CN1456054A - Methoxy methyl acrylate compounds as bactericidal agent - Google Patents

Methoxy methyl acrylate compounds as bactericidal agent Download PDF

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Publication number
CN1456054A
CN1456054A CN 03120882 CN03120882A CN1456054A CN 1456054 A CN1456054 A CN 1456054A CN 03120882 CN03120882 CN 03120882 CN 03120882 A CN03120882 A CN 03120882A CN 1456054 A CN1456054 A CN 1456054A
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Prior art keywords
compound
composition
powdery mildew
mildew
cucumber
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CN 03120882
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CN1201657C (en
Inventor
许天明
陈定花
孔小林
朱卫钢
郑昀红
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Zhejiang Chemical Industry Research Institute Co Ltd
Sinochem Lantian Co Ltd
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Chemical Industry Inst Of Zhejiang Prov
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Priority to CN 03120882 priority Critical patent/CN1201657C/en
Publication of CN1456054A publication Critical patent/CN1456054A/en
Priority to PCT/CN2004/000226 priority patent/WO2004084632A1/en
Priority to BRPI0409037-3A priority patent/BRPI0409037A/en
Priority to TR2005/03847T priority patent/TR200503847T1/en
Priority to AU2004224838A priority patent/AU2004224838A1/en
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Priority to ZA200508026A priority patent/ZA200508026B/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

Abstract

The disinfectant for powder mildew, frosty mildew and anthracnose, its application, and its preparing process disclosed. Said disinfectant is a composition of 2-(2-((2.5-dimethylphenoxy)methylphenyl))-3-methyl methoxyacrylate, and its stereoisomer.

Description

Methoxy-methyl acrylate compounds bactericide
The technology of the present invention field
The present invention relates to a kind of methoxy-methyl acrylate class disinfectant use in agriculture.The invention further relates to a kind of methoxy-methyl acrylate compound, its preparation method, its microbicide compositions and uses thereof with efficient sterilizing effect.
In order to obtain under very little dosage, just to control various fungal disease compounds, inventors of the present invention have synthesized some compounds wherein, these compounds have the broad-spectrum sterilization activity can be used for preventing and treating on the crop by multiple fungus-caused diseases such as Phycomycetes, Oomycete, Ascomycetes and deuteromycetes, and because this compound has very high biologically active makes just can obtain fine control efficiency under very low dosage.This compounds shows outside the good biologically active powdery mildew, downy mildew, anthracnose, and anthrachose of grape, the grape white blister of grape also had preventive and therapeutic effect.
Compound provided by the invention not only has very high biologically active, and very friendly to environment, and environment is not polluted.The invention provides compound and not only have very high biologically active, and low with world's similar products comparative cost of production, be very promising disinfectant use in agriculture new varieties.
Background technology
At US4, disclose some methoxy-methyl acrylate compounds in 914, No. 128 patent applications, and disclose compound wherein and have bactericidal activity.
The applicant is surprised to find that, the not concrete disclosed compound of some in its formula has excellent Fungicidally active, and finished the present invention thus.
The methoxy-methyl acrylate series bactericidal agent is the efficient agricultural fungicide that comes by structure of modification from native compound.Their characteristics are that sterilization is wide, low to other bio-toxicity, Environmental compatibility good.There is many agricultural chemicals major company to carry out this respect research in the world, found several methoxy-methyl acrylate compounds that fine market prospects are arranged.It is increasing that ratio is occupied in this series bactericidal agent market, and possible substituted triazole series bactericidal agent becomes the first kind of disinfectant use in agriculture.
The present invention's general introduction
The invention provides new methoxy-methyl acrylate compounds and its preparation method, and microbicide compositions and purposes.The chemical name of methoxy-methyl acrylate fungicide compound of the present invention is:
(E)-2-(2-((2, the 5-dimethyl phenoxy) aminomethyl phenyl))-3-methoxy-methyl acrylate structural formula is:
Figure A0312088200041
Compound of the present invention can prepare by the following method:
Method one reaction is as follows:
Figure A0312088200042
Compound I can prepare like this: in appropriate solvent, 2 of adding formula II, the 2-of 5-xylenol and formula III (2-halogenated methyl phenyl)-3-methoxy-methyl acrylate adds suitable alkali again, makes with the appropriate time internal reaction under suitable temperature.Wherein X leaving group such as the halogen among the III is preferably chlorine, bromine or iodine.
