JPS6011005B2 - pest control agent - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a pest control agent containing a substituted phenyl derivative as an active ingredient.

The active ingredient is a compound corresponding to the following general formula (1).

[In the formula, R, ' is a cyclohexyl group, a cyclohexyloxy group, or a group of the following formula: , , (R5 represents a C,1C3-alkyl group, formyl group or acetyl group) or a direct bond, R7 represents hydrogen, halogen, a C,1C5-alkoxy group or a C,1C5-alkyl group ), Z
represents -○-, -NH-, or (R6 represents Mizuhata or a C,1C3-alkyl group), this moiety is bonded to the phenyl nucleus, and R2 is hydrogen or C,1C3- represents an alkyl group, R3 is one COO, (C,1C5-alkoxy)carbonyl group, (C31C5-alkenyloxy)carbonyl group, (C31C5-alkynyloxy)carbonyl group, cyclohexyloxycarbonyl group, phenoxy a carbonyl group, a (C3-C5-halogenalkenyloxy)carbonyl group, a cyano group, or a carbamoyl group substituted with one or two C,1C5-alkyl groups, C31C5-alkenyl groups or C3-C5-alkynyl groups; In this case, the substituent of the carbamyl group is the nitrogen atom to which it is bonded, and optionally an oxygen atom,
A 5- or 6-membered saturated heterocyclic ring containing a sulfur atom or 80 nitrogen atoms in the ring may be formed, R4 represents hydrogen, a methyl group or an ethyl group, R8 represents hydrogen, a halogen, Represents a methyl group or an ethyl group.

]Halogen is fluorine, chlorine, bromine or iodine.

The alkyl group or alkoxy group represented by R5, R6 and R7 may be linear or branched.

Groups of this type include, for example, methyl, ethyl, n-propyl, isopropyl, i-, n-, sec- and ter
t-butyl, n-, sec- and iso-bentyl, methoxy, ethoxy, propoxy, n-, lso- and s
There are ec-butoxy and n-pentoxy. The alkoxy moiety, alkenyloxy moiety, alkynyloxy moiety and haloalkenyloxy moiety of the alkoxycarbonyl group, alkenyloxycarbonyl group, alkynyloxycarbonyl group or haloalkenyloxycarbonyl group represented by R3 may be linear or branched.

Examples include methoxy, ethoxy, n-propoxy, isopropoxy, sec-butoxy, allyloxy, methacryloxy, propargyloxy, and chlorallyloxy. The alkyl, alkenyl or alkynyl substituents of the carbamoyl group R3 may be branched or straight chain. Examples of this type of carbamoyl group R3 include monomethylcarbamoyl group, monoethylcarbamoyl group, dimethylcarbamoyl group, diethylcarbamoyl group, monoallylcarbamoyl group, monoisopropylcarbamoyl group, and diallylcarbamoyl group. and 2-buty-3-ynyl-carbamoyl group. When the carbamoyl radicals 3 form a heterocycle together with the nitrogen atom to which they are bonded and optionally another heteroatom, examples thereof include a morpholine ring, a piberidine ring or a pyrrolidine ring.

Particularly advantageous compounds include general formula (1) in which R is a cyclohexyl group, a cyclohexyloxy group, or a group (Y in the group).
represents -○ -1, 1C Koichi, , 1C ratio○ -, 1OCH2, 1NH-, is bonded to the phenyl nucleus), and R2 represents hydrogen, a methyl group or an ethyl group, R3 is a carboxyl group, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxy group, sec-butoxycarbonyl group, cyclohexyloxycarbonyl group, phenoxycarbonyl group, allyloxycarbonyl group, chlorallyloxycarbonyl group, bro Pargyloxycarbonyl group, monomethylcarbamoyl group, monoethylcarbonyl group, monoisopropylcarbamoyl group, monosec-butylcarbamoyl group, monoallylcarbamoyl group, diethylcarbamoyl group, diallylcarbamoyl group , 2-buty-31-carbamoyl group, N-piveridinocarbonyl group, n-morpholinocarbonyl group or cyano group, R4 represents hydrogen or a methyl group, R5 represents a formyl group or an acetyl group, A compound in which R6 represents hydrogen or a methyl group, R7 represents hydrogen, a C,1C3-alkyl group, a chlorine atom, a methoxy group, or an ethoxy group, and R6 represents a chlorine or methyl group.

Compounds that are advantageous from the viewpoint of action are represented by the general formula (1), and
R, represents a group (Y in the group represents 10-, or 1C string-, Z represents -○1, 1C ratio○-, 1NH1, or, R2 represents a methyl or ethyl group, R3 is a methoxycarbonyl group, an ethoxycarbonyl group, an isopropoxycarbonyl group, a sec-butoxycarbonyl group, a cyclohexyloxycarbonyl group, a mo/ethylcarbamyl group, a diethylcarbamyl group, a monoisopropylcarbamoyl group group, monoallylcarbamoyl group, N-piveridinocarponyl group, or cyano group, R4 represents hydrogen or methyl group, and R7 represents hydrogen, methyl group, ethyl group, chlorine, methoxy group, or ethoxy group It is a compound.

In the general formula (1), R represents a group, Z represents -○-, R2 represents a methyl group or an ethyl group,
R3 is a methoxycarbonyl group, an ethoxycarbonyl group,
isopropoxycarbonyl group, sec-butoxycarbonyl group, diethylcarbamyl group (represents a motoethylcarbamyl group or cyano group, R4 represents hydrogen, R
Particular preference is given to compounds in which 7 represents hydrogen, chlorine or ethyl.

A more advantageous compound is a compound in which R, in the formula (1) represents an unsubstituted pendyl group, Z represents -○-, R2 represents a methyl group, and R3 represents a methoxycarbonyl group, an ethoxycarbonyl group, a It represents a tylcarbamoyl group or a cyano group, and R4 represents hydrogen. General formula (1
) is prepared in a conventional manner, for example by the following method: A
) B) or and C> General formula (0) to. In (K), Z and R, ~R, o represent those described in general formula (1), × is halogen,
In particular, it represents chlorine or bromine, R9 represents a C,~-alkyl group, phenyl group, or p-chlorophenyl group,
Me represents an alkali metal, in particular sodium or potassium, and R and o represent a C, to C4-alkyl group, a C3-C4-alkenyl group, a C3-C4-alkynyl group or a cyclohexyl group.

Suitable chlorine in reactions A, B and C are alkali metal or alkali metal hydrides, amides, alkoxides, hydroxides or carbonates.

The starting materials of the general formula (K) are preferably obtained by alkaline hydrolysis of the corresponding esters.

According to method B, the compound of general formula (1) has general formula (N)
is prepared by reacting the ketone with the anion of a dialkylphosphonic acid converter in an inert solvent [Horner reaction: see, for example, J. et al. 0rg. Chem
．． 25, 1232-34 (1960), and J. 0rg
．． Chem. 30, 68Nf (1965)]. (2) The compound of general formula (1) in which Y and/or Z represent a group is suitably produced by acylation or alkylation of -NH according to the following reaction formula: or in the above formula, R2 to R8 are represented by the general formula ( 1), R' represents a cyclohexyl group or a group, and Z'
'Ma-○-, or the moiety is bonded to the phenyl nucleus), and Y' is -○1, 1C payment-
-, , -- Represents C ratio 0-, -OC ratio- or direct bond.

