JPS5844649B2 - Ether Yudo Tai no Seihou - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing ether derivatives, specifically 4-alkoxy- or 4-alkoxymethyldiphenyl ether derivatives or l-cyclohexyloxy substituted or unsubstituted phenyl nuclei. This invention relates to a method for producing a 4-alkoxymethylbenzene derivative.

The derivatives influence the development of insects and mites.

Said derivative corresponds to the following general formula: [wherein R1 represents hydrogen, halogen, an alkyl group having 1 to 4 carbon atoms, a vinyl group or an ethynyl group, and R
2 represents hydrogen, halogen, methyl group, or ethyl group, or R1 and R2 together form a cyclopentyl ring or cyclohexyl ring, and R3 represents hydrogen, halogen, methyl group, ethyl group, or 1 to 4 represents an alkoxy group having a carbon atom, R4 represents hydrogen, halogen or a methyl group, R6 represents hydrogen or halogen, or R
3 and R3 together represent a carbon-carbon bond or an oxygen bridge, R6 represents hydrogen, a methyl group or an ethyl group,
R7 represents a cyclohexyl group or a group to an alkyl group having 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms)! and Y represents oxygen or a group -CH-0- (in the formula, Z represents hydrogen or a methyl group), in which -CH-
group is bonded to the phenyl nucleus, m and n are each O
or represents the numerical value of 1.”

Halogen stands for fluorine, chlorine, bromine or iodine, especially chlorine.

The alkyl and alkoxy groups attached to R, R3 and R7 may be straight or branched.

Examples of radicals of this kind are, inter alia, methyl, ethyl, n-propyl, isopropyl, -1m-1sec-butyl, methoxy, ethoxy.

In general formula (1), R1 is hydrogen, chlorine, methyl, ethyl, n-propyl, isopropyl, n-1isec
- represents butyl, vinyl or ethynyl, R2 is hydrogen,
represents chlorine or methyl, or R1 and R2 together form a cyclopentyl ring or a cyclohexyl ring,
R3 represents hydrogen, methinok, ethyl, methoxy or ethoxy, R4 represents hydrogen, chlorine or methyl, R5
represents hydrogen, or R3 and R5 together represent a carbon-carbon bond or an oxygen bridge, R6 represents hydrogen or methyl, and R7 represents cyclohexyl or a group; ≧8 (wherein R8 is hydrogen, (represents chlorine, methyl, ethyl or ethoxy), Y represents oxygen or a group -CH-0- (wherein Z represents hydrogen or methyl) Z, in which the - and H- groups form a phenyl nucleus. Compounds in which m and n each represent a numerical value of O or 1 are excellent.

In general formula (1), R1 is hydrogen, chlorine, methyl, ethyl, n-propyl, isopropyl, n-1isec
-represents methyl, vinyl or ethynyl, R2 is hydrogen,
represents chlorine or methyl, R3 represents hydrogen, methyl, ethyl, methoxy or ethoxy, R4 represents hydrogen, chlorine or methyl, R6 represents hydrogen, or R3 and R3 together form a carbon-carbon bond or represents an oxygen bridge, R6 represents hydrogen or R7 represents a group OR8 (in the formula, R8 represents hydrogen, chlorine, methyl, ethyl or ethoxy), Y represents oxygen or a group -CH20-,
Compounds in which the CH2- group of the group is bonded to the phenyl nucleus, and m and n each represent a numerical value of O or 1, are particularly excellent in terms of their action.

The compound of general formula (I) is produced in a conventional manner by the following method.

1) Generating an ether by condensing a halide of general formula (Jll) with a compound of general formula (N) (
(O-alkylation) Rice methyl is distilled, and the general formulas (I) and (l [D, in which R1-R7
, Ylm and n are as defined above, and X represents chlorine, bromine or iodine, especially chlorine or bromine.

M represents a metal, particularly a metal of Group I or II of the periodic table, or hydrogen.

Among the compounds of general formula (1) thus obtained, those belonging to general formula (IB) are epoxidized to form compounds of general formula (I).
C) can be used as an epoxy compound.

In general formulas (IB) and (IC), R1, R2, R
4r R6r R7r Y r m and n are general formula (I
).

Hydrogen halide can also be added to the olefinic double bond of the compound of general formula (IB).

In the general formulas (IB), (IDa) and (IDb), R,, R2+R4, R6, R7rY 1m and n represent those described for the general formula (1), and X represents halogen, particularly chlorine.

To produce an epoxy compound of formula (IC), an unsaturated halide may be epoxidized to give an epoxy halide, which may be condensed with a compound of general formula (n): ), (in m and (v), R1, R2, R4J R6, R7h Y 1m , n
and M represent the above.

X represents halogen, especially bromine or chlorine.

The compound of general formula (IB) is hydrogenated to form general formula (IE)
It can also be a compound of: R1, R2, R4p R6, R7, Y in the above general formula.

m and n represent those described for general formula (I) above.

A compound of general formula (IF) having a conjugated triple bond can also be selectively hydrogenated to form a compound of general formula (IG) having a conjugated double bond.

In the general formula, R2r R4r R6r R7p Y p
m and n represent those described for general formula (I).

Alcohol or water can also be added to the double bond of the compound of general formula (IB): In the above general formula, R,, R2, R4, R6, R7, Y.

m and n represent those described for general formula (1), A represents an anion of a mercuric salt, and Rζ represents an alkyl group having 1 to 4 carbon atoms or hydrogen.

Rice It is advantageous to use mercuric acetate or mercury fluoroacetate as the mercuric salt.

It is also possible to alkylate alcohols of the general formula (IJ) corresponding to the case where the compound R'3 of the formula (IH) is hydrogen: in the above general formula R,, R2, R,, R6, R,, Y.

m and n represent the same as described for general formula (1), X represents a halogen atom, and R) represents an alkyl group having 1 to 4 carbon atoms.

Alkylation of 4-hydroxydiphenyl ether or 4-cyclohexyloxyphenol or their nuclear substituted derivatives can be carried out using various saturated or unsaturated halogenides in various solvents depending on the reactivity of the halogenide used. It can be carried out at the reaction temperature and always in the presence of at least 1 mol of base.

Solvents include, in particular, acetone, methyl ethyl ketone, cyclohexanone, 2-dimethoxyethane, tetrahydrofuran, dioxane, dialkyl ether, dimethyl formamide, dimethyl sulfoxide, hexamethyl phosphoric triamide, sulfolane, inert hydrocarbons such as toluene, benzene, xylene, etc. is appropriate.

However, other solvents can also be used.

The base or acid acceptor required when forming an ether from the compound of general formula (II) and a halide is:
In particular, alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal carbon salts, alkali metal or alkaline earth metal hydrides and alkali metal alkoxides are used.

However, it is also possible to use organic bases such as triethylamine, pyridine, etc. as acid acceptors.

The reaction temperature for forming the arylalkyl ether is -10-130°C, often 5-70°C (e.g. dimethylsulfoxide, dimethylformamide, dioxane, sulfolane, tetrahydrofuran, hexamethylphosphoric triamide, 1,2-dimethoxyethane, etc.). or the boiling point of the solvent used (for example, in the case of ketones).

The conversion of compounds of general formula (IB) into the corresponding epoxy derivatives is carried out using an epoxidizing agent in an inert solvent, in particular a chlorinated hydrocarbon, at a temperature between 5°C and room temperature, often between -5°C and +5°C. , for example with peracids.

The epoxy derivative of the general formula (ic) has the general formula (IB) (
7) The fulkenyl ether is homogenized using an N-halogen succinimide, e.g.
The corresponding halogenhydrin is converted into bromohydrin in phase or in a heterogeneous phase at a temperature of 1°C to room temperature, and then this bromohydrin is treated with an alkaline reagent, such as an alkali metal carbonate or an alkali metal alkoxide, to give the desired epoxide. It is obtained by eliminating hydrogen halide.

Alkali are in particular sodium and potassium.

The term "peracid" primarily refers to lower peralkanoic acids having 1 to 6 carbon atoms, such as peracetic acid, as well as aromatic peracids,
For example, perbenzoic acid, monoperphthalic acid, especially 3-chloroperbenzoic acid.

Post-treatment and isolation of the compound of general formula (1) can be carried out by known methods,
This is carried out, for example, by adding water or ice to the reaction mixture, followed by extraction with a suitable solvent, for example ether, washing the organic phase, for example with dilute lye or alkali carbonate, and drying the solution over anhydrous sodium sulfate.

After removing the solvent, the remaining compound of general formula (1) can be purified, if necessary, by crystallization, vacuum distillation or chromatography on silica gel or/or aluminum oxide.

To obtain the compound of general formula (IC) to be epoxidized,
Various reaction orders are possible.

That is, according to the above production method, the hydroxyl group of the 4-hydroxy-diphenyl ether compound or 4-cyclohexyloxyphenol compound is first etherified with an alkenyl halide in the presence of a base, and then the olefinic double bond in the aryl alkenyl ether is etherified. to an epoxy as described above, or by first epoxidizing the alkenyl halide in a chlorinated hydrocarbon with exclusion of moisture with an epoxidizing agent, e.g. was then reacted with 4-hydroxydiphenyl ether or 4-cyclohexyloxy-phenol in the presence of an acid acceptor to give the final product, epoxidized diphenyl oxide-alkyl ether or 4-cyclohexyloxyphenyl-alkyl ether.

For the addition of hydrogen halides, especially hydrogen chloride or hydrogen bromide, to aliphatic double bonds, the 4-alkenyloxy-diphenyl ether or 4-alkenyloxy-1-cyclohexyloxybenzene derivative is treated with a suitable solvent, e.g. chlorine. It is advantageous to work the anhydrous hydrogen halide in hydrogenated hydrocarbons, methanol, ethanol, other alcohols, dialkyl ethers, glacial acetic acid and the like.

The addition of hydrogen halide is carried out at a temperature of -30 DEG to +25 DEG C.

The resulting halide can be isolated by known methods, for example by adding water to the reaction mixture, extracting with an organic solvent, and removing excess hydrogen halide by neutralizing it with a weak base or washing with water. The halogenide remaining after removal of the solvent can be purified by crystallization, high vacuum distillation or chromatography.

The unsaturated aromatic aliphatic ether of general formula (IB) is prepared by a conventional method,
For example, using hydrogen excited with a catalyst, preferably room temperature to
Hydrogenation can be carried out at the boiling point of the reaction mixture under normal pressure or elevated pressure to give the saturated aromatic aliphatic ether of general formula (IF).

Particularly suitable catalysts are Raney nickel or noble metals, such as platinum or palladium.

As solvents, in particular acetic acid methyl and ethyl esters, dioxane or alcohols such as methanol,
This includes ethanol, etc.

The unsaturated aromatic aliphatic ether of the general formula (IF) is prepared by a conventional method,
For example, using hydrogen excited with a catalyst, hydrogen 1
It can be selectively partially hydrogenated until moles are absorbed to give ethers of general formula (IG).

Preference is given to using Lindlar catalysts as catalysts.

Suitable solvents are, for example, acetic acid methyl and ethyl esters, dimethoxyethane, dioxane or alcohols, such as methanol or ethanol.

The reaction to obtain the compound of general formula (1) in which R3 represents an alkoxy group having 1 to 4 carbon atoms is carried out in anhydrous alcohol R', OH at normal pressure, optionally in a solvent inert to the reaction components and In the diluent, for example ethers such as tetrahydrofuran, dioxane, diethyl ether,
It is carried out in 2-dimethyloxyethane or the like.

When R'3 is hydrogen, water can also be used as a solvent in the first step as well as in the second step.

As mercuric salts, preference is given to using mercuric acetate and mercuric trifluoroacetate.

As the complex hydride, for example, MeBH4 (wherein Me represents an alkali metal or alkaline earth metal atom) is used.

The reaction with the complex hydride is carried out in the presence of an alkali hydroxide and water.

The reaction temperature ranges from -10°C to +40°C, and from O to +25°C.
is within the range of

As an alternative method of obtaining compounds of general formula (1) in which R3 represents an alkoxy group having 1 to 4 carbon atoms, an alcohol of general formula (IJ) can be reacted with a halide depending on the reactivity of the halide used. The etherification can also be carried out by reacting in different solvents at different reaction temperatures, always in the presence of at least 1 mol of said base.

The compounds obtained should, in principle, be cis-
Occurs as a mixture of trans isomers.

The isomer mixture can be adsorbed using, for example, chromatographic separation methods, e.g. on a separating agent with selective adsorption activity, e.g. silica gel, aluminum oxide, and the separated isomers subsequently separated in a suitable solvent, e.g. diethyl ether, hexane, etc. The isomeric forms can be separated by elution with acetic acid methyl ester or ethyl ester.

Another chromatographic separation method is gas chromatography.

In some cases, isomeric mixtures can be separated by fractional distillation or fractional crystallization.

The starting materials of general formulas (II) to (■) are known compounds,
It can be produced similarly to known methods described in the literature.

The compounds of general formula (1) are suitable for controlling various animal pests.

The compounds are suitable for controlling insects and typical mites of the order Acarina, in particular for controlling insects.

The compound of general formula (1) can be used, for example, against insects of the following orders and families.

Orthoptera Order: Grasshopper family: Cockroach family: Cockroach family: Termite order: Calotermiteidae (KaIoter)
mitidae) Hemiptera Order: Piesmidae Family: Piesmidae Family: Pentatomidae: Pentatomidae
) Eriosomatidae
) Lecanidae (Lecan i 1dae) Coleoptera Carabidae (Carab 1dae) Cricket beetle family Chinoid beetle family Meal beetle family Cucugidae Cucuj 1 dae (Lecan i 1 dae) Coleoptera family Weevil family Bark beetle family Scarabidae Lepidoptera order Family: Phyticidae Family: Pyraustidae Crambidae Family: Galleriaceae Galleriidae Family: Lyonetiidae Lyonetiidae Family: Pyraustidae Family: Pyraustidae Family: Pyraustidae Family: Crambidae Family: Pyraustidae Family: Crambidae Family: Galleriidae Family: Lyonetiidae Family: Pyraustidae Family: Pyraustidae Family: Crambidae Family: Galleriidae Family: Lyonetiidae (Lyonetiidae) ) killing By adding an acaricide, its insecticidal and/or acaricidal action can be substantially extended and adapted to suit the environment in question.

For example, in particular the following compounds can be added.

Organic phosphorus compound bis-02O-diethyl phosphoric anhydride (TEPP) dimethyl (2,2,2-1-dichloro-1-hydroxyethyl)-phosphonate (trichlorfon) ■, 2-sifuromo 2,2-dichloroethyldimethyl Phosphate (
naled) 2.2-dichlorovinyldimethylphosphate (dichlorophos) 2-methoxycarbamyl-1-methylvinyldimethylphosphgoate (mevinphos) Dimethino I/-1-methyl-2-(methylcarbamoyl)vinylphosphate cis(monocrotophos) ) 3-(dimethoxyphosphinyloxy)-N,N-dimethyl-cis-crotonamide (dicrotophos) 2-chloro-2-diethylcarbamoyl-1-methylvinyldimethylphosphate (phosphamidon) 0.0-diethyl-〇( or 5)-2-(ethylthio)
-Ethylthiophosphate (demeton) S-ethylthioethyl-〇,O-dimethyl-dithiophosphate (thiophene) O20-diethyl-8-ethylmercaptomethyldithiophosphate (pholate) 0.0-diethyl-8-2-(( Ethylthio)ethyldithiophosphonate (disulfotone)O20-dimethyl-8-2-(ethylsulfinyl)ethylthiophosphate (oxydemetonmethyl) 0.0-dimethyl-8-(1,2-dicarboethoxyethyl)dithiophosphate ( malathion) o, o, o
, o-tetraethyl-s, s'-methylene-bis[dithiophosphate J (nithione)〇-ethyl8. S
-dipropyldithiophosphate 02O-dimethyl-8-(N-methyl-N-formylcarbamoylmethyl)-dithiophosphate (formothione) 0.0-)Mef-5-(N-methylcarbamoylmethyl)dithiophosphate (dimethoate) O20-Dimethyl-0-p-nitrophenylthiophosphate (barathion-methyl) 0.0-'; Ethyl-0-p-nitrophenylthiophosphate (parathion) 〇-Ethyl-p-nitrophenyl phenylthiophosphonate (EPN) 0.0-dimethyl-0-(4-nitro-m-tolyl)thiophosphate (fenitrothion) 0.0-dimethyl-0-2,4,5-trichlorophenylthiophosphate (ronnel) 0-ethyl-2. 4.5-1 Lichlorophenylethylthiophosphonate (trichloronate) 0.0-methyl-2,5-dichloro-4-bromphenylthiophosphate (bromophos) 0.0-dimethyl-
(2,5-dichloro-4-iodophenyl)-thiophosphate (iodophenphos) 4jfE3butyl-2-chlorophenyl-N-methyl-
O-methylamide phosphate (clufomate) 0.0-methyl-(3-methyl-4-methylmercaptophenyl) thiophosphate (fenthion) Isopropylamino-ethyl-(4-methylmercapto-3-methylphenyl) -Phosphate 02O-diethyl-〇 -p-(methylsulfinyl)phenyl-thiophosphate (fensulfothion) 0-4: p-(dimethylsulfamide)phenyl] 0.
0-dimethylthiophosphate (famfur) o,o,o',o'-tetramethyl-〇,0'-thiodi p-phenylenethiophosphate 〇-ethyl-8-phenyl-ethyldithiophosphonate 02O-dimethyl-0-( α-Methylbenzyl-3-hydro-cyclotonyl) phosphate 210 rho1-(2
,4-')chlorophenyl)vinyl-diethylphosphate (chlorofenvinphos) 2-chloro-1-(2,4,5-)dichlorophenyl)
Vinyl-dimethylphosphate O-[2-chloro-1-(2,5-dichlorophenylfucovinyl-〇, O-diethylthiophosphate )0.0-diethyl-0-(3-chloro-4-,methyl-2-oxo-2
-H-1-benzopyran-7-yl)-thiophosphate (coumaphos) 2.3-p-dioxanedithiol-
S,S-bis(0,0-diethyldithiophosphate)
(Dioxathion) 5-((6-chloro-2-oxo-3-benzoxazolinyl)methyl]01O-diethyldithiophosphate (Fosalone) 2-(Shed beef cyphosphinyl imino)-1,3-dithiolane 02O -dimethyl-8-[2-methoxy-1,3,4-
Thiadiazol-5-(4H)-oneyl-(4)-methyl]dithiophosphate 02O-dimethyl-8-phthalimidomethyl-dithiophosphate (imidan) 0.0-diethyl-〇-(3,5,6-dolichloro2
-pyridyl)thiophosphate 02O-enethyl-2-pyrazinylthiophosphate (thionazine) 0.0-diethyl-(2-isopropyl-4-methyl-6-pyrimidyl)thiophosphate (diazinone) 0.0-diethyl -〇-(2-quinoxalyl)thiophosphate 0.0-methyl-5-(4-oxo-1,2,3-benzotriazin-3(4H)-yl-methyl)-dithiophosphate (azinphosmethyl) 0. 0-diethyl-8-(4-oxo-1,2,3-benzotriazine-
3(4H)-yl-methyl)-dithiophosphate (azinphosethyl) S-1: (4,6-cyamitsus-
triazin-2-yl)methyl J-0,0-dimethyldithiophosphate (menazone) O20-dimethyl-〇-(3-chloro-4-nitrophenyl)thiophosphate (chlorthion) 0.0-dimethyl-O (or -8) -2-(ethylthioethyl)thiophosphate (amethone-S-methyl) 2-(0,0-dimethyl-phosphoryl-thiomethyl)-
5-Methoxy-pyrone-4-3,4-dichlorobenzyl-triphenylphosphonium chloride 0.0-diethyl-8-(2,5-dichlorophenylthiomethyl)dithiophosphate (fenkapton) 0.0-diethyl-0- (4-methyl-fumarinyl-7
)-thiophosphate (botasan) 5-amino-bis(
dimethylamido)phosphinyl-3-phenyl-1,2
,4-) Riazole (triamiphos) N-methyl-5-(0,0-dimethylthiophosphoryl)
-3-thiavalleramide (vaamidethione) 0.0-diethyl-〇-[2-dimethylamino-4-methylpyrimidyl-(6)-thiophosphate (dioctyl) 0,O-dimethyl-5-(methylcarbamoylmethyl)
-thiophosphate (omethoate) 0-ethyl-0-
(8-4/ Linyl)-phenylthiophosphonate (oxynotiophos) O-methyl-8-methyl-amidethiophosphate (monitol) O-methyl-〇-(2,5-dichloro-4-bromphenyl)benzothio Phosphate (phosvel) o, o,
o,o-Tetrapropyldithiopyrophosphate 3-(dimeth,xyphosphinyloxy)-N-methyl-N-methoxy-cis-crotonamide 0.0-diethyl-8-(N-ethylcarbamoylmethyl)dithio Phosphate (ethoate-methyl) O20-diethyl-8-(N-1'sopropyl-rubamoylmethyl)-dithiophosphate (protoate) S-N~(1-cyano-1-methylethyl)carbamoylmethyldiethylthiol phosphate (cyantoate) S -(2-acetamidoethyl)~02O-dimethyldithiophosphate hexamethylphosphoric acid triamide (Hempa) 0.0-dimethyl-0-(2-chloro-4-nitrophenyl)thiophosphate (dicaptone) 0.0-dimethyl-〇 -p-cyanophenylthiophosphate (cyanox) 〇-ethyl〇-p-cyanophenylthiophosphonate 0.0-'; ethyl〇-2,4-dichlorophenylthiophosphate (dichlorofenthion) 0-2,4-
Di'70rophenyl-〇-methylisopropylamide thiophosphate O2O~diethyl-〇-2.5-dichloro-4-bromophenylthiophosphate (bromophos-ethyl) dimethinol, -p-(methylthio)phenylphosphate 0.0-,: 'Methyl-p-sulfamidophenylthiophosphene, -to-0-Cp-(p-chlorophenyl)abphenyl' 01
O-dimethylthiophosphate (acidoate) 0-ethyl-8-4-chlorophenyl-ethyldithiophosphonate 0-1'subbutyl-8-p-chlorophenyl-ethyldithiophosphonate 0,0-)methyl-8-p-chlorophenylthiophosphate 0.0-dimethyl-8-(p-chlorophenylthiomethyl)-dithiophosphate 0.0-'2ethyl p-chlorophenylmercaptomethyl-dithiophosphate (carbophenothion) 0.0-diethyl-8-p-chlorophenylthio Methyl-thiophosphate 0.0-dimethyl-5-(carboethyl-cyphenylmethyl) dithiophosphate (fuentate) O20-diethyl-8-(carbofluorethoxy-phenylmethyl)-dithiophosphate 02O-dimethyl-S-(carbofluoroethoxy-phenylmethyl) Isopropoxy-phenylmethyl)-dithiophosphate 0.0-diethyl-7-hydroxy-
3,4-tetramethylene coumarinyl thiophosphate (cumitoate) 2-methoxy-4-H-1,3,2-benzodioxaphosphorine-2-sulfide 0.0-diethyl-〇-(5- Phenyl-3-yneoxasilyl)thiophosphate 2-(jethoxyphosphinylimino)-4-methyl-
1,3-dithiolantris-(2-methyl-1-azarinyl)-phosphine oxyto(methyl) 8-(2-'70ro-l-phthalimidoethyl)-〇,
O-diethyldithiophosphate N-hydroxynaphthalimide-diethylphosphate dimethyl-3,5,6-)lichloro 2-pyridylphosphate 0.0-dimethyl-〇-(3,5,6-1lichloro 2
-pyridyl)-thiophosphate S-2-(ethylsulfonyl)ethyldimethylthiolphosphate (dioxyamethone-S-methyl) diethyl)1. -8-2- (ethylsulfinyl)ethyldithiophosphate (oxydisulfoton) bis-0
, O-diethylthiophosphoric anhydride (sulfotep) dimegosol, -4,3-di(carbomethoxy)-1-propen-2-yl-phosphate dimethyl-(2,2,2-1-dichloro-1-butyroyl) Diethyl)phosphonate (butonate) 0.0-
,>Methyl-0-(2,2-dicr7/L/-1-methoxyvinyl)phosphate Hose(dimethylamide)fluorophosphate (Dimefox) 3.4-Dichlorobenzyl-triphenylphosphonium chloride dimethyl-N- Metobyldimethylcarbamoylmethyl-dithiophosphate (formocarbam) 0.0-diethyl-〇-(2,2-dichloro-1-lyloloethoxyvinyl)phosphate 0.0-dimethyl-〇-(2,2-dichloro -1-chloroethoxyvinyl)phosphate 0-ethyl-8,S-diphenyldithiophosphate 0-ethyl-S-benzyl-phenyldithiophosphonate 0.0-diethyl-8-hensyl-thiophosphate 0.0-dimethyl-8- (4-Chlorophenylthiomethyl) dithiophosphate (methylcarbophenothion) O20-dimethyl-5-(ethylthiomethyl)dithiophosphate diisopropylaminofluorophosphate (mipafox) 0.0-dimef-S-(morphol) Nylcarbamoylmethyl)dithiophosphate (morphothion)bismethylamide-phenylphosphate 0.0-dimef-S-
(benzenesulfonyl) dithiophosphate 0.0-dimethyl-(S and 0)-ethylsulfinylethylthiophosphate 0.0-diethyl-〇-4-nitrophenylphosphate triethoxy-impropoxy-bis(thiophosphinyl) disulfide 2-methoxy -4H-1,3,2-henzodioxabosphorin-2-oxide octamethylpyrophosphoramide (Schladan) his(dimethoxythiophosphinyl sulfide)-phenylmethane N, N, N', N' -Tetramethyldiamide fluorophosphate (Dimefox) 0-phenyl-0-p-nitrophenyl-methanethiophosphonate (Coretsub) O-methyl-〇-(2-chloro-4-tert-butyl-phenyl)-N- Methyldithiophosphate (Naluren) 〇-Ethyl〇-(2,4-dichlorophenyl)-phenylthiophosphonate 0.0-diethyl-〇-(4-methylmercapto-3,
5-dimethylphenyl)-thiophosphate 4.4'-
Bis-(0,0-dimethylthiophosphoryloxy)-diphenyldisulfide 0.0-(β-chloroethyl)-0-(3-chloro-4-methyl-fumarinyl-7)-phosphate 5-(1-phthalimide ethyl)-0,0-diethyldithiophosphate 0.0-dimethyl-〇-(3-chloro-4-diethylsulfamylphenyl)-thiophosphate O-methyl-
〇-(2-Carboisopropoxyphenyl)amidethiophosphate 5-(0,0-dimethylphosphoryl)-6-chloro-bicyclo(3,2,0)-hebutadiene-(1,5)O-
Methyl-〇-(2-i-propoxycarbonyl-■-
Methyl vinyl)ethylamide thiophosphate nitrophenols and derivatives 4.6-sinitro 6-methylphenol sodium salt [dinitrocresol codinitrobutylphenol (2,2',2''-triethanolamine salt) 2-cyclohexyl-4, 6-sinitrophenol [Zinex] 2-(1-methylfer)-4,6-sinitrophenylcrotonate Shidinocap] 2→K2B-4,6-dinitrophenyl-3methyl-butenoate [Binapacryl ] 2-IE2 phthyl-4,6-sinitrophenyl-cyclopropionate 2→p-2-butyl-46-sinitrophenyl-isopropyl-carbonate Zipton] Others pyrethrin I pyrethrin ■ 3-allyl-2-methyl-4 -Oxo-2-cyclopenten-1-yl chrysanthemamate (Allethrin) 6-chloropiperonyl chrysanthemamate (Parsulin) 2.4-dimethylbenzyl chrysanthemamate (dimethrin) 2.3,4,5-tetrahydrophthalimidomethy Lucrysantemamate 4-chlorobenzyl-4-chlorophenylsulfide [chloropenside] 6-methyl-2-oxo-1,3-dithiolo-[4゜5
-b]-Quinoxaline [chinomethionate] (1)-3
(2-furfuryl)-2-methyl-4-oxoclobent-2-enyl (1)-(cis+trans)chrysanthemum monolupoxylate [fresrin] 2-t; sooyl-indan-1,3- Dione [Vinton] N'-(4-chloro-2-methylphenyl)-N.

N-dimethylformamidine (chlorophenamidine) 4-chlorobenzyl-4-fluorophenyl-sulfide (fluoropenside) 5.6-')'70 rho-1-phenoxycarbanyl-2
-Trifluoromethyl-benzimidazole (Fenozaflor) p-Chlorophenyl-p-chlorobenzenesulfonate (Ovex) p-J70 lophenyl-benzenesulfonate (Fuenson) p-chlorophenyl-2,4,5-tri'70 phenylsulfone (Tetrasifon) ) p-chlorophenyl-2,4,5-11,1 chlorophenyl sulfide (tetrasal) p-chlorobenzyl-p-chlorophenyl sulfide (chlorbenside) 2-thio-1,3-dithiolo-(5,6- Quinoxaline (thioquinox) prof'-2-yl-(4-tert-butylphenoxy)-
Cyclohexyl sulfide (propargyl) formamidine 1-dimethyl-2-(2'-methyl-41-chlorophenyl) formamidine (chlorozenamidine) ■-methyl-2- (2'-methyl-4'-chlorophenyl)-
Formamidine 1-methyl-2-(2'-methyl-4'-bromphenyl)-formamidine 1-methyl-2-(2',4'-dimethylphenyl)-
Formamidine 1-n-butyl-1-methyl-2-(2'-methyl-4
'-70lophenyl)-formamidine nimethyl-1
-(2'-methyl-4'-chloroanilino-methylene) 2-(2"-methyl-4"-chlorophenyl)-formamidine 1-n-butyl-2-(2'-methyl-4'-chlorophenyl-imino )-pyrrolidineurea N-2-methyl-4-chlorophenyl-N,N'-dimethyl-thioureacarbmate 1-su7+ruN-methylcarbamate (carbaryl) 2-t-y-nyl-4-chlorophenyl carbamate 4
-Dimethylamine-3,5-xylyl-N-methylcarbumate 4-dimethylamino-3-tolyl-N-methylcarbamate (aminocarb) 4-Methylthio-3,5-xylyl-N-methylcarbamate (methylcarba) 3. 4.5-Trimethylphenyl-N-methylcarbamate 2-chlorophenyl-N-methylcarbamate (CPM
C) 5-chloro-6-oxo-2-norbornane-carbonitrile-〇-(methylcarbamoyl)-oxime 1-(dimethylcarbamoyl)-5-methyl-3-pyranyl-N,N-dimethyl-carbonitrile (dimethylcarbamoyl) ) 2.3-dihydro-2,2-dimethyl-7-benzofuranyl-N-methylcarbamate (carbofuran) 2-methyl-2-methylthio-propionaldehyde-〇-(
Methylcarbamoyl)-oxime (aminocarb) 8-quinardyl-N-methylcarbamate and its salts (methyl)l, -2-isopropyl-4-(methylcarbamoyl)-carbanilate m-(1-ethylpropyl)phenyl-N- Methylcarbumate 3.5-cy→kun3butyl-N-methylcarbamate m-
(1-) f ruphthyl) phenyl-N-methylcarbumate 2-isopropylphenyl-N-methylcarbamate 2-427'tylphenyl-N-methylcarbamate m-tolyl-N-methylcarbamate 2.3-xylyl-N-methyl Carbamate 3-isopropylphenyl-N-methylcarbamate 3-43butylphenyl-N-methylcarba) 1to3-11.2butylphenyl-N-methylcarbamate 3-isopropyl-5-methylphenyl-N-methylcarbamate (Promecarp) 3.5-diisopropylphenyl-N-methylcarbumate 2-chloro-5-isopropylphenyl-N-methylcarbumate 2-chloro-4,5-dimethylphenyl-N-methylcarbumate 2-(1,3-dioxolane- 2-yl)phenyl-N
-Methyl carbamate (dioxacals 0) 2-(4,
2-(L3-dithiolane-2 -yl)-N,N-dimethylcarbumate 2-(1,3-dithiolan-2-yl)phenyl-N,
N-dimethylcarbamate 2-iso70-boxyphenyl-N-methylcarbamate (aminocarb) 2-(2-propynyloxy)phenyl-N-methylcarnomate 3-(2-propynyloxy)phenyl-N-methylcarbamate 2-dimethylaminophenyl -N-methylcarbamate 2-diallylaminophenyl-N-methylcarbamate 4-diallylamino-3,5-xylyl-N-methylcarbamate (alixycarb) 4 dQzochenyl-N-methylcarbamate 2.3-
Dihydro-2-methyl-7-benzofuranyl-N-methylcarbamate 3-methyl-1-phenylpyrazol-5-yl-N
, N-dimethylcarbamate 1-isopropyl-3-methylpyrazol-5yl-N
, N-dimethylcarbamate (isolane) 2-dimethylamino-5,6-dimethylpyrimidin-4-ylN,
N-dimethyl-carbamate 3-methyl-4-dimethylaminomethyleneiminophenyl-N-methylcarnocmate 3.4-dimethylphenyl-N-methylcarbamate 2-cyclopentylphenyl-N-methylcarbamate 3-dimethylamino-methyleneiminophenyl -N-methylcarbamate (formethanate) and its salts 1-methylthio-ethylimino-N-methylcarbamate (methomyl) 2-methylcarbamoyloxyimino-1,3-dithiolane 5-methyl-2-methylcarbamoyloximino-1
,3-oxythiolane 2-(1-methoxy-2-propoxy)phenyl-N-
Methylcarno〈mate 2-(1-butyn-3-yl-oxy)phenyl-N-
Methylcarbanote 1-dimethylcarbamyl-1-methylthio-〇-methylcarpamy-formoxime 1-(2'-cyanoethylthio)-〇-methylcartumamy-acetaldoxime 1-methylthio-〇-carbamy-acetaldo oxime 0-(3-2-butylphenyl)-N-phenylthio-N-methylcarbamate 2,5-dimethyl-1,3-dithiolane-2(0-methylcarbamyl)-aldoxime 0-2-diphenyl-N
-Methylcarbamate 2-(N-methylcarbamyl-oximino)3-chloro-bicyclo[2,2,1]hebutane 2-(N-methylcarbamyl-oximino)-bicyclo[2,2,1]hebutane 3-isopropylphenyl-N-methyl-N-chloroethyl-carno-methyl-3-isopropylphenyl-N-methyl-N-methylthiomethyl-carbamate 0-(2,2-dimethyl-4-chloro-2, 3-dihydro-7-benzofuranyl)-N-methylcarlenocmate 0-(2,2,4-t-rifthyl-2,3-dihydro
-7-Benzofuranyl) -N-methylcarbamate O-naphthyl-N-methyl-N-acetyl-carnocmate 0-5,6,7,8-tetrahydronaphthyl-N-methyl-carnocmate 3-isopropyl-4-methylthio-phenyl -N-methylcarbanote 3.5-dimethyl-4-methoxy-phenyl-N-methylcarbamate 3-methoxymethoxy-phenyl-N-methylcarrenomate 3-allyloxyphenyl-N-methylcarbamate 2-propargyloxymethoxy -Phenyl-N-methyl-carbamate 2-allyloxyphenyl-N-methyl-carbamate 4-methoxycarbonylamino-3-isopropylphenyl-N-methylcarbamate 3,5-dimethyl-4-methoxycarbonylamino-phenyl-N-methyl -carbamate 2-γ-methylthiopropylphenyl-N-methyl-carnocmate 3-(α-methoxymethyl-2-propenyl)phenyl-N-methyl-carbamate 2-chloro-5-tert-butyl-phenyl-N-methyl-
Carbamate 4-(methyl-proparkylamino)-3,5xylyl-N-methyl-carbamate 4-(methyl-γ-chloroallylamino)-3゜5-
Xylyl-N-methyl-carbamate 4-(methyl-β
-chloroallylamino) at5-xylyl-N-methyl-carbamate 1-(β-acetoxycarbonylethyl)-3methyl-5-pyrazolyl-N,N-dimethyl-carlenocmate 3-methyl-4-(dimethylamino -Methylmercapto-methyleneimino)phenyl-N-methylcarnocmate 1,3-bis(carbamoylthio')-2-(N)N-
dimethylamino)-propane hydrochloride 5.5-dimethylhydroresorcindimethylcarnocmate 2-[ethyl-propargylaminoco-phenyl N-methylcarbamate 2-[methyl-propargylamine]-phenyl N-methylcarnocmate 2-reque 0ropargylamino]-phenyl-N-methylcarbamate 4-[ropargylamino)-3-t-crew N-methylcarbamate 4-[dipropargylamino]-3,5-xylyl-
N-Methylcal/〈mate 2-[allyl-isopropylaminoco-phenyl-N-
Methylcarnocmate 3-[allyl-isopropylaminoco-phenyl-N-
Methyl carbamate chlorinated hydrocarbon r-hexachlorocyclohexane [camexane; lindane; γHCH] 1.2,4,5,6,7,8,8-octachloro-3α
.

4.7,7cl'-tetrahydro-4,7-methyleneindan [chlordane] 1.4,5,6,7,8,8-heptachloro-3α,4
゜7.7α-tetrahydro-4,7-methyleneindan [heptachlor] 1.2,3 >4 > 10 > 10-hexachloro-1,4゜4α,5,8,8α-hexahydro-endo-1,4 -Exo-5,8-dimethanenaphthalin [Aldrin] 1.2,3.4,10,10-hexachloro-6,7 eboxy 1,4,4αt 5 t 6 + 7 t 8
t8α-octahydro-exo-1,4-endo-
5,8-dimethanonaphthalene [ciflorin] 1.2,3,4,10,10-hexachloro-5,7-
Nipoxy 1, 4. , 4α, 5, 6, 7, 8, 8α
-Occhydroendo-5,8-dimethanonaphthalene [Endrin] The compounds of general formula (I) can be used alone or together with suitable support substances and/or additives.

Suitable carrier substances and additives may be solid or liquid and include the substances customary in formulation technology, such as natural or recycled substances, solvents, dispersants, wetting agents, adhesives, thickeners,
Binders and/or fertilizers.

For application, the compounds of general formula (I) can be processed into powders, emulsions, concentrates, granules, dispersions, sprays, solutions or suspensions in the formulations customary in application technology.

The pest control agent is prepared by adding the active ingredient of general formula (I) and optionally a dispersant or solvent that is inert to the active ingredient.
It is produced by a conventional method by uniformly mixing and grinding with a suitable supporting material.

The effective fraction can be made into the following dosage form and used.

Solid preparations: powders, dusting powders, granules, coated granules, impregnated granules and homogeneous granules Liquid preparations: a) Water-dispersible active fraction concentrates, water consolation agents, pastes, emulsions b) Solution solid preparations (powders, Spraying agent) is obtained by mixing the active fraction with a solid carrier.

Suitable carriers include, for example, kaolin, kuruk, bolus, loess, chalk, lime, lime powder, acpargite, tomite, diatomaceous earth, precipitated silicic acid, alkaline earth metal silicates, aluminum silicates. Sodium and potassium (
Fertilizers like: rice husk, bark powder, sawdust, nut powder, cellulose powder, plant extracts There are plant material powders such as residues of carbon dioxide, activated carbon, etc., which can be used alone or in mixtures with each other.

Granules are prepared by dissolving the effective fraction of general formula (I) in an organic solvent,
It can be produced very easily by applying the solution thus obtained to a granular mineral, such as attapulgite, S io 2, granular calcium, bentonite, etc., and then evaporating the organic solvent.

In addition, compounds capable of polymerizing the effective fraction of general formula (1) (urea/
Polymer granules can also be prepared by mixing with formaldehyde: dicyanodiamide/formaldehyde: melamine/formaldehyde, etc.) and then carrying out careful polymerization.

With this method, no effect remains on the active fraction and granulation begins during gel formation.

It is also advantageous to impregnate the finished porous polymer granules (urea/formaldehyde, polyacrylonitrile, polyester, etc.) with the effective fraction having a defined surface area and a desired predetermined adsorption/desorption ratio.

Impregnation with the active ingredient takes place, for example, in solution (in a low-boiling solvent) and then the solvent is removed.

Such polymer granules are preferably 300 to 6009/
It can also be applied using a sprayer in the form of fine granules having a bulk weight of 1.

It can also be sprayed by airplane over a wide area where useful plants can be cultivated.

Granules can also be obtained by aggregating the carrier material with the active fraction and additives and then grinding.

Additives to stabilize the active fraction in these mixtures, and/or
or non-ionic, anionic, e.g. to improve the adhesion of the active ingredient on plants and plant parts (adhesives and glues) or to ensure good wetting (watering agents) and dispersibility (dispersants). Polymer and cationic substances may also be added.

For example, the following substances are suitable: niolein/lime mixtures, cellulose derivatives (methyl cellulose, carboxymethyl cellulose), 5-15 ethylene oxide groups per molecule and 8 in alkyl groups.
- Hydroxyethylene glycol ethers of monoalkyl and dialkylphenols having 9 carbon atoms; lignin sulfonic acid, its alkali metal and alkaline earth metal salts; polyethylene glycol ether (carbowax), 5-20 per molecule; fatty alcohol bolik IJ coal ether containing 8-18 carbon atoms in the ethylene oxide group and the fatty alcohol moiety: condensation product of ethylene oxide, propylene oxide, polyvinylpyrrolidone, polyvinyl alcohol,
Condensation products of urea and formaldehyde, and latex products.

Water-dispersible concentrates of the active fraction, such as aquariums, pastes and emulsion concentrates, are preparations that can be diluted with water to the desired concentration.

They are free from active fractions, carrier materials, optionally additives that stabilize the active ingredient, surface-active substances, and antifoaming agents, and optionally solvents.

Irrigation agents and pastes are obtained by mixing and grinding the active fraction with dispersants and pulverulent carrier materials until homogeneous in suitable equipment.

Suitable carrier materials include, for example, those mentioned in the case of solid formulations.

It may also be advantageous to use mixtures of different support materials.

As the dispersant, the following can be used.

For example, condensation products of sulfonated naphthalene and sulfonated naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, alkali metal salts, ammonium salts and alkaline earth metal salts of lignin sulfonic acid, Alkylaryl sulfonates alkali metal salts and alkaline earth metal salts of dibutylnaphthalene sulfonic acid,
Salts of fatty alcohol sulfates, such as sulfated hexadecanol, heptadecanol, octadecanol, and salts of sulfated fatty alcohol glycol ethers, sodium salt of oleyl methyl tauride, di-t-acetylene glycol, dialkyl di lauryl ammonium chloride, and fatty acid alkali metal salts and alkaline earth metal salts.

Suitable defoamers include, for example, silicone oils.

The effective fraction is mixed with the above additives, crushed and sieved so that the solid component does not exceed a particle size of 0.02-0.04111 m in the case of irrigation agents and 0.03 Wil+ in the case of pastes.

To prepare emulsion concentrates and pastes, dispersants, organic solvents and water as described above are used.

Suitable solvents include, for example, alcohol, benzene, xylene, toluene, dimethyl sulfoxide, and
There are mineral oil fractions that boil in the 350°C range.

The solvent should be virtually odorless, non-phytotoxic and inert to the active ingredient.

Furthermore, the formulation according to the invention can be used in the form of a solution.

For this purpose, one or more effective fractions of the general formula (I) are dissolved in a suitable organic solvent, solvent mixture or water.

As organic solvents it is possible to use aliphatic and aromatic hydrocarbons, their chlorinated derivatives, alkylnaphthalenes, mineral oils, alone or in mixtures with one another.

In the above-mentioned formulations the content of active substance is between 0.1 and 95
%; a related consideration is that when applying the formulation on an airplane or other suitable equipment, a concentration of 99.5% or higher or a pure active fraction should be used.

An effective fraction of general formula (I) can be prepared, for example, as follows.

Powder.

The following substances are used to prepare a) 5% and b) 2% powder: a) Active ingredient 5 parts talc
95 parts b) Active ingredients: 2 parts silica, 1 part talc
The 97 parts effective portion is mixed with the carrier material and milled into granules.

Use the following materials to prepare 5% granules: Active fraction 5 parts epichlorohydrin
0.25 parts cetyl polyglycol ether 0.25 parts polyethylene glycol 3
．． 50 parts kaolin (particle size 0.3-0.8 mm)
91 parts of the active ingredient is mixed with epichlorohydrin;
It is then dissolved in 6 parts of acetone, and then polyethylene glycol and cetyl polyglycol ether are added.

The solution thus obtained is sprayed onto kaolin and the acetone is subsequently evaporated under reduced pressure.

Irrigation agent.

a) 40% b) and c) 25% and d) 10% The following ingredients are used in the formulation of the water conservancy: a) Active fraction 40 parts Sodium lisninsulfonate 5 parts Sodium dibutyl-naphthalene sulfonate 1 part 54 parts 25 parts 4.5 parts Silicic acid effective fraction Calcium likuninsulfonate Champagne chalk/oxyethyl cellulose mixture (1:1) 1.9 parts b) Sodium dibutylnaphthalene sulfonate 1.5 parts Silicic acid 19.5 parts Champagne chalk 19.5 parts kaolin
28.1 Part C) Active ingredients
25 parts Octylphenoxypolyoxyethylene-ethanol 2.5 parts Chapentyoke/oxyethylcellulose mixture (1:1) 1.7 parts Sodium aluminum silicate 83 parts Diatomycin
16.5 parts kaolin
46 parts d) Mixture of effective fraction saturated fatty alcohol sulfuric acid sodium salts 3 parts naphthalene sulfonic acid/formaldehyde condensate
5 parts kaolin and 82 parts active ingredients are intimately mixed with additives in a suitable mixer;
The mixture is then milled with suitable mills and rollers.

An aquarium is obtained which, when diluted with water, gives a suspension of any desired concentration.

Emulsifiable concentrate.

The following materials are used to formulate a) 10% and b) 25% emulsifying concentrates: a) active fraction 10 parts epoxidized vegetable oil 34 parts from fatty alcohol polyglycol ether and alkylaryl sulfonic acid calcium salt Powerful composite emulsifier 34 parts dimethylformamide 40 parts xylene
43.2 Part b) Active ingredients
25 parts epoxidized vegetable oil
2.5 parts Alkylaryl sulfonate/fatty alcohol polyglycol ether mixture 10 parts Dimethylformamide 5 parts Xylene
57.5 parts Emulsions of any desired concentration can be prepared from the above concentrate by dilution with water.

Spraying agent.

Use the following aliquots to formulate a 5% propellant.

Active ingredients 5 parts shrimp chlorohydrin 1 part petroleum benzine (boiling range 1
60-190°C) 94 parts Next, the present invention will be explained in detail based on Examples.

Example 1 ■, 4-cyclohexyloxy-phenol 19.29 and 1 from-3- in 2-dimethoxyethane 150-
To a solution of methyl-2-penteno 1.6.49% in anhydrous ethanol 90% within 6 hours with stirring at room temperature
A solution of 649% potassium hydroxide was added dropwise.

After adding the base, the mixture was stirred at room temperature for an additional 15 hours.

For work-up, the precipitated potassium bromide was filtered off, the filtrate was evaporated in vacuo and the residue was taken up in hexane and cooled with water at 10%
Washed three times with caustic potash and then with water until neutral.

After drying the organic phase over sodium sulfate, filtration and complete removal of the solvent in vacuo, pure 1-cyclohexyloxy-4-(3-methyl-2-pentenyl-1-oxy)-benzene ( n20=1.5265) remained.

Example 2 4-hydroxydiphenyl ether 28g, acetone 1
50d, anhydrous potassium carbonate powder 26.69 and hexamethylphosphoric triamide 50-30 at 55°C.
Within minutes, with stirring, 22 doses of 1,3 dichloropropene were added dropwise and the mixture was kept at reflux temperature for a further 18 hours.

Subsequently, the reaction mixture was poured onto approx. 1.5 portions of ice water and extracted repeatedly with diethyl ether.

The combined ether solution was washed four times with 10% potassium hydroxide and repeatedly with saturated sodium chloride solution until a neutral reaction was completed.

After drying the ether solution over sodium sulfate, the solvent was completely removed in vacuo to yield pure 3-(pphenoxy)-phenoxy-1-chloro-1-propene.

n2021.5819° Example 3 6.39 kg of 90% potassium hydroxide powder was introduced in small portions at about 10° C. into a solution of 18.69 kg of 4-hydroxydiphenyl ether in 125 dimethyl sulfoxide and dissolved.

Add 1-bromo-4-methyl-3-hexene 17 to this solution.
．． 89- was added dropwise within 3 hours with stirring at 10-15°C.

After adding the halide, the mixture was further stirred at room temperature for 20 hours.

For work-up, the reaction mixture was poured into approximately 1 portion of ice water and the mixture was repeatedly extracted with diethyl ether.

The combined ethereal phases were washed twice with water, with a 20% aqueous solution of potassium hydroxide, and finally once again with water until neutral.

After drying the ether phase over sodium sulfate, the solvent was distilled off and the remaining oily product was purified by chromatography on silica gel (eluent: ether-
hexane 1:5).

Pure 1(p-phenoxy)-phenoxy-4-methyl-3hexacene was obtained (n29°=1.5580)
.

The following compounds were produced in the same manner as in Examples 1 to 3: Reference Example l Dy5dercus fasciatus (Dy5dercus fasciatus)
Suppressive effect on the larvae of Deisdercus fasciatls) Ten larvae of Deisdercus fasciatolus, 8 to 10 days before molting into adults, were treated occasionally with an acetonic active ingredient solution.

The larvae were kept at 28°C and a relative humidity of 80-90°C.

As feed, the animals were fed pre-swollen cotton seed meal.

After approximately 10 days, ie, as soon as the control animals had completely molted into adults, the number of normal adults was determined.

The compounds according to Examples 1 to 3 show a good effect in the above tests.

Reference example 2 Spodoptera litoralis (5podoptera 1
Contents: 130-40 active ingredients in a flask containing 130-
In the other flask with rIIg, content 175 m, 9 Spodoptera littoralis eggs were placed.

Both flasks were connected with an intermediate tube piece and left at 25°C.

The inhibitory effect was evaluated after 5-6 days.

The compounds according to Examples 1 to 3 showed a good effect in the said tests.

Claims (1)

[Scope of Claims] 1 General formula: [In the formula, R3 represents hydrogen, halogen, an alkyl group having 1 to 4 carbon atoms, a vinyl group or an ethynyl group, and R
2 represents hydrogen, halogen, methyl group, or ethyl group, or R1 and R2 together form a cyclopentyl ring or cyclohexyl ring, and R3 represents hydrogen, halogen, methyl group, ethyl group, or 1 to 4 ethyl groups; represents an alkoxy group having carbon atoms, R4 represents hydrogen, halogen or a methyl group, R6 represents hydrogen or halogen, or R
3 and R5 together form a carbon-carbon bond or an oxygen bridge, R6 represents hydrogen, a methyl group or an ethyl group (wherein R8 is hydrogen, halogen, alkyl having 1 to 4 carbon atoms) or an alkoxy group having 1 to 4 carbon atoms), Y is bonded to the oxygen phenyl nucleus, and m and n each represent 0 or l]
To prepare an ether derivative of the general formula: [In the formula, R7 and Y represent the above-mentioned ones, and M represents a metal or hydrogen].
A method for producing an ether derivative, characterized in that R3, R,, R5, R6, m and n represent the above-mentioned compounds, and X represents a halogen.