and Z' is an oxygen atom or a sulfur 'atom) or a salt thereof, provided that when Q1 to Q 5 represent carbon atoms, B represents and R1 represents a hydrogen atom, (C,-C 3 alkyl group, phenyl group or substituted phenyl group, then Ym is not 4trifluoromethyl group, 2-methyl-5-chloro group, 2methyl-4-difluoromethoxy group, 2-methyl-4pentafluoroethyl group and 2-methyl-4-trifluoromethoxy group,.
when Q' to Q' represnt carboh atoms, A' freprxesents (Cl-C 2 alkylene group, B zrepiesents-NR) ]and R represents a hydrogen atom, (Cl-C 2 alkoxycarbonyl 0000.
0-~0 *go 0 33 group or benzyloxycarbonyl group, then Ym is not 2methyl-4-pentafluoroethyl group, 2-methyl-4-heptafluoroisopropyl group and 2-methyl-4-trifluoromethoxy group, and when Q' to Q 5 represent carbon atoms, B represents and R 2 binds to R' to form a 6-membered ring, then Ym is not 2-trifluoromethyl group, 2-methyl- ,group, 2-methyl-4-difluoromethoxy group, 3group and 2-methyl-4pentafluoroethyl group.
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 atom or a fluorine atom. The term "(C 1
-C
6 )alkyl" means a linear or branched alkyl group of 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, nbutyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl or 9.9 the like. The term "halo(C 1 alkyl" means a substi- 9.
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 "(Ci-C,)alkylene" meansa linear or branched alkylene group of 1 to 8 carbon atoms, such as 25 methylene, ethylene, propylene, trimethylene, dimethylmethylene, tetramethylene, isobutylene, dimethylethylene, octamethylene or the like. As "the 5- to 8membered ring which R 5 and R 6 (or R 2 and A 1 or R 1 form by their binding to each other, the 5- to 8membered ring that may contain one or two (or 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" or "the 5- to 8-membered ring which R 5 (or R 6 or
R
7 and R 4 form by their binding to each other, i.e., the 5- to 8-membered ring that may contain two or 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, 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.
The "heterocyclic group" includes, for example, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl 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, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, indole, indoline, chroman, isochroman, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene,benzoxazole, benzothiazole, benzimidazole and indazole.
The salt of the aromatic diamide derivative of the general formula of the present invention includes, for example, inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate and the 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 general formula 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 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 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 or salt thereof of the present invention are aromatic diamide derivatives in which A' is a (Cl-C 4 )alkylene group, B is or
-N(R
4 (wherein R 4 is a hydrogen atom or a (Cl-C 3 )alkyl group), R 1 is a hydrogen atom, a (Cl-C3)alkyl group, a phenyl(C-C 3 )alkyl group, a substituted phenyl(C,- C3)alkyl group, a (Cl-C3)alkylcarbonyl group, a halo(C,- C3)alkylcarbonyl group, a (C-C 3 )alkoxycarbonyl group, a mono (Cl-C3)alkylaminocarbonyl group, a di(C-C 3 alkylaminocarbonyl group whose alkyl groups may be the same or different, a (C,-C3)alkylsulfonyl group, a mono (C-C 3 )alkylaminosulfonyl group, a di(C,-C) alkylaminosulfonyl group whose (C-C 3 )alkyl groups may be the same or different, a di(C-C3)alkoxyphosphono group whose (C-C 3 )alkyl groups may be the same or different, or a di(C-C 3 )alkoxythiophosphono group whose (C- C3)alkyl groups may be the same or different, each of R 2 and R 3 is a hydrogen atom or a (C,-C 3 )alkyl group, each of Q 1 through Q 4 is a carbon atom, X is a halogen atom, a nitro group, a halo(C-C) alkyl group, a halo(C,-
C
6 )alkoxy group or a halo(C,-C)alkylthio group, n is an integer of 0 to 2, Q 5 is a carbon atom or a nitrogen atom, each of Ys, which may be the same or different, is a halogen atom, a (Cl-C3)alkyl group, a halo(C,- C3)alkyl group, a (C,-C3)alkoxy group, a halo(C,- 37 C3)alkoxy group, a halo(Cl-C3) alkylthio group or a halo (C-C3) alkoxyhalo (C-C3) alkoxy group, m is an integer of 1 to 3, each of Z 1 and Z 2 is an oxygen atom; or salts thereof.
The aromatic diamide derivative of the general formula 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, 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.
NH
2
Q
zi
I)
a 1
Q
4 HN2R z Q1
(V)
Q
4
(IV)
(I-1) wherein R 2
R
3
A
1 B, Q 1 through Q 5 X, n, Y, m, Z 1 and Z 2 are as defined above.
An aromatic diamide derivative of the general formula can be obtained by allowing an aromatic 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 and allowing said aromatic imide derivative (IV) to react with an amine of the general formula after or without isolation of the aromatic imide derivative (IV).
General formula (II) general formula (IV) As the inert solvent usable in this reaction, 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, 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 dimethylformamide, dimethylacetamide, etc.; acids such as acetic acid, etc.; dimethyl sulfoxide; 1,3-dimethyl-2imdazolidinone; and the like. These inert solvents may be used singly or as a mixture thereof.
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 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 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 containing 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 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), 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, 0 41 1984, 667, Journal of Chemical Society of Japan, 1973, 2351, German Patent Laid-Open DE-2606982, JP-A-1-90163, etc.
General formula (IV) general formula (I-l) 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 equimolar amounts, though the amine of the general formula 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 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 compound is isolated from the reaction system containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced.
Production process 2.
Ym R 3
NH
(Ill-1) (TI-1)
A!-B-R'
HN-R
2
(V)
O AIB-R' 1 1-R 2 Q 3Q-Q 4 OH R 0 0 1 OH Q N -QY O R (TV-i) A BmRl
HN-R
2 (R Condensing agent
(V)
Condensing agent (ITT-i) Condensing agent (VT -2) (R 2
_H
Condensing agent (VII -1) At B H N-R 2 A' B-Rl Xn1 m O R 50 R (ITT-i) 43 wherein R 2
R
3 B, Q 1 through Q 5 X, n, Y, m, Z 1 and Z 2 are as defined above.
An aromatic diamide derivative of the general formula can be produced by allowing an aromatic carboxylic acid anhydride derivative of the general formula (II-1) to react with an amine of the general formula in the presence of an inert solvent to obtain a phthalamide of the general formula and treating this aromatic amide (VI-2) as follows after or 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 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 general formula (III-1) in the presence of a condensing agent.
Alternatively, an aromatic diamide derivative of the general formula can be produced by allowing an aromatic carboxylic acid anhydride derivative of the 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 and treating the aromatic amide (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 obtain a compound of the general formula (VII-1), which is allowed to react with an amine of the general formula 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 atom, the aromatic amide (VI-1) is condensed with an amine of the general formula in the presence of a condensing agent.
General formula (II-1) general formula (VI-1), or general formula (II-1) general formula (VI- 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 General formula (VII-1) or general formula (VII- 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 General formula (VI-1) general formula (VII-1), 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 process described in J. Med. Chem., 10, 982 (1967).
General formula (VI-1) or general formula (VI-2) general formula (I) The desired compound can be produced by 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 or the general formula (III-1), respectively, in the presence of a condensing agent and an inert solvent. If necessary, 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.
As the condensing agent used in the reaction, any condensing agent used in conventional amide production may be used. There can be exemplified Mukaiyama reagent (2-chloro-N-methylpyridinium iodide), DCC (1,3dicyclohexylcarbodiimide), CDI (carbonyldiimidazole) 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 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, 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-I) or the general formula (VI-2) As to the reaction temperature, the reaction can be carried out at 00C to the boiling point of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it ranges from several minutes to 48 hours.
After completion of the reaction, the desired compound is isolated from the reaction system containing the desired compound by a conventional method, and 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 or a salt thereof 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.
6 2 3 Table 1 (Z'=Z 2 =0 R 3
Q
1
-'Q
5 unless otherwise specified.) Physical No. R2Xn Ym property: Melting point 0
C
1 (CH2 NHCO 2 Pr-i H 3-1 2-Me- 4-CF (CF 3 2 105 2 (CH 2
)NHCO
2 Pr-i H 3-1 2-Me-4-OCF 3 200 3 (CH 2
)NHCO
2 Et H 3-1 H 175 4 (CH2)NHCO 2 Et H 3-I 4-CF 2
CF
3 180
(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 6-1 2-Me- 4-CF (CF 3 2 140 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 C (Me) 2
CH
2
NHCO
2 Me H 3-I 2-Me-4-OCF 3 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 3-1 2-Me 18 C(Me) 2
CH
2
NHCO
2 Et H 6-1 2-Me 120 Table 1 (Oont'd) Physical No. BRR2 nYm property: Melting point 00 C (Me) 2
OH
2
NHOO
2 Et
(OH
2 3
NHOO
2 Bu-t
(OH
2 3
NHCO
2 Me CH (Me) CH 2
NHCO
2 Me
Q
Q
Q
Q
C (Me) 2
OH
2 NHOOPh C (Me) 2
CH
2 NHOOMe O (Me) 2
CH
2 NHOOPr-c C (Me) 2
CH
2 NHCOBu-t
(OH
2 2 NHCOMe
(OH
2 2 NHOOMe OH (Me) OH 2 NHOOMe CH (Me) OH 2 NHOOEt C (Me) 2
CH
2 NHCOEt CH (Me) CH 2 NHCOMe
(OH
2 2 NHCON (Me) 2 CH (Me) CH 2 NHCON (Me) 2 OH (Me) OH 2
NHSO
2 Me OH (Me) OH 2
NHSO
2 Ph OH (Me) OH 2
NHSO
2 Et OH (Me) OH 2 N (Me) SO 2 Me OH (Me) OH 2 N (Me) SO 2 Me 3-1 3-1 3-1 3-1 3-1 6-I 3-1 6-1 3-1 3-1 3-1 3-1 3-I 3-1 3-1 3-1 3-I 3-1 3-1 3-I 3-1 3-1 3-1 3-1 3-1 2-Me-4-0F 2 0F 3 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-00F 3
H
2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 200 145 175 235 225 220 225 240 125 230 160 210 210 140 230 220 215 170 250 110 130 155 100 200 Oont'd Table 1 (Cont 'd) Physical No. -I BR1 R 2 nYm property: point 00 CH (Me) OH 2 N (Me) SO 2 Me OH (Me) OH 2
NHSO
2 N (Me) 2
(OH
2 3 N (Me) 2
(OH
2 3 N (Me) 2 OH (Me) OH 2
NH-
(OMe) 2 OH (Me) CH 2
NH-
(OMe) 2 OH (Me) OH 2
NH-
(OEt) 2
OH
2 2-Me 2 3- Dioxolan-4-yl)
OH
2 2-Me 2 3- Dioxolan-4-yl) 0112- (tetrahydropyran- 4-yl)
OH
2 (tetrahydropyran- 4-yl)
OH
2 OMe OH (Me) CH 2 OMe OH (Me) CH 2 OMe OH (Me) CH 2 0H CH (Me) (0H 2 2 OMe O (Me) 2
CH
2 0H O (OH 2
CH
2 0H 3-1 3-1 3-1 3-1 3-1 3-I 3-1 3-1 3-I 3-1
H
2-Me-4-OF (OF 3 2 2-Me- 4-CF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-OF (OFA) 2 2-Me-4-00F 3 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OFA) 2 250 155 115 175 125 180 170 165 176 145 136 136 137 200 164 210 207 3-01 3-I 3-1 3-01 3-1 3-1 3-1 Oont' d Table 1 (Cont'd) Physical No. -A 1 R2Xn Ym property: I j Melting point OC CH (Me) CH (Me) OH (Me) CH (Me) CH (Me)
(OH
2 2 00H 2
CF
3
(OH
2 2 OEt
(OH
2 2 OEt
(OH
2 2 OEt
(OH
2 20-
(CH
2 2 0Me OH (Me) CH- 2 OEt CH (Me) CH 2 00H 2 Ph CH (Me) CH 2 OPr CH (Me) (OH 2 2 OPr OH (Me) CH 2 0 (OH 2 2 OMe OH (Me) CH 2 OBu-i OH (Me) CH 2 OBu-i CH (Me) (0H 2 2 OBu-i CH (Me) (0H 2 2 OBu-i OH (Me) CH 2 0 (OH 2 2 SMe OH (Me) CH 2 0 (OH 2 2 SEt OH (Me) CH 2 OPh OH (Me) CH 2 OPh OH (Me) CH 2 OPh OH (Me) CH 2 0 (4-01-Ph) OH (Me) CH 2 0 (4-01-Ph) OH (Me) CH 2 0 (3-0F 3 -Ph) OH (Me) 0H 2 0 (3-0F 3 -Ph) OH (Me) OH 2 000Me 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-I
H
3-1 3-1 3-1 3-1 3-1 2-Me-4-OF (CFA) 2 2 -Me- 4-CF (OFA) 2 2 -Me-4-00F 3 2-Ol-4-OCF 3 2-Me-4-OF (OFA) 2 2 -Me- 4-CF (OFA) 2 2 -Me-4 -CF (OFA) 2 2-Me-4-OF (OFA) 2 2 -Me-4 -CF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-OPh 2-Me-4-OF (OF 3 2 4-01 2-Me-4-OF (OF 3 2 2 -Me- 4-CF (OF 3 2 2-Me-4-OF (OF 3 2
H
2 -Me- 4-CF (OF 3 2 2 -Me- 4-CF (OF 3 2 2 6- (Me) 3 2 -Me-4 -CF (OF 3 2 2-Me-4-00F 3 2 -Me-4 -CF (OFA) 2 191 100 164 151 71 171 186 160 146 153 188 113 158 204 168 140 110 130 Amorphous 200 220 100 140 110 1. L L I.
Oont'd 0 0 Table 1 (Oont'd) Physical No. R 2Xn Ym property: Melting point ~O 96 97 98 99 100 101 102 103 104 105 106 107 108 OH (Me) OH 2 000Me C (Me) 2
OH
2 000Me CH (Me) CH 2 0C0N (Me) 2 CH (Me) CH 2 0C0N (Me) 2 CH (Me) CH 2 0CON (Et) 2 C (Me) 2
CH
2 0C0N (Me) 2 C (Me) 2
CH
2 0C0N (Me) 2 CH (Me) CH 2 0C0N (Pr-i) 2 OH (Me) CH 2 0C0N (Me) Ph OH (Me) 0H 2 000- N (-0H 2 0H 2 00H 2 0H 2 OH (Me) CH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000- N (-0H 2 0H 2 0H 2 0H 2 OH (Me) OH 2 000NHPr-i C (Me) 2
OH
2 000NHEt OH (Me) OH 2 000NHMe OH (Me) OH 2 000NHMe OH (Me) OH 2 000NHPr OH (Me) OH 2 000NHPr OH (Me) OH 2 000NHPr-i OH (Me) OH 2 000NHPr-i OH (Me) OH 2 000NHOH 2 Ph OH (Me) OH 2 000NHOH 2 Ph 3-1 3-1 3-1 3-1 3-I 3-1 3-I 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-1 2-Me- 4-00F 3 2 -Me- 4-CF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-00F 3 2 -Me- 4-CF (OFA) 2 2 -Me- 4-CF (OFA) 2 2-Me-4-00F 3 2-Me-4-OF (OFA) 2 2 -Me- 4-OF (OFA) 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me- 4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2 -Me- 4-CF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me- 4-00F 3 2-Me-4-OF (OF 3 2 2-Me- 4-00F 3 2-Me-4-OF (OF 3 2 2-Me- 4-00F 3 155 180 100 140 190 115 150 100 105 255 185 220 Amorphous 130 225 190 200 175 205 170 215 175 190 Oont'd Table 1 (Cont'd) Physical No. -A'-B-Rl R 2Xn Ym property: Melting point 0
C
109 CH(Me)CH 2 OCONHPh H 3-1 2-Me-4-CF (CF 3 2 190 110 CH(Me)CH 2 OCONHPh H 3-1 2-Me-4-OCF 3 230 111 CH (Me) CH 2 O- H 3-I 2-Me-4-CF (CF 3 2 115 (OMe) 2 112 CH (Me)0CH 2 0- H 3-I 2-Me-4-CF (CF 3 2 140 P (OEt) 2 113 CH (Me) CH 2 O- H 3-1 2-Me-4-OCF 3 115 (OEt) 2 114 CH (Me) CH 2 O- H 3-1 H 125 (OEt) 2 115 CH (Me) CH 2 O- H 3-I 2-Me (OEt) 2 116 C (Me) 2
CH
2 0- H 3-I 2-Me-4-CF (CFA) 2 120 (OMe) 2 117 CH (Me) CH 2 O- H 3-I 2-Me-4-CF(CF 3 2 Amorphous P (OEt) 2 118 CH (Me) CH 2 O- H 3-I H Amorphous (OEt) 2 Cont'd Note: In the table, Q denotes the following group: -OH NCO 2
EI
Table 1 (Cont'dc) TT Physical No. -A RI Xn Ym property: Melting point OC 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 CH (Me) CH 2
OCOCF
3 C (me) 2
CH
2
OCOCF
3 C (Me) 2
CH
2
OCOCF
3 C (Me) 2
CH
2
OCOCF
3 CH (Me) CH 2 000-Ph C (Me) 2
CH
2 000-Ph CH (Me) CH 2 OCO- (3-Pyr) C (Me) 2
CH
2 OCO- (3-Pyr)
(CH
2 2 OCONHEt
(CH
2 2 OCONHEt C (Me) 2
CH
2 OCONHPr-n C (Me) 2
CH
2 OCONHPr-n CH (Me) CH 2 OCONHPr-i C (Me) 2
CH
2 CONHPr-i CH (Me) CH 2 OCONHPr-c CH (Me) CH 2 OCONHPr-c C (Me) 2
CH
2 OCONHPr-c C (Me) 2
CH
2 OCONHPr-c C (Me) 2
CH
2 OCONHBU-n C (Me) 2
CH
2 OCONHBu-s CH (Me) CH 2 OCONHBu-t CH (Me) CH 2 OCONHBu-t 3-NO 2 3-1 3-I 6-1 3-1 3-1 3-1 3-1
H
H
3-1 3-I 3-1 3-1 3-I 3-I
H
3-1 3-1 3-1 3-1 3-1 2-Me-4-CF (CE 3 2 2-Me-4-CF (CE 3 2 2-Cl-4-CF (CE 3 2 2-Cl-4-CF (CE 3 2 2-Me-4-CF (CF 3 2 2-Me-4-CF (CE 3 2 2-Me-4-CF (CE 3 2 2-Me-4-CF (CE 3 2 2-Me-4-CF 2
CF
3 2-Me-4-CF (CF 3 2 2-Me-4-CE (CF 3 2 2-Cl-4-CF (CEF) 2 2-Me-4-CF (CFA) 2 2-Me-4-CF (CF 3 2 2-Me-4-CF (CFA) 2 2-Me-4-OCF 3 2-Me-4-CF (CEF) 2 2-Me-4-CE (CE 3 2 2-Me-4-CE (CE 3 2 2-Me-4-CF (CE 3 2 2-Me-4-CE (CF 3 2 2-Cl-4-CF (CF 3 2 209 190 150 52 113 220 200 114 212 176 231 215 190 Cont'd Table 1 (Cont'Id) Physical No. 2 Xn Ym property: Melting point C 141 142 143 144 145 146 147 148 149 150 151 152 153 C (Me) 2
OH
2 0C0NHBu-c CH (Me) OH 2 000NH-
CH
2
C=CH
2 C (Me) 2
CH
2
OCONH-
SCH
2
C=CH
2 C (Me) 2
CH
2
OCONH-
OH
2 O=0H 2 C (Me) 2
OH
2 000NH-
CH
2
C=CH
2 CH (Me) CH 2
OCONH-
CH
2
CO=CH
C (Me) 2
CH
2 000NH-
CH
2
C=-CH
OH (Me) CH 2 0C0NHCH 2
CF
3 C (Me) 2
CH
2 000NHCH 2
CF
3 C (Me) 2
CH
2 000NHOH 2 C COMe C (Me) 2
CH
2 000NHCH 2 CON (Et) 2 C (Me) 2
CH
2 000NHCH 2 -Ph C (Me) 2
CH
2 0C0NHCH 2 -Ph 3-1 3-1
H
3-1 3-1 3-1 3-1 3-I 3-1 3-1 3-1 3-1 3-1 2-Me--4-CF (OF 3 2 2-Me-4-CF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OCF 3 2-Me-4-OF (OF 3 2 2-Me-4-OCF 3 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-CF (OF 3 2 2-01-4-OF (OF 3 2 189 174 181 196 124 196 170 185 -Cont'd Table 1 (Oont'd) 1 1 2 IPhysical No. R 2 Xn Ym property: I point 00 154 155 156 157 158 159 160 161 162 163 164 OH (Me) CH 2 0C0N (OH 3
CH
2 -Ph OH (Me) OH 2 000NHOH 2 (2-Cl-Ph) OH (Me) OH 2 000NHOH 2 (3-01-Ph) OH (Me) OH 2 000NHOH 2 (4-01-Ph) CH (Me) CH 2 000NHOH 2 (2-Me-Ph) OH (Me) OH 2 000NHOH 2 (4-Me-Ph) OH (Me) OH 2 000NHOH 2 (2-OMe-Ph) OH (Me) OH 2 000NHOH 2 (4-OMe-Ph) OH (Me) OH 2 000NHOH 2 3 -Ph) OH (Me) OH 2 000NHOH 2 (2-Pyr) OH (Me) OH 2 000NHOH 2 (3-Ol-5-0F 3 -Pyr) 3-1 3-1 3-1 3-1 3-1 3-1 3-1 3-I 3-1 3-I 3-1 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Ive-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Ne-4-CF (OF 3 2 2-Me-4-OF (CFA) 2 2-Me-4-CF (OF 3 2 2-Me-4-OF (OF 3 2 2 -Me-4-OF (CFA 2 2-lMe-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 Paste 181 170 188 178 186 a JJ L Oont' d Table 1 (Oont'd) TPhysical No. -BRR2 nYn property: Melting point 00 165 166 167 168 169 170 171 172 173 174 CH (Me) OH 2 000NHOH 2 (3-Pyr) CH (Me) OH 2 000NHOH 2 (6-Ci-Pyr)] CH (Me) CH 2 000NHOH 2 (4-Pyr) OH (Me) OH 2 000NHOH 2 (4-Pyr) OH (Me) CH 2 000NHOH 2 15- 0F 3 3, 4-Triadiazol -2-yl] OH (Me) CH 2 0C0NH (OH 2 2 -OMe OH (Me) CH 2 0C0NH (OH 2 2 -OMe C (Me) 2
CH
2 0C0NH (OH 2 2 -OMe C (Me) 2
CH
2 0C0NH (OH 2 2 OMe OH (Me) CH 2 0C0NH (OH 2 3 -OMe 3-1 3-1
H
3-1 3-1 3-1 3-1 3-1 3-1 3-1 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (CFA 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OCF 3 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 137 140 169 Paste 231 184 135 I I Oont'd Table 1 (Oont'd) Physical No 1A--R 2 nYprety Melting point 00 175 176 177 178 179 180 181 182 183 184 185 C (Me) 2
CH
2 0C0NH (OH 2 3 -OMe CH (Me) CH 2 0CONH (OH 2 2 -SMe CH (Me) CH 2 0C0NH (OH 2 2 SMe C (Me) 2
CH
2 0C0NH (CH 2 2 SMe O (Me) 2
CH
2 0C0NH (OH 2 2 -SMe OH (Me) CH 2 0CONH (OH 2 2 SOMe CH (Me) CH 2 0C0NH (OH 2 2 SOMe CH (Me) CH 2 0C0NH (OH 2 3 SMe OH (Me) CH 2 0C0NH (OH 2 3 -SMe C (Me) 2
CH
2 0C0NH (OH 2 3 SMe C (Me) 2
CH
2 0C0NH (OH 2 3 SMe 3-1 3-1 3-I 3-1 3-1 3-1 3-1 3-1 3-I 3-1 3-1 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me -4-00 F 3 2-Me-4-OF (OF 3 2 2-Me-4-OCF 3 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me- 4-OOHF 2 171 176 178 I
I
Oont'd Table 1 (Oont 'd) Physical No. Xn Ym property: Melting point 00 186 187 188 189 190 191 192 193 194 195 196 197 198 199 200 C (Me) 2
CH
2 0C0NH (CH 2 3
-SO
2 Me C (Me) 2
CH
2 0C0NH (OH 2 3 S 2 Me CH (Me) OH 2 00 NHEt C (Me) 2
CH
2 00 NHEt CH (Me) CH 2 0P (OMe) 2 OH (Me) CH 2 0P (OMe) 2
(OH
2 3 000NHEt
(CH
2 3 000NHEt CH (Me) (CH 2 2 000NHEt CH(Me) (CH 2 2 000- N (Et) 2 CH (Me) (CH 2 2
OCONH-
CH
2 -Ph C (Me) 2 (CH 2 2 OCONHMe
(OH
2 4 000NHEt
(OH
2 4 000NHPr-i CH (Me) (CH 2 3 0C0NHEt 3-1 3-1 3-1 3-1 3-I
H
3-1 3-1 3-1 3-1 3-I 3-1 3-1 3-1 3-I 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me--4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OCF 3 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-CF (OFA) 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OFA) 2 2-Ne-4-OF (OFA) 2 166 76 132 U J J Oont'd Table 1 (Oont'd) Physical No. -A-KlR 2 Xn Ym property: Melting point 00 201 202 203 204 205 206 207 208 209 210 211 212 213 214 215 216 217 218 CH (Me) (OH) 3 000- N (Et) 2 OH (Me) (OH 2 3 000NH-
CH
2 -Ph C (Me) 2 (CH 2 3 OOONHll'e
(CH
2 5 OCONHEt
(CR
2 5 OCONHEt OH (Me) (OH 2 4 OCONHEt CH (Me) (0H 2 4 000- N (Et) 2 CH (Me) (OH 2 4 0C0NH-
CH
2 -Ph C (Me) 2 (OH 2 4 0C0NHMe CH (Me) CH 2 OCONHEt OH (Me) OH 2 000NHEt OH (Me) CH 2 000NHOH 2 -Ph C (Me) 2
OH
2 000NHMe OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHOH 2 -Ph 3-1 3-I 3-I
H
H
3-I 3-1 3-I 3-1 3-F 3-F 3-F 3-F 3-Cl 3-Cl 3-Cl 3-01 3-01 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-F 2
OF
3 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-CF (OFA) 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-0F 2 0F 3 2-Me-4-OOHF 2 2-Me-4-00F 3 2-Me--4-OF (CFA 2 138 136 178 179 131 99 145 188 Oont'd Table 1 (Cont'd) Physical No. -A R 2 Xn Ym property: Melting point 00 219 220 221 222 223 224 225 226 227 228 229 230 231 232 233 O (Me) 2
OH
2 000NHMe OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt CH (Me) OH 2 000NHEt OH (Me) CH 2 000NHEt OH (Me) OH 2 000NHOH 2 -Ph O (Me) 2
OH
2 000NHT'e OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHOH 2 -Ph OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) CH 2 000NHEt 3-01 4-01 4-01 3-Br 3-Br 3-Br 3-Br 4-1 4-1 3, 4- 012 3,4- 012 3,4- 012 3-Br -4-01 3,4- Br 2 3-1- 4-C1 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OOF 3 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-CF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-CF (CFA 2 2-Me-4-OF (OF 3 2 164 196 139 193 I .2 Oont'd Table 1 (Oont'd) No. -B-Rl Physical property: Melting point 00 1 4- 234 235 236 237 238 239 240 241 242 243 244 245 246 247 248 249 250 251 252 CH (Me) OH 2 000NHEt CH (Me) OH 2 000NHEt CH (Me) CH 2 000NHOH 2 -Ph CH (Me) CH 2 0C0N (Et) 2 C (Me) 2
OH
2 0C0NHMe OH (Me) OH 2 000NHEt CH (Me) OH 2 000NHOH 2 -Ph CH (Me) CH 2 0C0N (Et) 2 C (Me) 2
CH
2 000NHMe OH (Me) OH 2 OCONHEt OH (Me) OH 2 000NHEt OH (Me) CH 2 000NHOH 2 -Ph OH (Me) CH 2 0C0N (Et) 2 O (Me) 2
OH
2 000NHMe OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt 3, 4-12 3-NO 2 3 -NO 2 3 -NO 2 3-NO2 3-OF 3 3-OF 3 3-0 F 3 3-OF 3 4-0 F 3 3-00F 3 3-00F 3 3-OCF 3 3-OCF 3 3-SMe 3-SOMe 3-
SO
2 Me 3-S OF 3 3-
SOCF
3 2-Me-4-OF (OFA) 2 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (CFA 2 2-Me-4-OF (OF 3 2 194 151 178 203 182
I
Oont'ci Table 1 (Cont' d) No. -A--lR2 Xn Ym property: Melting point 00 253 254 255 256 257 258 CH (Me) CH 2 0C0NHEt CH (Me) OH 2 000NHEt CH (Me) OH 2 000NHEt OH (Me) OH 2 0C0NHEt OH (Me) CH 2 000NHEt OH (Me) CH 2 0C0NHEt 3-
SO
2
CF
3 3-
C=-CH
3 C-Bu-t 3-C= C-Ph 3-C=- 0-C F 3 3-C= C-Si- (Me) 3 3-OH=
CH-CH=
OH- 4 3-OH=
CH-CH=
CH- 4 3-00F 2 -0-4 2-Me-4-CF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-O0F 3 2-Me-4-CF (OF 3 2 2-Me-4-00F 3 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OCF 3 2-Me-4-CF (OF 3 2 2 59 1 CH (Me)OCH 2 000NHEL 207 185 2 60 1 CH (Me)OCH 2 000NHEt 2 61 1 CH (Me) CH 2 000NHEt .1 1 Cont'd Table 1 (Cont'd) Physical No. R 2 Xn Ym property: ~Melting point 00 2 62 1 CH (Me) CH 2 0C0NHEt 263 264 265 266 267 268 269 270 271 272 273 274 275 276 277 OH (Me) CH 2 000NHEt CH (Me) CH 2 000NHEt CH (Me) OH 2 000NHEt CH (Me) CH 2 OCONHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHOH 2 -Ph OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt O (Me) 2 0H 2 00NHllve OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 0C0NHEt 3-00 F 2
OF
2 0 4 3-1 3-1 (R 3 3-1 3-1 3-1 3-1 3-I 3-1 3-1 3-1 3-1 3-I 3-1 3-1 3-1 2-Me-4-OF (OF 3 2 2-Me-4-Ol 2-Me-4-Ol =Me) 2-Me-4-0F 3 2-01-4-OF 3 2-Me-4-0F 2 0F 3 2-Me-4-0F 2 0F 3 2-Et-4-F 2 0F 3 2- F- 4-0F 2
OF
3 2-01-4-OF 2
OF
3 2-Me-4-0 3
F
7 -n 2-Me-4-C 4
F
9 -n 2-01-4-OF (OF 3 2 2-OMe-4-OF (OF 3 2 2-Me-4-OF (OF 3 0 F 2 C0F 3 2-Me-3-F-4- OF (OF 3 2 202 Paste 217 208 163 168 179 176 184 173 140 168 Oont' d Table 1 (Cont'cld) Physical No. -A -B-Rl R 2 Xn Ym property: Melting point 00 278 279 280 281 282 283 284 285 286 287 288 289 290 291 292 293 294 OH (Me) OH 2 0C0NHEt OH (Me) CH 2 000NHEt CH (Me) OH 2 0C0NHEt CH (Me) OH 2 000NHEt CH (Me) OH 2 000NHEt CH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHOH 2 -Ph OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHOH 2 -Ph OH (Me) OH 2 000NHEt 3-1 3-1 3-1 3-1 3-1 3-1 3-1
H
3-I 3-1 3-1 3-1 3-I 3-1 3-1
H
3-1 2-Me-3-OMe-4-
OF(OF
3 2 2-Me-4-O (OF 3 2- OE t 2-Br-4-00F 3 2-01-4-00 F 3 2-Me -4-00 F 2
OF
3 2-Me-4-00 3
F
7 -n 2-Me-4-OOHF 2 2-Me-4-OF 2
OHF
2 2-Me-4-OOF 2 OHO1F 2-Me-4-OOF 2
OHF-
OF
3 2-Me-4-OOF 2
OHF-
O0F 3 2-Me-4-0- (3-01-5 -0F 3 -Pyr-2-yl) 2-Me-4-SOF 3 2-Me-4-SOOF 3 2-Me -4-S 020F 3 3-OCF 2 0-4 3-OCF 2 0-4 139 193 189 185 141 193 182 168 200 203 142 I i Oont'd Table 1 (Oont'd) Physical No. Xn Ym property: Melting point 00 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310 311 312 313 314 315 316 OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) CH 2 000NHEt OH (Me) OH 2
NHOHO
O (Me) 2
OH
2
NHOHO
OH (Me) (OH 2 2
NHOHO
C (Me) 2 (OH 2 2
NHOHO
OH (Me) OH 2
NHOF
3 O (Me) 2
OH
2
NHCOF
3 O (Me) 2
OH
2
NHCOF
3
(OH
2 2 NHOOMe
(OH
2 2
NHCOOH
2 -Ph
(OH
2 2 NHOO-Ph OH (Me) OH 2 NHO NHEt O (Me) 2
OH
2
NHSO
2
OF
3 OH (Me) OH 2
NHSO
2
OF
3 O (Me) 2
OH
2
NHS
2 -Ph OH (Me) OH 2
NHSO
2 -Ph 3-1 3-1
H
3-1 3-1 3-1 3-1 3-I 3-I 3-1 3-1 3-1 3-I 3-I
H
H
H
H
3-1 3-1 3-I 3-1 2-Me-3-00F 2 0-4 2 -Ol-3-O0F 2 0-4 3-00F 2 0F 2 0-4 3-0 F 2 0F 2 0-4 3-00 F 2
OF
2 -4 3-OF 2
OF
2
OF
2 -4 3-OF 2
OF
2
OF
2
OF
2 -4 2 -Me-4 -CF (OFA) 2 2-Me-4-OF (OF 3 2 2 -Me-4 -CF (OF 3 2 2-Me-4-OF (OF 3 2 2 -Me-4 -CF (OF 3 2 2 -Me-4-OF (CFA 2 2-Me-4-00F 3 2 -Me-4 -CF (OF 3 2 2 -Me-4 -CF (OF 3 2 2 -Me-4 -CF (CFA 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (CFA 2 2-Me-4-OF (OF 3 2 112 108 191 185 Oont' d Table 1 (Cont'd) Physical No. R 2 Xn Ym property: Melting point 0
C
317 CH (Me) CH 2 NH (Me) SO 2 Me H 3-I 2-Cl-4-CF (CFA) 2 190 318 (CHA 2 N (Me) OMe H 3-1 2-Me-4-CF (CFA) 2 319 (CHA) 3 N (Me) OMe H 3-1 2-Me-4-CF (CFA) 2 91 320 (CH 2 3 N (Me) OMe H 3-I 2-Me-4-OCF 3 154 321 (CHA) 2 NHCOMe Me H 2-Me-4-CF (CFA) 2 187 322 C (Me) 2
CH
2 OCONHMe H 3-I 2-Me-4-CF (CFA) 2 180 Table 2 (Z'=Z 2
R=
3
H
R 2=p 3
=H)
Melting 1o R1 Q1 2' 3' 4' Q 00pon No -AB-R Q Q Q X Ym oin 2-1 2-2 2-3 2-4 2-6 2-7 2-8 2-9 2-10 2-11 2-12 2-13 2-14 2-15 2-16 2-17 2-18 2-19 OH (Me) OH 2 000NHEt OH (Me) CH 2 0C0N (Et) 2 OH (Me) OH 2 000NHOH2Ph C (Me) 2
CH
2 000NHMe OH (Me) OH 2 000NHEt CH (Me)OCH 2 0C0N (Et) 2 OH (Me) OH 2 0C0NHOH 2 Ph O (Me) 2
OH
2 000NHMe OH (Me) OH 2 000NHEt OH (Me) CH 2 0C0N (Et) 2 OH (Me) OH 2 000NHOH 2 Ph C (Me) 2
OH
2 000N He OH (Me) OH 2 000NHEt OH (Me) CH 2 0C0N (Et) 2 OH (Me) OH 2 000NHOH 2 ph C (Me) 2
OH
2 000NHMe OH (Me) OH 2 000NHEt CH (Me)OCH 2 0C0N (Et) 2 C (Me) 2
CH
2 000ONHMe 3-01 3-01 3-01 3-01
H
3-Br
H
H
H
H
H
H
H
H
H
3-1
H
H
H
2-Me-4-X1F 3 2-Me-4-0F 2 0F 3 2-Me-4-0F 2
CF
3 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-0F 3 2-01-4 -OCF 3 2-Me-4-0F 2 0F 3 2-Me-4-CF 3 2-Me-4-F 2 0F 3 2-Me-4-OF (OF 3 2 2-Et-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-01-4-OF 3 2-Me-4 -00F 3 2-Me-4-F 2 0F 3 2-Me-4 -OCF 3 2-Me-4-F 2 0F 3 2-Me-4-OF (OF 3 2 100 94 103 Oont'd Table 2 (Cont'd) Melting No -A-B-R Q Q' d Q Xn Ym point 2-20 2-21 2-22 2-23 2-24 2-25 2-26 2-27 2-28 2-29 2-30 2-31 2-32 2-33 2-34 2-35 2-36 2-37 2-38 2-39 2-40 2-41 2-42 2-43 CH (Me) CH 2 OOONI-~t OH (Me) CH 2 0C0N (Et) 2 OH (Me) OH 2 000NHOH 2 Ph C (Me) 2
OH
2 000NHMe OH (Me) CH 2 000NHEt OH (Me) CH 2 0C0N (Et) 2 OH (Me) OH 2 000NHOH 2 Ph O (Me) 2
OH
2 0C00NIMe OH (Me) CH 2 0C0N (Et) 2 CH (Me) CH 2 0C0N (Et) 2 OH (Me) OH 2 000NHEt OH (Me) OH 2 000NHEt OH (Me) CH 2 0C0N (Et) 2 CH (Me)OCH 2 0C0N (Et) 2 OH (Me) OH 2 000NHOH 2 Ph O (Me) 2
OH
2 000NEMe OH (Me) OH 2
NHOO
2 Et OH (Me) OH 2 NHOOEt OH (Me) OH 2
NHSO
2 Et OH (Me) OH 2 000NHEt OH (Me) CH 2 0C0N (Et) 2 OH (Me) OH 2 000NHOH 2 Ph O (Me) 2
OH
2 000NHMe OH (Me) OH 2 0C0NHEt 3-1 3-1 3-I 3-1 3-1 3-1 3-1 3-I 3-I 6-1 3-01 3-Br 3-1 6-1 3-1 3-1 3-1 3-1 3-I 3-I 3-I 3-1 3-1 3-1 2-Me-4-0F 3 2-01-4-OF 3 2-Me-4-OCX 3 2-01- 4-OF 3 4-CF 2
CF
3 2-Me-4-F 2 0F 3 2-O1-4-F 2 0F 3 2-cO4e-4-CF 2
CF
3 4-OF (0F 3 2 4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-OF (OFA) 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-Me-4-OF (OF 3 2 2-01-4-OF (OF 3 2 2-01-4-OF (OF 3 2 2-01-4-OF (OF 3 2 2-01-4-OF (OF 3 2 2-OMe-4-OF (OF 3 97 119 204 140 176 188 Oont'd Table 2 (Cont'd) Melting No Q' d Q Q Q Xn Yin point 2-44 2-45 2-46 2-47 2-48 2-49 2-50 2-51 2-52 2-53 2-54 2-55 2-56 2-57 2-58 2-59 2-60 2-61 2-62 2-63 2-64 2-65 2-66 2-67 OH (Me) CH 2 0C0N (Et) 2 OH (Me) OH 2 000NHOH 2 Ph C (Me) 2
CH
2 000NHMe OH (Me) CH 2 OOONI-~t OH (Me) CH 2 00N (Et) 2 OH (Me) CH 2 0C0N (Et) 2 OH (Me) OH 2 000NHOH 2 Ph C (Me) 2
CH
2 000NHMe C (Me) 2
CH
2 000NfMe OH (Me) OH 2
NHOO
2 Me OH (Me) OH 2 NHCa~e OH (me) OH 2
NHSO
2 N (Me) 2 OH (Me) OH 2 000NHMe OH (Me) CH 2 0C0N (Et) 2 OH (Me) OH 2 000NHOH 2 Ph O (Me) 2
OH
2 000NEMe OH (Me) OH 2 000NHEt CH (Me) CH 2 0C0N (Et) 2 OH (Me) OH 2 000NHOH 2 Ph C (Me) 2
OH
2 000NHMe OH (Me) OH 2 000NHEt OH (Me) CH 2 00N (Et) 2 OH (Me) OH 2 000NHOH 2 Ph O (Me) 2
OH
2 0C0NHMe 3-1 3-1 3-I 3-1
H
:3-1 3-1 3-1 6-1 3-I 3-I 3-1 3-I 3-I 3-I 3-1 3-I 3-I 3-I 3-1 3-I 3-1 3-I 3-1 2-a~e-4-OF (OF 3 2 2-Ok~e-4-OF (OF 3 2 2-C12e-4-OF (OF 3 2 2-Me-4-OCH (OFA) 2 2-Me-4-0CXH (OF 3 2 2-Me-4-OCH (OF 3 2 2-Me-4-OCH (OF 3 2 2-Me-4-0GCH (OF 3 2 2-Me-4-CH (OF 3 2 2-Me-4-OCH (OF 3 2 2-Me-4-CH (OF 3 2 2-Me-4-OCH (OF 3 2 2-me-4-cHF 2 2-Me-4-CHF 2 2-Me-4-OHF 2 2-Me-4-OF 2
HF
2 2-Me-4-OF 2
HF
2 2-Me-4-OCXF 2
OHF
2 2-Me-4-OF 2
HFCF
3 2-Me-4-OF 2
HFCF
3 2-Me- 4-OF 2
HFCF
3 2-Me-4-OF 2
HFCF
3 2-Me-4-OF 2
HECF
3 2-Me-4-OF 2
HFCF
3 197 168 226 210 213 222 Oont' d Table 2 (Cont'd) Melting No BRQ Q Q Q' Q Xn Ym point 2-68 CH (Me) CH 2 OCON~t N C C C N 3-1 2-Me-4-OCF 2 2-69 CH(Me)CH 2 0C0N(Et) 2 C N C C N 3-1 2-Me-4-CF 2
CF
3 2-70 CH (Me) CH 2 0C0NHCH 2 Ph C C N C N 3-1 2-Me-4-CF(CF 3 2 2-71 C (Me) 2
CH
2 0C0NFI'e C C C N N 3-I 2-Cl-4-CF(CF 3 2 2-72 CH(Me)CH 2 0C0NH C C C C N 3-1 2-Me-4-OH(CF 3 2 201
-CH
2 (C24e) -Ph) 2-73 CH (Me) CH 2 OP(=S) C C C C N 3-1 2-Me-4-OCH(CF 3 2 157 (OMe) 2 2-74 CH (Me) CH 2 OP(=S) C C C C N 6-1 2-Me-4-CH-(CFA) 2 134 Table 3 shows 1 H-N'R data of compounds having a physical property expressed by the word "amorphous" in Table 1.
71' Table 3 No. 'H-NNR[CDCl 3 /TMS, 5 values (ppm)] l.33(d,3H), 2.37(s,3H), 3.91(dd,lH), 3.96(dd,lH), 4.55(m,lH), 6.78(cl,2H), 6.94(dd,l{), 7.22(m,3H), 7.39(d,lH), 7.41(s,14), 7.81(d,lH), 7.99(d,lH), 8.21(d,1H) 8.41(s,lH).
98 l.17(d,3H), 1.75-l.90(m,4H), 2.40(s,3H), 3.10-3.42 (in, 44), 4.02 (dd,M1) 4.22 (dd, lH) 4.32(m, 1H) 6.89(d,1H), 7.22(dd,1H), 7.42(s,1H), 7.44(ci,1), 7.81(d,lH), 7.97(ci,1H), 8.34(ci,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,lH), 6.79(d,1H), 7.23(dd,1H), 7.41(s,1H), 7.43(cl,1H), 7.81(d,1H), 7.99(cl,lH), 8.31(cl,1H), 8.42(s,1H).
Agricultural and horticultural chemicals, in particular, agricultural and horticultural insecticides, which contain as an active ingredient the aromatic diamide derivative of the general formula (I) or salt thereof of the present invention are suitable for controlling various insect pests such as agricultural insect pests, forest insect pests, horticultural insect pests, stored grain insect pests, sanitary insect pests, nematodes, etc., which are 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 (Adoxophyes Manchurian fruit moth (Grapholita inopinata), oriental fruit moth (Grapholita molesta), soybean pod borer (Leguminivora glycinivorella), mulberry leafroller (Olethreutes mori), tea leafroller (Caloptilia thevivora), Caloptilia sp. (Caloptilia zachrysa), apple leafminer (Phyllonorycter ringoniella), pear barkminer (Spulerrina astaurota), common white (Piers rapae crucivora), tabacco budworm (Heliothis codling moth (Laspey resia pomonella), 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 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.; 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 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 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 vigintioctopunctata), adzuki bean weevil (Callosobruchus chinensis), vegetable weevil (Listroderes costirostris), maize weevil (Sitophilus zeamais), boll weevil (Anthonomus gradis gradis), rice water weevil (Lissorhoptrus oryzophilus), cucurbit leaf beetle (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.), 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.), 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 nematode (Meloidogyne citrus nematode (Tylenchulus semipenetrans), Aphelenchus sp.
(Aphelenchus avenae), chrysanthemum foliar nematode (Aphelenchoides ritzemabosi), etc.
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 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 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 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 conveniently usable forms according to an ordinary manner for preparation of agrochemicals.
That is, the aromatic diamide derivative of the general formula or a salt thereof and, 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 powder, granules, dust, tablets or the like through dissolution, dispersion, suspension, mixing, impregnation, adsorption or sticking.
The inert carrier usable in the present invention may be either solid or liquid. As a material 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, clays kaolin, bentonite, and acid clay), talcs talc and pyrophyllite), silica powders or flakes diatomaceous earth, silica sand, mica and white carbon [synthetic, high-dispersion silicic acid, also called finely divided hydrated silica or hydrated 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 inorganic or mineral powders, chemical fertilizers 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 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 methanol, ethanol, isopropanol, butanol and ethylene glycol), ketones acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone), ethers ethyl ether, dioxane, Cellosolve, dipropyl ether and tetrahydrofuran), aliphatic hydrocarbon (e.g.
kerosene and mineral oils), aromatic hydrocarbons (e.g.
benzene, toluene, xylene, solvent naphtha and alkylnaphthalenes), halogenated hydrocarbons dichloroethane, chloroform, carbon tetrachloride and chlorobenzene), esters ethyl acetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate), amides dimethylformamide, diethylformamide and dimethylacetamide), nitriles acetonitrile), and dimethyl sulfoxide.
The following are typical examples of the adjuvant, which are used depending upon purposes and 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 polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resonates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalene sulfonic acid condensation products, ligninsulfonates and higher alcohol sulfate esters.
