JP2007186507A - Phthalamide derivative, agricultural and horticultural insecticide and method for using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a phthalamide derivative that exhibits an excellent control effect as an agricultural and horticultural insecticide and performs an excellent control effect by using together with another insecticide, an acaricide, a nematicide, a fungicide, a herbicide, a plant growth regulator, a biological pesticide, etc., and an agricultural and horticultural insecticide comprising the compound as an active ingredient and to provide a method for using the same. <P>SOLUTION: The agricultural and horticultural insecticide comprises the phthalamide derivative represented by general formula (I) �R<SP>1</SP>is an alkyl, an alkenyl, an alkynyl or the like; R<SP>2</SP>and R<SP>3</SP>are each H, an alkyl, an alkenyl, an alkynyl or the like; R<SP>4</SP>and R<SP>5</SP>are each H, an alkyl, an alkenyl, an alkenyl, an alkylcarbonyl, an alkoxycarbonyl or the like; A is a (substituted) tetrazolyl; X and Y are each a halogen, NO<SB>2</SB>, CN, an alkyl, an alkoxy, an alkylthio or the like; m and p are each 0-4; n is 0-2} or its salts as an active ingredient. The method for using the same is provided. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a phthalamide derivative, an agricultural and horticultural insecticide containing the compound as an active ingredient, and a method of using the same.

Conventionally, it is known that certain phthalamide derivatives are useful as agricultural and horticultural insecticides (see, for example, Patent Document 1). Furthermore, it is known that phthalamide derivatives having a skeleton similar to the present invention are useful as agricultural and horticultural insecticides (see, for example, Patent Document 2). However, the compound of the present invention having a tetrazolyl group in its structure is neither described nor suggested.
Japanese Patent Laid-Open No. 11-240857 JP 2001-131141 A

  In crop production such as agriculture and horticulture, damage caused by pests is still large, and development of new agricultural and horticultural insecticides is desired due to factors such as generation of resistant pests against existing drugs. Further, various labor-saving application methods are required due to the aging of farmers, and the creation of agricultural and horticultural insecticides having characteristics suitable for these application methods is required.

  As a result of intensive studies to develop a novel agricultural and horticultural insecticide, the present inventors have found that the phthalamide derivative represented by the general formula (I) of the present invention or a salt thereof is a novel compound not described in the literature, The compound described in the above literature is found to be an excellent agricultural and horticultural insecticide that exhibits an excellent insecticidal effect at a low dosage, and exhibits a high absorption transfer action from the root, especially by treatment with soil or the like. The present invention has been completed.

｛式中、Ｒ^１はC₁-C₆アルキル基、ハロC₁-C₆アルキル基、C₂-C₆アルケニル基、ハロC₂-C₆アルケニル基、C₂-C₆アルキニル基又はハロC₂-C₆アルキニル基を示す。
Ｒ^２及びＲ^３は同一又は異なっても良く、水素原子、C₁-C₆アルキル基、ハロC₁-C₆アルキル基、C₂-C₆アルケニル基、ハロC₂-C₆アルケニル基、C₂-C₆アルキニル基又はハロC₂-C₆アルキニル基を示す。
Ｒ^４及びＲ^５は同一又は異なっても良く、水素原子、C₁-C₆アルキル基、C₂-C₆アルケニル基、C₂-C₆アルキニル基、C₁-C₆アルキルカルボニル基、ハロC₁-C₆アルキルカルボニル基、C₁-C₆アルコキシカルボニル基又はハロC₁-C₆アルコキシカルボニル基を示す。 That is, the present invention relates to the general formula (I)

{Wherein R ¹ represents a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a halo C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group or a halo. A C ₂ -C ₆ alkynyl group;
R ² and R ³ may be the same or different and are a hydrogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a halo C ₂ -C ₆ alkenyl group, A C ₂ -C ₆ alkynyl group or a halo C ₂ -C ₆ alkynyl group;
R ⁴ and R ⁵ may be the same or different, and are a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ alkylcarbonyl group, a halo A C ₁ -C ₆ alkylcarbonyl group, a C ₁ -C ₆ alkoxycarbonyl group or a halo C ₁ -C ₆ alkoxycarbonyl group is shown.

（式中、Ｚは水素原子、C₁-C₆アルキル基、ハロC₁-C₁₀アルキル基、C₂-C₆アルケニル基、ハロC₂-C₆アルケニル基、C₂-C₆アルキニル基、ハロC₂-C₆アルキニル基、C₃-C₆シクロアルキル基、ハロC₃-C₆シクロアルキル基、フェニル基、同一又は異なっても良く、ハロゲン原子、シアノ基、ニトロ基、C₁-C₆アルキル基、ハロC₁-C₆アルキル基、C₁-C₆アルコキシ基及びハロC₁-C₆アルコキシ基から選択される１以上の置換基を有する置換フェニル基、複素環基又は同一若しくは異なっても良く、ハロゲン原子、シアノ基、ニトロ基、C₁-C₆アルキル基、ハロC₁-C₆アルキル基、C₁-C₆アルコキシ基及びハロC₁-C₆アルコキシ基から選択される１以上の置換基を有する置換複素環基を示す。） A is A-1

Wherein Z is a hydrogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₁₀ alkyl group, a C ₂ -C ₆ alkenyl group, a halo C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group Halo C ₂ -C ₆ alkynyl group, C ₃ -C ₆ cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group, phenyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ A substituted phenyl group having one or more substituents selected from a -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group and a halo C ₁ -C ₆ alkoxy group, a heterocyclic group, or the same or different and may a halogen atom, a cyano group, a nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group and halo C ₁ -C ₆ alkoxy group A substituted heterocyclic group having one or more selected substituents is shown.)

（式中、Ｚは前記に同じ。）で表されるテトラゾリル基を示す。
Ｘはハロゲン原子、ニトロ基、シアノ基、C₁-C₆アルキル基、ハロC₁-C₆アルキル基、C₁-C₆アルコキシ基、ハロC₁-C₆アルコキシ基、C₁-C₆アルキルチオ基、ハロC₁-C₆アルキルチオ基、C₁-C₆アルキルスルフィニル基、ハロC₁-C₆アルキルスルフィニル基、C₁-C₆アルキルスルホニル基又はハロC₁-C₆アルキルスルホニル基を示し、ｍは０〜４の整数を示す。
Ｙはハロゲン原子、ニトロ基、シアノ基、C₁-C₆アルキル基、ハロC₁-C₆アルキル基、C₁-C₆アルコキシ基、ハロC₁-C₆アルコキシ基、C₁-C₆アルキルチオ基、ハロC₁-C₆アルキルチオ基、C₁-C₆アルキルスルフィニル基、ハロC₁-C₆アルキルスルフィニル基、C₁-C₆アルキルスルホニル基又はハロC₁-C₆アルキルスルホニル基を示し、ｐは０〜４の整数を示す。
ｎは０〜２の整数を示す。｝で表されるフタルアミド誘導体又はその塩類及びこれを有効成分とする農園芸用殺虫剤並びにその使用方法に関する。 Or A-2

(Wherein Z is the same as above) represents a tetrazolyl group.
X is a halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, a halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group or halo C ₁ -C ₆ alkylsulfonyl group M represents an integer of 0 to 4.
Y is a halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, a halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group or halo C ₁ -C ₆ alkylsulfonyl group P represents an integer of 0 to 4.
n shows the integer of 0-2. } The phthalamide derivative or its salt represented by these, and the agricultural and horticultural insecticide which uses this as an active ingredient, and its usage.

｛式中、Ｒ^５は水素原子、C₁-C₆アルキル基、C₂-C₆アルケニル基、C₂-C₆アルキニル基、C₁-C₆アルキルカルボニル基、ハロC₁-C₆アルキルカルボニル基、C₁-C₆アルコキシカルボニル基又はハロC₁-C₆アルコキシカルボニル基を示す。 Furthermore, the present invention relates to a general formula (III) which is an intermediate thereof.

{Wherein R ⁵ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ alkylcarbonyl group, a halo C ₁ -C ₆ alkyl A carbonyl group, a C ₁ -C ₆ alkoxycarbonyl group or a halo C ₁ -C ₆ alkoxycarbonyl group;

（式中、Ｚは水素原子、C₁-C₆アルキル基、ハロC₁-C₁₀アルキル基、C₂-C₆アルケニル基、ハロC₂-C₆アルケニル基、C₂-C₆アルキニル基、ハロC₂-C₆アルキニル基、C₃-C₆シクロアルキル基、ハロC₃-C₆シクロアルキル基、フェニル基、同一又は異なっても良く、ハロゲン原子、シアノ基、ニトロ基、C₁-C₆アルキル基、ハロC₁-C₆アルキル基、C₁-C₆アルコキシ基及びハロC₁-C₆アルコキシ基から選択される１以上の置換基を有する置換フェニル基、複素環基又は同一若しくは異なっても良く、ハロゲン原子、シアノ基、ニトロ基、C₁-C₆アルキル基、ハロC₁-C₆アルキル基、C₁-C₆アルコキシ基及びハロC₁-C₆アルコキシ基から選択される１以上の置換基を有する置換複素環基を示す。） A is A-1

(Wherein, Z is a hydrogen atom, C ₁ -C ₆ alkyl, halo C ₁ -C ₁₀ alkyl group, C ₂ -C ₆ alkenyl group, halo C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group Halo C ₂ -C ₆ alkynyl group, C ₃ -C ₆ cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group, phenyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ A substituted phenyl group having one or more substituents selected from a -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group and a halo C ₁ -C ₆ alkoxy group, a heterocyclic group, or It may be the same or different and is from a halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group and halo C ₁ -C ₆ alkoxy group A substituted heterocyclic group having one or more selected substituents is shown.)

