CN1201657C - Methoxy methyl acrylate compounds as bactericidal agent - Google Patents

Abstract

The invention relates to a fungicide containing 2-(2-((2,5-dimethylphenoxy)methylphenyl))-3-methoxymethyl acrylate and its stereoisomers shown in structural formula I Compositions of compounds, methods of use thereof, and compounds of the above active ingredients and methods of preparation thereof. The biological activity test shows that the compound I has high biological activity for the prevention and treatment of diseases produced by fungi in agriculture, and has special effects for the prevention and treatment of powdery mildew, downy mildew and charcoal gnat.

Description

Methyl methoxyacrylate compound fungicide

Technical field of the present invention

The invention relates to a methyl methoxyacrylate agricultural fungicide. The present invention further relates to a methyl methoxyacrylate compound with high-efficiency bactericidal effect, its preparation method, its bactericide composition and its application.

In order to obtain compounds that can control various fungal diseases at a very small dose, the inventors of the present invention have synthesized some of these compounds. , Ascomycetes and Deuteromycetes and other fungi, and because this compound has high biological activity, it can obtain good control effect at a very low dose. This kind of compound not only shows good biological activity against powdery mildew, downy mildew and anthracnose, but also has control effect on grape black pox and grape white rust.

The compound provided by the invention not only has high biological activity, but also is very friendly to the environment and has no pollution to the environment. The compound provided by the invention not only has high biological activity, but also has low production cost compared with similar products in the world, and is a very promising new variety of agricultural fungicide.

Background technique

Some methyl methoxyacrylate compounds are disclosed in US 4,914,128 patent application, and it is disclosed that the compounds have fungicidal activity.

The applicant unexpectedly found that some undisclosed compounds in the general structure have excellent fungicidal activity, and thus completed the present invention.

Methyl methoxyacrylate fungicides are high-efficiency agricultural fungicides derived from natural compounds through structural modification. They are characterized by wide sterilization, low toxicity to other organisms, and good environmental compatibility. Many large pesticide companies in the world have conducted research in this area and discovered several methyl methoxyacrylate compounds with good market prospects. The market share of this type of fungicide is increasing, and it may replace triazole fungicides to become the largest variety of agricultural fungicides.

Summary of the invention

The invention provides a new methyl methoxyacrylate compound, a preparation method thereof, and a fungicide composition and use thereof. The chemical name of methyl methoxyacrylate bactericide compound of the present invention is:

(E)-2-(2-((2,5-dimethylphenoxy)methylphenyl))-3-methoxymethyl acrylate

The structural formula is:

Compounds of the present invention can be prepared by the following methods:

Method 1 reacts as follows:

Compound I can be prepared by adding 2,5-dimethylphenol of formula II and methyl 2-(2-halomethylphenyl)-3-methoxyacrylate of formula III in a suitable solvent , then add an appropriate base, react at an appropriate temperature and within an appropriate time. Wherein the leaving group X in III is such as halogen, preferably chlorine, bromine or iodine.

Preferred solvents are acetone or tetrahydrofuran.

The bases include organic bases and inorganic bases: organic bases include triethylamine, pyridine, etc.; inorganic bases include sodium hydroxide, potassium hydroxide, sodium hydride, sodium carbonate, potassium carbonate, etc. The preferred base of the present invention is sodium carbonate or potassium carbonate.

The preferred temperature is 0 to 100°C.

Method 2 The reaction is as follows:

Method 2 The process of preparing compound I is: in an appropriate solvent, add 2,5-dimethylphenol of formula II and compound of formula IV, then add an appropriate base, and react at an appropriate temperature and within an appropriate time to obtain V . Wherein the leaving group X in IV is such as halogen, preferably chlorine, bromine or iodine. V is in an appropriate solvent, then add an appropriate base, add an appropriate amount of methyl formate, and react at an appropriate temperature and within an appropriate time to obtain VI. VI In an appropriate solvent, add a methylating agent, such as dimethyl sulfate, methyl iodide, etc., and then add an appropriate base, and react at an appropriate temperature and for an appropriate time to obtain compound I.

