JPH04120007A - Insecticide composition - Google Patents

Abstract

PURPOSE:To obtain a insecticide composition containing a guanidine derivative and benzoylurea based insecticide, etc., capable of providing synergic excellent insecticidal effect, having excellent fast-acting property and residual activity and capable of sufficiently satisfying even in toxic aspects. CONSTITUTION:The aimed insecticide composition containing at least one kind of substance selected from (A) a compound expressed by the formula (R<1> is homocyclic or heterocyclic group which may be substituted; n is 0 or 1; R<2> is H or hydrocarbon which may be substituted; R<3> is primary or tertiary amino; X is electron-attracting group, provided that R<1> is a group except halogen pyridyl when X is CN and R<1> is heterocyclic group which may be substituted, when n is 0) or salt thereof, e.g. 3-(2-chloro-5-pyridylmethyl)-1-methyl-2- nitroguanidine) and (B) benzoylurea based insecticide (e.g. diflubenzuron), nereistoxin derivative or salt thereof (e.g. cartap), thiadiazine derivative or salt thereof (e.g. buprofezin) at a ratio of the ingredient B of 0.1-20 pts.wt., preferably 0.5-10 pts.wt. based on 1 pts.wt. ingredient A.

Description

DETAILED DESCRIPTION OF THE INVENTION (a) Field of Industrial Application The present invention relates to a novel insecticidal composition that exhibits excellent insecticidal activity.

(b) Prior Art Various insecticides have been developed, including phosphorus, carbamate, and pyrethroid insecticides, and have been used as single agents or as mixtures. However, conventional insecticides lack the balance of insecticidal activity at each developmental stage of insect pests, immediate effect, residual effect, systemic transfer, etc., and even though they have excellent insecticidal effects, they are toxic to fish and Alternatively, due to safety issues against useful insects and natural enemies, and chemical damage to crops, the situations and number of uses are limited, and as a result, it cannot be said that a satisfactory insecticidal effect is achieved. In particular, pests whose susceptibility to various conventional chemicals has recently decreased, such as leafhoppers and planthoppers that are resistant to organic phosphorus agents and carbamate agents in rice cultivation in Japan, spider mites and aphid insects in various horticultural crops, The southern yellow thrips on vegetables, the diamondback moth on cruciferous vegetables, and the polerum on cotton have appeared, and there is a strong demand for the establishment of control techniques for these pests.

Furthermore, in recent years, there has been a strong demand for so-called cost reduction in the control of these pathogenic insects, and it is necessary to achieve high control effects with fewer treatments and lower doses of chemicals, and there is a need for the development of drugs that can meet these demands. There is.

(c) Problems to be Solved by the Invention However, the effects of insecticidal compounds as described above are not necessarily satisfactory, especially when the concentration is low.

On the other hand, the present inventor has discovered a guanidine derivative or its salt effective as an insecticide (Japanese Patent Application No. 63-332192), and while considering more effective use of this guanidine derivative, various insecticides have been developed. We investigated the combination of the two and attempted to find a new, unprecedented insecticidal composition that provides a cooperative and excellent insecticidal effect that cannot be obtained by using either alone, and that is fully satisfactory in terms of toxicity.

(d) Means for Solving the Problems According to the present invention, the formula: %Formula% [] [wherein R1 is an optionally substituted homologous or heterocyclic group, n is O or 1, R2 represents hydrogen or an optionally substituted hydrocarbon group, R3 represents a secondary, secondary or tertiary amino group, and X represents an electron-withdrawing group. However, when X is a cyan group, R1 represents an optionally substituted homocyclic or heterocyclic group excluding a pyridyl group, and when n is O, R1 represents an optionally substituted heterocyclic group. . ] at least one of the guanidine derivatives and salts thereof, benzoylurea insecticides, neraistoxin derivatives, salts thereof,
Provided is an insecticidal composition containing at least one selected from thiadiazine derivatives or salts thereof.

The insecticidal activity and/or fungicidal activity of the insecticidal composition of the present invention is as follows:
Unexpectedly, the active compounds are clearly more effective than the sum of their individual effects (both active compounds exhibit a synergistic effect), and have excellent immediate and residual effects.

In particular, the insecticidal composition according to the present invention can be applied for the purpose of controlling pests of agricultural and horticultural crops, such as the diamondback moth larva, which is a lepidopteran pest of cruciferous vegetables, and Abrams 7, which is a hemiptera pest. For example, against the southern yellow thrips, which is a difficult-to-control pest of fruits and vegetables, against the planthopter, a hemiptera pest (e.g., brown planthopper), which is an important pest of rice, and against the lepidopteran pest, the brown borer moth. The active compounds exhibit synergistic and synergistic insecticidal effects at lower concentrations than when each active compound is used alone, and exhibit excellent immediate and residual effects.

In the above formula, R1 represents an optionally substituted homocyclic or heterocyclic group. However, when X is a cyan group, R1 is an optionally substituted homocyclic or heterocyclic group other than a pyridyl group, preferably a pyridyl group or a halogenothiazolyl group, more preferably a halogenothiazolyl group. Indicates the group. The homo- or heterocyclic group represented by R1 is a cyclic group containing only the same atoms or a cyclic group containing two or more different atoms, and means a cyclic hydrocarbon group or a heterocyclic group. Examples of the cyclic hydrocarbon group represented by R1 include C3-8 cycloalkyl groups such as cyclopropylene, cyclobutylene, cyclopentyl, and cyclohexyl;
For example, cyclopropenyl, 1-cyclopentenyl, l
-nclohexenyl, 2-nclohexenyl. 1.4-
C3-@/chloroalkenyl groups such as cyclohexagenyl, e.g. phenyl, 1- or 2-naphthyl, l-,
CS-+4 aryl groups such as 2- or 9-anthryl, 1-, 2-, 3-, 4- or 9-phenanthryl, 1-, 2-, 4-, 5- or 6-azulenyl, etc. are used. Preferred cyclic hydrocarbon groups are, for example, aromatic ones, such as C, - such as phenyl, aR such as aryl groups, etc.
The heterocyclic group represented by ' is, for example, a 5- to 5- to
An 8-membered ring group or a condensed ring group thereof is used, and specific examples thereof include 2- or 3-thienyl, 2- or 3-furyl, 2- or 3-pyrrolyl, 2-3- or 4-pyridyl. , 2-. 4- or 5-oxasilyl, 2-. 4- or 5-thiazolyl.

3-94- or 5-pyrazolyl, 2-. 4- or 5
-imidazolyl, 3-. 4- or 5-ynoxacylyl, 3-. 4- or 5-inchazolyl, 3- or 5-(1,2,4-oxadiazolyl), 1,3.4-
Oxadiazolyl, 3-or 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4- or 5-(1,2,3-thiadiazolyl), 1,2,5-
Thiadiazolyl.

1.2.34 riazolyl, 1,2.4-triazolyl,
IH- or 2H-tetrazolyl, N-oxide-2-
23- or 4-pyridyl, 2-, 4- or 5-pyrimidinyl, N-oxido-24- or 5-pyrimidinyl, 3- or 4-pyridazinyl, pyrazinyl, N-
Oxide-3- or 4-pyridazinyl, benzofuryl, benzothiazolyl, benzoxacylyl, triazinyl.

Oxotriazinyl, tetrasilo N, 5-b]pyridazinyl, triazolo[4,5-b]pyridazinyl, oxoimidazinyl, dioxotriazinyl.

Pyrrolidinyl, piperidinyl, pyranyl, thiopyranyl, l,4-oxazinyl, morpholinyl.

1.4-thiazinyl, 1.3-thiazinyl, piperazinyl, benzimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, intridinyl, quinolidinyl, 1,8-naphthyridinyl, furinyl, phteridinyl, dibenzofuranyl, carbazolyl.

Acridinyl, phenanthridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, etc. are used.

Preferred heterocyclic groups are, for example, 2-13- or 4-pyridyl, 2-. 5 such as 4- or 5-thiazolyl
= or a 6-substituted nitrogen heterocyclic group. These homologous or heterocyclic groups represented by R1 may have 1 to 5 (preferably 1) substituents that are the same or different, and examples of such substituents include methinoethyl, propyl,
Isopropyl, butyl, isobutyl, S-butyl, t-
7' Pentyl, hekinru, heptyl, octyl,
Nonyl, allyl, undenle, dodenle, tridecyl,
Alkyl groups having 1 to 15 carbon atoms such as tetradecyl and pentadecyl; cycloalkyl groups having 3 to 10 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, such as vinyl, alino, 2-methylallyl, 2-butenyl, 3- Alkenyl groups having 2 to 10 carbon atoms such as butenyl and 3-octenyl, such as 2 to 10 carbon atoms such as ethynyl, 2-propynyl, and 3-hexynyl.
Alkynyl groups such as cyclopropenyl, cycloalkenyl groups having 3 to 10 carbon atoms such as cyclopentenyl and cyclohexenyl, aryl groups having 6 to 10 carbon atoms such as phenyl and naphthyl, carbon atoms such as benzyl and phenylethyl. Aralkyl group of number 7 to 1O, nitro,
hydroxyl group.

Mercapto, oxo, thioxo, cyano, carbamoyl, carboxyl, C1□alcoquine carbonyl such as methoxycarbonyl, ethoxycarbonyl, sulfo, halogen such as fluorine, chlorine, bromine, iodine,
For example, C1-6 alkoxy such as metquin, ethoxy, propoxy, impropoxy, butoxy, imbutoxy, S-butquin, t-butquin, c5-to aryloxy such as fenoquine, e.g. methylthio,
Ethylthio, n-propylthio, isopropylthio, n
01-M alkylthio such as -butylthio, L-butylthio, 06-1° arylthio such as phenylthio, 01□alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, c, -1° aryl 7 such as phenylsulfinyl, etc. , L-finyl, 01- such as methylsulfonyl, ethylsulfonyl, etc.
Alkylsulfonyl, e.g. c, -1°arylsulfonyl such as phenylsulfonyl, amino, e.g. 02-6 acylamino such as acetylamino, propionylamino, e.g. methylamino, ethylamino, n-propylamine, isopropylamino, n-butyl amino,
Mono- or di-C1 such as dimethylamino and diethylamino
-6 alkylamino, for example 03-6-chloroalkylamino such as cyclohexyl amino, c5-to arylamino such as anilino, C2- such as acetyl, C,- such as aryl, such as benzoyl.

Aryl-carbonyl, such as 2- or 3-thienyl, 2- or 3-furyl, 3-14- or 5-pyrazolyl, 24- or 5-thiazolyl 1.3-14- or 5-isothiazolyl, 2-14- or 5 -oxazolyl, 3-14- or 5-isoxasilyL.

2-14- or 5-imidazolyl, 1.2.3- or 1,2.4-triazolyl, IH or 2H tetrasily”% 2% 3- or 4-pyridyl, 2-
5- to 6-membered heteroatoms containing 1 to 4 beta atoms selected from oxygen, sulfur, and nitrogen, such as 14-mani 5-hyrimidinyl, 3-malko 4-pyridanidyl, quinolyl, isoquinolyl, indolyl, etc. One to five ring groups are used. These substituents are, for example, CM-10 aryl,
C,-,. Aralkyl, C3-IQ-chloroalkyl, C
,,. cycloalganyl, C6-1゜aryloki7,
C6-,. In the case of arylthio, C, -1゜arylsulfinyl, CM-1゜arylsulfonyl, C6-10 arylamino, heterocyclic group, etc., the above-mentioned halogen, hydroxyl group, such as methyl, ethyl, propyl, isopropyl, C1 □ Alkyno such as isobutyl, S-butyl, 1-butyl, etc., vinyl,
C2-4 alkenyl such as allyl, 2-methylallyl, C2-1 alkynyl such as ethynyl, 2-propynyl, etc. 5-to aryl, C1□ alkoxy, phenoxy, C1-4 alkylthio, phenylthio, etc. 1 to 5
may be substituted, and the substituent is C1-15 alkynyl, C2-1o alkenyl, C2-10 alkynyl,
C,6 alkoxy, C,-6 alkylthio, C1-4 alkylsulfinyl, C3-4 alkylsulfonyl, amino, mono- or di-C1-, alkylamino, C,,
In the case of cycloalkylamino, C,-, oarylamino, etc., the above-mentioned halogen, hydroxyl group, C
1 to 5 may be substituted with 1□alkoxo, C1-4 alkylthio, or the like.