Further, to stabilize the dispersion of a 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, carboxymethyl cellulose, gum arabic, poly(vinyl alcohol)s, 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.
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.
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 0 78 weight per 100 parts of the agricultural and horticultural 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 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 insecticide of the present invention is used to control a 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 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 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 range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, (in terms of the compound as active ingredient) per ares depending upon purposes.
The agricultural and horticultural chemical, in particular, agricultural and horticultural insecticide of the present invention may be used in admixture with other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, biotic pesticides 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 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 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, Mecarbam, Vamidothion, Thiometon, Disulfoton, Oxydeprofos, Naled, Methylpatathion, Fenitrothion, Cyanophos, Propaphos, Fenthion, Prothiofos, Profenofos, Isofenphos, Temephos, Phenthoate, Dimethylvinphos, Chlorfenvinphos, Tetrachlorvinphos, Phoxim, Isoxathion, Pyraclofos, Methidathion, Chlorpyrifos, Chlorpyrifosmethyl, Pyridaphenthion, Diazinon, Pirimiphosmethyl, Phosalone, Phosmet, Dioxabenzophos, Quinalphos, Terbuphos, Ethoprophos, Cadusafos, Mesulfenfos, DPS 08 (NK-07 95), Phosphocarb, Fenamiphos, Isoamidophos, Fosthiazate, Isazophos, Ethoprophos, Fostietane, Dichiofenthion, Thionazii, Suiprofos, Fensulfothion, Diamidafos, Pyrethrin, Allethrin, Prallethrin, Resmethrin, Permethrin, Tefluthrin, Bifenthrin, Fenpropathrin, Cypermethrin, ax-Cypermethrin, Cyhalothrin, X-Cyhalothrin, Deltamethrin, Acrinathrin, Fenvalerate, Esfenvalerate, Flucythrinate, Fluvalinate, Cycloprothrin, Ethofenprox, Halfenprox, Silafluofen, Fluvalinate, Nethomyl, Oxamyl, Thiodicarb, Aldicarb, Alanycarb, Cartap, Metolcarb, Xylylcarb, Propoxur, Phenoxycarb, Fenobucarb, Ethiophencarb, Fenothiocarb, Bifenazate, BPMC, Carbaryl, Pirimicarb, Carbofuran, Carbosulfan, Furathiocarb, Benfuracarb, Aldoxycarb, Diafenthiuron, Diflubenzuron, Teflubenzuron, Hexaflumuron, Novaluron, Lufenuron, Fluffenoxuron, Chlorfluazuron, Fenbutatin oxide, tricyclohexyltin hydroxide, sodium oleate, potassium oleate, Methoprene, Hydropreie, Binapacryl, Amitraz, Dicofol, Chrorobenzilate, Bromopropylate, Tetradifon, Bensultap, Benzoximate, Tebufenozide, Methoxyfenozide, Chromafenozide, Propargite, Acequinosyl, Endosulfan, Diofenolan, Chiorfenapyl, Fenpyroximate, Tolfenpyrad, Fipronil, Tebufenpyrad, Triazamate, Etoxazole, Hexythiazox, nicotine sulfate, Nitenpyram, Acetamiprid, Thiacloprid, Imidacloprid, Thiamethoxam, Clothianidin, Nidinotefuran, Fluazinam, Pyriproxyf en, Hydrarnethylnon, Pyrimidifen, Pyridaben, Cyromazin, TPTC (tripropyl isocyanurate), Pymetrozin, Clofentezin, Buprofedin, Thiocyclam, Fenazaquin, Chinomethionate, Indoxacarb, Polyractin complexes, Milbemectin, Abamectin, Emamectin-benzoate, Spinosad, BT (Bacillus 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 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, Thiophanate methyl, Benomyl, Iminoctadin acetate, Iminocutadin albecylate, Mepronil, Flutolanil, Pencycuron, Furametpyl, Thifluzamide, Metalaxyl, Oxadixyl, Carpropamid, Dichiofluanid, Flusulfamide, Chiorothalonil, Kresoxim-methyl, Fenoxanil (NNF-942 Himexazol, Etridiazol, Fluoroimide, Procymidone, Vinclozolin, Iprodione, Triadimefon, Triflumizole, Bitertanol, Ipconazole, Fluconazole, Propiconazole, Diphenoconazole, Myclobutanil, Tetraconazole, Hexaconazole, Tebuconazole, Imibenconazole, Prochloraz, 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 herbicides such as Glyphosate, Sulfosate, Glyfosinate, Bialaphos, Butamifos, Esprocarb, Prosulcarb, Benthiocarb, Pyributycarb, Asulam, Linulon, Dymron, Bensulfuron methyl, Cyclosulfamuron, Cinosulfuron, Pyrazosulfuron ethyl, Azimsulfuron, Imazosulfuron, Tenylchlor, Alachlor, Pretilachlor, Clomeprop, Etobenzanid, Mefenacet, Pendimethalin, Bifenox, Acifluorfen, Lactfen, Cyhalofop-butyl, loxynil, Bromobutide, Alloxydim, Setoxydim, Napropamide, Indanofan, Pyrazolate, Benzofenap, Pyraflufen-ethyl, Imazapyl, Sulfentrazone, Cafenstrole, Bentoxazon, Oxadiazon, Paraquat, Diquat, Pyriminobac, Simazine, Atrazine, Dimethametryn, Triazyflam, Benflesate, Flutiacet-methyl, Quizalofop-ethyl, Bentazon, calcium peroxide, etc.
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), granulosis virus cytoplasmic polyhedrosis virus (CPV), entomopox virus (EPV), etc.; microbial pesticides 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, etc.; and biotic pesticides utilized as herbicides, such as Xanthomonas campestris, etc.
In addition, the agricultural and horticultural chemical of the present invention can be used in combination with biotic pesticides including natural 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 (Amblyseius cucumeris), Predatory bug (Orius sauteri), etc.; microbial pesticides such as Beauveria brongniartii, etc.; and pheromones such as tetradecenyl=acetate (E,Z)-4,10-tetradecadienyl= acetate-(Z)-8-dodecenyl=acetate-(Z)-ll-tetradecenyl= acetate (Z)-13-icosen-l0-one, (Z)-8-dodecenyl= acetate-(Z)-ll-tetradecenyl=acetate-(Z)-13-icosen-10one-14-methyl-l-octadecene, etc.
Typical examples of the present invention are described below but they should not be construed as limiting the scope of the invention.
84
EXAMPLES
Production Example 1 Production of 3-iodo-N-(4-heptafluoroisopropyl- 2-methylphenyl)phthalamic acid A solution of 3.5 g of 4-heptafluoroisopropyl-2-methylaniline in 3 ml of acetonitrile was slowly dropped into a suspension of 3.5 g of 1iodophthalic anhydride in 30 ml of acetonitrile under ice-cooling. After completion of the dropwise 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 acetonitrile to obtain 4.0 g of the desired compound.
Physical property: m.p. 174 181 0 C. Yield: 57%.
Production of 3-iodo-N-(4-heptafluoroisopropyl- 2-methylphenyl)phthalisoimide To a suspension of 2.0 g of 3-iodo-N-(4heptafluoroisopropyl-2-methylphenyl)phthalamic acid in 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 product as the desired product. The desired product obtained was used in the subsequent reaction without purification.
1 H-NMR [CDC1 3 /TMS, 6 values (ppm)] 2.4(s, 3H), 7.3(d, 1H), 7.4(m, 2H), 1H), 8.1 1H), 8.2(d, 1H) Production of 3-iodo-N1-(4-heptafluoroisopropyl- 2-methylphenyl) -N 2 l-methyl-2- N-dimethyl sulfamoylamino)ethyl]phthalamide (compound No. In 30 ml of acetonitrile was dissolved 0.4 g of 3-iodo-N-(4-heptafluoroisopropyl-2-methylphenyl)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 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 chromatography to obtain 0.2 g of the desired compound.
Physical property: m.p. 95 0 C. Yield: Production Example 2 Production of 3-iodo-N1-(4-heptafluoroisopropyl-2-methylphenyl) -N 2 [l-methyl-2-(ethylaminocarbonyloxy)ethyl]phthalamide (compound No. 96) In 30 ml of acetonitrile was dissolved 0.55 g of 6-iodo-N-[l-methyl-2-(ethylaminocarbonyloxy)ethyl]- 86 phthalisoimide, followed by adding thereto 0.38 g of 4heptafluoroisopropyl-2-methylaniline, and the resulting mixture was stirred at room temperature for 3 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 magnesium sulfate and then distilled under reduced pressure to remove the solvent, and the resulting residue was purified by silica gel column chromatography to obtain 0.36 g of the desired compound.
Physical property: m.p. 185 0 C. Yield: 38%.
Production Example 3 Production of 3-iodo-N-(4-heptafluoroisopropyl- 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 4heptafluoroisopropyl-2-methylaniline, and the resulting mixture was heated under reflux for 3 hours.
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.
Yield: 89%.
87 Production of 3-iodo-N1-(4-heptafluoroisopropyl- 2-methylphenyl) -N 2 [3-t-butoxycarbonyl aminopropyl)phthalamide (compound No.
In 20 ml of dioxane was dissolved 0.5 g of 3iodo-N-(4-heptafluoroisopropyl-2-methylphenyl)phthalimide, followed by adding thereto 0.25 g of tbutyl N-(3-aminopropyl)carbamate and two drops of trifluoroacetic acid, and the resulting mixture was 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 magnesium sulfate and then distilled under reduced pressure to remove the solvent, and the resulting residue was purified by silica gel column chromatography to obtain 0.2 g of the desired compound.
Physical property: m.p. 145 0 C. Yield: 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 weight.
0 88 Formulation Example 1 Each compound listed in Table 1 50 parts or Table 2 Xylene 40 parts Mixture of polyoxyethylene 10 parts nonylphenyl ether and calcium alkylbenzenesulfonate An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolution.
Formulation Example 2 Each compound listed in Table 1 3 parts or Table 2 Clay powder 82 parts 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 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 mixture together with a suitable amount of water, followed by granulation and drying.
Formulation Example 4 Each compound listed in Table 1 20 parts or Table 2 Mixture of kaolin and synthetic, 75 parts high-dispersion silicic acid Mixture of polyoxyethylene 5 parts nonylphenyl ether and calcium alkylbenzenesulfonate A wettable powder was prepared by mixing uniformly and grinding the above ingredients.
Test Example 1 Insecticidal effect on diamondback moth (Plutella xylostella) Adult diamondback moths were released and 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, as an active ingredient to adjust the concentration to 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 mortality was calculated according to the following equation, whereby the insecticidal effect was judged according to the criterion shown below. The test was carried out with three replications of 10 insects.
Corrected mortality Number of Number of hatched insects hatched insects in untreated in treated group group Number of hatched insects in untreated group x 100 Criterion for judgment A mortality 100% B mortality 99% to C mortality 89% to D mortality 79% to 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 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, 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 litura) 0 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 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 thermostated at 250C. 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 i. The test was carried out with three replications of 10 insects.
Number of Number of alive insects alive insects in untreated in treated group group Corrected mortality x 100 Number of alive insects in untreated group As a result of the above test, it was found that the following compounds had an activity rated B or higher: compound Nos. i, 2, 6 to 9, 12 to 16, 19, 22, 28, 29, 33 to 36, 38 to 45, 48, 50, 51, 54 to 57, 59, 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, 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.) 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 ppm. After air-drying, the tea leaves were placed 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 thermostated at 25 0 C and having a humidity of 70%. Eight days after the inoculation, the dead and alive were counted 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 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, 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, 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 1 Z 1 2L~ N-R 2 Xn-+- Q~Y 3(I) Q4 N 2 13Q Z R (wherein A' is a (C2-C 8 alkylene group; a substituted 8 )alkylene group having one or more sub s..ti tuents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo (01-06) alkyl groups, alkoxy groups, halo (C 1 06) alkoxy groups, (01-06) alkylthio groups, halo (Cl- 06) alkylthio groups, (01-06) alkylsulfinyl groups, halo (01-06,) alkylsulfinyl groups, (C,-C 6 alkylsulfonyl groups, halo (01-06,) alkylsulfonyl groups, (Cl-C 6 )alkyl- 4: thio (01-06),alkyl groups, alkoxycarbonyl groups and 4:phenyl group; a (0 3 alkenylene group; a substituted *4 (03-08) alkenylene group having one or more stbstituents which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo(Cl- 0) alkyl groups, (01-06,) alkoxy -groups, halo (Cl-C 6 alkoxy groups, (01-06) alkylthio groups, halo (01-06) alkylthio groups, (01-06) alkylsul finyl groups; halo (01-C6) alkyl- .su ifinyl groups, alkylsulfonyl groups, halo (Cl- 06) alkylsulfonyl groups, (01-06) alkylthio (Cj-CE) alkyl 94 groups, (Cl-C 6 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 same or different and are selected from halogen atoms, cyano group, nitro group, halo alkyl groups, (Cl-C 6 )alkoxy groups, halo alkoxy groups, (Cl-C 6 alkylthio groups, halo alkylthio groups, alkylsulfinyl groups, halo alkylsulfinyl groups, (C 1 -C 6 alkylsuJlfonyl groups, halo (Cl-C 6 )alkyl- sulfonyl. groups, (Cl-C 6 alkylthio (C 1 -C 6 )alkyl groups, (C 1 -C 6 alkoxycarbonyl groups and phenyl group, any of the saturated carbon atoms in the above-mentioned (C 2 -CB)alkylene group, substituted (C 1 alkylene group, (C 3 -C alkenylene group, substituted (C 3 -C alkenylene group, (C 3 -C alkynylene group or substituted (C 3 -C 8 )alkynylene group being able to have a (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 2 -C)alkylene group, substituted (Cl-C 8 alkylene group, (C 3 -CB )alkeiiy- 99 9 lene group and substituted (C 3 -C alkenylefle group being able to form a (C 3 cycloalkane ring or a (0 3 -C 6 cyclo- alkene ring together with an alkylene group or an alkenylene group, B is or (wherein R' 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 group; a (C 3 C 6 )alkynyl group; a (C 3 -C 6 )cycloalkyl group; a (Cl- C 6 alkylcarbonyl group; a halo (Cl-C 6 alkylcarbony. group; a (C 1 -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, alkyl groups, halo (Cl-C 6 alkyl groups, C 6 alkoxy groups, halo (CI-C 6 alkoxy groups, (C,-C 6 alkyl- thio groups, halo (C 1 -C 6 alkylthio groups, (C 1 -C 6 alkyl- sulfinyl groups, halo (C 1 -C 6 aJlkylsulfinyl groups, (Cl- C 6 )alkylsulfonyl groups, halo (Cl-C 6 )alkylsulfonyl groups, monio(Cl-C 6 al1kyl amino groups, and di (Cl-C)alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different; a phenyl(Cl-C,)alkoxycarbonyl group; a substituted phenyl.