Wherein when preparing V: the preferred solvent is acetone or tetrahydrofuran.

The bases include organic bases and inorganic bases: organic bases include triethylamine, pyridine, etc.; inorganic bases include sodium hydroxide, potassium hydroxide, sodium hydride, sodium carbonate, potassium carbonate, etc. The preferred base of the present invention is sodium carbonate or potassium carbonate.

The preferred temperature is 0 to 100°C.

When preparing VI, the preferred base is sodium methoxide or sodium hydride, etc.; the preferred solvent is ether or methanol. The preferred temperature is minus 5 to 100°C.

Wherein when preparing I: the preferred solvent is acetone or tetrahydrofuran.

The bases include organic bases and inorganic bases: organic bases include triethylamine, pyridine, etc.; inorganic bases include sodium hydroxide, potassium hydroxide, sodium hydride, sodium carbonate, potassium carbonate, etc. The preferred base of the present invention is sodium carbonate or potassium carbonate.

The preferred temperature is 0 to 100°C.

The compounds I according to the invention are effective fungicides. Especially suitable for the control of the following plant diseases:

Barley and wheat powdery mildew, vegetable powdery mildew, melon powdery mildew, fruit tree powdery mildew, grape powdery mildew, strawberry powdery mildew and flower powdery mildew; wheat and barley stripe rust, leaf rust and other rust diseases.

Cucumber downy mildew, grape downy mildew; anthracnose and other diseases on melons.

The present invention also provides a fungicidal composition of the compound as defined above and a preparation method thereof.

The composition of the present invention preferably contains from 0.1 to 99.0% by weight of the active ingredient of formula (I). Suitable carriers and surfactant ingredients can be added to the composition as desired.

The composition of the invention is prepared by mixing compound I and at least one carrier. Such compositions may also contain other pesticidally active ingredients.

The carrier system of the present invention is a substance that satisfies the following conditions: it can be conveniently applied to the site to be treated after being formulated with active ingredients, such as plants, seeds or soil; or it is convenient for storage, transportation or handling. The carrier can be solid or liquid, and any carrier commonly used in formulating insecticidal and fungicidal compositions can be used.

Suitable solid carriers include natural and synthetic silicates such as diatomaceous earth, talc, attapulgite, aluminum silicates (kaolins), montmorillonite and mica; calcium carbonate, calcium sulfate, ammonium sulfate; synthetic oxidized silicic acid Calcium or aluminum silicates; elements such as carbon and sulfur; natural and synthetic resins such as benzofuran resins, polyvinyl chloride and styrene polymers and copolymers; solid polychlorinated phenols; bitumen; waxes such as beeswax, paraffin.

Suitable liquid carriers include water; alcohols such as isopropanol and ethanol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ethers; aromatic hydrocarbons such as benzene, toluene, and xylene; and mineral oil; chlorinated hydrocarbons such as carbon tetrachloride, perchlorethylene, and trichloroethane; often, mixtures of these liquids are also suitable.

Insecticidal and fungicidal compositions are usually processed and transported in the form of concentrates, which are diluted by the user before application. The presence of a small amount of surfactant carrier aids in the dilution process. Thus, in the composition according to the present invention, a surfactant is preferably contained.

A surfactant can be an emulsifying agent, a dispersing agent or a wetting agent: it can be an ionic or a nonionic surfactant. Such as: sodium or calcium salts of polyacrylic acid and lignosulfonic acid; fatty acids or fatty amines or amides with at least 12 carbon atoms in the molecule; condensates of ethylene oxide and or propylene oxide; glycol, sorbitol , sucrose or pentaerythritol fatty acid esters and condensation products of these esters with ethylene oxide and or propylene oxide; fatty alcohols or alkylphenols such as p-octylphenol or p-octylphenol with ethylene oxide and or propylene oxide condensates; sulfate or sulfonate salts of these condensation products; alkali metal or alkaline earth metal salts, preferably sodium salts, of sulfuric acid or sulfonate containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulfate, secondary sulfate Sodium alkyl esters, sodium sulfonated castor oil, sodium alkylaryl sulfonates such as sodium dodecylbenzenesulfonate.

Examples of compositions according to the invention are wettable powders, dusts, granules, emulsifiable concentrates, emulsions, suspension concentrates, aerosols and aerosols. Wettable powders usually contain 20-80% by weight of active ingredients, and usually in addition to solid inert carriers, also contain 2-10% by weight of dispersants, and if necessary, or add 0-10% by weight of stabilizers and or other additives such as osmotic agent or adhesive. Dusts can generally be formed as powder concentrates having a composition similar to wettable powders but with a dispersing agent, which can be further diluted in the field with a solid carrier to give a composition generally containing 0.5 to 10% by weight of active ingredient. Granules are usually produced in 10 and 100 mesh sizes and can be prepared by agglomeration or injection techniques. Usually, granules contain 0.1-80% by weight of active ingredients and 0-10% by weight of additives such as stabilizers, surfactants, slow-release agents and the like. So-called "dry flowable powders" consist of relatively small granules having a relatively high concentration of active ingredient. Emulsifiable concentrates usually contain co-solvents, 1-50% W/V active ingredients, 2-20% W/V emulsifiers and 0-20% W/V other additives such as stabilizers, osmotic agents and corrosion inhibitors. Suspension concentrates usually contain 10-80% by weight of active ingredients, 0.5-15% by weight of dispersants, and 0.1-10% by weight of other additives such as defoamers, corrosion inhibitors, stabilizers, penetrating agents and adhesives.

Aqueous dispersants and emulsifiers, such as compositions obtained by diluting the wettable powders or concentrates according to the invention with water, are also within the scope of the invention. Said emulsions may be of the water-in-oil or oil-in-water type.

By adding one or more other fungicides to the composition, it can have wider activity than compound (I) alone. In addition, other fungicides may have a synergistic effect on the fungicidal activity of compound (I). Among the examples of fungicide compounds that may be included in the composition of the present invention: Captan, Folpet, Pyrimethanil, Tridemorph, Chlorpyrimidol, Fludioxonil, Oxidone, Fefeconazole , Zinc, mancozeb, thiram, captafol, iprodione, proclozolid, proclozolid, hexaconazole, myclobutanil, tebuconazole, penbicolon, cyprodione Cyanide, biguanide octyl acetate, thiocarb, cycloheximide, flumorph, fluoxazole, SSF-129, picoxystrobin, metrafenone, pyraclostrobin, resveratro, dimoxystrobin, UBF-307, BASF490F, ICIA5504, TH-164, RH7592, Diprodicarb, Diniconazole, Fluoride, Carbendazim, Benomyl, Triadimefon, Cycloconazole, Dimethocarb, Thioprazine-methyl, Tufenxiao, Penfenmorph, Downy mildew Carboxyl, metalaxyl, furalaxyl, benalaxyl, oxamide, sulfonylcarb, pymetroxime, fenpropidin, azoxystrobin, dimethomorph, seed dressing, seed dressing strong, propiconazole, Chlorothalonil, diazine, copper sulfate, bacteriostat, fosfo-aluminum, hymexazol, etc.

Insecticides that can be mixed with the compounds of the present invention to form compositions include: insecticides bromofen, dicofol, methyl 1605, 1605, fenitrothion, diananon, carbosulfan, chlorpyrifos, and regent . .

Detailed ways

The present invention is described in detail by the following specific examples, unless otherwise specified parts in the application are by weight :

Synthetic Example:

At room temperature, add 12.2g of 2,5-xylenol to a 500ml three-neck flask filled with 150ml of dry acetone, then add 13.8g of potassium carbonate, stir at room temperature for 20 minutes, then slowly add 28.5g of (E)-2- Methyl (2-(bromomethyl)phenyl)-3-methoxyacrylate. Then the reflux reaction was completed for 3 hours, filtered and concentrated to obtain a crude product. Column chromatography was performed using a mixture of ethyl acetate and petroleum ether (1:4) as the eluent to obtain 26.08 g of compound I as a white solid with a yield of 80%. Melting point: 108～110℃

¹ H NMR: 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)

Note: ¹ HNMR spectra were recorded with CDCl ₃ solvent. The abbreviations used in the experiments are as follows:

NMR = nuclear magnetic resonance s = singlet d = doublet m = multimodal

Formulation example

Formulation Example 1

40 kilograms of compounds of the present invention, 53 kilograms of diatomite, 4 kilograms of C12-20 alcohol sulfate, 3 kilograms of sodium dodecylbenzenesulfonate, the above ingredients are uniformly mixed, pulverized, and a wettable compound containing 40% of active ingredients is obtained. powder.

Formulation Example 2

30 kg of compound of the present invention, 33 kg of xylene, 30 kg of dimethylformamide, and 7 kg of polyoxyethylene alkyl propyl ether are uniformly mixed and dissolved to obtain an emulsion containing 30% active ingredient.

Formulation Example 3

10 kg of the compound of the present invention, 89 kg of talcum powder, and kg of polyoxyethylene alkyl propyl ether were uniformly mixed and pulverized to obtain a powder containing 10% of the active ingredient.

Formulation Example 4

5 kg of the compound of the present invention, 73 kg of clay, 20 kg of bentonite, 1 kg of sodium dioctyl thiosuccinate, and 1 kg of sodium phosphate. The above ingredients are uniformly mixed, fully pulverized, and an appropriate amount of water is added. Then fully mix, granulate, and dry to obtain granules containing 5% active ingredient.

Formulation Example 5

10 kg of compound of the present invention, 4 kg of sodium lignin sulfonate, 1 kg of sodium dodecylbenzene sulfonate, 1 kg of xanthic acid, 84 kg of water, uniformly mix the above ingredients, and wet grind until the particle size is below 1 micron , to obtain a suspension containing 10% active ingredient.

Formulation Example 6

8 kilograms of compounds of the present invention, 50 kilograms of mancozeb, 30 kilograms of kaolin, 4 kilograms of sodium dodecylbenzenesulfonate, and 8 kilograms of sodium lignosulfonate are mixed with the above-mentioned components, and after fully pulverizing, the content of the mixed agent is: 58% wettable powder.

Formulation Example 7

1 kilogram of compound of the present invention, 20 kilograms of triadimefon, 64 kilograms of kaolin, 6 kilograms of sodium dodecylbenzenesulfonate, 9 kilograms of sodium lignosulfonate, the above ingredients are uniformly mixed, after fully pulverizing, the mixed content is 21 % wettable powder.

Medicinal effect embodiment:

Compared with the existing fungicides, the compound of the present invention has good biological activity, can prevent and treat diseases caused by fungi well at very low doses, and is particularly effective against powdery mildew, rust, downy mildew and anthracnose Effect. Such as wheat, barley powdery mildew, cucumber powdery mildew, pumpkin powdery mildew, strawberry powdery mildew, grape powdery mildew, wheat, barley rust, grape downy mildew, cucumber downy mildew, cucumber anthracnose. The other also has a certain inhibitory effect on grape black pox and white rust.

Efficacy Example 1: Prevention and Treatment of Cucumber Powdery Mildew Protection and Therapeutic Effect Test (Indoor)

The test agent is compound I of the present invention (5% emulsifiable concentrate) with six concentrations of 10, 5, 2.5, 1.25, 0.625, and 0.3125 ppm. Control ZA-1963 (namely picoxystrobin from Syngenta Company, which is a commercially available compound in a similar patent) (5% emulsifiable concentrate) has six concentrations of 10, 5, 2.5, 1.25, 0.625, 0.3125 ppm. The control drug 20% triadimefon EC was set at 100, 50, and 25 ppm. Select the healthy cucumber seedlings with two flat true leaves growing to the stage of two leaves and one heart for spraying, inoculate 24 hours after the spraying for the prevention test, and spray for 24 hours after the inoculation for the treatment test. After inoculation, the young cucumbers were placed in an artificial climate box for moisturizing cultivation, and the control effect was investigated after 7 days. The results are shown in Table 1:

Table 1 Cucumber powdery mildew protective and therapeutic effect test results: potion Concentration (ppm) Cucumber powdery mildew Preventive effect (%) treatment effect(%) 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 Triadimefon 100 100 50 81.25 25 45.40

The results of the protection and treatment test showed that the prevention of compound I was slightly better than the treatment. 0.625ppm is 85.31% for prevention and 64.81% for treatment. At the same time, it was found that compound (I) had better preventive and therapeutic effects than ZA-1963, especially the therapeutic effect. The biological activity of compound I is far better than that of triadimefon.

Efficacy Example 2 Prevention and Treatment of Wheat Powdery Mildew Protection and Therapeutic Effect Test (Indoor)

The test agent is compound I of the present invention (5% emulsifiable concentrate) with six concentrations of 25, 12.5, 6.25, 3.125, 1.563, and 0.781 ppm. Control ZA-1963 (namely picoxystrobin from Syngenta Company, which is commercialized compound in similar patent) (5% emulsifiable concentrate) has six concentrations of 25, 12.5, 6.25, 3.125, 1.563, 0.781ppm. The control drug 20% triadimefon EC was set at 100, 50, and 25 ppm. Potted wheat grown to the 2-leaf one-heart stage was selected for spraying, inoculated 24 hours after spraying in the prevention test, and sprayed 24 hours after inoculation in the treatment test. After inoculation, the wheat was transferred to an artificial climate box for moisture cultivation, and the control effect was investigated 7 days later. The results are shown in Table 2

Table 2 The test results of protective and therapeutic effects on powdery mildew potion Concentration (ppm) wheat powdery mildew Preventive effect (%) treatment effect(%) 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 Triadimefon 100 50 25

The results of the protection and treatment test showed that the prevention and treatment effect of compound I was found to be better than that of ZA-1963, and the treatment effect was more obvious. The biological activity of compound I is far better than that of triadimefon.

Efficacy Example 3 Simulated Field Test on Wheat Powdery Mildew

The treatment concentration of compound (I) was 50, 25, 12.5, 6.25, 3.125ppm, the treatment concentration of the control agent ZA-1963 was the same as that of compound I, and the treatment concentration of triadimefon was 100, 50, 25ppm. Cultivate the potted wheat to the 4-5 leaf stage, let it naturally develop to the middle stage, spray the leaves according to the concentration set above, and investigate the control effect after 10 days. The results are shown in Table 3

Table 3 simulated field experiments on wheat powdery mildew potion Concentration (mg/l) Anti-efficacy (%) 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 Triadimefon 100 64.93 50 13.85

The simulated field test results showed that compound I still exhibited a high control effect on potted wheat when it was applied at the mid-stage of natural onset, and the control effect was better than that of the control agents ZA-1963 and triadimefon.

Drug effect embodiment 4 duration test

The treatment concentrations of compound I and control agent ZA-1963 were 50 and 25 mg/l, and the test object was wheat powdery mildew. Spray when the two true leaves of potted wheat are flat, inoculate powdery mildew of wheat 24 hours after spraying, move the inoculated wheat to the greenhouse for moisture cultivation, and investigate the control effect 7, 10, 15, 20, 25, and 30 days after treatment . The results are shown in Table 4

Table 4 persistence test result potion Concentration mg/l Anti-efficacy (%) 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 persistence period test showed that: under the conditions of artificial inoculation in the greenhouse, the persistence period of compound I was slightly longer than that of ZA-1963.

Control effect test (field) to pumpkin powdery mildew of drug effect embodiment 5

The field test of pumpkin powdery mildew control effect was carried out in June 2002 in the greenhouse of Modern Agricultural Park in Shaoxing City, Zhejiang Province.

Compound I (10% aqueous suspension) was set at four concentrations of 50, 25, 12.5, and 6.25 ppm, and the control drug was 20% fenrustin EC at a concentration of 100 ppm. In addition, clear water was used as a control. Each treatment was repeated 4 times. Survey after 7 days of application. The results are shown in Table 5

Table 5 is the control effect test (field) result to pumpkin powdery mildew potion Concentration (ppm) Disease index disease index increase Anti-efficacy (%) 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 Prussine 200 20 7.25 72.7 CK 44.25 27.5 27.5

Note: The CK prevention effect column is the added value of the disease index.

It can be seen from Table 5 that the compound has a high activity on pumpkin white powder at 6.25ppm, which is obviously better than that of the contrast agent Fenxiening.

Control effect test (field) to cucumber powdery mildew of drug effect embodiment 6

The field test of controlling cucumber powdery mildew was carried out in June 2002 in a greenhouse in the modern agricultural park of Shaoxing City, Zhejiang Province.

Compound I (10% aqueous suspension) was set at four concentrations of 50, 25, 12.5, and 6.25 ppm, and the control drug was 20% fenrustin EC at a concentration of 100 ppm. In addition, clear water was used as a control. Each treatment was repeated 4 times. Survey after 7 days of application. The results are shown in Table 6

Table 6 is the control effect test (field) result to cucumber powdery mildew potion Concentration (ppm) Disease index disease index increase Anti-efficacy (%) 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 Prussine 200 37.25 11 68.8 CK 59.5 35.25 35.25

Note: The CK prevention effect column is the added value of the disease index.

As can be seen from Table 6: compound I has very high activity to cucumber white powder at 6.25ppm, which is obviously better than the contrast agent fenxining.

Drug effect embodiment 7 compound (I) is to cucumber downy mildew control effect test (indoor)

The treatment concentration of compound I was 100, 50, 25, 12.5, 6.25 ppm, the treatment concentration of the control agent ZA-1963 was the same as that of compound I, and the treatment concentration of metalaxyl was 500 ppm. Select the healthy cucumber seedlings with two flat true leaves growing to the stage of two leaves and one heart for spraying, inoculate 24 hours after the spraying for the prevention test, and spray for 24 hours after the inoculation for the treatment test. After inoculation, the young cucumbers were transplanted into an artificial climate box for moisturizing cultivation, and the control effect was investigated after 7 days. The results are shown in Table 7

Table 7 Control effect test (indoor) result to cucumber downy mildew potion Concentration (ppm) Anti-efficacy (%) 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

Under greenhouse conditions, the control effect of compound I on cucumber downy mildew was significantly better than that of the control agent ZA-1963 at the same concentration, and significantly better than metalaxyl.

Control effect test (field) to grape downy mildew of drug effect embodiment 8

The field test of grape downy mildew control was carried out in July 2002 in the agricultural science and technology demonstration field of Shiqiao Township, Dangtu County, Ma'anshan City, Anhui Province.

Five concentrations of compound I (5% emulsifiable concentrate) were set at 200, 100, 50, 25, and 12.5 ppm, and the concentration of the control drug 72% Dupont Clew WP was set at 1000 ppm. A blank control was also set up, and each treatment was repeated 4 times. Survey after 7 days of spraying. The results are shown in Table 8

Table 8 is the control effect test (field) result to grape downy mildew potion Concentration (ppm) Pre-drug base disease index Anti-efficacy (%) 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 Clew 1000 1.55 1.68 82.49 CK 1.89 11.70

As can be seen from the results, compound I is comparable to the control drug Kelu 1000ppm at 200ppm in the prevention and treatment of grape downy mildew. Control effect test (field) to cucumber downy mildew of drug effect embodiment 9

The field experiment of controlling cucumber downy mildew was carried out in July 2002 in the agricultural science and technology demonstration field of Shiqiao Township, Dangtu County, Ma'anshan City, Anhui Province.

Compound I (5% emulsifiable concentrate) was set at five concentrations of 200, 100, 50, 25, and 12.5 ppm, and the control drug 72% DuPont Kelu WP was set at 1000 ppm. A blank control was also set up, and each treatment was repeated 4 times. Survey after 7 days of spraying. The results are shown in Table 9

Table 9 is the control effect test (field) result to cucumber downy mildew potion Concentration (ppm) Pre-drug base disease index Anti-efficacy (%) 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 Clew 1000 0.93 1.13 85.33 CK 0.78 6.48

As can be seen from the results, Compound I is comparable to the control drug Kelu 1000ppm at 200ppm in the control of cucumber downy mildew.

Efficacy Example 10 Anti-effect Test on Cucumber Anthracnose (Indoor)

The treatment concentrations of compound I and control agent ZA-1963 were 500, 250, 125, 62.5, 31.25 ppm. The test object is cucumber anthracnose. Potted cucumber seedlings are sprayed when they grow to a true leaf stage. 24 hours after spraying, they are inoculated with anthracnose spore suspension. After inoculation, they are moved into an artificial climate box, and the humidity is kept at 100% and the temperature is 20 degrees. , maintain a relative humidity of 85% 24 hours after inoculation. Survey after 7 days. The results are shown in Table 10

Table 10 Test results for cucumber anthracnose. (indoor) potion Concentration (ppm) Anti-efficacy (%) 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

The control effect of compound I on cucumber anthracnose was slightly better than that of the control agent ZA-1963 at the same concentration under greenhouse conditions

Claims (9)

1. a methyl methoxyacrylate compound bactericide composition is characterized in that comprising the compound with chemical structural formula (I) and isomer thereof in the composition:

2. The fungicide composition according to claim 1, characterized in that the proportion of the active ingredient (I) in the preparation is 0.1% to 99.0% by weight. 3. according to claim 1 and 2 described fungicide composition, it is characterized in that active ingredient (I) can be mixed with emulsion, powder, wettable powder, colloidal suspension, granule. 4. According to the use method of the composition according to any one of the above claims, it is characterized in that the above composition can be used alone or compounded with one or more fungicides, insecticides, herbicides or plant growth regulators It can be used as a binary or ternary mixed preparation. 5. according to the using method of the composition of claim 4, it is characterized in that being used on crops to prevent and treat the disease caused by various fungi such as Phycomycetes, Oomycetes, Ascomycetes and Deuteromycetes. . 6. according to the use method of the composition of claim 4, it is characterized in that being used on crops to control wheat powdery mildew, melon powdery mildew, wheat rust, vegetable powdery mildew, fruit powdery mildew, flower powdery mildew; Cucumber frost Mildew, grape downy mildew; cucumber anthracnose. 7. A fungicide compound, characterized in that the compound is a compound of the formula (I) of claim 1 and an isomer thereof

8. according to the preparation method of the compound of claim 7, it is characterized in that making (II) compound and (III) compound reaction obtain compound (I) under alkaline condition Where X in III is a leaving group, the reaction can be carried out in the presence of a solvent if necessary. 9. according to the preparation method of the compound of claim 7, it is characterized in that the process of reaction is as follows: Wherein X in IV is a leaving group, and an appropriate solvent can be added if necessary.