Preferred solvent is acetone or oxolane.
Wherein alkali comprises organic base and inorganic base: organic base comprises triethylamine, pyridine etc.; Inorganic base comprises sodium hydroxide, potassium hydroxide, sodium hydride, sodium carbonate, potash etc.Preferred bases of the present invention is sodium carbonate or potash.
Preferred temperature is 0～100 ℃.The method two reaction is as follows:
Method two prepares the Compound I process: in appropriate solvent, add 2 of formula II, 5-xylenol and formula IV compound add suitable alkali most, make V with the appropriate time internal reaction under suitable temperature.X leaving group such as the halogen among the III wherein, preferred chlorine, bromine or iodine.V adds suitable alkali again in appropriate solvent, add an amount of methyl formate, makes VI with the appropriate time internal reaction under suitable temperature.VI adds methylating reagent in appropriate solvent, as dimethyl suflfate, iodomethane etc., add suitable alkali again, makes Compound I with the appropriate time internal reaction under suitable temperature.
Wherein when preparation V: preferred solvent is acetone or oxolane.
Wherein alkali comprises organic base and inorganic base: organic base comprises triethylamine, pyridine etc.; Inorganic base comprises sodium hydroxide, potassium hydroxide, sodium hydride, sodium carbonate, potash etc.Preferred bases of the present invention is sodium carbonate or potash.
Preferred temperature is 0～100 ℃.
Preferred bases is sodium methoxide or sodium hydride etc. when preparation VI; Preferred solvent is ether or methyl alcohol.Preferred temperature is subzero 5～100 ℃.
Wherein when preparation I: preferred solvent is acetone or oxolane.
Wherein alkali comprises organic base and inorganic base: organic base comprises triethylamine, pyridine etc.; Inorganic base comprises sodium hydroxide, potassium hydroxide, sodium hydride, sodium carbonate, potash etc.Preferred bases of the present invention is sodium carbonate or potash.
Preferred temperature is 0～100 ℃.
Compound I of the present invention is effective fungicide.Be particularly suitable for preventing and treating the following plants disease:
Barley and wheat powdery mildew, vegetables powdery mildew, cucurbits powdery mildew, fruit tree powdery mildew, grape powdery mildew, powdery mildew of strawberry and flowers powdery mildew; Wheat and big wheat yellow rust, leaf rust and other rust.
Cucumber downy mildew, downy mildew of garpe; Diseases such as the anthracnose on melon.
The present invention also provides bactericidal composition of compound as defined above and preparation method thereof.
Composition of the present invention preferably contains from the active ingredient of the formula (I) of 0.1～99.0% weight.Can in composition, add suitable carriers and surfactant component when needing.
The preparation method of the present composition mixes Compound I and at least a carrier.This composition can also contain other pesticide activity component.
Carrier of the present invention is the material that satisfies following condition: being convenient to be applied to pending site after it and active component are prepared, for example can be plant, seed or soil; Perhaps help storing, transport or operation.Carrier can be solid or liquid and can use any used carrier in preparation desinsection, bactericidal composition usually.
Suitable solid carrier comprises natural and synthetic silicate, for example diatomite, talcum, Attagel, alumina silicate (kaolin), montmorillonite and mica; Calcium carbonate, calcium sulphate, ammonium sulfate; Synthetic oxidation calcium silicates or alumina silicate; Element such as carbon and sulphur; Natural and synthetic resin such as cumarone resin, polyvinyl chloride and styrene polymer and copolymer; Solid polystream phenol; Pitch; Wax such as beeswax, paraffin wax.
Suitable liquid-carrier comprises water; Alcohol is as isopropyl alcohol and ethanol; Ketone such as acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK) and cyclohexanone; Ether; Aromatic hydrocarbons such as benzene, toluene and dimethylbenzene; Petroleum distillate such as kerosene and mineral oil; Chlorohydrocarbon such as carbon tetrachloride, perchloroethylene and trichloroethanes, usually, these mixtures of liquids also are suitable.
