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CN1907024A - Methoxyl group displacement methyl acrylate compound bactericidal agent - Google Patents

Methoxyl group displacement methyl acrylate compound bactericidal agent Download PDF

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Publication number
CN1907024A
CN1907024A CNA2005100602717A CN200510060271A CN1907024A CN 1907024 A CN1907024 A CN 1907024A CN A2005100602717 A CNA2005100602717 A CN A2005100602717A CN 200510060271 A CN200510060271 A CN 200510060271A CN 1907024 A CN1907024 A CN 1907024A
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cooch
methyl acrylate
methyl
methoxy
phenyl
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Inventor
孔小林
胡伟群
郑昀红
张晓铭
朱卫纲
窦花妮
陈定花
邢家华
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ZHEJIANG CHEM-TECH GROUP Co Ltd
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ZHEJIANG CHEM-TECH GROUP Co Ltd
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Abstract

The invention relates to a group of methoxyl methyl acrylate compounds having a formula (I), wherein X=F or H, Q=N or CH; R1, R2, R3, R4=H, NO2, CN, Cl, C1-C9 alkyl or unsaturated hydrocarbons, C1-C6 alkoxy imine methyl, or C1-C6 alkoxy carbonyl. The invention also discloses the process for preparing the compounds and the use of the compounds in making agricultural bactericides.

Description

Methoxyl group displacement methyl acrylate compound bactericidal agent
Technical field
The present invention relates generally to new methoxy-methyl acrylate compounds, the preparation method of this compounds, and this compounds is as the application of disinfectant use in agriculture.
Background technology
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.
At US 4,914, disclose some methoxy-methyl acrylate compounds in No. 128 patent applications, and disclose compound wherein and have bactericidal activity.
Disclosing in the PCT/CN2004/000226 patent application a kind ofly has 2 on side-chain benzene ring, the compound that the 5-dimethyl replaces has bactericidal activity, but do not relate to other 2, the compound that the 5-position replaces.
In the PCT/EP95/03683 patent application, disclose one group of fluorine methoxy-methyl acrylate compound of replacing original methoxyl group with single fluorine methoxyl group and had bactericidal activity, but do not relate to the compound that side chain is a heterocycle, do not relate to the compound that nitro or alkoxy carbonyl group are arranged on the side-chain benzene ring yet.Do not relate to simultaneously yet the substituent compound of alcoxyl formimino group is only arranged on the side-chain benzene ring.
Summary of the invention
One of purpose of the present invention provides a series of new methoxy-methyl acrylate compounds of using as bactericide, comprise that with substituted pyridinyl or band special substituent phenyl be the fluorine methoxy-methyl acrylate compounds of side chain, with with 2, the 5-substituted-phenyl (removes 2, the 5-xylyl is outer) be the methoxy-methyl acrylate compounds of side chain, these compounds are the noval chemical compound that any report is not arranged.Another object of the present invention provides the synthetic method of synthetic these a series of methoxy-methyl acrylates.
The inventor has synthesized the series compound of following general formula by analyzing, studying:
Work as X=F, during Q=N, R 1, R 2, R 3, R 4=H, NO 2, CN, Cl, CH 3COOR 6(R 6For replacing or substituted alkyl not) or CF 3Work as X=F, Q=CH, R 1=NO 2The time, R 2, R 4=H;
Work as X=F, Q=CH, R 1=R 2=R 4=H, R 3=CH=N-OR 5Or COOR 5, R wherein 5=CH 3, C 2H 5, n-C 3H 7, i-C 3H 7, n-C 4H 9, i-C 4H 9, t-C 4H 9
Work as X=H, during Q=CH, R 2, R 3=H; R 1=OMe, CH 3Or N (C 2H 5) 2R 4=CH 3, CN, COOCH 3, COOC 2H 5, COOC 3H 7-n, COOCH (CH 3) 2, COOCH 2CH (CH 3) 2, COOC 4H 9-n, COOCH 2CF 3, COOCH 2CH 2Cl, COOCH 2CH=CH 2COOCH (CH 2Cl) 2, COOCH 2CCH, COOCH (CH 3) CH 2CH 2CH 3, CONHNH 2, COOPh is in above-claimed cpd, and most preferred of the present invention is:
1,3-fluorine methoxyl group-2-[2-(3,5,6-trichloropyridine base-2-oxygen ylmethyl)-phenyl]-methyl acrylate;
2,2-{2-[4-(ethoxy imido grpup methyl)-phenyl oxygen methyl]-phenyl }-3-fluorine methoxy-methyl acrylate;
3,2-[2-(4-chloro-2-nitro-phenoxymethyl)-phenyl]-3-fluorine methoxy-methyl acrylate;
4,2-[2-(5-cyano group-2-methyl-phenyl oxygen methyl)-phenyl]-the 3-methoxy-methyl acrylate;
5,3-[2-(2-methoxyl group-1-methoxycarbonyl-vinyl)-phenyl methoxyl group]-4-methyl-methyl benzoate.
The compounds of this invention is mainly synthetic by the following method:
2-[2-(2 of the present invention, 3,4,5 substituted aryls-2-oxygen ylmethyl)-phenyl]-preparation method of 3-methoxyl group displacement methyl acrylate is 2,3,4,5 substituted aryl phenol and 2-(2-(bromomethyl) phenyl)-3-methoxyl group displacement methyl acrylate adds thermal response with about 1: 1 mol ratio in the presence of acid binding agent and solvent.Reaction temperature and reaction time look raw materials used kind is different with medium and change to some extent, and general reaction temperature is controlled under the solvent refluxing temperature, and the reaction time was at 6-48 hour.Reacting available following reaction equation represents:
The solvent that is suitable in the reaction, can select for use according to different substrates: acetone, oxolane, dimethyl formamide, methyl-sulfoxide, acetonitrile etc., wherein wider with the acetone scope of application.The usage amount of solvent, it is different and different also to look substrate, and the common solvent consumption is controlled at 3-6 times of raw material inventory.
For promoting successful reaction to carry out, need to add acid binding agent in the reaction, to eliminate the HBr that produces in the reaction.The acid binding agent that is suitable for is alkali metal hydroxide, carbonate or acid carbonate, as sodium hydroxide, potassium hydroxide, sodium carbonate, potash or sodium bicarbonate, saleratus etc.The consumption of acid binding agent, for raw material 2-(2-(bromomethyl) phenyl)-3-methoxyl group displacement methyl acrylate feed intake mole 1.5-2.0 doubly.
After reaction finishes, filter, boil off solvent and (wash with water in case of necessity, use ethyl acetate extraction again, drying, precipitation), obtain the solids crude product, use ethyl alcohol recrystallization again, or add the mixed liquid of ethyl acetate with benzinum and make solvent, carry out column chromatography, promptly get highly finished product of the present invention.
The inventor find this compounds can with the use that is mixed of conventional sterilization agent, nematocide, plant growth regulator, fertilizer or other agricultural chemicals of insecticide, different mechanism of action.
Compound of the present invention and preparation thereof have following characteristics and advantage:
1, has bactericidal activity efficiently, than preventing and treating well under the low dosage, good preventive effect is all arranged as the powdery mildew of each plant species, rust, downy mildew, anthracnose etc. by fungus-caused disease.
2, to various melon safety such as trial crops such as wheat, strawberry, cucumber, pumpkins, plant growth is had no adverse effects.
3, have rational toxicity, eco-toxicity and Environmental compatibility, belong to the environmentally friendly agricultural chemicals of low toxicity.
Structural formula provided by the present invention is simple synthetic method not only, and has higher bactericidal activity, possesses the potentiality that are developed to the commercialization bactericide.Its preparation is than preventing and treating plurality of plant diseases effectively under the low dosage.As wheat powdery mildew (Erysiphe graminis), powdery mildew of cucumber (Sphaerotheca fuligenea), cucumber downy mildew (Pseudoperonospora cubensis), cucumber anthracnose (Colletotrichum lagenarium) etc.
Embodiment:
The following examples can make those skilled in the art comprehensively understand the present invention, but do not limit the present invention in any way.
Embodiment 1 compound 1
2-[2-(5-cyano group-2-methyl-phenyl oxygen methyl)-phenyl]-3-methoxy-methyl acrylate synthetic
At room temperature 1.33g (0.01 mole) 2-methyl-5-cyanophenol is added to 150ml and fills in the there-necked flask of 60ml dry acetone, add 2.76g (0.02 mole) potash then, stirring at room 30 minutes slowly adds 2.85g (0.01 mole) 2-(2-(bromomethyl) phenyl)-3-methoxy-methyl acrylate then.Back flow reaction finished in 4 hours then, filtered, and concentrated, and got crude product.Mixed liquor (1: 4) with ethyl acetate and benzinum obtains Compound I 3.13g for eluent carries out column chromatography, is white solid, and yield is 93%.Product is also analyzed with conclusive evidence through nuclear magnetic resonnance (1HNMR) and mass spectrum (MS).Analysis result is as follows:
1HNMR：2.324(3H，s)，3.732(3H，s)，3.885(3H，s)，5.012(2H，s)，6.917-6.920(1H，s)，7.126-7.260(3H，m)，7.313-7.361(2H，m)，7.481-7.503(1H，m)，7.640(1H，s)，MS 337
Annotate: 1The HNMR spectrum is to use CDCl 3The solvent record.Abbreviation used in experiment is as follows:
The unimodal d=doublet of NMR=nuclear magnetic resonnance s=t=triplet q=quartet m=multiplet
Embodiment 2 compounds 4
3-[2-(2-methoxyl group-1-methoxycarbonyl-vinyl)-phenyl methoxyl group]-4-methyl-methyl benzoate synthetic
At room temperature 3.32g (0.02 mole) 3-hydroxy-4-methyl methyl benzoate being added to 250ml fills in the there-necked flask of 100ml dry acetone, add 5.52g (0.04 mole) potash then, stirring at room 30 minutes slowly adds 5.7g (0.02 mole) 2-(2-(bromomethyl) phenyl)-3-methoxy-methyl acrylate then.Back flow reaction finished in 4 hours then, filtered, and concentrated, and got crude product.Mixed liquor (1: 4) with ethyl acetate and benzinum obtains Compound I 6.22g for eluent carries out column chromatography, is faint yellow solid, and yield is 84%.Fusing point: 97.2～101.6 ℃.Product is also analyzed with conclusive evidence through nuclear magnetic resonnance (1HNMR) and mass spectrum (MS).Analysis result is as follows:
1HNMR：2.316(3H，m)，3.713(3H，s)，3.849(3H，s)，3.902(3H，s)，5.019(2H，s)，7.198-7.216(2H，m)，7.271-7.483(2H，m)，7.552-7.613(1H，m)，7.687(3H，m)，MS：370
Embodiment 3 compounds 5
2-{2-[4-(ethoxy imido grpup methyl)-phenyl oxygen methyl]-phenyl }-3-fluorine methoxy-methyl acrylate synthetic
At room temperature 4.95g (0.03 mole) 4-(ethoxy imines-methyl)-phenol is added to 250ml and fills in the there-necked flask of 100ml dry acetone, add 8.28g (0.06 mole) potash then, stirring at room 30 minutes slowly adds 9.09g (0.03 mole) 2-(2-(bromomethyl) phenyl)-3-fluorine methoxy-methyl acrylate then.Back flow reaction finished in 4 hours then, filtered, and concentrated, and got crude product.Mixed liquor (1: 4) with ethyl acetate and benzinum obtains Compound I 8.94g for eluent carries out column chromatography, is white solid, and yield is 77%.Fusing point: 74.1-76.1 ℃.Product is also analyzed with conclusive evidence through nuclear magnetic resonnance (1HNMR) and mass spectrum (MS).Analysis result is as follows:
1HNMR：1.307(3H，t)，3.823(3H，s)，4.197(2H，q)，4.988(2H，s)，5.403-5.536(2H，d)，6.869-6.886(2H，d)，7.206-7.263(2H，m)，7.369-7.535(4H，m)，7.712(1H，s)，8.006(1H，s)
MS 387.1
Embodiment 4 compounds 6
2-[2-(4-chloro-2-nitro-phenoxymethyl)-phenyl]-3-fluorine methoxy-methyl acrylate synthetic
At room temperature 3.47g (0.02 mole) 2-nitro-4-chlorophenol is added to 250ml and fills in the there-necked flask of 100ml dry acetone, add 5.52g (0.04 mole) potash then, stirring at room 30 minutes slowly adds 6.06g (0.02 mole) 2-(2-(bromomethyl) phenyl)-3-fluorine methoxy-methyl acrylate then.Back flow reaction finished in 4 hours then, filtered, and concentrated, and got crude product.Mixed liquor (1: 4) with ethyl acetate and benzinum obtains Compound I 7.00g for eluent carries out column chromatography, is white solid, and yield is 89%.Fusing point: 117.8～118 ℃.Product is also analyzed with conclusive evidence through nuclear magnetic resonnance (1HNMR) and mass spectrum (MS).Analysis result is as follows:
1HNMR：3.753(3H，s)，5.139(2H，s)，5.433-5.565(2H，d)，6.943-6.965(1H，d)，7.188-7.209(1H，d)，7.265-7.422(3H，m)，7.573-7.591(1H，d)，7.739(1H，s)，7.824(1H，s)MS 395.5
Embodiment 5 compounds 7
3-fluorine methoxyl group-2-[2-(3,5,6-trichloropyridine base-2-oxygen ylmethyl)-phenyl]-methyl acrylate synthetic
At room temperature with 4g (0.02 mole) 2-hydroxyl-3,5, the 6-trichloropyridine is added to 250ml and fills in the there-necked flask of 100ml dry acetone, add 5.52g (0.04 mole) potash then, stirring at room 30 minutes slowly adds 6.1g (0.02 mole) 2-(2-(bromomethyl) phenyl)-3-fluorine methoxy-methyl acrylate then.Back flow reaction finished in 4 hours then, filtered, and concentrated, and got crude product.Mixed liquor (1: 4) with ethyl acetate and benzinum obtains Compound I 6.78g for eluent carries out column chromatography, is white solid, and yield is 80%.Fusing point: 108.3～108.8 ℃.Product is also analyzed with conclusive evidence through nuclear magnetic resonnance (1HNMR) and mass spectrum (MS).Analysis result is as follows:
1HNMR：3.729(3H，s)，5.332(2H，s)，5.413-5.545(2H，d)7.198-7.264(1H，m)，7.378-7.416(2H，m)，7.592-7.608(1H，d)，7.698-7.729(2H，d)
MS 420
The equal embodiment 1 of the preparation method of other compound carries out in the table 1, and its result is as shown in table 1 below:
Table 1
Figure A20051006027100081
Figure A20051006027100091
Figure A20051006027100101
Embodiment 6 biological activity determinations:
Provide below and use compound of the present invention to carry out the example of biological activity determination, it is to be noted that the present invention not merely is confined in the scope of following example.
The bactericidal activity evaluation test is carried out according to following method:
The compound treatment concentration of determination of activity for the first time (general sieve) test is 200mg/L, and the compound treatment concentration of determination of activity once more (primary dcreening operation or multiple sieve) test is determined drug concentration according to compound biologically active situation, and method of testing all adopts live body potted plant.
1. bacterium of downy mildew of cucumber (Pseudoperonospora cubensis)
Select the potted plant cucumber seedling of two leaf periods (plucking growing point) growing way unanimity, spraying is handled the back and is dried naturally, handles about the 24h of back and inoculates, and gets the sick leaf of fresh cucumber downy mildew, dip in writing brush and to get 10 ℃ of left and right sides distilled water and wash disease leaf back sporangium, be made into sporangia suspension (2-3 * 10 5Individual/ml), and the laboratory preparation of adding＜0.1% Tween-80.With inoculation sprayer (pressure 0.1MPa) even spraying inoculation on cucumber seedling, postvaccinal examination material moves to phytotron, keep relative moisture 100%, temperature is 15-20 ℃, keep 15-24 ℃ of temperature behind the 24h, relative moisture about 90% is preserved moisture and is brought out, and 5d backsight blank incidence carries out the classification investigation, refers to calculate preventive effect by disease.
2. gray mold (Botrytis cinerea)
Adopt the blade bacterination process.Select the consistent potted plant cucumber seedlings of two leaf period growing ways, treat that reagent spray dries after, connect the bacterium cake on blade.22-26 ℃ of half-light preserved moisture behind the 24h, recovers natural lighting and cultivates about 4d.Wait to contrast abundant morbidity back and measure each inoculation point scab diameter, calculate preventive effect with slide calliper rule.
3. rice sheath blight disease (Rhizoctonia solani)
Select the consistent potted plant cucumber seedlings of two leaf period growing ways, treat that reagent spray dries after, have the one side of mycelia to connect the bacterium cake and be affixed on the blade.22-26 ℃ of half-light preserved moisture behind the 24h, recovers natural lighting and cultivates about 4d.Wait to contrast abundant morbidity back and measure each inoculation point scab diameter, calculate preventive effect with slide calliper rule.
4. powdery mildew of cucumber bacterium (Sphaerotheca uliginea)
Select a slice leaf period, the consistent cucumber seedling of growing way, 24h dries in the shade after spraying is handled.Wash and get the fresh spore that covers with on the powdery mildew cucumber leaves, filter, make spore concentration and be the suspension about 100,000/ml, and the laboratory preparation that adds＜0.1% Tween-80 carries out spray inoculation with double gauze.Postvaccinal examination material natural air drying moves under the thermostatic chamber light in (21-23 ℃) then, and 7-8d backsight blank incidence carries out the classification investigation, refers to calculate preventive effect by disease.
5. sclerotinia rot of colza (Sclerotinia sclerotiorum)
Adopt the excised leaf bacterination process.After treating that reagent spray dries, connect bacterium cake (diameter 5mm) on blade.25 ℃ of half-lights are preserved moisture behind the 24h, recover natural lighting and cultivate about 4-5d.Wait to contrast abundant morbidity " Invest, Then Investigate " experimental result, calculate preventive effect.
The selection result sees each table for details, and living test is tested the result and shown: The compounds of this invention has good bactericidal activity, and fungicidal spectrum is wider, to trial crops safety.
Subordinate list 1: compound is to the general sieve result of each target
Numbering Concentration mg/L Downy mildew % Gray mold % Banded sclerotial blight % Powdery mildew %
1 200 94.5 41.70 49.08 100
2 200 83.24 50.0 49.39 94.17
3 200 81.23 40.0 0 99.21
4 200 98.14 49.68 59.01 92.18
5 200 99.87 32.90 54.93 100
6 200 97.22 16.56 9.63 98.41
7 200 100 2.3 0 100
8 200 100 33.33 0 100
9 200 12.76 14.29 0 0
10 200 34.89 2.27 39.62 33.21
11 200 88.89 26.73 25.54 100
12 200 97.22 56.74 47.88 100
13 200 94.44 54.67 52.45 98.15
14 200 83.26 22.11 5.60 90.12
15 200 85.24 28.08 0 100
16 200 89.54 37.67 0 100
17 200 94.89 0 0 49.38
18 200 10.23 0 0 19.88
Subordinate list 2: compound is to the multiple sieve result of cucumber downy mildew
The compound code name Concentration mg/L Preventive effect %
12 200 98.30
100 86.10
50 71.25
25 47.40
12.5 26.93
5 200 100
100 97.78
50 81.11
25 60.54
12.5 53.24
6 200 98.15
100 93.21
50 84.66
25 47.40
12.5 25.00
7 200 100
100 99.31
50 95.14
25 95.83
12.5 87.50
1 200 94.44
100 83.33
50 75.56
25 59.63
12.5 50.71
8 200 99.87
100 97.62
50 92.36
25 85.71
12.5 65.93
Subordinate list 3: compound is to the multiple sieve result of powdery mildew of cucumber
The compound code name Concentration mg/L Preventive effect %
12 200 100
100 98.15
50 77.78
25 66.67
12.5 43.59
5 200 100
100 100
50 95.24
25 78.69
12.5 68.97
6 200 62.96
100 51.85
50 48.89
25 29.06
12.5 11.11
7 200 100
100 99.07
50 98.89
25 93.33
12.5 88.89
1 200 100
100 94.4
50 85.3
25 72.6
12.5 63.2
8 200 98.23
100 94.44
50 93.83
25 89.81
12.5 53.54
Subordinate list 4 cucumber downy mildew field test results
Test is handled Valid density (a.i.) mg/L Control efficiency (%)
The Shanghai farming academy of sciences (behind three medicines 10 days) Maanshan City's plant test station for plant protection (behind the secondary medicine 7 days)
5% compound 7EC 200 91.15 88.55
100 85.35 88.60
50 69.45 83.93
25 60.25 76.09
72% gram reveals WP 1152 78.73 /
957.6 / 90.95
5% compound 1EC 200 89.02 92.51
100 83.43 87.75
50 75.87 86.31
25 62.26 80.56
72% gram reveals WP 1152 87.38 /
957.6 / 94.01
Field test results shows, under 50-100mg/L concentration, the compound 1 and the 7 pairs of cucumber downy mildews and powdery mildew of cucumber all show good preventive effect, and the lasting period is long, to crop safety, has better market application.Recommended dose is 50-100mg/L, and spraying time is cucumber downy mildew premorbid or their early stage first, and a situation arises or weather condition is sprayed medicine once week about to look disease.
Need be at other carry out field trial on the melon or fruit tree, flowers and other crops, for further exploitation provides scientific basis.

Claims (11)

1, one group of methoxy-methyl acrylate compounds bactericide, feature are shown in structural formula (I) and isomer:
Figure A2005100602710002C1
Wherein work as X=F, during Q=N, R 1, R 2, R 3, R 4=H, NO 2, CN, Cl, CH 3COOR 6(R 6For replacing or substituted alkyl not) or CF 3
Work as X=F, Q=CH, R 1=NO 2The time, R 2, R 4=H;
Work as X=F, Q=CH, R 1=R 2=R 4=H, R 3=CH=N-OR 5Or COOR 5, R wherein 5=CH 3, C 2H 5, n-C 3H 7, i-C 3H 7, n-C 4H 9, i-C 4H 9, t-C 4H 9
Work as X=H, during Q=CH, R 2, R 3=H; R 1=OMe, CH 3Or N (C 2H 5) 2R 4=CH 3, CN, COOCH 3, COOC 2H 5, COOC 3H 7-n, COOCH (CH 3) 2, COOCH 2CH (CH 3) 2, COOC 4H 9-n, COOCH 2CF 3, COOCH 2CH 2Cl, COOCH 2CH=CH 2, COOCH (CH 2Cl) 2COOCH 2CCH, COOCH (CH 3) CH 2CH 2CH 3, CONHNH 2, COOPh.
2, according to one group of compound of claim 1, feature is shown in structural formula (II) and isomer:
Figure A2005100602710002C2
R wherein 1, R 2, R 3, R 4=H, NO 2, CN, Cl, CH 3, COOR 6(R 6For replacing or substituted alkyl not) or CF 3
3, according to one group of compound of claim 1, feature is shown in structural formula (III) and isomer:
Figure A2005100602710002C3
R=CH=N-OR in the formula 5Or COOR 5
R wherein 5=CH 3, C 2H 5, n-C 3H 7, i-C 3H 7, n-C 4H 9, i-C 4H 9, t-C 4H 9
4, according to one group of compound of claim 1, feature is shown in structural formula (IV) and isomer:
Figure A2005100602710003C1
R=Cl, CH in the formula 3, COOC 2H 5
5, according to one group of compound of claim 1, feature is shown in structural formula (V) and isomer:
Figure A2005100602710003C2
R in the formula 1=OMe, CH 3Or N (C 2H 5) 2R 4=CH 3, CN, COOCH 3, COOC 2H 5, COOC 3H 7-n, COOCH (CH 3) 2, COOCH 2CH (CH 3) 2, COOC 4H 9-n, COOCH 2CF 3, COOCH 2CH 2Cl, COOCH 2CH=CH 2, COOCH (CH 2Cl) 2, COOCH 2CCH, COOCH (CH 3) CH 2CH 2CH 3, CONHNH 2, COOPh.
6, a kind of fluorine-containing methoxy-methyl acrylate compounds as claimed in claim 2 is characterized in that referring to: 3-fluorine methoxyl group-2-[2-(3,5,6-trichloropyridine base-2-oxygen ylmethyl)-phenyl]-methyl acrylate.
7, a kind of fluorine-containing methoxy-methyl acrylate compounds as claimed in claim 3 is characterized in that referring to: 2-{2-[4-(ethoxy imido grpup methyl)-phenyl oxygen methyl]-phenyl }-3-fluorine methoxy-methyl acrylate.
8, a kind of fluorine-containing methoxy-methyl acrylate compounds as claimed in claim 4 is characterized in that referring to: 2-[2-(4-chloro-2-nitro-phenoxymethyl)-phenyl]-3-fluorine methoxy-methyl acrylate.
9, a kind of fluorine-containing methoxy-methyl acrylate compounds as claimed in claim 5 is characterized in that referring to: 2-[2-(5-cyano group-2-methyl-phenyl oxygen methyl)-phenyl]-the 3-methoxy-methyl acrylate.
10, a kind of fluorine-containing methoxy-methyl acrylate compounds as claimed in claim 5 is characterized in that referring to: 3-[2-(2-methoxyl group-1-methoxycarbonyl-vinyl)-phenyl methoxyl group]-4-methyl-methyl benzoate.
11, one groups of purposes as claim 1,2,3,4,5 described methoxy-methyl acrylate compounds is characterized in that being used for the agrochemicals bactericide.
CNA2005100602717A 2005-08-03 2005-08-03 Methoxyl group displacement methyl acrylate compound bactericidal agent Pending CN1907024A (en)

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