A preferred example of R1 is a 5- or 6-membered nitrogen-containing heterocycle such as pyridyl or thiazolyl which may be substituted with 1 or 2 halogens.

n represents 0 or l, preferably l.

The hydrocarbon group of the "optionally substituted hydrocarbon group" represented by R2 includes the aforementioned alkyl group having 1 to 15 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, and cycloalkyl group having 2 to 10 carbon atoms. alkenyl group, alkynyl group having 2 to 10 carbon atoms, /chloroalkenyl group having 3 to 10 carbon atoms, 6 carbon atoms
An aryl group having 10 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, and the like are used. Further, as the substituent for the "optionally substituted hydrocarbon group", those mentioned above as the substituent for the isocyclic or heterocyclic group represented by R1 can be used.

Preferred examples of R2 are, for example, hydrogen, such as methyl,
It is an alkyl group such as ethinopropyl.

R3 represents a primary, secondary or tertiary amino group, and! For example, the formula [wherein R12 and R13 are the same or different and represent hydrogen or an optionally substituted hydrocarbon group, or R1
2 and R13 together represent a cyclic amine group with the adjacent nitrogen. ] (Here, the primary amino group is l: For example, in the above formula, R1
2 and R13 are hydrogen, a tertiary amino group is a monosubstituted amine group where either R12 or R'' is hydrogen, and a tertiary amino group is a monosubstituted amine group where either R12 or R13 is hydrogen. (means a di-substituted amine group). "Optionally substituted hydrocarbon group" represented by R12 and RI3
For example, the one described in R2 above is used. Examples of the cyclic amino group in which R'' and RI3 together represent an adjacent nitrogen include acyridino, azatidino, pyrrolidino, and morpholino.

A thiomorpholino group or the like is used. Preferred examples of R3 include unsubstituted amino groups, such as mono-〇, -4 alkylamino groups such as methylamine, ethylamino and propylamino, di-01□ alkylamino groups such as dimethylamine and ethylmethylamino, e.g. 0 of formamide, N-methylformamide, acetamide, etc.
1-4 acylamino group, etc.

Examples of the electron-withdrawing group represented by X include cyano, nitro, alkoxycarbonyl (for example, 01-4 alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, etc.), hydroxycarbonyl, and C6-□. Aryloxycarbonyl (for example, phenoxycarbonyl, etc.), heterocyclic oxycarbonyl (the heterocyclic group mentioned above for R1 is used, for example, biridyloxycarbonyl, etc.), halogen (CQ, Br, etc.) C1□alkylsulfonyl (e.g., methylsulfonyl, trifluoromethylsulfonyl, ethylsulfonyl, etc.), sulfamoyl, di-C1□alkoxyphosphoryl (e.g., jetoxyphosphoryl, etc.), which may be substituted with, for example, halogen CCQ, Br , F, etc.), etc.)
1-, acyl (eg acetyl, trichloroacetyl, trifluoroacetyl, etc.), C,-. Aryl-carbonyl (e.g. benzoyl etc.), carbamoyl, C
l-4 alkylsulfonylthiocarbamoyl (for example, methylsulfonylthiocarbamoyl, etc.) and the like are used. Preferred electron-withdrawing groups include, for example, nitro.

Preferred examples of the guanidine derivative [I] or a salt thereof include, for example, in the R5. , a methyl group, an ethyl group, a formyl group, or an acetyl group, or a salt thereof.In the formula [■°1, Rla represents a 3-pyridyl group, for example, 6-chloro-
a halogenopyridyl group such as 3-pyridyl, 6-bromo-3-pyridyl, 5-bromo-3-pyridyl, or 2-
It represents halogenothiazolyl groups such as chloro-5-thiazolyl and 2-bromo-5-thiazolyl.

Specific examples of such compounds [1] or salts thereof include 3-(2-chloro-5-pyridylmethyl)-1
-Methyl-2-nitroguanidine, 3-(2-chloro-
Examples include 5-thiazolylmethyl)-1-methyl-2-nitroguanidine and 3-(2-chloro-5-thiazolylmethyl)-1,1-dimethyl-2-nitroguanidine.

The guanidine derivative [1] or a salt thereof gives rise to cis and trans stereoisomers with respect to the X position, and theoretically tautomerism occurs when R2 is hydrogen and R3 is a th- or th-amino group. However, any of these isomers is included in the compound [I] of the present invention or a salt thereof.

Further, examples of the salt of the guanidine derivative [I] include hydrochloric acid, hydrobromic acid, hydroiodic acid, and phosphoric acid.

Inorganic acids such as sulfuric acid, perchloric acid, for example formic acid, acetic acid.

Salts with organic acids such as tartaric acid, malic acid, citric acid, succinic acid, benzoic acid, picric acid, p-toluenesulfonic acid may be used.

Formula [1] used in the active substance combination according to the invention
] Table 1 shows representative compounds of guanidine derivatives.
Examples include the compounds listed above.

The method for producing the guanidine derivative or its salt is described, for example, in Japanese Patent Application No. 63-332192 and EP-376279.

Furthermore, examples of the benzoylurea insecticide used in the insecticidal composition of the present invention include the formula: [wherein R4 and R5 represent an optionally substituted phenyl group. ] Compounds represented by the following are used. Examples of substituents for the "optionally substituted phenyl group" of R4 and R5 in formula [I[] include halogens such as fluorine, chlorine, bromine, and iodine, C1□ alkyls such as methyl and ethyl, e.g. Halogen C1-6 alkyl substituted with 1 to 6 halogens such as fluorine, chlorine, bromine, and iodine, such as fluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, tetrafluoroethyl, and dibromopropyl, such as difluoromethoxy, fluoromethoxy,
Halogen C, alkoxy substituted with 1 to 6 halogens such as trichloromethoxy, tetrafluoroethoxy, iodobutoxy, etc., chlorine, bromine, iodine, etc., such as chloromethoxythio, trifluoroethylthio, tetra Halogen C3-, alkylthio, etc. substituted with 1 to 6 halogens such as fluorine, chlorine, bromine, and iodine, such as chloro-1-propylthio and l-chloro1-fluoro-2-difluoro-ethylthio, are used. .

Substituents for the "optionally substituted phenyl group" of R' and R5 include, for example, ca- such as phenyl.
to aryl, such as fluorophenyl, chlorophenyl, difluorophenyl, dichlorophenyl, bromophenyl, trifluorophenyl, trichlorophenoxy 3,5-dichloro-phenyl, etc. Chlorine, bromine,
Halogenophenyl substituted with 1 to 5 halogens such as iodine, such as fluoromethyl-phenyl, dichloromethyl-phenyl, trifluoromethyl-phenyl, trichloromethyl-phenyl, etc., halogen C3-, alkyl substituted with 1 to 5 ta 1 by nitro such as halogeno C1-4 alkyl phenyl, e.g. evanitrophenyl, etc.
to 3-substituted phenyl, e.g. 2-chloro-4
Substituted with 1 to 5 halogens such as fluorine, chlorine, bromine, iodine, etc., such as trifluoromethyl phenyl, 3-trifluoromethyl-4-chloro-phenyl, and halogeno C1-4 alkyl such as trifluoromethyl, trichloromethyl, etc. phenyl etc. are used.

Examples of substituents for the "optionally substituted phenyl group" of R' and R' include C, -, such as fenoquine, etc.
. Aryloxy, such as chlorophenoxy, fluorophenoxy, difluorophenoxy, dichlorophenoquine, bromophenoxy/, trifluorophenoxy, trichlorophenoxy, fluorine, chlorine, bromine, iodine, etc. Phenoxy substituted with 1 to 6 halogens such as halogen C such as chloroethyl-phenoxy, trifluoromethyl-phenoquine, trichloromethyl-phenoxy, etc.
1-, halogeno C1 substituted with 1 to 5 alkyl groups
-, alkylphenoxy, for example phenoxy substituted with 1 to 3 nitro such as nitrophenoxy, for example 2-chloro-4 trifluoromethyl-phenoxy,
Also used are fluorine such as 3-trichloromethyl-4-fluoro-phenoxy, halogen such as salts, and phenoxy substituted with 1 to 5 halogeno C1-4 alkylphenoxy such as trifluoromethyl and trifluoroethyl.

Examples of substituents for the "optionally substituted phenyl group" of R4 and R5 include, for example, 2-chloro-4-
77 atoms such as trifluoromethyl-pyridyloxy, halogens such as chlorine, bromine, and iodine, and halogenated C1□alkyl, etc., which may be substituted with 1 to 4 same or different atoms, for example, 1 to 5 nitrogen atoms. have 5
or 6-membered heteroaryloxy, etc. may also be used.

"Optionally substituted 7 enyl group" of R4 and R''
Preferred examples of substituents include halogens such as fluorine and chlorine, 01-2 alkyl such as methyl, halogen C+-a alkyl substituted with 1 to 3 halogens such as fluorine such as trifluoromethyl, Halogeno C1-, alkoxy substituted with 1 to 4 halogens such as fluorine, chlorine, bromine, iodine, etc., e.g., trifluoromethoxy, trichloromethoxy, tetrafluoroethoxy, etc., e.g. l-chloro-1-fluoro-2difluoro-ethylthio Halogeno C1- substituted with 1 to 4 halogens such as fluorine, chlorine, bromine, iodine, etc., alkylthio, such as phenyl, such as fluorophenyl, chlorophenyl, difluorophenyl, dichlorophenyl, 2,4-difluoro-3,5- Halogenophenyl substituted with 1 to 4 halogens such as fluorine or chlorine such as dichloro-phenyl, halogenophenyl substituted with 1 to 3 halogenoCl-2 alkyl such as trifluoromethyl-phenyl, alkylphenyl, nitro Phenyl substituted with fluorine such as phenoxy, tif 2-chloro-4-fluoromethyl-phenyl, halogen such as chlorine, and halogeno C1 such as fluoromethyl, alkyl,
For example, phenoxy, such as fluorophenoxy, chlorophenoxy, difluorophenoxy, dichlorophenoxy, 2,4-difluoro-3,S-dichloro-phenoxy, etc., halogenophenoxy substituted with 1 to 3 halogens such as fluorine, chlorine, etc. Fluoromethyl-
Halogeno C1-2 alkyl such as phenoxy, 1 to 3
Halogens such as fluorine, chlorine, etc., such as 2-chloro-4-trifluoromethyl-phenoxy, nitrophenoxy, 2-chloro-4-trifluoromethyl-phenoxy, and halogens C1-2 alkyl, such as trifluoromethyl, substituted with 5-substituted phenoxy, for example, fluorine such as 2-chloro-4-trifluoromethyl-pyridyloxy7, halogen such as chlorine, and halogenated C3-2 alkyl, etc., substituted with 1 or 2 of the same or different For example, a 6-membered heteroaryloxy having 1 or 2 nitrogen atoms may be used.

Preferred examples of R4 include phenyl, chlorophenyl, dichlorophenyl, 2,4-difluoro-3,
Halogenophenyl substituted with 1 to 4 halogens such as fluorine or chlorine such as 5-dichloro-phenyl, phenyl substituted with 1 to 3 halogeno C,-2 alkoxy such as trifluoromethoxy-phenyl, 2-chloro −
Phenyl substituted with 1 to 3 halogens and halogeno C1-2 alkyl such as 4-trifluoromethyl-phenyl, halogens such as 3.5-dichloro-4-tetrafluoroethoxy-phenyl, and 1 substituted with halogeno C1-2 alkoxy or 3 replaced Fenino murmurs 2-(3
phenyl substituted with 1 to 3 halogens and halogeno C1-2 alkylthio such as -chloro-3-fluoro-2-difluoro-ethylthio)-5-fluoro-phenyl, 4-(4nitrophenoxy)-3,5-dichlorophenyl Phenyl substituted with 1 to 4 halogens and nitrophenoxy, such as (2-chloro-4 trifluoromethyl-pyridyloxy)-phenyl, and nitrogen substituted 1 to 3 times with halogen C1-2 alkyl. 6-membered heteroaryl with 1 or 2 1
Alternatively, 2-substituted phenyl or the like is used.

Preferred examples of R5 include, for example, fluorophenyl,
Phenyl substituted with 1 to 4 halogens such as fluorine or chlorine such as chlorophenyl, difluorophenyl, dichlorophenyl, 3-trifluoromethyl-4-chloro-
Halogeno C3-2 alkyl such as phenyl and phenyl substituted with 1 to 4 halogens are used.

Specific examples of the benzoylurea insecticides mentioned above include 1-(4-chlorophenyl-3-(2,6-difluorobenzoyl))ffl (generic name: "diflubenzuron").
：Hereinafter, similarly (indicate the common name of the internal law), 1-(3,
5-dichloro-4-(3-chloro-5trifluoromethyl-2-pyridyloxy)phenyl)-3-(2,6-
difluorobenzoyl)urea (chlorfluazuron), 1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea (teflubenthrone), 1-(4-trifluoro methoxyphenyl)-3(2-
Chlorobenzoyl) urea (triflumuron), 1-(2
-Fluoro-4-(2-chloro-4-trifluoromethylphenoxy)phenyl)-3-(2+6-difluorobenzoyl)urea (fluphenoxyuron), 1-(3,5-dichloro-4-(1,1 ,2,2-tetrafluoroethyl)phenyl)-3-(2,6-difluorobenzoyl)urea, 1-(2-fluoro-4-(2-chloro-1,1゜2-
trifluoroethylthio)phenyl)-3-(2,6-
difluorobenzoyl)urea, etc., preferably 1-(3,5-dichloro-4-(3-chloro-5=trifluoromethyl-2-pyridyloxy)phenyl)-3
-(2,6-difluorobenzoyl)urea and the like are used.

The above-mentioned benzoyl urea insecticide can be produced, for example, by a method similar to that of Japanese Patent Publication No. 182551/1983.

In addition, the insecticidal derivatives used in the insecticidal composition of the present invention include, for example, the formula: [wherein R6 and R7 are an alkyl group, R8 and R9 are a carbamoyl group which may have a substituent or It represents an arylsulfonyl group or is bonded to -5-. ] or a salt thereof is used. Formula [11
Examples of the alkyl groups R6 and R7 in 1] include methyl, ethyl, propyl, 1-propyl, butyl, 1
-butyl, S-butyl, t-butyl, C+-a alkyl such as pentyl and hexyl, and preferably C1- and alkyl such as methyl and ethyl.

The arylsulfonyl group of the [arylsulfonyl group which may have a substituent] for R6 and R9 is,
For example, ca-to arylsulfonyl teary such as phenylsulfonyl and naphthylsulfonyl, preferably phenylsulfonyl and the like are used.

The substituents of R8 and Rg "carbamoyl group, arylsulfonyl group which may have a substituent" are:
For example, halogens such as fluorine, chlorine, bromine, and iodine, 01-6 alkyls such as methyl, ethyl, propyl, 1-propyl, butyl, 01-6 alkoxynes such as methquine, ethoxy, propoxy, 1-propoxy, butoxy, etc. is used. When two or more of these substituents are present, they may be the same or different and may be substituted by 1 to 5, preferably 1 to 3.

R8 and R9 “optionally substituted car/<
Preferred examples of substituents for the "moyl group or arylsulfonyl group" include halogens such as fluorine and chlorine, C1-4 alkyls such as methyl and ethyl, C1- such as methoxy and ethoxy, and alkoxy.

Preferred examples of R8 and R'' include carbamoyl, phenylsulfinyl, etc., or -8- formed by bonding with each other.

Examples of salts of Nereistoxin derivatives include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid, and perchloric acid; for example, formic acid, acetic acid, tartaric acid, malic acid, citric acid, and oxalic acid. Salts with organic acids such as , succinic acid, benzoic acid, and picric acid may also be used.

Specific examples of the above-mentioned nelystoxin derivatives include 1,3-bis-(carbamoylthio)-2-(N.

N-dimethylamino)propane hydrochloride (Cartap), S,S''-2-dimethylaminotrimethylene dibenzene thiosulfonate) (bensultap), 5-dimethylamino-1,2,3-trithianoxalate (thiocyclam), preferably 1,3-bis-(carbamoylthio)-2-(N).

N-dimethylamino)propane hydrochloride, S,S'-2-
Dimethylamino trimethylene di(benzenesulfonate), 5-dimethylamino-1,2,34 lithian oxalic acid, etc. are used.

The above-mentioned Nereistoxin derivative or its salt can be produced, for example, by a method according to Japanese Patent Publication No. 10969/1973.

Further, examples of the thiadiazine derivatives used in the insecticidal composition of the present invention include the formula: [wherein RIO and R□
□ is the same or different and is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an allyl group, a cycloalkyl group having 5 or 6 carbon atoms, a lower alkoxyalkyl group having a total number of 3 to 6 carbon atoms, or a benzyl group , phenyl group or formula: (wherein Y represents a halogen atom, a lower alkoxy group, a trifluoromethyl group, or a lower alkyl group, and Z represents a hydrogen atom, a halogen atom, or a lower alkyl group.)
This shows a substituted phenyl group represented by. A compound represented by 1 or a salt thereof is used. Examples of the alkyl group having 1 to 8 carbon atoms represented by R1° and R11 in formula [IV] include methyl, ethyl, propyl, l-propyl, butyl, i-butyl, S-butyl, t-butyl. ,
0 such as pentyl, l-pentyl, S-pentyl, t-pentyl, hexyl, heptyl, octyl, theo-octyl, etc.
1-8 alkyl, preferably C+-a alkyl such as ethyl, propyl, i-propyl, butyl, i-7'yl, S-butyl, t-butyl, hexyl, octyl, t-octyl, etc. .

The cycloalkyl group having 5 or 6 carbon atoms represented by R" and R" includes, for example, cyclopentyl, cyclohexyl, etc., and preferably, for example, cyclohexyl is used. Examples of the lower alkoxyalkyl group having a total of 3 to 6 carbon atoms represented by R5° and R11 include methoxymethyl, methoxyethoxymethyl, ethoxy-ethyl, propoxy-methyl, propoxy-ethyl, etc. Preferably, the total number of carbon atoms is 3, such as ethoxy-methyl, ethoxy-ethyl, etc.
or a lower alkoxyalkyl group of 4 is used.

Examples of the halogen atoms represented by Y and Z include fluorine, chlorine, bromine, and iodine, and preferably fluorine, chlorine, and the like are used. The lower alkoxy group represented by Y includes, for example, 01- and alkoxy such as methoxy, ethoxy, propoxy, and butoxy, and preferably c + -4 alkoxy such as methoxy. Y
The lower alkyl group represented by and Z includes, for example, 01- and alkyl such as methyl, ethyl, propyl, butyl, and preferably C1□ alkyl such as methyl. Preferred examples of Y include trifluoromethyl and the like in addition to those listed above. A preferable example of Z is
In addition to the above, there are hydrogen atoms and the like. RIO and R1
Preferred examples of 1 include the above-mentioned preferred examples of alkyl groups having 1 to 8 carbon atoms, preferred examples of cycloalkyl groups having 5 or 8 carbon atoms, or lower alkoxyalkyl groups having 3 to 6 carbon atoms in total. Preferred examples of the group include, for example, hydrogen atoms, such as allyl, such as benzyl, such as phenyl, such as halogenophenyl substituted with 1 to 3 fluorine, chlorine, etc., such as chloro-phenyl, fluoro-phenyl, dichloro-phenyl, and methyl. −
01□alkyl such as phenyl, dimethylphenyl, etc.
01□C1-4 alkoxyphenyl substituted with 1 to 3 alkoxy such as C1-, alkylphenyl, methoxy-phenyl substituted with 1 to 3, 2-methyl-4
phenyl substituted with 1 to 4 halogens and c, -, alkyl such as -chloro-phenyl, 2methoxy-5
Phenyl substituted with 1 to 4 halogens, C1-, alkoxy, etc., such as -chloro-phenyl, and the like are used.

Examples of salts of thiadiazine derivatives include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid, and perchloric acid; for example, formic acid, acetic acid, tartaric acid, IJ7 malic acid, citric acid, and Salts with organic acids such as acids, succinic acid, benzoic acid, picric acid, etc. may also be used.

Specific examples of the above-mentioned thiadiazine derivatives include 2-tert-butylimino-3-isopropyl 5-
phenyl-3,4,5,6-tetrahydro-2H-1,
3,5-thiadiazin-4-one (buprofezin), preferably 2-tert-butylimino-3-isopropyl 5-
7enyl-3.4,5.6-tetrahydro-2H-1,
3,5-thiadiazin-4-one and the like are used.

The above-mentioned thiadiazine derivatives or salts thereof can be produced, for example, by a method according to JP-A-54-3083.

The insecticide which is one component of the insecticidal composition of the present invention is already known, for example, the Pesticide Manual (T.
he Pe5ticide Manual 8th edition 19
1987, The Br1tish Crop Pro
It is described as an insecticide in the following publications: Conci 1).

The weight ratios of the active compounds in the insecticidal compositions of the invention are then generally such that: per part by weight of the guanidine derivative or salt thereof of the formula [IJ; or a salt thereof, in an amount of 0.1 to 20 parts by weight, preferably 0.5 to IO parts by weight.

The insecticidal composition of the present invention exhibits excellent insecticidal activity and can be used by spraying on foliage, applying in water or on the surface of water, irrigating the soil surface, mixing with the soil, or treating with seedling boxes.

The insecticidal composition of the present invention exhibits strong insecticidal activity at a lower dose than when each active substance is applied alone, so chemical damage to crops can be completely avoided, and the insecticidal spectrum , insecticidal activity at each developmental stage of pests,
Lack of balance in quick-acting, residual-acting, permeability, etc.
It can also be used in situations where, even if it has an excellent insecticidal effect, its use is limited due to problems such as toxicity to fish, safety against useful insects and natural enemies, and chemical damage to crops.

For example, the insecticidal composition of the present invention may be applied to Nephotettixcin, which is a Hemiptera pest of rice fields.
cticeps), planthoppers (Nil
aparvata lugens), white-legged planthopper (S
ogatellaferucifera), brown-bottomed planthopper (Laodelphaxstriatellus)
) and other Lepidoptera pests such as Chilo 5u
ppressalis), Cnapha
locrocis medinalis), Naranga aenescens, etc., and the rice weevil (Lissorhope), which is a Coleoptera pest.
trus oryzaphilus), rice weevil (
The diamondback moth (P.
lutella maclipennis), Pieris brassicae, Mamestrabrass 1cae, Adoxophy-es sp.
, Caloptilia theivo
ra), aphids (Myzus persicae, Aphisgossyipii, Aphis poni, etc.), scale insects (Unaspicyanoens, etc.) that are Hemiptera pests, such as
is), Pseudococ
cus coms Locki, etc.), whitefly (Trialeurodes vaporarior),
um), Empoasca leafhopper (Empoasca
Scirtothrips dors, which is a pest of the order Thrips, such as
alis), Thrips
The Colorado caterpillar (LepLinotarsa decemlineat), which is a Coleoptera pest, such as
a), Ep i lac
It can be effectively used for controlling insects such as hnavigintioctopunctata).

The insecticidal composition of the present invention can be in the form of a mixed preparation of general agricultural chemicals, such as an emulsion, an aqueous solution, a powder, a granule, a powder, a tablet, an aqueous solution, a flowable agent, a spray, etc. In addition, at the time of use, it is possible to mix the ingredients of at least one compound selected from guanidine derivative [I] or its salt insecticide, benzoyl urea insecticide, nerais toxin derivative, its salt, thiadiazine derivative or its salt. It can be made into a conventional pharmaceutical form such as an emulsion or a wettable powder.

The insecticidal composition of the present invention comprises the above-mentioned guanidine derivative [I] compound or a salt thereof and at least one compound selected from benzoyl urea insecticides, neraistoxin derivatives, salts thereof, thiadiazine derivatives or salts thereof as active ingredients. are dissolved or dispersed in a suitable liquid carrier, alone or in admixture, or mixed with or adsorbed on a suitable solid carrier, and, if necessary, emulsifying agents, suspending agents, spreading agents, etc.
It can be produced by a known method by adding penetrating agents, wetting agents, mucilage agents, stabilizers, etc.

The content of all active ingredients in the insecticidal composition of the present invention varies depending on the purpose of use, but for emulsions, irrigation agents, etc., the appropriate content is about 5 to 70% by weight, and for powders, it is 0.1 to 10% by weight.
The appropriate concentration is 0.5 to 10% by weight for granules, but these concentrations may be changed as appropriate depending on the purpose of use.

When using emulsions, irrigation agents, etc., they are appropriately diluted with water or the like to increase the amount (for example, IOO to 10.000 times) and then sprayed.

Examples of liquid carriers (solvents) used include water, alcohols (e.g., methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol,
ethylene glycol, etc.), ketones (e.g., acetone, methyl ethyl ketone, etc.), ethers (e.g., dioxane, tetrahydro7rane, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc.), aliphatic hydrocarbons (e.g., kerosene, kerosene, etc.) , fuel oil, etc.), aromatic hydrocarbons (e.g., benzene,
Toluene, xylene, solvent naphtha, methylnaphthalene, etc.), halogenated hydrocarbons (e.g., dichloromethane, chloroform, carbon tetrachloride, etc.), acid amides (e.g., dimethylformamide, dimethylacetamide, etc.), esters (e.g., acetic acid) Solvents such as ethyl, butyl acetate, fatty acid glycerin ester, etc.) and nitriles (e.g., acetonitrile, propionitrile, etc.) are suitable, and these can be used as appropriate by mixing one or more of them in an appropriate ratio. be able to.

Solid carriers (diluents and bulking agents) include vegetable powders (e.g., lactose, soybean flour, tobacco powder, wheat flour, wood flour, etc.), mineral powders (e.g., kaolin, bentonite, clays such as acid clay, and talc). , silicas such as mica powder, etc.), diatomaceous earth, calcium carbonate, alumina, sulfur powder, activated carbon, etc., and these can be used alone or in a mixture of two or more in an appropriate ratio.

Surfactants used as emulsifiers, spreaders, penetrants, dispersants, etc. may include soaps, polyoxyethylene alkyl allyl ethers [e.g.
E-Nee (E-A) 142; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.
nonal; manufactured by Toho Chemical Co., Ltd., alkyl sulfates (e.g., Emarl IO, Emarl 40; manufactured by Kao Corporation)],
Alkyl sulfonates [e.g., Neogen, Inogen T: manufactured by Dai-Kogyo Seiyaku Co., Ltd.; Neoperex; manufactured by Ie Co., Ltd.], polyethylene glycol ethers [e.g.,
Noni ball 85, noni pole 100. Nonipole 160
Nonionic and anionic surfactants such as Sanyo Kasei Co., Ltd.] and polyhydric alcohol esters [for example, Tween 20 and Tween 80; manufactured by Kao Corporation] are used as appropriate.

The insecticidal compositions of the present invention, in their commercially useful formulations and the use forms prepared by these formulations, contain other active compounds, such as the aforementioned guanidine derivatives, benzoylurea insecticides, neraistoxin derivatives, its salts, thiadiazine derivatives or insecticides and fungicides other than its salts,
It can also be used as a mixture with acaricides, nematicides, fungicides, and growth regulators.

The thus obtained insecticidal composition of the present invention has extremely low toxicity, is safe, and is an excellent agricultural chemical. The insecticidal composition of the present invention can be used in the same manner as conventional insecticides and acaricides, and as a result, it can exhibit superior effects compared to conventional products.

For example, the insecticidal composition of the present invention can be used against target pests by, for example, spraying on the leaves of a crop treated with a nursery box, spraying insect bodies, applying in water to rice fields, or treating the soil. The amount of application depends on the time of application, location of application,
It can vary widely depending on the method of application etc.
In general, the active ingredient (guanidine derivative [1] or its salt and at least one compound selected from benzoyl urea insecticides, nerais toxin derivatives, its salt, thiadiazine derivative or its salt) per hectare is 0.
．． It is desirable to apply in an amount of 3g to 3000g, preferably 50g to 1000g.

Moreover, when the insecticidal composition of the present invention is an aquarium, it may be diluted and used so that the final concentration of the active ingredient is in the range of 0.1 to 11,000 ppm, preferably 10 to 500 ppm.

(e) Effect test example 1 Test against the Klebian borer moth Solvent: Mixture of acetone (3.5 parts by weight) and dimethylformamide (3.5 parts by weight) 7.0 parts by weight Emulsifier: Polyhydric alcohol ester (Tween 20; Kao (
Co., Ltd.) 2.0 parts by weight 1.0 parts by weight of the active compound mixture or active compound alone listed in the column of test drugs in Table 2 below was mixed with the solvent containing the emulsifier, and the mixture was The hardware was diluted to a predetermined concentration with a spreading agent (Dyne) and tap water for 3000 times.

Test method: Rice plants with a plant height of approximately 30 cm (21 days after transplanting) planted in PVC pots with a diameter of 11.3 CO+ were injected with a water dilution of the active compound at a predetermined concentration prepared as above using a spray gun. After spraying 20 d per pot and air-drying the spray solution, inoculate 10 larvae of the 3rd instar moth per pot, place in a glass constant temperature room at 25 ± 1' c, and examine the surviving overlay after 3 days to determine the insecticidal rate [= ((Number of test animals - Survival overlay) /
number of test animals) x 100] was calculated. The test was conducted in duplicate.

The results are shown below.

(Leaving space below) Table 2 Insecticidal effect on K. bruniscus note N, guanidine derivatives used in this test [I]: Compound No. 1: 3-(2-chloro-5-pyridylmethyl)-1-methyl-2-nitro Guanidine compound No. 2: 3-(2-chloro-5-thiazolylmethyl)l-methyl-2-nitroguanidine compound No. 3: 3-(2-chloro-5-thiazolylmethyl)-1,1-dimethyl-2 -Nitroguanidine 2
, Nereistoxin derivatives [■] used in this test: Compound (A): Cartap compound (B) 2 Bensultap compound (C): Thiocyclam test example 2 Test against brown planthopper Test method: Made of vinyl chloride with a diameter of 11.3 cm Rice plants with a plant height of approximately 30 cm planted in pots (20 days after transplanting) were inoculated with 20 brown planthopper 3rd to 4th instar larvae per pot, and a cylinder made of transparent vinyl chloride film with a diameter of 11 cm and a height of 67 cm was used. (The upper opening was covered with goose)
The next day, using a spray gun, use a spray gun to add an active compound diluted with water at a predetermined concentration, prepared as in Test Example 1, except for using the active compound listed in the test drug column of Table 3 below, or using the active compound alone. It was sprayed from the opening of 1〇- per pot, placed in a glass constant temperature room at 25 ± 1'O, and the surviving overlay was examined after 1 and 5 days to determine the insect killing rate [= ((number of test animals - surviving overlay)] /number of test animals)xlOO] was calculated. The exam is 2
It was done in tandem.

The results are shown below.

Table 3 Insecticidal effect on brown planthopper continued Note) 11 Guanidine derivatives used in this test [■]: Compound No. 1: 3-(2-chloro-5-pyridylmethyl)-1-methyl-2-nitroguanidine Compound No. 2: 3-(2-chloro-5-thiazolylmethyl)-1-methyl-2-nitroguanidine Compound No. 3: 3-(2-chloro-5-thiazolylmethyl)-1,1-dimethyl-2-nitroguanidine 2
, Nereistoxin derivative [DI] and thiadiazine derivative [■] used in this test: Compound (A): Cartap compound (D): Buprofezin Test Example 3 Test method for brown planthopper: Made of vinyl chloride with a diameter of approximately 11.3 cm Rice plants with a plant height of 30 cm planted in pots (20 days after transplanting) were inoculated with 5 mature female brown planthoppers per pot, and rice plants with a diameter of 11
After laying eggs for 2 days by covering them with a cylinder made of transparent vinyl chloride film with a height of 67 cm (the upper opening was covered with goose), the adults were removed and the test chemicals were listed in Table 4 below. A diluted solution of the active compound in water with a predetermined concentration prepared as in Test Example 1 except for using the active compound described above or a single active compound was sprayed from the opening of 1 OIII2 per pot using a spray gun. The pots were placed in a thermostatic glass chamber (C), and the top of each pot was examined 14 days after the chemical treatment, and the index of surviving insects was determined, taking the top of the insect-treated area as 100. The test was conducted in triplicate.

The results are shown below.

Table 4 Insecticidal effect on brown planthopper Note) 19 Guanidine derivatives [I] used in this test: Compound No. 1: 3-(2-chloro-5-pyridylmethyl)-1methyl-2-nitroguanidine Compound No. 2 : 3 (2-chloro-5-thiazolylmethyl)l-methyl-2-nitroguanidine compound No. 3: 3-(2-chloro-5-thiazolylmethyl)1.1-dimethyl-2-nitroguanidine 2,
Nereistoxin derivative [I[] and benzoylurea insecticide [■1] used in this test: Polymerization (A): Cartap compound (D): Buprofezin Test Example 4 Test against diamondback moth Test method: Diameter approx. Radishes with a plant height of 10 cm (21 days after sowing) planted in 3 cm PVC pots were treated with 100 3rd instar diamondback moth larvae per pot, and the active compounds listed in the column of Table 5 below or the active compounds alone were applied. Otherwise, a diluted solution of the active compound in water with a predetermined concentration prepared as in Test Example 1 was added to the pot using a spray gun.
The insecticide rate [-
((Number of test animals - Survival overlay)/Number of test animals)X100] was calculated. The test was conducted in duplicate.

The results are shown below.

Table 5 Insecticidal effect on diamondback moth Note) 19 Guanidine derivatives used in this test [I]: Compound No. 1: 3-(2-chloro-5-pyridylmethyl)-1methyl-2-nitroguanidine Compound No. 2: 3-(2-chloro-5-thiazolylmethyl)=1-methyl-2-nitroguanidine Compound No. 3: 3-(2-chloro-5-thiazolylmethyl)1.1-dimethyl-2-nitroguanidine 21
Nereistoxin derivatives [lIr1 and benzoylurea insecticides [■] used in this test: Compound (A): Cartap compound (E): Chlorfluazuron According to Tables 2.3.4 and 5 above, the present invention It is demonstrated that the insecticidal and fungicidal composition has excellent synergistic insecticidal action and residual efficacy against the brown borer moth, brown planthopper, and diamondback moth compared to the use of each active ingredient alone.

(f) Examples Next, the contents of the present invention will be specifically explained by examples.
The present invention should not be limited to this only.

Example 1 (hydrating powder) 3-(2-chloro-5-pyridylmethyl)-1-methyl-2-nitroguanidine (10% by weight), cartap (
(20% by weight), sodium ligninsulfonate (5% by weight), polyoxyethylene glycol ether (Nonipol 85O: 5t1%), white carbon (10% by weight), clay for wettable powders (50% by weight). They were mixed to produce an irrigation agent.

A 2,000 times diluted solution of this hydrating powder was sprayed at 120 g per 10 a of the field where the Kovno borer moth had begun to attack.
As a result of investigating the damage situation a few days later, the control value in the powder treated area was over 95, which was extremely high.

Example 2 (powder) 3-(2-chloro-5-thiazolylmethyl)-1-methyl-2-nitroguanidine (0,2511% by weight), buprofezin (1,0% by weight), white carbon (5% by weight)
(0% by weight) and clay (93.75% by weight) were thoroughly mixed to produce a powder.

As a result of spraying this powder at a dose of 4 kg per loa to a local field where more than 50 brown planthopper adults and larvae per rice plant were infested, the number of brown planthopper adults and larvae in the powder-treated area rapidly decreased after one application, and the number of brown planthopper adults and larvae in the powder-treated area decreased rapidly for - months. The effect lasted longer.

Example 3 (powder) 3-(2-chloro-5-thiazolylmethyl)-1methyl-2-nitroguanidine (1.0% by weight), cartap (4.0% by weight), dextrin (5.0% by weight) ) and clay (90.0% by weight) were thoroughly pulverized and mixed, a small amount of water was added and the mixture was thoroughly kneaded, followed by extrusion, granulation and drying to produce granules.

As a result of spraying this granule at a dose of 4 kg per 1Oa under flooded conditions to a field where adults and larvae of brown planthoppers and brown borer moths had occurred, the number of adults and larvae of brown brown planthoppers in the powder-treated area rapidly decreased, and the number of brown planthopper adults and larvae in the powder-treated plots decreased rapidly. No progress was observed in the damage caused by the larvae.

(G) Effects of the Invention The present invention contributes to agriculture by providing an excellent insecticide.

Claims (1)

[Claims] Formula: ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 is an optionally substituted homologous or heterocyclic group, n is 0 or 1, R^2 represents hydrogen or an optionally substituted hydrocarbon group, R^3 represents a primary, secondary or tertiary amino group, and X represents an electron-withdrawing group. However, when X is a cyano group, R^1 is an optionally substituted homologous or heterocyclic group other than a halogen pyridyl group, and when n is 0, R^1 is an optionally substituted Indicates a heterocyclic group. ] and at least one selected from benzoyl urea insecticides, neraistoxin derivatives, salts thereof, thiadiazine derivatives or salts thereof. An insecticidal composition.