CN1059514A - Imidate insecticides - Google Patents
Imidate insecticides Download PDFInfo
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- CN1059514A CN1059514A CN91108681A CN91108681A CN1059514A CN 1059514 A CN1059514 A CN 1059514A CN 91108681 A CN91108681 A CN 91108681A CN 91108681 A CN91108681 A CN 91108681A CN 1059514 A CN1059514 A CN 1059514A
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- compound
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/04—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers
- C07C257/06—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers having carbon atoms of imino-carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms, or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The sterilant that general formula is following, R in the formula
1, R
2, R
3For hydrogen, halogen, haloalkane, alkyl halide oxygen (sulphur) base but can not be hydrogen; R
1And R
2Can also merge into (halogen) alkylenedioxy group; R
4Be (halogen) alkyl, alkenyl, cyclopropyl; R
5For:
R
6Be phenyl, benzyl, alkenyl, alkynyl; R
7, R
11Be hydrogen, halogen; R
8, R
10Be halogen; R
9Be methyl, methylthio group, methoxy (sulphur) methyl, methylol, cyano methyl, alkenyl, alkynyl, propargyl amino.
Description
The present invention relates to have a series of new pesticides of following general formula:
In the formula:
R
1Be hydrogen, halogen, C
1-C
4Alkoxyl group, C
1-C
4Haloalkyl, C
1-C
4Halogenated alkoxy or C
1-C
4Halogenated alkylthio;
R
2Be hydrogen, halogen, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, C
1-C
4Haloalkyl, C
1-C
4Halogenated alkoxy or C
1-C
4Halogenated alkylthio;
R
3Be hydrogen, halogen or C
1-C
4Haloalkyl; Or
R
1And R
2Merge into C
1-C
4Alkylene oxide group or halo C
1-C
3Alkylene oxide group;
Regulation R
1, R
2, and R
3Can not be hydrogen;
R
4Be methyl, ethyl, n-propyl, C
3-C
7Branched alkyl, C
1-C
6Haloalkyl, C
2-C
6Alkenyl; Or cyclopropyl, preferably contain 1-4 methyl or 1-2 halogenated cyclopropyl
R
5For
R
6Be phenyl, benzyl, C
3-C
4Alkenyl or C
3Alkynyl;
R
7, R
8, R
10, and R
11The halogen of respectively doing for oneself; With
R
9Be methyl, methoxymethyl, methylthio group, methylthiomethyl, methylol, cyano methyl, benzyl, C
3-C
4Alkenyl, C
3Alkynyl or proyl amino.
The present invention also comprises parasiticidal preparation, promptly contains the above compound of regulation of insecticidal effective dose, with the preparation that is fit to make as the diluent or carrier that sterilant is used.The present invention also comprises the method for preventing and treating insect, promptly uses the compound of the present invention of insecticidal effective dose or the preparation place in the needs control.
Terminology used here: " halogen " comprises fluorine, chlorine, bromine and iodine, general preferred fluorine or chlorine; " alkylenedioxy group " refers to-O-alkylidene group-O-linking group, and alkylidene group wherein (can be straight chain or branched) contains 1 to 4 carbon atom, and this class group comprises methylene radical dioxy base (O-CH
2-O-), ethylene dioxy base (O-CH
2-CH
2-O-), one or dihalo methylene radical dioxy base (be in the methylene radical dioxy base one or two hydrogen replaced) and isopropylidene dioxy base (O-C(CH by halogen
3)
2-O-); Term " propargyl amino " refers to-NHCH
2C ≡ CH base; " haloalkyl, halogenated alkoxy, halogenated alkylthio or halo alkylenedioxy group " comprises this class group that one or more halogens identical or inequality replace.For these halo groups, preferred halogen is fluorine, chlorine and bromine, and fluorine is most preferred.The example of this class group comprises difluoromethyl, trifluoromethyl, difluoro-methoxy, trifluoromethoxy, difluoro bromine methoxyl group, difluoro chlorine methoxyl group, difluoro methylene dioxy base and the above-mentioned halogenated analogue that contains more than a carbon atom.
" alkyl ", " alkoxyl group " and similar group comprise straight chain and the branched group that contains the regulation carbonatoms.
Term " alkenyl " comprises two kinds of groups of straight chain and branched single ethylene linkage.
R
1, R
2And R
3Preferred examples is hydrogen, halogen, oxyethyl group, difluoromethyl, trifluoromethyl, difluoro-methoxy, trifluoromethoxy, 2,2,2-trifluoro ethoxy, 1,1,2-three fluoro-2-chloroethoxy or R
1And R
2Merge into methylene radical dioxy base, difluoro methylene dioxy base.
Preferred halogenated alkylthio is a trifluoromethylthio.
Preferred R
4Be ethyl, sec.-propyl, the tertiary butyl, pseudoallyl, dichloromethyl and cyclopropyl.
Preferred R
5Comprise 2,3,5,6-tetrafluoro-4-propargyl phenyl; 2,3,5,6-tetrafluoro-4-allyl phenyl; 2,3,5,6-tetrafluoro-4-methoxymethyl phenyl; 3,5-two fluoro-4-propargyl phenyl; The 4-phenyl; With the 4-benzyl phenyl.
Compound of the present invention can be following two kinds of methods or a kind of method preparation wherein.
Method (A)
Chemical compound lot of the present invention can react by following formula with alkali metal alcoholates with imino-halide (preferred chlorine) and prepare:
In the formula, M is a basic metal, preferred sodium or potassium; Hal is halogen, particularly chlorine or bromine.
This is reflected at approximately and carries out in-70 ℃ to+65 ℃ scopes, is preferably room temperature, and its reaction times is 5 minutes to 24 hours.Be reflected in the solvent and carry out, solvent is, for example, and aromatic hydrocarbon such as benzene, toluene or dimethylbenzene or ether such as ether, diisopropyl ether, isoamyl ether, dibutyl ether, furans, 1,2-glycol dimethyl ether or tetrahydrofuran (THF) (preferred tetrahydrofuran (THF)).In some cases, skilled synthetic technology personnel are very clear, add alkali metal alkoxide solution in imino-halide solution or to use excessive pure salt pair reaction be favourable.The product that generates can obtain with the technology of routine.
Alkoxide is with corresponding alcohol, as 2,3,5,6-tetrafluoro-4-methoxymethyl phenylcarbinol with contain alkali-metal alkali, reaction in solvent is produced as alkalimetal hydride (for example, potassium hydride KH, or preferred sodium hydride).Here used solvent is a used the sort of solvent in alkali metal alcoholates and the imino-halide reaction.Usually this is reflected under reflux temperature and the protection of inert gas and carries out, and the reaction times is within 2 hours scope.
Alcohol in the reaction, if when not having supply of commodities, can be according to the currently known methods preparation of putting down in writing in the following data: United States Patent (USP) 4,370,346 and 4,594,355; UK Patent Application 2,122,616 and 2,207,917; European patent application 196,156 and 271,240; With J.Sci.Food ﹠amp; Agriculture 18,167(1967).
Imino-halide can be from corresponding amine or acid amides preparation.But amine usually market is bought, also available known method, and for example method of record prepares in the work such as Harrison " (Compendium of Organic Synthetic Methodes " (Wiley-Interscience, New York, 1971).
If acid amides does not have the source of goods, can react with amine and carboxylic acid halides and prepare.
The temperature range of this reaction is about-40 to+80 ℃, and the solvent that is fit to comprises: hydro carbons such as toluene and halogenated hydrocarbon such as methylene dichloride, chloroform, tetracol phenixin, ethylene dichloride, tetrachloroethane and analogue thereof, preferred methylene dichloride.Be reflected under the alkali existence and carry out, preferably tertiary amine.The alkali that is fit to comprises triethylamine, quinoline, N, and accelerine, N, N-Diethyl Aniline and pyridine, triethylamine are preferred alkali.Acid amides can obtain and purifying with method commonly used.
Imino-halide can prepare from acid amides, reacts in the used solvent of preparation acid amides (preferred methylene dichloride) with it and halogenating agent such as phosphorus pentachloride or phosgene, and also available phosphorus oxychloride is made solvent.Be reflected under the protection of inert gas and carry out, the reaction times is the longest 24 hours, more preferably 1 to 24 hour.Temperature of reaction is about 0 ℃ to 110 ℃.Before imino-choride entered the final step reaction, the material of the pure reactant salt during all can react with final step all should be got rid of as phosphorus oxychloride or hydrogenchloride.Usually finish this removal work with evaporation or distillation.