（式中、Ｚは前記に同じ。）で表されるテトラゾリル基を示す。
Ｙはハロゲン原子、ニトロ基、シアノ基、C₁-C₆アルキル基、ハロC₁-C₆アルキル基、C₁-C₆アルコキシ基、ハロC₁-C₆アルコキシ基、C₁-C₆アルキルチオ基、ハロC₁-C₆アルキルチオ基、C₁-C₆アルキルスルフィニル基、ハロC₁-C₆アルキルスルフィニル基、C₁-C₆アルキルスルホニル基又はハロC₁-C₆アルキルスルホニル基を示し、ｐは０〜４の整数を示す。｝で表されるアニリン誘導体又はその塩類にも関する。 Or A-2

(Wherein Z is the same as above) represents a tetrazolyl group.
Y is a halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, a halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group or halo C ₁ -C ₆ alkylsulfonyl group P represents an integer of 0 to 4. } Is also related to the aniline derivative represented by the formula:

  The phthalamide derivative represented by the general formula (I) of the present invention exhibits an excellent control effect as an agricultural and horticultural insecticide, and other agricultural and horticultural insecticides, acaricides and nematicides. Also, when used in combination with fungicides, herbicides, plant growth regulators, biological pesticides, etc., an excellent control effect can be obtained.

In the definition of the general formula (I) of the phthalamide derivative of the present invention, the “halogen atom” refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom. The “C ₁ -C ₆ alkyl group” means a linear or branched alkyl group having 1 to 6 carbon atoms, such as a methyl group, ethyl group, n-propyl group, i-propyl group, n Examples include -butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, neopentyl group, n-hexyl group and the like. The “halo C ₁ -C ₁₀ alkyl group” refers to a linear or branched alkyl group having 1 to 10 carbon atoms substituted with one or more halogen atoms which may be the same or different. Fluoromethyl group, difluoromethyl group, perfluoroethyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, 2,2,2-trifluoro-1- (trifluoromethyl) Illustrate ethyl group, 2,2,2-trifluoro-1-methyl-1- (trifluoromethyl) ethyl group, chloromethyl group, bromomethyl group, 1-bromoethyl group, 2,3-dibromopropyl group, etc. Can do. The “C ₁ -C ₆ alkoxy group” refers to a linear or branched alkoxy group having 1 to 6 carbon atoms, such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, n -Butoxy group, s-butoxy group, t-butoxy group, n-pentyloxy group, i-pentyloxy group, neopentyloxy group, n-hexyloxy group and the like can be exemplified. The “halo C ₁ -C ₆ alkoxy group” refers to a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, for example, difluoro Examples thereof include a methoxy group, a trifluoromethoxy group, and a 2,2,2-trifluoroethoxy group.

  Examples of the “heterocyclic group” include pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group, Examples thereof include an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, an imidazolyl group, a triazolyl group, a pyrazolyl group, etc. Quinazoline, indole, indoline, chroman, isochroman, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzoxazole, benzoxazole Zochiazoru, benzimidazole, can be exemplified indazole like.

  Examples of the salt of the phthalamide derivative represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, acetate, fumarate, maleate, and oxalate. And organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate, and salts with sodium ion, potassium ion, calcium ion, and the like. Examples of the salt of the aniline derivative represented by the general formula (III) as an intermediate include inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, fumarate, maleate, Examples thereof include organic acid salts such as oxalate, methanesulfonate, benzenesulfonate, and paratoluenesulfonate.

In the phthalamide derivative represented by the general formula (I) of the present invention, R ¹ is preferably a C ₁ -C ₆ alkyl group, and particularly preferably a methyl group or an ethyl group. R ² and R ³ are particularly preferably a hydrogen atom or a methyl group. R ⁴ and R ⁵ are particularly preferably a hydrogen atom. X is preferably a halogen atom, particularly preferably a chlorine atom, a bromine atom or an iodine atom. m is preferably 1 or 2, particularly preferably 1. Y is preferably a halogen atom, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group, and particularly preferably a methyl group or a chlorine atom. p is preferably 1 or 2, particularly preferably 1. Z is preferably a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₁₀ alkyl group, a C ₂ -C ₆ alkenyl group, a halo C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a halo C _2- C ₆ alkynyl group, C ₃ -C ₆ cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group, phenyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group A substituted phenyl group or a heterocyclic group having one or more substituents selected from a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group and a halo C ₁ -C ₆ alkoxy group, particularly preferably Halo C ₁ -C ₁₀ alkyl group. n is preferably an integer of 0 to 2, but 2 is particularly preferable.

  The phthalamide derivative represented by the general formula (I) of the present invention may contain one or more asymmetric carbon atoms or asymmetric centers in the structural formula, and may contain two or more optical isomers and dia Stereomers may exist, and the present invention includes all the optical isomers and a mixture in which they are contained in an arbitrary ratio. The sulfonamide derivative represented by the general formula (I) of the present invention has two or more geometric isomers derived from one or more carbon-carbon double bonds in the structural formula. However, the present invention includes all the geometric isomers and the mixtures in which they are contained in an arbitrary ratio.

（式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ａ、Ｘ、Ｙ、Ｚ、ｍ、ｎ及びｐは前記に同じくし、ｈａｌはハロゲン原子を示す。） The phthalamide derivative represented by the general formula (I) of the present invention can be produced according to the method described in JP-A-11-240857 or JP-A-2001-131141, for example, the production method shown below. However, it is not limited to these.
Manufacturing method 1.

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A, X, Y, Z, m, n and p are the same as described above, and hal represents a halogen atom.)

By reacting the phthalisoimide derivative represented by the general formula (II) with the aniline derivative represented by the general formula (III) in an inert solvent in the presence or absence of an acid or a base, A phthalamide derivative represented by the formula (I-1) is used, and the phthalamide derivative (I-1) is reacted with a halide represented by the general formula (IV) in the presence of a dehydrohalogenating agent and an inert solvent. Thus, a phthalamide derivative represented by the general formula (I-2) is obtained, and the phthalamide derivative (I-2) is reacted with an oxidizing agent in the presence of an inert solvent, thereby being represented by the general formula (I). Phthalamide derivatives can be produced. When R ⁴ is a hydrogen atom, the phthalamide derivative represented by the general formula (I-1) is oxidized in the presence of an inert solvent without passing through the phthalamide derivative represented by the general formula (I-2). By reacting with an agent, a phthalamide derivative represented by the general formula (I) can be produced.

[1-1] General formula (II) → General formula (I-1)
This reaction is described in J. Org. Med. Chem., 1967, Vol. 10, p. 982, the target product can be produced. The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. Examples thereof include linear or cyclic ethers such as tetrahydrofuran, diethyl ether, methyl t-butyl ether, dioxane, chloroform, methylene chloride. Examples include halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, and esters such as ethyl acetate and butyl acetate. These inert solvents can be used alone or in admixture of two or more. Examples of the acid that can be used in this reaction include organic acids such as acetic acid and trifluoroacetic acid, and inorganic acids such as hydrochloric acid and sulfuric acid. The amount of the acid used is phthalisoso represented by the general formula (II). What is necessary is just to select suitably from the range of a catalyst amount thru | or an excess mole with respect to an imide derivative. Examples of the base include organic bases such as triethylamine and pyridine, and inorganic bases such as potassium carbonate, sodium hydrogen carbonate, sodium carbonate, sodium hydroxide, and the amount used thereof is represented by the general formula (II). What is necessary is just to select suitably from the range of a catalyst amount thru | or excess mole with respect to the phthalisoimide derivative represented. The reaction temperature can be from 0 ° C. to the boiling point of the inert solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but is in the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the target product according to a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

[1-2] General formula (I-1) → General formula (I-2)
The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated compounds such as fluorobenzene, chlorobenzene and dichlorobenzene. Aromatic hydrocarbons, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chain or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, esters such as ethyl acetate, dimethylformamide, dimethylacetamide, etc. Inert solvents such as amides, acids such as acetic acid, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and the like, and these inert solvents may be used alone or in combination of two or more. Can be used. Examples of the dehydrohalogenating agent include organic bases such as triethylamine and pyridine, and inorganic bases such as potassium carbonate, sodium hydrogen carbonate, sodium carbonate and sodium hydroxide. Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any of the reactants can be used in excess. The reaction temperature can be from room temperature to the reflux temperature of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the target product according to a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

[1-3] General formula (I-1) or (I-2) → General formula (I)
The inert solvent used in this reaction may be any one that does not significantly inhibit the progress of this reaction. For example, halogenated hydrocarbons such as methylene chloride and chloroform, aromatic hydrocarbons such as toluene and xylene, fluoro Examples thereof include halogenated aromatic hydrocarbons such as benzene, chlorobenzene, and dichlorobenzene, acids such as acetic acid, and alcohols such as methanol, ethanol, and propanol. Examples of the oxidizing agent include metachloroperbenzoic acid, peracetic acid, potassium metaperiodate, potassium hydrogen persulfate (oxone), hydrogen peroxide and the like, and the amount used thereof is represented by the general formula (I-1). Alternatively, the phthalamide derivative represented by (I-2) may be appropriately selected from the range of 0.5 to 3 equivalents. The reaction temperature may be in the range of −50 ° C. to the boiling point of the inert solvent used, and the reaction time is not constant depending on the reaction temperature, reaction scale, etc., but is in the range of several minutes to 24 hours. After completion of the reaction, it may be isolated from the reaction system containing the target product according to a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

  The phthalisoimide derivative represented by the general formula (II) which is a raw material compound of the present invention can be produced according to the production methods described in JP-A Nos. 11-240857 and 2001-131141.

（式中、Ｒ^５、Ｙ、Ｚ、ｐ及びｈａｌは前記に同じくし、Ｍはナトリウム原子、カリウム原子等の金属原子又はトリメチルシリル基を示す。） The aniline derivative represented by the general formula (III) which is a raw material compound of the present invention is described in J. Org. Org. Chem., 1976, 41, p. Org. Chem., 1993, Vol. 58, p. 32 can be used in combination. For example, it can be manufactured by the manufacturing method shown below.
Manufacturing method 2.

(In the formula, R ⁵ , Y, Z, p and hal are the same as described above, and M represents a metal atom such as a sodium atom or a potassium atom or a trimethylsilyl group.)

  By reacting the anilide derivative represented by the general formula (V) and the halogenating agent in the presence of an inert solvent, the haloimide derivative (VI) represented by the general formula (VI) is obtained. The tetrazole derivative (VIII) represented by the general formula (VIII) is obtained by reacting with an azide represented by the general formula (VII) in the presence of an inert solvent without separation or isolation. Can be isolated or reduced in the presence of an inert solvent to produce the aniline derivative of the present invention represented by the general formula (III-1). Further, by reacting the aniline derivative of the present invention represented by the general formula (III-1) with a halide represented by the general formula (IX) in the presence of a base and an inert solvent, (III-2) The aniline derivative of this invention represented by these can be manufactured.

[2-1] General formula (V) → General formula (VI)
The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. For example, halogenated hydrocarbons such as methylene chloride and chloroform, aromatic hydrocarbons such as toluene and xylene, acetonitrile. Nitriles such as benzene, halogenated aromatic hydrocarbons such as fluorobenzene, chlorobenzene and dichlorobenzene can be exemplified, and these inert solvents can be used alone or in admixture of two or more. Examples of the halogenating agent include thionyl chloride, thionyl bromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, phosphorus tribromide, phosphorus oxybromide, carbon tetrachloride-triphenylphosphine, carbon tetrabromide-tri Phenylphosphine and the like can be exemplified, and the amount used can be appropriately selected from the range of 0.5 to 3 equivalents relative to the anilide derivative represented by the general formula (V). The reaction temperature may be in the range of −50 ° C. to the boiling point of the inert solvent used, and the reaction time is not constant depending on the reaction temperature, reaction scale, etc., but is in the range of several minutes to 24 hours. After completion of the reaction, the target product can be produced by isolating it from the reaction system containing the target product according to a conventional method, and purifying it by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

[2-2] General formula (VI) → General formula (VIII)
The inert solvent used in this reaction may be any one that does not significantly inhibit the progress of this reaction. For example, halogenated hydrocarbons such as methylene chloride and chloroform, aromatic hydrocarbons such as toluene and xylene, fluoro Illustrative examples include halogenated aromatic hydrocarbons such as benzene, chlorobenzene and dichlorobenzene, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and the like. These inert solvents can be used alone or in admixture of two or more. Examples of the azides that can be used in this reaction include sodium azide, potassium azide, trimethylsilyl azide and the like, and the amount used is 0.5 to 3 with respect to the haloimide derivative represented by the general formula (VI). What is necessary is just to select suitably from the range of an equivalent. The reaction temperature may be in the range of −50 ° C. to the boiling point of the inert solvent used, and the reaction time is not constant depending on the reaction temperature, reaction scale, etc., but is in the range of several minutes to 24 hours. After completion of the reaction, the target product can be produced by isolating it from the reaction system containing the target product according to a conventional method, and purifying it by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

[2-3] General formula (VIII) → General formula (III-1)
The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. Examples thereof include alcohols such as methanol and ethanol, ethers such as tetrahydrofuran and dioxane, and water. These inert solvents can be used alone or in admixture of two or more. Moreover, the aqueous solution of the acid used as the reducing agent shown below can be used as an inert solvent as it is. Examples of the reducing agent that can be used in this reaction include metal-acids, metal-salts, and the like. Examples of metals include iron, tin, and zinc. Examples of acids include mineral acids such as hydrochloric acid and sulfuric acid. Examples of salts of organic acids such as acetic acid, tin chloride, etc. include ammonium chloride. Moreover, it is also possible to use these in combination. The amount of the reducing agent to be used may be appropriately selected from the range of 1 to 10 mol of the metal and 0.05 to 10 mol of the acid and salt with respect to the tetrazole derivative represented by the general formula (VIII). The reduction reaction can also be performed by a catalytic hydrogenation method in the presence of a catalyst. Examples of the catalyst include palladium carbon and Raney nickel, and the amount of the catalyst is appropriately selected within a range of 0.00001 to 0.1 moles relative to the tetrazole derivative represented by the general formula (VIII). It ’s fine. Hydrogen pressure may be suitably selected from a range of normal pressure to 100 kg / cm ^2, but preferably range of normal pressure to 10 kg / cm ^2. The reaction temperature may be selected from the range of 0 to 150 ° C., and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours. After completion of the reaction, the target product can be produced by isolating it from the reaction system containing the target product according to a conventional method, and purifying it by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

[2-4] General formula (III-1) → General formula (III-2)
This reaction may be performed in the same manner as [1-2].

（式中、Ｒ^５、Ｙ、Ｚ、ｐ、ｈａｌ及びＭは前記に同じ。） Manufacturing method 3.

(In the formula, R ⁵ , Y, Z, p, hal and M are the same as above.)

  By reacting the benzamide derivative represented by the general formula (V-1) and the halogenating agent in the presence of an inert solvent, the haloimide derivative represented by the general formula (VI-1) is obtained. A tetrazole represented by the general formula (VIII-1) is obtained by reacting the azide represented by the general formula (VII) with or without being isolated in the presence of an inert solvent. The aniline derivative of the present invention represented by the general formula (III-3) is produced by isolating the tetrazole derivative (VIII-1) as a derivative, or reducing it in the presence of an inert solvent without isolation. can do. Further, by reacting the aniline derivative of the present invention represented by the general formula (III-3) with a halide represented by the general formula (IX) in the presence of a base and an inert solvent, (III-4) The aniline derivative of this invention represented by these can be manufactured.

[3-1] General formula (V-1) → General formula (VI-1)
This reaction may be performed in the same manner as [2-1].
[3-2] General formula (VI-1) → General formula (VIII-1)
This reaction may be performed in the same manner as [2-2].
[3-3] General formula (VIII-1) → General formula (III-3)
This reaction may be the same as [2-3].
[3-4] General formula (III-3) → General formula (III-4)
This reaction may be performed in the same manner as [1-2].

  The agricultural and horticultural insecticide containing the phthalamide derivative represented by the general formula (I) of the present invention as an active ingredient is various agricultural and forestry, horticultural, stored grain pests and hygiene that harm rice plants, fruit trees, vegetables, other crops, and flowering plants. Suitable for controlling pests such as pests and nematodes, such as apple wolfberry (Adoxophyes orana fasciata), chanokokumon hamakiki (Adoxophyes sp.), Apple hawk moth (Grapholita inopinata), nashihi messhinki (Grapholita molesta), bean melon moth (Leguminivora glycinivorella), mulberry (Olethreutes mori), chanohosoga (Caloptilia thevivora), apple hosoga (Caloptilia zachrysa), kinmonhosoga (Phyllonorycter ringoniella), pear moth (Spulerrina astaurlio), cigarette butterfly Codling moth (Laspeyresia pomonella), cod moth (Plutella x ylostella, Argyresthia conjugella, Momoshinigaiga (Carposina niponensis), Chilo suppressalis, Cnaphalocrocis medinalis, Ephestia elutelia, Glyphodes rpaga, Glyphodes rpiga Parrotara guttata, Pseudaletia separata,

Lepidopterous insects such as Sesamia inferens, Spodoptera litura, Spodoptera exigua, Macrosteles fascifrons, Nephotettix cincticeps, gen pari v (Diaphorina citri), Grape whiteflies (Aleurolobus taonabae), Tobacco whiteflies (Bemisia tabaci), Onsatsu whitefly (Trialeurodes vaporariorum), Flounder (Lipaphis erysimi), Momoka aphid (Myzus persicae), Cenophyllum estros (Pulvinaria aurantii), Pseudaonidia duplex, Comstockaspis perniciosa, Hemiptera (Unaspis yanonensis), etc. Nematode (Pratylenchus sp.), Scallop (Anomala rufocuprea), beetle (Popilla japonica), tobacco beetle (Lasioderma serricorne),

Lyctus brunneus, Epilachna vigintioctopunctata, Japanese weevil (Callosobruchus chinensis), Japanese weevil (Listroderes costirostris), Scotch beetle (Sitophilus zeamais), Grand hops Cucumber beetle (Aulacophora femoralis), rice beetle beetle (Oulema oryzae), horned beetle beetle (Phyllotreta striolata), pine beetle (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata), Mexican beetle vari (Epilachna beetle) Coleopterous pests such as Drosophila (Dacus (Zeugodacus) cucurbitae), Drosophila (Dacus (Bactrocera) dorsalis), Agromyza oryzae, Onion fly (Delia antiqua), Dane fly (Dali) a platura), soybean flies (Asphondylis sp.), house flies (Musca domestica), Culex pipiens pipiens, etc., Diptera pestylates (Pratylenchus coffeae), potato cyst nematodes (Glabodera rostchiensis)

Pesticides such as root-knot nematode (Meloidogyne sp.), Tylenchulus semipenetrans, Aphelenchus avenae, and Aphelenchoides ritzemabosi, Panonychus ciP Nite spider mite (Tetranychus cinnabarinus), Kanzawa spider mite (Tetranychus kanzawai Kishida), Nite spider mite (Tetranychus urticae Koch), Chinese prickly tick (Acaphylla theae), Mika Sabi mite (Aculops pelekassi), Tick carina, tick carina It has a strong insecticidal effect against eye pests.

  Rhinotermitidae (Coptotermes formosanus Shiraki), Yamato termites (Reticulitermessperatus (Kolbe)), North America, Reticulitermes hesperus, Reticulitermes tibialis, Reticulitermes flavipes, santonensis, etc., American ant termites (Incisitermes minor (Hagen)), Termiteidae (termitidae), Taiwan termites (Odontotermes formosanus (Shiraki)), Leopard termites (Kalotermitidae), Diptera Termites (Cryptotermes domesticus (Haviland)) (Termopsidae) Hodotermopsis jzponica (Holmgren) and other white ants that cause damage to houses, building materials, furniture, leather, textiles, processed vinyl products, electric wires and cables, etc. It has an ant effect. In addition, the ants of the Formicidae (Monomorium pharaoni Linnes), the Japanese ants (Monomorium nipponense Wheeler), the giant ants (Camponotus kiusiuensis Santschi), the black ants (Formica japonica Motschulsky), the black ants (Lasius fuliginosus, etc.) Invasion of agricultural products such as fire ant (Solenopsis richteri, Solenopsis invicta, Solenopsis geminata (F)) or public facilities and houses such as parks, and ant killing ants that are harmful to humans at low doses It has an effect.

  Furthermore, phthalamide derivatives represented by the general formula (I) of the present invention include cattle, horses, sheep and other domestic animals, dogs, cats and other pets, as well as rodents such as mice, rats, hamsters and squirrels, It can also be used against ectoparasites of rabbit eyes, carnivorous animals such as ferrets, and birds such as ducks, chickens, and pigeons. For example, cat fleas (Ctenocephalides felis), dog fleas (Ctenocephalides canis), keops rat fleas (Xenopsylla cheopis) ) And other flea insects, Haemphyxalis longicornis, Boophilus microplus, and other ticks It has an insecticidal effect.

  The agricultural and horticultural insecticide containing the phthalamide derivative represented by the general formula (I) of the present invention as an active ingredient is effective against the above-mentioned pests that cause damage to paddy field crops, field crops, fruit trees, vegetables, other crops, and flower buds. It has a remarkable control effect, so that it is possible to raise seedlings, paddy fields, fields, fruit trees, vegetables, other crops, flower buds, etc. before or when the occurrence of pests is confirmed, according to the time when the occurrence of pests is expected. The desired effect of the agricultural and horticultural insecticide of the present invention can be obtained by treating the seeds, paddy water, stalks and leaves, or soil and other cultivation carriers. Among them, it is treated with seedling soil such as crops, flower buds, planting hole soil at the time of transplantation, plant origin, irrigation water, cultivated water in hydroponics, etc., and the present compound is absorbed from the root through or without soil. Application utilizing the so-called osmotic transfer property by making it a preferable form of use. In recent years, genetically modified crops (herbicide-tolerant crops, pest-resistant crops incorporating insecticidal protein-producing genes, disease-resistant crops incorporating resistance-inducing substance-producing genes for diseases, food-enhancing crops, preservative-enhancing crops, yield Improved crops, etc.), insect pheromones (communication agents for oyster moths, mushrooms, etc.), IPM (integrated pest management) technology using natural enemy insects, etc., and the agricultural and horticultural insecticides of the present invention are These techniques can be used in combination or systematized.

Although the plant which can use the agricultural and horticultural insecticide of this invention is not specifically limited, For example, the plant shown below is mentioned.
Cereals (eg, rice, barley, wheat, rye, oats, corn, etc.), beans (soybeans, red beans, broad beans, peas beans, kidney beans, peanuts, etc.), fruit trees / fruits (apples, citrus fruits, pears, strawberries) Peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, strawberries, etc.), leaves and fruits and vegetables (cabbage, tomatoes, spinach, broccoli, lettuce, onion, leeks, peppers, eggplant, peppers, etc.), root vegetables (carrots) , Potato, sweet potato, taro, radish, lotus root, turnip, burdock, garlic, etc.), processing crops (crab, hemp, beet, hop, sugar cane, sugar beet, olive, rubber, coffee, tobacco, tea, etc.), cucumber ( Pumpkins, cucumbers, cucumbers, watermelons, melons, etc.), pastures (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turf Korean turf, bentgrass, etc.), fragrances, etc. crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, roses, carnations, orchids), garden trees (ginkgo, cherry, aoki, etc.) ), Forest trees (Todomatsu, Ezomatsu, pine, hiba, cedar, firewood, etc.).

  The agricultural and horticultural insecticide of the present invention is used to control various pests as they are, or appropriately diluted with water or the like, or suspended in an amount effective for controlling pests or nematodes. For pests and nematodes that occur in fruit trees, cereals, vegetables, etc., in addition to spraying on the foliage, seed immersion in seeds, seed dressing, calper treatment Etc. Seed treatment, soil all layer mixing, crop application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface application, etc. It can also be absorbed and used. In addition, it can be applied to nutrient solution in nutrient solution (hydroponics) cultivation, smoke, or trunk injection. Furthermore, the agricultural and horticultural insecticide of the present invention may be used as it is, appropriately diluted with water or the like or suspended in an amount effective for pest control in a place where the occurrence of the pest is predicted. For example, in addition to spraying on stored grain pests, house pests, sanitary pests, forest pests, etc., they can also be used as application to house building materials, smoke, bait and the like.

Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted and the seed is immersed in a liquid state to infiltrate the drug, a solid preparation or liquid preparation is mixed with the seed, Examples thereof include a method of treating and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting.
The “seed” for performing the seed treatment means a plant body at the initial stage of cultivation used for the propagation of plants, for example, for seeds, bulbs, tubers, seed buds, stock buds, baskets, bulbs, or cuttings. Mention may be made of plants for vegetative propagation.
The “soil” or “cultivation carrier” of the plant when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that can grow plants may be used, and so-called soil, seedling mats, water, etc. may be used. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, high It may be a molecular substance, rock wool, glass wool, wood chip, bark or the like.

As a spraying method for crop foliage, stored grain pests, house pests, hygiene pests, forest pests, etc., dilute liquid preparations such as emulsions and flowables or solid preparations such as wettable powders or granular wettable powders with water as appropriate. , A method of spraying, a method of spraying powder, smoke or the like.
Examples of the application method to the soil include, for example, a method in which a liquid preparation is diluted or not diluted with water and applied to a plant stock or a seedling nursery, etc. A method of spraying to a nursery, etc., a method of spraying powder, wettable powder, granule wettable powder, granule, etc. before sowing or transplanting and mixing with the whole soil, a planting hole, making before planting or planting a plant body Examples thereof include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.

As a method for applying rice to a seedling box, the dosage form may vary depending on the time of application such as application during sowing, greening period, application during transplantation, etc., but agents such as powder, granule wettable powder, granules, etc. Apply by mold. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with ground soil, mixed with soil covering, mixed with the entire soil. Simply, the soil and the various preparations may be applied alternately in layers.
As a method of application to paddy fields, solid preparations such as jumbo agents, packs, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields. In addition, at the time of rice planting, an appropriate formulation can be sprayed and injected into the soil as it is or mixed with fertilizer. In addition, by using a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water mouth or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.

In field crops, it can be treated to seeds or a cultivation carrier close to the plant body from sowing to raising seedling. In plants that are sown directly in a field, in addition to direct treatment on seeds, treatment on the plant source of the plant being cultivated is suitable. For example, a spray treatment using a granule or a irrigation treatment in a liquid of a drug diluted or not diluted with water can be performed. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.
As the seeding of the cultivated plant to be transplanted and the treatment of the seedling raising period, in addition to the direct treatment to the seed, the irrigation treatment of the liquid drug or the granule spraying treatment to the seedling nursery is preferred. In addition, it is also preferable to treat a granule in a planting hole at the time of planting or to mix it with a cultivation carrier in the vicinity of the transplantation site.
The agricultural and horticultural insecticide of the present invention is generally used in a form convenient for use according to a conventional method for agricultural chemical preparations.
That is, the phthalamide derivatives represented by the general formula (I) are dissolved, separated, suspended, mixed and impregnated by mixing them in an appropriate inert carrier or in an appropriate ratio together with auxiliary agents as necessary. And adsorbed or adhered to a suitable dosage form such as a suspension, emulsion, liquid, wettable powder, wettable granule, granule, powder, tablet, pack and the like.

  The inert carrier that can be used in the present invention may be either solid or liquid. Examples of materials that can be used as a solid carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, and tobacco stem flour. , Walnut shell powder, bran, fiber powder, residue after extraction of plant extract, synthetic polymer such as ground synthetic resin, clays (eg kaolin, bentonite, acid clay), talc (eg talc, pyrophyllite, etc.), Silicas {for example, diatomaceous earth, silica sand, mica, white carbon (some synthetic high-dispersion silicic acid called water-containing fine silicon and water-containing silicic acid, and some products contain calcium silicate as a main component)}, activated carbon, sulfur powder, pumice, Firing diatomaceous earth, brick ground, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic mineral powders, polyethylene, polypropylene, polychlorinated Plastic carriers such as vinylidene, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, fertilizer salts depreciation etc., can be exemplified compost or the like, which are used alone or in the form of a mixture of two or more.

  The material that can be used as a liquid carrier is selected from those having solvent ability itself and those capable of dispersing the active ingredient compound with the aid of an auxiliary agent without having solvent ability. The following carriers can be exemplified. These may be used alone or in the form of a mixture of two or more, such as water, alcohols (eg, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone). , Cyclohexanone etc.), ethers (eg ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran etc.), aliphatic hydrocarbons (eg kerosene, mineral oil etc.), aromatic hydrocarbons (eg benzene, toluene, xylene, Solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloroethane, chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (eg, ethyl acetate, diisopropylpropylate, dibutyl) Phthalate, dioctyl phthalate - bets, etc.), amides (e.g. dimethylformamide, diethylformamide, dimethylacetamide), nitriles (e.g., acetonitrile, etc.), and the like dimethyl sulfoxides.

Typical examples of auxiliary agents are shown below, but these auxiliary agents are used depending on the purpose, and used alone, in some cases, two or more kinds of auxiliary agents are used in combination, and in some cases, the auxiliary agent is completely auxiliary agent. It is also possible not to use.
For the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compound, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan Surfactants such as monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonic acid condensate, lignin sulfonate, and higher alcohol sulfate can be used.
For example, casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohol, pine oil, coconut oil, bentonite, lignin sulfonate, etc. are used for the purpose of stabilizing the dispersion of the active ingredient compound, sticking and / or binding. be able to. For the purpose of improving the fluidity of solid products, for example, waxes, stearates, alkyl phosphates and the like can be used.

Moreover, as a peptizer for suspension products, for example, naphthalenesulfonic acid condensate, condensed phosphate, etc., as an antifoaming agent, for example, silicone oil, etc., as a preservative, 1,2-benzisothiazolin-3-one Parachlorometaxylenol, butyl paraoxybenzoate, and the like can be used.
Furthermore, functional aids, activity enhancers such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, UV absorbers and other supplements as necessary Agents can also be used.
The blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of agricultural and horticultural insecticides. In the case of a granule, emulsion or wettable powder, 0.01 to 50 parts by weight is appropriate.
The agricultural or horticultural insecticide of the present invention is a crop in which the occurrence of the pest is predicted as it is, or is appropriately diluted with water or the like, or suspended in order to control various pests. What is necessary is just to use and apply to the place where generation | occurrence | production is not preferable.

The amount of the agricultural and horticultural insecticide of the present invention depends on various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc. Although it varies, the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 are according to the purpose.
The agricultural and horticultural insecticides of the present invention further include other pesticides, acaricides, nematicides, and fungicides for controlling pests to be controlled, for the purpose of expanding the appropriate period of control, or for the purpose of reducing the dosage. It can also be used by mixing with biological pesticides, etc., and can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc., depending on the situation of use.
Other agricultural and horticultural insecticides, acaricides and nematicides used for such purposes include, for example, ethione, trichlorfone, methamidophos, acephate, dichlorvos, mevinphos, monocrotophos, malathion, dimethoate, formothion, mecarbam, bamidione, Thiometone, disulfotone, oxydeprophos, nared, methyl parathion, fenitrothion, cyanophos, propofos,

Fenthion, prothiophos, profenofos, isofenphos, temefos, phentoate, dimethylvinphos, chlorfevinphos, tetrachlorbinphos, phoxime, isoxathion, pyraclophos, methidathion, chloropyrifos, chlorpyrifos-methyl, pyridafenthion, diazinon, pyrimiphosmethyl, hosalone, phosmet, Dioxabenzophos, quinalphos, terbufos, etoprophos, kazusafos, mesulfenphos, DPS (NK-0795), phosphocarb, phenamiphos, isoamidophos, phosthiazeto, isazophos, enaprophos, fenthion, phosthietane, diclofenthion, thionadine, sulprophos, fendafothion Pyrethrin, allethrin, praretrin, les Trindade, permethrin, tefluthrin, bifenthrin, fenpropathrin, cypermethrin, alpha-cypermethrin, cyhalothrin, lambda-cyhalothrin, deltamethrin, acrinathrin,

Fenvalerate, esfenvalerate, cycloprotorin, etofenprox, halfenprox, silafluophene, flucitrinate, fulvalinate, mesomil, oxamyl, thiodicarb, aldicarb, alanikalb, cartap, metolcarb, xylicarb, propoxur, phenoxycarb, fenocarb , Ethiophene Carb, Fenothiocarb, Bifenazate, Fenozcarb, Carbaryl, Pirimicurve, Carbofuran, Carbosulfuran, Frathiocarb, Benfuracarb, Aldoxycarb, Difenthiuron, Diflubenzuron, Teflubenzuron, Hexaflumuron, Novallon, Lufenuron, Flufenoxuron Azuron, fenbutane oxide, tricyclohexyl hydroxide Tin, sodium oleate, potassium oleate, methoprene, hydro-plane, binapacryl, amitraz, dicofol, Kelthane, chlorobenzylidene rate, phenylene Seo bromo rate, tetradifon, bensultap, Benzometo, tebufenozide, methoxyfenozide, pyridalyl,

Chromafenozide, propargite, acequinosyl, endosulfan, diophenolan, chlorfenapyr, fenpyroximate, tolfenpyrad, fipronil, tebufenpyrad, triazamate, etoxazole, hexithazox, nicotine sulfate, nitenpyram, acetamiprid, thiaclopridum, thiaclopridum, thiaclopridom Methylnon, pyrimidifene, pyridaben, cyromazine, TPIC (tripropyl isocyanurate), pymetrozine, clofentezin, buprofezin, thiocyclam, phenazaquin, quinomethionate, indoxacarb, polynactin complex, milbemectin, abamectin, emamectin benzoate , Spinosad, BT (Bacillus thuringiensis), azadirachtin, rotenone, hydroxypropyl starch, levamisole hydrochloride, metam sodium, morantel tartrate, dazomet, trichlamide, pastoria, monacrosporium fimatopagum, etc. Examples of acaricides and nematicides are

As agricultural and horticultural fungicides used for the same purpose, for example, sulfur, lime sulfur combination, basic copper sulfate, iprobenphos, edifenphos, tolcrofos methyl, thiram, polycarbamate, gnebu, manzeb, mancozeb, propineb, Thiophanate, thiophanate methyl, benomyl, iminotadine acetate, iminotazine albesylate, mepronil, flutolanil, pencyclon, furamethopyl, tifluzamide, metalaxyl, oxadoxyl, carpropamide, diclofluanide, fursulfamide, chlorothalonil, cresoxime methyl, phenoxolol, fluxol Procymidone, Vinclozoline, Iprodione, Triazimephone, Triflumizole, Vitertanol, Triflumiso , Ipconazole, fluconazole, propiconazole, difenoconazole, microbutanyl, tetraconazole, hexaconazole, tebuconazole, imibenconazole, prochloraz, pefrazoate, cyproconazole, isoprothiolane, phenalimol, pyrimethanil, mepanipyrim, pyrifenox, fluazinam , Dichromedin, azoxystrobin, trifloxystrobin, orissastrobin, thiadiazine, captan, thiazinyl, probenazole, acylbenzofural S-methyl (CGA-245704), fusaride, tricyclazole, pyroxylone, quinomethionate, oxolinic acid, dithianon, cyazofamide, thiazinyl, diclomethymet , Kasugamycin, validamycin, polio Singh, blasticidin, can be exemplified agricultural and horticultural fungicides such as streptomycin,

Similarly, herbicides include, for example, glyphosate, sulfosate, glufosinate, bialaphos, butamifos, esprocarb, prosulfocarb, beniocarb, pilibutycarb, ashram, linuron, dimron, isouron, bensulfuron methyl, cyclosulfamuron, sinosulfuron, pyrazosulfuron Ethyl, azimusulfuron, imazosulfuron, tenylchlor, alachlor, pretilachlor, clomeprop, etobenzanide, mefenacet, flufenacet, fentrazamide, pendimethalin, bifenox, acifluophene, lactofen, cihalohop butyl, ioxynyl, bromobutide, aroxidim, cetoxime , Napropamide, indanophan, pyrazolate, benzophenap Pyraflufenethyl, imazapyr, sulfentrazone, fenfentrol, bentoxazone, oxazoazone, paraquat, diquat, pyriminobac, simazine, atrazine, dimetamethrin, triadifram, benfrate, fluthiaset methyl, quizalofopethyl, bentazone, oxadichrome mehon And herbicides such as azaphenidine, benzobicyclone, and calcium peroxide.

  Examples of biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect poxvirus (Entomopox virus, EPV) ) And other virus preparations, Monocrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasturia penetrans, etc. As microbial pesticides, Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc. use Microbial pesticides, by using mixed such as biological pesticides utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.

  In addition, as biological pesticides, for example, Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa seibito mites ), Natural enemy organisms such as Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl acetate, (E, Z) -4,10-tetradecadinyl acetate, (Z) -8-dodecenyl acetate, (Z) -11-tetradecenyl acetate, (Z) -13-icosen-10-one, 14-methyl-1- It can also be used in combination with pheromone agents such as octadecene. .

４−アミノ−２−メチルニトロベンゼン３．０ｇ（２０ミリモル）のテトラヒドロフラン５０ｍｌ溶液に、トリエチルアミン２．４ｇ（２４ミリモル）を加え、氷水冷下、ｎ−ヘプタフルオロ酪酸無水物８．１ｇ（２０ミリモル）を滴下した。室温に戻し、１２時間攪拌した後、反応溶液を氷水中に注ぎ、酢酸エチルで抽出した。有機層を無水硫酸マグネシウムで乾燥した後、減圧濃縮して目的物６．８ｇを得た。
収率：定量的
物性：［^１ＨＮＭＲ，ＣＤＣｌ_３，δ値（ｐｐｍ）］
８．２１（ｂｒ，１Ｈ），８．１０（ｄ，１Ｈ），７．６４（ｄ，１Ｈ）,
７．６２（ｄｄ，１Ｈ），２．６８（ｓ，３Ｈ）． Although the typical example of this invention is illustrated below, this invention is not limited to these.
Example 1. N ² - (1,1-dimethyl-2-methylthioethyl) -3-iodo ^{-N 1 - [4- (5-} n- heptafluoropropyl tetrazol-1-yl) -2-methylphenyl] phthalamide (Compound No . 3-19) Production (1-1) Production of 4-n-heptafluoropropylcarbonylamino-2-methylnitrobenzene

To a solution of 3.0 g (20 mmol) of 4-amino-2-methylnitrobenzene in 50 ml of tetrahydrofuran was added 2.4 g (24 mmol) of triethylamine, and under ice-cooling, 8.1 g (20 mmol) of n-heptafluorobutyric anhydride. Was dripped. After returning to room temperature and stirring for 12 hours, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 6.8 g of the desired product.
Yield: Quantitative _{^{properties: [1 HNMR, CDCl 3,}} δ value (ppm)]
8.21 (br, 1H), 8.10 (d, 1H), 7.64 (d, 1H),
7.62 (dd, 1H), 2.68 (s, 3H).

４−ｎ−ヘプタフルオロプロピルカルボニルアミノ−２−メチルニトロベンゼン４．３ｇ（１２ミリモル）のアセトニトリル３０ｍｌ溶液に、トリフェニルホスフィン４．８ｇ（１９ミリモル）、四臭化炭素６．１ｇ（１９ミリモル）を加え、３時間加熱還流した。反応混合物を減圧濃縮した後ＤＭＦ３０ｍｌに溶かし、アジ化ナトリウム２．４ｇ（３７ミリモル）のＤＭＦ溶液にゆっくり滴下した。５時間攪拌した後、反応溶液を水に注ぎ、酢酸エチルで抽出した。有機層を無水硫酸マグネシウムで乾燥した後、減圧濃縮し、残渣をシリカゲルカラムクロマトグラフィーで精製して、目的物２．５ｇを得た。
収率：３４％
物性：［^１ＨＮＭＲ，ＣＤＣｌ_３，δ値（ｐｐｍ）］
８．１９（ｄ，１Ｈ），７．５１（ｓ，１Ｈ），７．５０（ｄ，１Ｈ），
２．７１（ｓ，３Ｈ）． (1-2) Production of 4- (5-n-heptafluoropropyltetrazol-1-yl) -2-methylnitrobenzene

To a solution of 4.3 g (12 mmol) of 4-n-heptafluoropropylcarbonylamino-2-methylnitrobenzene in 30 ml of acetonitrile was added 4.8 g (19 mmol) of triphenylphosphine and 6.1 g (19 mmol) of carbon tetrabromide. The mixture was heated to reflux for 3 hours. The reaction mixture was concentrated under reduced pressure, dissolved in 30 ml of DMF, and slowly added dropwise to a solution of 2.4 g (37 mmol) of sodium azide in DMF. After stirring for 5 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 2.5 g of the desired product.
Yield: 34%
Physical _{^{properties: [1 HNMR, CDCl 3,}} δ value (ppm)]
8.19 (d, 1H), 7.51 (s, 1H), 7.50 (d, 1H),
2.71 (s, 3H).

４−（５−ｎ−ヘプタフルオロプロピルテトラゾール−１−イル）−２−メチルニトロベンゼン２．５ｇ（６．７ミリモル）のエタノール７０ｍｌ溶液に、５％パラジウム炭素０．４ｇを加え、３気圧の水素下で一晩撹拌を行った。反応液をろ過し、減圧濃縮して目的物２．１ｇを得た。
収率：８５％
物性：［^１ＨＮＭＲ，ＣＤＣｌ_３，δ値（ｐｐｍ）］
７．２４（ｍ，３Ｈ），７．１８（ｍ，２Ｈ），２．３６（ｓ，３Ｈ）． (1-3) Production of 4- (5-n-heptafluoropropyltetrazol-1-yl) -2-methylaniline (Compound No. 7-3)

To a solution of 2.5 g (6.7 mmol) of 4- (5-n-heptafluoropropyltetrazol-1-yl) -2-methylnitrobenzene in 70 ml of ethanol was added 0.4 g of 5% palladium carbon, and hydrogen at 3 atm. Stirring was performed overnight. The reaction solution was filtered and concentrated under reduced pressure to obtain 2.1 g of the desired product.
Yield: 85%
Physical properties: [ ¹ HNMR, CDCl ₃ , δ value (ppm)]
7.24 (m, 3H), 7.18 (m, 2H), 2.36 (s, 3H).

３−ヨード−Ｎ−（１，１−ジメチル−２−メチルチオエチル）フタルイソイミド０．７ｇ（２．０ミリモル）をアセトニトリル１０ｍｌに溶かし、４−（５−ｎ−ヘプタフルオロプロピルテトラゾール−１−イル）−２−メチルアニリン０．７ｇ（２．０ミリモル）、トリフルオロ酢酸１０ｍｇを加え、室温下で１２時間撹拌した。析出した結晶を濾過しアセトニトリルで洗浄して、目的物０．６５ｇを得た。
収率：４６％
物性：融点 １６４−１６６℃ (1-4) 3-iodo ^{-N 1 - [4- (5-} n- heptafluoropropyl tetrazol-1-yl) ^{-2-methylphenyl]} -N 2 - (1,1-dimethyl-2-methylthioethyl ) Production of phthalamide (Compound No. 3-19)

3-Iodo-N- (1,1-dimethyl-2-methylthioethyl) phthalisoimide 0.7 g (2.0 mmol) was dissolved in 10 ml of acetonitrile, and 4- (5-n-heptafluoropropyltetrazole-1- Yl) -2-methylaniline (0.7 g, 2.0 mmol) and trifluoroacetic acid (10 mg) were added, and the mixture was stirred at room temperature for 12 hours. The precipitated crystals were filtered and washed with acetonitrile to obtain 0.65 g of the desired product.
Yield: 46%
Physical property: Melting point 164-166 ° C

３−ヨード−Ｎ^１−［４−（５−ｎ−ヘプタフルオロプロピルテトラゾール−１−イル）−２−メチルフェニル］−Ｎ^２−（１，１−ジメチル−２−メチルチオエチル）フタルアミド０．４ｇ（０．６ミリモル）のクロロホルム１０ｍｌ溶液に、氷水冷下、ｍ−クロロ過安息香酸０．３ｇ（１．２ミリモル）を加え、室温下で３時間攪拌した。炭酸カリウム水溶液ついで亜硫酸ナトリウム水溶液を加え、クロロホルムで抽出した。有機層を無水硫酸マグネシウムで乾燥した後、減圧濃縮した。得られた結晶をエーテルで洗い、３−ヨード−Ｎ^１−［４−（５−ｎ−ヘプタフルオロプロピルテトラゾール−１−イル）−２−メチルフェニル］−Ｎ^２−（１，１−ジメチル−２−メチルスルホニルエチル）フタルアミド０．３７ｇを得た。
収率：９３％
物性：融点 １４１−１４２℃ Example 2 3-iodo ^{-N 1 - [4- (5-} n- heptafluoropropyl tetrazol-1-yl) ^{-2-methylphenyl]} -N 2 - (1,1-dimethyl-2-methylsulfonyl-ethyl) phthalamide (Compound Production of No. 3-21)

3-iodo ^{-N 1 - [4- (5-} n- heptafluoropropyl tetrazol-1-yl) ^{-2-methylphenyl]} -N 2 - (1,1- dimethyl-2-methylthioethyl) phthalamide 0.4g To a solution of (0.6 mmol) in chloroform (10 ml) was added 0.3 g (1.2 mmol) of m-chloroperbenzoic acid under ice-water cooling, and the mixture was stirred at room temperature for 3 hours. A potassium carbonate aqueous solution and then a sodium sulfite aqueous solution were added, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crystals were washed with ether, 3-iodo ^{-N 1 - [4- (5-} n- heptafluoropropyl tetrazol-1-yl) ^{-2-methylphenyl]} -N 2 - (1,1-dimethyl - 0.37 g of 2-methylsulfonylethyl) phthalamide was obtained.
Yield: 93%
Physical property: Melting point 141-142 ° C

シクロプロピルアミン１．６５ｇ（２９ミリモル）のテトラヒドロフラン５０ｍｌ溶液に、トリエチルアミン３．３５ｇ（３３ミリモル）を加え、氷水冷下、３−メチル−４−ニトロベンゾイルクロリド５．０ｇ（２８ミリモル）を滴下した。室温に戻し、１２時間攪拌した後、反応溶液を氷水中に注ぎ、酢酸エチルで抽出した。有機層を無水硫酸マグネシウムで乾燥した後、減圧濃縮して目的物４．７ｇを得た。このものは精製せずに次の反応に用いた。 Example 3 N ² - (1,1-dimethyl-2-methylthioethyl) -3-iodo -N ¹ - [4- (-5- 1- cyclopropyl tetrazolyl) -2-methylphenyl] phthalamide (Compound No.4- 1) Production (3-1) Production of N-cyclopropyl-3-methyl-4-nitrobenzamide

To a solution of 1.65 g (29 mmol) of cyclopropylamine in 50 ml of tetrahydrofuran was added 3.35 g (33 mmol) of triethylamine, and 5.0 g (28 mmol) of 3-methyl-4-nitrobenzoyl chloride was added dropwise under cooling with ice water. . After returning to room temperature and stirring for 12 hours, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 4.7 g of the desired product. This was used in the next reaction without purification.

Ｎ−シクロプロピル−３−メチル−４−ニトロベンズアミド４．７ｇ（２１ミリモル）のトルエン４０ｍｌとジオキサン４ｍｌ混合溶液に、五塩化燐６．３ｇ（３０ミリモル）を加え、３時間加熱還流した。反応混合物を減圧濃縮した後ＤＭＦ３０ｍｌに溶かし、アジ化ナトリウム２．８ｇ（４３ミリモル）のＤＭＦ溶液にゆっくり滴下した。５時間攪拌した後、反応溶液を水に注ぎ、酢酸エチルで抽出した。有機層を無水硫酸マグネシウムで乾燥した後、減圧濃縮し、残渣をエーテルでろ過し目的物３．７ｇを得た。
収率：７１％
物性：［^１ＨＮＭＲ，ＣＤＣｌ_３，δ値（ｐｐｍ）］
８．１５（ｄ，１Ｈ），８．０２（ｓ，１Ｈ），７．９７（ｄ，１Ｈ），
３．７６（ｍ，１Ｈ），２．７１（ｓ，３Ｈ），１．３９（ｍ，４Ｈ）． (3-2) Production of 4- (1-cyclopropyltetrazol-5-yl) -2-methylnitrobenzene

To a mixed solution of 4.7 g (21 mmol) of N-cyclopropyl-3-methyl-4-nitrobenzamide in 40 ml of toluene and 4 ml of dioxane, 6.3 g (30 mmol) of phosphorus pentachloride was added and heated to reflux for 3 hours. The reaction mixture was concentrated under reduced pressure, dissolved in 30 ml of DMF, and slowly added dropwise to a solution of 2.8 g (43 mmol) of sodium azide in DMF. After stirring for 5 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was filtered with ether to obtain 3.7 g of the desired product.
Yield: 71%
Physical properties: [ ¹ HNMR, CDCl ₃ , δ value (ppm)]
8.15 (d, 1H), 8.02 (s, 1H), 7.97 (d, 1H),
3.76 (m, 1H), 2.71 (s, 3H), 1.39 (m, 4H).

４−（１−シクロプロピルテトラゾール−５−イル）−２−メチルニトロベンゼン１．６ｇ（６．５ミリモル）のエタノール７０ｍｌ溶液に、５％パラジウム炭素０．４ｇを加え、３気圧の水素下で一晩撹拌を行った。反応液をろ過し、減圧濃縮し、残渣をシリカゲルカラムクロマトグラフィーで精製して、目的物１．０ｇを得た。
収率：７２％
物性：融点 １３９−１４０℃ (3-3) Production of 4- (1-cyclopropyltetrazol-5-yl) -2-methylaniline (Compound No. 8-1)

To a solution of 1.6 g (6.5 mmol) of 4- (1-cyclopropyltetrazol-5-yl) -2-methylnitrobenzene in 70 ml of ethanol was added 0.4 g of 5% palladium carbon, and the mixture was added under 3 atm of hydrogen. Stirring was performed overnight. The reaction solution was filtered, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1.0 g of the desired product.
Yield: 72%
Physical property: Melting point 139-140 ° C

３−ヨード−Ｎ−（１，１−ジメチル−２−メチルチオエチル）フタルイソイミド０．８ｇ（２．３ミリモル）をアセトニトリル１０ｍｌに溶かし、４−（１−シクロプロピルテトラゾール−５−イル）−２−メチルアニリン０．５０ｇ（２．３ミリモル）、トリフルオロ酢酸１０ｍｇを加え、室温下で１２時間撹拌した。析出した結晶を濾過しアセトニトリルで洗浄して、目的物１．３０ｇを得た。
収率：９９％
物性：融点 １３１−１３２℃ (3-4) N ² - (1,1-dimethyl-2-methylthioethyl) -3-iodo -N ¹ - [4- (-5- 1- cyclopropyl tetrazolyl) -2-methylphenyl] phthalamide ( Production of Compound No. 4-1)

3-Iodo-N- (1,1-dimethyl-2-methylthioethyl) phthalisoimide 0.8 g (2.3 mmol) was dissolved in 10 ml of acetonitrile, and 4- (1-cyclopropyltetrazol-5-yl)- 0.50 g (2.3 mmol) of 2-methylaniline and 10 mg of trifluoroacetic acid were added, and the mixture was stirred at room temperature for 12 hours. The precipitated crystals were filtered and washed with acetonitrile to obtain 1.30 g of the desired product.
Yield: 99%
Physical property: Melting point 131-132 ° C

Representative compounds of the phthalamide represented by the general formula (I) of the present invention that can be produced in the same manner as in the examples are shown in Tables 1 to 4 and represented by the general formula (III) that is an intermediate thereof. Although typical compounds of aniline derivatives are exemplified in Tables 5 to 8, the present invention is not limited to these. In the table, physical properties indicate melting points, “Me” represents a methyl group, “Et” represents an ethyl group, “Pr” represents a propyl group, “Ph” represents a phenyl group, and “c-” represents cyclo. Show.
Table 9 shows NMR data for some of the compounds whose physical properties are not described in Tables 5 to 8.

Although the typical formulation example and test example of this invention are shown below, this invention is not limited to these.
In the preparation examples, “parts” means “parts by weight”.
Formulation Example 1
Compounds listed in Tables 1 to 4 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above components are uniformly mixed and dissolved to prepare an emulsion.
Formulation Example 2
Compounds listed in Tables 1 to 4 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is uniformly mixed and pulverized to obtain a powder.

Formulation Example 3
Compounds listed in Tables 1 to 4 5 parts Mixed powder of bentonite and clay 90 parts Calcium lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules And
Formulation Example 4
Compounds listed in Tables 1 to 4 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above is mixed and ground uniformly to obtain a wettable powder.

Test Example 1 Insecticidal test against Plutella xylostella Sponge seedlings are allowed to lay eggs and lay eggs, and after 2 days of release, Chinese cypress seedlings with spawning eggs are treated with the compounds listed in Tables 1 to 4 as active ingredients. Was immersed in a chemical solution diluted to 50 ppm for about 30 seconds, air-dried, and then allowed to stand in a thermostatic chamber at 25 ° C. Six days after immersion in the chemical solution, the number of hatching insects was investigated, the death rate was calculated according to the following formula, and the determination was made according to the following criteria. 1 ward, 10 heads, 3 systems.
[Equation 1]
Number of hatched insects in the untreated area-Number of hatched insects in the treated area Death rate (%) = ―――――――――――――――――― × 100
Number of hatchlings in untreated area

Judgment criteria. A ... 100% death rate
B ... 99% to 90% death rate
C ... Death rate 89% -80%
D ... Death rate 79% -50%

  As a result of the above test, the compounds showing the insecticidal activity of A are 1-4, 1-5, 1-6, 1-13, 1-15, 1-16, 1-17, 1-18, 1-19, 1-21, 2-4, 2-6, 2-7, 2-10, 2-12, 2-13, 2-15, 2-16, 2-18, 3-7, 3-8, 3- 9, 3-13, 3-14, 3-15, 3-16, 3-18, 3-19, 3-20, 3-21, 3-22, 3-24, 3-25, 3-27, 3-28, 3-30, 3-31, 3-32, 3-33, 3-34, 3-36, 3-37, 3-39, 3-55, 3-57, 3-58, 3- 60, 4-4, 4-5, 4-7, 4-9.

Test Example 2 Insecticidal test against Spodoptera litura A cabbage leaf piece (cultivar: four seasons) is immersed in a chemical solution diluted to 500 ppm with a compound containing the compounds shown in Tables 1 to 4 for about 30 seconds. After putting it in a 9 cm plastic petri dish and inoculating Spodoptera litura larvae, they were covered and left in a constant temperature room at 25 ° C. The number of live and dead insects was investigated 8 days after the inoculation, and the death rate was calculated according to the following formula. 1 ward, 10 heads, 3 systems.
[Equation 2]
Number of live insects in the untreated area-Number of live insects in the treated area Death rate (%) = ―――――――――――――――――― × 100
Number of live insects in the untreated area

  As a result of the above test, the compounds showing the insecticidal activity of A are 1-4, 1-5, 1-6, 1-13, 1-15, 1-16, 1-17, 1-18, 1-19, 1-21, 2-7, 2-10, 2-12, 2-13, 2-15, 3-7, 3-8, 3-9, 3-13, 3-14, 3-15, 3- 16, 3-18, 3-19, 3-20, 3-21, 3-22, 3-24, 3-25, 3-27, 3-28, 3-30, 3-31, 3-32, 3-33, 3-34, 3-36, 3-37, 3-39, 3-55, 3-57, 3-58, 3-60, and 4-7.

Test Example 3 Insecticidal test against adoxophyes sp. The tea leaves are immersed for about 30 seconds in a chemical solution prepared by diluting drugs containing the compounds shown in Tables 1 to 4 as active ingredients to 500 ppm. After putting it in a plastic petri dish and inoculating chanokakumonmon larvae, it was left in a constant temperature room at 25 ° C. and 70% humidity. The number of live and dead insects was investigated 8 days after the inoculation, and the determination was made in the same manner as in Test Example 2. 1 ward, 10 heads, 3 systems.

  As a result of the above test, the compounds showing the insecticidal activity of A are 1-4, 1-13, 1-15, 1-16, 1-17, 1-18, 2-7, 2-9, 2-13, 2-15, 2-18, 3-7, 3-8, 3-9, 3-13, 3-14, 3-18, 3-19, 3-20, 3-21, 3-22, 3- 24, 3-25, 3-27, 3-28, 3-31, 3-32, 3-33, 3-34, 3-39, 3-55, 3-57, 3-58, 3-60, 4-7 and 4-9.

Claims (8)

Formula (I)

{Wherein R ¹ represents a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a halo C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group or a halo. A C ₂ -C ₆ alkynyl group;
R ² and R ³ may be the same or different and are a hydrogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a halo C ₂ -C ₆ alkenyl group, It shows the C ₂ -C ₆ alkynyl group or a halo C ₂ -C ₆ alkynyl group.
R ⁴ and R ⁵ may be the same or different, and are a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ alkylcarbonyl group, a halo A C ₁ -C ₆ alkylcarbonyl group, a C ₁ -C ₆ alkoxycarbonyl group or a halo C ₁ -C ₆ alkoxycarbonyl group is shown.
A is A-1

Wherein Z is a hydrogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₁₀ alkyl group, a C ₂ -C ₆ alkenyl group, a halo C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group Halo C ₂ -C ₆ alkynyl group, C ₃ -C ₆ cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group, phenyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ A substituted phenyl group having one or more substituents selected from a -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group and a halo C ₁ -C ₆ alkoxy group, a heterocyclic group, or It may be the same or different and is from a halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group and halo C ₁ -C ₆ alkoxy group A substituted heterocyclic group having one or more selected substituents is shown.)
Or A-2

(Wherein Z is the same as above) represents a tetrazolyl group.
X is a halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, a halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group or halo C ₁ -C ₆ alkylsulfonyl group M represents an integer of 0 to 4.
Y is a halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, a halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group or halo C ₁ -C ₆ alkylsulfonyl group P represents an integer of 0 to 4.
n shows the integer of 0-2. } Or a salt thereof. R ¹ represents a C ₁ -C ₆ alkyl group may be R ² and R ³ are the same or different, a hydrogen atom, C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group, R ⁴ And R ⁵ represents a hydrogen atom, A represents A-1 or A-2, Z represents a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₁₀ alkyl group, a C ₃ -C ₆ cycloalkyl group, a halo, C ₃ -C ₆ cycloalkyl group, phenyl group or the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ A substituted phenyl group having one or more substituents selected from an alkoxy group and a halo C ₁ -C ₆ alkoxy group, X represents a halogen atom or a C ₁ -C ₆ haloalkyl group, and m represents 1 or 2 Y represents a halogen atom, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group, p represents an integer of 0 to 2, and n represents an integer of 0 to 2 The phthalamide derivative according to claim 1 or a salt thereof. R ¹ represents a C ₁ -C ₆ alkyl group, R ² and R ³ may be the same or different, represent a hydrogen atom or a C ₁ -C ₆ alkyl group, R ⁴ and R ⁵ represent a hydrogen atom, A represents A-1 or A-2, Z represents a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₁₀ alkyl group, a C ₃ -C ₆ cycloalkyl group, a halo C ₃ -C ₆ cycloalkyl group, A phenyl group or a substituted phenyl group which may be the same or different and has one or more substituents selected from a halogen atom, a halo C ₁ -C ₆ alkyl group and a halo C ₁ -C ₆ alkoxy group; represents an atomic, m represents 1, Y represents a halogen atom or a C ₁ -C ₆ alkyl group, p represents 1, phthalamide derivative or according to claim 1 wherein n represents an integer of 0 to 2 salts. General formula (III)

{Wherein R ⁵ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ alkylcarbonyl group, a halo C ₁ -C ₆ alkyl A carbonyl group, a C ₁ -C ₆ alkoxycarbonyl group or a halo C ₁ -C ₆ alkoxycarbonyl group;
A is A-1

Wherein Z is a hydrogen atom, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₁₀ alkyl group, a C ₂ -C ₆ alkenyl group, a halo C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group Halo C ₂ -C ₆ alkynyl group, C ₃ -C ₆ cycloalkyl group, halo C ₃ -C ₆ cycloalkyl group, phenyl group, which may be the same or different, halogen atom, cyano group, nitro group, C ₁ A substituted phenyl group having one or more substituents selected from a -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group and a halo C ₁ -C ₆ alkoxy group, a heterocyclic group, or It may be the same or different and is from a halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group and halo C ₁ -C ₆ alkoxy group A substituted heterocyclic group having one or more selected substituents is shown.)
Or A-2

(Wherein Z is the same as above) represents a tetrazolyl group.
Y is a halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio groups, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group or a halo (C ₁ -C ₆ alkyl) sulfonyl group P represents an integer of 0 to 4. } Or an salt thereof. R ⁵ represents a hydrogen atom, A represents A-1 or A-2, Z represents a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₁₀ alkyl group, a C ₃ -C ₆ cycloalkyl group, a halo C _3- C ₆ cycloalkyl group, phenyl group or the same or different, halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy And a substituted phenyl group having one or more substituents selected from a halo C ₁ -C ₆ alkoxy group, and Y represents a halogen atom, a C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkyl group The aniline derivative or salt thereof according to claim 3, wherein p represents an integer of 0 to 2. R ⁵ represents a hydrogen atom, A represents A-1 or A-2, Z is C ₁ -C ₆ alkyl group, halo C ₁ -C ₁₀ alkyl group, C ₃ -C ₆ cycloalkyl group, halo C _{A 3-} C ₆ cycloalkyl group, a phenyl group or a substituent having one or more substituents which may be the same or different and are selected from a halogen atom, a halo C ₁ -C ₆ alkyl group and a halo C ₁ -C ₆ alkoxy group The aniline derivative or a salt thereof according to claim 3, wherein Y represents a phenyl group, Y represents a halogen atom or a C ₁ -C ₆ alkyl group, and p represents 1.   An insecticide for agricultural and horticultural use comprising the phthalamide derivative according to any one of claims 1 to 3 as an active ingredient.   A method for using an agricultural and horticultural insecticide, which comprises treating an effective amount of the agricultural and horticultural insecticide according to claim 7 on a target plant or soil in order to control pests from useful plants.