As acylating agent, for example acetyl chloride is used in the presence of a base such as acetic-formic anhydride, acetic anhydride or a tertiary amine. The reaction to produce the active ingredient of general formula (1) can be carried out at normal pressure in a solvent and diluent inert to the reactants, such as aromatic hydrocarbons such as benzene, tolueso, xylene; tetrahydrofuraso, dioxane. , dialkyl ethers; N.N-dialkylated amides, such as dimethylformamide; alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, sulfoxides, ketones, such as acetone, methyl ethyl ketone, or cyclohexanone.

The reaction temperature ranges from 0 to 14,000, but from 10 to 70
Advantageously, the range qo. General formula (0), (m
), (N), (of) and (leg) are known compounds.

For example, compounds of the general formula (skin) are described in J. 0rg. Che
m. It can be produced by the method described in 195 Tanou, page 24, 434. In Methods A, B and C, the general formula (1
) Possible geometric isomers are generated in various ways during the preparation of compounds. The compounds described above are, in part, a mixture of cis and trans isomers, as may occur during synthesis or after purification. The pure trans isomer of general formula (1) is
For example, when synthesizing the active ingredient, do you use pure 3-alkyl-(or 314-dialkyl-)4-halogen/-2-trans-butenecarboxylic acid derivatives (J.A.
．． C. S. (Refer to p. 6225 of 1999), or by fractional crystallization, fractional distillation, or gas or adsorption chromatography methods that separate cis/trans isomer mixtures.

The compounds of general formula (1) are used for the control of animal and plant pests.

It is particularly suitable for controlling insects of the following families: grasshoppers (Tetti), crickets (Ghi11i), mole crickets (G11otalpi), cockroaches (B1atti), assassin bugs ( Reduviidae) Phynhocoriae Bedbug family Cimjcidae Delphac
idae) Aphidae (Aphididae) Diaspididae (Pseudococcidae) Scarabaeidae (Scarabaei) Scarabaeidae (DesMae) Cocciidae (Cocciidae) Measles Fallopiant (Tenebrionidae) (Chr.
$omeli ship e) Bean weevil fee (Bruchi ship e)
) Lymatri; dae Noctjndae Lymatri; dae Lymatriidae (PMali) Cicidae TipuMae TipuMae SPmoidae Lymatriidae Trypetidae) House fly feed (Muscj) Blow fly feed (Calljphoridae) Human flea feed (P-skin base) Broaden the range of action and kill insects by adding other insecticides and/or acaricides as well as insect attractants. The action can be adapted to special circumstances.

Organic phosphorus compound bis-010-jethyl phosphate anhydride (TEPP) Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate (trichlorfon) 1,2-dibromo-2,2-dichloroethyl dimethyl phosphate (
naled) 2,2-dichlorovinyldimethylphosphate (dichlorofuos) 2-methoxycarbamyl-1-methylvinyldimethylphosphate (mevinfuos) dimethyl-1-methyl-2-(methylcarbamoyl) vinylphosphate cis(monocrotofuos) 3 -(dimethoxyphosphinyloxy)-N・N-dimethylcis-crotonamide (dicrotophos) 2-chloro-2-diethylcarbamoyl-1-methylvinyldimethylphosphate (phosphamidon)○・0-jethyl○ (or S
)-2-(ethylthio)-ethylthiophosphate (demeton) S-ethylthioethyl-0,0-dimethyl-dithiophosphate (thiometone)○,0-diethyl-S-ethylmercaptomethyldithiophosphate (pholate) )○・0-Diethyl-S-2-[(ethylthio)ethyl]dithiophosphate (disulfotone) 0.0-dimethyl-S-2-(ethylsulfinyl)ethylthiophosphate (oxydemetonmethyl)○・0-dimethyl-S-(102-dicarboethoxyethyl)dithiophosphate (malathion)○・0.0・〇-tetraethyl S・S'-methylene-bis[dithiophosphate] (ethion)○-ethyl-S・S- Dipropyldithiophosphate○・0-dimethyl-S-(N-methyl-N-formylcarbamoylmethyl)-dithiophosphate (formothion)○・0-dimethyl-S-(N-methylcarbamoylmethyl)dithiophosphate- (dimethoate)
0,0-dimethyl-○1p-nitrophenylthiophosphate (parathion-methyl)○,0-diethyl-○1p-nitrophenylthiophosphate (parathion)○
-ethyl-○1p nitrophenyl phenylthiophosphonate (EPN)○・0-dimethyl-○1 (4-nitrom-tolyl) thiophosphate (fenitrothion)
0,0-dimethyl-○-2,4,5-trichlorophenylthiophosphate (ronnel)○-ethyl-○12.
4,5-trichlorophenylethylthiophosphonate (
Trichlorate)○・0-dimethyl-○-2,5-dichloro-4-bromphenylthiophosphate (bromophos)○・0-dimethyl-○1 (2,5-dichloro-4-iodophenyl)-thiophosphate (iodophenephos) 4 -tert-butyl-2-k.

Ruphenyl-N-methyl-○-methylamide phosphate (crufuomate) 0,0-dimethyl-○1 (3-methyl-4-methylmercapto-phenyl) thiophosphate (fenthion) isopropylamino-○-ethyl-0-(4-methylmercapto- 3-Methylphenyl)-phosphate○・0-diethyl-○-p-(methylsulfinyl)phenyl-thiophosphate (fensulfothion)○1[p-(dimethylsulfamide)phenyl]○・0-dimethylthiophosph Eight (Fuam Fool)
○・0・0′・0′-Tetramethyl 10,0′-thiodi-p-phenylenethiophosphate ○-ethyl-S-phenyl-ethyldithiophosphate 0.0-dimethyl-○-(Q-methylbenzyl-3 monohydroxycrotonyl) phosphate 2-chloro-1-(2,4-dichlorophenyl) vinyl-diethyl phosphate (chlorophenevinphos) 2-chloro-1-(2,4,5-trichlorophenyl) vinyl-dimethyl phosphate ○1 [2-chlororu-11 (2,5-dichlorophenyl)] vinyl-
○・0-Diethylthiophosphate, phenylglyoxylonitrile oximu○・○-diethylthiophosphate (foxime) 0.0-diethyl-○-(3-chloro-4-methyl-2-oxo2-H-1-benzopyran-7- Il)-thiophosphate (coumafuos) 2.
3-p-Dioxanedithiol-S・S-bis(0.0
-diethyldithiophosphate) (dioxathion) 5
-[(6-chloro-2-oxo-3-penzooxazolinyl)methyl]○・0-diethyldithiophosphate (
2-(diethoxyphosphinylimino)-1,3-dithiolane○,0-dimethyl-S-[2-methoxy1,3,4-thiadiazole-5(4H)-oneyl(4)-methyl]dithiophosphate ○・0-dimethyl-S-phthalimidomethyl-dithiophosphate (imidan) ○・0-diethyl-○1 (3,5,6-trichloro-2-pyridyl) thiophosphate ○・0-diethyl-○1 2-pyrazinyl thiophosphate ate (thionazine)○・○-diethyl-○1 (2-isopropyl-4
-Methyl-6-pyrimidyl) thiophosphate (diazinon)○・0-diethyl-○-(2-quinoxalyl)thiophosphate 0.0-dimethyl-S-(4-oxo1.2.3-penzotriazin-3(4H)-yl-methyl)-dithio Phosphate (Azinphosmethyl)○
・0-diethyl-S-(4-oxo1.2.3-penzotriazin-3(cape)-yl-methyl)-dithiophosphate (azinphosethyl)S-[(4.6-diamino-s-triazin-2-yl)methyl] 10,0-dimethyldithiophosphate (menazone) ○,0-dimethyl-○-(3-chloro-4-nitrophenyl) thiophosphate (chlorthion) 0,0-dimethyl-○ (or 1S)-2-(ethylthioethyl) thiophosphate (
Demeton-S-methyl)2-(0,0-dimethyl-phosphoryl-thiomethyl)-5-methoxypyrone-4-3
・4-dichlorobenzyltriphenylphosphonium chloride 0.0-diethyl-S-(2.5-dichlorophenylthiomethyl) dithiophosphate (fenkapton)○・0-diethyl-○-(4-methyl-coumarinyl-
7)-Thiophosphate (potasan) 5-aminobis(dimethylamide)phosphinyl-3-phenyl-1.
2,4 triazole (triamiphos) N-methyl-
5-(0.0-dimethylthiophosphoryl)-3-thiavaleramide (vaamidethione)○・0-diethyl○
1[2-dimethylamino-4-methylpyrimidyl-(6
)]-thiophosphate (dioctyl)○・0-dimethyl-S-(methylcarbamoylmethyl)-thiophosphate (omethoate)○-ethyl-○1(8-quinolinyl)-phenylthiophosphate (oxynotiophos)○ -Methyl-S-methyl-amide thiophosphate (
monitor) 0-methyl-○1 (2,5-dichloro-4
-fromphenyl)-penzothiophosphonate (phosvel)○・0・0・0-tetrapropyldithiophosphate 3-(dimethoxyphosphinyloxy)1N-methyl1N-methoxysis-crotonamide○・0-dimethyl- S-(N-ethylcarbamoylmethyl)-dithiophosphate (ethoethomethyl) 0.0-diethyl-S-(N-isopropylcarbamoylmethyl)-dithiophosphate (propylene).

ethyl)S-N-(1-cyano-1-methylethyl)
Rubamoylmethyldiethylthiophosphate (cyantoate) S-(2-acetamidoethyl) 10.0-
Dimethyl dithiophosphate-tohexamethyl phosphoric acid triamide (Hempa) 0,0-dimethyl-○-(2-chloro-4-nitrophenyl) thiophosphate (dicaptone)○,0-dimethyl-○-p-cyanophenyl thiophosphate (Sia/
Tux) ○-Ethyl 101 p-cyanophenylthiophosphonate ○・0-diethyl-○ 1 2,4-dichlorophenyl thiophosphate (dichlorophenthion) ○-2
・4-dichlorophenyl-○-methylisopropylamidothiophosphate○・0-diethyl-○12,5-dichloro-4-bromphenylthiophosphate (promophos-ethyl)dimethyl-p-(methylthio)phenylphosphate 010-dimethyl-01 p-sulfamidophenyl thiophosphate○-[p-(p-chlorophenyl)azophenyl]○・0-dimethylthiophosphate (azotoate)○-ethyl-S14-chlorophenyl-ethyldithiophosph ate ○-isobutyl-S-
p-Chlorphenylethyl dithiophosphate 0.0
-dimethyl-S-D-chlorophenylthiophosphate ○・0-dimethyl-S(p-chlorophenylthiomethyl)-dithiophosphate ○・0-diethyl-p-chlorophenylmercaptomethyl-dithiophosphate )○・0-diethyl-S(p-chlorophenylthiomethyl)-thiophosphate○・〇-dimethyl-S-(p-chlorophenylthiomethyl)dithiophosphate (fuentate)○・0-diethyl-S-
(carbofluoroethoxyphenylmethyl)-dithiophosphate, ○・0-dimethyl-S-(carboisopropoxyphenylmethyl)-dithiophosphate ○・
0-diethyl-7-hyde.

xy-3,4-tetramethylene-coumarinyl-thiophosphate (cumitoate) 2-methoxy4-H-1.
3,2-benzodioxaphosphorine-2-sulfide 0-diethyl-(5-phenyl-3-isoxazolyl)thiophosphate 2-(diethoxyphosphinylimino)-41-methyl-1,3-dithiolantris- (2-Methyl-1-azaridinyl)-phosphine oxide (metepa) S-(2-chloro-1-phthalimidoethyl)-1○,0-diethyldithiophosphate N-hydroxynaphthalimide diethyl phosphate dimethyl-3.5・6-Trichlor-2-pyridylphosphate 0.0-dimethyl-○-(3.5.6-trichlor-2
-Pyridyl)-thiophosphate S-2-(ethylsulfonyl)ethyldimethylthiolphosphate (dioxydemetone-S-methyl)diethyl-S-2-(ethylsulfinyl)ethyldithiophosphate (oxydisulfoton)bis -○・0-ethylthiophosphoric anhydride (sulfotep) dimethyl-1,3-di (lupomethoxy)
-1-Proben-2-ylphosphate dimethyl-(
2,2,2-trichloro-1-phthyroyloxyethyl) phosphate (butonate) 0,0-dimethyl-○-1(2,2-dichloro-1-methoxypinyl) phosphate bis-(dimethylamide) fluorophosphate (
3,4-dichlorobenzyltriphenylphosphonium chloride dimethyl-N-methoxymethylcarnomoylmethyl-dithiophosphate (fluorocarbum), ○,0-diethyl-○1 (2,2-dichloro-1-chloroethoxy) vinyl) phosphate○・0
-dimethyl-○-(2,2-dichloro-1-chloroethoxyvinyl)phosphate○-ethyl-S-S-diphenyldithiolphosph-to-0-ethyl-S-pendyl-phenyldithiophosphonate 0,0-diethyl-S-
Pendyl-thiophosphate ○・0-dimethyl-S-(
4-Chlorphenylthiomethyl)dithiophosphate (
Methylcarbophenothion)○・○-dimethyl-S1(
Ethylthiomethyl) dithiophosphate diisopropylaminofluorophosphate (mipahox) ○・0-dimethyl-S-(morpholinylcarbamoylmethyl) dithiophosphate (morphothion) bismethylamide phenylphosphate ○ 0-dimethyl-S -(benzenesulfonyl)dithiophosphate○・0-dimethyl-(S and○)-ethylsulfinylethylthiophosphate○・0-diethyl-○-4-nitrophenylphosphate-totriethoxyisopropoxybis( thiophosphinyl) disulfide 2-methoxy 4H-1・3・
2-benzodioxaphosphorine-2-oxide octamethylpyrophosphoramide (sylladan) bis(dimethoxythiophosphinyl sulfide)-phenylmethane N
．． N・N'・N'-Tetramethyldiamide fluorophosphate (Dimefox) ○1 Phenyl-○1 p-Nitrophenyl-methanethiophosphonate (Corep)○-
Methyl-○-(2-chloro-4-tert-butylphenyl)-N-methyldithiophosphate (Naluren).

-ethyl-(214-dichlorophenyl)-phenylthiophosphonate 0,0-diethyl-(4-methylmercapto-3,5-dimethylphenyl)-thiophosphate 4,4-bis-(0,0- dimethylthiophosphoryloxy)-diphenyldisulfide○・0-di(
B-chloroethyl)-0-(3-chloro-4-methyl-coumarinyl-7)-phosphate S-(1-phthalimidoethyl)-○・0-diethyldithiophosphate○・
0-dimethyl-○1(3-chloro-4-diethylsulfamylphenyl)-thiophosphate○-methyl1○1(2-carboisopropoxyphenyl)-amidethiophosphate 5-(○・○-dimethylphosphoryl) -6-
Chlorubicyclo(3.2.0)-heptadiene(1.
5) 0-Methyl 101(21i-bropoxycarbonyl-1-methylvinyl)ethylamide thiophosphate nitrophenols and derivatives 4,6-dinitro-6-methylphenol sodium salt [dinitrocresol] dinitrobutylphenol (2
12.2)-trietanoamine salt 2-cyclohexyl-4,6-dinitrophenol [Jinex] 2-(
1-Methylheptyl)-4,6-dinitrophenylcrotonate [Dinocap] 2-Second-butyl-4,6-dinitrophenyl-3-methyl-butenoate [Binapacryl] 2-Second-butyl-4,6-dinitrophenyl-cyclo Propionate 2-sec-butyl-406-dinito.

Phenyl-isopropyl carbonate [Dinopton]
Others pyrethrin 1 pyrethrin 0 3-allyl-2-methyl-4-oxo-2-sochlorobenten-1-yl chrysanthemamate (allethrin) 6
- Chlorpiveronyl chrysanthemamate parsulin)
2,4-dimethylbenzyl chrysanthemamate (dimethrin) 2,3,4,5-tetrahydrophthalimidomethyl-chrysanthemamate 4-chlorobenzyl-4-chlorophenylsulfide [chlorobenside] 6-methyl-2-oxo- 1,3-dithiolo- [4,51b]
- Quinoxaline [chinomethionate] (1) -3 (2-
furfuryl)-2-methyl-4-oxocyclobent-2-enyl(1)-(cis-trans)chrysanthemum monocarboxylate [fresrin] 2-pivaloyl-indane-1,3-dione [pindong] N'-1 (4
-chloro-2-methylphenyl)-N,N-dimethylformamidine (chlorophenamidine) 4-chlorobenzyl-4-fluorophenyl sulfide (fluorobenside) 5,6-dichloro-1-phenoxical/
Ni-2-trifluoromethyl-penzimidazole (phenozaflor) p-chlorophenyl-p-chlorobenzenesulfonate (Ovex) p-chlorphenyl-benzenesulfonate) (Fuenson) p-k.

p-chlorobenzyl-p-chlorphenyl sulfide (chlorbenside) 2-thio-1
・3-dithiolo(5.6)quinoxaline (thioquinox)prop-2-(4-tert-butylphenoxy)-cyclohexylsulfite (propargyl)formamidine 1-dimethyl-2-(2'-methyl-4'-chlorophenyl) )-formamidine (chlorphenamidine) 1-methyl-2-(2-methyl-4'-chlorphenyl)-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'-chlorophenyl)-formamidine 1-methyl-1-(2
'-Methyl-4'-chloroanilinomethylene) formamidine 2-(2'-methyl-4'-chlorophenyl)
-Formamidine 1-n-Butyl-2-(2'-Methyl-4'-Chlorphenylimino)-Pyrrolidine urea N-2-Methyl-4-Chlorphenyl-N.N'-dimethyl-Thiourea estermate 1-Naphthyl-N-methyl carbamate (Power Rubalil)
2-Butynyl-4-chlorophenylcarbamate 4-dimethylamino-3,5-xylyl-N-methylcarbamate 4-dimethylamino-3-tolyl-N-methylcarbamate (aminocarb) 4-methylthio-3,5-
Xylyl-N-methylcarbamate (methylcarb) 3
・4,5-trimethylphenyl-N-methylcarbamate 2-chlorophenyl-N-methylcarbamate (C
PMC) 5-chloro-6-oxo-2-norpornan-
Carbonitrile-(methylcarbamoyl)-oxime 1-(dimethylcarbamoyl)-5-methyl-3-pyrazolyl-N-N-dimethyl-carbamate (dimethylane) 2,3-dihydro-2,2-dimethyl-7-penzofuranyl-N-methyl Carbamate (carbofuran) 2
-Methyl-2-methylthiopropionaldehyde○
-(methylcarbamoyl)-oxime (aldicarb)
8-quinaldi-N-methylcarbamate and its salts Methyl-2-isopropyl-4-(methylcarbamoyloxy)ruvanylate m-(1-ethylpropyl)phenyl-N-methylcarbamate 3,5-di-tert-butyl-N-methyl Carbamate m-(1-methylbutyl)
Phenyl-N-methylcarbamate 2-isopropylphenyl-N-methylcarbamate 2-Second-butylphenyl-N-methylcarbamate m-tri-N-methylcarbamate 2,3-xylyl-N-methylcarbamate 3-isopropylphenyl N-methylcarbamate 3-tert-butylphenyl-N-methylcarbamate 3-sec-butylphenyl-N-methylcarbamate 3-isopropyl-
5-methylphenyl-N-methylcarbamate (promecarb) 3,5-diisopropylphenyl-N-methylcarbamate 2-chloro-5-isopropylphenyl-N-methylcarbamate (promecarb) 2-chloro-4,5-dimethylphenyl N-methylcarnomate 2-(1.3
-dioxolane-2-yl) phenyl-N-methyl carbamate (dioxacarp) 2-(4,5-dimethyl-
1,3-dioxolan-2-yl) phenyl-N-methylcarbamate 2-(1,3-dioxan-2-yl)
Pheneyl N・N-dimethylcal/Dimate 21 (1・
2-(1,3-dithiolan-2-yl)phenyl-N,N-dimethylcarbamate 2-isopropoxyphenyl-N-methylcarbamate (alprocarb) 2 -(2-propynyloxy)phenyl-N-methylcarbamate 3-(2-propynyloxy)phenyl-N-methyl car/dimate 2-dimethylaminophenyl-N-methyl car/dimate 2-diallylaminophenyl-N-methyl car /ゞmate 4-diallylamino-3
・5-xylyl-N-methylcarbamate (alixycarb) 4-penzothienyl-N-methylcarbamate 2,3-dihydro 2-methyl-7-penzofuranyl-
N-Methylcarnomate 3-Methyl-1-phenylpyrazol-5-yl-N.N-dimethylcarbamate 1
-isopropyl mountain 3-methylpyrazole-5-ilu N
・N-dimethylcarbamate (isolane) 2-dimethylamino-5,6-dimethylpyrimidin-4-yl-N.
N-dimethyl-carbamate 3-methyl-4-dimethylaminomethyleneiminophenyl-N-methylcarbamate 3,4-dimethylphenyl-N-methylcarbamate 2-cyclobentylphenyl-N-methylcarbamate 3-dimethylaminomethylene iminophenyl-N-
Methyl carbamate (formethanate) and its salts 1
-Methylthioethylimino N-Methyl carbamate (methomyl) 2-Methylcarbamoyloxyimino-1
・3-dithiolane 5-methyl-2-methylcarbamoyloxyimino 1,3-oxythiolane 2-(1-methoxy-2-propoxy)phenyl-N-methylcarnomate 2-(1-butyn-3-yloxy)phenyl-N-methylcarnomate /dimate 1-dimethylcarbamyl-
1-Methylthio-○-methylcarbamiyl-formoxime 1-(2'-cyanoethylthio)-0-methylcarbamyl-acetaldoxime 1-methylthio○-car/dimil-acetaldoxime 01(3-2-butylphenyl)- N-phenylthio-N-methylcarbamate 2,5-dimethyl-1,3-dithiolane-2-(0-methylcarbamyl)-aldoxime 3-Chlorobiccyclo [2.2.
1] Hebutane 2-(N-methylcarbamyl-oxyimi/)-bicyclo[2.2.1] Hebutane 3-isopropylphenyl-N-methyl-N-chloroethyl car/dimate 3-isopropylphenyl -N-Methyl-N-methylthiomethyl-rubamate (2,2-dimethyl-4-chloro-2,3-dihydro-7-benzofuranyl) -N-methylcarno-(2,2,4-trimethyl-2)・3-dihydro 7-penzofuranyl)-N
-Methyl carbamate ○ - Naphthyl-N Naphthyl-N
-Acetal-Metal/Metal 3-
Isopropyl-4-methylthiophenyl-N-methylcarbamate 3,5-dimethyl-4-methoxyphenyl-N-methylcarbamate 3-methoxymethoxyphenyl-N-methylcarbamate 3-allyloxyphenyl-N- Methyl carbamate 2-propargyloxymethoxyphenyl-N-methyl-trimethyl/dimate 2
-Allyloxyphenyl-N-methyl-dimethyl-4-methoxycarbonylamino-3-isopropylphenyl-N-methylcar/diamate 3,5-dimethyl-4
-methoxycarbonylaminophenyl-N-methyl-carbamate 2-y-methylthiopropylphenyl-N
-Methyl-carbamate 3-(Q-methoxymethyl-2
-Probenyl)-Phenyl-N-methyl-carbamate 2-Chlor-5 One plan 3 Butyl-phenyl-N-methyl-carbamate 4-(Methyl-propargylamino)-3
・5-xylyl-N-methyl-carbamate 4-(methyl-y-chlorallylamine/)-3.5-xylyl-N
1-methyl-carbamate, 4-(methyl-8-chloroallylamino)-13,5-xylyl-N-methyl-rubamate, 1-(8-ethoxycarbonylethyl)-13-methyl-5-pyrazolyl-N,N-dimethyl-carnomate 3 -Methyl-41 (dimethylamino-methylmercaptomethyleneimy/) phenyl-N-methylcarbamate 1,3-bis(rubamoylthio)121 (N-
N-dimethylamino/)-propane hydrochloride 5,5-dimethylhydroresorcindimethylcal/<〆-to2-[ethyl-propargylamino]-phenyl-N-methylcarbamate 2-[methyl-propargylamino]-phenyl-N-methylcal/ゞmate 2-[dipropargylamino]-phenyl-N-methylcal/diamate 4-[dipropargylamino/]-3tolyl-N-methylcal/
4-[diprobargylamino]-3,5-xylyl-N-methylcarbamate 2-[aryl-isopropylamino]-phenyl-N-methylcarbamate 3
-[allyl-isopropylamino]-pheny-N-methyl car/diamate chlorinated hydrocarbon y-hexachlorocyclohexane [gamexane; lindane; yHCH] 1.2.4.5.6.7.8.8-octachlor-3Q.4. 7.7Q'Tetrahydro4.7
-Methylene indane [chlordane] 1, 4, 5, 6, 7
・8,8-heptachlor 3Q 4,7,70-tetrahydro-4,7-methyleneindan [heptachlor] 1
・2, 3, 4, 10, 10 - Hexachlororu 1, 4, 4
q・5・8・8Q-hexahydro end-1・4-exo 5・8-dimethasonaphthalin [Aldrin] 1・
2,3,4,10,10-hexachlor-6,7-epoxy 1,4,4Q,5,6,7,8,8Q-octahydroexo1,4-endo-5,8-dimethanenaphthalene [ Zieldrin] 1, 2, 3, 4, 10, 10-
Hexachloro-5, 7-epoxy-1, 4, 4Q, 5,
6,7,8,8Q-octahydro-endo-5,8-dimethanenaphthalin [Endrin] The compound of general formula (1) can be used alone or in combination with suitable adhesion substances and/or additives.

Suitable carrier substances and additives may be solid or liquid and include substances customary in formulations, such as natural and recycled substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders and/or fertilizers. be. To apply, use the general formula (
The compounds of 1) can be made into powders, concentrated emulsions, granules, dispersions, sprays, solutions or suspensions in the usual formulations that are common knowledge in the art of application.

Additionally, there are cattle dips and sprayraces, which use aqueous formulations.

The preparations according to the invention can be prepared in a manner known per se with the general formula (1
) and a suitable carrier material, optionally adding an inert dispersant or solvent to the active ingredient, and mixing and/or grinding.

The active ingredient can be used in the following formulation form. Solid preparations: dusts, dusting powders, bulk granules, coated granules, impregnated granules and homogeneous granule solutions'a} Water-dispersible active ingredient concentrates: wettable powders, pastes,
Emulsion 'b} To produce solution-solid formulations (dusts, dusting agents), the active ingredient is mixed with the carrier material.

Suitable support materials include, for example, kaolin, talc, pork ash clay, loess, chalk, limestone, limestone grains, dolomite, lotus acid, precipitated lotus acid, alkali metal silicates, sodium silicate and potassium aluminum silicate (feldspar). and mica), calcium and magnesium sulfate, plastic powder, fertilizers such as ammonium sulfate, ammonium phosphate,
Ammonium nitrate, urea, vegetable flours such as cereal flour, bark flour, wood flour, nut flour, cellulose flour, vegetable extraction residues, activated carbon, etc. can be used alone or in admixture with each other.
Granules are prepared by dissolving the active ingredient represented by general formula (1) in an organic solvent, applying the resulting solution to granular materials such as attapulgite, SiO2, calcium particles, bentonite, etc., and then evaporating the solvent. It is extremely easy to prepare.

Polymerized grains are also produced by mixing the active ingredient represented by the general formula (1) with a compound that can be polymerized (urea/formaldehyde, dicyandiamide no formaldehyde, melamine/formaldehyde, etc.), and then heating it in a mild manner that does not affect the active ingredient. It is prepared by polymerization and granulation during gel formation in the process. Finished porous polymeric granules (urea/formaldehyde, polyacrylonitrile,
It is more advantageous to impregnate the active ingredient (such as a polyester) with the active ingredient, for example in the form of its solution (in a low-boiling solvent), and to remove the solvent. Finely divided polymer granules of this type having a bulk density of 300 to 600 m/s are also prepared using an atomizer. Spraying is carried out from airplanes over large cultivated areas of useful plants. Granules can also be obtained by solidifying the carrier material and the active ingredient and additives and subsequently comminuting the product.

Additives may be added to the above mixtures to stabilize the active substance and/or to improve the adhesion of the active ingredient to plants or plant parts (adhesives and flocculants) and/or to improve wetting properties (wetting agents). and nonionic, anionic and cationic surface active substances that ensure dispersibility (dispersants) may be added. Examples of suitable adhesives are olein/chalk mixtures, Cell. oxyethyl glycol ethers of monoalkyl and dialkylphenols having 5 to 15 ethylene oxide groups per molecule and 8 to 9 carbon atoms in the alkyl group, lignin sulfonic acid, Its alkali metal and alkali metal salts, polyethylene glycol ether (Carpowax), 5 to 2 per molecule
hard ethylene oxide group, and fatty alcohol moiety 8
Fatty alcohol polyethylene glycol ethers with ~18 carbon atoms, condensation products of ethylene oxide/propylene oxide, polyvinylpyrrolidone, polyvinyl alcohol, condensation products of urea and formaldehyde and also latex products. Water-dispersible active ingredient concentrates, ie wettable powders, bases and concentrated emulsions, are preparations that can be diluted with water to the desired concentration.

The formulation consists of the active ingredient, a carrier substance, optionally additives for stabilizing the active ingredient, surfactants and antifoaming agents and, if necessary, a solvent. Wettable powders and pastes are prepared by mixing the active ingredient with the dispersant and powder carrier material in suitable equipment until homogeneous and grinding.

For example, those described for solid preparations are applicable as the adhesion substances. It is often advantageous to use mixtures of different support materials. Examples of dispersants include 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 of lignin sulfonic acid, ammonium salts and alkali Salt metal salts, as well as alkylaryl sulfonates, alkali metal salts and alkali metal salts of dibutylnaphthalene sulfonic acid, fatty alcohol sulfates, sulfated hexadecanol, sulfated heptadecanol, sulfated octadecanol salts and fatty alcohol glycols. Salts of ether, sodium salts of oleylethionate, sodium salts of oleylmethyltauride, ditertiary acetylene glycol, dialkyldilauryl ammonium chloride and alkali metal salts and alkali metal salts of fatty acids. Suitable antifoaming agents include, for example, silicones.

- the active ingredient is mixed with the additives mentioned above, ground and aged to a solids content of 0.02 in the case of wettable powders;
In the case of paste, the particle size should not exceed 0.03 Yanagi.

To prepare concentrated emulsions and pastes, dispersants, organic solvents and water as described above are used. Suitable solvents are, for example, alcohols, benzene, xylene, toluene, dimethyl sulfoxide and mineral oils having a boiling point range of 120 DEG to 350 DEG C. The solvent should be largely odorless and inert towards the active ingredient.
Furthermore, the formulations according to the invention can be used in the form of solutions.

For use as a solution, the active ingredient of general formula (1) is dissolved in a suitable organic solvent, solvent mixture or water or a mixture of an organic solvent and water. Organic solvents include aliphatic and aromatic hydrocarbons, their chlorinated derivatives, alkylnaphthalenes,
Key oils can be used alone or in combination. The content of active ingredient in the above drugs is from 0.1 to 95%, in which case concentrations up to 99.5% or even pure active ingredient may be used when applied from aircraft or other suitable means of application. You can also do it. Next, the formulation format of the compound of formula (1) will be illustrated.

"Part" represents "part by weight." Dust: The following materials are used to prepare [a]5% dust and [b12% dust.

[a- Active ingredient 5 parts Talc 95 parts {b' Active ingredient 2 parts Highly dispersed silicic acid
1 part talc
97 parts of active ingredient are mixed with carrier material and ground.

Granules: The following substances are used to prepare 5% granules: Active ingredients 5 parts epichlorohydrin 0.25 parts cetyl polyglycol ether 0.25 parts polyethylene glycol 3.5 parts Guo kaolin (granules) 91 parts of the active ingredient are mixed with epichlorohydrin and dissolved in 6 parts of acetone;
Then polyethylene glycol and cetyl polyglycol ether are added.

The solution thus obtained is sprayed onto the kaolin and the acetone is then evaporated in vacuo. Hydrate [a-40%, 'b- and [c'25% and {d'10
% The following ingredients are used to prepare the hydrating agent: [a} Active ingredients 4 parts sodium lignin sulfonate 5 parts sodium dibutylnaphthalene sulfonate 1 part silicic acid
54 copies.

{b} Active ingredients: 25 parts Calcium lignin sulfonate 4.5 parts Champagne chalk/hydroxyethyl cellulose mixture (
1:1) 1. $ parts Sodium dibutylnaphthalene sulfonate 1.5 parts Silicic acid 19.5 parts Champagne chalk 19.5 parts Kaolin
28.1 part.

[d Active ingredient: 25 parts isooctylphenoxy polyoxyethylene ethanol 2.5 parts Champagne chalk nooxyethyl cellulose mixture (1:1)
1.7 parts sodium aluminum silicate
&$ Department 16.5
Kaolin 46 parts. ~ side
Active Ingredients Hattori A mixture of sodium salts of sulfated saturated fatty alcohols
3 parts naphthalene sulfonic acid/formaldehyde condensate 5 parts Orin 82 parts.

The active ingredient is intimately mixed with the additives in a suitable mixer;
The mixture is then milled with suitable mills and rollers. Sailor zero is thus obtained, which can be diluted with water to produce suspensions of any desired concentration. Emulsifiable concentrate 'allo% and 'b} The following substances are used to prepare the 25% emulsifiable concentrate: 'a} Active ingredient
Meto epoxidized vegetable oil
3.4 parts composite emulsifier consisting of fatty alcohol polyglycol ether and alkylaryl sulfonic acid calcium salt 13.4 parts dimethylformfamide 4 Ikarito xylene
43.2 parts.

{b' Active ingredient 25
1 part epoxidized vegetable oil 2.5 parts alkylaryl sulfonate/fatty alcohol polyglycol ether mixture 1 part dimethylformamide
5 parts xylene 57
．． Part 5.

Emulsions of any desired concentration can be prepared from the concentrates by dilution with water. The following ingredients are used to formulate the Akebono 5% spray.

Active Ingredients 5 parts Pichlorohydrin 1 part Benzine (boiling point range 16
0-19000) Spotted area.

Next, the present invention will be explained in detail based on examples. Example 1 (
Production example) Anhydrous potassium carbonate powder in a solution of 4-hydroxy diphenyl ether 19.8 g in acetone 80 g.
Add 3-methyl-4-bromo-2 while stirring.
-Butenoic acid ethyl ester (20.8 g of a mixture of 80% trans-compound and 20% cis-compound) was added within 1 hour at the boiling temperature of the mixture.

After the bromide was added, heating was continued for 8 hours at reflux temperature. The reaction mixture is vacuumed to remove the precipitate from the acetone solution, the residue is washed with acetone, and the acetone is removed in vacuo. The aliquot was taken up in 20 g of a 1:5 mixture of ether and hexane and the solution was washed first four times with 50 g of ice-cold 5% potassium hydroxide solution and then four times with water. The organic phase is dried over sodium sulfate and the solvent and easily volatile components are completely removed in vacuo to give pure 4-[4-(phenoxy)-phenoxy]-13-methyl-12-butenoic acid ethyl ester. (cis/trans) was obtained. n rule:
1.5598 Example 2 (Production Example) Add ethyl diisopropylamine 15.6 # to a solution of 1,2-dimethoxyethane 100 and 4-amino diphenyl ether 18.6 and While doing so 1・2-
A solution of 19.3 g of 3-methyl...4-bromo-2-trans-butenoic acid methyl ester in 80 g of dimethoxyethane was added within 8 hours at room temperature.

The fly worship was continued for 2 hours at room temperature. Ethyl diisopropylammonium bromide precipitated from the reaction mixture was removed in an oven,
Purify with ether and remove the solvent from the furnace solution in vacuo.
The resulting crude product was further chromatographed on silica gel (solvent: enal/hexazole 1:2) to give n color o=
1. 91 spots of pure 4-[4-(phenoxy)-anilino]-13-methyl-2-trans-butenoic acid methyl ester were obtained. Example 3 A solution of 6 parts of 4-[4-(fe/xy)-anilino]-3-methyl-2-transbutesoic acid methyl ester in 5 parts of formic anhydride was mixed with a mixture of 10 parts of acetic anhydride and 92 parts of formic anhydride. (The mixture was heated to 45 qo for 1 hour before forming the mixed acetic monoformic anhydride.)
Added dropwise within minutes.

The reaction mixture was then held at 0-500 for 6 hours and then at 3000 for 2 hours. The reaction mixture was treated with 50 ml of water while gently cooling with ice and heated at 10-lyC for 1 hour. The reaction mixture was extracted repeatedly with ether and the combined ethereal phases were washed first with saturated sodium bicarbonate solution and then with water until neutral. After drying the ether solution over sodium sulfate and removing the solvent completely under vacuum, the remaining 4-[4-(phenoxy)-1N-formylanilino]-3-methyl-2-trans-butenoic acid methyl ester was further purified by chromatography on silica gel. Melting point: 93-9500. Example 4 Approximately 50% sodium hydride in mineral oil was washed repeatedly with hexane and 80% of anhydrous tetrahydrofuran in a sulfated flask.
I definitely put it in.

While stirring, add 16.6% of diethylphosphonoacetic acid diethylamide in 20% of anhydrous tetrahydrofuran.
It was added dropwise within about 45 minutes at .degree. Heat the mixture to room temperature,
Continue worshiping the lights for 30 minutes. Cool again to 5°C and add 40% of anhydrous tetrahydrofuraso while stirring.
benzyl) phenoxy]-propan-2-one 14.4
The original solution was added dropwise within 1 hour. After 2 hours, the reaction mixture was heated to 30°C and held at this temperature for 2 hours.

The reaction mixture was worked up by distilling off most of the tetrahydrofuran in vacuo, partitioning the residue between water and diethyl ether, and washing the aqueous phase repeatedly with ether. The combined ethereal phases were dried over sodium sulfate and the solvent was stripped off. The residue was further purified by chromatography on silica gel (eluting agent: methyl acetate/ethyl ether/hexane 1:4:2) to give pure 41 [41 (benzyl)] with n color o = 1.5596. -phenoxy]-3-methyl-2cis/trans-butenoic acid diethylamide was obtained. In a similar manner, 4-[4-(
Penzyl)-phenoxy]-3-methyl-2-trans-butenoic acid isopropylester (n color o = 1.551
2) and 4-[4-(benzyl)-phenoxy]-3-
Methyl-2-cis-butenoic acid isopropylester (n
color.

= 1.5451) was obtained. 1- used as starting material
[4-(Benzyl)-phenoxy]-propan-2-one was produced as follows.

mercury oxide 22.3 times, trichloroacetic acid 0.8 times, trifluoride sherajethyl etherate 8 times [and anhydrous methanol 2 times]
A pre-prepared mixture of 0.0% was added all at once to a solution of 11.1% of 4-benzylpropargyloxybenzene (n = 1.5807) in 400% of absolute methanol, cooled to -5°C. did.

After about 1 minute, the external cooling is turned off and the temperature of the reaction mixture (
The exothermic reaction) gradually increased to a maximum of 45°C. External cooling is increased again at this temperature and the reaction mixture is heated to about 20-25oC.
It was held at C for an additional 3 hours. During the reaction, the color of the mixture changed from light blue to light gray. The resulting jetyl ketal was isolated by pouring the flask contents, cooled to about 0 DEG C., onto a mixture of 125 g of sodium carbonate solution and 500 g of ice. After about 10 minutes of rope worship, the entire mixture was washed with 7% phosphoric acid.
Acidified at 50°C and treated with 700°Z of diethyl ether. The batch was passed through a bed of diatomizers, the ether layer was separated, and the aqueous phase was extracted three times with diethyl ether. The combined fable phase was dissolved in 5% ice-cold potassium hydroxide solution 2
Wash with 300' of saturated sodium chloride solution and 300' of saturated sodium chloride solution.
Washed 3 times with The clear hue was dried over sodium sulfate,
The solvent was completely removed. The resulting 1-[4-(benzyl)
Phenoxy]-propane-2-one dimethyl ketal is immediately dissolved in a mixture of 600 parts acetone, 100 parts water and 35 parts IN hydrochloric acid and hydrolyzed to the ketone by standing at room temperature for 5 hours. The ketone was isolated by pouring the reaction mixture into 600 ml of saturated sodium chloride solution and washing the aqueous phase three times with diethyl ether. The combined organic phases were washed three times with saturated sodium chloride solution, dried over sodium sulfate and the solvent was completely removed in vacuo. The crude ketone, once solidified in crystalline form, is recrystallized from isoprobanol to obtain pure 1-[4-(benzyl)-phenoxy]-propane- with a melting point of 51-5〆○.
Got 2-on. In exactly the same way, 4-propargyloxydiphenyl ether (n color 0 = 1.5825)
, 4-propargyloxybenzophenone (melting point 72~
7300) and 2-[4-(phenoxy)-phenoxy]-3-butyne (melting point 53-54 qo), the following ketones were prepared as intermediates: 1-[4-
(Phenoxy)-Phenoxy]-Propane-2-one (
melting point 47-48°C), 1-[4-(benzoyl)-phenoxy]-propan-2-one (melting point 51-520) and 2-[4-(phenoxy)-phenoxy]-butane-
3-one (melting point 36-370).

The following compounds were prepared in a manner similar to that described in Examples 1-4.

Example 5 ■Local effect on larvae of D$dercus fasciatus D$dercus fasciatus larva 10
The animals were treated topically with a solution of the active ingredient in acetone 8-10 days before they molted and entered the adult stage.

Larvae were kept at 28 oo and 80-90% relative humidity.
The larvae were fed a diet made from pre-warmed cotton seeds. After about 10 days, ie, as soon as the untreated larvae had molted, the number of normal adults was determined. (B) Disdercus.

Contact action on Phasiatius A certain amount of an acetonic 0.1% active ingredient solution (corresponding to 9 parts of 10 active ingredient per serving) was pipetted into an aluminum dish and uniformly dispersed.

After the acetone had evaporated, 10 fifth stage larvae of Deisdercus huasiatous were placed in the dish with food and warmed cotton. The next blood was covered with a perforated lid.
After about 10 days, ie, as soon as the control larvae had completely molted and reached the adult stage, the test insects were examined and the number of normal adults was counted. Compounds according to Examples 1 to 4 were tested in Tests A and B above.
showed good effects.

Table 1 below shows the evaluation results of Test B for some compounds.

The evaluation was expressed as a number from 1 to 5, with 5 meaning no normal adult worms (maximum effect) and 1 meaning no effect on normal development (no effect). death,
4-2 means an intermediate effect. Example 6 Dermestes lardarius (Dennestes larda)
10 fresh ants of Dermestes lardarius were treated topically with a solution of the active ingredient in acetone.

The ants were kept at a relative humidity of 80-90% for two nights. about 10
Days later, ie, as soon as the controls left their cocoons as adults, the test insects were examined and the number of normal adults was counted. In the said tests the compounds according to Examples 1 to 4 showed a good effect.
Example 7 Contact action against larvae of Aedesaegypti Approximately 20 2-day-old larvae of Aedesaegypti were placed in a beaker containing a solution of the active ingredient (concentration 5 skin).

The beaker was covered with a perforated lid. Once the control insects had fully molted to the adult stage, the insects were examined and the percentage of normal adults relative to the number of normal adults present in the controls was calculated. The compounds according to Examples 1 to 4 showed high potency in the previous test.

Table 1 below shows the evaluation results of the above tests for some compounds.

Evaluation was performed using the scale used in the example. Example 8 Tenebriomol
A certain amount of the acetone solution of the active ingredient (equivalent to 9 parts of 10 parts of the active ingredient) was pipetted into an aluminum dish and uniformly dispersed.

After evaporating the acetone, 10 freshly molted piths were placed on the treated surface.

The dish was covered with a perforated lid. After the controls left their cocoons as adults, the test insects were examined and the number of normal adults was counted.

In the said tests the compounds according to Examples 1 to 4 showed a good effect.

Table 1 below shows the evaluation results of the above tests for some compounds.

Evaluation was performed using the scale used for the Example plaques. Example 9 Ephestia cuuniella
50 grams of wheat flour were mixed with a predetermined amount of 50% powder of active ingredient to give a concentration of 0.1, 0.05 or 0.01% and placed in two beakers.

- Per peaker (25 evenings of flour), Ephesteia
I added 10 Kuhnella larvae. After 8 weeks, the number of moths that had emerged was counted.

The evaluation results of the above test are shown in Table 1 below.

The evaluation was expressed as a number from 1 to 9, where 1 indicates an active ingredient concentration of 0.
1% means that moths occur, and 3, 5, and 9 mean that no moths occur at concentrations of 0.1%, 0.05%, and 0.01%, respectively. Example 10 Tribolimcastane
um) Fifty grams of wheat flour were mixed with the specified amount of active ingredient to the same concentration as described in Example 9 and placed in two beakers.

- Beaker (25 beetles of Cochinopsis were added per 25 grams of flour and separated after 3 days. The number of beetles that hatched from the eggs laid in the flour was examined after 8 weeks. The evaluation results of the above test are described below. Shown in Table 1.

Evaluation was performed using the scale used in Example 9 (however, "moth" should be read as "beetle"). Example 11 Aonidiellea
Action against tii) Potato tubers infested with red mealybugs were soaked in an acetone solution or emulsion containing 0.05% of the active ingredient.

Insect development and spawning were investigated. The evaluation results of the above test are shown in Table 1 below.

Evaluation was performed on the following scale of 1 to 9: 9 = Mortality rate 75-100% 7 = Mortality rate 51-74% 5 = Mortality rate 25-50% 3 = Mortality rate 1-25% 1 = 100% normal adult worms (no effect) Example 12
Effect on 5 to 10 skins of rice in a cultivation container was sprayed with a solution of the active ingredient in acetone (water:acetone = 1:1) (0.05% concentration).

After the spray solution had dried, about 20 L2-stage larvae of P. elegans were placed in the container. The evaluation results of the above test using the evaluation scale described in Example 11 are shown in Table 1 below.

Example 13 Lepteinotarsa decem. Action against Lineata rsadecemlineata A predetermined amount of a 1% acetone solution of the active ingredient was added to a 1:1 mixture of water and acetone to give an active ingredient concentration of 0.025%.

Potato leaves were soaked in this acetone-water solution and then hung to dry. Ten Leptinotarsa decemlineata larvae of the fourth stage were placed in each of two polyvinyl chloride dishes containing the treated potato leaves on sterile soil. The evaluation results of the above test using the evaluation scale described in Example 11 are shown in Table 1 below.

Example 14 Spodoptera litoralis (Spodoptera IM
1% acetone solution of the active ingredient was added to a 1:1 mixture of water and acetone in an amount such that a solution with an active ingredient concentration of 0.075% was obtained.

Lettuce leaves were soaked in this acetone-water solution and then hung to dry. In each of the two platters containing the above treated lettuce leaves on a circular filter, a third pear;
Then, 10 Spodoptera littoralis larvae at the fourth stage were added. Immediately before atomization, sterile sawdust was added under the paper filter. Next, the ants were removed from the mirror powder and placed in a cage to observe their growth. The evaluation results of the above test using the evaluation scale described in Example 11 are shown in Table 1.

The shore group bonito Rice ship ship fence Guidance The shore mallet Shigeru the gunwale ship job

Claims (1)

[Claims] 1. General formula: ▲ Numerical formula, chemical formula, table, etc. together with appropriate supporting substances and/or additives ▼ [In the formula, R_1 is a cyclohexyl group, a cyclohexyloxy group, or a group of the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, Y is -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ , - CH_2-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ -CH_2O-, -OCH_2- , -NH-, ▲ Formula,
There are chemical formulas, tables, etc. ▼ (R_5 is C_1-C_3-
represents an alkyl group, formyl group, or acetyl group) or a direct bond, R_7 is hydrogen, halogen, C_1-
C_5-alkoxy group or C_1-C_5-alkyl group), Z is -O-, -NH-, ▲ formula,
There are chemical formulas, tables, etc. ▼ , or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (R_6 represents hydrogen or C_1-C_3-alkyl group), and this ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ The part is phenyl It is bonded to the nucleus, R_2 represents hydrogen or C_1-C_3-alkyl group, R_3 is -COOH, (C_1-C_5-
alkoxy)carbonyl group, (C_3-C_5-alkenyloxy)carbonyl group, (C_3-C_5-alkynyloxy)carbonyl group, cyclohexyloxycarbonyl group, phenoxycarbonyl group, (C_3-C_5
-halogenalkenyloxy)carbonyl group, cyano group, or C_1-C_5-alkyl-, C_3-C_5-
Alkenyl- or C_3-C_5-alkynyl represents a mono- or di-substituted carbamoyl group, in which the substituents of the carbamoyl group together with the nitrogen atom to which it is attached optionally also carry an oxygen atom, a sulfur atom or another nitrogen atom. may form a 5- or 6-membered saturated heterocyclic ring, R_4 represents hydrogen, methyl group or ethyl group, and R_8 represents hydrogen, halogen, methyl group or ethyl group]. A pest control agent characterized by containing at least one compound.