Desinsection, bactericidal composition are processed into the form of concentrate usually and are used for transportation with this, by the user it are diluted before using.Having of a spot of supporting surfactant helps dilution.Like this, in composition of the present invention, preferably contain surfactant.
Surfactant can be emulsifier, dispersant or wetting agent: it can be ionic surface active agent or non-ionic surface active agent.As: the sodium salt of polyacrylic acid and lignin sulfonic acid or calcium salt; The fatty acid or fatty amine or the acid amides that contain at least 12 carbon atoms in the molecule; Oxirane and or the condensation product of expoxy propane; Glycol, sorbierite, sucrose or the pentaerythrite sour fat of fat and these esters and oxirane and or encircle the condensation product of oxirane; Fatty alcohol or alkylphenol such as paraoctyl phenol or paraoctyl phenol and oxirane and or the condensation product of expoxy propane; The sulphate of these condensation products or sulfonate; In molecule, contain the sulfuric acid of at least 10 carbon atoms or the alkali metal or the alkali salt of sulphonic acid ester, particular certain cancers, sodium lauryl sulfate for example, the secondary Arrcostab sodium of sulfuric acid, sulfonated castor oil sodium salt, alkyl aryl sulfonic acid ester sodium such as pelopon A.
The example of composition of the present invention is wetting powder, pulvis, granule, emulsible concentrating agents, emulsion, suspension concentrating agents, aerosol and aerosol.Wetting powder contains 20-80% weight active component usually, and usually except that solid inert carrier, also contains 2～10% weight fraction powders, and if needs or add 0～10% weight stabilizing agent and or other additive such as bleeding agent or sticker.Pulvis may be molded to the pulvis concentrating agents that has the similar composition of wetting powder but dispersant is arranged usually, further with the solid carrier dilution, is contained 0.5～10% weight composition of active components usually in the ground.Granula is made usually has 10 and 100 order sizes, and available agglomerating or injection technique preparation.Usually, granula contains the active component of 0.1～80% weight and 0～10% weight additive such as stabilizing agent, surfactant, sustained release agent etc.So-called " dry powder can flow " is made up of the relatively little particle with relative high concentration active component.Outside but emulsion concentrate desolventizes, when needs, contain cosolvent usually, 1～50%W/V active component, other additives of 2～20%W/V emulsifier and 0～20%W/V such as stabilizing agent, bleeding agent and corrosion inhibitor.Suspend to concentrate and contain the active component of 10～80% weight, the dispersant of 0.5～15% weight, other additive such as defoamer, corrosion inhibitor, stabilizing agent, bleeding agent and the sticker of 0.1～10% weight together usually.
Water dispersant and emulsifier, for example by dilute with water according to the composition that wetting powder of the present invention or concentrate obtain, also list the scope of the invention in.Said emulsion can have Water-In-Oil or two types of oil-in-water.
By in composition, adding other one or more fungicides, make it have wider activity than independent compound (I).In addition, other fungicides can have synergistic effect to the bactericidal activity of compound (I).Can be included in the example of the fungicide compound in the present composition: captan, folpet, phonetic mould amine, tridemorph, Fenarimol, fludioxonil, red copper oxid, Difenoconazole, zineb, mancozeb, tmtd, difoltan, iprodione, the methyl sclex, first and second sclexes, own azoles alcohol, nitrile bacterium azoles, Tebuconazole, Pencycuron, frost urea cyanogen, biguanide spicy acid salt, prothiocarb, ring bacterium amine, flumorph, the fluorine azoles, SSF-129, picoxystrobin, metrafenone, pyraclostrobin, resveratro, dimoxystrobin, UBF-307, BASF490F, ICIA5504, TH-164, RH7592, ester bacterium urea, alkene azoles alcohol, the fluorine uride, carbendazim, benomyl, triazolone, cyproconazole, the mould prestige of second, thiophanate methyl, hydroxyisoxazole; butadiene morpholine; Propamocarb; metalaxyl; furalaxyl; M 9834; dislike acid amides; methasulfocarb; pyrifenox; fenpropidin; mepanipyrim; dimethomorph; fenpiclonil; seed dressing is strong; propiconazole; tpn; diazine Nong; copper sulphate; Euparen; aliette; dislike mould spirit; etc.
Can have with the insecticide of compound formation composition of the present invention: the insecticide fenisobromolate, dicofol, parathion-methyl, 1605, Folithion, diazinon, carbosulfan, chlopyrifos, sharp special to the greatest extent, eliminate, Methomyl, the desinsection list, dimehypo, Padan, Avermectin, permethrin, cypermethrin, tetramethrin, tefluthrin, cyfloxylate, sumicidin, flufenoxuron, the desinsection urea, decide the worm urea, azoles mite ester, Imidacloprid, ABG-6215, Hostathion, quinoline mite ester, methamidophos, pyridaben, four mite piperazines etc.
Embodiment
Come by following concrete example that the present invention will be described in detail, except as otherwise noted among the application Umber one weight The amount meter:
Synthetic embodiment:
At room temperature with 12.2g 2, the 5-xylenol is added to 500ml and fills in the there-necked flask of 150ml dry acetone, add 13.8g potash then, stirring at room 20 minutes slowly adds 28.5g (E)-2-(2-(bromomethyl) phenyl)-3-methoxy-methyl acrylate then.Back flow reaction finished in 3 hours then, filtered, and concentrated, and got crude product.Mixed liquor (1: 4) with ethyl acetate and benzinum obtains Compound I 26.08g for eluent carries out column chromatography, is white solid, and yield is 80%.Fusing point: 108～110 ℃
1HNMR：2.235(3H，s)，2.279(3H，s)，3.706(3H，s)，3.835(3H，s)，4.944(2H，s)，6.584(1H，s)
6.655-6.673(1H，d)，7.013-7.032(1H，d)，7.164-7.168(2H，d)，7.300-7.7.382(2H，m)，
7.596(1H，s)，7.617(1H，s)
Annotate: 1The HNMR spectrum is to use CDCl 3The solvent record.Abbreviation used in experiment is as follows:
The bimodal m=multimodal of the unimodal d=of NMR=nuclear magnetic resonnance s=
Example of formulations
Example of formulations 1
40 kilograms of compounds of the present invention, 53 kilograms in diatomite, 4 kilograms of C12-20 alcohol sulfuric esters, 3 kilograms of neopelexes evenly mix above composition, pulverize, and must contain the wetting powder of effective composition 40%.
Example of formulations 2
30 kilograms of of the present inventionization things, 33 kilograms of dimethylbenzene, 30 kilograms of dimethyl formamides, 7 kilograms of polyxyethylated propyl ether evenly mix above composition, dissolve, must contain the emulsion of effective composition 30%.
Example of formulations 3
10 kilograms of compounds of the present invention, 89 kilograms of talcum powder, polyxyethylated propyl ether kilogram evenly mix above composition, pulverize, and must contain the pulvis of effective composition 10%.
Example of formulations 4
5 kilograms of compounds of the present invention, 73 kilograms of clays, 20 kilograms of bentonites, 1 kilogram of dioctyl sulfo-sodium succinate, 1 kilogram of sodium phosphate evenly mix above composition, after fully pulverizing, add suitable quantity of water.Fully mix, granulation after the drying, must contain the granule of effective composition 5% again.
Example of formulations 5
10 kilograms of compounds of the present invention, 4 kilograms of sodium lignin sulfonates, 1 kilogram of neopelex, 1 kilogram of xanthic acid, 84 kilograms in water evenly mixes above composition, and wet lapping is below 1 micron to granularity, obtains containing effective composition and be 10% colloidal suspending agent.
Example of formulations 6
8 kilograms of The compounds of this invention, 50 kilograms of mancozebs, 30 kilograms of kaolin, 4 kilograms of neopelexes, 8 kilograms of sodium lignin sulfonates mix mentioned component, after fully pulverizing, mixture content is 58% wetting powder.
Example of formulations 7
1 kilogram of The compounds of this invention, 20 kilograms of triazolones, 64 kilograms of kaolin, 6 kilograms of neopelexes, 9 kilograms of sodium lignin sulfonates evenly mix above composition, after fully pulverizing, mixture content is 21% wetting powder.
Drug effect embodiment:
Compound of the present invention has fine biologically active with existing bactericide ratio, can prevent and treat well under very low dosage by fungus-caused disease, and powdery mildew, rust, downy mildew, anthracnose are had good especially effect.As powdery mildew, cucumber white powder, pumpkin white powder, powdery mildew of strawberry, the grape powdery mildew of wheat, barley, wheat, big wheat rust, downy mildew of garpe, cucumber downy mildew, cucumber anthracnose.Also there is certain inhibitory action the position to anthracnose of grape, white blister in addition.
Drug effect embodiment 1: prevent and treat powdery mildew of cucumber protection and therapeutic action test (indoor)
Test medicine is that The compounds of this invention I (missible oil of content 5%) establishes 10,5,2.5,1.25,0.625, six concentration of 0.3125ppm.Contrast ZA-1963 (being the picoxystrobin of Syngenta Co.,Ltd, commercial compound in the promptly similar patent) (missible oil of content 5%) establishes 10,5,2.5,1.25,0.625, six concentration of 0.3125ppm.Contrast medicament 20% triazolone missible oil establishes 100,50,25ppm.Selection grows to 2 leaves, the open and flat strong seedling spray of the cucumber medicine of potted plant two true leaves of one heart stage, and back 24 hours spray medicines are inoculated in inoculation in 24 hours behind the prophylactic tria spray medicine, therapeutic test.Inoculate the cultivation of preserving moisture in the cucumber children dislocation climatic cabinate of back, 7 days " Invest, Then Investigate " preventive effects.The results are shown in Table 1:
Protection of table 1 powdery mildew of cucumber and therapeutic action result of the test:
Medicament Concentration (ppm) Powdery mildew of cucumber
Preventive effect (%) Result of treatment (%)
Compound (I) ????10 ????100 ????98.89
????5 ????100 ????97.53
????2.5 ????97.22 ????88.89
????1.25 ????90.28 ????85.71
????0.625 ????85.31 ????64.81
????0.315 ????63.11 ????29.63
????ZA-1963 ????10 ????98.15 ????86.11
????5 ????88.89 ????68.52
????2.5 ????81.75 ????36.11
????1.25 ????75.60 ????23.42
????0.625 ????47.63 ????8.33
????0.315 ????41.67 ????0.0
Triazolone ????100 ????100
????50 ????81.25
????25 ????45.40
Protection and therapeutic test result show: the Compound I prevention slightly is better than treatment.0.625ppm prevention is 85.31%, treatment is 64.81%.Find that simultaneously the prevention of compound (I) and the obvious activity of result of treatment are better than ZA-1963, particularly therapeutic action.The biologically active of Compound I is better than triazolone far away.
Drug effect embodiment 2 protections of control wheat powdery mildew and therapeutic action test (indoor)
Test medicine is that The compounds of this invention I (missible oil of content 5%) establishes 25,12.5,625,3.125,1.563, six concentration of 0.781ppm.Contrast ZA-1963 (being the picoxystrobin of Syngenta Co.,Ltd, commercial compound in the promptly similar patent) (missible oil of content 5%) establishes 25,12.5,6.25,3.125,1.563, six concentration of 0.781ppm.Contrast medicament 20% triazolone missible oil establishes 100,50,25ppm.Selection grows to 2 leaves, the potted plant wheat spray medicine of one heart stage, and back 24 hours spray medicines are inoculated in inoculation in 24 hours behind the prophylactic tria spray medicine, therapeutic test.Inoculate the cultivation of preserving moisture in the wheat dislocation climatic cabinate of back, 7 days " Invest, Then Investigate " preventive effects.The results are shown in Table 2
Little table powdery mildew protection of table 2 and therapeutic action result of the test
Medicament Concentration (ppm) Wheat powdery mildew
Preventive effect (%) Result of treatment (%)
Compound (I) ????25 ????100 ????100
????12.5 ????100 ????100
????6.25 ????100 ????100
????3.125 ????100 ????100
????1.563 ????98.33 ????97.33
????0.781 ????87.43 ????84.13
????ZA-1963 ????25 ????100 ????99.77
????12.5 ????99.60 ????98.31
????6.25 ????91.30 ????82.95
????3.125 ????93.61 ????73.15
????1.563 ????78.18 ????71.97
????0.781 ????53.05 ????38.97
Triazolone ????100
????50
????25
Protection and therapeutic test result show: find that the prevention of Compound I and the obvious activity of result of treatment are better than ZA-1963, therapeutic action is more obvious.The biologically active of Compound I is better than triazolone far away.3 pairs of wheat powdery mildew simulations of drug effect embodiment field trial
Compound (I) concentration of treatment is 50,25,12.5,6.25,3.125ppm, and the concentration of treatment of contrast medicament ZA-1963 is identical with Compound I, and the concentration of treatment of triazolone is 100,50,25ppm.Potted plant wheat is cultured to the 4-5 leaf phase, gives free rein to and fall ill, carry out foliar spray by above-mentioned set concentration and handle 10 days " Invest, Then Investigate " preventive effects to mid-term.The results are shown in Table 3
Table 3 pair wheat powdery mildew simulation field trial
Medicament Concentration (mg/l) Preventive effect (%)
Compound (I) ????50 ????100
????25 ????100
????12.5 ????100
????6.25 ????95.60
????3.125 ????70.37
????ZA-1963 ????50 ????93.61
????25 ????83.26
????12.5 ????64.25
????6.25 ????49.57
????3.125 ????41.83
Triazolone ????100 ????64.93
????50 ????13.85
The simulation field test results shows that Compound I is dispenser during to mid-term to potted plant wheat natural occurrence, still show very high preventive and therapeutic effect, and preventive effect is better than contrasting medicament ZA-1963 and triazolone.
4 lasting periods of drug effect embodiment test
The concentration of treatment of Compound I and contrast medicament ZA-1963 is 50, and 25mg/l, tested object are wheat powdery mildew.Spray medicine when two true leaves of potted plant wheat are open and flat, 24 hours inoculation wheat powdery mildews behind the spray medicine, postvaccinal wheat moves to the cultivation of preserving moisture in the greenhouse, handles back investigation in 7,10,15,20,25,30 days preventive effect.The results are shown in Table 4
Table 4 lasting period result of the test
Medicament Concentration mg/l Preventive effect (%)
7 days 10 days 15 days 20 days
Compound (I) ????50 ????100 ????100 ??99.6 ??88.16
????25 ????100 ????100 ??98.51 ??87.23
??ZA-1963 ????50 ????100 ????100 ??96.43 ??85.21
????25 ????100 ????100 ??96.31 ??84.68
The lasting period test shows: under the condition of greenhouse artificial infection, the lasting period of Compound I is slightly longer than ZA-1963.Efficiency test (field) the field efficacy squash marble dust test of 5 pairs of squash marble dusts of drug effect embodiment is carried out in the booth of modern agriculture garden, ShaoXing,ZheJiang city in June, 2002.
Compound I (10% aqueous suspension) establishes 50,25,12.5, four concentration of 6.25ppm, and the contrast medicament is that to establish concentration be 100ppm to 20% triadimefon EC.Other establishes the clear water contrast.Every processing repeats for 4 times.7 days " Invest, Then Investigate "s of dispenser.The results are shown in Table 5
Efficiency test (field) result of table 5 pair squash marble dust
Medicament Concentration (ppm) Disease index Disease refers to increase number Preventive effect (%)
Compound (I) ????50 ??17 ????1.5 ????91.8
????25 ??22.75 ????1 ????96.4
????12.5 ??22.5 ????2.5 ????90.9
????6.25 ??23.75 ????2 ????92.7
Triadimefon ????200 ??20 ????7.25 ????72.7
????CK ??44.25 ????27.5 ????27.5
Annotate: CK preventive effect hurdle is that disease refers to value added.
As can be seen from Table 5: compound has very high activity at 6.25ppm to the pumpkin white powder, obviously is better than contrasting the medicament triadimefon.Efficiency test (field) the field control powdery mildew of cucumber test of 6 pairs of powderys mildew of cucumber of drug effect embodiment is carried out in the booth of modern agriculture garden, ShaoXing,ZheJiang city in June, 2002.
Compound I (10% aqueous suspension) establishes 50,25,12.5, four concentration of 6.25ppm, and the contrast medicament is that to establish concentration be 100ppm to 20% triadimefon EC.Other establishes the clear water contrast.Every processing repeats for 4 times.7 days " Invest, Then Investigate "s of dispenser.The results are shown in Table 6
Efficiency test (field) result of table 6 pair powdery mildew of cucumber
Medicament Concentration (ppm) Disease index Disease refers to increase number Preventive effect (%)
Compound (I) ????50 ??21.25 ????0.5 ????98.6
????25 ??26.75 ????1.25 ????96.5
????12.5 ??21.25 ????2.75 ????92.2
????6.25 ??24.5 ????2.75 ????92.2
Triadimefon ????200 ??37.25 ????11 ????68.8
????CK ??59.5 ????35.25 ????35.25
Annotate: CK preventive effect hurdle is that disease refers to value added.As can be seen from Table 6: Compound I has very high activity at 6.25ppm to the cucumber white powder, obviously is better than contrasting the medicament triadimefon.Drug effect embodiment 7 compounds (I) are 100,50,25,12.5 to cucumber downy mildew efficiency test (indoor) Compound I concentration of treatment, 6.25ppm, and the concentration of treatment of contrast medicament ZA-1963 is identical with Compound I, and the metalaxyl concentration of treatment is 500ppm.Selection grows to 2 leaves, the open and flat strong seedling spray of the cucumber medicine of potted plant two true leaves of one heart stage, and back 24 hours spray medicines are inoculated in inoculation in 24 hours behind the prophylactic tria spray medicine, therapeutic test.Inoculate the cultivation of preserving moisture in the cucumber children dislocation climatic cabinate of back, 7 days " Invest, Then Investigate " preventive effects the results are shown in Table 7
Efficiency test (indoor) result of table 7 pair cucumber downy mildew
Medicament Concentration (ppm) Preventive effect (%)
Compound (I) 100 100
?50 100
?25 100
?12.5 97.18
?6.25 91.55
?3.125 77.46
ZA-1963 ?100 91.55
?50 60.56
?25 46.48
?12.5 40.84
?6.25 26.76
?3.125 9.86
Metalaxyl ?500 70.11
Compound I obviously is better than contrasting medicament ZA-1963 to the preventive effect of cucumber downy mildew under same concentrations under greenhouse experiment, obviously is better than metalaxyl.The efficiency test (field) of 8 pairs of downys mildew of garpe of drug effect embodiment
The test of field control downy mildew of garpe is carried out in agricultural science and technology demonstration field, peace Dangtu County stone bridge township, Wei Sheng Maanshan City in July, 2002.Compound I (5% missible oil) establishes 200,100,50,25, five concentration of 12.5ppm, and contrast medicament 72% Du Pont gram reveals wetting powder and establishes 1000ppm concentration.Other establishes blank, and every processing repeats 4 times.7 days " Invest, Then Investigate "s of spray medicine.Result such as table 8
Efficiency test (field) result of table 8 pair downy mildew of garpe
Medicament Concentration (ppm) Radix before the medicine Sick index Preventive effect (%)
Compound (I) ???12.5 ????1.61 ????4.89 ????50.94
???25 ????1.89 ????4.33 ????62.97
???50 ????2.00 ????3.89 ????68.58
???100 ????2.28 ????3.20 ????77.34
???200 ????2.22 ????2.47 ????82.05
Ke Lu ???1000 ????1.55 ????1.68 ????82.49
??CK ????1.89 ????11.70
As can be seen from the results, Compound I is suitable with contrast medicine gram dew 1000ppm at 200ppm at control grape downy mildew.The efficiency test (field) of 9 pairs of cucumber downy mildews of drug effect embodiment
The test of field control cucumber downy mildew is carried out in agricultural science and technology demonstration field, peace Dangtu County stone bridge township, Wei Sheng Maanshan City in July, 2002.Compound I (5% missible oil) establishes 200,100,50,25, five concentration of 12.5ppm, and contrast medicament 72% Du Pont gram reveals wetting powder and establishes 1000ppm.Other establishes blank, and every processing repeats 4 times.7 days " Invest, Then Investigate "s of spray medicine.Result such as table 9
Efficiency test (field) result of table 9 pair cucumber downy mildew
Medicament Concentration (ppm) Radix before the medicine Sick index Preventive effect (%)
Compound (I) ????12.5 ????0.96 ????3.89 ????51.38
????25 ????1.07 ????3.04 ????65.91
????50 ????1.04 ????2.59 ????70.01
????100 ????0.93 ????1.84 ????76.12
????200 ????0.89 ????1.28 ????82.67
Ke Lu ????1000 ????0.93 ????1.13 ????85.33
????CK ????0.78 ????6.48
As can be seen from the results, Compound I is suitable with contrast medicine gram dew 1000ppm at 200ppm at control cucumber downy mildew.The concentration of treatment of anti-effect test (indoor) Compound I of 10 pairs of cucumber anthracnoses of drug effect embodiment and contrast medicament ZA-1963 is 500,250,125,62.5,31.25ppm.Tested object is a cucumber anthracnose, spray medicine when potted plant cucumber seedling grows to a leaf period, and the spray medicine is inoculated the anthracnose spore suspension after 24 hours, the inoculation back moves in the climatic cabinate, keeping humidity 100%, temperature is 20 degree, inoculate that maintenance relative moisture is 85% after 24 hours.Investigate after 7 days.The results are shown in Table 10
Table 10 pair cucumber anthracnose result of the test.(indoor)
Medicament Concentration (ppm) Preventive effect (%)
Compound (I) ?500 ?98.51
?250 ?89.94
?125 ?88.02
?62.5 ?69.83
?31.25 ?68.41
ZA-1963 ?500 ?93.20
?250 ?86.38
?125 ?80.94
?62.5 ?73.86
?31.25 ?63.24
Compound I slightly is better than contrasting medicament ZA-1963 to the preventive effect of cucumber anthracnose under same concentrations under greenhouse experiment

Claims (9)

1. methoxy-methyl acrylate compounds microbicide compositions is characterized in that comprising in the composition compound and isomer thereof with chemical structural formula (I):
Figure A0312088200021
2. microbicide compositions according to claim 1 is characterized in that the ratio that active ingredient (I) is occupied is 0.1%～99.0% weight in preparation.
3. according to claim 1,2 described microbicide compositions is characterized in that and active ingredient (I) can be mixed with emulsion, pulvis, wetting powder, colloidal suspending agent, granule.
4. according to the using method of the composition of above-mentioned arbitrary claim, it is characterized in that to use separately above-mentioned composition also can be re-dubbed binary or ternary mix preparation and use with bactericide, Insecticides (tech) ﹠ Herbicides (tech) or the plant growth regulator more than a kind or 2 kinds.
5. according to the using method of the composition of claim 4, it is characterized in that using on the crop control on various crops by multiple fungus-caused diseases such as Phycomycetes, Oomycete, Ascomycetes and deuteromycetes.
6. according to the using method of the composition of claim 4, it is characterized in that using and prevent and treat powdery mildew of wheat and barley, cucurbits powdery mildew, wheat rust, vegetables powdery mildew, fruit powdery mildew, flower class powdery mildew on the crop; Cucumber downy mildew, downy mildew of garpe; Cucumber anthracnose.
7. a fungicide compound is characterized in that compound is the compound and the isomer thereof of the formula (I) of claim 1
Figure A0312088200022
8. according to the preparation method of the compound of claim 7, it is characterized in that under alkali condition, making (II) compound and (III) compound reaction to obtain compound (I)
Wherein X is a leaving group among the III, and reaction in case of necessity can be carried out in the presence of solvent.
9. according to the preparation method of the compound of claim 7, it is characterized in that the process of reacting is as follows:
Wherein the X among the IV is a leaving group, and can add appropriate solvent when needed.
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