Method (B)
This is the method from the replacement method (A) of the alcohol of highly basic sensitivity being produced The compounds of this invention, highly basic (for example alkalimetal hydride) used during the preparation alkoxide has bad influence (as decomposing), 2,3 to this alcohol, 5,6-tetrafluoro propargyl benzylalcohol is an example to the responsive alcohol of alkali.
Such compound can prepare with alcohol and imino-choride direct reaction in the presence of the 4-two elementary alkyl amido pyridine (preferred 4-dimethylaminopyridine) of tertiary amine and reaction promotion amount.
The tertiary amine that can be used in the method (B) comprises trialkylamine, as Trimethylamine, triethylamine, tri-n-butyl amine and analogue thereof, comprises the tertiary amine with mixed alkyl, N, N-dialkyl aniline, N for example, the pyridine of accelerine, pyridine and various replacements.
From considering that economically preferred tertiary amine is triethylamine, N, accelerine and pyridine.Tertiary amine also can be promotor 4-two rudimentary aminopyridine, but its consumption will add the needed amount of promotion reaction.
The usage quantity of preferred tertiary amine is the stoichiometric quantity corresponding to used alcohol, but also can use excessive.The consumption of promotor 4-two elementary alkyl amido pyridine is every normal pure with 0.05 to 1 equivalent, and more every normal alcohol is used 0.05 to 0.15 equivalent approximately, preferably uses 0.1 equivalent approximately.
This reaction is more preferably carried out in about 10-50 ℃ scope better.Lower temperature can adopt, but speed of response is very slow.Reaction is carried out in inert solvent, and inert solvent has aromatic hydrocarbon (as benzene, toluene or dimethylbenzene), chloride solvent (as methylene dichloride, ethylene dichloride or chlorinated benzene) or ether (as ether, dioxane or tetrahydrofuran (THF)).
Though this method is particularly suitable for producing required compound from alkali-sensitive alcohol, it also can be used as method in common and produces compound of the present invention from other alcohol.
It below is an example producing The compounds of this invention.
N-(3-chloro-4-Trifluoromethoxyphen-l)-
O-(2,3,5,6-tetrafluoro-4-propargyl-
Benzyl) preparation of isopropylformic acid imines ester
In a reaction flask that maintains under room temperature and the nitrogen protection; place 500mg(1.66mmol) N-(3-chloro-4-Trifluoromethoxyphen-l) the isobutyl-imino-choride; 0.16g triethylamine, 50mg4-dimethyl aminopyridine and 361mg(1.66mmol) 2; 3; 5,6-tetrafluoro-4-propargyl benzylalcohol.Reaction mixture was at room temperature stirred 72 hours, and monitor reaction with gas chromatograph.Add the 100ml hexane then.Reaction mixture washs with 5% ethyl acetate/hexane by filtered through silica gel, merging filtrate, boils off hexane under 30 ℃, obtains the low-melting solid of 380mg being lower than.Product is through gas spectrum and nmr analysis, contains 62.5-66% and wishes the product that obtains.
Representative compounds of the present invention is described as follows with table I and II.
Insecticidal action is estimated
Insecticidal activity with listed compound in following determination of test method table I and the table II.The LC-50 value that is listed in the table III is according to the result of test, calculates according to dosage mortality curve.
Housefly
With the compound acetone diluted of test, pipette the part soup in aluminum dish bottom with transfer pipet, for guarantee medicament equably spread contain the acetone soln of 0.01% peanut oil in every ware adding 1ml in the aluminum dish bottom.At solvent all after the evaporation, have in the garden shape paperboard cage of the female housefly that makes 25 1-2 days in aluminum dish is placed on.The bottom of cage hides with glassine paper, and top cover is with tissue web, and it is edible for housefly all to place the saturated cotton mass of syrup in every cage.Note mortality ratio after 48 hours.The dose of test compound progressively descends from per 25 female fly 100ug.The LC-50 value is listed in table III " HF " item down, and its unit is a ug/25 female fly.
