JPS60158173A - Alpha-methyl-(6-phenoxy)-2-picolylcyclopropane carboxylate, manufacture and composition - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to α-methyl-(6-phenoxy)-2-picolylcyclopropane carboxylates, processes for the preparation of these esters and their use in the control of pests.

α-Methyl-(6-7enoxy)-2-picolylcyclopropanecarboxylate) 1d Formula I:X.

(In the formula, Xt represents a methyl group or a halogen atom, R represents a hydrogen atom or a halogen atom, and the island represents a hydrogen atom, a halogen atom, or a carbon atom having 1 to 4 carbon atoms.
an alkyl group, an alkoxy group having 1 to 4 carbon atoms,
C 1 -C 4 alkylthio group, C 1
haloalkyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, haloalkylthio group having 1 to 4 carbon atoms, alkenyl group having 2 to 4 carbon atoms, alkynyl group having 2 to 4 carbon atoms, nitro group Or represents a cyan group. ).

The halogen atom in the above definition represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

Alkyl, alkoxy, alkylthio, haloalkyl,
Haloalkoxy, haloalkyl, argenyl and alkynyl groups may be straight chain or branched. Examples of such groups are, for example, methyl, methoxy, methylthio, trifluoromethoxytrifluoromethoxy, ethyl, ethoxy, propyl, inobu-avir, n-butyl,
These are vinyl, 1-7'robenyl, ethynyl, and 1-propynyl groups.

% preferred compounds of formula I are those in which Xl represents a methyl group or a chlorine atom, R1 represents a hydrogen atom or a halogen atom, and R2 represents a hydrogen atom, a halogen atom, a carbon atom number of 1 to 4
an alkyl group, an alkoxy group having 1 to 4 carbon atoms,
It is a compound representing an alkylthio group, a vinyl group or an ethynyl group having 1 to 4 carbon atoms.

The most preferable compound represented by formula (1) is one in which Xl represents a methyl group or a chlorine atom, R1 represents a hydrogen atom,
and a compound in which R2 represents a hydrogen atom or a halogen atom.

Compounds of formula 1 are produced, for example, by the following methods known per se: 1) LVKhr, Rt r Rt & HXs
Fi represents the meaning defined for expression l.

In formulas ■ and ■, one of X and X' represents a hydroxyl group and the other represents a halogen atom, preferably a chlorine atom or a bromine atom; alternatively, both X and X' represent a hydroxyl group and In (2), R represents an alkyl group having 1 to 4 carbon atoms, preferably a methyl or ethyl group. Suitable acid acceptors are especially tertiary amines,
For example trialkylamines and pyridines, and also hydroxides, oxides of alkali metals and alkaline earth metals,
Carbonates and bicarbonates, and also alkali metal alcoholides, such as potassium tert-butyrate and sodium methylate. As hydrophilic drug it is also possible to use, for example, dicyclohexylcarbodiimide.

Methods 1 and 2 are from -10° to 120°C, usually 20°
The reaction is carried out at a reaction temperature of from 80 DEG C. to 80 DEG C. under normal or elevated pressure and preferably in an inert solvent or diluent. Examples of suitable solvents or diluents are, for example, ethers and ethereal compounds such as diethyl ether, dipropyl ether, dioxane, dimethoxyethane, and tetrahydroamides, such as [N,N-dialkylated carboxamides; aliphatic, aromatic and halogenated hydrocarbons,
In particular benzene, toluene, xylene, chloroform and hydrochlorobenzene: nitriles such as acetonitrile; dimethylsulfoxide di- and keto/such as acetone and methyl ethyl ketone.

The starting materials represented by 21 to 2 are known or can be prepared by methods analogous to known methods.

The compound of formula (1) can be obtained in the form of a mixture of different optically active isomers when a heterogeneous optically active starting material is used in the reaction. The different isomeric mixtures can be resolved into the individual isomers by known methods. It is to be understood that the compounds of formula I include the individual isomers as well as mixtures thereof.

The compounds of formula I are suitable for controlling various animal and plant pests. Therefore, compounds of formula I may be used in insects, such as Lepidoptera (Lepidoptera).
tera), Coleoptera, Homoptera, Heteptera
roptera), Polyptera (Diptera), Thripsiptera (Tbysanoptera), Orthoptera (
0rthhoptera)
ra), 8iphonaptera, Mal Iophaga, Th.
ysanura), termites (1soptera
), Psocoptera and Lymenoptera, as well as Nyattaniformes, %-V and Cheetos.