(Cl-C 4 )alkoxycarbonyl group having on the ring one or more substituerits 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, (Cl-C 6 alkoxy groups, halo (C 1 -C 6 alkoxy groups, (C,-C 6 alkylthio groups, halo (Cl-C 6 alkylthio groups, 6 alkylsulfinyl groups, halo (Cl-C 6 alkylsulfinyl .:groups, (Cl-C 6 alkylsulfQnyl groups, halo (C 1 -C 6 alkyl- sulfonyl qroups, mono (Cl-C 6 al1kyl amino groups, and di(Cl- C 6 alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different; a phenyl(Cl-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 6 alkyl groups, halo (C 1 -C 6 alkyl 96 groups, (01-C6) alkoxy groups, halo (Cl-C 6 alkoxy groups, (C-C)alkylthio groups, halo (C-C 6 )alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (Cl-C 6 alkylsulfinyl groups, (C-C 6 )alkylsulfonyl groups, halo (Cl-C 6 alkyl- sulfonyl groups, mono (Cj 1 -C 6 al kyl amino groups, di (Cl- CO)alkylamino groups whose (CI-C 6 alkyl groups may be the same or different, and (C-C 6 )alkoxycarbonyl groups), Ris a hydrogen atom; a (Cl-C 6 )alkyl group; a halo (Cl-C6) alkyl group; a (Cl-0 4 )alkoxy(C,-C,) alkyl group; a (C 1 -C 4 )alkylthio(Cl-C 4 )alkyl group; a (02- C 6 alkenyl group; a halo (C- 2 -C 6 alkenyl group; a (03- C,)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 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, alkyl groups, halo (C 1 -C 6 alkyl groups, (Cl- 06) alkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C5) alkyl- d thio groups, halo (Cl-C 6 alkylthio- groups, (Cl-Cd)alkyl- sulfinyl groups, halo (Cl-C 6 )alkylsulfinyl groups, (Cl- 0 0C6) alkylsulfonyl groups, halo alkylsulfonyl groups, mono (01-06) alkylamino groups, di (Cl-C 6 )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 Vs. O 000000group; a substituted phenyl(Cl-C 4 )alkyl group having on see* 0 0 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 alkyl. 97 groups, (C 1 -C 6 alkoxy groups, halo (C-C 6 alkoxy groups, (Cl-C 6 alkyithio groups, halo(C,-C) alkylthio groups, (C-C 6 alkylsulfinyl groups, halo (C-C 6 alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo (C-C 6 alkyl- sulfonyl groups, mono(C-C 6 ,)alkylamino groups, di(C,- C 6 )alkylamino groups whose (C,-C,)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, (Cl-C 6 )alkyl.-groups, halo(Cl-C 6 )alkyl groups, (Cl-C 6 )alkoxy groups, halo (Cl-C)alkoxy groups, (C 1 -C)alkylthio groups, halo(Cl-C 6 alkylthio groups, (C 1 -C 6 alkylsulfinyl groups, halo(C-C 6 alkylsulfinyl groups, (Cl-C) alkylsulfonyl groups, halo(C-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 (C,-C)alkoxycarbonyl groups; -N(R 5 (R (wherein W 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(C 1 -C 6 )alkyl group; a (Cl-C 4 )alkoxy(Cl- C 4 )alkyl group; a (Cl-C 4 )alkylthio(Cl-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(C-C 6 alkoxy groups, (C-C 6 alkyl- 98 thio groups, halo(Cl-C 6 alkylthio groups, (C 1 -C 6 alkyl- sulfinyl groups, halo(C-C,) alkylsulfinyl groups, (C 1 C 6 alkylsulfonyl groups, halo (Cl-C,)alkylsulfonyl groups, mono alkylamino groups, di(C,-C,)alkylamino groups whose (CI-C)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, (C-C,)alkyl groups, halo(C,-C) alkyl groups, (Cl-C,)alkoxy groups, halo(C 1 -C 6 )alkoxy groups, (C 1 -C 6 alkylthio groups, halo (Cl-C 6 )alkylthio groups, (C,-C 6 )alkylsulfinyl groups, halo(C 1 -C 6 )alkylsulfinyl groups, (C-C 6 alkylsulfonyl groups, halo (C 1 -C 6 alkyl- sulfonyl groups, mono(C-C 6 alkylamino groups, di(Cl- C )alkylamino groups whose (C,-C 6 )alkyl groups may be the same or different, and 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 6 alkyl groups, halo (C-C 6 alkyl groups, (C 1 alkoxy groups, halo (Cl-C 6 alkoxy groups, (C 1 -C 6 alkylthio groups, halo (Cl-C 6 alkylthio groups, alkylsulfinyl groups, halo(Cl-C,) alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo(Cl-C 6 )alkyl- sulfonyl 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, 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 constituting the ring); (wherein W 1 and R 5 are as defined above); -C -W 1 -R (wherein W's, which may be the same or different, are as defined above, and R 7 is a (Cl-C) alkyl group; a halo (Cl-C 6 alkyl group; a (Cl-C 4 )alkoxy(Ci-C 4 )alkyl group; a (Cl-C 4 )alkyl- thio(Ci-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,)alkyl groups, halo(CI-C 6 )alkyl groups, (C-C 6 )alkoxy groups, halo(C 1 C )alkoxy groups, (C-C)alkylthio groups, halo(C 1 C 6 )alkylthio groups, (C-C 6 )alkylsulfinyl groups, halo (C-C 6 )alkylsulfinyl groups, (Cl-C 6 )alkylsulfonyl 100 groups, halo (01-06) alkylsulfonyl groups, mono (Cl- C,)alkylamino groups, di(Cl-C 6 )alkylamino groups whose (CI-C 6 )alkyi. groups may be the same or different, and (Cl-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, (C 1 -C 6 )alkyl groups, halo (Cl-C 6 alkyl groups, (Cl-C 6 alkoxy groups, halo (Cl-C 6 alkoxy groups, (C 1 -C 6 )alk-ylthio groups, halo (C 1 -C 6 alkylthio groups, 6 )alkylsulfiny1 groups, halo (C 1 -C 6 )alkylsulfinyl groups, alkylsulfonyl groups, halo (Cl-C 6 alkyl- sulfonyl groups, mono (Cl-C 6 alkyl amino groups, di (Cl- C 6 )alkylamino groups whose (C,-C)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 fro m halogen atoms, cyano group, nitro group, (C 1 -C,)alkyl groups, halo (Cl-C 6 alkyl groups, (Cl-C 6 alkoxy groups, halo (Cl-C 6 alkoxy groups, (01-06) alkylthio groups, halo (Cl-C 6 alkylthio groups, (0.-C 6 alkylsulfinyl groups, halo (C 1 -C 6 )alkylsulfinyl groups, (Cl-C 6 )alkylsulfonyl groups, halo (Cl-C 6 alkyl- sulfonyl groups, mono alkyl amino groups, di (Cl- C 6 )alkylamino groups whose (C 1 -C,)alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups); -S0 2 (wherein R' is as defined above) -SO,-N (R 6 (wherein R' and R 6 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 5 being able to bind to R 4 to form a 5- to 8-membered ring that may contain three or four a-toms 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 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 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 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 1 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 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 7 (wherein W W 2 and R 7 are as defined above, R 7 being able to bind to R 4 to form a 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 1 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 8 (wherein A 2 is -C(=NR 9 (wherein R 9 is a hydrogen atom, a (Cl-C 6 )alkyl group, a alkoxy group, a mono(Cl-C 6 alkylamino group, a di(Ci-C 6 )alkylamino group whose (C-C,)alkyl groups may be the same or different, a (C-C 6 )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, (C,-C,)alkyl groups, halo(C,-C) alkyl groups, (C-C)alkoxy groups, halo(C-C) alkoxy groups, 103 (Cl-C) alkylthio groups, halo(Cl-CE) alkylthio groups, (Cl-C) alkylsulfinyl groups, halo alkylsulfinyl groups, (C-C)alkylsulfonyl groups, halo(Cl-C 6 alkyl- sulfonyl groups, mono(Cl-C,)alkylamino groups, di(Cl- C )alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups), a (C 1 -C,)alkylene group, a halo(C,-C,)alkylene group, a (C 3 -C 6 )alkenylene group, a halo(C 3 alkenylene group, a (C 3 -C 6 )alkynylene group or a halo(C 3 alkynylene group, in the case of A 2 being or -C(=NR 9 (wherein R 9 is as defined above), R' is a hydrogen atom; a (C,-C,)alkyl group; a halo(Cl-C.,)alkyl group; a (C 3 cycloalkyl group; a halo(C 3 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, alkyl groups, halo(Cl-CE) alkyl groups, (Cl-C,)alkoxy groups, halo(Cl-C,)alkoxy groups, alkylthio groups, halo (Cl-C) alkylthio groups, (Cl-C,)alkylsulfinyl groups, halo (Cl-C 6 alkylsulfinyl groups, (Cl-C) alkylsulfonyl groups, halo(Cl-C)alkyl- sulfonyl groups, mono(C 1 -C 6 alkylamino groups, di(Cl- C 6 )alkylamino groups whose (C-C)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 selected from halogen atoms, cyano group, nitro group, (Cl-C 6 alkyl groups, halo (Cl-C 6 alkyl 104 groups, (C,-C,)alkoxy groups, halo(Cl-C 6 )alkoxy groups, (Cl-C6) alkylthio groups, halo(C 1 -C 6 alkylthio groups, alkylsulfinyl groups, halo(C-C 6 alkylsulfinyl groups, (C-C 6 alkylsulfonyl groups, halo (C 1 -C 6 alkyl- sulfonyl groups, mono(C-C) alkylamino groups, di(C,- C,)alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; or -A'-Ro 10 (wherein A3 is or (wherein R" is a hydrogen atom; a (C 1 -C 6 alkylcarbonyl group; a halo(Cl- C 6 )alkylcarbonyl group; a (C-C)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, (C,-C6)alkyl groups, halo(Cl- C0)alkyl groups, (C-C 6 ,)alkoxy groups, halo(Cl-C 6 alkoxy groups, (Cl-C6) alkylthio groups, halo(Cl-C 6 alkylthio groups, (C,-C,)alkylsulfinyl groups, halo (CI-C 6 alkyl- sulfinyl groups, (C-C 6 alkylsulfonyl groups, halo(Cl- alkylsulfonyl- groups, mono (C--C 6 alkylamino groups, di(C-C,)alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (C-C)alkoxycarbonyl groups; a.phenyl(Cl-C 4 )alkoxycarbonyl group; or 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 group, nitro group, (Cl-C) alkyl groups, halo (Cl-C 6 alkyl groups, (Cl-C 6 )alkoxy groups, halo(C-C 6 alkoxy groups, alkylthio groups, halo(Cl-C 6 alkylthio groups, 105 (C 1 -C 6 alkylsulfinyl groups, halo, fC 1 -C 3.i),a.lkylsulfinyl groups, (Cl-C 6 )alkylsulfonyl groups, halo(C-C)alkyl- sulfonyl groups, mono(C 1 -C 6 alkylamino groups, di(Cl- C 5 )alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (C-C 6 )alkoxycarbonyl groups), and R 10 is 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 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 (C -C 6 alkylcarbonyl group;.a halo (Cl-C 6 alkylcarbonyl group; a (C 1 -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-C 6 alkyl groups, halo (C-C 6 alkyl groups,. (C 1 C 6 alkoxy groups, halo alkoxy groups, (C 1 -C 6 alkyl- thio groups, halo(Cl-C 6 alkylthio groups, alkyl- sulfinyl groups, halo(C 1 -C 6 alkylsulfinyl groups, (C 1 C 6 alkylsulfonyl groups, halo (C,-C)alkylsulfonyl 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 6 )alkoxycarbonyl groups; a phenyl(Cl-C 4 )alkyl group; a substituted phenyl(Cl-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, (C 1 -C 6 )alkyl groups, halo(Cl-C,)alkyl groups, (Cl- C 6 alkoxy groups, halo(C 1 alkoxy groups, (C 1 alkyl- thio groups, halo(C-C) alkylthio groups, (Cl-C)alkyl- 106 sulfinyl groups, halo (C 1 -C 6 alkylsulfinyl groups, (Cl- alkylsulfonyl. groups, halo(C,-C) alkylsulfonyl groups, mono (C 1 -C 6 alkylamino groups, di(C 1 -C 6 alkylamino groups whose (C,-C.)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, (Cl-C 6 )alkyl groups, halo(C,-C 6 )alkyl groups, (Cl- C 6 )alkoxy groups, halo(C,-C)alkoxy groups, (Cl-C 6 )alkyl- thio groups, halo(C-C 6 alkylthio groups, (Cl-C)alkyl- sulfinyl groups, halo alkylsulfinyl groups, (C 1 C 6 alkylsulfonyl groups, halo(Cl-C 6 alkylsulfonyl groups, mono (C-C 6 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), in the case of A 2 being a (C 1 -C,)alkylene group, a halo(Cl-C,)alkylene group, a (C 3 -C 6 )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, R' is a hydrogen atom; a halogen atom; a cyano group; a nitro group; a (C 3 cycloalkyl group; a halo(C 3 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 1 C 6 )alkyl groups, halo(Cl-C 6 ).alkyl groups, (C-C 6 alkoxy groups, halo (C-C 6 alkoxy .groups, (Cl-C 6 alkylthio 107 groups, halo (Cl-C) alkyithio groups, (C 1 -C 6 alkylsulfinyl groups, halo(Cl-C) alkylsulfinyl groups, (Cl-C,)alkyl- sulfonyl groups, halo(Cl-C 6 alkylsulfonyl groups, mono (Cl-C 6 alkylamino groups, di(C 1 -C,)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 1 alkyl groups, halo (C-C 6 alkyl groups, (Cl- C 6 alkoxy groups, halo(C-C) alkoxy groups, (Cl-C 6 )alkyl- thio groups, halo(Cl-C)alkylthio groups, (Cl-C 6 )alkyl- sulfinyl groups, halo(Cl-C)alkylsulfinyl groups, (C 1 C,)alkylsulfonyl groups, halo (Cl-C)alkylsulfonyl groups, mono (C,-C 6 alkylamino groups, di.(Cl-C 6 )alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; or 2 (wherein A' is (wherein R" is as defined above), or -C(=N-OR" 3 (wherein R' 3 is a hydrogen atom, a (C 1 -C 6 )alkyl group, a halo(C-C 6 alkyl group, a (C 3 -C 6 )alkenyl group, a halo(C 3 -C,)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, (Cl-Cs)alkyl groups, halo(Cl- C )alkyl groups, (Cl-C 6 )alkoxy groups, halo(Cl-C 6 alkoxy 108 groups, (CI-C 6 alkyithia groups, halo (Cl-C 6 alkylthio groups, (C 1 -C 6 alkylsulfinyl groups, halo (C 1 alkyl- sulfinyl groups, (C 1 -C 6 )alkylsulfonyl groups, halo(Cl- CE) alkylsulfonyl groups, mono al kyl amino groups, d-i(Cl-C 6 )alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, and (C,-C)alkoxycarbonyl groups), in the case of A' being _S02_ or -N (wherein R 11 is as defined above), R 12 is a hydrogen atom; a (Cl-C)alkyl group; a halo (Cl-C 6 alkyl group; a (C 3 -C 6 )alkenyl group; a halo (C 3 -C6) alkenyl group; a (C 3 -C)alkynyl group; a halo (C 3 -C 6 alkynyl group; a (C 3 cycloalkyl group; a halo (C 3 cycloalkyl group; a (Cl-C 6 alkylcarbonyl group; a halo (Cl-C 6 alkyl- carbonyl group; a (Cl-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, 6 alkyl groupsi halo (C 1 -C 6 alkyl groups, (Cl- 06,) alkoxy groups, halo (.C 1 -C 6 alkoxy groups, (Cl-C 6 alkyl- thio groups, halo (Cl-C 6 alkylthio groups, (Cl-C 6 alkyl- sulfinyl groups, halo (CC 6 alkylsulfinyl groups, (Cl- C6) alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl groups, mono al kyl amino groups, di (C,-C 6 al kyl amino groups whose (Cl-C 6 )alkyl groups may be the same or different, and 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 109 or different and are selected from halogen atoms, cyano group, nitro group, (C 1 alkyl groups, halo(Cl-C 6 )alkyl groups, (C 1 -C 6 alkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C 6 alkylthio groups, halo (Cl-C 6 )alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (Cl-C 6 alkylsulfinyl groups, (Cl-C 6 alkylsulfonyj. groups, halo (q,-C 6 alkyl- suilfonyl groups, mono al kyl amino groups, di (Cl- C6)alkyl amino 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 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, (C,-C 6 alkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C 6 )alkylthio groups, halo (Cl-C 6 alkylthio groups, (Cl-C 6 )alkylsul finyl groups, halo (C,-C 6 alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo (Cl-C 6 alkyl- sulfonyl groups, mono -C)al kylamino groups, di(Cl- C 6 alkylamino groups whose- (C-C 6 )alkyl groups may be the same or different, and (CI-C 6 )alkoxycarbonyl groups, (ii) in the case of A' being -C or -C (=NOR 1 3 (wherein R" 3 is as defined above), R' 2 is a hydrogen atom; a alkyl. group; a halo (Cl-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 alkoxy group; a halo (C 1 -C 6 alkoxy group; a (Cl- C 6 )alkylthio group; a halo (Cl-C 6 )alkylthio group; a mono (Cl-C 6 alkylamino group; a di alkylamino group 110 whose (C 1 -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(C 1 -C 6 alkyl groups, (Cl- C 6 alkoxy groups, halo (Cl-C6)alkoxy groups, (Cl-C 6 )alkyl- thio groups, halo(Cl-C) alkylthio groups, (Cl-C 6 )alkyl- sulfinyl groups, halo (CI-C 6 alkylsulfinyl groups, (C 1 C 6 )alkylsulfonyl groups, halo(Cl-C,) alkylsulfonyl groups, mono (C-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; 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 fromhalogen atoms, cyano group, nitro group, (C-C 6 ,)alkyl groups, halo(Cl-C,)alkyl groups, (Cl- C,)alkoxy groups, halo(Cl-C,)alkoxy groups, (Cl-C 6 )alkyl- thio groups, halo(Cl-C 6 alkylthio groups, (C,-C 6 )alkyl- sulfinyl groups, halo(C 1 -C 6 alkylsulfinyl