Beans winged euonymus aphid
The nasturtium of the about 5cm of plant height is transplanted in the cuvette of sand clay, and inoculation 25-50 head mixes the beans winged euonymus aphid of worm order, after 24 hours, be sprayed onto loss (soup runs off from plant) with 50% aqueous acetone solution of test compound till.Plant behind the spray medicine is placed in the greenhouse, writes down mortality ratio after 48 hours.The concentration of test compound progressively descends from 0.05%.The LC-50 value is listed in table III " BA " item down, represents with the percentage of test compound in spraying liquid.
Cigarette beetle
(a) test of tagging: test compound is dissolved in 50% aqueous acetone solution.Cotton cotyledon is placed on test soaks 2-3 second in the soup, be placed on the wire cloth then and dry.Leaf after will drying is placed in the culture dish of built-in wet filter paper, inoculates 52 and makes Spodoptera litura larvae.Culture dish is placed in the high humidity case 5 days, the record larval mortality.The concentration of test compound progressively descends from 0.05%.The LD-50 value is listed in table III " TBW-C " item down, and its unit is the percentage ratio of test compound in soup.
(b) ovum: will make the tissue sheets of ovum be placed in the acetone soln of test compound on the 2nd with prodenia litura and be placed in the culture dish after the dipping, put a larvae feeds in the ware.The ovum of handling is remained under 78 °F, all hatch at the ovum of control group, larva gets food on feed after, the record mortality ratio.The concentration of test compound progressively descends from 0.05%.The LC-50 value is listed in table III " TBW-E " item down, represents with the percentage ratio of test compound in soup.
Cabbage looper:
Test compound is dissolved in 50% the aqueous acetone solution.With about 1 * 1.5 inch a kind of pumpkin (hyzini squash(calabacita abobrinha)) cotyledon is placed on and soaks in the testing liquid 2-3 second, be placed on the wire netting then and dry, contain in the culture dish of wet filter paper in leaf after will drying is placed on, inoculate 52 and make the cabbage looper larva.Culture dish is placed in the high humidity case mortality ratio of record larva after 3-5 days.The concentration of test progressively descends from 0.005%.The LC-50 value is listed in table III " CL " item down, represents with the percentage ratio of test compound in solution
Sitophilus zea-mais
Test compound dilutes with 50% aqueous acetone solution.4 corn grain are placed on soak 2-3 kind second in the testing liquid, have in the container of 10 corundum Sitophilusspp. imagos in being placed on after drying.Container built be placed under about 25 ℃ temperature, write down mortality ratio after 48 hours.Experimental concentration is since 0.1%, and progressively dropping to mortality ratio is 50%.The LC-50 value is listed in table III " MW " item down, represents with the percentage ratio of test compound in solution.
The aster leafhopper
The oat seed is implanted in the cuvette of the potted plant soil of interior Sheng commodity, when the about 10cm of plant height, seedling thinning is every glass three strain, and it is soaked 2-3 second in test compound 50% aqueous acetone solution.After plant did, cover was with a transparent plastics tubing, and insert in the cuvette bottom of pipe.Put into 10 aster leafhopper adult/nymphs in every pipe, the pipe top cover is with the white glass gauze.Write down mortality ratio after 48 hours.Experimental concentration progressively drops to appearance 50% mortality ratio since 0.001%.The LC-50 value is listed in table III " LH " item down, represents with the percentage ratio of test compound in soup.
Rice water weevil
Test compound is diluted in the acetone.Investigational agent drop (1ul) is imposed on the outside of belly of rice water weevil female adult worm belly, and the examination worm is 10.The examination worm of executing medicine is placed the container of wet cotton ball and rice leaf, build, temperature is maintained at about under 25 ℃, writes down mortality ratio after 48 hours.The concentration of test progressively drops to 50% death from 0.3mg/ml or every weevil 0.3ug.The LC-50 value is listed in table III " RWW " down, shows with the ug numerical table of every weevil test compound.
The acaricidal action evaluation test
Two-spotted spider mite (2SM) is as the examination worm of miticide test, and test method is as follows.
