WO2004084632A1

WO2004084632A1 - Fungicides containing methoxy acrylic acid methyl ester compound

Info

Publication number: WO2004084632A1
Application number: PCT/CN2004/000226
Authority: WO
Inventors: Tianming Xu; Dinghua Chen; Xiaolin Kong; Weigang Zhu; Yunhong Zheng
Original assignee: Zhejiang Chemical Industry Research Institute
Priority date: 2003-03-25
Filing date: 2004-03-19
Publication date: 2004-10-07
Also published as: BRPI0409037A; AU2004224838A1; CN1456054A; ZA200508026B; TR200503847T1; CN1201657C

Abstract

The invention relates to fungicidal compositions which contain 2-(2-((2,5-dimethyl phenoxy)methyl phenyl))-3-methoxy acrylic acid methyl ester of fomula I and steroisomers thereof , their use-method, and active ingredient compound mentioned above and preparation thereof. Biological activity determination shows: compound I has high biological activity on preventing agricultural diseases caused by fungi, especially effective against powdery mildew, downy mildew and anthracnose.

Description

Methyl Acrylic Acrylate Compound Bactericide Technical Field

The invention relates to an ethoxylated methacrylate bactericidal agricultural fungicide, and further relates to an ethoxylated methacrylate acrylate compound having a high-efficiency bactericidal effect, a preparation method thereof, a bactericide composition thereof, and uses thereof.

Background technique

In US Pat. No. 4,914,128, a number of ethoxylated methacrylate compounds are disclosed, and the compounds therein have bactericidal activity.

The applicant has unexpectedly discovered that some compounds not specifically disclosed in its general structure have excellent fungicidal activity, and thus completed the present invention.

Methyloxy acrylate fungicides are highly effective agricultural fungicides derived from natural compounds through structural transformation. They are characterized by wide sterilization, low toxicity to other organisms, and good environmental compatibility. Many major pesticide companies in the world have carried out research in this area and found several methyloxyacrylate compounds with good market prospects. The market share of such fungicides is increasing, and it may replace triazole fungicides as the largest variety of agricultural fungicides.

Summary of the Invention

The present invention provides new ethoxylated methacrylate and its preparation method, and its bactericide composition and use. The chemical name of the methoxy methacrylate bactericide compound of the present invention is:

The structural formula of (E) -2- (2-((2,5-Difluorenylphenoxy) fluorenylphenyl))-3-methyloxyacrylate is:

I

The compounds of the invention can be prepared by the following methods:

Method 1 The response is as follows:

II III I

Compound I can be prepared by adding 2, 5 "difluorenylphenol of formula II and 2- ( ² -halomethylphenyl) -3-methoxymethylacrylate in formula III in a suitable solvent. It can be prepared by adding appropriate base and reacting at appropriate temperature and time. Among them, X leaving group such as halogen, and 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, 4A carbonate, and the like. The preferred base in the present invention is sodium carbonate or potassium carbonate.

The preferred temperature is 0-1 00. C.

Method 2 The reaction is as follows:

VI I

The method for preparing compound I in method two is as follows: In a suitable solvent, add 2,5-difluorenylphenol of formula II and a compound of formula IV, and then add the appropriate base and react at the appropriate temperature and time for the preparation.

V. Among them, X leaving group such as halogen, preferably chlorine, bromine or iodine. V in an appropriate solvent, then add an appropriate base, add an appropriate amount of methyl gallate, and react at an appropriate temperature and in an appropriate time to obtain

VI. VI In a suitable solvent, add a fluorenating reagent, such as dimethyl sulfate, iodopane, etc., and then add a suitable base, at the appropriate temperature and in a suitable time to obtain the compound I.

Among them, 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, and the like. The preferred base in the present invention is sodium carbonate or potassium carbonate. The preferred temperature is 0-100 ° C.

In preparing VI, the preferred base is sodium alkoxide or sodium hydride; the preferred solvent is diethyl ether or methanol. Preferred temperature Degrees are minus 5-100 C.

Among them, 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, and the like. The preferred base in the present invention is sodium carbonate or potassium carbonate.

The preferred temperature is 0-100 ° C.

Compound I of the present invention is an effective fungicide. Particularly suitable for controlling the following plant diseases: barley and wheat powdery mildew, vegetable powdery mildew, melons 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; diseases such as anthracnose on melons.

The invention also provides a bactericidal composition of a compound as defined above and a method for preparing the same.

The composition of the present invention preferably contains the active ingredient of formula (I) from 0.1 to 99.0% by weight. If desired, suitable carriers and surfactants can be added to the composition.

The composition of the present invention is prepared by mixing Compound I with at least one carrier. This composition may also contain other pesticide active ingredients.

The carrier of the present invention is a substance that satisfies the following conditions: it is formulated with an active ingredient to facilitate application to the site to be treated, such as plants, seeds, or soil; or it is convenient for storage, transportation, or handling. The carrier can be a solid or a liquid, and any carrier commonly used in formulating insecticidal and bactericidal compositions can be used.

Suitable solid carriers include natural and synthetic silicates, such as diatomaceous earth, talc, wollastonite, aluminum silicate (kaolin), montmorillonite, and mica; calcium carbonate, calcium sulfate, ammonium sulfate; synthetic silicic acid Calcium or aluminum silicate; elements such as carbon and sulfur; natural and synthetic resins such as benzofuran resins, polyvinyl and styrene polymers and copolymers; solid polychlorophenol; bitumen; waxes such as beeswax, paraffin wax.

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; petroleum fractions such as kerosene And mineral oils; chlorinated hydrocarbons such as carbon tetrachloride, perchloroethylene, and trichloroethane, and usually mixtures of these liquids are also suitable.

The pesticidal and germicidal composition is usually processed into a concentrate and used for transportation, and it is diluted by the user before application. The presence of a small amount of a surfactant carrier facilitates the dilution process. Thus, the composition according to the present invention preferably contains a surfactant. The surfactant can be an emulsifier, dispersant or wetting agent: it can be an ionic surfactant or a non-ionic surfactant. Such as: sodium salt or calcium salt of polyacrylic acid and lignin sulfonic acid;

Fatty acids or fatty amines or amides of 12 carbon atoms; condensates of ethylene oxide and or propylene oxide; glycol, sorbitol, sucrose or pentaerythritol fatty acid esters and these esters with ethylene oxide and / or propylene oxide Condensates of fatty alcohols or alkyl phenols such as p-octylphenol or condensates of p-octylphenol with ethylene oxide and or propylene oxide; sulfate or sulfonate salts of these condensation products; Alkali or alkaline earth metal salts of sulfuric acid or sulfonate of 10 carbon atoms, preferably sodium salts, such as sodium lauryl sulfate, secondary alkyl sulfate sodium ₅ sulfonated castor oil sodium salt, sodium alkylaryl sulfonate Such as dodecylbenzenesulfonic acid sodium salt.

Examples of the composition of the invention are wettable powders, powders, granules, emulsifiable concentrates, emulsions, suspension concentrates, aerosols and aerosols. Wettable powders usually contain 20-80% by weight of active ingredient, and usually contain 2-10% by weight of dispersant in addition to the solid inert carrier, and if necessary or added 0-10% by weight of stabilizers and other additives such as penetration Agent or adhesive. The powder can usually be shaped into a powder concentrate having a similar composition to a wettable powder, but with a dispersant, and further diluted with a solid carrier in the ground to obtain a composition usually containing 0.5 to 10% by weight of active ingredient. Granules are usually made in 10 and 100 mesh sizes and can be prepared by agglomeration or injection techniques. Generally, granules contain 0.1 to 80% by weight of active ingredients and 0 to 10% by weight of additives such as stabilizers, surfactants, sustained release agents, and the like. The so-called "flowable dry powder" consists of relatively small particles with a relatively high concentration of active ingredient. In addition to solvents, emulsifiable concentrates usually contain co-solvents when needed, 1-50% W / V active ingredient, 2-20 W / V emulsifier and 0-20 W / V other additives such as stabilizers, penetrants and corrosion Inhibitor. Suspension concentrates usually contain 10-80% by weight of active ingredients, 0.5-15% by weight of dispersant, and 0.1-10% by weight of other additives such as defoamers, corrosion inhibitors, stabilizers, penetrants and Adhesive.

Aqueous dispersants and emulsifiers, such as compositions obtained by diluting a wettable powder or concentrate according to the invention with water, are also included in the scope of the invention. The emulsion can be of two types: water-in-oil or oil-in-water.

By adding one or more other fungicides to the composition, it can be made more active than the compound (I) alone. In addition, other fungicides may have a synergistic effect on the fungicidal activity of the compound (I). Examples of fungicide compounds that may be included in the composition of the present invention: clotrimam, sterilant, azoxystrobin, tridemorpholine, chlorobenzene. Melidixol, flupronil, oxymethylene oxide, oxadiazole, zinc zem, mancozeb, formamide, dicarbendazol, isoxuron, methyl sclerotin, acetonitrile, hexazole Alcohol, Myclobutanil, Tebuconazole, Pentosalone, Cyproteril, Biguanide Acetate, Thiacarb, Cyclosporin, Flumorph, Fluoxazole, SSF-129, picoxys trobin, metrafenone> pyraclos trobin, resveratro, dimoxys trobin, UBF-307, BASF490F, ICIA5504, TH-164, RH7592, carbamuron, enazolol, fluoxuron, carbendazim, benomyl, benomyl , Triazolone, cycloconazole, ethicarb, methyltobrazine, terbendazim, butylmorpholine, metronidazole, metalaxyl, furasyl, benalaxyl, oxacarb, sulfacarb, Imidoxime, benzoxamidine, azoxystrobin, enosylmorpholine, seed dressing, dressing strength, propiconazole, chlorothalonil, diazine, copper sulfate, bacteriochlor, ethidium Mildew, etc.

Insecticides that can be combined with the compounds of the present invention to form a composition include: insecticides bromomester, diclofenac, methyl 1605, 1605, fenitrothion, diamnon, bupropion, chlorpyrifos, sharp Exterminator, Exterminator, Methomyl, Insecticidal Mono, Insecticidal Double, Badan, Avermectin, Permethrin, Cypermethrin, Permethrin, Stefluthrin, Cyfluthrin, Fenvalerate, Fluoride Diflubenzuron, diflubenzuron, diflubenzuron, pyraclostrobin, imidacloprid, dioxocarb, triazophos, quinacloprid, chlorfenuron, pyridaben, tetrabenazine, etc.

In order to obtain compounds that can control various fungal diseases at very small doses, the inventors have synthesized some of these compounds, which have broad-spectrum fungicidal activity and can be used to control crops from the class Algae and Oomycetes Diseases caused by a variety of fungi such as Zygomycetes and Deuteromycetes, and the high biological activity of this compound makes it possible to obtain good control effects at very low doses. These compounds show good biological activity against powdery mildew, downy mildew, and anthracnose, as well as controlling black pox and white rust of grapes.

The compounds provided by the present invention not only have high biological activity, but also are very friendly to the environment and have 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 agricultural fungicide.

detailed description

The present invention will be described in detail through the following specific examples. Unless otherwise specified, the parts in this application are by weight:

Synthesis Example:

At room temperature, 12.2g of 2,5-difluorenylphenol was added to a 500ml three-necked bottle containing 150ml of dry acetone, and then 13.8g of potassium carbonate was added, stirred at room temperature for 20 minutes, and then 28.5g (E ) Methyl-2- (2- (bromomethyl) phenyl) -3-methoxyoxyacrylate. The reaction was then refluxed for 3 hours to complete, filtered, and concentrated to obtain a crude product. Column chromatography was performed using a mixed solution of ethyl acetate and petroleum ether (1: 4) as the eluent to obtain Compound I 26. 08g as a white solid with a yield of 80 ° /. . Melting point: 108-110 ° C, 1 leg MR: 2. 235 (3H, s), 2. 279 (3Η, 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: Rei R spectra were recorded with CDC1 ₃ solvent. The abbreviations used in the experiments are as follows:

Rei R = nuclear magnetic resonance s = singlet d = doublet m = multimodal

Formulation Example 1

40 kg of the compound of the present invention, 53 kg of diatomaceous earth, 4 kg of C12-20 alcohol sulfate, and 3 kg of sodium dodecylbenzenesulfonate. The above ingredients are uniformly mixed and pulverized to obtain a 40% wettability of the active ingredient. powder.

Formulation Example 2

30 kg of the compound of the present invention, 33 kg of xylene, 30 kg of dimethylarsinamide, and 7 kg of polyoxyethylene alkylpropyl ether. The above ingredients are uniformly mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.

Formulation Example 3

The compound of the present invention is 10 kg, talc powder is 89 kg, and polyoxyethylene alkyl propyl ether is kg. The above ingredients are uniformly mixed and pulverized to obtain a powder containing 10% of the active ingredient.

Formulation Example 4

The compound of the present invention is 5 kg, clay is 73 kg, bentonite is 20 kg, sodium dioctyl thiosuccinate is 1 kg, and sodium phosphate is 1 kg. All the above ingredients are mixed and mixed thoroughly, and an appropriate amount of water is added. After further mixing, granulation and drying, granules containing 5% of the active ingredient are obtained.

Formulation Example 5

10 kg of the compound of the present invention, 4 kg of sodium ligninsulfonate, 1 kg of sodium dodecylbenzenesulfonate, 1 kg of xanthogenic acid, and 84 kg of water. To obtain a suspension agent containing 10% of the active ingredient.

Formulation Example 6

8 kg of the compound of the present invention, 50 kg of mancozeb, 30 kg of kaolin, 4 kg of sodium dodecylbenzenesulfonate, and 8 kg of sodium lignin sulfonate. After mixing the above components, the content of the mixture is obtained as follows: 58% wettable powder.

Formulation Example 7

1 kg of the compound of the present invention, 20 kg of triazolone, 64 kg of kaolin, 6 kg of sodium dodecyl benzoate, and 9 kg of sodium lignin sulfonate. Wettable powder with 21% content.

Examples of medicinal effects:

The compound of the present invention has good biological activity compared with existing fungicides, and can effectively prevent and treat diseases caused by fungi at very low doses. _{3 It} is particularly good for 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. Another one has a certain inhibitory effect on grapevine black pox and white rust.

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

The test agent was Compound I of the present invention (emulsion oil with a content of 5%) and six concentrations of 10 5 2. 5 1. 25 0. 625 0. 3125 ppm were set. Control ZA-1963 (ie Syngenta's icoxys trobin, which is a commercial compound in a similar patent) (5% emulsifiable concentrate) was set at six concentrations of 10 5, 2. 5 1. 25 0. 625 0. 3125 ppm. Control agent 20% triazolone EC, set 100 50 25ppm ₀ Select two potted cucumber plants growing from two leaves and one heart stage to spray the cucumber seedlings, spray for prevention test 24 hours after spraying, 24 hours after treatment test inoculation Spray medicine. After inoculation, young cucumbers were placed in an artificial climatic chamber for moisturizing culture, and the control effect was investigated 7 days later. The results are shown in Table 1:

Table 1 Test results of protection and treatment of cucumber powdery mildew:

Cucumber powdery mildew

Concentration (ppm)

Prevention effect (%) Treatment effect (%)

10 100 98. 89

5 100 97. 53

2. 5 97. 22 88. 89

Compound (I)

1. 25 90. 28 85. 71

0. 625 85. 31 64. 81

0. 315 63. 11 29. 63

10 98. 15 86. 11

5 88. 89 68. 52

2. 5 81. 75 36. 11

ZA-1963

1. 25 75. 60

0. 625 47. 63 8. 33

0. 315 41. 67 0. 0 „50 81. 25

25 45. 40

The results of protection and treatment tests show that: Compound I prevention is slightly better than treatment. 0. 625ppm prevention was 85. 31%, and treatment was 64. 81%. At the same time, it was found that the significant activity of the preventive and therapeutic effects of compound (I) was better than ZA-1963, especially the therapeutic effect. The biological activity of compound I is much better than triazolone.

Efficacy Example 2 Test for Protection and Treatment of Wheat Powdery Mildew (Indoor)

The test agent was Compound I of the present invention (emulsion oil with a content of 5%), and six concentrations of 25, 12.5.6.25, 3.125, 1.563, and 0.781 ppm were set. Control ZA-1963 (namely Syngenta's picoxys trobin, which is a compound commercialized in similar patents) (5% EC) is set to 25, 12. 5, 6. 25, 3. 125, 1. 563, 0. Six concentrations of 781ppm. Control agent 20% triazolone EC, set 100, 50, 25 ppm. The potted wheat growing up to the two-leaf one-heart stage was sprayed. The vaccine was inoculated 24 hours after spraying in the preventive test, and sprayed 24 hours after seeding in the treatment test. After the inoculation, the wheat was placed in an artificial climate chamber for moisturizing culture, and the control effect was investigated 7 days later. The results are shown in Table 2

Table 2 Test results of protection and treatment of powdery mildew

Wheat powdery mildew

Concentration (ppm)

Preventive effect (>> / ») Treatment effect (

25 100 100

12. 5 100 100

6. 25 100 100

Compound (I)

3. 125 100 100

1. 563 98. 33 97. 33

0. 781 87. 43 84. 13

25 100 99. 77

12. 5 99. 60

6. 25 91. 30 82, 95

ZA-1963

3. 125 93. 61 73. 15

1. 563 78. 18 71. 97

0. 781 53. 05 38. 97

Triazolone 100 50

25

The results of the protection and treatment tests showed that the obvious activity of the preventive and therapeutic effects of Compound I was found to be better than that of ZA-1963, and the therapeutic effect was more obvious. The biological activity of compound I is much better than triazolone. Efficacy Example 3 Simulated Field Test on Wheat Powdery Mildew

Compound (I) concentration was 50, 25, 12. 5, 6. 25, 3. 125ppm, a process control agent ZA- 1963 the same concentration of compound I, treatment concentration triadimefon of 100, 50, 25ppm ₀ to Potted wheat was cultivated to the 4-5 leaf stage, and allowed to naturally develop to the middle stage. Foliar spray treatment was performed at the concentration set above, and the control effect was investigated after 10 days. The results are shown in Table 3.

Table 3 Simulated field tests on powdery mildew of wheat

The results of simulated field tests showed that Compound I still showed a high control effect on pot wheat when it was spontaneous to mid-term, and its control effect was better than the control agents ZA-1963 and triazolone.

Example of efficacy 4 Duration test

The treatment concentration of Compound I and the control agent ZA-1963 was 50, 25 mg / l, and the test object was wheat powdery mildew. Spray the two real leaves of potted wheat when they are flat, inoculate the powdery mildew of wheat 24 hours after spraying, move the inoculated wheat to the greenhouse for moisturizing culture, and investigate the prevention effect at 7, 10, 15, 20, 25, and 30 days after treatment . The results are shown in Table 4. Table 4 Validity period test results

The duration test showed that the duration of Compound I was slightly longer than that of ZA-1963 under artificial greenhouse inoculation.

Efficacy Example 5 Control Effect on Pumpkin Powdery Mildew (Field)

A field trial of pumpkin powdery mildew control in June 2002 was conducted in a greenhouse in a modern agricultural park in Shaoxing, Zhejiang.

Compound I (10% aqueous suspension) was set at four concentrations of 50, 25, 12.5, and 6.25ppm, and the control agent was 20% fentanin EC and the concentration was set at 100ppm. Another set of water control. Each treatment was repeated 4 times. Investigation was made 7 days after application. The results are shown in Table 5. Table 5 Results of Control Tests (Field) on Pumpkin Powdery Mildew

Note: The CK prevention effect column is the added value of sick fingers.

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

Effectiveness example 6 Control test for cucumber powdery mildew (field)

A field trial of cucumber powdery mildew in June 2002 was conducted in a greenhouse in a modern agricultural park in Shaoxing, Zhejiang. Compound I (10% aqueous suspension) was set at four concentrations of 50, 25, 12. 5 and 6. 25 ppm, and the control agent was 20% fentanin EC and the concentration was set at 100 ppm. Another set of water control. Each treatment was repeated 4 times. Investigation 7 days after application. The results are shown in Table 6.

Table 6 Results of field tests on cucumber powdery mildew

Note: The CK prevention effect column is the added value of sick fingers.

It can be seen from Table 6 that Compound I has a high activity on cucumber white powder at 6.25 ppm, which is significantly better than that of the control agent Fenning.

Efficacy Example 7 Compound (I) Test for Cucumber Downy Mildew (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 two potted cucumber plants that grow to one leaf and one heart period to spray the cucumber seedlings. Spray for 24 hours after spraying for prevention test and spray for 24 hours after treatment test. After inoculation, young cucumbers were placed in an artificial climate chamber for moisturizing culture, and the control effect was investigated after 7 days. The results are shown in Table 7

Table 7 Results of laboratory test on indoor downy mildew (indoor) Concentration (ppm) Control effectiveness (%)

Compound (I) 100 100

50 100

25 100

12. 5 97. 18

6. 25 91. 55

3. 125 77. 46

100 91. 55 50 60. 56

25 46. 48

12. 5 40. 84

6. 25 26. 76

3. 125 9. 86

Phase T 500 70. 11 Under greenhouse conditions, the control effect of compound I on cucumber downy mildew was significantly better than the control agent ZA-1963 at the same concentration, and it was significantly better than metalaxyl. Efficacy Example 8 Control effect on grape downy mildew (field)

A field trial to control grape downy mildew was conducted in July 2002 at the Agricultural Science and Technology Demonstration Farm in Shiqiao Township, Dangtu County, Ma'anshan City, Anwei Province.

Compound I (5% emulsifiable concentrate) was set at five concentrations of 200, 100, 50, 25, 12.5 ppm, and the control agent was 72% DuPont Crewe wettable powder at a concentration of 1000 ppm. A blank control was set up, and each treatment was repeated 4 times. Investigation after spraying the next day. The results are shown in Table 8.

Table 8 Results of control experiments (field) on grape downy mildew

From the results, it can be seen that Compound I is equivalent to 200 ppm of Cremonol at a control level of 200 ppm in the control of Plasmopara viticola.

Effectiveness Example 9 Control effect on cucumber downy mildew (field)

Field trial of cucumber downy mildew control in July 2002 in Shiqiao Township, Dangtu County, Maanshan City, Anwei Province Industry technology demonstration site.

Compound I (5% emulsifiable concentrate) was set at five concentrations of 200, 100, 50, 25, 12. 5 ppm.

The 72% DuPont Crewe wettable powder is set at 1000 ppm. A blank control was set up, and each treatment was repeated 4 times. Investigation 7 days after spraying. The results are shown in Table 9

Table 9 Results of field trials of cucumber downy mildew

It can be seen from the results that the compound I in controlling cucumber downy mildew at 200 ppm is equivalent to the control drug Kelu lOOppm. Effectiveness Example 10 Test on Cucumber Anthrax (Indoor)

The treatment concentration of compound I and the control agent ZA-1963 was 500, 250, 125, 62.5, 31. 25 ppm. The test object was cucumber anthracnose. The potted cucumber seedlings were sprayed when they grew to a true leaf stage. The anthracnose spore suspension was inoculated after spraying for 24 hours. After the inoculation, they were moved to an artificial climate chamber and the humidity was maintained at 100%. The relative humidity should be 85% after 24 hours of inoculation. Investigation was conducted after 7 days. The results are shown in Table 10.

Table 10 Test results of cucumber anthracnose (indoor) Concentration (ppm) Control effect (%)

Compound (I) 500 98. 51

250 89. 94

125 88. 02

Under greenhouse conditions, the control effect of compound I on cucumber anthracnose is slightly better than the control drug at the same concentration -1963

Claims

Claim

1. A fungicide composition of methyl methacrylate compound, characterized in that the composition contains a compound having chemical structural formula (I) and isomers thereof:

2. The fungicide composition according to claim 1, characterized in that the proportion of the active ingredient (I) in the preparation is from 0.1 to 99.0% by weight.

3. The fungicide composition according to claim 1, wherein the active ingredient (I) can be formulated into an emulsion, a powder, a wettable powder, a suspension, and a granule.

4. A method for using a composition according to any one of the preceding claims, characterized in that the above composition can be used alone or in combination with one or two or more fungicides, insecticides, herbicides or plant growth regulators Application as a binary or ternary mixed preparation.

5. The method of using the composition according to claim 4, characterized in that it is applied to crops to prevent and treat diseases caused by various fungi such as Algae, Oomycetes, Zygomycetes, and Deuteromycetes on various crops .

6. The method of using the composition according to claim 4, characterized in that it is used to control wheat powdery mildew, melons powdery mildew, wheat powdery mildew, vegetable powdery mildew, fruit powdery mildew, and powdery mildew on crops; Mildew, grape downy mildew; cucumber anthracnose.

7. A fungicide compound, characterized in that the compound is a compound of the formula (I) and its isomers according to claim 1.

The method for preparing a compound according to claim 7, characterized in that the compound (I) is reacted with the compound (III) under basic conditions to obtain the compound (I)

II III I

Wherein X is a leaving group, and the reaction may be performed in the presence of a solvent if necessary.

9. A method for preparing a compound according to claim 7, characterized in that the reaction process is as follows: