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MX2007016241A - Amide derivative, pesticide containing such compound and use thereof. - Google Patents

Amide derivative, pesticide containing such compound and use thereof.

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Publication number
MX2007016241A
MX2007016241A MX2007016241A MX2007016241A MX2007016241A MX 2007016241 A MX2007016241 A MX 2007016241A MX 2007016241 A MX2007016241 A MX 2007016241A MX 2007016241 A MX2007016241 A MX 2007016241A MX 2007016241 A MX2007016241 A MX 2007016241A
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MX
Mexico
Prior art keywords
group
atom
haloalkylsulfonyl
alkyl
haloalkylsulfinyl
Prior art date
Application number
MX2007016241A
Other languages
Spanish (es)
Inventor
Kei Yoshida
Nobuyuki Kawahara
Michikazu Nomura
Hidenori Daido
Yumi Kobayashi
Shinichi Inomata
Original Assignee
Mitsui Chemicals Inc
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Publication date
Application filed by Mitsui Chemicals Inc filed Critical Mitsui Chemicals Inc
Publication of MX2007016241A publication Critical patent/MX2007016241A/en

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  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Disclosed are a compound represented by the general formula (1) below which exhibits a high insecticidal effect, and a pesticide containing such a compound as an active ingredient. (1) (In the formula, A<sub>1</sub>, A<sub>2</sub>, A<sub>3</sub> and A<sub>4</sub> respectively represent a carbon atom or the like; R<sub>1</sub> and R<sub>2</sub> respectively represent a hydrogen atom, an alkyl group or the like; G<sub>1</sub> and G<sub>2</sub> respectively represent an oxygen atom or the like; X represents a hydrogen atom, a halogen atom or the like; n represents an integer of 0-4; Q<sub>1</sub> represents a substituted phenyl group, a substituted heterocyclic group or the like; and Q<sub>2</sub> represents a phenyl group having a haloalkylthio group or the like, a heterocyclic group or the like.).

Description

AMID DERIVATIVE, INSECTICIDE CONTAINING SUCH COMPOSITE AND USE OF THEM Field of the Invention The present invention relates to novel amide derivatives, to an insecticide containing the compound in the form of an active ingredient, to an intermediate in the production of the compound and to a method for the application thereof as an insecticide. Background of the Invention In WO 2000/55120 and in US Patent Number 6548514, a compound similar to the compound represented by the general formula (1) for medical use was described. Although insect activity is never described in the present invention. Furthermore, it is obvious that said compounds are not included in the claims of the present invention. In WO 2000/7980, a compound similar to the compound represented by the general formula (1) for medical use was described. Although the activity against insects was never described. Furthermore, it is obvious that said compound is not included in the claims of the present invention. In the North American Patent that remains pending Number 2002-032238, a compound similar to the compound represented by the general formula (1) for medical use. Although the activity against insects was never described. Furthermore, it is obvious that said compound is not included in the claims of the present invention. Brief Description of the Invention The present invention provides a novel compound that exhibits a broad spectrum of insecticidal properties against insect pests of various crops and which also has a superior insecticidal effect on insect pests having a resistance which has recently become in a severe problem also, an insecticide containing the compound in the form of an active ingredient, and an insecticide application method. In order to solve the above objects, the inventors of the present invention have repeatedly carried out an extensive study and as a result, have discovered a novel use of a compound of the present invention as an insecticide, because the compound of the present invention is a novel compound that is not described in any of the documents and has an excellent insecticidal effect. It was found that the compound of the present invention not only exhibits an insecticidal effect in various insect pests, but also has an excellent insecticidal effect in insect pests that are difficult to control such as LEPIDOPTERA, THYSANOPTERA, and the like, which have become a problem worldwide. In addition, the inventors have discovered a new preparation method and usual intermediate for the production of the compound of the present invention. Therefore, in this way the present invention has been completed. Therefore, the present invention is specified through the following aspects [1] A compound represented by the general formula (1), where, in the formula, Ai, A2, A3, and A4 > each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom; R t and R 2 are each independently a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkylcarbonyl group; Gt and G2 are each independently an oxygen atom or a sulfur atom, Xs are each independently a hydrogen atom, a halogen atom, or a trifluoromethyl group; n represents an integer from 0 to 4; QT is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group , a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, a group C 1 -C 4 alkylcarbonyl, a C 1 -C 4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a N group) pyridine oxide, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, an triazolyl group, a pyrrole group, a pyrazolyl group or a group tetrazolyl), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, an alkoxy group of C1-C3, a haloalkoxy group of C1-C3, an alkylthio group of C1-C3, a haloalkylthio group of C1-C3, an alkylsulfinyl group of C1-C3, a haloalkylsulfinyl group of C1-C3, an alkylsulfonyl group of C1 -C3, a haloalkylsulfonyl group of C1-C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, an alkylcarbonyl group of C1- C4, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group, (The group heterocyclic represents the same as those described above); and Q2 is represented by the general formula (2) or (3), where, in the formula, Yi represents an alkoxy group of C1-C4, a haloalkoxy group of C1-C4, a haloalkylthio group of C1-C3, a haloalkisulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group of C1-C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Y6 and Y9 each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkylthio group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulfonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Yg must represent a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , a haloalkylthio group of C 1 -C 3, a haloalkylsulfinyl group of C 1 -C 3 or a haloalkylsulfonyl group of C 1 -C 3); [2] a compound represented by the general formula (1), wherein, in the formula, Ai, A2, A3, and A, each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom; R 1 and R 2 each independently represent a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkylcarbonyl group; Gi and G2 each independently represent an oxygen atom or a sulfur atom, Xs each independently represent a hydrogen atom, a halogen atom, or a trifluoromethyl group; n represents an integer from 0 to 4; Qi is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group , a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a group nitro, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, a isothiazolyl group, an imidazolyl group, a group triazolyl, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, an alkyl group of C1 -C4, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group , a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a group nitro, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, an alkoxycarbonyl group of C1-C4, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described above); and Q2 is represented by the general formula (2) or (3), (2) wherein, in the formula, Yi represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group of C1-C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Y6 and Y9 each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , an alkylthio group of C1-C3, a haloalkylthio group of C1-C3, a group alkylsulfinyl of C1-C3, a haloalkylsulfinyl group of C1-C3, a group C 1 -C 3 alkylsulfonyl, a C 1 -C 3 haloalkylsulfonyl group or a cyano group; Y8 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkylthio group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulfonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Y9 must represent a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group), therefore, compounds are excluded, wherein Y represents a trifluoromethylthio group; Y2 and Y represents hydrogen atoms; Y3 represents a heptafluoroisopropyl group; Y 5 represents a bromine atom; X represents a hydrogen atom; G and G2 represent oxygen atoms; R, and R2 represent hydrogen atoms; and Q- represents an unsubstituted phenyl group; [3] the compound as described in [1] or [2], represented by the general formula (1a), wherein A ,, A2, A3 and A4 in the general formula (1), are all carbon wherein, in the formula, when any of Ri and R2 are a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both of Ri and R2 are C1-6 alkyl groups C4 or C1-C4 alkylcarbonyl groups; d and G2 are each independently an oxygen atom or a sulfur atom; Xi, X2, X3, and X4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; Q1 is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group , a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, an alkylsulfonyl group of C1-C3, a haloalkylsulfonyl group of C1-C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, an alkylcarbonyl group of C1-C4, an alkylcarbonyloxy group of C1-C4, an alkoxycarbonyl group C1-C4, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group herein represents a pyridyl group, an N-oxide of pyridine, a pyrimidinyl group, a pyridazyl group, one pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group ), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a group C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C2-C4, cycloalkyl group of C3-C6 a halocycloalkyl group C3-C6, an alkoxy group C1-C3, a haloalco group xi C1-C3 alkylthio group of C1-C3 alkyl, halo-C1-C3 alkylsulfinyl C1-C3 a haloalkylsulfinyl group C1-C3 alkylsulfonyl group of C1-C3 a haloalkylsulfonyl group C1-C3, an amino group, a C1-C4 alkylamino group, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, an alkylcarbonyloxy group of C1 -C4, a C 1 -C 4 alkoxycarbonyl group, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described above); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, Yi represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y5 represents a halogen atom, an alkyl group C1-C4, haloalkyl C1-C4 group, an alkoxy group C1-C4, haloalkoxy C1-C4 group, an alkylthio group of C1-C3 haloalkylthio group one C1-C3 alkylsulfinyl C1-C3 haloalkylsulfinyl group one C1-C3 alkylsulfonyl group of C1-C3 haloalkylsulfonyl group one C1-C3 or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; (3) wherein, in the formula, Y6 and Y9 each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkylthio group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulfonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Y9 must represent a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a C1-C3 haloalkylsulfonyl group); [4] the compound as described in [3], characterized in that Q2 is represented by the general formula (2) wherein, in the formula, Y-i represents a haloalkylthio group of C 1 -C 3, a haloalkylsulfinyl group of C 1 -C 3 or a haloalkylsulfonyl group of C 1 -C 3; Y5 represents an atom of halogen, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a C 1 -C 3 haloalkylthio group , a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or [5] the compound as described in [4], characterized in that Q ^ represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a haloalkynyl group of C2- C4, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a group C1-C3 haloalkylsulfonyl, an amino group, a C1-C4 alkylamino group, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, an alkylcarbonyloxy group of C1-C4, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (substituents are selected of a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a haloalkynyl group of C2-C4, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1- C3 haloalkyl group C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a haloalkyl group C1-C3-ilsulfonyl, an amino group, a C1-C4 alkylamino group, a C1-C4 di-alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, an alkylcarbonyloxy group of C1-C4, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group); [6] the compound as described in [1] or [2], represented by the general formula (1a), wherein Ai, A2, A3 and A4 in the formula (1), are all carbon atoms wherein, in the formula, R and R2 each independently represent a hydrogen atom, a C1-C4 alkyl group, or a C1-C4 alkylcarbonyl group; Gi and G2 are each independently an oxygen atom or a sulfur atom; Xi, X2, X3, and X4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; Qi is a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, an alkenyl group of C2-C4, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1 alkoxy group -C3, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group , a group C1-C3 haloalkylsulfonyl, an amino group, a C1-C4 alkylamino group, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, an alkylcarbonyloxy group of C1-C4, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a group pyrazolyl or a tetrazolyl group), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a haloalkyl group of C1 -C4, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, an alkoxy group of C1-C3, a haloalkoxy group of C1-C3, an alkylthio group of C1-C3, a haloalkylthio group of C1-C3, an alkylsulfinyl group of C1-C3, a haloalkylsulfinyl group of C1-C3, an alkylsulfonyl group of C1 -C3, a group C1-C3 haloalkylsulfonyl, an amino group, a C1-C4 alkylamino group, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, an alkylcarbonyloxy group of C1-C4, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described above); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, Yi represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group of C1-C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; wherein, in the formula, Y6 and Yg each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkylthio group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulfonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Ye and YT must represent a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a C1-C3 haloalkylsulfonyl group); [7] the compound as described in [6], characterized in that Qi represents a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, an alkyl group of C1-C4, a group C1-C4 haloalkyl, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a halocycloalkyl group of C3-C6, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1- C3 haloalkylsulfinyl group C3, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group , a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a haloalkyl group), ilo of C1-C4, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a halocycloalkyl group of C3-C6, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1- C3 haloalkylsulfinyl group C3, a C1-C3 alkylsulfonyl group, a group C1-C3 haloalkylsulfonyl, an amino group, a C1-C4 alkylamino group, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, an alkylcarbonyloxy group of C1-C4, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group); and Q2 is represented by the general formula (2), wherein, in the formula, Yi represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group of C1-C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; [8] the compound as described in [1] or [2], represented by the general formula (1a), wherein A-i, A2, A3 and A in the general formula (1) are all carbon atoms wherein, in the formula, Ri and R2 are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, and G2 are each independently an oxygen atom or an oxygen atom. sulfur; Xi, X2, X3, and X4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; Qi is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group , a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1- C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, a oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group having one or more substituents which may be the same or different (the sust are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a haloalkylthio group of C1-C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1- C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described above); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, Y ^ represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a fluorine atom, a chlorine atom, an iodine atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a group C 1 -C 3 alkylthio, a C 1 -C 3 haloalkylthio group, a C 1 -C 3 alkylsulfinyl group, a C 1 -C 3 haloalkylsulfinyl group, a C 1 -C 3 alkylsulfonyl group, a C 1 -C 3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a group C 1 -C 6 perfluoroalkylsulfinyl or a C 1 -C 6 perfluoroalkylsulfonyl group; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Y6 and Yg each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyan group; Y8 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkylthio group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulfonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Yg must represent a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a C1-C3 haloalkylsulfonyl group); [9] the compound as described in [8], characterized in that Qi represents a phenyl group a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, an C 2 alkenyl group -C4, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group , a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, an alkylcarbonyl group of C1-C4, a group C 1 -C 4 alkylcarbonyloxy, a C 1 -C 4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a pyridyl group, or a p-group substituted iridyl having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group , a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3- halocycloalkyl group C6, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group); and Q2 is represented by the general formula (2), wherein, in the formula, Yi represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a fluorine atom, a chlorine atom, an iodine atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a group C 1 -C 3 alkylthio, a C 1 -C 3 haloalkylthio group, a C 1 -C 3 alkylsulfinyl group, a C 1 -C 3 haloalkylsulfinyl group, a C 1 -C 3 alkylsulfonyl group, a C 1 -C 3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a group C 1 -C 6 perfluoroalkylsulfinyl or a C 1 -C 6 perfluoroalkylsulfonyl group; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; [10] a compound as described in [1] or [2], represented by the general formula (1a), wherein AL A2, A3 and A in the general formula (1), are all carbon atoms wherein, in the formula, Ri and R2 are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group; d and G2 are each independently an oxygen atom or a sulfur atom; Xi. X2- X3, and X4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; Q is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, an alkylthio group of C1-C3, a haloalkylthio group of C1-C3, an alkylsulfinyl group of C1-C3, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group , an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group having one or more substituents which may be the same or different (substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, an alkylthio group of C1-C3, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an C 1 -C 4 alkylamino group, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group C4, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described above); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, Yi represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group of C1- C3, a C1-C3 alkylsulfinyl group, a group C1-C3 haloalkylsulfinyl, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Y6 and Yg each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkylthio group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulfonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Y9 must represent a haloalkylthio group of C2-C3, a group C1-C3 haloalkylsulfinyl or a C1-C3 haloalkylsulfonyl group); [11] the compound as described in [10], characterized in that Qi represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from an halogen, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a group C1-C3 alkylsulfinyl, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4 , a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a upo C 1 -C 4 alkoxycarbonyl, an acetylamino group and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkenyl group, a C 2 -C 4 haloalkenyl group, a C 2 -C 4 alkynyl group, a C 2 -C 4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1- C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group); and Q2 is represented by the general formula (2), wherein, in the formula, Yi represents a haloalkylthio group of C2-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group from C1- C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; [12] the compound as described in [1], represented by the general formula (1), wherein, in the formula, A1t A2, A3 and A each independently represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom; wherein, any of RT and R2 is a hydrogen atom, the other is a C1-C6 alkyl group or a C1-C4 alkylcarbonyl group, or both of Ri and R2 are C1-C4 alkyl groups or alkylcarbonyl groups of C1-C4. G and G2 are each independently an oxygen atom or a sulfur atom, Xs are each independently a hydrogen atom, a halogen atom, or a trifluoromethyl group; n represents an integer from 0 to 4; Q is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group , a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, an alkylsulfonyl group of C1-C3, a haloalkylsulfonyl group of C1-C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, an alkylcarbonyl group of C1-C4, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a group heterocyclic (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a group triazolyl, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, an alkyl group of C1 -C4, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group , a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a group nitro, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, an alkoxycarbonyl group of C1-C4, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described above); and Q2 is represented by the general formula (2) or (3), (2) wherein, in the formula, Yi represents a C 1 -C 4 alkoxy group or a C 1 -C 4 haloalkoxy group; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group of C1-C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Y6 and Yg each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a haloalkoxy group of C1-C4, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Yg must represent a C1-C4 alkoxy group or a C1-C4 haloalkoxy group. ); [13] the compound as described in [12], represented by the general formula (1a), wherein A-, A2, A3 and A in the general formula (1), are all carbon atoms wherein, in the formula, any of Ri and R2 is a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both of Ri and R2 are C1-C4 alkyl groups or C1-C4 alkylcarbonyl groups; Gi and G2 are each independently an oxygen atom or a sulfur atom; Xi. X2, X3 > and X4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; Qi is a phenyl group, a substituted phenyl group that has one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkenyl group, a C 2 - haloalkenyl group C4, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a group amino, a C1-C4 alkylamino group, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, an alkoxycarbonyl group of C1-C4, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkenyl group, a C 2 - haloalkenyl group C4, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group , a C 1 -C 4 alkylamino group, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, an alkoxycarbonyl group of C1-C4, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described above); and Q2 is represented by the general formula (2), wherein, in the formula, Yi represents a haloalkoxy group of C 1 -C 4; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a group C 1 -C 4 alkoxy, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a C 1 -C 3 haloalkylthio group, a C 1 -C 3 alkylsulfinyl group, a C 1 -C 3 haloalkylsulfinyl group, an alkylsulfonyl group of C1-C3, a haloalkylsulfonyl group of C1-C3 or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; [14] the compound as described in [13], characterized in that Q-representa represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (substituents are selected from an atom of halogen, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group , a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1- C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, an alkenyl group of C2- C4, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a group C1-C3 haloalkylsulfonyl, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a group ci an, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group); [15] a compound represented by the general formula (4), (4) / "Q, a wherein, in the formula, R 2 represents a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkylcarbonyl group; and Q2 is represented by the general formula (2), (3) or (5), where, in the formula Y1t Y2, Y3, Y4, and Y5 represent the same as those described in [1], where, in the formula Y6, Y, Y8, and Yg represent the same as those described in [1], or wherein, in the formula, Ra and Rb each independently represent a fluorine atom or a perfluoroalkyl group of C 1 -C 4; Rc is a hydroxy group -O-Rd (Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an aryisulfonyl group, a group C 1 -C 4 alkylcarbonyl or a C 1 -C 4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom; Yia represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5a represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-6 alkylthio group, C3, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; and Y2a and Y4a each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; [16] a process for preparing the compound as described in any of [1] to [14] and [21], characterized in that it comprises reacting the compound represented by the general formula (4) as described in [15]. ] with a compound represented by the general formula (6), where, in the formula, A1t A2, A3, and A4 each independently represent a carbon atom, an atom of nitrogen or an oxidized nitrogen atom; Ri represents a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group; d and G2 each independently represent an oxygen atom or a sulfur atom; X represents a hydrogen atom, a halogen atom or a trifluoromethyl group; n represents an integer from 0 to 4; Qi represents the same as those described in [1]; and Hal represents a chlorine atom or a bromine atom; [17] a compound represented by the general formula (7), wherein, in the formula, A1 t A2, A3, and A each independently represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom; R 2 is a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkylcarbonyl group; G2 is an oxygen atom or a sulfur atom; X is a hydrogen atom, a halogen atom or a trifluoromethyl group; n represents an integer from 0 to 4; and Q2a represents the same as those described in [15]; [18] a process for the preparation of such compound as described in [15]; [18] characterized in that it comprises reacting a compound represented by the general formula (8) with a compound represented by the general formula (4) as described in [15] wherein, in the formula, A-i, A2, A3, and A each independently represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom; G2 is an oxygen atom or a sulfur atom; and J represents a halogen atom or a hydroxy group; [19] a compound represented by the general formula (9), wherein, in the formula, A1f A2, A3, and A4 each independently represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom; R 1 and R 2 each independently represent a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkylcarbonyl group; G2 is an oxygen atom or a sulfur atom; Xs is a hydrogen atom, a halogen atom or a trifluoromethyl group; n represents an integer from 0 to 4; and Q2a represents the same as those described in [15]; [20] a process for preparing the compound represented by the general formula (9) as described in [19]; characterized in that it comprises reacting the compound represented by the general formula (7) as described in [17] in the presence of a suitable reducing agent; [21] a compound represented by the general formula (10), wherein, in the formula, A ,, A2, A3, and A each independently represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom; R 1 and R 2 each independently represent a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkylcarbonyl group; GT and G2 each independently represent an oxygen atom or a sulfur atom, X is a hydrogen atom, a halogen atom, or a trifluoromethyl group; n represents an integer from 0 to 4; QT represents the same as those described in [1]; and Q2b is represented by the general formula (5), wherein, in the formula, Ra and R each independently represent a fluorine atom or a perfluoroalkyl group of C 1 -C 4; Rc is a hydroxy group -O-Rd (Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an aryisulfonyl group, a group C 1 -C 4 alkylcarbonyl or a C 1 -C 4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom; Y-ia represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5a represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-6 alkylthio group, C3, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; and Y2a and Y4a each independently represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group; [22] a process for preparing the compound as described in any of [1] to [14] and [21], characterized in that it comprises reacting the compound represented by the general formula (9), as described in [ 19], with a compound represented by the general formula (11) or (12) where, in the formula, Gi represents an oxygen atom or a sulfur atom; J 'represents a halogen atom or a hydroxy group; and Qi represents the same as those described in [1], or where, in the formula, Qi represents the same as those described in [1]; [23] a process for preparing a compound represented by the general formula (14), where, in the formula, A ,, A2, A3, and A, each independently represents a carbon atom, an atom of nitrogen or an oxidized nitrogen atom; R 2 is a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkylcarbonyl group; G2 is an oxygen atom or a sulfur atom, X is a hydrogen atom, a halogen atom, or a trifluoromethyl group; n represents an integer from 0 to 4; Yia, Y2a, Y4a, Ysa, Ra and Rb each represent the same as those described in [15]; Rc "represents a chlorine atom, a bromine atom or an iodine atom, E represents a nitro group, -NH- (R?) (Ri represents a hydrogen atom, a C1-C4 alkyl group or an alkylcarbonyl group of C1-C4), -N (R1) -C (= Gi) Q? (Ri represents a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, d represents an oxygen atom or a sulfur atom, and Q- \ represents the same as those described in [1], wherein the process comprises reacting a compound represented by the general formula (13) with a suitable halogenating agent wherein, in the formula, AL A2, A3, and A4, each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom; R2 is a hydrogen atom, a C1-C4 alkyl group or an alkylcarbonyl group of C1-C4; G2 is an oxygen atom or a sulfur atom, X is a hydrogen atom, a halogen atom, or a trifluoromethyl group; n represents an integer from 0 to 4; Yia, Y2a, Y4a, Ysa, Ra and Rb each represent the same as those described in [15]; Rc 'represents a hydroxy group, -O-Rd (Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group); and E represents a nitro group, -NH- (R!) (Ri represents a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group) or -N (R1) -C (= G? ) Q? (Ri represents a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, d represents an oxygen atom or a sulfur atom, and Qi represents the same as those described in [1]); [24] a process for preparing a compound represented by the general formula (15), wherein the process comprises reacting the compound represented by the general formula (13) or the compound represented by the general formula (14) as described in [23] with a suitable fluorinating agent, (fifteen) where, in the formula, A ,, A2, A3, A4, X, n, R2, G2, Yia, Y2a, Y4a, Y5a, Ra, Rb and E represent the same as those described in [23], [25] ] an insecticide comprising the compound as described in any of [1] to [14] in the form of an active ingredient; and [26] a method for applying a chemical, wherein the method comprises applying an effective amount of the compound as described in any of [1] to [14] on crops or useful soil for the purpose of protecting useful crops against dangerous organisms. The compound of the present invention exhibits a control effect on various insect pests, protects useful crops and contributes greatly to the reduction of environmental load with a small amount of chemicals. Detailed Description of the Invention A compound of the present invention is represented by the general formula (1); wherein, in the formula Ai, A2, A3, and A, each represents a carbon atom, a nitrogen atom or an atom to the oxidized nitrogen; RT and R2 independently represent a hydrogen atom or a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group; Gi and G2 independently independently represent an oxygen atom or a sulfur atom, Xs can be the same or different and represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group or a trifluoromethyl group; n represents an integer from 0 to 4; Q represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group , a substituted C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a group C1-C3 haloalkylsulfinyl, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group , a C1-C4 alkylcarbonyl group, a C1- haloalkylcarbonyl group C4, a C1-C4 alkylcarbonyloxy group, a C1-C4 haloalkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a C1-C4 haloalkoxycarbonyl group, a C1-C4 alkylcarbonylamino group, a C1-C4 haloalkylcarbonylamino group, a C 1 -C 4 alkylsulfonyloxy group, a C 1 -C 4 haloalkylsulfonyloxy group, an arylsulfonyloxy group, a pentafluorosulfanyl group, a phenylalkynyl group and a phenyl group) a heterocyclic group (The heterocyclic group in the present invention represents a pyrazinyl group, pyridyl group , a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, an pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, a tetrazolyl group, a benzothiazolyl group, a benzoxazolyl group, a benzofuranyl group, a benzothiophenyl group, a quinolyl group , an isoquinolyl group, an indolyl group, an iso-indolyl group, a 1 H-isoindolyl group, a 2,3-dihydro-benzo [1,4] dioxinyl group, a benzo [1,3] dioxolyl group, a group tetrahydropyranyl, an acridinyl group or a dihydropyranyl group), or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C4 alkyl group, a haloalkyl group of C1-C4, an alkyl group of Substituted C1-C4, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C8 cycloalkyl group, a C3 halocycloalkyl group -C8, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group , a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a C1-C4 alkylamino group, an amino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 haloalkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a C1-C4 haloalkoxycarbonyl group, a group C 1 -C 4 alkylcarbonylamino, a C 1 -C 4 haloalkylcarbonylamino group, a C 1 -C 4 alkylsulfony group, a C 1 -C 4 haloalkylsulfonyloxy group, a polysulfonyloxy, a pentafluorosulfanyl group, a phenylalkynyl group and a phenyl group, (The heterocyclic group in the present invention represents the same as described above); and Q2 is represented by the general formula (2) or (3), (2) wherein, in the formula, Y represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5 represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 each independently represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Y6 and Y9 each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1 group -C3 alkylthio, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, or a cyano group; Y8 represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a group C1-C6 perfluoroalkylthio, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (At least one of Y6 and Yg must represent a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group.). A compound of the present invention can be represented by the general formula (10); wherein, in the formula, A ,, A2, A3 and A each independently represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom; Ri and R2 are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group; Gi and G2 are each independently an oxygen atom or a sulfur atom; X is a hydrogen atom, a halogen atom or a trifluoromethyl group; n represents an integer from 0 to 4; Qt is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 group alkylamino, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group) , a heterocyclic group (The heterocyclic group of the present invention represents a group pyridyl, a N-oxide pyridine group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group.), or a substituted heterocyclic group having one or more substituents which may be the same or different (the selected substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 di alkylamino group, a cyano group , a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group) (the heterocyclic group represents the same as those described above); and Q2b is represented by the general formula (5), wherein, in the formula, Ra and Rb are each independently a fluorine atom or a C1-C4 perfluoroalkyl group; Rc is a hydroxy group, -O-R (Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a group C1-C3 alkylsulfonyl, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom; Y represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5a represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1 group -C3 haloalkylthio, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; and Y2a and Y4a each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. The terms used in the general formulas, such as the general formula (1) of the present invention and the like, have the respective meanings which are described below in terms of definitions. The term "halogen atom" represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. In the expression of "Ca-Cb (a and b represent an integer not less than 1)", for example, "C1-C3" refers to 1 to 3 carbon atoms in the carbon chain, "C2-C6" is refers from 2 to 6 carbon atoms in the carbon chain, and "C1-C4" refers to 1 to 4 carbon atoms in the carbon chain. "n-" refers to normal, "i-" refers to iso, "s-" refers to secondary, and "t-" refers to tertiary. In addition, the term "C1-C3 alkyl group" refers to a straight or branched alkyl group having from 1 to 3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl or the like. The term "C 1 -C 4 alkyl group" refers to a straight or branched chain alkyl group having 1 to 4 carbon atoms such as n-butyl, s-butyl, i-butyl, t-butyl, cyclopropylmethyl or the like in addition to "C1-C3 alkyl group". The term "C1-C6 alkyl group" refers to a straight or branched chain alkyl group having from 1 to 6 carbon atoms such as n-pentyl, 2-pentyl, 3-pentyl, neopentyl, n-hexyl, -hexyl, 4-methyl-2-pentyl, 3-methyl-n-pentyl, cyclobutylmethyl or the like in addition to "C1-C4 alkyl group". The term "C1-C3 haloalkyl group" refers to a straight or branched chain group having from 1 to 3 carbon atoms which are substituted with one or more halogen atoms which may be the same or different, such as monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-chloroethyl, 2-chloroethyl, 2,2- dichloroethyl, 2,2,2-trichloroethyl, 1-bromoethyl, 2-bromoethyl, 2,2-dibromoethyl, 2,2,2-tribromoethyl, 2-iodoethyl, pentafluoroethyl, 3-fluoro-n-propyl, 3-chloro- n-propyl, 3-bromo-n-propyl, 1,3-difluoro-2-propyl, 1,3-dichloro-2-propyl, 1,1,1-trifluoro-2-propyl, 1-chloro- 3-fluoro-2-propyl, 1, 1, 1, 3,3,3-hexafluoro-2-propyl, 1,1,1,3,3-hexafluoro-2-chloro-2-propyl, 2, 2,3,3,3-pentafluoro-n-propyl, heptafluoro-i-propyl, heptafluoro-n-propyl or the like. The term "C1-C4 haloalkyl group" refers to a straight or branched chain alkyl group having 1 to 4 carbon atoms which are substituted with one or more halogen atoms which may be the same or different, such as such as 4-fluoro-n-butyl, 4-chloro-n-butyl, nonafluoro-n-butyl, nonafluoro-2-butyl or the like, in addition to a "C1-C3 haloalkyl group". The term "C2-C4 alkenyl group" refers to an alkenyl group of 2 to 4 carbon atoms that has double bond in the carbon chain such as vinyl, allyl, 2-butenyl, 3-butenyl or the like, and the "C2-C4 haloalkenyl group" refers to a straight or branched chain alkenyl group having 2 to 4 carbon atoms having double bond in the carbon chain, which is substituted with one or more halogen atoms which may be the same or different, such as 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2- propenyl, 2,3-dibromo-2-propenyl, 4,4-difluoro-3- butenyl, 3,4,4-tribromo-3-butenyl or the like. The term "C2-C4 alkynyl group" refers to a straight or branched chain alkynyl group of 2 to 4 carbon atoms having a triple bond in the carbon chain such as propargyl, 1-butin-3-yl, 1 -butin-3-methyl-3-yl or the like, and "C2-C4 haloalkynyl group" refers to a straight or branched chain alkenyl group having 2 to 4 carbon atoms having a triple bond on the carbon chain which is substituted with one or more carbon atoms, which may be the same or different. The term "C3-C6 cycloalkyl group" refers to a cycloalkyl group of 3 to 6 carbon atoms having a ring structure, such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl or the like, and "C3-C6 halocycloalkyl group" refers to a cycloalkyl group of 3 to 6 carbon atoms having a ring structure which is substituted with one or more halogen atoms which may be the same or different, such as 2, 2,3,3-tetrafluorocyclobutyl, 2-chlorocyclohexyl, 4-chlorocyclohexyl or the like. The term "C1-C3 alkoxy group" refers to a straight or branched chain alkoxy group having from 1 to 3 carbon atoms such as methoxy, ethoxy, n-propyloxy, isopropyloxy or the like, and "C1-C4 alkoxy group. "refers to a straight or branched chain alkoxy group having 1 to 4 carbon atoms such as n-butyloxy, isobutyloxy, s-butyloxy, t-butyloxy or the like, in addition to "C1-C3 alkoxy group". The term "C1-C3 haloalkoxy group" refers to a straight or branched chain haloalkoxy group having 1 to 3 carbon atoms which are substituted with one or more halogen atoms which may be the same or different, such as as trifluoromethoxy, difluoromethoxy, monofluoromethoxy, pentafluoroethoxy, 1, 1, 3,3,3-hexafluoro-2-propyloxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, , 2-dichloroethoxy, 2,2,2-trichloroethoxy, 3-fluoro-n-propyloxy, 2,2,3,3-tetrafluoro-n-propyloxy, 2,2,3,3,3-pentafluoro-n-propyloxy , 1,3-difluoro-2-propyloxy, 1-chloro-3-fluoro-2-propyloxy, 1,1, 2,3,3,3-hexafluoropropyloxy, 2,2,2-trifluoro-1-trifluoromethylethoxy, -trifluoromethoxy-1, 1,2-tri-fluoro-ethoxy, 1,1,2,2-tetrafluoroethoxy or the like, and the "C1-C4 haloalkoxy group" refers to a straight or branched haloalkoxy group having from 1 to 4 carbon atoms, which are replaced with one more halogen atoms which may be the same or different, such as 1, 1, 1, 3,3,4, 4,4-octafluoro-2-butyloxy or the like, in addition to "C1-C3 haloalkoxy group". The term "C1-C3 alkylthio group" refers to a straight or branched chain alkylthio group having from 1 to 3 carbon atoms such as methylthio, ethylthio, n-propylthio, i-propylthio, cyclopropylthio or the like, the "group C1-C4 alkylthio "refers to a straight or branched chain alkylthio group having from 1 to 4 carbon atoms such as n-butylthio, i-butylthio, s-butylthio, t-butylthio, cyclopropylmethylthio or the like, in addition to "C1-C3 alkylthio group", "C1-C3 group haloalkylthio" refers to an alkylthio group of straight or branched chain having 1 to 3 carbon atoms which are substituted with one or more halogen atoms which may be the same or different, such as trifluoromethylthio, pentafluoroethylthio, 2-fluoroethylthio, 2,2,2-trifluoroethylthio , heptafluoro-n-propylthio, heptafluoro-i-propylthio, 1,1, 2,3,3,3-hexafluoropropylthio, 2,2,2-trifluoride or gold-1-trifluoromethylethylthio, 2-trifluoromethoxy-1,1, 2-trifluoroethylthio, 1, 1, 2,2-tetrafluoroethylthio or the like, and the "C1-C4 haloalkylthio group" refers to a straight or branched chain alkylthio group having from 1 to 4 carbon atoms which are substituted with one or more atoms of halogens which may be the same or different, such as nonafluoro-n-butylthio, nonafluoro-s-butylthio, 4,4,4-trifluoro-n-butylthio or the like, in addition to "C1-C3 haloalkylthio group". The term "C1-C3 alkylsulfin group" refers to a straight or branched chain alkylsulfinyl group having from 1 to 3 carbon atoms, such as methylisulfinyl, eti I its Ifyl, n-propi I its Ifyl, i- propylsulfinyl, cyclopropylsulphinyl or the like, and the "C1-C3 haloalkylsulfinyl group" refers to a straight or branched chain alkylsulfinyl group having from 1 to 3 carbon atoms which are substituted by one or more halogen atoms which may be the same or different, such as trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propy Isu If in i lo, heptafluoro-i-propylsulfinyl, 1,1, 2,3,3,3-hexafluoropropylsulfinyl, 2,2 , 2-trifluoro-1-trifluoromethylethylsulfinyl, 2-trifluoromethoxy-1,1,2-trifluoroethylsulfinyl, 1,1, 2,2-tetrafluoroethylsulfinyl or the like. The term "C1-C3 alkylsulfonyl group" refers to a straight or branched chain alkylsulfonyl group having from 1 to 3 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl or the like, and the "C1-C3 haloalkylsulfonyl group" refers to a straight or branched chain alkylsulfonyl group having from 1 to 3 carbon atoms which are substituted by one or more halogen atoms which may be the same or different, such as trifluoromethylsulfonyl , pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, 1,1, 2,3,3, 3-hexafluoropropylsulfonyl, 2,2,2-trifluoro-1-trifluoromethylethylsulfonyl, -trifluoromethoxy-1,1,2-trifluoroethylsulfonyl, 1,1, 2,2-tetrafluoroethylsulfonyl or the like.
The term "arylsulfonyl group" refers to an arylsulfonyl group of 6 to 14 carbon atoms having an aromatic ring, such as phenylsulfonyl, p-toluenesulfonyl, 1-naphthylsulfonyl, 2-naphthylsulfonyl, anthrylsulfonyl, phenanthrylsulfonyl, acenaphthylene disulfonyl or the like.
The term "C1-C4 alkylamino group" refers to a cyclic straight or branched chain alkylamino group having from 1 to 4 carbon atoms, such as methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, cyclopropylamino , 2,2,2-trifluoroethylamino or the like, and the "C1-C4 alkylamino group" refers to a straight or branched chain amino group which is substituted with two alkyl groups having from 1 to 4 carbon atoms which they may be the same or different, such as dimethylamino, diethylamino, N-ethyl-N-methylamino or the like. The term "C1-C4 alkylcarbonyl group" refers to a straight chain, branched or cyclic alkylcarbonyl group having from 1 to 4 carbon atoms, such as formyl, acetyl, propionyl, isopropylcarbonyl, cyclopropylcarbonyl or the like. The term "C1-C4 haloalkylcarbonyl group" refers to a straight or branched chain alkylcarbonyl group having 1 to 4 carbon atoms which are substituted with one or more halogen atoms, which may be the same or different, such as fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, bromoacetyl, iodoacetyl, 3,3,3-trifluoropropionyl, 2,2,3,3,3-pentafluoropropionyl or the like. The term "C1-C4 alkylcarbonyloxy group" refers to a straight or branched chain alkylcarbonyloxy group having from 1 to 4 carbon atoms, such as acetoxy, propionyloxy or the like.
The term "C 1 -C 4 alkoxycarbonyl group" refers to a straight or branched chain alkoxycarbonyl group having 1 to 4 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl or the like. The term "C1-C4 perfluoroalkyl group" refers to a straight or branched chain alkyl group having from 1 to 4 carbon atoms, which are all substituted with fluorine atoms, such as trifluoromethyl, pentafluoroethyl, heptafluoro-n- propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl or the like, and the "C2-C6 perfluoroalkyl group" refers to a straight or branched chain alkyl group having from 2 to 6 carbon atoms which are all substituted with fluorine atoms, such as pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl , perfluoro-n-pentyl, perfluoro-n-hexyl or similes. The term "C1-C6 perfluoroalkylthio group" refers to a straight or branched chain alkylthio group having from 1 to 6 carbon atoms which are all substituted with fluorine atoms, such as trifluoromethylthio, pentafluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, nonafluoro-n-butylthio, nonafluoro-2-butylthio, nonafluoro-i-butylthio, perfluoro-n-pentthylthio, perfluoro-n-hexylthio or the like . The term "C1-C6 perfluoroalkylsulfinyl group" refers to a straight or branched chain alkylsulfinyl group having from 1 to 6 carbon atoms which are all substituted with fluorine atoms, such as trifluoromethylsulfinyl, pentafluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl, nona fluoro-n-butylsulphyl, nonafluoro-2-butylsulfinyl, nonafluoro -i-butylsulfinyl, perfluoro-n-pentylsu If i or lo, perfluoro-n-hexylsulfinyl or the like. The term "C1-C6 perfluoroalkylsulfonyl group" refers to a straight or branched chain alkylsulfonyl group having from 1 to 6 carbon atoms which are all substituted with fluorine atoms, such as trifluoromethylsulfonyl, pentafluoroethylsulfonyl, heptafluoro-n-propylsulfonyl , heptafluoro-i-propylsulfonyl, nonafluoro-n-butylsulfonyl, nonafluoro-2-butylsulfonyl, nonafluoro-i-butylsulfonyl, perfluoro-n-pentylsulfonyl, perfluoro-n-hexylsulfonyl or the like. The compound represented by the general formula (1) of the present invention contains one or more asymmetric carbon atoms or asymmetric centers in their structural form in some cases, and in other cases has two or more optical isomers. The present invention also includes all the optical isomers and respective mixtures consisting of these isomers in any proportion. In addition, the compound represented by the general formula (1) of the present invention has two or more geometric isomers derived from a carbon-carbon double bond in its structural form in some cases. The present invention also includes all the respective geometric isomers and mixtures consisting of these isomers in any proportion. Preferred examples of the substituents or atoms of the compounds represented by the general formula (1) and the like of the present invention are described below.
Ai is preferably a carbon atom, a nitrogen atom or an oxidized nitrogen atom and at the same time A2, A3 and A are all carbon atoms, and most preferably all of AL A2, A3 and A are carbon atoms Ri is preferably a hydrogen atom, a C1-C4 alkyl group or an acetyl group, and more preferably a hydrogen atom, a methyl group or an ethyl group. R2 is preferably a hydrogen atom, a group C1-C4 alkyl or an acetyl group, and more preferably a hydrogen atom, a methyl group or an ethyl group. Both d and G2 are preferably oxygen atoms. X is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom or a fluorine atom. n is preferably 0, 1 or 2, and more preferably 0 or 1. Xi is preferably a hydrogen atom or an atom of halogen, and more preferably a hydrogen atom or a fluorine atom. X2 is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom. X3 and X4 are preferably hydrogen atoms. Qi is preferably a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from halogen atoms, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a group C1-C3 haloalkoxy, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group , a C1-C4 alkylamino group, a C1-C4 di alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group and a acetylamino group, a phenyl group), a pyridyl group, or a substituted pyridyl group that It has one or more substituents which are the same or different (the substituents are selected from halogen atoms, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2- group C4 alkenyl group, a C2-C4 haloalkenyl, a C2-C4 alkynyl group, a C2-C4 haloalkynyl, a C3-C6 group, a C3-C6 halocycloalkyl, a C1-C3 alkoxy, a C1-C3 haloalkoxy, C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl, an amino group, C1-C4 alkylamino, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group and an acetylamino group, a phenyl group), and more preferably a phenyl group, or a substituted phenyl group having 1 to 3 substituents which may be the same or different (the substituents are selected from a fluorine atom, a chlorine atom, an atom of bromine, an iodine atom, a methyl group, a trifluoromethyl group, a methoxy group, or n trifluoromethoxy group, a methylthio group, an metiisulfinilo group, a metiisulfonilo group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group), a pyridyl group, or a substituent pyridyl group having one or two substituents which may be the same or different (the substituents are selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an methyl group, a trifluoromethyl group, a methoxy group, a trifluoromethoxy group, a methylthio group, a metiisulfinilo group, a metiisulfonilo group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group). Q2 is preferably a substituted phenyl group or a substituted pyridyl group represented by the general formula (2) or (3), wherein Yi of the general formula (2) is preferably a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoro group -propylthio, a heptafluoro-i-propylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a heptafluoro-n-propylsulfinyl group, a heptafluoro-i-propylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a heptafluoro-n-propylsulfonyl group , a heptafluoro-i-propylsulfonyl group, a methoxy group, an ethoxy group, a trifluoromethoxy group, a pentafluoroethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group or a 2,2,2-trichloroethoxy group, and more preferably a trifluoromethylthio group, a pentafluoroethylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a trifluoromethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group or a group 2,2,2- trifluoroethoxy; Y 5 of the general formula (2) is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, 2-butyl, a trifluoromethyl group, a methylthio group, a metiisulfinilo group, a metiisulfonilo group, a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoro-i-propylthio group, a trifluoromethylsulfinyl group, pentafluoroetilsulfinilo, a group heptafluoro-n-propylsulfinyl group, a heptafluoro-i-propi Isulf i nile, a trifluoromethylsulfonyl group, a pentafluoroetilsulfonilo group, a heptafluoro-n-propylsulfonyl a heptafluoro-i-propylsulfonyl group, a cyano group, methoxy group, an ethoxy group, an n-propyloxy group, a trifluoromethoxy group, a pentafluoroethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group or a 2,2 group , 2-trichloroethoxy; Ye and Yg of the general formula (3) are each preferably independently a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a group trifluoromethyl, a methylthio group, a methylisulfinyl group, a methylisulfonyl group, a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoro-i-propylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a heptafluoro-n-propylsulfinyl group, a heptafluoro-i-propylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a heptafluoro-n-propylsulfonyl group, a heptafluoro-i-propylsulfonyl group, a cyano group, a methoxy group, an ethoxy group, an n-propyloxy group, a trifluoromethoxy group, a pentafluoroethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group or a 2,2,2-trichloroethoxy group; any of Y6 and Yg must be a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoro-n-propylthio group, a heptafluoro-i-propylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a heptafluoro-n-propylsulfinyl group, a heptafluoro group -i-propylsulfinyl, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a heptafluoro-n-propylsulfonyl group, a heptafluoro-i-propylsulfonyl group, a methoxy group, an ethoxy group, a trifluoromethoxy group, a pentafluoroethoxy group, a 2-fluoroethoxy group , a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group or a 2,2,2-trichloroethoxy group, and most preferably any of Ye and Yg must be a trifluoromethylthio group, a pentafluoroethylthio group, a trifluoromethylsulfinyl group , a pentafluoroethylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a trifluoromethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-tri group fluoroethoxy or a 2,2,2-trichloroethoxy group; Y2, Y4 and Y7 of the general formula (3) are preferably each independently a hydrogen atom, a halogen atom or a methyl group, and more preferably a hydrogen atom; Y3 is preferably a pentafluoroethyl group, a heptafluoro-n-propyl group, a heptafluoro-i-propyl group, a nonafluoro-n-butyl group, a nonafluoro-2-butyl group, a nonafluoro-i-butyl group, a trifluoromethylthio group , a pentafluoroethylthio group, a heptafluoro-n-propylthio group, a heptafluoro-i-propylthio group, a nonafluoro-n-butylthio group, a nonafluoro-2-butylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a heptafluoro group -propylsulfinyl, a heptafluoro-i-propylsulfinyl group, a nonafluoro-n-butylsulfinyl group, a nonafluoro-2-butylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a heptafluoro-n-propylsulfonyl group, a heptafluoro-i-propylsulfonyl group , a nonafluoro-n-butylsulfonyl group or a nonafluoro-2-butylsulfonyl group, a pentafluoroethoxy group, a 1,1,1,3,3,3-hexafluoro-i-propyloxy group, a group 1, 1, 2,3 , 3, 3-hexafluoropropyloxy, a 2,2,2-trifluoro-1-trifluoromethyl group letoxy, a 2-trifluoromethoxy-1,1,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group; and Y8 is preferably a pentafluoroethyl group, a heptafluoro-n-propyl group, a heptafluoro-i-propyl group, a nonafluoro-n-butyl group, a nonafluoro-2-butyl group, a nonafluoro-i-butyl group, a group trifluoromethylthio, a pentafluoroethylthio group, a group heptafluoro-n-propylthio, a heptafluoro-i-propylthio group, a nonafluoro-n-butylthio group, a nonafluoro-2-butylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a heptafluoro-n-propylsulfinyl group, a heptafluoro- i-propylsulfinyl, a nonafluoro-n-butylsulfinyl group, a nonafluoro-2-butylsulfinyl group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfonyl group, a heptafluoro-n-propylsulfonyl group, a heptfluoro-i-propylsulfonyl group, a nonafluoro-n- group butylsulfonyl, a nonafluoro-2-butylsulfonyl group, a pentafluoroethoxy group, a 1, 1, 1, 3,3,3-hexafluoro-i-propyloxy group, a 1, 1, 2,3,3, 3-hexafluoropropyloxy group, a 2,2,2-trifluoro-1-trifluoromethylethoxy group, a 2-trifluoromethoxy-1,1,2-trifluoroethoxy group or a 1,1,1-tetrafluoroethoxy group. L of the above-mentioned general formula is preferably a chlorine atom, a bromine atom or a hydroxy group. R ^ is preferably a hydrogen atom, a C1-C4 alkyl group or an acetyl group, and more preferably a hydrogen atom, a methyl group or an ethyl group. R2a is preferably a hydrogen atom, a group C1-C4 alkyl or an acetyl group, and more preferably a hydrogen atom, a methyl group or an ethyl group. Both Gia and G2a are preferably oxygen atoms. X ^ is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom or a fluorine atom. X2a is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom. X3a and X4a are preferably hydrogen atoms. Y is preferably a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoro-n-propylthio group, a heptafluoro-i-propylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a heptafluoro-n-propylsulfinyl group, a heptafluoro-i- group propylsulfinyl, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a heptafluoro-n-propylsulfonyl group, a heptafluoro-i-propylsulfonyl group, a methoxy group, an ethoxy group, a trifluoromethoxy group, a pentafluoroethoxy group, a 2-fluoroethoxy group, a group 2,2-difluoroethoxy, a 2,2,2-trifluoroethoxy group or a 2,2,2-trichloroethoxy group, and more preferably a trifluoromethylthio group, a pentafluoroethylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a trifluoromethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group or a 2,2,2-trifluoroethoxy group. Y2a and Y4a are preferably a hydrogen atom, a halogen atom, a methyl group, and more preferably a hydrogen atom. Y5a is preferably a fluorine atom, an atom of chlorine, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a trifluoromethyl group, a group methylthio, a methylisulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoro-i-propylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a heptafluoro-n-propylsulfinyl group, a heptafluoro-i-propylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a heptafluoro-n-propylsulfonyl group, a heptafluoro-i-propylsulfonyl group, a cyano group, a methoxy group, an ethoxy group, an n-propyloxy group, a trifluoromethoxy group, a pentafluoroethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group or a 2,2,2-trichloroethoxy group. Ra and Rb are each preferably a fluorine atom, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoro-n-propyl group, and more preferably a fluorine atom, a trifluoromethyl group or a pentafluoroethyl group. Rc is preferably a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, an ethoxy group, a methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a phenylsulfonyloxy group, a p-toluenesulfonyloxy group, a group acetoxy or a trifluoroacetoxy group, more preferably a hydroxy group, a chlorine atom, a bromine atom, a methoxy group, a methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a phenylsulfonyloxy group or a p-toluenesulfonyloxy group, and more preferably a hydroxy group, a chlorine atom or a bromine atom. Rc 'is preferably a hydroxy group. Rc "is preferably a chlorine atom or a bromine atom J and J 'are each preferably a hydroxy group, a chlorine atom or a bromine atom, and more preferably a chlorine atom.
The compounds of the present invention represented by the general formula (1) may contain the following compounds from I to V. (Compound I) Compound I is represented by the general formula (1a) wherein A ,, A2l A3 and A4 in the general formula (1) they are all carbon atoms, wherein, in formula (1a), when any of Ri and R2 is a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both R ^ and R2 are C1-C4 groups alkyl or C1-C4 alkylcarbonyl groups; Gi and G2 are each independently an oxygen atom or a sulfur atom; Xi, X2, X3 and X are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; Q1 is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a group C1-C3 haloalkoxy, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group , a C 1 -C 4 alkylamino group, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, a group C1-C4 alkoxycarbonyl, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a N-oxide pyridine group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group ), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2- group) C4 alkenyl, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 group haloalkoxy, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a group C1-C4 alkylamino, a C1-C4 di alkylamino group, a group or cyano, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group) (The heterocyclic group represents the same as those described previously.); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, Y ^ represents a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5 represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 pentafluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 each independently represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group, or wherein, in the formula, Y6 and Yg each independently represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1 group -C3 alkylthio, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 group haloalkylsulfinyl, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Ye and Yg must represent a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a group C1-C3 haloalkylsulfonyl.). As the compound I represented by the general formula (1a), a compound containing the following group can be used, wherein, in the formula (1a), Q2 is represented by the general formula (2), wherein, in the formula, YT represents a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5 represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. In addition, as the compound I represented by the general formula (1a), a compound containing the following group can be used, wherein, in the general formula (1a), Q2 represents the aforementioned group, Qi represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a group C2-C4 alkenyl, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1 group -C3 haloalkoxy, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 di alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 group alkylcarbonyloxy, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a group C2-C4 alkenyl, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1 group -C3 haloalkoxy, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C 1 -C 4 alkylamino group, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group, a group acetylamino and a phenyl group). (Compound II) Compound II is represented by the general formula (1a) where A ,, A2, A3 and A in the general formula (1) are all carbon atoms, wherein, in formula (1a), RT and R2 are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group; G, and G2 are each independently an oxygen atom or a sulfur atom; Xi, X2, X3 and X4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; QT is a substituted phenyl group having one or more substituents which may be the same or different (substituents selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group , a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, or a C1 group -C4 alkylamino, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1- C4 alkoxycarbonyl, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group of the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a group furyl, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group.), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl, a C2-C4 alkenyl group, C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a group C1-C3 alkylthio, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1- C4 alkylamino di, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy, C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group) (The heterocyclic group represents the same or those described previously.); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, Yi represents a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5 represents a halogen atom, a C1 C4-alkyl, a C1-C4 haloalkyl, a C1-C4 alkoxy group, C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group, or wherein, in the formula, Y6 and Yg each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a group cyano; Y8 represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Ye and Yg should represent a C1-C3 haloalkylthio group, a C1-C3 group haloalkylsulfinyl or a group C1-C3 haloalkylsulfonyl.). As the compound II represented by the general formula (1a), a compound containing a follow-up group can be used, wherein, in the formula (1a), Qi represents a substituted phenyl group having one or more substituents which can be the same or different (the substituents selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a group C1-C3 alkylsulfinyl, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1- C3 haloalkylsulfonyl, an amino group, a C1-C4 alkylamino group, a C1-C4 di alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a group C1-C4 alkoxycarbonyl, an acetylamino group and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a group C2-C4 alkenyl, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1 group -C3 haloalkoxy, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a group C 1 -C 4 alkylamino, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group, an acetylamino group and a phenyl group); and Q2 is represented by the general formula (2), (2) wherein, in the formula, Yi represents a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5 represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. (Compound III) Compound III is represented by the general formula (1a) where AL A2, A3 and A4 in the general formula (1) are all carbon atoms, wherein, in the formula, RT and R2 are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group; Gi and G2 are each independently an oxygen atom or a sulfur atom; Xi, X2, X3 and X are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; QT is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a group C1-C3 haloalkoxy, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group , a C 1 -C 4 alkylamino group, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group, a acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present inv tion represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a group thiazolyl, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group.), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 di alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group , a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group) (The heterocyclic group represents the same or those described above.); and Q2 is represented by the general formula (2) or (3), (2) wherein, in the formula, Y, represents a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5 represents a fluorine atom, a chlorine atom, an iodine atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 group alkylthio, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group, or wherein, in the formula, Y6 and Y9 each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1 group -C3 alkylthio, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a group C1-C6 perfluoroalkylthio, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Yg must represent a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a group C1-C3 haloalkylsulfonyl.). As the compound III represented by the general formula (1a), a compound containing a follow-up group can be used, wherein, in the formula (1a), Qi represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a group C2-C4 alkynyl, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1 group -C3 haloalkylthio, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 alkylamino group , a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a Group C1-C4 alkylcarbonyloxy, a group C1- C4 alkoxycarbonyl, an acetylamino group and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1 group- C4 alkyl, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 group halocycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group , a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 di alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1- C4 alkylcarbonyloxy, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group); and Q2 is represented by the general formula (2), wherein, in the formula, YT represents a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5 represents a fluorine atom, a chlorine atom, an iodine atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group , a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. (Compound IV) Compound IV is represented by the general formula (1a) wherein A ^ A2, A3 and A in the general formula (1) are all carbon atoms, wherein, in the formula, Ri and R2 are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group; GT and G2 are each independently an oxygen atom or a sulfur atom; ? > X2, 3 and X4 are each independently an atom of hydrogen, a halogen atom or a trifluoromethyl group; Qi is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or difnt (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a group C1-C3 haloalkoxy, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group , a C1-C4 alkylamino group, a C1-C4 di alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention tion represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group.), or a substituted heterocyclic group having one or more substituents which may be the same or difnt (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 group alkylamino, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group ) (The heterocyclic group represents the same or those described above.); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, YT represents a C2-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5 represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a group C1-C3 haloalkylsulfinyl, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Y6 and Yg each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1 group -C3 alkylthio, a C2-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a group C1-C4 haloalkoxy, a C2-C6 perfluoroalkyl group, a group C1-C6 perfluoroalkylthio, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Yg they must represent a C2-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group.). As the compound IV represented by the general formula (1a), a compound containing a follow-up group can be used, wherein, in the formula (1a), Qi represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a group C2-C4 alkenyl, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1 group -C3 haloalkoxy, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a group C 1 -C 4 alkylamino, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2- group C4 haloalkynyl, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 group alkylsulfinyl, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group); and Q2 is represented by the general formula (2), wherein, in the formula, Yi represents a C2-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a C 1 -C 3 haloalkylthio group, a group C1-C3 alkylsulfinyl, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. (Compound V) Compound V is represented by the general formula (D. wherein Ai, A2, A3 and A4 each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom; when any of Ri and R2 is a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both of RT and R2 are C1-C4 alkyl groups or C1-C4 alkylcarbonyl groups; Gi and G2 are each independently an oxygen atom or a sulfur atom; Xs are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; n represents an integer from 0 to 4; Qi is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom), a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 di alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group , a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a group pyrimidinyl, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, a group is oxazolyl, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group.), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a group C2-C4 alkynyl, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1 group -C3 haloalkylthio, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 alkylamino group , a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group) (The heterocyclic group represents the same or those described above.); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, YT represents a C1-C4 alkoxy group or a C1-C4 haloalkoxy group; Y5 represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a group C1-C3 alkylsulfinyl, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group, or wherein, in the formula, Y6 and Yg each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1 group -C3 alkylthio, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Yg must represent a C1-C4 alkoxy group or a C1-C4 haloalkoxy group.).
As the compound V represented by the general formula (1), the compound represented by the general formula (1a) in which A2, A3 and A4 in the general formula (1) are all carbon atoms can be used, wherein, in the formula, when either Ri and R2 are a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both RT and R2 are C1-C4 alkyl groups or C1 groups -C4 alkylcarbonyl; GT and G2 are each independently an oxygen atom or a sulfur atom; X, X2, X3 and X4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; Qi is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a group C1-C3 haloalkoxy, a C1-C3 alkylthio group, a C1-C3 group haloalkylthio, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 group di alkylamino, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a group pyrimidinyl, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group.), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1 group -C4 haloalkyl, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1- C3 alkoxy, a gr upo C1-C3 haloalkoxy, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 di alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 group alkylcarbonyloxy, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group) (The heterocyclic group represents the same or those described above.); and Q2 is represented by the general formula (2), wherein, in the formula, Yi represents a C1-C4 haloalkoxy group; Y5 represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. As the compound V represented by the general formula (1a), a compound containing a follow-up group may be used, wherein, in formula (1a), Qi represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2- group C4 haloalkynyl, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 group alkylsulfinyl, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbon group ilo, an acetylamino group and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 group alkyl, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 group alkynyl, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group , a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 di alkylamino group, a group cyano, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group). Typical preparation methods of the compounds of the present invention are illustrated below. The compound of the present invention can be prepared according to the methods, although the trajectories of the preparation method are not restricted to the following preparation methods. In the following methods of preparation, Q2a is any of the general formula (2), (3) and (5), where, in the formula, Y ,, Y2, Y3, Y4 and Y5 represent the same as those described in [1], where, in the formula, Y6, Y, Y8 and Y9 represent the same or those described in [1], and where, in the formula, Y ^, Y2a, Y4a, Ysa, Ra, Rb and Rc represent the same as those described in [15]. In addition, Q2b is represented by the general formula (5), in the process for producing the compounds of the present invention. Method of Preparation 1 where, in the formula, Ai, A2, A3, A4, G G2, R1 (R2, X, n and Q1 represent the same as those described in [1]; represents a functional group having the ability of a starting group such as a halogen atom, a hydroxy group or the like. 1- (i): General formula (19) + General formula (20)? General Formula (21) By reacting a m-nitroaromatic carboxylic acid derivative having a starting group represented by the general formula (19) with an aromatic amine derivative represented by the general formula (20) in a suitable solvent or without a solvent, an aromatic carboxamide derivative having a nitro group represented by the general formula (21) can be prepared. In the process, you can also use a suitable base. Solvents may not noticeably hinder the progress of the reaction and examples thereof include water; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like; chain ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methyl isobutyl ketone, cyclohexanone and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile and Similar; 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethyl sulfoxide and the like. These solvents can be used alone or in combination of 2 or more types. In addition, examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, 4-dimethylaminopyridine and the like; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium hydrogen carbonate, potassium carbonate and the like; phosphates such as di-potassium monohydrogen phosphate, tri-sodium phosphate and the like; alkali metal hydrides such as sodium hydride and the like; and alkali metal alcoholates such as sodium methoxide, sodium ethoxide and the like. These bases can be suitably selected within the range of 0.01 to 50 mol equivalents based on the compound represented by the general formula (19) and used accordingly. The reaction temperature can be suitably selected within the range of -20 ° C to the reflux temperature of a solvent in use, while the reaction time can be appropriately selected within the range of several minutes to 96 minutes. hours. In the compounds represented by the general formula (19), an aromatic carboxylic acid halide derivative can be easily prepared from an aromatic carboxylic acid according to a usual method using a halogenation agent. Examples of the halogenating agent include thionyl chloride, thionyl bromide, phosphorous oxychloride, oxalyl chloride, phosphorous trichloride, phosphene and the like. On the other hand, the compound represented by the general formula (21), can be prepared from the m-nitroaromatic carboxylic acid wherein L in the general formula (19), represents a hydroxy group and a compound represented by the general formula ( 20) without using a halogenating agent. As a method thereof, an additive such as 1-hydroxybenzotriazole and the like can be suitably used, according to one method, as described, for example, in the Chem. Ver. P. 788 (1970) publication. , and a method employing a condensing agent utilizing N, N'-dicyclohexylcarbodiimide can be exemplified. Other condensing agents that will be used in this case include, for example, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 1,1'-carbonylbis-1 H-imidazole and the like. In addition, as another process for preparing the compound represented by the general formula (21), a mixed anhydride process using chloroformates can be mentioned. Also, the compound represented by the general formula (21) can be prepared according to a method as described in the publication of J. Am. Chem. Soc. P. 5012 (1967). The examples of chloroformates to be used in this case include isobutyl chloroformate, isopropyl chloroformate and the like. In addition to the chloroformates, there can be mentioned diethyl chloride, trimethylacetyl chloride and the like. Both the methods using a condensing agent and a mixed anhydride process are not restricted to the solvent, reaction temperature and reaction time described in the above literatures, and an inert solvent that does not noticeably impede proper progress can be used. of the reaction. The reaction temperature and reaction time can be selected appropriately as the reaction proceeds. 1- (ii): General formula (21)? General Formula (22) An aromatic carboxamide derivative having a nitro group represented by the general formula (21) can be prepared in an aromatic carboxamide derivative having an amino group represented by the general formula (22) through the reduction reaction. As the reduction reaction, there can be mentioned a method employing hydrogenation and a method employing a metal compound (for example, tin (II) chloride (anhydride), iron powder, zinc powder and the like). The first method can be carried out in a suitable solvent in the presence of a catalyst, at atmospheric pressure or under increased pressure, in an atmosphere of hydrogen. The catalyst includes, for example, palladium catalysts such as palladium carbon and the like, nickel catalysts such as Raney nickel and the like, platinum catalysts, cobalt catalysts, ruthenium catalysts, rhodium catalysts and the like. Solvents include, for example, water; alcohols such as methanol ethanol and the like; aromatic hydrocarbons such as benzene, toluene and the like; chain ethers or cyclic ethers such as ether, dioxane, tetrahydrofuran and the like; and esters such as ethyl acetate and the like. The pressure can be appropriately selected within the range of 0.1 to 10 MPa, the reaction temperature can be appropriately selected within the range of -20 ° C to the reflux temperature of a solvent in use, and the time of The reaction can be selected appropriately within the range of several minutes up to 96 hours. Subsequently, the compound of the general formula (22) can be prepared more effectively. As the latter method, there can be mentioned a method employing tin (II) chloride (anhydride) in the form of a metal compound according to the conditions described in the publication of "Organic Syntheses" Coll. Vol. Ill P. 453. 1- (iii): General Formula (22) + General Formula (23)? General formula (24) By reacting an aromatic carboxamide derivative having an amino group represented by the general formula (22) with a compound represented by the general formula (23) in a suitable solvent or without a solvent, a compound represented by the general formula (24) of the present invention. In this process, a suitable base can also be used. The solvents may not markedly hinder the progress of the reaction in the examples thereof may include; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like, chain ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methyl isobutyl ketone, cyclohexanone and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile and the like; and inert solvents such as 1,3-dimethyl-2-imidazolidinone and the like. These solvents can be used alone or in combination of 2 or more types. In addition, examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, 4-dimethylaminopyridine and the like; alkali metal hydroxides such such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium hydrogen carbonate, potassium carbonate and the like; phosphates such as mono-hydrogen di-potassium phosphate, tri-sodium phosphate and the like; alkali metal hydrides such as sodium hydride and the like, and alkali metal alcoholates such as sodium methoxide, sodium ethoxide and the like. These bases can be selected in an appropriate manner between the ranges of 0.01 to 50 mol equivalents based on the compound represented by the general formula (22) and used accordingly. The reaction temperature can be suitably selected within the range of -20 ° C to the reflux temperature in a solvent in use, while the reaction time can be appropriately selected within the range of several minutes to 96 minutes. hours. In addition, a method employing a condensing agent as described in 1- (i) or a mixed anhydride process can also be used. 1 - (iv): General Formula (24) + General Formula (25) -? General Formula (26) By reacting a compound represented by the general formula (24), an alkyl compound having a starting group represented by the general formula (25) in a solvent without a solvent, a compound represented by the general formula (26). The examples of The compound represented by the general formula (25) include metal halides such as methyl iodide, ethyl iodide, n-propyl bromide and the like. In addition, in this process, a suitable solvent base can be used. As the base or solvent, the bases or solvents mentioned in 1- (i) can be used. The reaction temperature and reaction time mentioned in 1- (i) can be used. In addition, the compound represented by the general formula (26) can also be prepared by the alternative method which comprises reacting an alkylating agent, such as dimethyl sulfate, diethyl sulfate or the like, instead of the compound represented by the formula general (25), with the compound represented by the general formula (24). Preparation Method 2 where, in the formula, A ,, A2, A3, A ld, G2) R ,, R2, X, n and Qi represent the same as those described in [1], L represents a functional group that has the capacity of a starting group such as a halogen atom, a hydroxyl group or Similar; and Hal represents a chlorine atom or a bromine atom. 2- (i): General Formula (27) + General Formula (23)? General Formula (28) By reacting a carboxylic acid having an amino group represented by the general formula (27) with a compound represented by the general formula (23), according to the conditions of suitable selection of a solvent and base respectively as described in 1- (i) or without a solvent or base, a carboxylic acid having an acylamino group represented by the general formula (28) can be prepared. The reaction time and reaction temperature can be appropriately selected from the conditions described in 1- (i). 2- (ii): General Formula (28)? General Formula (29) A compound represented by the general formula (29) can be prepared through a known halogenation reaction which comprises reacting a compound represented by the general formula (28) with thionyl chloride, oxalyl chloride, phosgene , phosphorous oxychloride, phosphorous pentachloride, phosphorous trichloride, thionyl bromide, phosphorous tribromide, diethylaminosulfur trifluoride or the like. 2- (iii): General Formula (29) + General Formula (20)? General Formula (30) By reacting a compound represented by the general formula (29) with a compound represented by the general formula (20) according to the appropriate selection conditions of a solvent and a base, respectively, as described in 1- (i) or without a solvent or without a base, a compound represented by the general formula (30) can be prepared. The reaction time and reaction temperature can be suitably selected from the conditions described in 1- (i). 2- (iv): General Formula (28) + General Formula (20)? General Formula (30) Reacting a compound represented by the general formula (28) with a compound represented by the general formula (20) according to the conditions using a condensing agent or a mixed anhydride process as described in 1- (i), a compound represented by the general formula (30) can be prepared. Preparation Method 3 (48) (49) where, in the formula, Ai, A2, A3, A4, X, n, G2 and R2 represent the same as those described in [1]. By reacting a compound represented by the general formula (48) with a suitable reagent in a suitable solvent or without a solvent, using a suitable base, a compound represented by the general formula (49) can be prepared. Solvents may not noticeably hinder the progress of the reaction in examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methyl isobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethisulfoxide, water and the like. These solvents can be used alone or in combination of 2 or more types. Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, 4-dimethylaminopyridine and the like; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium hydrogen carbonate, potassium carbonate and the like; phosphates such as monohydrogen potassium phosphates, tri-sodium phosphate and the like; alkali metal hydrides such as sodium hydride and the like; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and the like; organolithiums such as n-butyl lithium and the like; and Gringnard reagents such as ethylmagnesium bromide and the like. These bases can be selected in an appropriate manner between the ranges of 0.01 to 50 mol equivalents based on a compound represented by the general formula (48). Examples of the reagent include halogenated alkyls such as methyl iodide, ethyl bromide, trifluoromethyl iodide, 2,2,2-trifluoroethyl iodide, and the like; and halogenated such as allyl iodide and the like; halogenated propargyl such as propargyl bromide and the like; halogenated acyls such as acetyl chloride and the like; acid anhydrides such as trifluoroacetic anhydride and the like; alkyl sulfuric acid such as dimethyl sulfate, diethyl sulfate and the like. These reagents can be suitably selected from the range of 1 to 5 mol equivalents, based on the compound represented by the general formula (48) or can be used as a solvent. The reaction temperature can be selected appropriately between the range of -80 ° C to the temperature of reflux of a solvent in use, while the reaction time can be selected appropriately between the range of several minutes up to 96 hours. Preparation Method 4 where, in the formula, AL A2, A3, A4, X, n, G2, Ri and R2 represent the same as those described in [1]. 4- (i): General Formula (22)? General Formula (50) By reacting a compound represented by the general formula (22) with aldehydes or ketones in a suitable solvent or without a solvent, adding a suitable catalyst and reacting the result in a hydrogen atmosphere, a compound represented by the general formula (50). The solvents may not noticeably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methyl isobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethisulfoxide, methanol, ethanol and the like; water and the like. These solvents can be used alone or in combination of 2 or more types. Examples of the catalyst include palladium catalysts such as palladium carbon and the like; nickel catalysts such as Raney nickel and the like; cobalt catalysts, platinum catalysts, ruthenium catalysts, rhodium catalysts and the like. Examples of aldehydes include formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, bromoacetaldehyde and the like. Examples of ketones include acetone, perfluoroacetone, methylethyl ketone and the like. The reaction pressure can be selected appropriately within the range of 0.1 MPa to 10 MPa. The reaction temperature can be selected appropriately within the range of -20 ° C to the temperature of reflux of a solvent in use, while the reaction time can be selected appropriately within the range of several minutes up to 96 hours. 4- (ii): General Formula (22)? General Formula (50) (Alternative Method 1) By reacting a compound represented by the general formula (22) with aldehydes or ketones in a suitable solvent without a solvent, and applying a suitable reducing agent, the compound represented by the general formula (50). Solvents may not noticeably hinder the progress of the reaction and reaction examples are not included of aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methyl isobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethyl sulfoxide, methanol, ethanol and Similar; water and the like. These solvents can be used alone or in combination of 2 or more types. Examples of the reducing agent include borohydrides such as sodium borohydride, sodium cyanoborohydride, sodium triacetate borohydride and the like. Examples of aldehydes include formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, bromoacetaldehyde and the like. Examples of ketones include acetone, perfluoroacetone, methylethyl ketone and the like. The reaction temperature can be suitably selected within the range of -20 ° C to the reflux temperature of a solvent in use, while the reaction time can be appropriately selected within the range of several minutes to 96 minutes. hours. 4- (iii): General Formula (22)? General Formula (50) (Alternative Method 2) By reacting a compound represented by the general formula (22) with a formylating agent in a suitable solvent without a solvent and adding a suitable additive thereto, it is possible to prepare a compound, wherein , in the general formula (50), R1 is a methyl group. Solvents may not hinder significantly the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methyl isobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethisulfoxide, methanol, ethanol and the like; water and the like. These solvents can be used alone or in combination of 2 or more types. Examples of the formylating agent include anhydrous formic acids such as formaldehyde, formic acid, fluoroformic acid, formyl (2,2-dimethylpropionic acid) and the like; formic acid esters such as phenyl formate and the like; pentafluorobenzaldehyde, oxazole and the like. Examples of the additive include inorganic acids such as sulfuric acid and the like; organic acids such as formic acid and the like; borohydrides such as sodium borohydride, sodium cyanoborohydride and the like; acids boronic, lithium aluminum hydride and the like. The reaction temperature can be suitably selected within the range of -20 ° C to the reflux temperature of a solvent in use, while the reaction time can be appropriately selected within the range of several minutes to 96 minutes. hours. Preparation Method 5 where, in the formula, R2, Y2, Y3, Y and Y5 represent the same as those described in [1]; m represents 1 or 2; and Rf represents a haloalkyl group of C 1 -C 3. By using a suitable oxidant, a compound represented by the general formula can be prepared from a compound represented by the general formula. For example, a method described in the Tetrahedron Lett Publication may be mentioned. p. 4955, (1994). Examples of the oxidant include organic peroxides such as m-chloroperbenzoic acid and the like, sodium metaperiodate, hydrogen peroxide, ozone, selenium dioxide, chromic acid, dinitrogen tetraoxide, acyl nitrate, iodine, bromine, N-bromosuccinimide, iodosylbenzyl , t-butyl hypochlorite and the like. The oxidant can be selected in the suitable within the range of 1 to 5 mol equivalents, based on the compound represented by the general formula. A suitable additive can be added and examples thereof include ruthenium chloride (III) and the like. The solvent used in the process does not restue to the solvents described in the above literatures and may not significantly hinder the progress of the reaction. These solvents can be used alone or in combination of 2 or more types. The reaction temperature can be suitably selected within the range of -20 ° C of the reflux temperature in a solvent in use, while the reaction time can be appropriately selected within the range of several minutes up to 96 minutes. hours. Preparation example 6 wherein, in the formula, E represents a nitro group, an amino group, a group -NH-Ri or a group -N (R?) -C (= G1) Q ?; A1t A2, A3, A4, X, n, Y2, Y3, Y, Y5, R-i, Gi and Q represent the same as those described in [1]; m represents 1 or 2; and Rf represents a haloalkyl group of C 1 -C 3. By using a suitable oxidant, a compound represented by the general formula from a compound represented by the general formula. The compound represented by the general formula can be prepared according to the conditions described in Preparation Method 5 using a compound represented by the general formula, as a starting raw material. Preparation Method 7 (14) (13) wherein, in the formula, E represents a nitro group, an amino group, a group -NH-RT OR a group -N (R1) -C (= G1) Q1; Ai, A2, A3, A, X, n, RL d and Qi represent the same as those described in [1]; and Y a, Y2a, Y4a, Y5a, Ra, R, Rc 'and Rc "represent the same as those described in [23]. By reacting a compound represented by the general formula (51) with a suitable halogenating agent in a suitable solvent without a solvent, a chlorine compound (a bromine compound or an iodine compound) represented by the general formula (52) can be prepared In the process, a suitable additive can also be used. hampering in a remarkable way the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methyl isobutyl ketone, cyclohexanone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethisulfoxide, methanol, ethanol and the like; and solvents such as water and the like. These solvents can be used alone or in combination of 2 or more types. Examples of the halogenating agent include thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, phosphorous trichloride, phosphorous tribromide, phosphorous pentachloride, Rydon reagents, sulfonyl halides such as methanesulfonyl chloride, p-toluenesulfonyl chloride, chloride of benzenesulfonyl and the like; sulfonium halides, sulfonate esters, chlorine, bromine, iodine, hypohalite esters, N-halogenamines, hydrogen chloride, hydrogen bromide, sodium bromide, potassium bromide, cyanuric chloride, 1,3-dichloro-1,2. , 4-triazole, titanium chloride (IV), vanadium chloride (IV), arsenic chloride (III), N, N, -d-ethyl-1, 2,2- trichlorovinylamine, trichloroacetonitrile, sodium chloride, ammonium bromide, N, N-dimethylchloroforminium chloride, N, N-dimethylchloroforminium bromide, phosphorous trichloride, phosphorous tribromide, N-dimethyl phosphoamidine dichloride and the like. Examples of the additives include metal salts such as zinc chloride, lithium bromide and the like; organic bases such as phase transfer catalysts, hexamethylphosphoric triamide and the like; inorganic acids such as sulfuric acid and the like; N. N-dimethylformamide and the like. The halogenating agent can be suitably selected within the range of 0.01 to 10 mole equivalent, based on the compound represented by the general formula (51), it can be used as a solvent. The reaction temperature can be suitably selected within the range of -80 ° C to the reflux temperature in a solvent in use, while the reaction time can be appropriately selected within the range of several minutes to 96 minutes. hours. Preparation Method 8 (53) (54) where, in the formula, E represents a nitro group, a amino group, a group -NH-RÍ OR a group -N (R1) -C (= G1) Q ?; A1 F A2, A3, A, X, n, Ri, GT and QT represent the same as those described in [1]; and Y-ia, Y2a, Y4a, Y5a, Ra, Rb and Rc represent the same as those described in [15]. By reacting a compound represented by the general formula (53) with a suitable fluorinating agent in a suitable solvent without a solvent, a compound represented by the general formula (54) can be prepared. The solvents may not significantly impair the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like.; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methyl isobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethisulfoxide, methanol, ethanol and the like; and solvents such as water and the like. These solvents can be used alone or in combination of 2 or more types.
Examples of the fluorinating agent include 1,1,2,2-tetrafluoroethyldiethylamine, 2-chloro-1,1,2-trifluoroethyldiethylamine, trifluorodiphenylphosphorane, difluorotriphenylphosphorane, fluoroformate esters, sulfur tetrafluoride, potassium fluoride, potassium hydrogen fluoride , cesium fluoride, rubidium fluoride, sodium fluoride, lithium fluoride, antimony fluoride (III), antimony fluoride (V), zinc fluoride, cobalt fluoride, lead fluoride, copper fluoride, mercury fluoride (II), silver fluoride, silver nitrate fluoride, thallium fluoride (I), molybdenum fluoride (VI), arsenic fluoride (III), bromine fluoride, selenium tetrafluoride, tris (dimethylamino) sulfonium difluorotrimethylsilicate , sodium hexafluorosilicate, quaternary ammonium fluoride, (2-chloroethyl) diethylamine, diethylaminosulfur trifluoride, morpholino-sulfur trifluoride, silicone t-fluoride, hydrogen fluoride, hydrofluoric acid, pyridine complex of hydrogen fluoride, triethylamine complex of hydrogen fluoride, hydrogen fluoride salt, bis (2-methoxyethyl) aminoasulfur trifluoride, 2,2-difluoro-1,3-dimethyl-2-imidazolidinone, iodine pentafluoride, hyalide of tris (diethylamino) phosphonium-2,2,3,3,4,4-hexafluoro-cyclobutane, triethylammonium ylides hexafluorocyclobutane, hexafluoropropane and the like. These fluorinating agents can be used alone or in combination of 2 or more types. These fluorinating agents can be suitably selected from among the ranges from 1 to 10 mol equivalents, based on the compounds represented by the general formula (53) and can be used appropriately as a solvent. An additive can also be used and examples thereof include crown ethers such as 18-crown-6 and the like; phase transfer catalysts such as tetraphenylphosphonium salts and the like; inorganic salts such as calcium fluoride, calcium chloride and the like; metal oxides such as mercury oxide and the like; ion exchange resins and the like. These additives may not be added during the reaction and may only be used as pre-treatment agents for fluorinating agents. The reaction temperature can be suitably selected within the range of -80 ° C to the reflux temperature of a solvent in use, while the reaction time can be suitably selected within the range of several minutes to 96 minutes. hours. Typical compounds of the compound which is an active ingredient of an insecticide of the present invention are illustrated in Tables 1 to 6 below, although the present invention is not restricted thereto. Incidentally, in the tables, "n" refers to normal, "Me" refers to a methyl group, "Et" refers to an ethyl group, "n-Pr" refers to a normal propyl group, "i-" Pr "refers to an isopropyl group," n-Bu "refers to a butyl group normal, "i-Bu" refers to an isobutyl group, "s-Bu" refers to a secondary butyl group, "t-Bu" refers to a tertiary butyl group, "H" refers to a hydrogen atom , "O" refers to an oxygen atom, "S" refers to a sulfur atom, "C" refers to a carbon atom, "N" refers to a nitrogen atom, "F" refers to a to a fluorine atom, "Cl" refers to a chlorine atom, "Br" refers to a bromine atom, "I" refers to an iodine atom, "CF3" refers to a trifluoromethyl group, " C2F5"refers to a pentafluoroethyl group," n-C3F7"refers to a heptafluoro-n-propyl group," i-C3F7"refers to a heptafluoro-i-propyl group," 2-C Fg "refers to a nonofluoro-2-butyl group, "SCF3" refers to a trifluoromethylthio group, "SC2F5" refers to a pentafluoroethylthio group, "Sn-C3F7" refers to a heptafluoro-n-propylthio group, "S (O) CF3"refers to a trifluoromethylsulfinyl group," S (O) C2F5"refers to a pentaflu group oroethylsulfinyl, "S (O) -n-C3F7" refers to a heptafluoro-n-propylsulfinyl group, "SO2CF3" refers to a trifluoromethylsulfonyl group, "SO2C2F5" refers to a pentafluorethylsulfonyl group, "SO2-n-C3F7" is refers to a heptafluoro-n-propylsulfonyl group, "OMe" refers to a methoxy group, "OEt" refers to an ethoxy group, "OCF3" refers to a trifluoromethoxy group, "OCH2CF3" refers to a group 2, 2,2-trifluoroethoxy, "OCH (CF3) 2" refers to a 1,1,1,3,3-hexafluoro-2-propyloxy group, and "Ac" refers to an acetyl group.
General formula (A) Table 1-2 Table 1-3 Table 1-4 Table 1-5 Table 1-6 Table 1-7 General Formula (A) Table 2-1 Table 2-2 Table 2-3 Table 2-4 Table 2-5 Table 2-6 Table 2-7 General Formula (A) Table 3-1 Table 3-2 General Formula (B) Table 4-1 General Formula (C) Table 5-1 Table 5-2 General Formula (D) Table 6-2 The physical properties of the compound of the present invention are shown in Table 7 below. Tetramethylsilane was used as an internal standard substance to record the 1 H-NMR change values as shown in the present invention, unless otherwise specifically mentioned.
Table 7-1 Table 7-2 Table 7-3 Table 7-4 Table 7-5 Table 7-6 An insecticide comprising the compound represented by the general formula (1) of the present invention in the form of an active ingredient, is suitable for preventing insect pests such as various pests of agricultural insects, forest and horticultural insect pests, pest insects from barns, pests of hygienic insects, nematodes or the like which are harmful to paddy rice, fruit trees, vegetables, other crops, flowers and the like, and have a strong insecticidal effect, for example, in LEPIDOPTERA as cucumber moth (Diaphania indica), oriental tea tortrix moth (Homona magnanimous), cabbage net worm (Hellulla undalis), summer fruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes sp.), Apple tortrix (Archips fuscocopreanus), peach fruit moth (Carposina niponensis), Manchurian apple moth (Grapholita inopinata), oriental fruit moth (Grapholita molesta), bean pod bean (Leguminivora glycinivorella) ), blackberry tenuirrostra (Olethreutes morí), insect larva that lives inside the tissue of the bean pod leaf (Phyllocnistis citrella), persimo fruit moth (Stathmopoda masinissa), tea tenuirrostra (Caloptilia thevivora), larva of azalea insect (Caloptilia zachrysa), insect larva of apple insect (Phyllonorycter ringoniella), whitish insect pear sucker (Spulerrina astaurota), swallowtail butterfly (Papilio xuthus), common white (Piers rapae crucivora), caterpillar tobacco (Heliothis armígera), small apple moth (Lapsey resia pomonella), diamondback moth (Plutella xylostella), apple fruit moth (Argyresthia conjugella), moth peach fruit (Carposina niponensis), rice stemworm (Chilo suppressalis), rice tenuirrostra (Cnaphalocrocis medinalis), tobacco moth (Ephestia elutella), blackberry piralid (Glyphodes pyloalis), yellow rice worm (Scirpophaga incertulas) , rice hopper insects (Parnara guttata), rice moth worm (Pseudaletia separata), rose worm (Sesamia inferens), cabbage moth (Mamestra brassicae), common spotted larva (Spodoptera litura), beet moth worm ( Spodoptera exigua), larva of black fish (Agrotis Ípsilon), navo moth (Agrotis segetum), half-track (Autographa nigrisigna), caterpillar of cabbage (Trichoplusia ni) and the like; HEMIPTERA such as asterian tenuirrostra (Macrosteles fascifrons), green rice tenuirrostra (Nephotettix cincticeps), brown rice hopper insect (Nilaparvata lugens), small coffee hopper insect (Laodelphax striatellus), rice-leaping insect with white back (Sogatella furcifera) , citrus psylla (Diaphorina citri), whitish grape insect (Aleurolobus taonabae), whitish insect of belladonna (Bermisia argentifolii), whitish sweet potato insect (Bemisia tabaci), whitish greenhouse insect (Trialeurodes vaporariorum), turnip pulp (Lipaphis erysimi), cotton melon aphid (Aphis gossypií), spirea aphid (Aphis citricola), green peach aphid (Myzus persicae), Indian wax flake (Ceroplastes ceriferus), comstock flour insect (Pseudococcus comstocki), Japanese flour insect (Planococcus kraunhiae), cottony citrus flake (Pulvinaria aurantii), camphor flake (Pseudaonidia duplex), San Jose scale (Comstockaspis perniciosa), arrowhead scale (Unaspis yanonensis), insect green with brown wings (Plautia stali), insect stinking brown marbling (Halyomorpha mista) and similar; COLEOPTER such as bean bean (anomalous rufocuprea), Japanese beetle (Popillia japonica), tobacco beetle (Lasioderma) serricorne), dust beetle (Lyctus brunneus), coquito with twenty-eight spots (Epilachna vigintioctopunctata), adzuki bean weevil (Callosobruchus chinensis), vegetable weevil (Listroderes costirostris), corn weevil (Sitophilus zeamais), baga weevil (Anthonomus gradis gradis), rice water weevil (Lissorhoptrus oryzophilus), pumpkin leaf beetle (Aulacophora femoralis), rice leaf beetle (Oulema oryzae), grated flea beetle (Phyllotreta striolata), pine shoot beetle (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata), Mexican beetle (Epilachna varivestis), corn rootworm (Diabrotica sp.), Long-horned beetle with yellow spots (Psacothea hilaris), long-horned beetle with white spots (Anoplophora malasiaca) and the like; DIPPTER such as eastern fruit fly (Dacus (Bactrocera) dorsalis), rice insect larva (Agromyza oryzae), onion worm (Delia antiqua), corn seed worm (Delia platura), small pod mosquito soybeans (Asphondylia sp.), muscid fly (Musca domestica), insect larvae (Chromatomya horticola), serpentine insect larvae (Liriomyza trifolü), tomato insect larvae (Liriomyza bryoniae), domestic mosquito (Culex pipiens pipiens) and the like; TYLENCHIDA such as coffee root lesion nematode (Pratylenchus coffeae), nematode lesion (Pratylenchus sp.), Potato cyst nematode (Globodera rostochiensis), root button nematode (Meloidogyne sp.), citrus nematode (Tylenchulus semipenetrans), phage nematode (Aphelenchus avenae), chrysanthemum leaf nematode (Aphelenchoides ritzemabosi) and the like; THYSANOPTERA such as melon louse (Thrips palmi), western flower louse (Frankliniella occidentalis), yellow tea louse (Scitothrips dorsalis), yellow flower louse (Thrips flavus), onion louse (Thrips tabaci) and the like; and ORTHOPTERA such as German cockroach (Blatella germanica), American cockroach (Periplaneta americana), rice grasshopper (Oxya yezoensis) and the like. The insecticide comprising the compound represented by the general formula (1) of the present invention, as an active ingredient, has a remarkable control effect on insect pests exemplified above, which are detrimental to harvested rice fields. , upland crops, fruit trees, vegetables, other crops, flowers and the like. Accordingly, the desired effect as an insecticide of the present invention can be obtained by applying the insecticide to the rice field in the hull, upland, rice field water in the hull, stems and leaves of fruit trees, vegetables, other crops, flowers and similar, or land in a season in which insect pests are expected to appear, before their appearance or at the time their occurrence is confirmed.
The insecticide of the present invention is generally prepared in conveniently usable forms according to an ordinary form for the preparation of agricultural and horticultural chemicals. That is, the compound represented by the general formula (1), and optionally, an adjuvant can be combined with a suitable inert carrier in a suitable ratio and prepared in a suitable preparation form, such as a suspension, emulsifiable concentrate, soluble concentrate , moistened powder, granules, earth, tablets or the like through dissolution, separation, suspension, mixing, impregnation, absorption or adhesion. The inert carrier, which can be used in the present invention, can be either solid or liquid. Said material, which may be an inert solid carrier includes, for example, soy bean flour, cereal flour, wood flour, sorghum flour, striker powder, powdered tobacco hair, powdered walnut shells, wheat, cellulose. pulverized, vegetable extraction residues, synthetic polymers such as powdered synthetic resins, inorganic mineral powder such as clays (eg, kaolin, bentonite, acid clay and the like), talcs (eg, talc, prophyllite and the like), powders or silica flakes (for example, diatomaceous earth, silica sand, mica, white carbon [synthetic silicic acid, high dispersion, also called finely divided hydrated silicone, hydrated silicic acid, some commercially available products contain calcium silicate as the main component]), activated carbon, pulverized sulfur, pumice stone, calcined diatomite, brick chips, ash, sand, calcium carbonate powder, calcium phosphate powder and other inorganic mineral powders, chemical fertilizers (eg, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride and the like), compound and the like. These vehicles can be used alone or in combination of two or more types. A material that can be the inert liquid carrier is selected from a material which by itself has solvency or which has no such solvency but has a capacity to disperse an effective ingredient compound with the aid of an adjuvant. Below are typical examples of the conveyor and can be used alone or in combination of two or more types. Examples thereof include water, alcohols (e.g., methanol, ethanol, isopropanol, butanol, ethylene glycol, and the like), ketones (e.g., acetone, methylethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, and the like), ethers (e.g., diethyl ether, dioxane, cellosolve, diisopropyl ether, tetrahydrofuran and the like), aliphatic hydrocarbons (e.g., kerosene, mineral oil and the like) hydrocarbons aromatics (e.g., benzene, toluene, xylene, solvent naphtha, alkyl naphthalene and the like), halogenated hydrocarbons (e.g., dichloromethane, chloroform, carbon tetrachloride, chlorobenzene and the like), esters (e.g., ethyl acetate, acetate) butyl, ethyl propionate, isobutyl phthalate, dibutyl phthalate, dioctyl phthalate, and the like), amides (eg, dimethylformamide, diethylformamide, dimethylacetamide, and the like), nitriles (eg, acetonitrile, and the like). The following typical adjuvants can be exemplified.
These adjuvants can be used depending on the purposes and used alone or in combination of two or more types or it will not be necessary to use them in some cases. To emulsify, disperse, dissolve and / or wet a compound in the form of an active ingredient, a surfactant is used. Examples thereof include surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalenesulfonates, lignin sulphonates, esters of superior alcohol sulfate and the like. In addition, to stabilize the dispersion of a compound in the intake of an active ingredient, to adhere it and / or to bind it, the following adjuvants can be used. The examples of them include casein, gelatin, starch, methylcellulose, carboxymethylcellulose, Arabica gum, polyvinyl alcohols, pine oil, wheat oil, bentonite, Xantan gum, lignin sulphonates and the like. In order to improve the fluidity of a solid product, the following adjuvants can be used. Examples thereof include waxes, stearates, alkyl phosphates and the like. Adjuvants such as condensation products of naphthalenesulfonic acid, polycondensates of phosphates and the like, can be used as a peptizer for suspensible products. In the form of a foam removal agent, adjuvants such as silicone oil and the like can also be used. Incidentally, the compound represented by the general formula (1) of the present invention is stable to light, heat or oxidation and the like. However, an antioxidant or an ultraviolet absorber is added which includes a phenol derivative, for example, BHT (2,6-di-t-butyl-4-methylphenol) and BHA (butylated hydroxyanisole), a bisphenol or arylamin derivative. such as phenyl-a-naphthylamine, phenyl-β-naphthylamine, condensates of phenethidine and acetone and the like, or a benzophenone-based compound, in the form of a stabilizer in a suitable amount when necessary, during which it can be obtained a composition with very stabilized effect. The amount of the active ingredient of the compound represented by the general formula (1) of the present invention, is usually from 0.5% by weight to 20% by weight for powder formulations, from 5% by weight to 50% by weight for emulsifiable concentrates, from 10% by weight to 90% by weight for wettable powder, from 0.1% by weight to 20% by weight for granules and from 10% by weight to 90% by weight for flowable formulations. On the other hand, the amount of the vehicle in each formulation is usually from 60% by weight to 99% by weight for powder formulations, from 40% by weight to 95% by weight for emulsifiable concentrates, from 10% by weight to 90% by weight for wettable powder, from 80% by weight to 99% by weight for granules and from 10% by weight to 90% by weight for flowable formulations. In the meantime, the amount of the adjuvant is usually from 0.1% by weight to 20% by weight for powder formulations, from 1% by weight to 20% by weight for emulsifiable concentrates, from 0.1% by weight to 20% by weight for powder wettable, from 0.1% by weight to 20% by weight for granules and from 0.1% by weight to 20% by weight for flowable formulations. In order to control various types of insect pests, the compound of the present invention can be applied appropriately to crops that are expected to create insect pests or places where such creation is not desired, and is applied in an effective amount. to control insect pests intact, it is diluted adequately with water or similar, or is suspended and used accordingly. The amount of it varies according to various factors such as the purpose, pests of target insects, status of harvested crops, tendency to emerge from insect pests, climate, environmental conditions, type of formulation, method of application, place of application, application time and the like. However, normally the amount is preferably at a concentration of 0.0001 ppm to 5000 ppm and preferably at a concentration of 0.01 ppm to 1000 ppm in the form of an active ingredient. In addition, the application amount is generally from 1 to 300 g per 10 acres as an active ingredient. The insecticide comprising the compound represented by the general formula (1) of the present invention in the form of an active ingredient, can be used only to prevent insect pests such as various pests of agricultural, forestry and horticultural insects, insect pests of barns, pests of hygienic insects, nematodes and the like which are harmful to rind in rice, fruit trees, vegetables, other crops, flowers and the like. Likewise, it can be used in combination of one or more types of other insecticides and / or fungicides in order to obtain a much greater control effect to control various diseases and pests of insects that occur at the same time. weather. When the compound represented by the general formula (1) of the present invention is used in combination with one or more other insecticides and / or fungicides, the compound represented by the general formula (1) can be used as a mixed solution with other insecticides and / or fungicides, or the compound represented by the general formula (1), can be used as a mixture with other insecticides and / or fungicides at the time of application of the agrochemicals. In addition, the compound represented by the general formula (1) can be used as a mixture with a plant protection agent such as a herbicide, a fertilizer, a soil conditioner, a plant growth regulator and the like, or a material, whereby a composition for multiple purposes can be prepared with an excellent effect, or a composition from which an additive effect or a synergistic effect can be expected. EXAMPLES Representative examples of the present invention will now be illustrated more specifically with reference to the following examples. However, the present invention is not restricted to these examples. Example 1-1 Preparation of 4-heptafluoro-isopropyl-2- (trifluoromethylthio) aniline 10.0 g of 2- (trifluoromethylthio) aniline, 45.8 g of 2-iodoheptafluoropropane, 10.8 g of sodium hydrosulfite, 5.2 g of sodium hydrogen carbonate and 2.01 of tetra-n-butylammonium hydrogensulfonate were added to a mixed solvent of 200 g. ml of t-butylmethyl ether and 200 ml of water, and the resulting mixture was stirred vigorously at room temperature for 10 hours. The organic phase was separated, washed with an aqueous solution of saturated sodium hydrogen carbonate, and then evaporated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 20: 1) to obtain 6.5 g of the title product (Yield: 35%) in the form of an orange oil. 1 H-NMR (CDCl 3, ppm) d 4.80 (2 H, broad-s), 6.84 (1 H, d, J = 8.3 Hz), 7.45 (1 H, d, J = 8.3 Hz), 7.70 (1 H, s). In the same method, the following anilines were prepared. 4-heptafluoro-isopropyl-2- (pentafluoroethylthio) aniline 1H-NMR (CDCl3, ppm) d 4.79 (2H, broad-s), 6.34 (1H, d, J = 8.8 Hz), 7.45 (1H, dd, J = 2.0 Hz and 8.8 Hz), 7.67 (1H, d, J = 2.0 Hz).
Orange oil 4-heptafluoro-isopropyl-2- (pentafluoro-n-propylthio) aniline 1 H-NMR (CDCl 3, ppm) d 4.78 (2 H, broad-s), 6.84 (1 H, d, J = 8.8 Hz), 7.46 (1 H, dd, J = 2.0 Hz and 8.8 Hz), 7.67 (1H, d, J = 2.0 Hz). Yellow oil 4- (heptafluoro-n-propyl) -2- (trifluoromethylthio) aniline 1 H-NMR (CDCl 3, ppm) d 4.20 (2H, broad-s), 6.85 (1H, d, J = 8.3 Hz), 7.44 (1H, dd, J = 2.0 Hz, 8.3 Hz), 7.69 (1H, d, J = 2.0 Hz). Yellow oil Example 1-2 Preparation of 2-bromo-4-heptafluoro-isopropyl-6- (trifluoromethylthio) aniline To a solution of 3.30 of 4-heptafluoro-isopropyl-2- (trifluoromethylthio) aniline added to 10 ml of N, N-dimethylformamide was introduced in the form of 1.62 drops of N-bromosuccinimide dissolved in 5 ml of N, N-dimethylformamide. . The reaction solution was stirred at room temperature for 2 hours, and then ethyl acetate and water were added. The organic phase was separated, washed with 50 ml of water, and then dried over anhydrous magnesium sulfate. He Anhydrous magnesium sulfate was filtered to obtain a solution and the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 15: 1) to obtain 2.92 g of the desired title product (yield: 73%) in the form of a light brown oil . 1 H-NMR (CDCl 3, ppm) d 5.29 (2 H, broad-s), 7.68 (1 H, s), 7.74 (1 H, d, J = 2.0 Hz). In the same method, the following anilines were prepared. 2-bromo-4-heptafluoroisopropyl-6- (pentafluoro-ethylthio) aniline 1 H-NMR (CDCl 3, ppm) d 5.28 (2 H, broad-s), 7.65 (1 H, s), 7.75 (1 H, d, J = 2.0 Hz). Orange oil 2-bromo-4- (heptafluoro-n-propyl) -6- (trifluoromethylthio) aniline 1 H-NMR (CDCl 3, ppm) d 5.36 (2 H, broad-s), 7.67 (1 H, s), 7.72 (1 H, d, J = 2.0 Hz). Orange oil In addition, using N-chlorosuccinic acid measurement in Instead of N-bromosuccinimide, 2-chloro-4-heptafluoroisopropyl-6- (trifluoromethylthio) aniline was prepared. 1 H-NMR (CDCl 3, ppm) d 5.23 (2 H, broad-s), 7.60 (1 H, s), 7.64 (1 H, s). Red oil Example 1 -3 Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3-nitrobenzamide 7.47 g of 3-nitrobenzoyl chloride and 7.56 g of 2-bromo-4-heptafluoroisopropyl-6- (trifluoromethylthio) aniline, 50 ml of pyridine were added, and the resulting mixture was stirred at a temperature of 90 ° C for 10 hours. . The reaction solution was poured into ice water and the pH value of the solution was adjusted to 1 by the addition of 2N hydrochloric acid. Subsequently, the reaction solution was extracted with ethyl acetate. The solvent was removed under reduced pressure to obtain a residue. The resulting residue was added to a mixed solvent of 30 ml of tetrahydrofuran and 20 ml of water, and the resulting mixture was stirred under an ice-water bath. To the solution was added 1.2 g of sodium hydroxide, and the result was stirred for 1.5 hours under an ice-water bath and subsequently stirred at room temperature for 20 hours. Ethyl acetate and water were added to the reaction solution to separate the organic phase. The organic phase was washed with saturated salt water once and dried over anhydrous magnesium sulfate and then the solvent was removed under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 6: 1) to obtain 6.85 g of the desired title product (Yield: 68%) as a white solid 1H -NMR (CDCl 3, ppm) d 7.80 (1H, t, J = 7.8 Hz), 8.05 (2H, s), 8.16 (1H, s), 8.30-8.34 (1H, m), 8.50-8.53 (1H, m ), 8.82 (1H, t, J = 2.0 Hz). Example 1-4 Preparation of 3-aminobenzamide N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl To a solution of 6.85 of 3-nitrobenzamide of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl and 7.61 g of tin (II) chloride (anhydride) added to 50 ml of ethanol were added to it. ml of concentrated hydrochloric acid, and the resulting mixture was stirred at a temperature of 60 ° C for 3 hours. The reaction solution was returned to room temperature, poured into ice water and neutralized with potassium carbonate. The insoluble substance was filtered and subsequently the solution was extracted with ethyl acetate, and the solvent was removed under reduced pressure. The precipitated residue was washed with n-hexane to obtain 5.13 g of the desired title product (yield: 79%) in the form of a white solid. 1 H-NMR (DMSO-d 6, ppm) d 5.40 (2H, broad-s), 6.78-6.81 (1H, m), 7.13-7.21 (3H, m), 7.99 (1H, s), 8.25 (1H, d) , J = 2.0 Hz), 10.64 (1H, s). In the same method, the following compounds were prepared. 3-aminobenzamide of N- (2-bromo-4-heptafluoroisopropyl-6-pentafluoro-ethylthio) phenyl H-NMR (CDCl 3, ppm) d 3.91 (2 H, broad-s), 6.91-6.94 (1 H, m), 7.25-7.34 (3 H, m), 8.01 (2 H, s), 8.06 (1 H, s). Solid white color 3-aminobenzamide of N- [2-bromo-4-heptafluoroisopropyl-6- (heptafluoro-n-propylthio)] phenyl 1 H-NMR (DMSO-de, ppm) d 5.40 (2H, broad-s), 6.80 (1H, d, J = 7.8 Hz), 7.14-7.22 (3H, m), 8.00 (1H, s), 8.29 ( 1H, s), 10.67 (1H, s). Solid white color 3-aminobenzamide of N- (2-chloro-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 1 H-NMR (CDCl 3, ppm) d 3.91 (2 H, broad-s), 6.91-6.94 (1 H, m), 7.26-7.32 (3 H, m), 7.84 (1 H, d, J = 2.4 Hz), 7.97 ( 1H, s), 8.09 (1H, s).
Solid white color EXAMPLE 1-5 Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3 - [(2-chloropyridin-3-yl) carbonylamino] benzamide (Compound No. 1-158) To a solution of 200 mg of 3-aminobenzamide N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl and 56 mg of pyrridine added to 3 ml of tetrahydrofuran, 63 mg of sodium chloride was introduced in drops. 2-chloronicotinoyl dissolved in 1 ml of tetrahydrofuran at room temperature. The reaction solution was stirred at room temperature for 2 hours, and then ethyl acetate and water were added to separate the organic phase. The organic phase was washed with 1N hydrochloric acid and an aqueous solution of saturated sodium hydrogen carbonate respectively once, and evaporated under reduced pressure to remove the solvent. The precipitated solid was washed with n-hexane to obtain 210 ml of the desired title product (yield: 84%) in the form of a solid white color. 1 H-NMR (CDCl 3, ppm) d 7.42-7.46 (1H, m), 7.60 (1H, t, J = 7.8 Hz), 7.80 (1H, d, J = 7.8 Hz), 7.94 (1H, d, J = 7.8 Hz), 8.02 (1H, s), 8.03 (1H, s), 8.22-8.28 (2H, m), 8.33 (1H, s), 8.41 (1H, s), 8.55 (1H, dd, J = 2.0 Hz and 2.9 Hz). Example 2-1 Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3- (methylamino) benzamide 5 ml of 98% sulfuric acid was cooled to a temperature of 0 ° C to 5 ° C to stir and 1.0 g of 3-aminobenzamide of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl was added. The resulting mixture was stirred for 10 minutes and subsequently 5 ml of a 37% formaldehyde aqueous solution were added dropwise. The resulting solution was maintained at a temperature between 0 ° C and 5 ° C and was stirred for 3 hours. To the reaction solution maintained in a cooled state, 28% ammonium water was added for neutralization and ethyl acetate was added to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to obtain eliminate the solvent to obtain a residue. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 6: 1) to obtain 0.74 g of the desired title product (yield: 72%) in the form of a white solid. 1 H-NMR (CDCl 3l ppm) d 2.91 (3H, s), 4.00 (1H, broad), 6.83-6.86 (1H, m), 7.17-7.24 (2H, m), 7.34 (1H, t, J = 7.8 Hz ), 7.98-8.01 (2H, m), 8.11 (1H, s). In the same method, the following compounds were prepared. 3- (Methylamino) benzamide of N- (2-bromo-4-heptafluoroisopropyl-6-pentafluoro-ethylthio) phenyl 1 H-NMR (CDCl 3, ppm) d 2.91 (3 H, s), 3.99 (1 H, broad), 6.83-6.86 (1 H, m), 7.17-7.22 (2 H, m), 7.34 (1 H, t, J = 7.8 Hz), 8.01 (2H, s), 8.08 (1H, s). Solid white color 3- (Methylamino) benzamide of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl 1 H-NMR (CDCl 3, ppm) d 2.90 (3 H, s), 3.97 (1 H, broad), 6.81-6.84 (1 H, m), 7.16-7.18 (2 H, m), 7.32 (1 H, t, J = 7.8 Hz), 7.56 (2H, s), 7.85 (1H, d, J = 2.0 Hz). Solid white color Example 2-2 Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3 - [(N '- (2,6-difluorobenzoyl) -N'-methyl) amino] benzamide (Compound No. 2-151) To a solution of 170 mg of 3- (methylamino) benzamide of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl and 28 mg of pyridine added 3 ml of tetrahydrofuran was introduced in the form of drops 52 mg of 2,6-difluorobenzoyl chloride dissolved in 1 ml of tetrahydrofuran. The reaction solution was stirred at room temperature for 2 hours, and then ethyl acetate and water were added to separate the organic phase. The organic phase was washed with 1 N hydrochloric acid and an aqueous solution of saturated sodium hydrogen carbonate respectively once, and evaporated under reduced pressure to remove the solvent. The precipitated solid was washed with n-hexane to obtain 148 mg of the desired title product (yield: 70%) in the form of a white solid. 1 H-NMR (CDCl 3, ppm) d 3.56 (3H, s), 6.69-6.74 (2H, m), 7.13-7.18 (1H, m), 7.43-7.47 (2H, m), 7.72 (1H, s), 7.77-7.81 (1H, m), 7.91 (1H, s), 8.01 (2H, s). Example 3-1 Preparation of 3- (benzoylamino) benzoic acid To 100 ml of water was added 5.90 g of sodium hydroxide and 10.0 g of 3-aminobenzoic acid, and the resulting mixture was stirred at room temperature and 10.3 g of benzoyl chloride were subsequently introduced in the form of drops, so that the internal temperature was maintained at 25 ° C to 35 ° C. The solution was stirred at room temperature for 6 hours, and then 25 ml of hydrochloric acid were introduced dropwise thereto. The precipitated solid was filtered and collected, the filtrate was washed with 100 ml of water twice and dried at a temperature of 50 ° C under reduced pressure to obtain 13.9 of the desired title product (yield: 79%) in the form of a white solid. 1 H-NMR (CDCl 3, ppm) d 7.40-7.56 (5H, m), 7.78 (1H, d, J = 7.8 Hz), 8.00 (2H, d, J = 8.3 Hz), 8.15 (1H, d, J = 7.8 Hz), 8.35 (1H, t, J = 2.0 Hz), 9.89 (1H, s). Example 3-2 Preparation of 3- (N-benzoyl-N-methylamino) benzoic acid To 70 ml of acetone were added 5.0 g of 3- (benzoylamino) benzoic acid and 2.95 g of 95% potassium hydroxide. (powder) and the resulting mixture was stirred at room temperature, and subsequently dropped into it 6. 4 g of 98% dimethyl sulfate. Upon completion of the introduction, the temperature of the resulting mixture was raised to a reflux condition, and the resulting mixture was stirred for 4 hours and cooled to room temperature. Although the insoluble substance was filtered, the solvent was removed under reduced pressure. To the resulting residue was introduced 5 ml of a 50% aqueous solution of potassium hydroxide and 20 ml of ethanol, and the result was stirred at room temperature for 2 hours. hours. The solvent was removed under reduced pressure to obtain a residue. To the resulting residue were added 50 ml of ethyl acetate and 50 ml of water to separate the aqueous phase. Hydrochloric acid with ketone was added to the aqueous phase to provide an acid solution. Subsequently, 100 ml of ethyl acetate were added and extracted. Although the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The precipitated solid was washed with a mixed solvent of n-hexane and ethyl acetate (3: 1) and dried under reduced pressure to obtain 3.80 g of the desired title product (yield: 72%) in the form of a colored solid. White. 1 H-NMR (DMSO-de, ppm) d 3.39 (3H, s), 7.21-7.31 (5H, m), 7.35-7.43 (2H, m), 7.70-7.73 (2H, m), 13.07 (1H, broad -s). Example 3-3 Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3 - [(N'-benzoyl-N'-methyl) amino] benzamide (Compound No. 2-141). 7.66 of 3- (N-benzoyl-N-) acid was added methylamino) benzoic acid, 4.28 thionyl chloride and 0.1 ml of N.N-dimethylformamide in 40 ml of toluene, and the resulting mixture was stirred at a temperature of 90 ° C for 2 hours. The reaction solution was concentrated under reduced pressure to obtain a light brown oil. The oil was introduced into 30 ml of pyridine with 4.40 g of 2-bromo-4-heptafluoroisopropyl-6- (trifluoromethylthio) aniline dissolved therein, and the resulting mixture was stirred at a temperature of 90 ° C for 8 hours. The reaction solution was diluted with ethyl acetate and the organic phase was washed with 2N hydrochloric acid and a saturated sodium hydrogen carbonate solution each time, and then concentrated under reduced pressure to obtain a brown oil. The oil was added to a mixed solvent of 40 ml of THF and 20 ml of water, and then 4.0 g of sodium hydroxide was introduced, and the resulting mixture was stirred at room temperature for 6 hours. Ethyl acetate and water were added to the reaction solution, and the organic phase was separated and subsequently washed with water once. Although the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate 9: 1 -? 2: 1) to obtain 4.06 of the desired title product (yield: 60%) in the form of a solid. White color. 1 H-NMR (CDCl 3, ppm) d 3.55 (3H, s), 7.18-7.22 (2H, m), 7.27-7.35 (4H, m), 7.42 (1H, t, J = 7.8 Hz), 7.62 (1H, s), 7.73 (1H, d, J = 7.8 Hz), 7.97 (1H, s), 7.99 (1H, s), 8.10 (1H, s). Example 4 Preparation of 3- (N'-benzoyl-N'-methyl) amino] benzamide of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoro-methylisulfinyl) phenyl (Compound No. 2-176) To 12 ml of dichloromethane was added 0.50 g of 3- (N'-benzoyl-N'-methyl) amino] benzamide of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl, and the resulting mixture was added. stirred at room temperature. Subsequently, 0.26 g of m-chloroperbenzoic acid was introduced and stirred at room temperature for 15 hours. An aqueous solution of sodium thiosulfate was added to the reaction solution, the remaining peroxide was removed, and then the organic phase was separated. The organic phase was washed with water once, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a residue. The resulting residue was purified by chromatography of silica gel column (n-hexane: ethyl acetate = 7: 3) to obtain 0.27 g of the desired title product (yield: 53%) in the form of a white amorphous substance. 1 H-NMR (CDCl 3, ppm) d 3.57 (3 H, s), 7.20-7.33 (5 H, m), 7.40 (1 H, d, J = 7.8 Hz), 7.47 (1 H, t, J = 7.8 Hz), 7.57 (1H, s), 7.71 (1H, d, J = 7.8 Hz), 8.03-8.05 (1H, m), 8.11 (1H, s), 8.26 (1H, s). Example 5 Preparation of 3- (N'-benzoyl-N'-methyl) amino] benzamide of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylsulfonyl) phenyl (Compound No. 2-191) To a mixed solution of 2 ml of dichloromethane, 2 ml of acetonitrile and 4 ml of water were added 130 mg of 3- (N'-benzoyl-N'-methyl) amino] benzamide of N- (2-bromo-4). heptafluoroisopropyl-6-trifluoromethylthio) phenyl and 120 mg of sodium periodate, and the resulting mixture was stirred at room temperature. Subsequently, 10 mg of ruthenium chloride (III) was added and stirred at room temperature for 5 hours. The reaction solution was added to a aqueous solution of sodium thiosulfate, the remaining peroxide was removed, and then 30 ml of ethyl acetate were introduced to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate and then the solvent was removed under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 5: 3) to obtain 82 mg of the desired title product (yield: 60%) in the form of a white amorphous substance . 1 H-NMR (CDCl 3, ppm) d 3.57 (3H, s), 7.18-7.36 (6H,), 7.43 (1H, t, J = 7.8 Hz), 7.61 (1H, d, J = 2.0 Hz), 7.68 ( 1H, d, J = 7.8 Hz), 8.28 (1H, d, J = 2.0 Hz), 8.32 (1H, d, J = 2.0 Hz), 8.76 (1H, s). Example 6-1 Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3- (benzoylamino) benzamide To a solution of 300 mg of 3-aminobenzamide of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl prepared in example 1-4 and 85 mg of added pyridine of 3 ml of tetrahydrofuran was introduced in the form of drops 75 mg of Benzoyl chloride dissolved in 1 ml of tetrahydrofuran at room temperature. The resulting mixture was stirred at room temperature for 2 hours and then added to ethyl acetate and water to separate the organic phase. The organic phase was washed with 1N hydrochloric acid and a saturated solution of sodium hydrogen carbonate respectively each time, and the solvent was removed under reduced pressure to precipitate a solid. The resulting solid was washed with n-hexane to obtain 345 mg of the desired title product (yield: 97%) in the form of a white solid. H-NMR (DMSO-d6, ppm) d 7.53-7.64 (4H, m), 7.81 (1H, d, J = 7.8 Hz), 8.00-8.05 (3H, m), 8.11 (1H, d, J = 7.8 Hz), 8.31 (1H, d, J = 1.5 Hz) 8.41 (1H, s), 10.52 (1H, s), 10.93 (1H, s). Example 6-2 Preparation of 3- (benzoylamino) benzamide of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylsulfonyl) phenyl (Compound No. 1-191) 0.34 g of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3- (benzoylamino) benzamide and 0.33 were added. g of sodium periodate to a mixed solution of 2.5 ml of dichloromethane, 2.5 ml of acetonitrile and 5 ml of water, and the resulting mixture was stirred at room temperature. Subsequently, 10 mg of ruthenium chloride (III) was added and stirred at room temperature for 7 hours. Sodium bisulfite was added to the reaction solution and peroxide was dissolved therein, and then ethyl acetate was added to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 2: 1) to obtain 0.23 g of the desired title product (yield: 65%) in the form of a white solid. 1 H-NMR (DMSO-de, ppm) d 7.53-7.63 (4H, m), 7.74 (1H, d, J = 7.8 Hz), 7.98-8.01 (2H, m), 8.08 (1H, d, J = 8.3 Hz), 8.24 (1H, s), 8.38 (1H, t, J = 1.5 Hz), 8.81 (1H, s), 10.51 (1H, s), 10.82 (1H, s). Example 7 Preparation of 4-heptafluoroisopropyl-2-methyl-6- (trifluoromethylthio) aniline 0.92 g of 2-bromo-4-heptafluoroisopropyl-6 were added (trifluoromethylthio) aniline, 0.13 g of trimethylboroxin and 1.44 g of potassium carbonate to a mixed solvent of 10 ml of toluene, 5 ml of ethanol and 5 ml of water, and the resulting mixture was stirred under a nitrogen atmosphere at room temperature . Subsequently, although 0.2 g of tetrakis (triphenylphosphine) palladium (0) was introduced, the resulting solution was raised to a temperature of 80 ° C and stirred for 8 hours. The solution was checked at room temperature, the insoluble substance and filtered, and then ethyl acetate and water were added to separate the organic phase. The organic phase was separated over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 20: 1) to obtain 0.31 of the desired title product (yield: 40%) in the form of a light yellow oil. 1 H-NMR (CDCl 3, ppm) d 2.24 (3 H, s), 4.77 (2 H, broad-s), 7.34 (1 H, s), 7.60 (1 H, s). Example 8-1 Preparation of N- (2-chloro-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl 3-nitrobenzamide 1.17 g of 3-nitrobenzoyl chloride and 1.20 g of (2-chloro-4-heptafluoroisopropyl-6-trifluoromethoxy) aniline were added to 8 ml of pyridine, and the resulting mixture was stirred at a temperature of 90 ° C for 6 hours . To the reaction solution were added ethyl acetate and 1N hydrochloric acid, the organic phase was separated in a state in which the aqueous phase was made acidic., and then the organic phase was washed with a saturated solution of sodium hydrogen carbonate twice. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to obtain a residue. The resulting residue was added to a mixed solution of 10 ml of tetrahydrofuran and 5 ml of water. To the solution 0.32 sodium hydroxide was added, and the resulting mixture was stirred at room temperature for 1 day. To the reaction solution were added ethyl acetate and water to separate the organic phase, and then the solvent was removed under reduced pressure to obtain a residue. The resulting residue was purified by chromatography on a silica gel column (n-hexane: ethyl acetate = 4: 1) to obtain 1.20 g of the desired title product (yield: 72%) in the form of a white solid. 1 H-NMR (CDCl 3, ppm) d 7.56 (1H, s), 7.71-7.79 (3H, m), 8.30 (1H, d, J = 7.8 Hz), 8.48-8.51 (1H, m), 8.77 (1H, t, J = 2.0 Hz).
Example 8-2 Preparation of 3-aminobenzamide of N- (2-chloro-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl Using N- (2-chloro-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl 3-nitrobenzamide as a starting raw material, the desired title product was prepared according to the conditions described in Example 1-4 . Solid white color Yield 86%. 1 H-NMR (CDCl 3, ppm) d 3.39 (2 H, broad-s), 6.89-6.92 (1 H, m), 7.22-7.32 (3 H, m), 7.52-7.53 (2 H, m), 7.69 (1 H, d , J = 1.5 Hz). Example 8-3 Preparation of 3- (benzoylamino) benzamide of N- (2-chloro-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl (Compound No. 1-241) Using 3-aminobenzamide of N- (2-chloro-4-) heptafluoroisopropyl-6-trifluoromethoxy) phenyl as a starting raw material, the desired title product was prepared according to the conditions described in Example 1-5. Solid white color Performance: 80%. 1 H-NMR (CDCl 3l ppm) d 7.36-7.43 (3H, m), 7.47-7.53 (2H, m), 7.63-7.65 (2H, m), 7.81-7.87 (3H, m), 8.20 (1H, s) , 8.28 (1H, s), 8.39 (1H, s). Example 9-1 Preparation of 2- (2,2,2-trifluoroethoxy) nitrobenzene A solution of 1.70 g of 60% sodium hydride added to 20 ml of N, N-dimethylformamide was stirred at a temperature of 5 ° C, and 4.25 g of 2,2,2-trifluoroethanol were added as drops. dissolved in 5 ml of N, N-dimethylformamide. The resulting solution was returned to room temperature and stirred for 1 hour, and 5.0 g of 2-fluoronitrobenzene dissolved in 5 ml of N, N-dimethylformamide were subsequently introduced in the form of drops. Subsequently, the reaction solution was stirred at room temperature for 2 hours and diluted with ethyl acetate, and subsequently the water was introduced to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to get a residue. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 6: 1) to obtain 8.14 g of the desired title product (yield: 90%) in the form of a yellow oil. 1 H-NMR (CDCl 3, ppm) d 4.50 (2H, q, J = 7.8 Hz), 7.13-7.22 (2H, m), 7.57-7.62 (1H, m), 7.88 (1H, dd, J = 2.0, 8.3 Hz). Example 9-2 Preparation of 2- (2,2,2-trifluoroethoxy) aniline 3. 50 g of 2- (2,2,2-trifluoroethoxy) nitrobenzene and 0.15 g of palladium carbonate were added to 10% methanol and the resulting mixture was stirred under atmospheric pressure under a hydrogen atmosphere at room temperature for 3 hours. The insoluble substance was filtered and then the filtrate was concentrated under reduced pressure to obtain 2.86 g of the desired title product (yield: 95%) in the form of a yellow oil. 1 H-NMR (CDCl 3, ppm) d 3.83 (2 H, broad-s), 7.34 (2 H, q, J = 8.3 Hz), 6.68-6.78 (3H, m), 6.85-6.90 (1H, m). Example 9-3 Preparation of 4-heptafluoroisopropyl-2- (2,2,2-trifluoroethoxy) aniline 2.85 g of 2- (2,2,2-trifluoroethoxy) aniline, 6.62 g of 2-iodoheptafluoropropane, 3.11 g of sodium hydrosulfite, 1.50 g of sodium hydrogen carbonate and 0.61 g of tetra-n-hydrogensulfate were added. Butyl ammonium was added to a mixed solvent of 30 ml of t-butyl methyl ether and 30 ml of water, and the resulting mixture was stirred vigorously at room temperature for 12 hours. The organic phase was separated and washed with a saturated solution of sodium hydrogencarbonate, and then evaporated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 9: 1) to obtain 13.99 g of the desired title product (yield: 74%) in the form of a light yellow oil. 1 H-NMR (CDCl 3, ppm) d 4.14 (2 H, broad-s), 4.69 (1 H, q, J = 7.8 Hz), 6.79 (1 H, d, J = 8.3 Hz), 6.95 (1 H, s), 7.11 (1H, d, J = 8.3 Hz). Example 9-4 Preparation of 2-bromo-4-heptafluoroisopropyl-6- (2,2,2-trifluoroethoxy) aniline Using 4-heptafluoroisopropyl-2- (2,2,2-trifluoroethoxy) aniline as the starting raw material, the desired title product was prepared according to the conditions described in example 1-2. Brown oil Yield: 88%. 1 H-NMR (CDCl 3, ppm) d 4.41 (1 H, q, J = 7.8 Hz), 4.58 (2 H, broad-s), 6.90 (1 H, s), 7.39 (1 H, s). Example 9-5 Preparation of N- [2-bromo-4-heptafluoroisopropyl-6- (2,2,2-trifluoroethoxy)] phenyl 3 - [(N'-benzoyl-N'-methyl) amino] benzamide (Compound No. 2-269) Using 2-bromo-4-heptafluoroisopropyl-6- (2,2,2-trifluoroethoxy) aniline as the starting raw material, the desired title product was prepared according to the conditions described in Example 3-3 . Amorphous substance white color Yield: 69%. 1 H-NMR (CDCl 3, ppm) d 3.54 (3H, s), 4.42 (1H, q, J = 7.8 Hz), 7.14-7.21 (3H, m), 7.24-7.31 (4H, m), 7.37 (1H, t, J = 7.8 Hz), 7.46 (1H, s), 7.60-7.62 (2H, m), 7.66-7.69 (1H, m).
Example 10-1 Preparation of 4- [1-hydroxy-2,2,2-trifluoro-1 (trifluoromethyl) ethyl] -2- (trifluoromethylthio) aniline While 5.0 g of 2-trifluoromethylthio aniline and 6.5 g of hexafluoroacetone hydrate were mixed at room temperature, 0.1 g of p-toluenesulfonic acid monohydrate was added, and the reaction solution was stirred at a temperature of 100 ° C for 20 hours. Once the disappearance of the unprocessed starting material by the TLC was confirmed, ethyl acetate, and a saturated sodium hydrogen carbonate solution were added to the reaction solution for separation and removal of the solution. The organic phase was added anhydrous magnesium sulfate, the organic phase was dried and filtered. The filtrate was concentrated under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1) to obtain 4.74 g of the desired title product, (yield: 51%) in the form of a brown oil. Dark. 1 H-NMR (CDCl 3, ppm) d 4.71 (2 H, broad), 6.81 (1 H, d, J = 8.8 Hz), 7.58 (1 H, d, J = 8.8 Hz), 7.84 (1 H, d, J = 1.5 Hz ).
Example 10-2 Preparation of 2-bromo-4- [1-hydroxy-2.2.2-trifluoro-1 (trifluoromethyl) ethyl] -6- (trifluoromethylthio) aniline Using 4- [1-hydroxy-2, 2, 2-trifluoro-1 - (trifluoro methyl) ethyl] -2- (trifluoromethylthio) aniline as a starting unprocessed material, the desired title product was prepared in accordance with the conditions described in example 1-2. Oil color red. Performance: 81%. Example 10-3 Preparation of 3-nitrobenzamide of N- [2-bromo-4- (1-hydroxy-2, 2, 2-trifluoro-1 - (trifluoro methyl) eti I) -6- (trifluoromethylthio) phenyl] Using 2-bromo-4- [1-hydroxy-2, 2, 2-trifluoro-1- (trifluoromethyl) ethyl] -6- (trifluoromethylthio) aniline as a starting raw material, the desired title product was prepared according to the conditions described in the example 1-3. Solid white color Yield: 70%. Example 10-4 Preparation of 3-aminobenzamide N- [2-bromo-4- (1-h id roxy-2, 2, 2-trif I uoro-1 - (trifluoromethyl) ethyl] -6- (trifluoromethylthio) phenyl ] Using 3-nitrobenzamide of N- [2-bromo-4-. { 1-Hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] as an unprocessed starting material, the desired title product was prepared according to the conditions described in example 1-4. Solid white color Performance: 90%. Example 10-5 Preparation of 3 - [(2-fluorobenzoyl) amino] benzamide of N- [2-bromo-4-. { 1-h id roxi-2, 2, 2-trif luoro- 1 - (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] Using 3-aminobenzamide of N- [2-bromo-4-. { 1 -hydroxy- 2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] and 2-fluorobenzoyl chloride as unprocessed starting materials, the desired title product was prepared according to the conditions described in Example 1-5. Solid white color Yield: 84%. Example 10-6 Preparation of 3 - [(2-fluorobenzoyl) amino] benzamide of N- [2-bromo-4-. { 1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] At room temperature, 1.0 g of 3 - [(2-fluorobenzoyl) amino] benzamide of N- [2-bromo-4-. { 1-Hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] and 0.2 g of pyridine to 10 ml of thionyl chloride. Subsequently, the temperature of the resulting solution was raised and the resulting solution was stirred under a reflux condition. Once the disappearance of the unprocessed material by TLC was confirmed, the reaction solution was cooled and then concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 3: 1) to obtain 0.77 g of the desired title product (Yield: 75%) in the form of a white solid. Example 10-7 Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3 - [(2-fluorobenzoyl) amino] benzamide (Compound No. 1-143) At room temperature 400 mg of 3 - [(2-fluorobenzoyl) amino] benzamide of N- [2-bromo-4-. { 1-chloro-2,2,2-trifluoro-1 - (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] and 166 mg of potassium fluoride to 10 ml of N, N-dimethylformamide. Subsequently, the resulting solution was raised to a temperature of 120 ° C and stirred for 5 hours. The reaction solution was cooled to room temperature, and then ethyl acetate and water were added thereto to separate the organic phase. Anhydrous magnesium sulfate was added to the organic phase, and the organic phase was dried and filtered. The filtrate was concentrated under reduced pressure. To the resulting residue, diisopropyl ether was added for washing. The filtered product obtained by filtering a suspension, it was dried under vacuum at room temperature to obtain 281 mg of the desired title product (Yield: 72%). 1 H-NMR (DMSO-d 6, ppm) d 7.33-7.40 (2H, m), 7.57-7.62 (2H, m), 7.68-7.73 (1H, m), 7.81 (1H, d, J = 7.8Hz), 8.01 (1H, d, J = 7.8Hz), 8.04 (1H, s), 8.30 (1H, d, J = 2.0Hz), 8.37 (1H, s), 10.70 (1H, s), 10.95 (1H, s ). Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylthio) phenyl 3 - [(2-fluorobenzoyl) amino] benzamide (Compound number 1-143) At room temperature, 300 mg of 3 - [(2-fluorobenzoyl) amino] benzamide of N- [2-bromo-4-. { 1-chloro-2,2,2-trifluoro-1- (trifluoromethyl) ethyl} -6- (trifluoromethylthio) phenyl] to 20 ml of methylene chloride. Subsequently, 470 mg of 2,2-difluoro-1,3-dimethyl-2-imidazolindinone was added in the form of drops and stirred at room temperature for 8 hours. Water was added to the reaction solution to separate the organic phase. To the organic phase anhydrous magnesium sulfate was added, and the organic phase was dried and filtered. The resulting filtrate was evaporated to be dried to obtain a solid. The resulting solid was pulverized to obtain 181 mg of the desired product (Yield: 60%) in the form of a powder. The physical properties are described in Example 10-7. Example 11-1 Preparation of 2-trifluoromethoxy-4- [1-hydroxy-2,2,2-trifluoro-1 (trifluoromethyl) ethyl] aniline While 3.38 g of 2-trifluoromethoxyaniline and 4.75 g of hexafluoroacetone hydrate were mixed without mixing at room temperature, 0.1 g of p-toluenesulfonic acid monohydrate was added and the reaction solution was stirred at a temperature of 100 ° C for 20 minutes. hours. Once the disappearance of the unprocessed starting material was confirmed by TLC, ethyl acetate and a saturated solution of sodium hydrogen carbonate were added to the reaction solution for separation and extraction of the solution. To the organic phase anhydrous magnesium sulfate was added, the organic phase was dried and filtered. The filtrate was concentrated under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1) to obtain 3.60 g of the desired title product (Yield: 55%) in the form of a dark brown oil . 1 H-NMR (CDCl 3, ppm) d 3 37 (1 H, broad-s), 4.10 (2 H, broad-s), 6.83 (1 H, d, J = 8.8 Hz), 7.39 (1 H, d, J = 8.8 Hz ), 7.50 (1H, s). Example 11 -2 Preparation of 2-bromo-4- [1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] -6-trifluoromethoxyaniline Using 2-trifluoromethoxy-4- [1-hydroxy-2,2,2-trifluoro-1- (trifluoromethyl) ethyl] aniline as an unprocessed raw material, the desired title product was prepared according to the conditions that were describe in example 1-2. Oil color red. Yield: 92%. 1 H-NMR (CDCl 3, ppm) d3.98 (1 H, t, J = 2.4 Hz), 4.55 (2 H, broad-s), 7.47 (1 H, s), 7.71 (1 H, d, J = 1.5 Hz). Example 11-3 Preparation of 3- (benzoylamino) benzamide of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethoxy) phenyl (Compound number 1-243) Using 2-bromo-4- [1-h id roxy-2, 2, 2-trifluoro-1- (trifluoromethyl) ethyl] -6-trifluoromethoxyaniline as an unprocessed starting material, the desired title product of according to the conditions described in examples 10-3 to 10-7. Solid white color 1 H-NMR (DMSO-d 6, ppm) d7.48-7.67 (4H, m), 7.73-7.81 (2H, m), 7.94-8.14 (4H, m), 8.38 (1H, s), 10.51 (1H, s), 10.63 (1H, s). Example 12-1 Preparation of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylsulfinyl) phenyl 3-nitrobenzamide 9.56 of N- (2-bromo-4-heptafluoroisopropyl-6-trifluoromethylsulfinyl) phenyl prepared in Example 1-3 and 2.80 g of m-chloroperbenzoic acid were added to 100 ml of dichloromethane, and the resulting mixture was added. stirred at room temperature overnight. To the reaction solution was added 2.70 g of metachloroperbenzoic acid and the resulting mixture was stirred further at room temperature for 96 hours. An aqueous solution of saturated sodium thiosulfate was added to the reaction solution to separate the organic phase. The organic phase was washed with water and it was subsequently dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 10: 1) to obtain 5.80 g of the desired product (Yield: 59%) in the form of a white solid. 1 H-NMR (CDCl 3, ppm) d7.80 (1 H, t, J = 7.8 Hz), 8.18 (1 H, d, J = 2.0 Hz), 8.24 (1 H, s), 8.30 (1 H, dd, J = 2.0 , 7.8 Hz), 8.46 (1H, s), 8.53 (1H, dd, J = 2.0, 7.8 Hz), 8.80 (1H, t, J = 2.0 Hz). Example 12-2 Preparation of 3-aminobenzamide of N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 1.02 g of N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 3-nitrobenzamide and 0.99 g of tin (II) chloride (anhydride) were added to 10 ml of ethanol, and introduced Subsequently in the form of drops 1 ml of concentrated hydrochloric acid. After the introduction, the resulting solution was raised to a temperature of 60 ° C and stirred for 4 hours. The reaction solution was neutralized with sodium hydroxide under cooling with ice. The resulting precipitated insoluble substance was filtered through celite. He The product filtered on celite was washed with ethyl acetate. The organic phase of the filtrate was washed with an aqueous solution of 20% sodium hydroxide and saturated salt water, and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 1) to obtain 0.83 g of the desired product (Yield: 85%) in the form of a white solid. 1 H-NMR (CDCl 3) ppm) d 3.95 (2 H, broad), 6.92 (1 H, dd, J = 2. 0, 7.3Hz), 7.23 (1H, s), 7.24 (1H, d, J = 7.3 Hz), 7.31 (1H, t, J = 7.3 Hz), 8.11 (1H, d, J = 7.3 Hz), 8.17 (1H, s), 8.30 (1H, s). Example 12-3 Preparation of N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 3- (methylamino) benzamide To 10 ml of concentrated sulfuric acid were added 1. 96 g of N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 3-aminobenzamide and the resulting mixture was stirred. Subsequently, 5.6 ml of a 37% aqueous formaldehyde solution was added in the form of droplets, while the solution temperature was maintained. from 30 to 40 °, and the resulting solution was stirred at room temperature for 8 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic phase was washed with an aqueous solution of 20% sodium hydroxide and water, and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain a residue. The resulting residue was washed with diisopropyl ether to obtain 1.30 g of desired product (Yield: 65%) in the form of a white solid. 1 H-NMR (DMSO, d 6, ppm) d 2 80 (3 H, s), 4.99 (1 H, broad), 7. 07-7.08 (1H, m), 7.28 (1H, d, J = 7.3Hz), 7.48-7.49 (1H, m), 7.51 (1H, s), 8.13 (1H, d, J = 2.0Hz), 8.24 (1H, s), 10.12 (1H, broad). Example 12-14 Preparation of 3-. { [N '- (2-chloropyridin-3-yl) carbonyl-N'-methyl] amino} N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl benzamide (Compound No. 2-180) Using N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl 3- (methylamino) benzamide as an unprocessed starting material and 2-chloronicotinoyl chloride, the desired title product was prepared according to the conditions described in Example 1-5. White amorphous substance. Yield: 70%. 1 H-NMR (CDCl 3, ppm) d 3.58 (3H, s), 7.15 (1H, dd, J = 4.9, 7.3 Hz), 7.42-7.45 (2H, m), 7.60 (1H, d, J = 7.3 Hz ), 7.71-7.72 (2H, m), 8.13 (1H, s), 8.19-8.29 (3H, m). Example 12-5 Preparation of 3-. { [N'-pyrimidin-5-yl) carbonyl-N'-methyl] amino} Benzamide of N-2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl (Compound 2-281) Using 3-aminobenzamide of N- [2-bromo-4-heptafluoroisopropyl-6- (trifluoromethyl) sulfinyl] phenyl prepared in Example 12-3 as an unprocessed starting material and pyrimidine-5-carboxyl chloride, the product of the desired title according to the conditions described in Example 1-5. Solid light yellow color. Yield: 53%. 1 H-NMR (CDCl 3> ppm) d3.59 (3H, s), 7.34 (1H, d, J = 8.3Hz), 7.51 (1H, t, J = 7.8Hz), 7.78 (2H, dd, J = 3.9, 1.5Hz), 8.14 (1H, d, J = 2.0Hz), 8.24 (1H, s), 8.35 (1H, s), 8.67 (2H, s), 9. 11 (1H, s). The examples of the formulation, which include the compound represented by the general formula (1) of the present invention as an active ingredient, will be illustrated below. However, the present invention is not restricted to these formulation examples. Incidentally, in the formulation examples, the term "part (s)" means "part (s) by weight" Formulation Example 1 20 parts of compound represented by the general formula (1) of the compound were stirred and mixed in a uniform manner. present invention, 10 parts of Sorpol 355S (an active surface agent, a product of TOHO Chemical Industry, Co., Ltd.) and 70 parts of xylene, to obtain an emulsifiable formulation Formulation example 2 They were stirred and mixed in a manner uniform 10 parts of the compound represented by the general formula (1) of the present invention, 2 parts of sodium alkylnaphthalene sulfonate, 1 part of sodium lignin sulfonate, 5 parts of white carbon and 82 parts of diatomaceous earth, to obtain a wettable powder Formulation Example 3 0.3 parts of the compound represented by the general formula (1) of the present invention, and 0.3 parts of white carbon, and 99.2 parts of clay and 0.2 parts of Driless A (a product of Sankyo Co., Ltd.) were added. The resulting mixture was pulverized and mixed uniformly to obtain a powder formulation. Formulation Example 4 2 parts of the compound represented by the general formula (1) of the present invention were uniformly pulverized and mixed., 2 parts of white carbon, 2 parts of sodium lignin sulfonate and 94 parts of bentonite, and then water was added. The resulting mixture was kneaded, granulated and dried to obtain a granule. Formulation Example 5 20 parts of the compound represented by the general formula (1) of the present invention and 5 parts of a 20% aqueous polyvinyl alcohol solution were agitated and thoroughly mixed, and subsequently 75 parts were added. of a 0.8% aqueous solution of xanthan gum. The resulting mixture was stirred and mixed again to obtain a flowable formulation. In addition, to ensure that the compound represented by the general formula (1) of the present invention has an excellent insecticidal activity, the following test examples are illustrated. However, the present invention is not restricted to these examples.
Test Example 1 Insecticidal test on Common Falena Larva (Spodoptera litura) A piece of cabbage leaf was immersed for 30 seconds in a liquid chemical prepared by diluting a test compound in a prescribed concentration. After drying with air, the piece was placed in a 7 cm polyethylene bowl and instar-second larvae of common larvae were released. The polyethylene bowls were adjusted in an isothermal chamber, thermoadjusted at a temperature of 25 ° C. From the release 6 days later, death and survival were counted. The test was carried out with two replicas of 5 insects per stroke. As a result of the above test, a concentration of 100 ppm, of the following compounds, showed 70% mortality or more: Compounds numbers 1-1, 1-94, 1-143, 1-145, 1-146, 1- 148, 1-149, 1-150, 1-151, 1-152, 1-158, 1-166, 1-176, 1-180, 1-191, 1-195, 1-201, 1-202, 1-203, 1-204, 1-205, 1-207, 1-241, 1-242, 1-243, 1-244, 1-245, 1-246, 1-247, 1-248, 1- 249, 1-253, 1-254, 1-255, 1-256, 1-257, 1-258, 1-259, 1-260, 1-261, 1-262, 1-263, 1-264, 1-265, 1-266, 1-269, 1-270, 2-141, 2-143, 2-145, 2-148, 2-151, 2-152, 2-158, 2-172, 2- 173, 2-174, 2-175, 2-176, 2-177, 2-178, 2-179, 2-180, 2-181, 2-191, 2-195, 2-201, 2-203, 2-207, 2-243, 2-260, 2-261, 2-262, 2-269, 2-270, 2-281, 3-49 and 3-51.
Test example 2 Insecticide test on diamondback aphid (Plutella xylostella) A piece of a cabbage leaf was immersed for 30 seconds in a liquid chemical prepared by diluting a test compound in a prescribed concentration. After drying with air, the piece was placed in a 7 cm polyethylene bowl and there were released on it, instar-second larvae of diamond back aphids. The polyethylene bowls were fitted in a thermo-adjusted isothermal chamber at a temperature of 100 ppm. From the release 6 days later, death and survival were counted. The test was carried out with two replicas of 5 insects per stroke. As a result of the above test, at a treatment concentration of 100 ppm, the following compounds showed 70% mortality or more: Compounds numbers 1-1, 1-8, 1-94, 1-143, 1-145, 1 -146, 1-148, 1-149, 1-150, 1-151, 1-152, 1-158, 1-166, 1-176, 1-180, 1-191, 1-195, 1-201 , 1-202, 1-203, 1-204, 1-205, 1-207, 1-241, 1-242, 1-243, 1-244, 1-245, 1-246, 1-247, 1 -248, 1-249, 1-253, 1-254, 1-255, 1-256, 1-257, 1-258, 1-259, 1-260, 1-261, 1-262, 1-263 , 1-264, 1-265, 1-266, 1-269, 1-270, 2-141, 2-143, 2-145, 2-148, 2-151, 2-155, 2-158, 2 -172, 2-173, 2-174, 2-175, 2-176, 2-177, 2-178, 2-179, 2-180, 2-181, 2-191, 2-195, 2-201 , 2-203, 2-207, 2-243, 2- 260, 2-261, 2-262, 2-269, 2-270, 2-281, 3-49 and 3-51. Test example 3 Insecticide test on western flower louse (Franklinella occidentalis) In a plastic bowl, (diameter: 5 cm, height: 5 cm) 1% agar gel was poured, and the reverse side of a primary leaf of common bean, cut with a diameter of 4.5 cm was placed upward to prepare a leaf disk. Three adult female insects that had already been collated were released, and the resulting material was capped to produce eggs for 2 days. Subsequently, adult female insects were taken and 4 days later, the number of larvae on the leaf disc was counted and a chemical was dispersed therein at the prescribed concentration using a vertical sprayer. 3 days after the dispersion, the surviving insects were counted. Mortality adjusted according to the following equation was calculated. Adjusted mortality = 100 x Ta x Cb / (Tb x Ca) Ta: the number of surviving insects after dispersion in a treated plot. Tb: number of surviving insects before dispersion in a treated plot. Ca: number of surviving insects after dispersion in an untreated plot. Cb: number of surviving insects before the dispersion in an untreated plot. As a result of the above test, at a treatment concentration of 300 ppm, the following compounds showed 30% adjusted mortality or less: Compounds numbers 1-143, 1-45, 1-148, 1-158, 1-176, 1-180, 1-195, 1-243, 1-244, 1-245, 1-141, 1-143, 2-158, 2-176, 2-177, 2-178, 2-179, 2-180, 2-181, 2-243 and 2-281. Test example 4 Insecticide test on melon louse (Thrips palmi) In a plastic bowl (diameter: 5 cm, height: 5 cm), 1% agarose gel was poured, and the reverse part of an agarose was placed upwards. Cucumber leaf cut into a diameter of 4. 5 cm, to prepare a leaf disc. A chemical was dispersed to the prescribed concentration using a vertical sprayer. After drying with air, 5 adult melon lice were released and the resulting material was capped. 3 days later, the number of surviving insects was counted and the mortality was calculated. As a result of the above test, at a treatment concentration of 300 ppm, the following compounds showed mortality at 70% or more: Compounds numbers 1-143, 1-145, 1-158, 2-141 and 2-158. Test example 5 Insecticide test on onion louse (Thrips tabaci) A chemical was dispersed in the prescribed concentration on onion seedlings, dried with air, and later both the sowings and 5 adult onion lice insects were placed in a glass test tube (diameter: 3 cm, height: 10 cm). The resulting material was covered. 3 days later, the number of surviving insects was counted and the mortality was calculated. As a result of the above test, at a treatment concentration of 300 ppm, the following compounds showed mortality at 70% or more: Compounds numbers 1-143, 1-145, 1-148, 1-158, 1-243, 1 -245, 2-141, 2-143 and 2-158. Comparative Example 1 Insecticidal test using N- (4-heptafluoroisopropyl-2-methylphenyl) (Compound A) and 3- (benzoylamino) benzamide 3- (2-iodobenzoylamino-benzamide) of N- (2,6-dimethyl-4-trifluoromethylphenyl (Compound B) The title compounds A and B were provided in the form of chemicals for use in test examples 1 to 5, but the insecticidal activity could not be confirmed under the same conditions.

Claims (20)

  1. CLAIMS 1. A compound represented by the general formula (1), wherein, in the formula, Ai, A2, A3, and A, each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom; RT and R2 are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group; d and G2 are each independently an oxygen atom or a sulfur atom, Xs are each independently a hydrogen atom, a halogen atom, or a trifluoromethyl group; n represents an integer from 0 to 4; QT is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group , a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, an alkylsulfinyl group of C1-C3, a haloalkylsulfinyl group of C1-C3, a alkylsulfonyl group of C1-C3, a haloalkylsulfonyl group of C1-C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a heterocyclic group ( heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group , a thiazolyl group, an isothiazoline group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, an alkylsulfinyl group of C1-C3, a haloalkylsulfinyl group of C1-C3, a alkylsulfonyl group of C1-C3, a haloalkylsulfonyl group of C1-C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described above); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, YT represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group of C1-C3, a C1-C3 alkylsulfinyl group, a group C1-C3 haloalkylsulfinyl, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Y6 and Y9 each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkylthio group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulfonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Yg must represent a C1-C4 alkoxy group, a haloalkoxy group of C1-C4, a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3); 2. A compound represented by the general formula (1), wherein, in the formula, Ai, A2, A3, and A4, each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom; R 1 and R 2 each independently represent a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkylcarbonyl group; d and G2 each independently represent an oxygen atom or a sulfur atom, Xs each independently represent a hydrogen atom, a halogen atom, or a trifluoromethyl group; n represents an integer from 0 to 4; QT is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, an alkylthio group of C1-C3, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an C 1 -C 4 alkylamino group, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group C4, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group , a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, a group isothiazolyl, an imidazole group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group having one or more substituents which may be the same or different (substituents are selected from an atom of halogen, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkenyl group, a C 2 -C 4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, an alkylthio group of C1-C3, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an C 1 -C 4 alkylamino group, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group C4, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described above); and Q2 is represented by the general formula (2) or (3), where, in the formula, < Represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group from C1- C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Y6 and Y9 each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y 6 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkylthio group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulphonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Yg must represent a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group), therefore, compounds are excluded , where and! represents a trifluoromethylthio group; Y2 and Y4 represent hydrogen atoms; Y3 represents a heptafluoroisopropyl group; Y 5 represents a bromine atom; X represents a hydrogen atom; GT and G2 represent oxygen atoms; RT and R2 represent hydrogen atoms; and Qi represents an unsubstituted phenyl group. 3. The compound as described in claim 1 or 2, represented by the general formula (1a), wherein AL A2, A3 and A4 in the general formula (1), are all carbon atoms wherein, in the formula, when any of RT and R2 are a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both of RT and R2 are C1-6 alkyl groups C4 or C1-C4 alkylcarbonyl groups; d and G2 are each independently an oxygen atom or a sulfur atom; Xi, X2, X3, and are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; QT is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group , a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, an alkylsulfonyl group of C1-C3, a haloalkylsulfonyl group of C1-C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, an alkylcarbonyl group of C1-C4, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a group heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, a group oxazolyl, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group , a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group , an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described previously); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, Yi represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group of C1-C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Y6 and Yg each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-6 alkoxy group, C4, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a haloalkylsulfonyl group of C1-C3 or a cyano group; Y8 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkylthio group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulfonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Ye and Yg must represent a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a C1-C3 haloalkylsulfonyl group). 4. The compound as described in claim 3, characterized in that Q2 is represented by the general formula (2) wherein, in the formula, Yi represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group from C1- C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. 5. The compound as described in claim 4, characterized in that QT represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a haloalkyl group of C1-C4, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3- halocycloalkyl group C6, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom , a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, an alkylsulfinyl group of C1-C3, a haloalkylsulfinyl group of C1-C3, a group alkylsulfonyl of C1-C3, a haloalkylsulfonyl group of C1-C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a group C 1 -C 4 alkoxycarbonyl, an acetylamino group and a phenyl group). 6. The compound as described in [1] or [2], represented by the general formula (1a), wherein A1t A2, A3 and A4 in the formula (1), are all carbon atoms wherein, in the formula, Ri and R2 each independently represent a hydrogen atom, a C1-C4 alkyl group, or a C1-C4 alkylcarbonyl group; d and G2 are each independently an oxygen atom or a sulfur atom; Xi, X2, X3, and X are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; QT is a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, an alkenyl group of C2-C4, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1 alkoxy group -C3, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group , a C1-C3 haloalkylsulfonyl group, an amino group, a group C 1 -C 4 alkylamino, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group , an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2 haloalkenyl group -C4, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group , a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a amino group, a group C 1 -C 4 alkylamino, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group , an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described above); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, Yi represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group of C1-C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Y6 and Yg each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkylthio group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulfonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Y9 must represent a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a C1-C3 haloalkylsulfonyl group). 7. The compound as described in the claim 6, characterized because Q? represents a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, an alkenyl group of C2-C4, a group C2-C4 haloalkenyl, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a haloalkoxy group of C1-C3, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1- C3 haloalkylsulfonyl group, C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, an alkylcarbonyl group of C1-C4, an alkylcarbonyloxy group of C1-C4 , a C 1 -C 4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (the substituents are selected from an halogen, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkenyl group, a haloalkyl group C2-C4 enyl, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a haloalkoxy group of C1-C3, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1- C3 haloalkylsulfonyl group, C3, an amino group, a group C 1 -C 4 alkylamino, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, a C 1 -C 4 alkoxycarbonyl group , an acetylamino group and a phenyl group); and Q2 is represented by the general formula (2), wherein, in the formula, Y-i represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group of C1-C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. 8. The compound as described in the claim 1 or 2, represented by the general formula (1a), wherein A ,, A2, A3 and A4 in the general formula (1) are all carbon atoms wherein, in the formula, Ri and R2 are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, and G2 are each independently an oxygen atom or an oxygen atom. sulfur; X ?, X2, X3, and X are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; Qi is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group , a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group , a C 1 -C 4 alkylamino group, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, an alkoxycarbonyl group of C1-C4, an acetylamino group and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group that has one or more substitutes which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2- haloalkenyl group C4, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group , a C 1 -C 4 alkylamino group, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, an alkoxycarbonyl group of C1-C4, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described above); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, Yi represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a fluorine atom, a chlorine atom, an iodine atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a group C 1 -C 3 alkylthio, a C 1 -C 3 haloalkylthio group, a C 1 -C 3 alkylsulfinyl group, a C 1 -C 3 haloalkylsulfinyl group, a C 1 -C 3 alkylsulfonyl group, a C 1 -C 3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Ye and Yg each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, an alkylsulfonyl group of C1-C3, a haloalkylsulfonyl group of C1-C3 or a cyan group; Y8 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkyl group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulfonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Yg must represent a haloalkyl group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a C1-C3 haloalkylsulfonyl group). 9. The compound as described in the claim 8, characterized in that Qi represents a phenyl group a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a haloalkyl group of C1-C4, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3- halocycloalkyl group C6, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamin group or and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (substituents are selected from a halogen atom, a C1-C4 alkyl group, a group C1-C4 haloalkyl, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, an alkylsulfinyl group of C1-C3, a haloalkylsulfinyl group of C1-C3, a alkylsulfonyl group of C1-C3, a haloalkylsulfonyl group of C1-C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group); and Q2 is represented by the general formula (2), wherein, in the formula, Yi represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a fluorine atom, a chlorine atom, an iodine atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a group C 1 -C 3 alkylthio, a C 1 -C 3 haloalkylthio group, a C 1 -C 3 alkylsulfinyl group, a C 1 -C 3 haloalkylsulfinyl group, a C 1 -C 3 alkylsulfonyl group, a C 1 -C 3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; 10. A compound as described in claim 1 or 2, represented by the general formula (1a), wherein Ai, A2, A3 and A in the general formula (1), are all carbon atoms wherein, in the formula, Ri and R2 are each independently a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group; G-i and G2 are each independently an oxygen atom or a sulfur atom; Xi, X2, X3, and X4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; Qi is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (substituents are selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkenyl group, a C 2 -C 4 haloalkenyl group, a C 2 -C 4 alkynyl group, a C 2 -C 4 haloalkynyl group, a group C3-C6 cycloalkyl, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, an alkylamino group of C1 -C4, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, a group acetylamino and a phenyl group), a heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group , an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group having one or more substituents which can be the same or different (the substituents are selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkenyl group, a C 2 -C 4 haloalkenyl group, a C 2 -C 4 alkynyl group, a C 2 -C 4 haloalkynyl group, a group C3-C6 cycloalkyl, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, an alkylsulfinyl group of C1-C3, a haloalkylsulfinyl group of C1-C3, an alkylsulfonyl group of C1-C3, a haloalkylsulfonyl group of C1-C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group, (The heterocyclic group represents the same to those described above); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, Yi represents a haloalkylthio group of C1-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group C4, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; or wherein, in the formula, Y6 and Yg each independently represent a halogen atom, an alkyl group of C1-C4, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1- C3 alkylsulfinyl group C3, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkylthio group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulfonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Y9 must represent a haloalkylthio group of C2-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3). 11. The compound as described in the claim 10, characterized in that Q1 represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a haloalkyl group of C1-C4, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3 halocycloalkyl group -C6, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group , a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamic group ino and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (substituents are selected from a halogen atom, a C1-C4 alkyl group), a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a haloalkylsulfinyl group of C1-C3, an alkylsulfonyl group of C1-C3, a haloalkylsulfonyl group of C1-C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group); and Q2 is represented by the general formula (2), wherein, in the formula, Yi represents a haloalkyl group of C2-C3, a haloalkylsulfinyl group of C1-C3 or a haloalkylsulfonyl group of C1-C3; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a haloalkyl group of C1-C4, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a haloalkylsulfinyl group of C1 -C3, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. 12. The compound as described in the claim 1, represented by the general formula (1), wherein, in the formula, A ,, A2, A3 and A each independently represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom; wherein, any of Ri and R2 is a hydrogen atom, the other is a C1-C6 alkyl group or a C1-C4 alkylcarbonyl group, or both of Ri and R2 are C1-C4 alkyl groups or alkylcarbonyl groups of C1-C4. G1 and G2 are each independently an oxygen atom or a sulfur atom, Xs are each independently a hydrogen atom, a halogen atom, or a trifluoromethyl group; n represents an integer from 0 to 4; Qi is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group , a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, an alkylsulfonyl group of C1-C3, a haloalkylsulfonyl group of C1-C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, an alkylcarbonyl group of C1-C4, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a group Heterocyclic (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, a group oxazolyl, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group , a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group , an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described previously); and Q2 is represented by the general formula (2) or (3), wherein, in the formula, Yi represents a C 1 -C 4 alkoxy group or a C 1 -C 4 haloalkoxy group; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group of C1-C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; wherein, in the formula, Y6 and Y9 each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group , an alkylthio group of C1-C3, a haloalkyl group of C1-C3, an alkylsulfinyl group of C1-C3, a haloalkylsulfinyl group of C1-C3, a group C 1 -C 3 alkylsulfonyl, a C 1 -C 3 haloalkylsulfonyl group or a cyano group; Y8 represents a haloalkoxy group of C 1 -C 4, a perfluoroalkyl group of C 2 -C 6, a perfluoroalkylthio group of C 1 -C 6, a perfluoroalkylsulfinyl group of C 1 -C 6 or a perfluoroalkylsulfonyl group of C 1 -C 6; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (In the present invention, at least one of Y6 and Yg must represent a C1-C4 alkoxy group or a C1-C4 haloalkoxy group. ). The compound as described in claim 12, represented by the general formula (1a), wherein A ,, A2, A3 and A in the general formula (1), are all carbon atoms wherein, in the formula, any of RT and R2 is a hydrogen atom, the other is a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group, or both of Ri and R2 are C1-C4 alkyl groups or C1-C4 alkylcarbonyl groups; GT and G2 are each independently an oxygen atom or a sulfur atom; Xi, X2, X3, and X4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group; QT is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group , a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, an alkylsulfonyl group of C1-C3, a haloalkylsulfonyl group of C1-C3, an amino group, an alkylamino group of C1-C4, a di-alkylamino group of C1-C4, a cyano group, a nitro group, a hydroxy group, an alkylcarbonyl group of C1-C4, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a group heterocyclic group (The heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a group tetrazolyl), or a substituted heterocyclic group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group , a C 1 -C 4 alkylamino group, a C 1 -C 4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C 1 -C 4 alkylcarbonyl group, a C 1 -C 4 alkylcarbonyloxy group, an alkoxycarbonyl group of C1-C4, an acetylamino group and a phenyl group, (The heterocyclic group represents the same as those described above); and Q2 is represented by the general formula (2), where, in the formula, Yi represents a haloalkoxy group of C1-C4; Y 5 represents a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 3 alkylthio group, a haloalkylthio group of C1-C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a perfluoroalkyl group of C2-C6, a perfluoroalkylthio group of C1-C6, a perfluoroalkylsulfinyl group of C1-C6 or a perfluoroalkylsulfonyl group of C1-C6; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. The compound as described in claim 13, characterized in that QT represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkenyl group, a C 2 -C 4 haloalkenyl group, a C 2 -C 4 alkynyl group, a C 2 -C 4 haloalkynyl group, a group C3-C6 cycloalkyl, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, an alkylsulfinyl group of C1-C3, a haloalkylsulfinyl group of C1-C3, a group alkylsulfonyl of C1-C3, a group C1-C3 haloalkylsulfonyl, an amino group, a C1-C4 alkylamino group, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, an alkylcarbonyloxy group of C1-C4, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different (substituents are selected of a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a haloalkynyl group of C2-C4, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1- C3 haloalkyl group C3, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a haloalkyl group C1-C3-ilsulfonyl, an amino group, a C1-C4 alkylamino group, a C1-C4 di-alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, an alkylcarbonyloxy group of C1-C4, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group). 15. A compound represented by the general formula (4), (4) and ~ Q2a wherein, in the formula, R 2 represents a hydrogen atom, a C 1 -C 4 group or a C 1 -C 4 alkylcarbonyl group; and Q2a is represented by the general formula (2), (3) or (5), wherein, in the formula, YI represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5 represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; wherein, in the formula, Y6 and Yg, each independently represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, C1-C4 alkoxy, a C1-C4 haloalkoxy group, a C1- C3 alkylthio, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group, a C1-C3 haloalkylsulfinyl group; a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group, and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (in the present invention, at least one of Y6 and Yg must represent a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, or a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group); or wherein, in the formula, Ra and Rb each independently represents a fluorine atom, or a C1-C4 group perfluoroalkyl; Rc is a hydroxy group, -O-Rd (Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arisulphonyl group, a C1-C4 group alkylcarbonyl or a C1-C4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom; Y? A represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Ysa represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1 group -C3 haloalkylthio, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; and Y2a and Y4a each independently represent a hydrogen atom, a halogen atom, or a C1-C4 alkyl group. 16. A compound represented by the general formula (7), wherein, in the formula, Ai, A2, A3 and A each independently represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom; R 2 represents a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkylcarbonyl group; G2 represents an oxygen atom or a sulfur atom; X represents a hydrogen atom, a halogen atom, or a trifluoromethyl group; n represents an integer from 0 to 4; and Q2a is represented by the general formula (2), (3) or (5), wherein, in the formula, Yi represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5 represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group; wherein, in the formula, Y6 and Y7 each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1 group -C3 alkylthio, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a group C1-C4 haloalkoxy, a C2-C6 perfluoroalkyl group, a group C1-C6 perfluoroalkylthio, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y7 represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group (in the present invention, at least one of Y6 and Y9 must represent a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a group C1-C3 haloalkylthio, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group); or wherein, in the formula, Ra and Rb are each independently a fluorine atom or a C1-C4 perfluoroalkyl group; Rc is a hydroxy group, -O-Rd (Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an aryisulfonyl group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group), an chlorine, a bromine atom or an iodine atom; Y? A represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5a represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1 group -C3 haloalkylthio, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; and Y2a and Y4a each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. 17. A compound represented by the general formula (9), wherein, in the formula A1t A2, A and A each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom; RT and R2 each independently represent a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group; G2 is an oxygen atom or a sulfur atom; X represents a hydrogen atom, a halogen atom or a trifluoromethyl group; n represents an integer from 0 to 4; and Q2a is represented by the general formula (2), (3) or (5), wherein, in the formula, YT represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 each independently represent a hydrogen atom, an atom of halogen or a C1-C4 alkyl group; wherein, in the formula, Ye and Y9 each independently represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1 group -C3 alkylthio, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group (in the present invention, at least one of Ye and Y9 must represent a C1-C4 alkoxy, C1-C4 haloalkoxy, a C1- C3 haloalkylthio, a haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group); or wherein, in the formula, Ra and Rb are each independently a fluorine atom or a C1-C4 group perfluoroalkyl; Rc is a hydroxy group, -O-Rd (Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arisulphonyl group, a C1-C4 group alkylcarbonyl or a C1-C4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom; Y1a represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5a represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1 group -C3 haloalkylthio, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; and Y2a and Y a each independently represent a hydrogen atom, a halogen atom, or a C1-C4 alkyl group. 18. A compound represented by the general formula (10), where, in the formula A ,, A2, A3 and A4 represent each independently a carbon atom, a nitrogen atom or an oxidized nitrogen atom; RT and R2 each independently represent a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group; d and G2 each independently represent an oxygen atom or a sulfur atom; X is a hydrogen atom, a halogen atom or a trifluoromethyl group; n represents an integer from 0 to 4; QT is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a group C2-C4 alkenyl, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1 group -C3 haloalkoxy, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a group C1-C4 alkylamino, a C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1- C4 alkoxycarbonyl, an acetylamino group and a phenyl group), a heterocyclic group (the heterocyclic group in the present invention represents a pyridyl group, a pyridine N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a group furyl, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group), or a group substituted heterocyclic having one or more substituents which may be the same or different (the substituents are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a group C2-C4 haloalkenyl, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1 group -C3 alkylthio, a g C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an amino group, a C1-C4 alkylamino group, a C1- C3- C4 alkylamino, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group), (the heterocyclic group represents the same to those described previously); and Q2b is represented by the general formula (5), wherein, in the formula, Ra and Rb are each independently a fluorine atom or a C1-C4 perfluoroalkyl group; Rc is hydroxy group, -O-Rd (R <1 represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an aryisulfonyl group, a C1 group -C4 alkylcarbonyl or a C1-C4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom; Y? A represents a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 haloalkylthio group, a C1-C3 haloalkylsulfinyl group or a C1-C3 haloalkylsulfonyl group; Y5a represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1 group -C3 haloalkylthio, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; and Y2a and Y4a each independently represent a hydrogen atom, a halogen atom, or a C1-C4 alkyl group. 19. An insecticide comprising the compound as described in any one of claims 1 to 14, in the form of an active ingredient. 20. A method for the application of a chemical, wherein the method comprises applying an effective amount of the compound as described in any of claims 1 to 14 in crops or useful soil for the purpose of protecting useful crops. against dangerous organisms.
MX2007016241A 2005-06-23 2006-06-20 Amide derivative, pesticide containing such compound and use thereof. MX2007016241A (en)

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