Compounds of the formula I are particularly suitable for plant-destructive insects, especially plant-destructive feeding insects, such as Subodoplate littoralis (5
podoptera Littora-1is), Jeli-othis
virescens), black leafhopper (Nep
ho-otettix cincticeps), Tobiiro/power (Ni1apa-ravata Iuge)
ns), Chilo 5uppress
a-1is) and the brown-bottomed planthopper (1, aodelp
hax 5triate-11us)) and insects that attach to vegetables and fruits [e.g.
1neata), green peach aphid (Myzus
persicae), Lasbeylesia pomonella (La
5peyresia pomone order a) and Adoxophyes reticulana (Adoxophyes reticulana).
ticulana)) as well as soil insects [e.g.
('hortophila brassicae)
, Diaprotica balteata (1) iabrotic
a balte-ata), Bakunoda Sabigni (
Pachnoda savign-yi) and Scotia ypsi-1
on)).

The compounds of formula I are also useful against insecticides such as house flies and mosquito larvae and against insects such as Makabei family (1xo
It is highly effective against ectoparasitic mites and ticks of the families Argasidae, Argasidae and Dermanyssidae. Furthermore, the compounds of formula I have extensive ovicidal and larvicidal activity.

Compounds of formula I are suitable for use in the larvae of the v4 sacral order, such as Tineola sp. and Tinea sp.
5 pec, ) and Attagenus sp.
It has a proven activity against insects that grow on keratin, such as 5pec, ).

The compounds of formula I are used to protect keratinous materials against insect damage, in particular from insects, especially moths and beetles, and to promote such materials with a washable and light-resistant protective finish. most suitable for The gelatinous material to be protected can be in both raw or processed form, for example products made from raw or processed sheep's wool or other animal hair, hides, furs and feathers. A particularly important feature is the webbing moth (Webbing c.
lothes moth; Tineola biss
elliela ) and common clot
lies moth ; Tinea pelione
lla) and against the larvae of the fur beetle (
fur beetle; Attagenus 5
pec, ) and Kave-Sotobi-) A/ (
('arpet beetle; Anthren
Figure 2: Efficacy of a compound of formula I against larvae of the US 5 pec. The compounds of formula I are therefore suitable for use on the one hand in woolen fabrics, such as blankets, woolen rugs, woolen underwear, woolen clothing, fabrics and wool-containing fabrics, e.g. mixtures in which one component is wool, e.g. It is preferred for protecting mixtures of wool with other natural fibers, preferably cotton, and on the other hand for protecting wool and animal hides from attack by the abovementioned pests.

The acaricidal and/or insecticidal action can be substantially extended by adding further insecticides and/or acaricides. Examples of suitable additives are: organic υ
compounds, nitrophenol and its conductors, formamidine, urea, other pyrethroids, carbamates and chlorinated hydrocarbons.

The compounds of the formula (II) are also used particularly advantageously in combination with substances which confer a synergistic or protective effect on the pyrethroids. Examples of such compounds include piperonyl butoxide, propynyl ether, propynyl oxime, propynyl carbamate and propynyl phosphonate, 2-
(3,4-'fshi/dioxyphenoquine)-3°6.9
-) Rioxaundeca/[Sesamenochus (Sesame
x) or 5esoxane)8
．． 8.8-) Butyl phosphorotrithioate, 1.2
-methylenedioxy-4-(2-(octylsulfinyl)furobyl)benzene.

The compounds of the formula ■ are used in neat form or preferably with the auxiliaries customary in backside technology and are therefore prepared in known manner, for example as concentrates, directly sprayable or dilutable solutions, diluted emulsions. , aqueous powders, soluble powders, powders or granules, and also capsules, for example in polymeric materials. The method of application, for example spraying, atomizing, dusting, spraying or dipping, is selected depending on the intended purpose and the given environment, as well as the nature of the composition.

Preparations, ie, compositions and preparations containing the compound of formula (1) (active ingredient) and optionally solid or liquid auxiliary agents, can be prepared in a known manner, for example by adding the barbed ingredient to a solvent, e.g.
It is prepared by homogeneous mixing and/or milling with fillers such as solid carriers and optionally surface-active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably C8-C12 fractions such as xylene mixtures or substituted natutale; phthalate esters such as dibutyl or dioctyl phthalate; cyclohexane or paraphthalate/
Aliphatic hydrocarbons such as: ethanol, alcohols and glycols such as ethylene glycol monomethyl or monoethyl ether, and their ethers and esters: keto/such as cyclohexanone; hemethyl-2-pyrrolidone, dimethyl sulfoxide or dimethyl formamide and epoxidized vegetable oils such as epoxidized nut oil or soybean oil; or water.

Solid carriers used for example in dusts and dispersible powders are generally natural mineral fillers such as calcite, talc, kaolin, montmorillonite or attapulgite. It is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers to improve the physical properties. Suitable granular adsorbent carriers are of the porous type, for example pumice, crushed brick, ceviolite); and suitable non-absorbent carriers are materials such as calcite or sand. Furthermore, a large number of pre-granulated inorganic or organic materials can also be used, such as in particular dolomite or pulverized plant residues.

Suitable surface-active compounds, depending on the nature of the compound of formula I to be incorporated, are nonionic, cationic and/or anionic surfactants which have good emulsifying, dispersing and It has wettability. "Surfactant" also means a mixture of surfactants.

Suitable anionic surfactants are both water-soluble soapstones/and water-soluble synthetic surface-active compounds.

Suitable soaps are alkali gold salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (10 to 22 carbon atoms), such as oleic acid or stearic acid, or natural fatty acid mixtures obtained, for example, from coconut oil or tallow) or potassium salts. Fatty acid methyltaurate salts are also another suitable surfactant.

However, more frequently so-called synthetic surfactants are used, in particular fatty sulfo/acid acids, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates.

Fat sulfonates or sulfates are usually alkali metal salts,
in the form of alkaline earth metal salts or unsubstituted or substituted ammonium salts and containing an alkyl group having 8 to 22 carbon atoms, where °
"Alkyl" also includes the alkyl part of the acyl group, for example the sodium or calcium salts of lignin sulfonic acid, dodecyl sulfate or fatty alcohol sulfate mixtures prepared from natural fatty acids. Also included are sulfuric acid esters and salts of sulfo/acids. Sulfo/penozimitazole derivatives preferably contain two sulfonic acid groups and a fatty acid group having from 8 to 22 carbon atoms. Examples of /acid acids are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or naphthalenesulfonic acid/formaldehyde condensation products. The corresponding phosphates, e.g. tJfp
Salts of υnoic acid esters of adducts of -nonylphenol with 4 to 14 mol of ethylene oxide are also suitable.

Nonionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which contain from 3 to 50 glycol ether groups and (aliphatic) hydrocarbons. 8 to 20 carbon atoms in the group and 6 to 18 carbon atoms in the alkyl portion of the alkylphenol.

Other suitable nonionic surfactants are water-soluble adducts of polyethylene oxide with polypropylene/glycols, ethylene dianepropylene glycol and alkylboriglopylene glycols having 1 to 10 carbon atoms in the hyalkyl chain. , their adducts are 20 to 2
Contains 50 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. The above compounds usually contain from 1 to 5 ethylene 7 glycol units per probilene/glycol unit.

Typical examples of nonionic surfactants are nonylphenol-polyethoxyethanol, castor oil polyglycol ether, polypropylene/polyoxyethylene adduct,
These are tributyl phenoxy polyethoxy ethanol, polyethylene glycol and hyoctyl phenoxy ethoxy ethanol. Fatty acid esters of polyoxyethele 7 norvitan/ and polyoxyethele 7 sorbitan trioleate are also suitable nonionic surfactants.

The cationic surfactant preferably has 8 as an N-substituent.
is a quaternary ammonium salt containing at least one alkyl group having from 22 to 22 carbon atoms and, as another substituent, an unsubstituted or halogenated lower alkyl group, be/zyl group or lower hydroxyalkyl group. . The salt is preferably in the form of a chloride, methyl sulfate or ethyl sulfate, such as stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium habromide.

Surfactants commonly used in the pharmaceutical industry are described, for example, in the following publications: 1 McCutcheon's Detergents and Emulsifiers Annual
's Detergents and Bmulsi
fiersAnnual)'', MC Publishers, Ring-wood, New Chassis, 1979; and 'l''ensid-T by H.
a5chenbuch)', Karl Hanser Publishing,
Munich/Bina, 1981.

Pest control agents usually contain (11 to 99%, preferably (11 to 95%) of a compound of formula I as a solid or liquid adjuvant, and 1 to 25 qb, preferably al to 20%. Contains surfactants.

Although commercial products are preferably in the form of concentrated compositions, consumers typically use dilute formulations.

The composition may also contain other ingredients such as stabilizers, defoamers, viscosity regulators, binders, tackifiers and fertilizers or other active ingredients for special effects. Good too.

Example of formulation of liquid active ingredient represented by formula I (% is weight %) 1. Emulsion stock solution a) b) c formula! Compound represented by 25% 40% 50% Calcium dodecylbenzenesulfonate 5% 8% 6% Cyclohexanone -15% 20% xylene mixture 65CI) 25% 20qb By diluting the emulsion stock solution with water, emulsion/concentration of desired concentration can be obtained. can be manufactured.

2. Solution a) b) c) d) Compound represented by formula ■ 80% 10% 5% 95
% Epoxidized Coconut Oil --1% 5% These solutions are suitable for application in microdroplet form.

5 tablets a) b) Compound represented by formula I 5% 10% kaolin 94
% - Highly dispersed silicic acid 1 Easy - Attapulgite - 90% The active ingredient is dissolved in methylene chloride and this solution is used as a carrier.
Fog followed by removal of the solvent under reduced pressure.

4. Powder a) b) Compound represented by formula 2 5% Highly dispersed silicic acid 1% 5% Merck No. 97 - Kaolin - 90% Can be used as is by uniformly mixing the active ingredient and carrier. A powder can be obtained.

Example of blending solid active ingredients represented by formula I (% is weight i%) 5. Irrigation agent a) b) c) Compound represented by formula 1 25'l 50qb 75%
Sodium lignosulfonate/acid 5% 5% - Sodium lauryl sulfate 3%-5% Highly dispersed silicic acid 5% 10% 10% Kaolin 62% 27% - After thoroughly mixing the active ingredients with the auxiliaries, the mixture is Grind well with a mill. An irrigation agent is obtained which can be diluted with water to obtain a suspension of the desired concentration.

6. Emulsion stock solution Compound represented by formula I 10 Easy cyclohexanone 30% Xylene mixture 50% By diluting this emulsion stock solution with water, an emulsion with a desired concentration can be obtained.

Powder a) b) Compound of formula I 5% 8% Talc 954b - Kaoli/-92% For use as is by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. A powder that can be obtained is obtained.

a Compound represented by the extruded granule formula (■) 10% Lychnosulfo/sodium acid 2 carboxymethylcellulose 1 Chikaori 7 87% The active ingredient is mixed and ground together with the auxiliary agent, and the mixture is subsequently moistened with water. The mixture is extruded and dried in a stream of air.

9 Coated granules Compound represented by formula I 6% Polyethylene glycol (molecule 1lt200) 556
Kaori 7 9t% The finely ground active ingredient is applied uniformly to the polyethylene glycol-moistened kaolin in a mixer.

By this method, a non-dusting suspension agent suspension compound of formula I 40 qb ethylene glycol 10% sodium lignosulfonate 10% carboxymethyl cellulose 1 37% formaldehyde aqueous solution 02% water 32% finely ground active ingredients Mix uniformly with auxiliary agents,
A suspendable concentrate is obtained which can be diluted with water to obtain a suspension of the desired concentration.

Example 1: Production of a compound represented by the following formula: A solution of 4.3 g of pyridine and 9 g of the compound FL represented by the following formula in 55 ml of toluene was dissolved at 0°C in 60 d of toluene represented by the following formula: Add 6.7 g of the compound in portions continuously to the solution. The reaction mixture is stirred for 30 hours at 25°C, then poured into 2N hydrochloric acid and extracted with ether. The ether layer is washed with a saturated solution of IJ (bicarbonate) and IJ (chloride), dried over magnesium sulfate, and concentrated. The product was developed through silica gel with toluene/ethyl acetate (95:5) and
Perform chromatography at 63°C to '64°C.
The title compound (1) is obtained as a mixture of diastereoisomers having a melting point of .

By analogous methods, the following compounds can also be prepared: X.

Uli3 L,'k13 Example 2: Insecticidal-toxic effect of NilaNllapa 7
rvatalu) Rice plants are sprayed with a solution containing 50 ppm or 10 ppm of the test compound. After the spray coating has dried, the plants are infected with brown planthopper nymphs at the N3 stage. Two plants are used for each test compound and for each test species.

Mortality assessment will be made after 6 days. The test is carried out at 22° C. and 60% relative humidity. In this test,
The compound of Example 1 is 100% effective against brown planthopper nymphs at a concentration of 50 ppm.