groups, (C- C6) alkylsulfonyl groups, halo(C 1 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 (C-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, (C 1 -C 6 )alkyl groups, halo(Cl-C 6 alkyl groups, (Cl- C 6 alkoxy groups, halo (Cl-C) alkoxy groups, (C 1 -C 6 alkyl- 111 thio groups, halo(C-C 6 alkylthio groups,, alkyl- sulfinyl groups, halo(C 1 -C 6 alkylsulfinyl groups, C) alkylsulfonyl groups, halo (Cl-C)alkylsulfonyl groups, mono (C 1 -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 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, (Cl-C 6 )alkyl groups, halo(C 1 -C 6 )alkyl groups, (Cl- C 6 )alkoxy groups, halo(Cl-C,)alkoxy groups, (Cl-C 6 )alkyl- thio groups, halo(C-C 6 alkylthio groups, (Cl-Cs)alkyl- sulfinyl groups, halo (C-C 6 alkylsulfinyl groups, (C 1 C 6 )alkylsulfonyl groups, halo(Cl-C 6 )alkylsulfonyl groups, mono (Cl-c 6 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; 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 6 ,)alkyl groups, halo(Cl-C,)alkyl groups, (C- C 6 )alkoxy groups, halo(C,-C)alkoxy groups, (C-C 6 ,)alkyl- thio groups, halo(Cl-C 6 alkylthio groups, (Ci-C) alkyl- sulfinyl groups, halo(Cl-C)alkylsulfinyl groups, (C- C 6 alkylsulfonyl groups, halo(Cl-C 6 alkylsulfonyl groups, mono (C 1 -C 6 ).alkylamino groups, di(Cl-C)alkylamino groups whose (C-C 6 ,)alkyl groups may be the same or different, and (Cl-C 6 alkoxycarbonyl groups)), 112 further, R 2 being able to bind to A' 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 Q' 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 (C3-C 6 )cycloalkyl group; a halo(C3-C 6 cycloalkyl 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 (Ci-C 6 )alkyl groups, (C 1 C6)alkoxy groups, halo(C-C) alkoxy groups, alkyl- thio groups, halo(Ci-C) alkylthio groups, (C 1 -C 6 )alkyl- sulfinyl groups, halo(C,-C 6 )alkylsulfinyl groups, (Cl- C6)alkylsulfonyl groups, halo(C-C6)alkylsulfonyl groups, mono (C,-C 6 alkylamino groups, di(C,-C 6 )alkylamino groups whose (C-C 6 )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, (Ci-C6)alkyl groups, halo (Ci-C6) alkyl groups, (Cl- C) alkoxy groups, halo (C-C6) alkoxy groups, alkyl- thio groups, halo(Ci-C 6 )alkylthio groups, (C-C 6 ,)alkyl- 113 sulfinyl groups, halo (Cj-C 6 alkylsul..finyl groups, (C 1 C 6 alkylsulfonyl groups, halo(C,-C 6 ,)alTylsulfonyl groups, mono(Cl-C)alkylamino groups, di(C-C,)alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (Cl-C 6 alkoxycarbonyl groups; or -A 5 -R" 4 (wherein A is -C(=NOR' 3 (wherein R' 3 is as defined above), a (C-C)alkylene group, a halo(Cl-C,.)alkylene group, a (C,-C 6 )alkenylene group, a halo(C 2 -C 6 )alkenylene group, a (C,-C 6 )alkynylene group or a halo(C 3 -C 6 )alkynylene group, in the case of A 5 being -SO- or R 1 is a halo(C3-C) cycloalkyl group; a halo(C 3 C )cycloalkenyl group; a phenyl group; a substituted phenyl group having one or more substituents which may be the samfe or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C,)alkyl groups, halo (C 1 -C 6 alkyl groups, (Cl-C 6 )alkoxy groups, halo(Cl- Cs)alkoxy groups, (C1-C6)alkylthio groups, halo(Cl- C,)alkylthio groups, (C 1 -C 6 )alkylsulfinyl groups, halo alkylsulfinyl groups, alkylsulfonyl groups, halo(C1-C6) alkylsulfonyl groups, mono(Cl- C )alkylamino groups, di(Cl-C)alkylamino groups whose (Cl-C,)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 selected from halogen atoms, cyano group, nitro group, (C-C6)alkyl groups, halo(C1-C6)alkyl groups, (C- 114 C 6 )alkoxy groups, halo (C 1 -C 6 alkoxy grocups, (Cl-C 6 alkyl- thio groups, halo (Cl-C 6 alkyithia groups., (Cl-06) alkyl- sulfinyl groups, halo (C 1 -C 6 )alkylsulfinyl groups, (Cl- 06 )alkylsulfonyl groups, halo (C 1 -C 6 alkylsulfonyl groups, mono (Cl-C 6 )alkylamino groups, di (C 1 -C 6 )alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, and (C1-C6) alkoxycarbonyl groups; or -A 6-R" 5 (wherein A 6 is a (Cl-C.)alkylene group, a halo 6 alkylene group, a (C 3 -C 6 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, and R 15 is a hydrogen atom; a halogen atom; a (03- C 6 s)cycloalkyl group; a halo (C,-C,)cycloalkyl group; a (01-06) 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, (Cl- 06) alkyl groups, halo (C1-06) alkyl groups, (Cl-C 6 alkoxy groups, halo alkoxy groups, (C-C 6 )alkylthio groups, halo (Cl-C) alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo(Cl-C 6 alkylsulfinyl groups, (Cl-C 6 )alkyl- sulfonyl groups, halo (01-06) alkylsulfonyl groups, mono (01-06) al kyl amino groups, di (01-06)alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarbonyl groups; or -A7-R 1 6 (wherein A7 is -SO- or -S02-, and R' 6 is a (01-C6 )alkyl group; a halo (01-06) 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,)alkynyl group; a (C 3 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, (Cl- C 6 )alkyl groups, halo(C-C 6 alkyl groups, (Cl-C 6 alkoxy groups, halo(Cl-C 6 )alkoxy groups, (Cl-C 6 )alkylthio groups, halo (C-C)alkylthio groups, (Cl-C)alkylsulfinyl groups, halo(Cl-C,)alkylsulfinyl groups, (C,-C 6 alkyl- sulfonyl groups, halo(Cl-C)alkylsulfonyl groups, mono (Cl-C 6 alkylamino groups, di(Cl-C 6 )alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (Cl-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, (C 1 -C 6 )alkyl groups, halo(C 1 -C 6 alkyl groups, (Cl- C )alkoxy groups, halo(C 1 -C 6 )alkoxy groups, (Cl-C 6 alkyl- thio groups, halo(Cl-C 6 alkylthio' groups, (Cl-C 6 alkyl- sulfinyl groups, halo(C,-C 6 alkylsulfinyl groups, (Cl- C alkylsulfonyl groups, halo(Cl-C 6 alkylsulfonyl 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 (Cl-C 6 alkoxycarbonyl. groups), in the case of A 5 being or -C(=NO R (wherein R" 3 is as defined above), R" is 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 C 6 )cycloalkyl group; a halo(C 3 -C 6 cycloalkyl group; a 116 (C 1 -C 6 )alkoxy group; a (C 1 -C 6 )alkylthio group; a mono(Cl- C 6 alkylamino group; a di(C 1 -C,)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 and are selected from halogen atoms, cyano group, nitro group, (Cl-Cs)alkyl groups, halo(C 1 -C 6 )alkyl groups, (C 1 C 6 alkoxy, groups, halo alkoxy groups, (Cl-C) alkyl- thio groups, halo.(Cl-C,)alkylthio groups, (Cl-C 6 )alkyl- sulfinyl groups, halo(C-C 6 alkylsulfinyl groups, (Cl- C 6 alkylsulfonyl groups, halo(C-C6) alkylsulfonyl groups, mono (C 1 -C 6 alkylamino groups, di(Cl-C 6 )alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (CI-C 6 ,)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,)alkyl groups, halo(C 1 -C,)alkyl groups, (Cl- C 6 )alkoxy groups, halo(C 1 -C 6 )alkoxy groups, (Cl-C,)alkyl- thio groups, halo(Cl-C 6 ,)alkylthio groups, (C 1 -C)alkyl- sulfinyl groups, halo(Cj-C 6 alkylsulfinyl groups, (Cl- C 6 alkylsulfonyl groups, halo(Cl-C 6 alkylsulfonyl groups, mono (Cl-C) alkylamino groups, di(C 1 -C 6 )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 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 -graflps, (Cl- alkoxy groups, halo (CI-C 6 alkoxy groups, (C 1 -C 6 alkyl- thio groups, halo alkylthio groups, (C 1 -C 6 alkyl- sulfiny. groups, halo (C 1 -C 6 alkylsulfinyl groups, (Cl- C 6 )alkylsulfonyl groups, halo (C 1 -C 6 alkylsulfonyl groups, mono (Cl -C 6 al kyl amino groups, di (C 1 -C 6 al kyl amino groups whose (Cl-C 6 alkyl groups may be -the same or different, and (Cl-C 6 alkoxycarbonyl groups, in the case. of As being a (C,-C 6 ,)alkylene group, a halo (Cl-C 6 alkylene group, a (C 2 alkenylene group, a halo (C 2 alkenylene group, a (C 2 -C,)alkynylene group or a halo (C3-C 6 alkynylene group, R" 4 is a hydrogen atom; a halogen atom; a (C 3 -C)cycloalkyl group; a halo (C 3 -C 6 cycloalkyl group; a (Cl-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, (C,-C,)alkyl groups, halo (Cl-C 6 alkyl groups, (Cl-C 6 alkoxy groups, halo(Cl-C 6 )alkoxy groups, (Cl-C 6 alkylthio groups, halo (Cl-C- 6 alkylthio groups, (Cl-C 6 )alkylsulfinyl groups, halo (Cl-C,)alkylsulfinyl groups, alkylsulfonyl. groups, halo (Cl-C 6 alkyl- sulfonyl 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 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, (Cl-C 6 alkyl groups, halo (Cl-C 6 alkyl groups, (Cl-C 6 alkoxy groups, halo alkoxy groups, alkyithic groups, halo (C 1 -C 6 alkylthio groups, (C 1 -C 6 alkylsulfinyl groups, halo (Cl-C6)alkylsulfinyl groups, (C 1 -C 6 )alkylsulfonyl groups, halo (Cl-C 6 )alkyl- sulfonyl groups, mono al kylamino groups, di(C,- Cd)alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, and (C,-C 6 )alkoxycarbonyl groups; or -A 8 -R' 7 (wherein A' is -So- or -SO 2 and R" is a (C 3 -C 6 )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, (Cl- C 6 )alkoxy~groups, halo (Cl-C 6 )alkoxy groups, (Cl-C 6 )alkyl- thic groups, halo alkyithia groups, (Cl-C 6 alkyl- sulfinyl groups, halo (Cl-C 6 )alkylsulfinyl groups, (Cl- C 6 alkylsulfonyl groups, halo alkylsulfonyl groups, mono al kyl amino groups, di (C,-C 6 alkylamino groups whose (Cl-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 6 alkyl groups, halo (Cl-C 6 alkyl groups, (C 1 06 )alkoxy groups, halo (C1-C6) alkoxy groups, alkyl- thio groups, halo (C 1 -C 6 alkylthio groups, (Cl-C 6 )alkyl- sulfinyl groups, halo alkylsulfinyl groups, (C 1 119 C 6 alkylsulfony]. groups, halo (C,-C 6 alkyl.sulfonyl groups, mono (Cl-C 6 al kyl amino. groups, di (C 1 al kyl amino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C 6 alkoxycarbonyl groups; or -AK-R 8 (wherein A' is a (C 1 -C 6 )alkylene group,-.a halo (Cl-C 6 alkylene group, a (C 2 -C,)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" 8 is a hydrogen atom; a halogen atom; 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 6 alkoxy grqup; a C 6 )alkylthio group; a halo (Cl-C 6 alkylthio group; a (C 1 C,)alkylsulfinyl group; a halo (Cl-C 6 alkylsulfinyl group; a (Cl-C 6 )alkylsulfonyl group; a halo 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, alkyl groups, halo (Cl-C 6 alkyl groups, (Cl-C 6 )alkoxy groups, halo (Cl-C,)alkoxy groups, alkylthio -groups, halo (Cl-C 6 alkylthio groups, (C 1 -C 6 alkylsulfinyl groups, halo alkylsulfinyl groups, alkylsulfonyl groups, halo (Cl-C 6 alkyl- sulfonyl groups, mono (C,-C 6 al kyl amino groups, di(Cl- C,)alkylamino groups whose (C,-C)alkyl grou Ps 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 different and are selected from halogen atoms, cyano group, nitro group, (C 1 -C 6 )alkyl groups, halo (Cl-C 6 alkyl 120 groups, (Cl-C 6 alkoxy groups, halo (C,-C 6 alkoxy groups, (C 1 -C 6 alkylthio groups, halo (Cl-C6) alkylthio groups, alkylsulfinyl groups, halo (C 1 -C 6 alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo alkyl- sulfonyl groups, mono (C 1 -C 6 alkylamino groups, di (Cl- C 6 )alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, an d (Cl-C 6 )al-koxycarbonyl 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 1 -C 6 )alkyl groups, halo (C 1 -C 6 alkyl groups, (Cl-C 6 )alkoxy groups, halo (Cl-C 6 )alkoxy groups, (Cl-C 6 alkylthio groups, halo (C 1 -C 6 alkyithio groups, (Cl-C6) alkylsulfinyl groups, halo (Cl-C6)alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo (C 1 alkyl- sulfonyl groups, mono (Cl-C6) alkylamino groups, di (Cl- alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C6)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, (Cl-C 6 alkyl groups, halo alkyl groups, (C 1 0 5 )alkoxy groups, halo (Cl-C 6 alkoxy groups, (C 1 -C 6 )alkyl- thio groups, halo alkylthio groups, (C 1 -C 6 )alkyl- sulfinyl groups, halo (01-06) al'kylsulfinyl groups, (C 1 06) alkylsui1fonyl, groups, halo (Cl-C 6 alkylsulfonyl groups, mono (C 1 -C 6 al kyl amino groups, di (C 1 -C 6 alkylamino groups whose (Cl-C 6 alkyl groups may be the same or' different, 121 and (C-C)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, (C-C 6 alkyl groups, halo(Cl-C 6 ,)alkyl groups, (Cl-C 6 )alkoxy groups, halo(Cl- C )alkoxy groups, (C-C 6 )alkylthio groups, halo(Cl- alkylthio groups, (C,-C 6 )alkylsulfinyl groups, halo(Cl-C 6 .)alkylsulfinyl groups, (C-C 6 ,)alkylsulfonyl groups, halo(C-C 6 alkylsulfonyl groups, mono(Cl- C6) alkylamino groups, di(Cl-C)alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and 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(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, alkyl groups, halo(C-C) alkyl groups, (C-C6)alkoxy groups, halo(Cl-C,)alkoxy groups, (Cl-C) alkylthio groups, halo(C-C,)alkyithio groups, (C 1 -C 6 alkylsulfinyl groups, halo(Cl-C 6 alkylsulfinyl groups, (Cl-C,)alkylsulfonyl groups, halo(Cl-C 6 )alkyl- sulfonyl groups, mono(C-C) alkylamino groups, di(Cl- C )alkylamino groups whose. (Cl-C)alkyl groups may be the 122 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(Cl-C 6 )alkyl groups, (Cl-C 6 )alkoxy groups, halo(C 1 -C 6 )alkoxy groups, (CI-C 6 alkylthio groups, halo(C,-C 6 alkylthio groups, (C-C 6 )alkylsulfinyl groups, halo(CI-C 6 alkylsulfinyl groups, (Ci-C,)alkylsulfonyl groups, halo(C-C 6 alkyl- sulfonyl groups, mono(Ci-C.) 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; or -A-R 1 4 (wherein A 5 and R 1 4 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-C 6 )alkyl groups; halo(C 1 -C 6 )alkyl groups; (C 1 C) alkoxy groups; halo(Ci-C 6 )"alkoxy groups; (Ci-C,)alkyl- thio groups; halo(Ci-C 6 alkylthio groups; (Ci-C,)alkyl- sulfinyl groups; halo(Ci-C 6 )alkylsulfinyl groups; (Ci- C,)alkylsulfonyl groups; halo(Cl-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, (Cl-Cg)alkyl groups, halo(Ci-C 6 )alkyl groups, (C 1 alkoxy-groups, halo(C-C) alkoxy groups, (Ci-C alkyl- thio groups, halo(C 1 alkylthio groups, (Ci-C) alkyl- 123 sulfinyl groups, halo(Cl-C 6 alkylsulfinyl groups, (Cl- C 6 alkylsulfonyl groups, halo(C-C 6 alkylsulfonyl groups, mono alkylamino groups, di(Cl-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, (C 1 -C 6 )alkyl groups, halo(C 1 -C,)alkyl groups, (Cl- C,)alkoxy groups, halo(C,-C.)alkoxy groups, (C-C 6 )alkyl- thio groups, halo(C,-C)alkylthio groups, (C,-C 6 )alkyl- sulfinyl groups, halo(C-C 6 alkylsulfinyl groups, (Cl- C )alkylsulfonyl groups, halo(Cl-C 6 alkylsulfonyl groups, mono alkylamino groups, di (Cl-C) alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups, m is an integer of 1 to 5, and each of Z 1 and Z' is an oxygen atom or a sulfur atom} or a salt thereof, provided that when Q' to Q 5 represent carbon atoms, B represents and R' represents a hydrogen atom, (Cl-C 3 )alkyl group, phenyl group or substituted phenyl group, then Ym is not 4- trifluoromethyl group, 2-methyl-5-chloro group, 2- methyl-4-difluoromethoxy group, 2-methyl-4- pentafluoroethyl group and 2-methyl-4-trifluoromethoxy group, when Q 1 to Q 5 represent carbon atoms, A' 123A represents (C,-C 2 )alkylene group, 11 :represents -N(R 4 and R 4 represents a hydrogen atom, (C,-C 2 )alkoxycarbonyl group or benzyloxycarbonyl group, then Ym is not 2- methyl-4-pentafluoroethyl group, 2-methyl-4-hepta- fluoroisopropyl group and 2-methyl-4-trifluoromethoxy group, and when Q' to Q 5 represent carbon atoms, B represents and R 2 binds to R1 to form a 6-membered ring, then Ym is not 2-trifluoromethyl group, 2-methyl- group, 2-methyl-4-difluoromethoxy group, 3- group and 2-methyl-4- pentafluoroethyl group.
2. An aromatic diamide derivative or a salt thereof according to claim 1, wherein A' is a CB)alkylene group; a substituted (C 2 -CB)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(C,-C,)alkyl groups, (C- C,)alkoxy groups, halo(C 1 -C 6 )alkoxy groups, (C,-C,)alkyl- thio groups, halo(Cl-C.) alkylthio groups, (C,-C,)alkyl- sulfinyl groups, halo(C-C) alkylsulfinyl groups, (C- 124 C )alkylsulfonyl groups, halo(C-C 6 alkylsulfonyl groups, (C 1 alkylthio (C 1 -C 6 alkyl groups, (C-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 which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo (Cl-C 6 alkyl groups, alkoxy groups, halo C 6 alkoxy groups, (Cl-C.)alkylthio groups, halo(Cl- alkylthio groups, (C 1 -C 6 alkylsulfinyl groups, halo (Cl-C 6 alkylsulfinyl groups, (C 1 -C 6 alkylsulfonyl groups, halo(Cl-C,) alkylsulfonyl groups, (C-C 6 alkyl- thio (C-C 6 alkyl groups, (C,-C,)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, (Cl-C) alkoxy groups, halo(C.- C 6 )alkoxy groups, (Cl-C 6 )alkylthio groups, halo(C,- C )alkylthio groups, 4C,-C 6 ,)alkylsulfinyl groups, halo (C 1 -C 6 ,)alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo(C,-C 6 alkylsulfonyl groups, (C-C 6 alkyl- thio alkyl groups, (C 1 alkoxycarbonyl groups and phenyl group, any of the saturated carbon atoms in the above-mentioned (C 2 -C8)alkylene group, substituted (C 1 C )alkylene group, (C 3 -C)alkenylene group, substituted (C 3 -C,)alkenylene group, (C 3 -C,)alkynylene group or substituted (C 3 -C 8 )alkynylene group being able to have a 125 (C 2 -C,)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 (C2-Cs)alkylene group, substituted (Cl-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 -C 6 )cycloalkene ring together with an alkylene group or an alkenylene group, B is or -N(R 4 (wherein R' is a hydrogen atom; a (Cl-C)alkyl group; a halo(C 1 -C 6 )alkyl group; a (C 3 -C 6 alkenyl group; a halo (C 3 -C 6 alkenyl group; a (C3- C,)alkynyl group; a (C 3 -C 6 cycloalkyl group; a (Cl- C 6 alkylcarbonyl group; a halo(C-C 6 alkylcarbonyl group; a (C 1 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 6 ,)alkyl groups, halo (Cl-C 6 alkyl groups, C 6 )alkoxy groups, halo(C,-C6) alkoxy groups, (C-C 6 ,)alkyl- thio groups, halo(Cl-C 6 alkylthio groups, (C 1 -C 6 alkyl- sulfinyl groups, halo(Cl-C 6 alkylsulfinyl groups, C 6 alkylsulfonyl groups, halo(C,-C.) alkylsulfonyl groups, mono (C-C 6 alkylamino groups, and di(Cl-C 6 )alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different; a phenyl(C-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 telected from halogen atoms, cyano 126 group, nitro group, (C,-C 6 alkyl groups, halo (Cl-C 6 alkyl groups, alkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C 5 alkylthio groups, halo alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (Cl-C 6 alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo (Cl-C 6 alkyl- sulfonyl groups, mono (C 1 -C 6 alkylamino groups, and di C 6 )alkylamino groups whose (C,-C,)alkyl groups may be the same or different; a phenyl (C 1 -C 4 alkyl group; or a substituted phenyl(Cl-C,)alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, cyano gr6up, nitro group, (CI-C 6 )alkyl groups, halo (Cl-C 6 alkyl groups, (C,-C 6 alkoxy groups, halo (C,-C,)alkoxy groups, (Cl-C 6 alkylthio groups, halo (Cl-C 6 alkylthio groups, (Cl-C.)alkylsulfinyl groups, halo (Cl-C 6 alkylsulf inyl groups, (Cl-C 6 alkylsulfonyl groups, halo (Cl-C 6 alkyl- sulfonyl groups, mono alkylamitio groups, di(C,- C 6 )alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (Cl-C 6 )alkoxycarboriyl groups), R1 is a hydrogen atom; a (Cl-C 6 )alkyl group; a halo (C 1 -C 6 alkyl group; a (Cl-C 4 alkoxy (Cl-C 4 alkyl group; a (C 1 -C 4 alkylthio (C 1 -C 4 alkyl group; a (C 2 C 6 alkenyl group; a-halo (C 2 -C 6 alkeny2. group; a (C 3 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 substituted phe nyl group having one or more substituents which may be the same or different and are selected from halogen atoms, cyano group, pitro 127 group, (C 1 -C 6 alkyl groups, halo alkyl groups, (Cl- alkoxy groups, halo alkoxy groups, alkyl- thio groups, halo alkylthio groups, (Cl-C 6 alkyl- sulfinyl groups, halo (Cl-C 6 alkylsulfinyl groups, C 6 )alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl 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 (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 sampe or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 )alkyl groups, halo (Cl-C 6 alkyl groups, (Cl-C 6 alkoxy groups, halo alkoxy groups, (Cl-C 6 alkylthio groups, halo (C,-C 6 alkylthio groups, (Cl-C,)alkylsulfinyl groups, halo (Cl-C 6 alkylsulfinyl groups, alkylsulfonyl groups, halo (Cl-C 6 alkyl- sulfonyl groups, mono (Cl-C) alkylainino groups, di(C 1 C 6 )alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (C 1 -C 6 alkoxycarbonyl* groups; a heterocyclic group; a substituted heterocyclic group having one or more substituents which may be the samte or different and are selected from halogen atoms, cyano group, nitro group, (Cl-C 6 )alkyl groups, halo alkyl groups, (C 1 -C 6 alkoxy groups, halo (C 1 -C 6 alkoxy groups, (Cl-C)alkylthio groups, halo alkylthio groups, (C-C 6 )alkylsulfinyl groups, halo (CI-C) akylsulf inyl groups, (Cl-C 6 alkylsulfonyl groups, halo (C 1 -C 6 alkyl- sulfonyl groups, mono (Cl-Cs) al1kyl amino groups, di 128 C) alkylamino groups whose (C-C 6 ,)al'kyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; -C -N (R (R 6 (wherein W 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 6 )alkyl group; a (C 1 -C 4 )alkoxy(C 1 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, (Cl-C 6 alkyl groups, halo(C-C 6 alkyl groups, (C- C 6 )alkoxy groups, halo(C-C 6 alkoxy groups, (C 1 -C 6 alkyl- thio groups, halo(C-C 6 alkylthio groups, (Cl-C 6 alkyl- sulfinyl groups, halo(Cl-C.) alkylsulfinyl groups, (C 1 C 6 alkylsulfonyl groups, halo(C 1 -C 6 alkylsulfonyl groups, mono (Cl-C) alkylamino groups, di(C-C 6 alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C) alkoxycarbonyl groups; a phenyl(Cl-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,)alkyl groups, halo(C-C 6 alkyl groups, (Cl-C 6 )alkoxy groups, halo(Cl-C 6 )alkoxy groups, (Cl-C 6 alkylthio groups, halo (C-C 6 alkylthio groups, (C-C 6 alkylsulfinyl groups, halo(Cl-C 6 alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo(C-C 6 alkyl- sulfonyl groups, mono(Cl-C,) alkylamino groups, di(C 1 C 6 )alkylamino groups whose (C,-C 6 )alkyl groups may be the 129 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 or different and are selected from halogen atoms, cyano group, nitro group, (Ci-C 6 )alkyl groups, halo(Cl-C 6 )alkyl groups, (Cl-C 6 )alkoxy groups, halo(C 1 -C 6 )alkoxy groups, (Ci-C) alkylthio groups, halo(C 1 -C 6 alkylthio groups, (Ci-C 6 alkylsulfinyl groups, halo(Ci-C 6 alkylsulfinyl groups, (Ci-C) alkylsulfonyl groups, halo(Cl-C 6 )alkyl- sulfonyl groups, mono (CI-C 6 alkylamino groups, di(C,- C 6 )alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (C-C 6 )alkoxycarbonyl groups, 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(=W1)-R (wherein W' and R 5 are as defined above); -C(=W 1 )-W-R 130 (wherein W's, 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,- C )alkyl group; a (C 1 -C 4 )alkoxy(C 1 -C 4 )alkyl group; a C 4 )alkylthio(Cl-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 alkyl groups, (Cl- C) alkoxy groups, halo(Cl-C.) alkoxy groups, (C 1 -C 6 alkyl- thio groups, halo(Cl-C 6 alkylthio groups, (Cl-C 6 alkyl- sulfinyl groups, halo(Cl-C.) alkylsulfinyl groups, C 6 )alkylsulfonyl groups, halo alkylsulfonyl groups, mono (Cl-C 6 alkylamino groups, di(C 1 -C 6 )alkylamino groups whose (Cl-C,)alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups; a phenyl(CI-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, *(Cl-C,)alkyl groups, halo(C 1 -C6)alkyl groups, (Cl-C,)alkoxy groups, halo (C-C,)alkoxy groups, (C,-C 6 alkylthio groups, halo'(C-C) alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (Cl-C) alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo(C-C 6 alkyl- sultonyl groups, mono(Cl-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; 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, .(C-C 6 )alkyl groups, halo(C 1 -C 6 )alkyl groups, (Cl-C 6 )alkoxy groups, halo (C-C 6 alkoxy groups, (C 1 -C,)alkylthio groups, halo(C,-C 6 )alkylthio groups, (C 1 alkylsulfinyl groups, halo (CI-C 6 alkylsulfinyl groups, (Ci-C 6 )alkylsulfonyl groups, halo (Ci-Cg) alkyl- sulfonyl groups, mono(C,-C 6 alkylamino groups, di(C 1 C 6 )alkylamino groups whose (C-C 6 )alkyl groups may be the same or different, and (Ci-C)alkoxycarbonyl groups); -SO 2 -R 7 (wherein R 7 is as defined above); -S0 2 -N(R S (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 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 132 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 5 being able to bind to R 6 to form a 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 1 being able to be -OR 5 (wherein R 5 is as defined above), -C(W 2 )-N(R 5 )R 6 (wherein W 2 is =CH-NO,, =N-NO 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 selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring) or -C(W2)-W-R' (wherein W 1 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, 133 each of R 2 and R 3 which may be the same or different, is a hydrogen atom or a (Ci-C 3 )alkyl group, each of Q 1 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 nitro group, a (C 1 -C)alkyl group, a halo(Cl-C 6 )alkyl group, a (C 2 -C 6 )alkenyl group, a halo(C 2 -C 6 )alkenyl group, a (C 2 -C 6 )alkynyl group, a halo(C 2 -C 6 )alkynyl group, a (C-C)alkoxy group, a halo(Cl-C 6 )alkoxy group, a (Cl-C 6 )alkylthio group, a halo (Ci-C 6 )alkylthio group, a (Ci-C) alkylsulfinyl group, a halo (C 1 -C 6 )alkylsulfinyl group, a (C-C 6 alkylsulfonyl group or a halo(C 1 -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, (C 1 -C 6 )alkyl groups, halo(Ci-C 6 )alkyl groups, (Ci-C 6 )alkoxy groups, halo(Ci-C 6 )alkoxy groups, (Ci-C)alkylthio groups, halo(C-C 6 alkylthio grups, (C,-C 6 )alkylsulfinyl groups, halo(Cl-C 6 alkylsulfinyl groups, (Ci-C) alkylsulfonyl groups and halo(Ci-C 6 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)cycloalkyl group; a halo(C 3 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, (Cl-C)alkyl groups, halo(CI-C 6 )alkyl groups, (C 1 -C 6 )alkoxy groups, halo(C-C 6 )alkoxy groups, alkylthio groups, halo(C 1 -C 6 alkylthio groups, (Cl-C,)alkylsulfinyl groups, halo(C,-C,)alkylsulfinyl groups, alkylsulfonyl groups, halo (Cl-C 6 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; 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(Cl-C.)alkyl groups, (C 1 -C 6 )alkoxy groups, halo(Cl-C.) alkoxy groups, (C-C 6 alkylthio groups, halo(C-C 6 alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo alkylsulfinyl groups, alkylsulfonyl.- groups, halo (Cl-C 6 alkyl- sulfonyl groups, mono(Cl-C.) alkylamino groups, di(C,- C 6 )alkylamino groups whose (C 1 -C 6 )alkyl groups may be the same or different, and (C,-C)alkoxycarbonyl groups; or -A 5 -R 1 (wherein A 5 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; (Cl-C)alkyl groups; halo(Cl-C,)alkyl groups; (C 1 C 6 )alkoxy groups; halo(C 1 -C 6 ,)alkoxy groups; (C,-C,)alkyl- thio groups; halo(Cl-C 6 alkylthio groups; (Cl-C) alkyl- sulfinyl groups; halo(Cl-C 6 alkylsulfinyl groups; 135 C )alkylsulfonyl groups; halo(C 1 -C 6 )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, (Cl-C 6 )alkyl groups, halo(C 1 alkyl groups, (Cl- C )alkoxy groups, halo(C,-C,)alkoxy groups, (C,-C 6 )alkyl- thio groups, halo(C 1 -C 6 alkylthio groups, (C 1 -C 6 )alkyl- sulfinyl groups, halo(C-C)alkylsulfinyl groups, C 6 alkylsulfonyl groups, halo(C 1 -C 6 alkylsulfonyl groups, mono (Cl-C 6 ,)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; 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(C,-C,)alkyl groups, (C 1 C) alkoxy groups, halo(Cl-C) alkoxy groups, (C 1 -C 6 alkyl- thio groups, halo(Cl-C) alkylthio groups, (Cl-C)alkyl- sulfinyl groups, halo(C 1 -C 6 alkylsulfinyl groups, (C 1 C 6 alkylsulfonyl groups, halo(Cl-C 6 alkylsulfonyl groups, mono(Cl-C 6 ,)alkylamino groups, di (C-C 6 alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (C-C 6 ,)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 2 C )alkylene group; a substituted (Cl-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 (C 1 -C 6 alkyl groups, (Cl- alkoxy groups, halo (Cl-C 6 alkoxy groups, alkyl- thio groups, halo (C 1 -C 6 alkylthio groups, (Cl-C) alkyl- sulfinyl groups, halo (C 1 -C 6 alkylsulfinyl groups, C 6 )alkylsulfonyl groups, halo (C 1 -C 6 alkylsulfonyl groups, (Cl-C 6 alkylthio (C 1 -C 6 alkyl groups, (C,-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 which may be the same or different and are selected from halogen atoms, cyano group, nitro group, halo alkyl groups, (C 1 -C 6 alkoxy groups, halo alkoxy groups, (Cl-C 6 alkylthio groups, halo (Cl- alkylthio gop, (Cl-C 6 alkylsulfinyl groups, halo (C 1 -C 6 alkylsulfinyl gop, (Cl-C 6 alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl groups, (C 1 C 6 alkyl- thio (C 1 -C 6 alkyl, groups, (Cl-C 6 alkoxycarbonyl groups and phenyl group; a (C 3 -C)alkynylene group; or a substi- tuted (C 3 -C 8 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 6 alkyl groups, (Cl-C 6 alkoxy groups, halo (C 1 C 6 alkoxy groups, (Cl-C 6 alkylthio groups, halo (C 1 C 6 )alkylthio groups, (C-C 6 )alkylsulfinyl groups, halo alkylsulfinyl groups, (Cl-C 6 alkylsulfonyl groups, halo (C 1 -C 6 alkylsulfonyl groups, (C 1 -C 6 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 (C 2 -C 8 )alkylefle group, substituted (Cl- C)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 6 cycloalkane ring, and any two of the carbon atoms in the above-mentioned (C 2 -CB)alkylene group, substituted (Cl-C 8 )alkylene group, (C 3 CO)alkenylene group and substituted (C 3 -C 8 )alkenylele 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 or -N(R 4 (wherein R' is a hydrogen atom; a (Cl-C 6 )alkyl group; a haloa(Cl-C 6 alkyl group; a (C 3 -C 6 )alkenyl group; a halo (C 3 -C 6 )alkenyl group; a (C 3 Cs) alkynyl group-; a (C 3 -C 6 cycJ~oalky1 group; a (Cl- C 6 alkylcarbonyl group; a halo alkycarbonyl group; a (Cl-C 6 alkoxycarbonyl group; a phenylcarbony). 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 6 alkyl groups,. "halo (Cl-C 6 alkyl groups, C 6 alkoxy groups, halo (C,-C 6 alkoxy groups, (Cl-C 6 alkyl- thio groups, halo alkylthio groups, (C 1 -C 6 alkyl- sulfinyl groups, halo (C 1 -C 6 alkylsulfinyl gop, C 6 alkylsulfonyl groups, halo (Cl-C 6 alkylsulfonyl g-roups,
138. mono alkylamino groups, and di (Cl-C 6 alkylamino groups whose (Cl-C 6 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 group, nitro group, (Cl-C,)alkyl groups, halo alkyl groups, (Cl-C 6 alkoxy groups, halo (Cl-C 6 alkoxy groups, (Cl-C 6 alkylthio groups, halo (Cl-C 6 alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (CC-C6) alkylsulfiflyl groups, (Cl-C 6 alkylsulfonyl groups, halo (Cl-C 6 alkyl- sulf'onyl groups, mono al1kyl amino groups, and di (Cj- C 6 )alkylamino groups whose (C,-C)alkyl groups may be the same or different; a phenyl(Cl-C 4 )alkyl group; or a substituted phenyl (CI-C 4 )alkyl group having on the ring one or moire 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-0 6 )alkyl groups, (Cl-C 6 alkoxy groups, halo alkoxy groups, alkylthio groups, hal-o(Cl-C 6 alkylthio groups, alkylsulfinyl groups, halo (Cl-C 6 alkylsulf inyl groups, (Cl-C 6 alkylsulfonyl groups, halo (Cl-C 6 alkyl- sulfonyl groups, mono al kyl amino groups, di (C 1 C 6 )alkylamino groupd whose (C,-C 6 )alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups), R 1 is a hydrogen aiorn; .a (Cl-C 6 )alkyl group; a halo (C 1 alkyl group; a (C 1 -C 4 aJkQxy alkyl group; a (C 1 -C 4 )alkylthio (Cl-Cd)alkyl group; a (C 2 139 CO)alkenyl group; a halo(C-C,)alkenyl group; a (C 3 C)alkynyl group; a halo(C 3 -C 6 alkynyl group; a (C 3 CO)cycloalkyl group; a halo(C 3 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,) alkyl -groups, (C- C 6 )alkoxy groups, halo(C,-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-C 6 )alkylsulfinyl groups, C 6 alkylsulfonyl groups, halo (Cl-C) alkylsulfonyl groups, morlo (C 1 -C 6 ,)alkylamino groups, di(C,-C) alkylamino groups- whose (C-C 6 ,)alkyl groups may be the same or different, and 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, (C,-C)alkyl groups, halo(Cl-C 6 )alkyl groups, (Cl-C 6 alkoxy groups, halo(C 1 -C 6 alkoxy groups, (Cl-C)alkylthio groups, halo(C,-C.) alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo (C 1 -C 6 alkylsulfinyl groups, (Cl-C 6 )alkylsulfonyl groups, halo(C 1 -C 6 )alkyl- sulfonyl groups, mono(C 1 -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; 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, (01-C6) alkyl groups, halo(C-C6) alkyl groups, (Cl-C 6 alkoxy groups, halo (0-C6) alkoxy groups, (C-C 6 alkylthio groups, halo(Cl-C6) alkylthio groups, alkylsulfinyl groups, halo(C-C 6 alkylsulfinyl groups, (C-C6)alkylsulfonyl groups, halo(Cl-C) alkyl- sulfonyl groups, mono(Cl-C) alkylamino groups., di(C,- C,)alkylamino groups whose (Cl-C 6 )alkyl groups may be the same or different, and (Cl-C)alkoxycarbonyl groups; (R 6 (wherein W 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 gro.up; a halo(C,-C6)alkyl group; a (C,-C 4 alkoxy (Cl- 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 substituents which may be the same or different and are selected from -halogen atoms, cyano group, nitro group, (C-C 6 alkyl groups, halo alkyl groups, (Cl- C6)alkoxy groups, halo(Cl-C 6 alkoxy groups, (Cl-C 6 alkyl- thio groups, halo(C,-C) alkylthio groups, (C 1 -C 6 alkyl- sulfinyl groups, halo(C 1 -C 6 alkylsulfinyl groups, (C 1 C 6 alkylsulfonyl groups, halo(C 1 alkylsulfonyl groups, mono (Cl-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 6 )alkoxycarbonyl groups; a phenyl(Cl-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-C6)alkyl groups, halo (C-C6) alkyl 141 groups, alkoxy groups, halo (C 1 -C 6 )alkoxy groups, (C-C 6 alkylthio groups, halo(C 1 -C 6 alkylthio groups, (Cl-C 6 alkylsulfinyl groups, halo(C-C 6 alkylsulfinyl groups, .(C-C 6 alkylsulfonyl groups, halo (Cl-C 6 alkyl- sulfonyl groups, mono(Cl-C 6 alkylamino groups, di(Cl- C,)alkylamino groups whose (C,-C,)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(Cl-C 6 )alkyl groups, (Cl-C,)alkoxy groups, halo(Cl-C 6 )alkoxy groups, (CI-C)alkylthio groups, halo alkyithio groups, (Cl-C 6 alkylsulfinyl groups, halo(C 1 alkylsulfinyl groups, (Cl-C 6 )alkylsulfonyl groups, halo(C-C 6 alkyl- sulfonyl groups, mono(Cl-C)alkylamino groups, di(Cl- C )alkylamino groups whose (Cl-C)alkyl groups may be the same or different, and (C,-C)alkoxycarbonyl groups, 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 142 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); S (wherein W 1 and R 5 are as defined above); -C -W'-R 7 (wherein W's, which may be the same or different, are as defined above, and R 7 is a (C 1 -C,)alkyl group; a halo(Ci- C)alkyl group; a (C-C 4 )alkoxy(C-C 4 )alkyl group; a C4)alkylthio (Cl-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, (Cl-C 6 )alkyl groups, halo(C 1 -C 6 alkyl groups, (C 1 C)alkoxy groups, halo(Cl-C) alkoxy groups, (Ci-C) alkyl- thio groups, halo(Ci-Cg) alkylthio groups, (C-C6) alkyl- sulfinyl groups, halo (C-C6) alkylsulfinyl groups, C,)alkylsulfonyl groups, halo(C 1 -C,)alkylsulfonyl groups, mono (Ci-C) alkylamino groups, di(Ci-C 6 alkylamino groups whose (Ci-C6)alkyl groups may be the same or different, and (C-C6) alkoxycarbonyl groups; a phenyl (Cl-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, (C1-C6)alkyl groups, halo(Ci-C 6 )alkyl groups, (Cl-C6)alkoxy groups, halo(C-C6)alkoxy groups, (Ci-C) alkylthio groups, halo(Cl-C) alkylthio groups, (Ci-C6) alkylsulfinyl groups, halo(Ci-C 6 alkylsulfinyl 143 groups, (C 1 alkylsulfonyl groups, halo(C-C 6 alkyl- sulfonyl groups, mono(C 1 -C 6 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; 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, (C 1 -C 6 )alkoxy groups, halo(Ci-C) alkoxy groups, (C.-C 6 alkylthio groups, halo (C-Cg) alkylthio groups, (Ci-C 6 alkylsulfinyl groups, halo (C 1 -C 6 alkylsulfinyl groups, (Ci-C) alkylsulfonyl groups, halo (CI-C 6 alkyl- sulfonyl groups, mono (C 1 alkylamino groups, di(Ci- C 6 )alkylamino groups whose (Ci-C 6 )alkyl groups may be the same or different, and (Cl-C,)alkoxycarbonyl groups); -SO2-R 7 (wherein R 7 is as defined above); -SO2-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 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 RS and R 6 are as defined above, R 5 being able to bind to R 6 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 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 consti- tuting the ring); or -N=C(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 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 1 being able to 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 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 W 1 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 1 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 or a (Ci-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 6 )alkyl group, a halo(C,-C 6 )alkyl gr6up, a (C 2 -C 6 )alkenyl group, a halo(C 2 -C 6 alkenyl group, a (C 2 -C 6 )alkynyl group, a halo(C 2 -C 6 alkynyl group, a (Cl-C 6 alkoxy group, a hald(C 1 alkoxy group, a (C-C 6 )alkylthio group, a halo(C,-C 6 alkylthio group, a (C 1 alkylsulfinyl group, a halo(C,-C) alkylsulfinyl group, a (C-C 6 )alkylsulfonyl group or a halo(C,- 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, (C,-C 6 )alkyl groups, halo(C-C 6 )alkyl groups, (Ci-C 6 )alkoxy groups,. halo (C,-C 6 alkoxy groups, (Ci-C) alkylthio groups, halo(CI-C 6 alkylthio groups, (Ci-C) alkylsulfinyl groups, halo (C 1 -C 6 alkylsulfinyl groups, alkylsulfonyl groups and halo(Ci-C 6 alkyl- sulfonyl groups, n is an integer of 0 to 2, 146 Q 5 is a carbon atom or a nitrogen atom, each of Ys, which may be the same or different, is a halogen atom; a (C 1 -C 6 )alkyl group; a halo(Cl-C 6 )alkyl group; a (C 3 -C 6 )cycloalkyl group; a halo(C 3 -C,)cycloalkyl group; a (Cl-C 6 )alkoxy group; a halo(C-C 6 alkoxy group; a (C 1 C) alkylthio group; a halo(C-C 6 alkylthio group; a (CI- C )alkylsulfinyl group; a halo(Cl-C)alkylsulfinyl group; a (Cl-C)alkylsulfonyl group; a halo(CI-C,) alkylsulfonyl group; a halo(C 1 -C 6 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(C 1 alkyl groups, halo(C-C 6 alkoxy groups, halo (Cl-C 6 alkylthio groups, halo(Cl-C 6 alkylsulfinyl groups and halo(C 1 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(C,- C )alkyl groups, halo(Cl-C,)alkoxy groups, halo(C 1 C 6 ,)alkylthio groups, halo(C-C 6 alkylsulfinyl groups and halo(C 1 -C 6 )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- C 6 )alkyl groups, halo(C 1 -C,)alkoxy groups, halo(C 1 C )alkylthio groups, halo(Cl-C,)alkylsulfinyl groups and halo (C 1 -C 6 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, (C,-C 6 )alkyl groups, halo(C 1 alkyl groups, (C 1 C) alkoxy groups, halo(C 1 -C 6 alkoxy groups, (Ci-C 6 alkyl- thio groups, halo(Ci-C) alkylthio groups, (Cl-C) alkyl- sulfinyl groups, halo(C--C)alkylsulfinyl groups, (Ci- C 6 )alkylsulfonyl groups, halo(Cl-C) 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(Ci-C,)alkoxy groups, halo(Cl-C 6 alkylthic groups, halo(C--C 6 alkylsulfinyl groups and halo(Cl- C 6 )alkylsulfonyl groups, m is an integer of 1 to 3, and each of Z 1 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. 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. 8. A compound according to any one of claims 1 to 3 substantially as hereinbefore described with reference to tables 1 and 2. DATED this 2 0 t h day of June, 2003 Nihon Nohyaku Co., Ltd. By DAVIES COLLISON CAVE Patent Attorneys for the Applicants
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
JP36540899 1999-12-22
JP11-365408 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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