The Kidney bean seedling (Phaseolus sp.) of the about 10cm of height is transplanted in the cuvette of interior Sheng sandy loam and make the two-spotted spider mite of phase and sex that it is infected fully with mixing.After 24 hours, the plant that infects is turned around, be placed in 50% aqueous acetone solution of test compound and soak 2-3 second.The plant of handling remains in the greenhouse, be specified to the mortality ratio of mite after 5-7 days and when handling the ovum on plant through the mortality ratio of hatching imago/nymph.The concentration of test progressively descends from 0.05%.The LC-50 value is listed in table III " 2SM-A " (mite) and " 2SM-E " (being ovum) time, represents with the percentage ratio of test compound in solution.
The insecticidal activity of the compound that belongs to the scope of the invention of general formula defined but be not specifically noted in the text can be estimated with one or more above-mentioned methods.If the insect of compound to being mentioned shows 50% mortality ratio or is higher than 50% mortality ratio, just think that in the present invention it is " parasiticidal " under the dose level of initial test.
In actual applications, pure compound (activated compound) can be used as sterilant, but usually before using, at first they and one or more be suitable as sterilant inertia (that is, no chemically reactive, plant can tolerate or do not have herbicide effect) carrier or thinner be processed into preparation.
The preparation that contains The compounds of this invention can be any of multiple solid or liquid dosage form.The example of solid dosage has pulvis (supply to spray and use), granule, tablet, pulvis (using for seed dressing and other purposes) and other similar form.The example of liquid form has emulsion, solution, suspension agent, suspension concentrate, missible oil, paste.These preparations except containing one or more active compounds, can also contain various carriers or thinner; Tensio-active agent (wetting agent, dispersion agent and/or emulsifying agent); Solvent (water or organic solvent are as aromatic hydrocarbon solvent or chloro fat hydrocarbon solvent); Adhesive agent; Thickening material; Tackiness agent; Defoaming agents; And other material of mentioning herein.The solid carrier and the thinner that comprise in this class preparation have, and the natural mineral of for example pulverizing is as kaolin, alumina, burnt diatomite, lime carbonate, silicon-dioxide, diatomite, clay or the like; The vegetalitas product of synthetic mineral matter of pulverizing such as various silicate and pure aluminium silicate and pulverizing such as bark, Semen Maydis powder, curium end, cellulose powder and analogue thereof.The preparation that contains the sorbency clay also contains stablizer usually, as ethylene glycol, to prevent or to reduce the decomposition of active effective constituent.
Make the solid preparation and active compound and those solid carriers mentioned above or mixing diluents can be crushed to mixture suitable fineness again.Granule can be dissolved in active compound in the organic solvent, is sprayed on then to have absorbefacient having made on the particulate inert substance, for example makes on the silicon-dioxide.Also can add a little adhesive agents in order to active compound and solid particulate thorough mixing.
Wettable powder and paste can and grind active compound and one or more dispersion agents and/or solid carrier or mixing diluents and obtain.Also can comprise wetting agent and/or dispersion agent in the preparation, as the various basic metal of xylogen, methylcellulose gum, naphthalene sulfonic acid derivant, sulfated fatty alcohol ester and lipid acid and the salt of alkaline-earth metal.
Missible oil normally is dissolved in active compound in the organic solvent and adds emulsifying agent and obtains, and the example of solvent has butanols, pimelinketone, dimethyl benzene or high boiling aromatic hydrocarbon.In order to obtain suspension agent or the emulsion in water, but also can add humectant.
Suspension concentrate is by active compound, one or more dispersion agents and/or solid additive, and a kind of liquid mixing, and ground and obtained, used liquid is active compound dissolved substances hardly therein, and it can be water or organic solvent.
Liquid and solid preparation all can be made into little micella or micellar form, make the active compound that wraps in wherein with certain control speed, discharge lentamente in for some time.The droplet dia that contains the contained micellization of the liquid preparation of active compound and appropriate solvent is about the 1-50 micron.The material of micellization is high molecular inertia and porous film.
The solid micell formulations is the particulate form normally.It is that active ingredient moves with controlled speed in the particulate hole of carrier that the liquid that contains active ingredient in this particle is attracted to by porous polymeric membrane, or this film is broken and discharge active ingredient with controlled speed.
The material of typical micellization comprises natural and synthetic rubber, fibrous material, multipolymer, polyacrylonitrile, polyacrylic ester, polymeric amide, polymeric polyisocyanate, polyurethane(s) and the above-mentioned substance of styrene butadiene and the multipolymer of starch xanthate ester.
When using various atomising units, aerial spray technology for example during with the liquid form administered compound of high dispersing, can be used activity compound concentration up to 95%(weight) preparation, even use 100% active compound separately.For other various purposes, these compounds can various formulation be utilized, and according to the formulation of preparation and the purpose of use, they can contain the active compound of different quantities.
Usually, parasiticidal preparation can contain 5% to 95% active compound, and even more preferably 10% to 85%.The quantity that some typical formulation contain active compound is as follows: wettable powder, 25-80% active compound; Oil-suspending agent, emulsion, solution, suspension agent and missible oil, the 5-85% active compound; Water suspending agent, the 20-50% active compound; Pulvis (usefulness of spraying or other purposes), the 5-20% active compound; Granule and tablet, the 5-20% active compound.
Except active compound and various auxiliary agents used in making preparation mentioned above, other active compound that also can contain the types of mentioning in these preparations here, and other agricultural chemicals such as weedicide, sterilant, sterilant, miticide, nematocides, bactericide and plant-growth regulator.Included a certain specific agricultural chemicals in mixture, the effect classification that depends on its application target and require to replenish.The sterilant that is fit in these preparations of adding is as follows:
(a) natural pyrethrum or pyrethroid, as permethrin, esfenvalerate, Deltamethrin, cyhalothrin, bifenthrin, Fenvalerate, cyfloxylate, tefluthrin, Prallethrin, ether chrysanthemum ester, Tetramethrin, EXTHIN, five Flumethrins, prallethrin, 5-benzyl-3-furylmethyl-(E)-(1R, 3S) 2,2-dimethyl-3-(2-ketone-sulphur ring penta-3-fork base-) methyl cyclopropane carboxylicesters and PFBBR (suitable)-3-(2-fluoro-2-(methoxycarbonyl) vinyl)-2,2-dimethyl cyclopropane carboxylic acid ester;
(b) organophosphate is as Profenofos, second Toyodan, R-1504, SD-1750, parathion-methyl, azinphos-methyl, methyl thiol Systox, two ring phosphorus in heptan, thiometon, fenamiphos, monocrotophos, triazophos, acephatemet, Rogor, phosphamidon, Malathion, Chlorpyrifos 94, Phosalone, half rope phosphorus, Dyfonate, phorate, Volaton, pririmiphos_methyl, fenitrothion 95 and diazinon;
(c) carbamate (comprising aryl carbamate), as Aphox, cloethocarb, carbofuran, control aphid prestige, aldicarb, thiofurox, carbosulfan, the spirit of many worms, fenobucarb, Propoxur and oxamyl;
(d) benzoyl area kind is as triflumuron and UC 62644;
(e) organo-tin compound is as cyhexatin, fenbutatin oxide and azoles ring tin;
(f) microbiotic is as the plain class of A Wei desinsection or tangerine mite class, for example Ah crust's desinsection element, A Wei desinsection and tangerine mite element;
(g) insect hormone and synthetic stand-in thereof are as neotonin, the young biological ketone of guarantor, molting hormone, methoprene and illiteracy 512;
(h) insect sexual hormoue;
(i) organochlorine compound is as phenyl-hexachloride, DDT, Niran or Dieldrin-attapulgite mixture.
Except the sterilant of above-listed main chemical type, other sterilant with special target also can be used among the mixture, if during this mixture fit for service target.For example, the selected insecticides of using for special crop, as make the medicament of rice field control stem borer can be with Padan or buprofezin.In addition, in preparation, also can comprise, if any four mite piperazines, worm mite ether, chlordimeform, fluorine mite thiophene, mite thiophene ketone and the tetradifon of ovicidal action extraordinary insect population/worm phase effective insecticidal agent; Kelthane or propargite that acaricidal action is arranged; Adulticide such as bromopropylate, ethyl chlorfenethol; Or insect growth regulator(IGR) such as hydramethylon, cyromazine, rare worm ester, UC 62644 and the young urea that goes out.This class preparation also can contain soil disinfectant or fumigant, even fertilizer.So just make and use the preparation that contains active compound, other agricultural chemicals and fertilizer that one or more this paper mention in same place for multiple purpose and become possibility.
The insecticidal effective dose that pest control can be used active compound as described herein preferably utilizes nonvolatile compound under in the end a kind of situation in insect body, finish on the food of needs control insect place or insect's food-taking.Pest control can directly be executed active compound in insect or execute the food source of compound (crop-planting ground, herbage district and forest), insect in the place that will protect or other insect indirectly and perch area (as the breeding or the area of creeping) and realize.The consumption of active compound and the concentration of using depend on that direct administered compound or preparation are in insect or impose on plantation place, food or habitat indirectly and different.Under latter event, depend on characteristic of a certain or some insects that prevented and treated and the environment of plant, generally be every acre of 0.01-100 pound (about 0.011-111 kilogram/hectare) approximately.
It is pointed out that for the effectively preventing insect, active compound itself must not have insecticidal activity.Purpose of the present invention also comprises that compound is subjected to externalities, has insecticidal activity as the influence of light or heat, and perhaps compound enters certain physiological action of insect body internal cause and is converted into and has insecticidal activity.
Compound of the present invention can be used for preventing and treating various insects, for example:
Black peach aphid
Cotten aphid
Beans winged euonymus aphid
Pea tail reparing aphid
Aedes aegypti
Anopheles
Culex
The red stinkbug of cotton band line
Housefly
Large white butterfly
Small cabbage moth
The horseradish daikon leaf beetle
The hoof armored scale belongs to
Aleyrodes (trialeurodes vaporariorum)
Bemisia tabaci
Groton bug
Periplaneta americana
Oriental cockroach
Prodenia litura
Cigarette beetle
Locust (chortiocetes terminifera)
The chrysomelid genus of root
Agrotis
Striped rice borer
Corn stem snout moth's larva
Brown paddy plant hopper
Nephotettix bipunctatus
Rice green leafhopper
Panonychus ulmi
Citrus red mite (crm)
Two-spotted spider mite
Tetranychus telarius
The tangerine rust mite that rues
Polyphagotarsonemus latus Banks
Short whisker Acarapis
The preparation that contains one or more described active compounds under insecticidal effective dose, can be applied to plant with method commonly used.Plant the area of perching of place, insect or insect.
When the sfgd. with crop or other plant was associated use, using can be (promptly the using before insect infection) of protectiveness or (promptly the using after insect infection) that product removes property.Contain active ingredient medicinal powder and various liquid preparation and can use also available aircraft dusting or spraying with motor duster, arm-type and hand sprayer and powder sprayer.In a kind of method in back was used, preparation also was effective under low-down dosage.
The preparation that contains active compound also can be added in the irrigation water, is applied to pending field piece.This application process, compound are absorbed by soil with water and infiltrate in the native boundary.
The preparation that contains active compound can also be applied on the seed as seed dressing, prevents that seed from after planting and during germination suffering the harm of soil pests.Usually mix in suitable mixing tank with the preparation of liquid or solid form (preferred liquid) and seed and realize.Use liquid preparation can contain adhesive agent or tackiness agent for this purpose, for example methylcellulose gum, ethyl cellulose etc. are helped preparation attached on the seed.If when the solid preparation is used as seed dressing, can on seed, spray adhesive agent when puddling or after puddling.
When the soil insecticide, active compound or contain the preparation of active compound can be with any method commonly used, before sowing, during sowing, or sowing is afterwards and mixing with soil.Contain the solid of active compound or liquid preparation can be before plantation or during plantation by raking the soil level, plough or other married operation mixing in the soil, its objective is activeconstituents is under the upper soll layer, more effectively prevent and treat deleterious larva.
The example that contains the various preparations of active compound of the present invention has:
Preparation A: granule
Composition weight %
Active compound 10
Attapulgite 85
Triethylene glycol 5
Amount to 100%
Preparation B: wettable powder
Composition weight %
Active compound 80
Wetting agent (dialkyl group naphthalenesulfonate) 1
Dispersion agent (sodium lignosulfonate) 4
Thinner (neusilin) 15
Amount to 100%
Formulation C: dilute solution
Composition weight %
Active compound 5
Solvent (dimethylbenzene) 95
Amount to 100%
Preparation D: missible oil
Composition weight %
Active compound 50
Emulsifying agent (metal organic sulfonate
Mixture with polyoxyethylene ether) 10
Solvent (dimethylbenzene) 40
Amount to 100%
Preparation E: strong solution
Composition weight %
Active compound 90
Solvent (dimethylbenzene) 10
Amount to 100%
Claims (7)
1, the compound that has following molecular formula:
In the formula,
R
1Be hydrogen, halogen, C
1-C
4Alkoxyl group, C
1-C
4Haloalkyl, C
1-C
4Halogenated alkoxy or C
1-C
4Halogenated alkylthio;
R
2Be hydrogen, halogen, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, C
1-C
4Haloalkyl, C
1-C
4Halogenated alkoxy or C
1-C
4Halogenated alkylthio;
R
3Be hydrogen, halogen or C
1-C
4Haloalkyl; Or
R
1And R
2Merge into C
1-C
4Alkylene oxide group or halo C
1-C
3Alkylene oxide group;
Regulation R
1, R
2, and R
3Can not be hydrogen;
R
4Be methyl, ethyl, n-propyl, C
3-C
7Branched alkyl, C
1-C
6Haloalkyl, C
2-C
6Alkenyl or cyclopropyl, preferably contain 1-4 methyl or 1-2 halogenated cyclopropyl
R
5For:
R
6Be phenyl, benzyl, C
3-C
4Alkenyl or C
3Alkynyl;
R
7, R
8, R
10And R
11The halogen of respectively doing for oneself; With
R
9Be methyl, methoxymethyl, methylthio group, methylthiomethyl, methylol, cyano methyl, benzyl, C
3-C
4Alkenyl, C
3Alkynyl or proyl amino.
2, the compound in the claim 1, its R
4Be ethyl, sec.-propyl, pseudoallyl, dichloromethyl or cyclopropyl.
3, the compound in the claim 1 or 2, its R
1Be hydrogen, halogen, trifluoromethyl, difluoro-methoxy, difluoro bromine methoxyl group or difluoro chlorine methoxyl group; R
2Be hydrogen, halogen, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy or trifluoromethyl; And R
3Be hydrogen.
4, any compound among the claim 1-3, its R
5For
And R
7, R
8, R
10And R
11Be fluorine.
5, the compound in the claim 4, its R
9Be methoxymethyl, methylthiomethyl, benzyl, allyl group, 2-methacrylic or propine-2-base.
6, the method for control insect comprises each compound among the claim 1-5 is applied to the place that insect, insect perch with the effective dosage of desinsection, maybe needs the place with insecticide control.
7, parasiticidal preparation, its component for any compound among the claim 1-5 of (a) insecticidal effective dose and (b) are suitable for the diluent or carrier that sterilant is used.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57913190A | 1990-09-06 | 1990-09-06 | |
| US579131 | 1990-09-06 | ||
| US621157 | 1990-11-30 | ||
| US07/621,157 US5189060A (en) | 1987-11-17 | 1990-11-30 | Imidate insecticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1059514A true CN1059514A (en) | 1992-03-18 |
Family
ID=27077677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN91108681A Pending CN1059514A (en) | 1990-09-06 | 1991-09-05 | Imidate insecticides |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN1059514A (en) |
| WO (1) | WO1992004317A2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112279779B (en) * | 2019-07-24 | 2022-02-15 | 中国科学院大连化学物理研究所 | Preparation method of chiral aryl oxime ether compound |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3453311A (en) * | 1966-01-20 | 1969-07-01 | Rohm & Haas | Aryl n-(aryl)-alkanoimidates |
| CH482400A (en) * | 1967-03-28 | 1969-12-15 | Ciba Geigy | Pesticides |
| DE2944849A1 (en) * | 1979-11-07 | 1981-06-04 | Bayer Ag, 5090 Leverkusen | Insecticidal, acaricidal phenoxy-benzyl thio:ester derivs. - prepd. e.g. by reaction of a mono- or di-thio:carboxylic acid with a 3-phenoxy-benzyl halide |
| ATE106393T1 (en) * | 1987-11-17 | 1994-06-15 | Zeneca Inc | IMIDATE WITH INSECTICIDAL ACTIVITY. |
-
1991
- 1991-09-04 WO PCT/US1991/006383 patent/WO1992004317A2/en unknown
- 1991-09-05 CN CN91108681A patent/CN1059514A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO1992004317A2 (en) | 1992-03-19 |
| WO1992004317A3 (en) | 2004-04-29 |
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C03 | Withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |