JP2006089469A - Optically active phthalamide derivative, insecticide for agriculture and horticulture and use thereof - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new insecticide having excellent preventive action as an insecticide for agriculture and horticulture, exerting excellent effects even when used as a mixture with another insecticide or the like. <P>SOLUTION: The optically active phthalamide derivative represented by general formula (I) [wherein, R<SP>1</SP>and R<SP>2</SP>are H, a (substituted) 1-6C alkyl or a 1-6C alkoxycarbonyl; R<SP>3</SP>is a 1-6C alkyl; A is H, an alkyl, an alkenyl, an alkynyl, a (substituted) phenoxyalkyl or the like; p is 0-4; q is 0-2; X is a halogen, CN, NH<SB>2</SB>, an alkyl, an alkenyl, an alkylthio or the like; m is 0-4; Y is H, a halogen, CN, NH<SB>2</SB>, an alkyl, a (substituted) phenyl or the like; n is 1-5; Z<SP>1</SP>and Z<SP>2</SP>are C-Y or N] and salts thereof are provided, and the insecticide for agriculture and horticulture comprises the derivative as an active ingredient. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to an optically active 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, in these conventional documents, only a part of the optically active substance having a racemate and a specific substituent is disclosed, and the optically active substance having a substituent of the present invention is a novel compound not described in the literature, It is not known to have excellent performance as an insecticide.
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 optically active phthalamide derivative represented by the general formula (I) of the present invention is a novel compound not described in the literature, The compound described in the literature shows an excellent insecticidal effect at a low dose, especially by treating it with soil, etc., and found that it is an excellent agricultural and horticultural insecticide showing a high absorption transfer action from the root, The present invention has been completed.

｛式中、Ｒ¹及びＲ²は同一又は異なっても良く、水素原子、C₁-C₆アルキル基、同一又は
異なっても良く、ハロゲン原子、C₁-C₆アルコキシ基、C₁-C₆アルキルチオ基、モノC₁-C₆
アルキルアミノ基又は同一若しくは異なっても良いジC₁-C₆アルキルアミノ基から選択さ
れる１以上の置換基を有する置換C₁-C₆アルキル基又はC₁-C₆アルコキシカルボニル基を示し、Ｒ³はC₁-C₆アルキル基を示す。 That is, the present invention relates to the general formula (I)

{Wherein R ¹ and R ² may be the same or different and may be a hydrogen atom, a C ₁ -C ₆ alkyl group, the same or different, a halogen atom, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylthio groups, mono C ₁ -C ₆
A substituted C ₁ -C ₆ alkyl group or a C ₁ -C ₆ alkoxycarbonyl group having 1 or more substituents selected from a good-di C ₁ -C ₆ alkylamino group which may alkylamino group or the same or different, R ³ represents a C ₁ -C ₆ alkyl group.

A is a hydrogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₃ -C ₆ alkenyl group, halo C ₃ -C ₆ alkenyl group, C ₃ -C ₆ alkynyl group, halo C ₃ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ alkyl group,
Halo C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, C _1- C ₆ alkylcarbonyl group, mono C ₁ -C ₆ alkylcarbamoyl group, same or different di C ₁ -C ₆ alkylcarbamoyl group, phenoxy C ₁ -C ₆ alkyl group, same or different, halogen atom , 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, halo C ₁ -C ₆ alkylthio Group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, Di-C ₁ -C ₆ alkylamino group, which may be the same or different, mono (halo C ₁ -C ₆ alkyl) amino A substituted phenoxy C ₁ -C ₆ alkyl group, a phenyl C ₁ -C ₆ alkyl group having one or more substituents selected from a group or a di (halo C ₁ -C ₆ alkyl) amino group which may be the same or different, or It may be the same or different and is a halogen atom, 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, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, a mono C ₁ -C ₆ alkylamino group, di-C ₁ -C ₆ alkylamino group which may be the same or different, mono (haloC ₁ -C ₆ alkyl) amino group or di (halo C _1- which may be the same or different A substituted group having one or more substituents selected from a C ₆ alkyl) amino group on the ring. An enyl C ₁ -C ₆ alkyl group is shown. p shows the integer of 0-4. q represents an integer of 0 to 2.

X may be the same or different, and is a halogen atom, cyano group, amino group, nitro group, C ₁ -C ₆
Alkyl group, halo C ₁ -C ₆ 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 ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, a halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group or, the same or different and may di C ₁ -C ₆ alkylamino group.

m shows the integer of 0-4. X can be combined with adjacent carbon atoms on the phenyl ring to form a condensed ring, which may be the same or different, and is a halogen atom, a C ₁ -C ₆ alkyl group, a 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, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group Halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C _1- which may be the same or different C ₆ alkylamino group, mono (halo C ₁ -C ₆ alkyl) amino group, same or different di (halo C ₁ -C ₆ alkyl) amino group, phenyl group, same or different, halogen atom , C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ al Alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different, mono (halo C ₁ -C ₆ alkyl) amino group or the same or different A substituted phenyl group having one or more substituents selected from di (halo C ₁ -C ₆ alkyl) amino groups, a heterocyclic group, or the same or different, halogen atom, 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, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ Alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl Group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di-C ₁ -C ₆ alkylamino group which may be the same or different, mono (halo C ₁ -C ₆ alkyl) amino group Alternatively, it may have one or more substituents selected from a substituted heterocyclic group having one or more substituents selected from di (halo C ₁ -C ₆ alkyl) amino groups which may be the same or different.

Y may be the same or different, and may be a hydrogen atom, halogen atom, cyano group, amino group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ 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, cyclo C ₃ -C ₆ alkyl group, halocyclo C ₃ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group , halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group,
Halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di-C ₁ -C ₆ alkylamino group which may be the same or different, tri-C ₁ -C ₆ alkylsilyl group which may be the same or different, phenyl group, which may be the same or different, halogen Atom, 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, halo C ₁ -C ₆ Alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group , the same or different and may di C ₁ -C ₆ alkylamino group, a mono (halo C ₁ -C ₆ alkyl ) Amino group or the same or different and may di (halo C ₁ -C ₆ alkyl) substituted phenyl group having one or more substituents selected from amino group, heterocyclic group or the same or different and may a halogen atom , 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, halo C ₁ -C ₆ alkylthio Group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, Selected from the same or different di-C ₁ -C ₆ alkylamino group, mono (halo C ₁ -C ₆ alkyl) amino group or the same or different di (halo C ₁ -C ₆ alkyl) amino group And a substituted heterocyclic group having one or more substituents.

n shows the integer of 1-5. Y can form a condensed ring together with adjacent carbon atoms on the phenyl ring, and the condensed rings may be the same or different, and may be a halogen atom, a C ₁ -C ₆ alkyl group, a 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, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group Halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different di C _1- C ₆ alkylamino group, mono (halo C ₁ -C ₆ alkyl) amino group, same or different di (halo C ₁ -C ₆ alkyl) amino group, phenyl group, same or different, halogen atom , C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ al Alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different, mono (halo C ₁ -C ₆ alkyl) amino group or the same or different A substituted phenyl group having one or more substituents selected from di (halo C ₁ -C ₆ alkyl) amino groups, a heterocyclic group, or the same or different, halogen atom, 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, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ Alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl Group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di-C ₁ -C ₆ alkylamino group which may be the same or different, mono (halo C ₁ -C ₆ alkyl) amino group Alternatively, it may have one or more substituents selected from a substituted heterocyclic group having one or more substituents selected from di (halo C ₁ -C ₆ alkyl) amino groups which may be the same or different.

Z ¹ and Z ² may be the same or different and each represents C—Y (wherein Y is the same as described above) or a nitrogen atom.
However, R ¹ and R ² simultaneously represent a hydrogen atom, R ³ represents a methyl group, X represents an iodine atom, m represents 1, Yn represents 2-methyl-4- [1,2,2, 2-tetrafluoro-1- (trifluoromethyl) ethyl] group, when p is 1 and q is 0, A excludes methyl and ethyl groups. }
The present invention relates to an agricultural and horticultural insecticide characterized by containing an optically active phthalamide derivative represented by the formula (1) or a salt thereof as an active ingredient, and a method for using the same.

  The optically active 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 line killing agents. Even when used in combination with insecticides, 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 optically active phthalamide derivative of the present invention, the “halogen atom” refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom. “C ₁ -C ₆ alkyl group” means a linear or branched alkyl group having 1 to 6 carbon atoms, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl. Group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, neopentyl group, n-hexyl group and the like. The “halo C ₁ -C ₆ alkyl 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. Fluoromethyl group, difluoromethyl group, perfluoroethyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, chloromethyl group, bromomethyl group, 1-bromoethyl group, 2,3- A dibromopropyl group etc. can be illustrated. "C ₁ -C ₆
"Alkoxy group" refers to a linear or branched alkoxy group having 1 to 6 carbon atoms, such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, s-butoxy. Group, t-butoxy group, n-pentyloxy group, isopentyloxy group, neopentyloxy group, n-hexyloxy group and the like.

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. The “C ₁ -C ₆ alkoxycarbonyl group” refers to a linear or branched alkoxycarbonyl group having 1 to 6 carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, iso A propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group, etc. can be illustrated. The “C ₁ -C ₆ alkylthio group” refers to a linear or branched alkylthio group having 1 to 6 carbon atoms, such as methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n- Examples include butylthio group, s-butylthio group, t-butylthio group, n-pentylthio group, isopentylthio group, n-hexylthio group and the like. The “C ₁ -C ₆ alkylsulfinyl group” refers to a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n Examples include -butylsulfinyl, s-butylsulfinyl, t-butylsulfinyl, n-pentylsulfinyl, isopentylsulfinyl, n-hexylsulfinyl and the like. The “C ₁ -C ₆ alkylsulfonyl group” means a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropyl Examples include a sulfonyl group, n-butylsulfonyl group, s-butylsulfonyl group, t-butylsulfonyl group, n-pentylsulfonyl group, isopentylsulfonyl group, n-hexylsulfonyl group and the like.

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, and a pyrazolyl group. Quinazoline, indole, indoline, chroman, isochroman, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzoxazole, Nzochiazoru, benzimidazole, can be exemplified indazole like.
Examples of the salt of the optically active 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 shu. Examples thereof include organic acid salts such as acid salts, methanesulfonate, benzenesulfonate, and paratoluenesulfonate, and salts with sodium ions, potassium ions, calcium ions, and the like.

In the optically active phthalamide derivative represented by the general formula (I) of the present invention, R ¹ and R ² are particularly preferably hydrogen atoms. R ³ is particularly preferably a methyl group. A is preferably a C ₁ -C ₆ alkyl group, and particularly preferably a methyl group or an ethyl group. p
Is preferably 1 or 2, particularly preferably 1. q is an integer of 0 to 2, preferably 1 or 2, and particularly preferably 2. X is preferably a halogen atom, and 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 C ₁ -C ₆ alkyl group, a halogen atom, a halo C ₁ -C ₆ alkyl group, or a halo C ₁ -C ₆ alkoxy group. n is preferably 2 or 3. Z ¹ and Z ² are particularly preferably CH.

（式中、Ｒ¹、Ｒ²、Ｒ³、Ａ、Ｘ、Ｙ、Ｚ¹、Ｚ²、ｐ、ｑ、ｍ及びｎは前記に同じくし、
ｈａｌはハロゲン原子を示す。） The absolute configuration of the optically active phthalamide derivative represented by the general formula (I) of the present invention is the (S) isomer, and can be produced, for example, by the production method illustrated below.
Manufacturing method 1.

(Wherein R ¹ , R ² , R ³ , A, X, Y, Z ¹ , Z ² , p, q, m and n are the same as above,
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, The phthalamide derivative represented by formula (I-1) is reacted with the halide represented by formula (IV) in the presence of a dehydrohalogenating agent and an inert solvent. By reacting the phthalamide derivative (I-2) with an oxidizing agent in the presence of an inert solvent, the phthalamide derivative represented by the general formula (I-2) is represented. Phthalamide derivatives can be produced. When R ¹ 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). 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 the reaction. For example, tetrahydrofuran, diethyl ether, methyl t-butyl ether, dioxane, chloroform, methylene chloride, chlorobenzene, toluene, acetonitrile, ethyl acetate And butyl acetate. 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 an 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.

(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. Amides, acids such as acetic acid, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and other inert solvents can be exemplified, and these inert solvents can 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.

(3). General formula (I-1) or (I-2) → General formula (I)
Examples of the inert solvent used in this reaction include halogenated hydrocarbons such as methylene chloride and chloroform, aromatic hydrocarbons such as toluene and xylene, and halogenated aromatic hydrocarbons such as fluorobenzene, chlorobenzene and dichlorobenzene. And 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.

（式中、Ｒ³、Ａ、Ｘ、ｐ、ｑ及びｍは前記に同じ。） The phthalisoimide derivative represented by the general formula (II) which is the raw material compound of the present invention is represented by the general formula (V) according to the production methods described in JP-A-11-240857 and JP-A-2001-131141. It can be produced as shown below from the optically active amines represented.

(Wherein R ³ , A, X, p, q and m are the same as above).

（式中、Ｒ³、Ａ、ｐ及びｑは前記に同じくし、Ｂｏｃはｔ−ブトキシカルボニル基を示
し、Ｍｓはメシル基を示す。）
一般式（VI）で表される光学活性アミノアルコール類をｔ−ブトキシカルボニル化して一般式（VII）で表されるカーバメート類とし、ついでメシル化して一般式（VIII）で表
されるスルホン酸エステル類とした後、チオール類と反応させ、一般式（IX）で表されるスルフィド類とし、ｑが０の場合は直接脱保護をすることによ目的の一般式（Ｖ）で表される光学活性アミン類を製造することができる。また、ｑが１又は２の場合は一般式（IX）で表されるスルフィド類の硫黄原子を酸化して一般式（Ｘ）で表されるスルホキシド類又はスルホン類とした後、脱保護することにより目的の一般式（Ｖ）で表される光学活性アミン類を製造することができる。 The optically active amines represented by the general formula (V) can be obtained from optically active amino alcohols according to known methods (for example, Tetrahedron Lett., 1989, Vol. 30, p. 2653). It can manufacture with the manufacturing method to do.

(Wherein R ³ , A, p and q are the same as above, Boc represents a t-butoxycarbonyl group, and Ms represents a mesyl group.)
Optically active amino alcohols represented by the general formula (VI) are t-butoxycarbonylated to form carbamates represented by the general formula (VII), and then mesylated to form a sulfonic acid ester represented by the general formula (VIII). Then, it is reacted with a thiol to obtain a sulfide represented by the general formula (IX), and when q is 0, by directly deprotecting the optical compound represented by the general formula (V) Active amines can be produced. In addition, when q is 1 or 2, the sulfur atom of the sulfide represented by the general formula (IX) is oxidized to form a sulfoxide or sulfone represented by the general formula (X), and then deprotected. Thus, the target optically active amine represented by the general formula (V) can be produced.

The agricultural and horticultural insecticides containing the optically active phthalamide derivative represented by the general formula (I) of the present invention as an active ingredient are various agricultural and forestry, horticultural and stored grain pests that harm paddy rice, fruit trees, vegetables, other crops and flowers. Suitable for pest control such as house pests, hygiene pests, nematodes, etc. Grapholita molesta, Leguminvora glycinivorella, Olethreutes mori, Caloptilia thevivora, Caloptilia zachrysa
), Golden moth, Phyllonorycter ringoniella, Spulerrina astaurota, Piers rapae crucivora, Heliothis sp. , Carposina niponensis, Chilo suppressalis, Cnaphalocrocis medinalis, Ephestia elutelia, Glyphodes pyloalis, dia parata, gua P , Lepidoptera such as SesamIa inferens, Spodoptera litura, Spodoptera exigua,

Leafhopper leafhopper (Macrosteles fascifrons), Leafhopper leafhopper (Nephotettix cincticeps), Green planthopper (Nilaparvata lugens), White-footed planthopper (Sogatella furcifera)
), Citrus lice (Diaphorina citri), white lice (Aleurolobus taonabae), white lice (Bemisia tabaci), white lice (Trialeurodes vaporariorum), black-headed aphids (Lipaphis erysimi), peach aphids (Myzus peresica) Hemiptera: Pulvinaria aurantii, Pseudaonidia duplex, Pterudaonidia duplex, Comstockaspis perniciosa, Unaspis yanonensis, and other species, Pratylenchus sp. rufocuprea), bean scallop (Popilla japonica), tobacco beetle (Lasioderma serricorne), slatted beetle (Lyctus brunneus), Epilachna vigintioctopunctata, azuki beetle (Callosobruchus chinensis), saisai Caterpillars (Listroderes costirostris), weevil (Sitophilus zeamais), cotton weevil (Anthonomus grandis grandis), rice weevil (Lissorhoptrus oryzophilus), cucumber weevil (Aulacophora femoralis), rice croaker (Oulema oryzae) , Coleoptera pests such as Colorado potato beetle (Leptinotarsa decemlineata), Mexican beetle (Epilachna varivestis), corn rootworms (Diabrotica sp.),

Flyfly (Dacus (Zeugodacus) cucurbitae), citrus fruit fly (Dacus (Bactrocera) dorsalis), wing fly (Agromyza oryzae), onion fly (Delia antiqua), fly fly (Dalia platura), soybean flies (Asphon)
mestica), Diptera pests such as Culex pipiens pipiens, Pratylenchus coffeae, Glabodera rostchiensis, Meloidogyne sp., Tylenchulus semip Pesticides such as Aphelenchus avenae and Aphelenchoides ritzemabosi
, Kanzawa spider mites (Tetranychus kanzawaI Kishida), urticae mites (Tetranychus urticae Koch), Chinese spider mites (Acaphylla theae), citrus spider mites (Aculops pelekassi), Chinese spider ticks (Calacarus carinatus), pear spider mites (Epit)
It has a strong insecticidal effect against mite-like pests.

Furthermore, the agricultural and horticultural insecticides containing the optically active phthalamide derivative represented by the general formula (I) of the present invention as an active ingredient are the termites of the Rhinotermitidae (Coptotermes formosanus Shiraki) and the Yamato termites (Reticulitermessperatus ( Kolbe)
), Reticulitermes hesperus, Reticulitermes tibialis, Reticulitermes flavipes, etc. in North America, Reticulitermes lucifugus, Reticulitermes santonensis, etc. inhabit the Mediterranean coast, homes, building materials, furniture, leather, etc., such as formosanus (Shiraki)), dairy termites (Cryptotermes domesticus (Haviland)) and termites (Termopsidae) of Hodotermopsis jzponica (Holmgren) It has a remarkable ant killing effect at a low dose against all white ants that harm vinyl processed products, electric wires and cables. 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 with a low drug dose It has an effect.

The agricultural and horticultural insecticide containing the optically active phthalamide derivative represented by the general formula (I) of the present invention as an active ingredient is the above-mentioned pest that causes damage to paddy field crops, field crops, fruit trees, vegetables, other crops, flowers, etc. It has a remarkable control effect on the plant, so that it is possible to raise seedlings, paddy fields, fields, fruit trees, vegetables, other crops before the occurrence of the pests or at the time when the occurrence of the pests is confirmed, according to the time when the occurrence of the pests is predicted. The desired effect of the agricultural and horticultural insecticide of the present invention can be achieved by treating the seeds such as flower buds, paddy water, stalks and leaves, or a cultivation carrier such as soil. Among them, it is treated with seedling soil such as crops and 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 using the so-called osmotic transfer property by making it a preferred form of use. In recent years, genetically modified crops (herbicide-tolerant crops, pest-resistant crops incorporating insecticidal protein production genes, disease-resistant crops incorporating resistance-inducing substance production genes against disease, improved taste crops, preserved crops, yield Improved crops, etc.), insect pheromones (communication agents for oysters and moths, 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 systematically.

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) , Peach, plum, yellow peach, walnut, chestnut, almond, banana, strawberry, etc.), leaf and fruit vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, leek, pepper, eggplant, pepper, etc.), root vegetables ( Carrots, potatoes, sweet potatoes, taros, radishes, lotus roots, turnips, burdock, garlic, etc.), crops for processing (salmon, hemp, beet, hops, sugar cane, sugar beet, olives, rubber, coffee, tobacco, tea, etc.), cucumbers (Pumpkin, cucumber, cucumber, watermelon, melon, etc.), pasture (orchardgrass, 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.).

  Furthermore, the agricultural and horticultural insecticide of the present invention can also be used for genetically modified crops. Genetically modified crops include all plant species that incorporate useful properties using genetic engineering techniques. Examples of the genetically modified crops include cereals (wheat, rice), corn, soybeans, potatoes, straw, tobacco, rapeseed, fruit trees (apples, pears, citrus, grapes, etc.), and particularly important ones are corn , Soybeans, potatoes, straw, tobacco, rapeseed. Useful properties acquired by these crops include excellent growth; tolerance at high and low temperatures; tolerance in drought, high moisture, and salty soil conditions; improved flowering performance; ease of harvesting; High yield; high quality and / or high nutritional value of the harvest; storage stability and / or processability of the harvest, etc., and more important characteristics include pests, mites, phytopathogenic fungi, bacteria, viruses Resistance to pests and the like and resistance to certain herbicides. Specifically, toxins produced in plants, especially genetic material from Bacillus thuringiensis (e.g., genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab , Substances brought by Cry3Bb, CryIF and their hybrids, see "BT plants" below)), and the protection from pests, mites, nematodes, worms, etc., and systemic acquired resistance (SAR) , Systemin, phytoalexin, elicitor, resistance genes, and proteins and toxins expressed thereby improve the defense against plant pathogens, bacteria, viruses and the like.

Furthermore, the acquisition of tolerance to certain herbicides can be mentioned, and examples of herbicides include imidazolinone, sulfonylurea, glyphosate, and phosphinotricin (for example, PAT gene). These genes that express the desired properties can be combined with each other and incorporated into the recombinant crop. Genetically modified crops with these characteristics are already commercially available in crops such as corn, straw, soybeans, and potatoes. Examples of “BT plants” include YIELD GARD (corn, pod, soybean), Knock Out (corn), StarLink (corn), Bollgard (ｃｏ), Nucotn (棉), New Leaf (potato), etc. As an example of herbicide-tolerant crops, Rou
ndup Ready (glufosate tolerance: corn, straw, soybean), Libert
y Link (phosphinothricin resistance: rapeseed), IMI (imidazolinone resistance), ST
It is marketed under trade names such as S (sulfonylurea resistance: corn). The herbicide-tolerant crops described above include those that have been cultivated by conventional methods, and are marketed under the trade name Clearfield (corn). Of course, the agricultural and horticultural insecticide of the present invention has characteristics that are currently being developed or will be developed in the future, and can be applied to plant varieties and seeds that will enter the market in the future.

The insecticide for agricultural and horticultural use according to the present invention is used as it is to control various pests, or appropriately diluted with water or the like, or suspended in an amount effective for controlling the pests or nematodes. For example, for pests and nematodes occurring in fruit trees, cereals, vegetables, etc., in addition to spraying on the foliage, seeds are immersed in drugs, seeds such as seed dressing Treatment, soil all layer mixing, crop application, floor soil mixing, cell seedling treatment, planting hole treatment, plant base treatment, rice box treatment, water surface application, etc. You can also. In addition, it can be used for 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 of immersing seeds in a liquid state without diluting or diluting a liquid or solid preparation and infiltrating the drug, mixing the solid preparation with seeds, treating with powder Examples thereof include a method of adhering to the surface of seeds, a method of coating on seeds by admixing with an adhesive carrier such as resin and polymer, and a method of spraying around seeds at the same time as planting.
The “seed” for performing the seed treatment means a plant body at an early stage of cultivation used for plant propagation. For example, in addition to 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. It may be a molecular substance, rock wool, glass wool, wood chip, bark or the like.

As a spraying method to crop foliage or 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 application methods to 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 paddy rice to a seedling box, the dosage form may vary depending on the time of application such as application at seeding, application at greening period, application at transplanting, etc. Apply by mold. It can also be applied by mixing with cultivating soil, and it can be mixed with cultivating soil and powder, granulated wettable powder or granules, for example, mixed with floor soil, mixed with covering soil, mixed into the entire cultivated soil and the like. Simply, the soil and various preparations may be applied alternately in layers.
As an application method to paddy fields, solid preparations such as jumbo agents, pack agents, 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 preparation 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 inlet or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.

In a field crop, it can be processed to a seed or a cultivation carrier close to a 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 a plant source of a plant being cultivated is suitable. It is possible to perform spraying treatment using a granule or irrigation treatment in a liquid of a drug diluted or not diluted in water. 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 preferable. 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 optically active phthalamide derivative represented by the general formula (I) is dissolved, separated, suspended, mixed by blending these in a suitable inert carrier or, if necessary, together with an auxiliary agent in a suitable ratio. It may be used after being impregnated, adsorbed or adhered and formulated into an appropriate dosage form such as a flowable, emulsion, liquid, wettable powder, wettable powder, granule, powder, tablet, or pack.

  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, dibuty) Phthalate, dioctyl phthalate - DOO), 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 or in combination with two or more kinds of auxiliary agents. It is also possible not to use.
For emulsification, dispersion, solubilization and / or wetting of 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, methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl alcohol, pine oil, coconut oil, bentonite, lignin sulfonate, etc. are used for the purpose of dispersion stabilization of the active ingredient compound, adhesion 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% by weight is appropriate.
The agricultural and horticultural insecticide of the present invention is a crop in which the occurrence of the pest is predicted in an amount effective for controlling the pest as it is, or appropriately diluted with water or suspended in order to control various pests or 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 ares depending on 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 control period, 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, nematicides used for such purposes include, for example, etion, trichlorfone, methamidophos, acephate, dichlorvos, mevinphos, monocrotophos, malathion, dimethoate, formothion, mecarbam, bamidthione, thiomethone. , 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), azadilactin, rotenone, hydroxypropyl starch, Examples of agricultural and horticultural insecticides such as levamisole hydrochloride, metam sodium, morantel tartrate, dazomet, trichlamide, pastria, monacrosporium fimatopagum, acaricide, nematicide,

Examples of agricultural and horticultural fungicides to be used for the same purpose include sulfur, lime sulfur mixture, 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 pox virus (EPV), and 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. Messenger Microbial pesticide which is, 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, (Z) -8- Dodecenyl acetate, (Z) -11-tetradecenyl acetate Over DOO, (Z) -13-icosene-10-one, can be used in combination with pheromone such as 14-methyl-1-octadecene.

Ｌ−アラニノール１０．０ｇ（１３３ミリモル）のテトラヒドロフラン１００ｍｌ溶液に、トリエチルアミン１３．８ｇを加え、氷水冷下、二炭酸ジｔ−ブチル３０．０ｇ（１３７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（Ｓ）−（２−ヒドロキシ−１−メチルエチル）カルバミン酸ｔ−ブチル２４．０ｇを得た。
収率：定量的
物性：［¹ＨＮＭＲ，ＣＤＣｌ₃，δ値（ｐｐｍ）］
４．６２（ｂｒ，１Ｈ），３．７７（ｂｒ，１Ｈ），３．６４（ｂｒ，１Ｈ）,
３．４９（ｂｒ，１Ｈ），２．５４（ｂｒ，１Ｈ），１．４４（ｓ，９Ｈ）,
１．１４（ｄ，３Ｈ）． Although the typical example of this invention is illustrated below, this invention is not limited to these.
Example 1. (S)-3-iodo -N ¹ - (2-methyl-4-trifluoromethoxyphenyl) -N ² - (1-methyl-2-methylthioethyl) phthalamide (Compound No. I-4
2) Production (1-1) Production of t-butyl (S)-(2-hydroxy-1-methylethyl) carbamate

To a solution of 10.0 g (133 mmol) of L-alaninol in 100 ml of tetrahydrofuran was added 13.8 g of triethylamine, and 30.0 g (137 mmol) of di-t-butyl dicarbonate 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 24.0 g of t-butyl (S)-(2-hydroxy-1-methylethyl) carbamate.
Yield: Quantitative Physical property: [ ¹ HNMR, CDCl ₃ , δ value (ppm)]
4.62 (br, 1H), 3.77 (br, 1H), 3.64 (br, 1H),
3.49 (br, 1H), 2.54 (br, 1H), 1.44 (s, 9H),
1.14 (d, 3H).

（Ｓ）−（２−ヒドロキシ−１−メチルエチル）カルバミン酸ｔ−ブチル２４．０ｇ（１３７ミリモル）のテトラヒドロフラン１８０ｍｌ溶液に、トリエチルアミン１４．５ｇ（１４４ミリモル）を加え、氷水冷下、塩化メタンスルホニル１６．４ｇ（１４３ミリモル）を滴下した。室温に戻し、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。有機層を飽和塩化ナトリウム水溶液で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧濃縮してメタンスルホン酸（Ｓ）−２−（ｔ−ブトキシカルボニルアミノ）プロピル３４．０ｇを得た。
収率：９８．１％
物性：［¹ＨＮＭＲ，ＣＤＣｌ₃，δ値（ｐｐｍ）］
４．６１（ｂｒ，１Ｈ），４．２２（ｄｄ，１Ｈ），４．１４（ｄｄ，１Ｈ），
３．９６（ｂｒ，１Ｈ），３．０３（ｓ，３Ｈ），１．４４（ｓ，９Ｈ），
１．２３（ｄ，３Ｈ）． (1-2) Production of methanesulfonic acid (S) -2- (t-butoxycarbonylamino) propyl

To a solution of 24.0 g (137 mmol) of t-butyl (S)-(2-hydroxy-1-methylethyl) carbamate in 180 ml of tetrahydrofuran was added 14.5 g (144 mmol) of triethylamine, and methanesulfonyl chloride was cooled with ice water. 16.4 g (143 mmol) was added dropwise. After returning to room temperature and stirring for 5 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 34.0 g of methanesulfonic acid (S) -2- (t-butoxycarbonylamino) propyl.
Yield: 98.1%
Physical properties: [ ¹ HNMR, CDCl ₃ , δ value (ppm)]
4.61 (br, 1H), 4.22 (dd, 1H), 4.14 (dd, 1H),
3.96 (br, 1H), 3.03 (s, 3H), 1.44 (s, 9H),
1.23 (d, 3H).

メチルメルカプタンナトリウム水溶液（１５％）７３．０ｇ（１５６ミリモル）のエタノール１００ｍｌ溶液に、メタンスルホン酸（Ｓ）−２−（ｔ−ブトキシカルボニルアミノ）プロピル３４．０ｇ（１３４ミリモル）を加え、５時間加熱還流を行った。室温に戻し、減圧濃縮してエタノールを除いた後、残渣に水を加えて、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（Ｓ）−（１−メチル−２−メチルチオエチル）カルバミン酸ｔ−ブチル２１．０ｇを得た。
収率：７６．４％
物性：［¹ＨＮＭＲ，ＣＤＣｌ₃，δ値（ｐｐｍ）］
４．５９（ｂｒ，１Ｈ），３．８４（ｂｒ，１Ｈ），２．６５（ｄｄ，１Ｈ），
２．５４（ｄｄ，１Ｈ），２．１４（ｓ，３Ｈ），１．４４（ｓ，９Ｈ），
１．２１（ｄ，３Ｈ）． (1-3) Production of t-butyl (S)-(1-methyl-2-methylthioethyl) carbamate

34.0 g (134 mmol) of methanesulfonic acid (S) -2- (t-butoxycarbonylamino) propyl was added to a solution of 73.0 g (156 mmol) of aqueous methyl mercaptan sodium solution (15%) in 100 ml of ethanol for 5 hours. Heating to reflux was performed. After returning to room temperature and concentration under reduced pressure to remove ethanol, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 21.0 g of t-butyl (S)-(1-methyl-2-methylthioethyl) carbamate.
Yield: 76.4%
Physical properties: [ ¹ HNMR, CDCl ₃ , δ value (ppm)]
4.59 (br, 1H), 3.84 (br, 1H), 2.65 (dd, 1H),
2.54 (dd, 1H), 2.14 (s, 3H), 1.44 (s, 9H),
1.21 (d, 3H).

（Ｓ）−（１−メチル−２−メチルチオエチル）カルバミン酸ｔ−ブチル２１．０ｇ（１０２ミリモル）の酢酸エチル１５０ｍｌ溶液に、濃塩酸（３５％）３２．０ｇを滴下した。室温下で３時間攪拌した後、水を加えて酢酸エチルで洗浄した。水層を水酸化ナトリウムで塩基性にして、ｔ−ブチルメチルエーテルで抽出した。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（Ｓ）−１−メチル−２−メチルチオエチルアミン５．５ｇを得た。
収率：５１．４％
物性：［¹ＨＮＭＲ，ＣＤＣｌ₃，δ値（ｐｐｍ）］
４．９０（ｂｒ，２Ｈ），３．０７（ｍ，１Ｈ），２．５８（ｄｄ，１Ｈ），
２．３６（ｄｄ，１Ｈ），２．１０（ｓ，３Ｈ），1．１５（ｄ，３Ｈ）. (1-4) Production of (S) -1-methyl-2-methylthioethylamine

32.0 g of concentrated hydrochloric acid (35%) was added dropwise to a solution of 21.0 g (102 mmol) of t-butyl (S)-(1-methyl-2-methylthioethyl) carbamate in 150 ml of ethyl acetate. After stirring at room temperature for 3 hours, water was added and the mixture was washed with ethyl acetate. The aqueous layer was basified with sodium hydroxide and extracted with t-butyl methyl ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 5.5 g of (S) -1-methyl-2-methylthioethylamine.
Yield: 51.4%
Physical properties: [ ¹ HNMR, CDCl ₃ , δ value (ppm)]
4.90 (br, 2H), 3.07 (m, 1H), 2.58 (dd, 1H),
2.36 (dd, 1H), 2.10 (s, 3H), 1.15 (d, 3H).

３−ヨード無水フタル酸１４．４ｇ（５２．６ミリモル）のアセトニトリル１５０ｍｌ溶液に、（Ｓ）−１−メチル−２−メチルチオエチルアミン５．５ｇ（５２．４ミリモル）のアセトニトリル５０ｍｌ溶液をゆっくり滴下した。室温下で１２時間攪拌した後、析出した結晶を濾過しアセトニトリルで洗浄して、（Ｓ）−３−ヨード−Ｎ−（１−メチル−２−メチルチオエチル）フタルアミド酸７．０ｇを得た。
収率：３５．２％
物性：［¹ＨＮＭＲ，ＣＤＣｌ₃，δ値（ｐｐｍ）］
８．０１（ｄｄ，２Ｈ），７．１５（ｔ，１Ｈ），６．００（ｄ，１Ｈ），
４．４３（ｍ，１Ｈ），２．８８（ｄｄ，１Ｈ），２．６８（ｄｄ，１Ｈ），
２．１７（ｓ，３Ｈ），１．３７（ｄ，３Ｈ）. (1-5) Production of (S) -3-iodo-N- (1-methyl-2-methylthioethyl) phthalamic acid

A solution of 5.5 g (52.4 mmol) of (S) -1-methyl-2-methylthioethylamine in 50 ml of acetonitrile was slowly added dropwise to a solution of 14.4 g (52.6 mmol) of 3-iodophthalic anhydride in 150 ml of acetonitrile. . After stirring at room temperature for 12 hours, the precipitated crystals were filtered and washed with acetonitrile to obtain 7.0 g of (S) -3-iodo-N- (1-methyl-2-methylthioethyl) phthalamic acid.
Yield: 35.2%
Physical properties: [ ¹ HNMR, CDCl ₃ , δ value (ppm)]
8.01 (dd, 2H), 7.15 (t, 1H), 6.00 (d, 1H),
4.43 (m, 1H), 2.88 (dd, 1H), 2.68 (dd, 1H),
2.17 (s, 3H), 1.37 (d, 3H).

（Ｓ）−３−ヨード−Ｎ−（１−メチル−２−メチルチオエチル）フタルアミド酸０．８ｇ（２．１ミリモル）のｔ−ブチルメチルエーテル８ｍｌ懸濁液にトリフルオロ酢酸無水物０．６７ｇ（３．２ミリモル）を加え、室温下で２時間攪拌した。炭酸カリウム０．８８ｇ（６．４ミリモル）を溶かした氷水に、反応溶液をゆっくり注ぎ、酢酸エチルで抽出した。有機層を飽和塩化ナトリウム水溶液で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧濃縮し、粗製のイソイミドを得た。これをアセトニトリル１０ｍｌに溶かし、２−メチル−４−トリフルオロメトキシアニリン０．４０ｇ（２．２ミリモル）、トリフルオロ酢酸２滴を加え、室温下で１２時間攪拌した。析出した結晶を濾過しアセトニトリルで洗浄して、（Ｓ）−３−ヨード−Ｎ¹−（２−メチル−４−トリフルオロメトキシフェ
ニル）−Ｎ²−（１−メチル−２−メチルチオエチル）フタルアミド１．０ｇを得た。
収率：８８．２％
物性：［¹ＨＮＭＲ，ＣＤＣｌ₃，δ値（ｐｐｍ）］
８．３２（ｂｒ，１Ｈ），８．１３（ｄ，１Ｈ），７．９７（ｄ，１Ｈ），
７．７９（ｄ，１Ｈ）, ７．２２（ｔ，１Ｈ），７．０８（ｄ，１Ｈ），
７．０６（ｓ，１Ｈ），６．２０（ｄ，１Ｈ），４．３３（ｍ，１Ｈ），
２．６０（ｍ，２Ｈ）, ２．３３（ｓ，３Ｈ），１．９６（ｓ，３Ｈ），
１．２７（ｄ，３Ｈ）．
比旋光度：［α］_D ²⁰＝＋２．６１°（ｃ=１．０４、ＣＨＣｌ₃） (1-6) (S)-3-iodo -N ¹ - (2-methyl-4-trifluoromethoxyphenyl) -N ² - (1-methyl-2-methylthioethyl) phthalamide (Compound No.I-
42) Manufacture

To a suspension of 0.8 g (2.1 mmol) of (S) -3-iodo-N- (1-methyl-2-methylthioethyl) phthalamic acid in 8 ml of t-butyl methyl ether was added 0.67 g of trifluoroacetic anhydride. (3.2 mmol) was added and stirred at room temperature for 2 hours. The reaction solution was slowly poured into ice water containing 0.88 g (6.4 mmol) of potassium carbonate and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude isoimide. This was dissolved in 10 ml of acetonitrile, 0.40 g (2.2 mmol) of 2-methyl-4-trifluoromethoxyaniline and 2 drops of trifluoroacetic acid were added, and the mixture was stirred at room temperature for 12 hours. The precipitated crystals were filtered, washed with acetonitrile, (S)-3-iodo -N ¹ - (2-methyl-4-trifluoromethoxyphenyl) -N ² - (1-methyl-2-methylthioethyl) phthalamide 1.0 g was obtained.
Yield: 88.2%
Physical properties: [ ¹ HNMR, CDCl ₃ , δ value (ppm)]
8.32 (br, 1H), 8.13 (d, 1H), 7.97 (d, 1H),
7.79 (d, 1H), 7.22 (t, 1H), 7.08 (d, 1H),
7.06 (s, 1H), 6.20 (d, 1H), 4.33 (m, 1H),
2.60 (m, 2H), 2.33 (s, 3H), 1.96 (s, 3H),
1.27 (d, 3H).
Specific rotation: [α] _D ²⁰ = + 2.61 ° (c = 1.04, CHCl ₃ )

（Ｓ）−３−ヨード−Ｎ¹−（２−メチル−４−トリフルオロメトキシフェニル）−Ｎ²−（１−メチル−２−メチルチオエチル）フタルアミド０．３８ｇ（０．７０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０．４０ｇ（２．３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を加え、クロロホルムで抽出した。有機層を亜硫酸ナトリウム水溶液で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧濃縮した。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、（Ｓ）−３−ヨード−Ｎ¹−（２−メチル−４−トリフルオロメトキシフェニル）−Ｎ²−（１−メチル−２−メチルスルホニルエチル）フタルアミド０．２６ｇを得た。
収率：６４．９％
物性：［¹ＨＮＭＲ，ＣＤＣｌ₃，δ値（ｐｐｍ）］
８．０７（ｂｒ，１Ｈ），７．９７（ｍ，２Ｈ），７．７０（ｄ，１Ｈ），
７．２１（ｔ，１Ｈ），７．７０（ｍ，２Ｈ），６．６４（ｄ，１Ｈ），
４．６１（ｍ，１Ｈ），３．３７（ｄｄ，１Ｈ），３．１７（ｄｄ，１Ｈ），
２．７８（ｓ，３Ｈ），２．３２（ｓ，３Ｈ），１．５１（ｄ，３Ｈ）．
比旋光度：［α］_D ²⁰＝＋３．８０°（ｃ=１．０３、ＣＨＣｌ₃） Example 2 (S)-3-iodo -N ¹ - (2-methyl-4-trifluoromethoxyphenyl) -N ² - (1-methyl-2-methylsulfonyl-ethyl) phthalamide (Compound No
. I-44)

(S)-3-iodo -N ¹ - (2-methyl-4-trifluoromethoxyphenyl) -N ² - (1-methyl-2-methylthioethyl) phthalamide chloroform 10ml of 0.38 g (0.70 mmol) To the solution, 0.40 g (2.3 mmol) of m-chloroperbenzoic acid was added under ice-water cooling, and the mixture was stirred at room temperature for 3 hours. An aqueous potassium carbonate solution was added, and the mixture was extracted with chloroform. The organic layer was washed with an aqueous sodium sulfite solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, (S)-3-iodo -N ¹ - (2-methyl-4-trifluoromethoxyphenyl) -N ² - (1-methyl-2-methylsulfonyl-ethyl) phthalamide 0.26 g was obtained.
Yield: 64.9%
Physical properties: [ ¹ HNMR, CDCl ₃ , δ value (ppm)]
8.07 (br, 1H), 7.97 (m, 2H), 7.70 (d, 1H),
7.21 (t, 1H), 7.70 (m, 2H), 6.64 (d, 1H),
4.61 (m, 1H), 3.37 (dd, 1H), 3.17 (dd, 1H),
2.78 (s, 3H), 2.32 (s, 3H), 1.51 (d, 3H).
Specific rotation: [α] _D ²⁰ = + 3.80 ° (c = 1.03, CHCl ₃ )

The typical compounds of optically active phthalamides represented by the general formula (I) of the present invention that can be produced in the same manner as in Examples are exemplified in Tables 1 to 3, but the present invention is not limited to these. is not. In the table, the physical properties indicate melting point or logP, “Me” represents a methyl group, “Et” represents an ethyl group, “Pr” represents a propyl group, “−n” represents normal, and “−i” represents Iso is shown.
Table 4 shows NMR data and optical rotations of some compounds that are not listed in the physical properties in Tables 1 to 3.

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 and 2 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 and 2 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
5 parts of bentonite and clay mixed powder 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 and 2 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above is uniformly mixed and ground to obtain a wettable powder.

Test Example 1 Insecticidal test against Plutella xylostella Cabbage leaf pieces (variety: four seasons) cut out to a diameter of 7 cm were immersed in a chemical solution obtained by diluting a drug containing the compound of the present invention to 50 ppm for about 30 seconds. After air-drying, it was placed in a plastic petri dish with a diameter of 9 cm and 10 Koganaga 3rd instar larvae were inoculated. The number of live and dead insects was investigated 8 days after the inoculation, the death rate was calculated by the following formula, and the determination was made according to the following criteria.
Test conditions: 1 ward, 3 systems, 25 ° C, 50-60RH, 16L-8D long day conditions.
[Equation 1]
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

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 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-17, 1-18, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1- 26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34, 1-35, 1-36, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-47, 1-48, 1-49, 1-50, 1-51, 1-53, 1- 54, 1-56, 1-57, 1-59, 1-60, 1-62, 1-63, 1-64, 1-65, 1-66, 1-68, 1-72, 1-73, 1-74, 1-75, 1-76, 1-77, 1-7 1-79, 1-80, 1-81, 1-82, 1-83, 1-84, 1-85, 1-86, 1-87, 1-88, 1-89, 1-90, 1 -92, 1-93, 1-95, 1-96, 1-98, 1-99, 1-101, 1-102, 1-104, 1-105, 1-222, 1-224, 1-225 1-227, 1-231, 1-233, 1-234, 1-236, 1-237, 1-240, 1-241, 1-242, 1-243, 1-244, 1-245, 1 -246, 1-247, 1-248, 1-249, 1-250, 1-251, 1-252, 1-253, 1-254, 1-255, 1-256, 1-257, 1-260 1-263, 1-264, 1-266, 1-267, 1-269, 1-270, 1-272, 1-273, 1 275, 1-278, 1-281, 1-282, 1-283, 1-284, 1-285, 1-287, 1-288, 1-290, 1-291, 1-293, 1-306, 1-307, 1-308, 1-315, 1-317, 1-321, 1-323, 1-327, 1-328, 1-329, 1-330, 1-331, 1-332, 1- 333, 1-334, 1-335, 2-4, 2-5, 2-6, 2-10, 2-12, 2-13, 2-15, 2-16, 2-17, 2-18, 2-19, 2-20, 2-21, 2-27, 2-28, 2-30 and 2-32.

Test Example 2 Insecticidal test against Spodoptera litura A cabbage leaf piece (variety: four season harvest) cut out to a diameter of 7 cm was immersed in a chemical solution obtained by diluting a drug containing the compound of the present invention to 50 ppm for about 30 seconds. After air drying, it was placed in a plastic petri dish with a diameter of 9 cm and 10 second-infested larvae were inoculated. The number of live and dead insects was investigated 8 days after the inoculation, and the death rate was calculated in the same manner as in Test Example 1 for determination.
Test conditions: 1 ward, 3 systems, 25 ° C, 50-60RH, 16L-8D long day conditions.

As a result of the above test, the compounds showing the insecticidal activity of A are 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-17, 1-18, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1- 26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34, 1-35, 1-36, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-47, 1-48, 1-49, 1-50, 1-51, 1-53, 1- 54, 1-56, 1-57, 1-59, 1-60, 1-62, 1-63, 1-64, 1-65, 1-66, 1-68, 1-72, 1-73, 1-74, 1-75, 1-76, 1-77, 1-7 , 1-79,1-80,1-81,1-82,1-83
1-84, 1-85, 1-86, 1-87, 1-88, 1-89, 1-90, 1-92, 1-93, 1-95, 1-96, 1-98, 1 -99, 1-101, 1-102, 1-104, 1-105, 1-222, 1-225, 1-227, 1-231, 1-233, 1-234, 1-237, 1-240 1-241, 1-242, 1-243, 1-244, 1-245, 1-246, 1-247, 1-248, 1-249, 1-250, 1-251, 1-252, 1 -253, 1-254, 1-255, 1-256, 1-257, 1-260, 1-263, 1-264, 1-266, 1-269, 1-270, 1-272, 1-273 1-275, 1-278, 1-281, 1-282, 1-283, 1-284, 1-285, 1-2 7, 1-288, 1-290, 1-291, 1-293, 1-306, 1-307, 1-308, 1-321, 1-327, 1-328, 1-329, 1-331, 1-332, 1-333, 1-334, 1-335, 2-4, 2-5, 2-6, 2-10, 2-12, 2-13, 2-15, 2-16, 2- 17, 2-18, 2-28 and 2-30.

Test Example 3 Insecticide test against adoxophyes sp. The tea leaves were immersed in a chemical solution diluted with 50 ppm of a drug containing the compound of the present invention as an active ingredient for about 30 seconds. After air-drying, it was placed in a plastic petri dish with a diameter of 9 cm and inoculated with chinook leafworm larvae. The number of live and dead insects was investigated 8 days after the inoculation, and the death rate was calculated in the same manner as in Test Example 1 for determination.
Test conditions: 1 ward, 3 systems, 25 ° C, 50-60RH, 16L-8D long day conditions.

  As a result of the above test, the compounds showing the insecticidal activity of A are 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-17, 1-18, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1- 26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34, 1-35, 1-36, 1-38, 1-42, 1-44, 1-45, 1-47, 1-48, 1-50, 1-51, 1-53, 1-54, 1-56, 1-60, 1-62, 1-64, 1- 66, 1-68, 1-72, 1-73, 1-74, 1-75, 1-76, 1-77, 1-78, 1-79, 1-81, 1-82, 1-83, 1-84, 1-85, 1-86, 1-90, 1-9 1-93, 1-95, 1-96, 1-98, 1-99, 1-104, 1-105, 1-222, 1-224, 1-225, 1-227, 1-231, 1 -233, 1-234, 1-236, 1-237, 1-240, 1-241, 1-242, 1-243, 1-244, 1-245, 1-246, 1-247, 1-248 1-249, 1-250, 1-251, 1-252, 1-253, 1-254, 1-255, 1-256, 1-257, 1-260, 1-263, 1-264, 1 -266, 1-267, 1-269, 1-270, 1-278, 1-281, 1-282, 1-283, 1-284, 1-285, 1-287, 1-288, 1-290 , 1-291, 1-293, 1-307, 1-308, 1-327, 1-328, -329, 1-330, 1-332, 1-333, 1-334, 1-335, 2-10, 2-12, 2-13, 2-15, 2-16, 2-17, 2-28 2-30.

Comparative test Penetration migration test in Chinese cabbage Chinese cabbage seedlings (variety: Aichi) cultivated in a paper pot containing horticultural soil are placed in a plastic cylindrical container, and the compound of the present invention and comparative compound 1 (Japanese Patent Laid-Open No. 2001-131141)
10 ml of a drug solution diluted with 0.03, 0.1, 0.3, 1 or 3 ppm of a drug containing compound No. 216 as an active ingredient was inoculated, respectively, and inoculated with pearl moth hatched larvae. Four days after the inoculation, the number of surviving insects was examined, the death rate was calculated by the following formula, and the determination was made according to the following criteria. The results are shown in Table 5.
Test conditions: 1 ward, 3 systems, 25 ° C, 50-60RH, 16L-8D long day conditions.
[Equation 2]
Number of surviving insects in the untreated area-Number of surviving insects in the treated area Death rate = ―――――――――――――――――――― × 100
Number of live insects in the untreated area

Judgment criteria:
10 ... Death rate 91 to 100%, 9 ... Death rate 81 to 90%, 8 ... Death rate 71 to 80%,
7 ... Death rate 61-70%, 6 ... Death rate 51-60%, 5 ... Death rate 41-50%,
4 ... Dead rate 31-40%, 3 ... Dead rate 21-30%, 2 ... Dead rate 11-20%,
1 ... Death rate 1-10%, 0 ... Death rate 0%

その結果、本発明化合物は比較化合物に比べて明らに優位性を示した。

As a result, the compound of the present invention clearly showed an advantage over the comparative compound.

Comparative test 2. Test for controlling barley (Pieris rapae) by planting admixture treatment at cabbage planting time The present compound and comparative compound 1 (Compound No. 216 described in JP-A-2001-131141) at the time of planting cabbage seedling (variety: YR Harenori) in a field The compound containing the compound (2) as an active ingredient was mixed with a pothole (late April). The number of parasites was investigated 27 days after the planting, the control rate was calculated by the following formula, and the determination was made according to the criterion of Comparative Test 1. 1 ward 20 shares. The results are shown in Table 6.
[Equation 3]
Number of parasites in the untreated area − Rate of controlling the number of parasites in the treated area = ―――――――――――――――――――― × 100
Number of untreated parasites

その結果、本発明化合物は比較化合物に比べて明らに優位性を示した。

As a result, the compound of the present invention clearly showed an advantage over the comparative compound.

Comparative test 3. Test of controlling Japanese scallop by planting hole admixture at the time of cabbage planting Compound No. 216) was mixed with a pothole (late April). 30 days after planting, the upper third leaf was cut out and placed in a petri dish and inoculated with 10 third-instar larvae. Four days after the inoculation, the number of surviving insects was examined, and the death rate was calculated and judged in the same manner as in Comparative Test 1. 1 ward, 2 systems. The results are shown in Table 7.

その結果、本発明化合物は比較化合物に比べて明らに優位性を示した。

As a result, the compound of the present invention clearly showed an advantage over the comparative compound.

Comparative test 4. Test of controlling Japanese scallop by irrigation treatment with cabbage seedling box A drug containing the compound of the present invention and comparative compound 1 (compound No. 216 described in JP-A No. 2001-131141) as an active ingredient was diluted to a predetermined concentration. The obtained medicinal solution was irrigated at a rate of 4 ml / strain into cabbage seedlings (variety: YR Harenori) grown on a cell tray and planted in a field. Twenty days after the planting, the upper third leaf was cut out, placed in a petri dish, and inoculated with 10 third-instar larvae. Four days after the inoculation, the number of surviving insects was examined, and the death rate was calculated and judged in the same manner as in Comparative Test 1. 1 ward, 2 systems. The results are shown in Table 8.

その結果、本発明化合物は比較化合物に比べて明らに優位性を示した。

As a result, the compound of the present invention clearly showed an advantage over the comparative compound.

Comparative test 5. Peach aphid (Myzus persicae) control test (penetration transfer)
Compounds of the present invention (Compound Nos. 1-77 and 1-74) and Comparative Compound 2 (Japanese Patent Laid-Open No. 2001-1)
No. 31141, compound No. 101) and comparative compound 3 (Japanese Patent Laid-Open No. 2001-101)
The chemical | medical agent which uses the compound of the compound number 97 description of 131141 as an active ingredient was diluted to the predetermined density | concentration. The diluted solution was filled in a container in which pea (Pisum sativum) infested with peach aphid was planted. After 6 days of treatment, mortality was determined. The results are shown in Table 9. A mortality rate of 100% indicates that all test insects have been killed, and 0% indicates that none have been killed.

その結果、本発明化合物はそのラセミ体に比べて明らに優位性を示した。

As a result, the compound of the present invention clearly showed superiority over its racemic body.

Comparative test 6. Spodoptera exigua control test compound of the present invention (Compound No. 1-77) and Comparative Compound 2 (Japanese Patent Laid-Open No. 2001-131141)
A drug containing compound No. 101 described in the publication No. 1) as an active ingredient was diluted to a predetermined concentration. Cabbage (Brassica oleracea) leaf pieces were immersed in the diluted solution, and the leaf pieces were moistened and inoculated with white larvae. Seven days after treatment, mortality was determined. The results are shown in Table 10. A mortality rate of 100% indicates that all test insects have been killed, and 0% indicates that none have been killed.

その結果、本発明化合物はそのラセミ体に比べて明らに優位性を示した。

As a result, the compound of the present invention clearly showed superiority over its racemic body.

Comparative test 7. Mustard Beetle (Phaedon cochleariae) Control Test Compound of the present invention (Compound No. 1-77) and Comparative Compound 2 (Japanese Patent Laid-Open No. 2001-131141)
A drug containing compound No. 101 described in the publication No. 1) as an active ingredient was diluted to a predetermined concentration. Cabbage (Brassica oleracea) leaf pieces were immersed in the diluted solution, and mustard beetle larvae were inoculated while the leaf pieces were wet. Seven days after treatment, mortality was determined. The results are shown in Table 11. A mortality rate of 100% indicates that all test insects have been killed, and 0% indicates that none have been killed.

その結果、本発明化合物はそのラセミ体に比べて明らに優位性を示した。

As a result, the compound of the present invention clearly showed superiority over its racemic body.

Claims (6)

Formula (I)

{Wherein R ¹ and R ² may be the same or different and may be a hydrogen atom, a C ₁ -C ₆ alkyl group, the same or different, a halogen atom, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylthio groups, mono C ₁ -C ₆
A substituted C ₁ -C ₆ alkyl group or a C ₁ -C ₆ alkoxycarbonyl group having 1 or more substituents selected from a good-di C ₁ -C ₆ alkylamino group which may alkylamino group or the same or different, R ³ represents a C ₁ -C ₆ alkyl group.
A is a hydrogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₃ -C ₆ alkenyl group, halo C ₃ -C ₆ alkenyl group, C ₃ -C ₆ alkynyl group, halo C ₃ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkyl sulfinyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl sulfinyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ Alkylsulfonyl C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylcarbonyl group, mono C ₁ -C ₆ alkylcarbamoyl group, the same or different good di C ₁ -C ₆ alkylcarbamoyl group, a phenoxy C ₁ -C ₆ alkyl group, which may be identical or different, halogen atom, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ al Group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ - C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different Substituted phenoxy C ₁ having one or more substituents selected from a mono (halo C ₁ -C ₆ alkyl) amino group or a di (halo C ₁ -C ₆ alkyl) amino group which may be the same or different on the ring -C ₆ alkyl group, phenyl C ₁ -C ₆ alkyl group or the same or different, halogen atom, 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, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ al Killsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different di One or more substituents selected from a C ₁ -C ₆ alkylamino group, a mono (halo C ₁ -C ₆ alkyl) amino group, or a di (halo C ₁ -C ₆ alkyl) amino group which may be the same or different. a substituted phenyl C ₁ -C ₆ alkyl groups having on the ring.
p shows the integer of 0-4. q represents an integer of 0 to 2.
X may be the same or different, and is a halogen atom, cyano group, amino group, nitro group, C ₁ -C ₆
Alkyl group, halo C ₁ -C ₆ 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 ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, a halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group or the same or different and may di C ₁ -C ₆ alkylamino group.
m shows the integer of 0-4. X can be combined with adjacent carbon atoms on the phenyl ring to form a condensed ring, which may be the same or different, and is a halogen atom, a C ₁ -C ₆ alkyl group, a 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, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group Halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C _1- which may be the same or different C ₆ alkylamino group, mono (halo C ₁ -C ₆ alkyl) amino group, same or different di (halo C ₁ -C ₆ alkyl) amino group, phenyl group, same or different, halogen atom , C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ al Alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different, mono (halo C ₁ -C ₆ alkyl) amino group or the same or different A substituted phenyl group having one or more substituents selected from di (halo C ₁ -C ₆ alkyl) amino groups, a heterocyclic group, or the same or different, halogen atom, 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, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ Alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl Group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di-C ₁ -C ₆ alkylamino group which may be the same or different, mono (halo C ₁ -C ₆ alkyl) amino group Alternatively, it may have one or more substituents selected from a substituted heterocyclic group having one or more substituents selected from di (halo C ₁ -C ₆ alkyl) amino groups which may be the same or different.
Y may be the same or different, and may be a hydrogen atom, halogen atom, cyano group, amino group, nitro group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ 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, cyclo C ₃ -C ₆ alkyl group, halocyclo C ₃ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group , halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group,
Halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di-C ₁ -C ₆ alkylamino group which may be the same or different, tri-C ₁ -C ₆ alkylsilyl group which may be the same or different, phenyl group, which may be the same or different, halogen Atom, 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, halo C ₁ -C ₆ Alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group , the same or different and may di C ₁ -C ₆ alkylamino group, a mono (halo C ₁ -C ₆ alkyl ) Amino group or the same or different and may di (halo C ₁ -C ₆ alkyl) substituted phenyl group having one or more substituents selected from amino group, heterocyclic group or the same or different and may a halogen atom , 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, halo C ₁ -C ₆ alkylthio Group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, Selected from the same or different di-C ₁ -C ₆ alkylamino group, mono (halo C ₁ -C ₆ alkyl) amino group or the same or different di (halo C ₁ -C ₆ alkyl) amino group And a substituted heterocyclic group having one or more substituents. n shows the integer of 1-5. Y can form a condensed ring together with adjacent carbon atoms on the phenyl ring, and the condensed rings may be the same or different, and may be a halogen atom, a C ₁ -C ₆ alkyl group, a 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, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group Halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, the same or different di C _1- C ₆ alkylamino group, mono (halo C ₁ -C ₆ alkyl) amino group, same or different di (halo C ₁ -C ₆ alkyl) amino group, phenyl group, same or different, halogen atom , C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ al Alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di C ₁ -C ₆ alkylamino group which may be the same or different, mono (halo C ₁ -C ₆ alkyl) amino group or the same or different A substituted phenyl group having one or more substituents selected from di (halo C ₁ -C ₆ alkyl) amino groups, a heterocyclic group, or the same or different, halogen atom, 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, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ Alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl Group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di-C ₁ -C ₆ alkylamino group which may be the same or different, mono (halo C ₁ -C ₆ alkyl) amino group Alternatively, it may have one or more substituents selected from a substituted heterocyclic group having one or more substituents selected from di (halo C ₁ -C ₆ alkyl) amino groups which may be the same or different.
Z ¹ and Z ² may be the same or different and each represents C—Y (wherein Y is the same as described above) or a nitrogen atom.
However, R ¹ and R ² simultaneously represent a hydrogen atom, R ³ represents a methyl group, X represents an iodine atom, m represents 1, Yn represents 2-methyl-4- [1,2,2, 2-tetrafluoro-1- (trifluoromethyl) ethyl] group, when p is 1 and q is 0, A excludes methyl and ethyl groups. }
An optically active phthalamide derivative represented by the formula: R ¹ and R ² may be the same or different and each represents a hydrogen atom or a C ₁ -C ₆ alkyl group, R ³ represents a methyl group or an ethyl group, A represents a C ₁ -C ₆ alkyl group, C _3- C ₆ alkenyl group, C ₃ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkyl sulfinyl C ₁ —C ₆ alkyl group, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group or mono C ₁ -C ₆ alkylcarbamoyl group, p represents an integer of 1 to 4, and X may be the same or different A halogen atom, a nitro group, a halo C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkoxy group, m represents an integer of 0 to 2, Y may be the same or different, Cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ 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 ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group A halo C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group, a halo C ₁ -C ₆ alkylsulfonyl group, a mono (halo C ₁ -C ₆ alkyl) amino group or the same or different di (Halo C ₁ -C ₆ alkyl) amino group, and Y may form a condensed ring together with adjacent carbon atoms on the phenyl ring, and the condensed rings may be the same or different. Well, halogen atom, 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, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, halo C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ alkyl Sulfonyl group, halo C ₁ -C ₆ alkylsulfonyl group, mono C ₁ -C ₆ alkylamino group, di-C ₁ -C ₆ alkylamino group which may be the same or different, mono (halo C ₁ -C ₆ alkyl) amino It may have one or more substituents selected from a group or a di (halo C ₁ -C ₆ alkyl) amino group which may be the same or different, and n is 1
The optically active phthalamide derivative or a salt thereof according to claim 1, which shows an integer of -4. R ¹ and R ² may be the same or different and each represents a hydrogen atom or a C ₁ -C ₆ alkyl group, R ³ represents a methyl group, A represents a C ₁ -C ₆ alkyl group, C ₃ -C ₆ alkenyl Group, C ₃ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ an alkyl group or a C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkyl group, p is 1 to 4
Q represents 1 or 2, X may be the same or different, and represents a halogen atom, a nitro group, a halo C ₁ -C ₆ alkyl group or a halo C ₁ -C ₆ alkoxy group, and m is Represents an integer of 0 to 2, Y may be the same or different, and is a halogen atom, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ 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 ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group,
Halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkyl sulfinyl group, halo C ₁ -C ₆ alkyl sulfinyl group, C ₁ -C ₆ alkyl sulfonyl group or halo C ₁ -C ₆ alkyl sulfonyl group, , Y can be combined with adjacent carbon atoms on the phenyl ring to form a condensed ring, which may be the same or different and are a halogen atom, a C ₁ -C ₆ alkyl group, a 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, halo C ₁ -C ₆ alkylthio group, C ₁ -C ₆ alkylsulfinyl group, It may have one or more substituents selected from a halo C ₁ -C ₆ alkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group or a halo C ₁ -C ₆ alkylsulfonyl group, and n is an integer of 1 to 4 The optically active phthalamide derivative according to claim 1 or a salt thereof. (S) -3-iodo-N ^1- {2-methyl-4- [1,2,2,2-tetrafluoro-
1- (trifluoromethyl) ethyl] phenyl} -N ² - (1-methyl-2-methylsulfonyl-ethyl) phthalamide, (S)-3-chloro -N ¹ - {2-methyl-4- [1,2
, 2,2-Tetrafluoro-1- (trifluoromethyl) ethyl] phenyl} -N ^2- (
1-methyl-2-methylsulfonylethyl) phthalamide, (S) -3-bromo-N ^1-
{2-methyl-4- [1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] phenyl} -N ² - (1-methyl-2-methylsulfonyl-ethyl) phthalamide or (S) -3-iodo-N ^1- {2-methyl-4- [1,2,2,2-tetrafluoro-
1- (trifluoromethyl) ethyl] phenyl} -N ² - (1-methyl-2-methylsulfinyl-ethyl) optically active phthalamide derivative or a salt thereof is selected from phthalamide.   An insecticide for agricultural and horticultural use comprising the optically active phthalamide derivative according to any one of claims 1 to 4 or a salt thereof 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 5 on a target plant or soil in order to control pests from useful plants.