Example 3: Diabrotica balteata (Diabroticaba)
lteata) K vs. sull action sandy soil 750- of the test compound 3, 0.75.

Mix with 150 liters of solution containing 0.2 or 0.05 ppm. Corn seedlings are planted in plastic pots filled with treated soil (4 seedlings per 10 cm diameter pot). Immediately after that, shift the pot.
f 7 ta (1) iabrotica balteat
a) Infect 10 larvae at seed stage 3. Evaluation is carried out 10 days after infection with larvae.

The compound of Example 1 was administered at a concentration of 3 ppm to 1% against L3 stage larvae of Diabrochia parteata in the above test.
00% effective.

Example 4: Effect on tics A) Amblyommab
ebraeum) in a test tube, count 50 nymphs, 10.1 or 0.
Immerse for 1 to 2 minutes in an aqueous emulsion 21 prepared from a dilution series containing 1 ppm of test compound. The test tube is then sealed with a standard raw silk diameter and inverted so that its main line can absorb the emulsion. Evaluation will be done one week later. Repeat each test twice.

B) Porphyrus microbulus ((Boophilus)
smicroplus), larvae] Using a dilution series similar to test A), the test was carried out on 20 UP-susceptible larvae and 20 JP-resistant larvae (resistance relates to tolerance to Cyazino/). The compound of Example 1 was added to Chicknia/Ambyloma h. at a concentration of 1 ppm.
ebraeum) and Beauphilus micropulus (
100% effective against nymphs and larvae of Boophilus m1croplus).

Example 5: Insecticidal gastrotoxic effect: Subodophtera littoralis (8 pods)
optera 1lttoralis) cotton plants are sprayed with a solution containing 100, 200 or 400 ppm of the test compound. After the spray coating has dried, the plants are treated with L1 stage Spodoptera littoralis (8p
The infection is caused by the larvae of odoptera itoralis. Two plants are used for each test compound and for each test species. Mortality rate evaluation 2.4.24 and 48
Do it after hours. The test is carried out at 28° C. and 60% relative humidity. In this test, the compound of Example 1 was
It is 100% effective against Subodoptera littoralis larvae at a concentration of 0.00 ppm.

Example 6: Webbing cloths moth
), fur beetle and l! J-he-/to beat/l/ (carp
a) Depletion method A 0.4% basic solution is prepared by dissolving each of the compounds of Example 1 in methyl seron lube. Next, distilled water 120WL
An aqueous treatment bath is prepared at room temperature containing 5 andozin KB (112 m/1), formic acid 1:10 [L6WLl] and 0.75 rnlf of each 0.4qb base solution. First, 6 g of wool flannel is moistened with warm water and placed in a bath at room temperature.

While constantly stirring the wool sample, the temperature of the bath was increased to 20°C.
The temperature was raised to 60°C over a few minutes, and the temperature was then treated at 60°C for 30 minutes. The bath was then cooled and the wool samples soaked in distilled water for 3 minutes.
Washed twice, hand wrung, and air dried. The concentration of active ingredients is 1000% by weight of wool.
It is ppm. Moth-resistance test [
Koiga (webbing C1othes moth)
; Tineolabiselliella Hum
) and Furby)
/l/ (fur beetle; Attage-
nus pieus) and the carpet beetle (c
arpetbeetle; A11jllrenUS
A resistance test against larvae of VOraX waterhouse is conducted.

Sample pieces of the same size were cut from the treated wool samples and subjected to attack by 15 larvae of each pest for 14 hours at constant temperature (28°C) and constant relative humidity (65%). Expose.

The evaluation is, on the one hand, by the relative weight loss of the test specimen;
On the other hand, it depends on the number of organisms still living.

The test compound of Example 1 showed 1% against all three pests.
00% effective.

b) Budd Method A 0,4 qb base solution is prepared by dissolving each of the compounds of Example 1 in methyl selon. Each basic solution (
12,5d) wosu/Dojin (5andozin)K
B■ (5 with methylselonorsib containing 165g/l)
Dilute to 0 m (solution 1). Solution 1 (25d) -)J
-y Tor7 (8andozin) KB(!!'
0.5 F/l! Methylseron lube containing 50
- (Solution 2), then solution 2 (25@l) in order of santol y (8andozin) KB [15
Dilute to 50 gJ with methylceronelube containing y/l (solution 3).

Solutions 1.3- of each of 2 and 3 are placed in a crystallization dish and a disc of wool flannel is immersed therein for 6 seconds. The wet disks are then packed between aluminum sheets so that they are 50% impregnated with each solution. The concentration of the effective fraction was 50% for the disks treated with solutions 1.2 and 3, respectively.
0 ppm, 250 ppm and 1251) pm. The wet disk was then dried in air and Example 6
Perform the same biological tests as described in a.

The test compound of Example 1 was effective against all three types of pests.
100% even at the lowest concentration of 125 ppm
There is an effect.

Claims (1)

[Claims] (1) The following formula I: X'. (In the formula, Xl represents a methyl group or a halogen atom, R1 represents a hydrogen atom or a halogen atom, and R2a a hydrogen atom, a halogen atom, a carbon atom number of 1 to 4
an alkyl group, an alkoxy group having 1 to 4 carbon atoms,
C 1 -C 4 alkylthio group, C 1
haloalkyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, haloalkylthio group having 1 to 4 carbon atoms, alkenyl group having 2 to 4 carbon atoms, alkynyl group having 2 to 4 carbon atoms, nitro group Or represents a cyano group. )-Methyl-(6-phenoxy)-2-picolylcyclopropanecarboxylate. (2) In the above formula (2), Xl represents a methyl group i or a chlorine atom, R1 represents a hydrogen atom or a halogen atom, and R: is a hydrogen atom, a halogen atom, or has 1 to 4 carbon atoms.
The compound according to claim 1, which represents an alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a vinyl group or an ethynyl group. (3) The compound according to claim 2, wherein in the formula I, Xl represents a methyl group or a chlorine atom, R represents a hydrogen atom, and R2 represents a hydrogen atom or/and a rogene atom. (4) The compound according to claim 5, which is represented by the following formula: (5) A compound according to claim @3, represented by the following formula: (6) The compound according to claim 3, which is represented by the following formula: (7) The compound according to claim 6, represented by the following formula: (8
) The compound according to claim 3, represented by the following formula 2e/. (9) The compound according to claim 6, which is represented by the following formula: Qd The compound according to claim 6, which is represented by the following formula: (b) The compound according to claim 6, which is represented by the following formula: (2) The compound according to claim 3, which is represented by the following formula: (To) The compound according to claim 2, which is represented by the following formula: a4 The compound according to claim 2, which is represented by the following formula: On The compound according to claim 2, which is represented by the following formula: αQ The compound according to claim 2, which is represented by the following formula: % formula %: 13. The compound according to claim 2, which is represented by the following formula: αη. (To) The compound according to claim 2, which is represented by the following formula: Ql The compound according to claim 2, which is represented by the following formula: By reacting a compound represented by the following formula: with a compound represented by the following formula: in the presence of an acid acceptor, the following formula I: (In each of the above formulas, Xl represents a methyl group or a halogen atom. where R1 represents a hydrogen atom or a halogen atom, the island represents a hydrogen atom,
・Rogge/atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, alkylthio group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, 1 to 4 carbon atoms 4-7-roalkoxy group, /-roalkylthio group having 1 to 4 carbon atoms, alkenyl group having 2 to 4 carbon atoms, alkynyl group having 2 to 4 carbon atoms, nitro group or ni-ano group, One of X and X' represents a hydroxyl group, and the other represents a halogen atom. ) A method for producing a compound represented by (b) As an active ingredient, the following formula I: X. (In the formula, Xl represents a methyl group or a halogen atom, R1 represents a hydrogen atom or a halogen atom, and R2 represents a hydrogen atom, a halogen atom, or a carbon atom having 1 to 4
an alkyl group, an alkoxy group having 1 to 4 carbon atoms,
C 1 -C 4 alkylthio group, C 1
haloalkyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, haloalkylthio group having 1 to 4 carbon atoms, alkenyl group having 2 to 4 carbon atoms, alkynyl group having 2 to 4 carbon atoms, nitro group Further, 1 represents a cyano group. ), together with adjuvants commonly used in formulation technology, for pest control compositions. 22. The composition according to claim 21, containing the compound represented by formula I, for controlling various pests of animals and plants as well as soil pests. 23. The composition according to claim 22, wherein the harmful organisms to be controlled are representative of insects and acarina. ■ A patent containing an effective amount for controlling pests of a compound represented by formula I, for application to animals, plants, and soil for controlling animal and plant pests and soil pests. A composition according to claim 26.