CN1918985A - Application of 2-cyano-3-amino-3-ethyl phenylacrylate for preventing agronomic crop disease - Google Patents

Application of 2-cyano-3-amino-3-ethyl phenylacrylate for preventing agronomic crop disease Download PDF

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Publication number
CN1918985A
CN1918985A CN 200610125921 CN200610125921A CN1918985A CN 1918985 A CN1918985 A CN 1918985A CN 200610125921 CN200610125921 CN 200610125921 CN 200610125921 A CN200610125921 A CN 200610125921A CN 1918985 A CN1918985 A CN 1918985A
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amino
cyano group
ethyl phenylacrylate
disease
ethyl
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CN100435635C (en
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王凤云
徐尚成
倪珏萍
刁亚梅
刘丽
沈晓霞
胡恩宇
李长乐
郭丽琴
马海军
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Jiangsu Pesticide Research Institute Co., Ltd.
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JIANGSU PESTICIDE INST CO Ltd
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Abstract

The invention discloses a building pesticide composition, which contains 2-cyano-3-amino-3-phenyl ethyl acrylate to prevent pest due to multiple fungus.

Description

The application of 2-cyano group-3-amino-3-ethyl phenylacrylate for preventing agronomic crop disease
Technical field
The present invention relates to compound 2-cyano group-3-amino-3-ethyl phenylacrylate and prevent and treat the application of the disease that causes by multiple disease funguses such as sickle-like bacteria, rest fungus, botrytis cinereas on the various crop.
Background technology
Aspect agriculture plant protection, be principle with the disease pest and weed comprehensive regulation, to adopt agricultural chemicals to reduce the harm of disease pest and weed inevitably, improve crop yield and quality.Agricultural chemicals is as the important agricultural material product of a class, in China's research and development of existing decades, the history of production application.At first, diversity of organism makes the pest population in damage to crops and gardens constantly change, and is more and more higher for the requirement of control medicament; Secondly, the chronic administration of agricultural chemicals makes pest develop immunity to drugs, and this just needs, and the pesticide research developer develops efficiently, safety, and eco-friendly pharmaceutical preparations, to satisfy the needs of plant protection.The research and development of China's novel pesticide and novel formulation have possessed certain basis, have developed serial new varieties, satisfy the needs of agricultural production.
Compound 2-cyano group in the prior art-3-amino-3-ethyl phenylacrylate has only as the weed killer herbicide use, does not see the report that other purposes is arranged so far.
Summary of the invention
The purpose of this invention is to provide following formula: compound 2-cyano group-3-amino-3-ethyl phenylacrylate and prevent and treat the application of disease on the multiple kinds of crops.The pathogen of described disease can be for example sickle-like bacteria, rest fungus, botrytis cinerea etc.
Figure A20061012592100031
The present invention also provides a kind of composition pesticide, it contains compound 2-cyano group-3-amino-3-ethyl phenylacrylate as active component, form with acceptable carrier on the agricultural chemicals, wherein the acceptable carrier weight ratio is 1: 99 on 2-cyano group-3-amino-3-ethyl phenylacrylate and the agricultural chemicals.
The compound 2-cyano group that adopts among the present invention-3-amino-3-ethyl phenylacrylate is effective bactericide, and is all effective to tools such as various crop disease such as wheat scab, cotton wilt, Phytophthora capsici disease, bakanae disease of rice, melon gray mold, wheat sharp eyespot, rice blast, wheat rusts.As new sterilizing use,, will provide efficient, safe bactericide for agricultural production preventing and treating aspect the crop pest.Especially when to the control efficiency of gibberella zeaze petch of wheat and barley when outstanding, more confident it is developed as disinfectant use in agriculture.
In the present invention, compound 2-cyano group-3-amino-3-ethyl phenylacrylate can also use simultaneously with the agricultural chemicals of other type, reach the purpose of the comprehensive regulation to prevent and treat homochronous disease pest and weed, with it can compatibility or the medicament used with bactericide and insecticide are arranged is diversified.Bactericide can be: methoxy acrylic bactericide, triazole bactericidal agent, acid amide fungicides, other heterocyclic nitrogen-group fungicide etc.; Insecticide can be nicotinic insecticide, pyrethroid insecticides etc.When disease and insect pest same period taking place or needing medication simultaneously, can mix and use, also can make composite preparation and use.
1, compound 2-cyano group of the present invention-3-amino-3-ethyl phenylacrylate is effective fungicide, can be used as disinfectant use in agriculture and prevents and treats crop pests such as agricultural and gardening.Especially wheat scab, cotton wilt, Phytophthora capsici disease, bakanae disease of rice, melon gray mold, wheat sharp eyespot, rice blast, wheat rust etc.
2, compound 2-cyano group of the present invention-3-amino-3-ethyl phenylacrylate is effective fungicide, can mix with other insecticide, bactericide etc. to use or form composition and prevent and treat multiple damage by disease and insect, when especially multiple damage by disease and insect takes place simultaneously.The bactericide of compatibility can be with it: methoxy acrylic bactericide, triazole bactericidal agent, acid amide fungicides, other heterocyclic nitrogen-group fungicide etc., be used to prevent and treat rice blast, banded sclerotial blight, bakanae disease etc., gibberella zeaze petch of wheat and barley, banded sclerotial blight, powdery mildew, rust etc., cotton wilt, anthracnose etc., vegetables powdery mildew, rot, downy mildew, gray mold, eqpidemic disease etc., fruit tree apple scab, spot defoliation etc.The insecticide of compatibility can be nicotinic insecticide, pyrethroid insecticides etc. with it, prevent and treat water rice hopper, leafhopper, cecidomyiia, Lissorhoptrus oryzophilus Kuschel etc., control wheat class aphid, mythimna separata etc., control vegetable aphid, aleyrodid, cabbage caterpillar etc., control fruit aphid etc.
3, the present invention also provides and has contained the compound 2-cyano group-3-amino-bactericidal composition of 3-ethyl phenylacrylate and preparation method of synergetic pesticide composition.
According to composition of the present invention, preferred content is from the active component of 1-99% weight.Carrier of the present invention is the material that satisfies following condition: being convenient to be applied to the site that has processing after it and active component dispose, for example can be plant, seed or soil; Or help storing, transport or operation.Carrier can be solid or liquid, comprises being generally gas but being compressed into the material of liquid and can having used any usually used carrier when the preparation bactericidal composition.
Suitable solid carrier comprises natural and synthetic clay and silicate for example diatomite, talcum, Attagel, alumina silicate (kaolin), montmorillonite and mica; Calcium carbonate; Calcium sulphate; Ammonium sulfate; Synthetic silica and synthetic calcium silicates or alumina silicate; Element such as carbon and sulphur; Natural synthetic resin such as cumarone resin, polyvinyl chloride and styrene polymer and copolymer; Solid polystream phenol; Pitch; Wax such as beeswax, paraffin.
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 cyclohexyl ketone; 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, these mixtures of liquids also are suitable for usually.
Composition pesticide is processed into the form of concentrate usually and is used for transportation with this, by the user it is diluted before using.A spot of supporting surfactant has and helps dilution.Like this, in composition of the present invention, at least a carrier is surfactant preferably, and for example composition can contain at least two kinds of carriers, and wherein at least a is surfactant.
Surfactant can be emulsifier, dispersant or wetting agent; It can be surfactant nonionic or ion.The example of suitable surfactant comprises polyacrylic acid and lignin sulfonic acid sodium salt and calcium salt; Contain the fatty acid of at least 12 carbon atoms or the condensation compound of fatty amine or acid amides and oxirane and/or expoxy propane in the molecule; Glycol, sorbierite, the mixture of sucrose and pentaerythritol fatty ester and fatty amine or acid amides and oxirane and/or expoxy propane; Fatty alcohol or alkylphenol such as paraoctyl phenol or to the condensation compound of octyl group cresols and oxirane and/or expoxy propane; The sulphate of these condensation products or sulfonate; The alkali metal or the alkaline earth metal that in molecule, contain at least 10 carbon atom sulfuric acid or 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 the present composition is wetting powder, pulvis, granule and solution, emulsible concentrating agents, emulsion, suspension concentrating agents, aerosol and aerosol.Wetting powder contains 25,50 or 75% weight active component usually, and usually except that inert carrier, also contains 3-10% weight fraction powder, and if need to 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 composition similar to wetting powder but do not have dispersant usually, further with the solid carrier dilution, is contained 0.5-10% weight composition of active components usually down on the farm.Granula is prepared into usually has 10-100 order (1.676-0.152mm) size, available agglomerating or injection technique preparation.Usually, granula contains the active component of 0.5-75% weight and 0-10% weight additive such as stabilizing agent, surfactant, slowly-releasing modifying agent.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, the 1-50%W/V active component, other additive of 2-20%W/V emulsifier and 0-20%W/V such as stabilizing agent, bleeding agent and corrosion inhibitor, suspension concentrating agents contain the active component of 10-75% 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 usually.Water dispersant and emulsion, 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.
Embodiment
Formulation Example 1:10% missible oil
10 parts in 2-cyano group-3-amino-3-ethyl phenylacrylate
12 parts of Tween 80s
N, 3 parts of dinethylformamides
Dimethylbenzene is supplied 100 parts
Formulation Example 2:90% soluble liquid
90 parts in 2-cyano group-3-amino-3-ethyl phenylacrylate
10 parts of N-Methyl pyrrolidone
Formulation Example 3:70% soluble liquid
70 parts in 2-cyano group-3-amino-3-ethyl phenylacrylate
30 parts of methyl ethyl ketones
Formulation Example 4:15% suspending agent
15 parts in 2-cyano group-3-amino-3-ethyl phenylacrylate
10 parts of ethylene glycol
5 parts of neopelexes
0.5 part of xanthans
4.5 parts of stabilizing agents
65 parts in water
Formulation Example 5:25% wetting powder
25 parts in 2-cyano group-3-amino-3-ethyl phenylacrylate
3 parts of stabilizing agents
12 parts of sldium lauryl sulfates
10 parts of Lignosites
50 parts of kaolin
Application Example 1:
2-cyano group-3-amino-3-ethyl phenylacrylate has wider fungicidal spectrum test
Method: contain toxic medium method.
Measuring 2-cyano group-3-amino-3-ethyl phenylacrylate suppresses multiple germ mycelial growth.It is 20,2,0.2 μ g/ml series concentration that medicament 2-cyano group to be measured-3-amino-3-ethyl phenylacrylate is prepared into concentration, make the pastille medium, move into the fresh mycelia piece of wheat scab, cotton wilt, Phytophthora capsici disease, bakanae disease of rice, gray mold of cucumber, wheat sharp eyespot germ after 8 hours respectively, repeat 6, putting into 25 ℃ of incubators cultivated 4 days, measure the colony growth diameter, calculate mycelial growth inhibition rate.
Table 1 exsomatizes and suppresses the determination of activity of multiple germ mycelial growth
Pathogen Mycelial growth inhibition rate (%)
20ug/ml 2ug/ml 0.2ug/ml
Gibberella saubinetii (Gibberella zeae) 100 98 57
Cotton wither (Fusarium oxysporum) 88 28 24
Phytophthora capsici (Phytophthora capsici) 94 85 59
Rice bakanae disease (Gibberella fujikuroi) 92 70 64
Cucumber grey mold (Botrytis cinerea) 62
Wheat line withered (Rhizoctonia solani) 77
2-cyano group-3-amino-3-ethyl phenylacrylate with concentration 20,2,0.2ug/ml to 6 kinds of pathogen isolated measurings, carrying out the fungicidal spectrum result of the test shows: drug concentration is that 20ug/ml is to wheat scab, cotton wilt, Phytophthora capsici disease, bakanae disease of rice, gray mold of cucumber, the certain activity of wheat sharp eyespot pathogen performance, mycelial growth inhibition rate is greater than 50%, and is relatively poor to all the other pathogen activity.Drug concentration is that 0.2ug/ml is respectively 57%, 59%, 64% to the inhibiting rate that wheat scab, Phytophthora capsici disease, bakanae disease of rice mycelia grow, the performance greater activity.
Application Example 2:
2-cyano group-3-amino-3-ethyl phenylacrylate is to the bactericidal activity test of common bacterial strain of wheat scab and resistant strain
Measure medicament to the growth inhibiting EC of wheat scab mycelia 50And virulence equation.Medicament 2-cyano group to be measured-3-amino-3-ethyl phenylacrylate, carbendazim are prepared into the high concentration mother liquor respectively, add mother liquor in the 50-60 ℃ of PSA medium and make it even dispersion, be prepared into the pastille medium of series concentration.Move into gibberella saubinetii G after 8 hours respectively 2(resistant strain), G 4(common bacterial strain) fresh mycelia piece repeats 6, puts into 25 ℃ of incubators and cultivates 3 days, measures the colony growth diameter, calculates EC 50And virulence equation.It during test is the contrast medicament with the carbendazim.Concrete outcome is as shown in table 2.The result shows that 2-cyano group-3-amino-3-ethyl phenylacrylate is better than carbendazim to the common bacterial strain of carbendazim.2-cyano group-3-amino-3-ethyl phenylacrylate is close with common bacterial strain activity to the carbendazim resistance bacterial strain, tentatively shows with the medicament carbendazim not have cross resistance.
Table 2 2-cyano group-3-amino-3-ethyl phenylacrylate, carbendazim are to the isolated measuring result of wheat scab
Bacterial strain Medicament Virulence regression equation EC 50 (ug/ml) Relative virus force index
G2 (resistant strain) Carbendazim Y=1.9666+3.0436X 9.9231 5.65
2-cyano group-3-amino-3-ethyl phenylacrylate Y=6.5342+2.1241X 0.1895 295.83
G4 (common bacterial strain) Carbendazim Y=5.9099+3.6195X 0.5606 100
2-cyano group-3-amino-3-ethyl phenylacrylate Y=6.1185+1.7274X 0.2252 248.93
Relative virus force index=100 * with reference to medicament EC 50The EC of/medicament 50
The result shows that to the activity of common bacterial strain, 2-cyano group-3-amino-3-ethyl phenylacrylate is 2.5 times of carbendazim; The antagonism bacterial strain, 2-cyano group-3-amino-3-ethyl phenylacrylate is 52 times of carbendazim.Concerning carbendazim, be 100 with the EC50 of common bacterial strain, the relative virus force index of resistant strain is 5.65; Concerning 2-cyano group-3-amino-3-ethyl phenylacrylate, active close to common bacterial strain and resistant strain.Show that tentatively compound 2-cyano group of the present invention-3-amino-3-ethyl phenylacrylate is different with the mechanism of action of carbendazim, may not have cross resistance.
Application Example 3:
2-cyano group-3-amino-3-ethyl phenylacrylate suppresses the test of spore sprout active
Adopt culture dish rudiment method.
Measure the inhibitory action of 2-cyano group-3-amino-3-ethyl phenylacrylate to the rudiment of wheat scab conidium.Preparation spore suspension (every visual field 40-60 spore under the low power lens) with medicament suspension mixed in equal amounts, is mixed with the suspension that drug concentration is 320,160,80,40,20,10 μ g/ml.After fully mixing, draw 0.45ml suspension respectively, be applied in the culture dish on the PSA flat board, put into 25 ℃ of incubators and cultivate after 6 hours, inverted microscope is checked spore germination rate (200 spores of every ware casual inspection surpass minor axis as rudiment with germ tube length).Calculation correction rudiment inhibiting rate is asked EC 50And virulence equation.
Table 3 2-cyano group-3-amino-3-ethyl phenylacrylate suppresses wheat scab conidium rudiment result of the test
Medicament Virulence regression equation EC 50(ug/ml) Relative virus force index
Copper sulphate Y=12.937-3.6449x 150.50 100
2-cyano group-3-amino-3-ethyl phenylacrylate Y=0.9276+2.6210x 35.79 420.51
The result shows that 2-cyano group-3-amino-3-ethyl phenylacrylate has certain inhibitory action to the rudiment of wheat scab conidium, and it is good that preventive effect contrasts medicament copper sulphate.And carbendazim does not have inhibitory action to the rudiment of wheat scab conidium.
Application Example 4:
2-cyano group during greenhouse pot culture-3-amino-3-ethyl phenylacrylate is prevented and treated the wheat scab test
Method 1: protective effect is measured
Adopt stab inoculation.Earlier 2-cyano group-3-amino-3-ethyl phenylacrylate, carbendazim series concentration sample are sprayed on the wheat (two leaf stage) uniformly, handle after one day, first blade middle and lower part with major part acupuncture wheat, two holes on every blade are got fresh mycelia piece (diameter 5mm) again and are bonded at porose place on the blade, and every sample is done 8 repetitions, cover is preserved moisture with preserving moisture, ordinary ray, 26 ℃ of temperature, humidity is more than 95%.Checkout facility result after four days measures scab length, calculates inhibiting rate.2-cyano group-3-amino-3-ethyl phenylacrylate adopts stab inoculation to do the protection effect to the wheat scab germ and measures, the results are shown in Table 4.
Table 4 2-cyano group-3-amino-3-ethyl phenylacrylate, carbendazim are to wheat scab live body protection effect (%)
Medicament Bacterial strain Drug concentration (ug/ml)
800 400 200 100 50
Carbendazim G2 71.6 50.1 46.1 5.8 0
G4 97.8 88.0 76.0 64.4 59.6
2-cyano group-3-amino-3-ethyl phenylacrylate G2 98.3 98.1 81.8 75.7 61.2
G4 98.1 96.7 87.1 76.2 69.0
G2 is a resistant strain, and G4 is common bacterial strain
The result shows: no matter common bacterial strain or resistant strain, the protective effect of 2-cyano group-3-amino-3-ethyl phenylacrylate is close, and is quite active; And the activity of carbendazim antagonism bacterial strain is starkly lower than common bacterial strain.For common bacterial strain, two medicament activity are close; And for resistant strain, the activity of 2-cyano group-3-amino-3-ethyl phenylacrylate significantly is better than carbendazim.
Method 2: therapeutic action is measured
Adopt stab inoculation.With first blade middle and lower part of major part acupuncture wheat (two leaf stage), two holes on every blade are got fresh mycelia piece (diameter 5mm) again and are bonded at porose place on the blade earlier, every sample is done 8 repetitions, and cover is preserved moisture ordinary ray with preserving moisture, 26 ℃ of temperature, humidity is more than 95%.Handle after one day, 2-cyano group-3-amino-3-ethyl phenylacrylate, carbendazim series concentration sample are sprayed on the wheat uniformly, checkout facility result after three days measures scab length, calculates inhibiting rate.2-cyano group-3-amino-3-ethyl phenylacrylate adopts stab inoculation to make the mensuration of therapeutic action to wheat scab, the results are shown in Table 5.
Table 5 2-cyano group-3-amino-3-ethyl phenylacrylate, carbendazim are to wheat scab live body result of treatment (%)
Medicament Bacterial strain Drug concentration (ug/ml)
800 400 200 100
Carbendazim G2 8.6 0 0 0
G4 54.1 50.6 32.1 27.2
2-cyano group-3-amino-3-ethyl phenylacrylate G2 78.4 75.0 66.2 56.4
G4 81.2 71.9 63.4 54.0
G2 is a resistant strain, and G4 is common bacterial strain
The result shows: no matter common bacterial strain or resistant strain, the therapeutic action of 2-cyano group-3-amino-3-ethyl phenylacrylate is close, and is quite active; And the activity of carbendazim antagonism bacterial strain is starkly lower than common bacterial strain; 2-cyano group-3-amino-3-ethyl phenylacrylate is better than carbendazim.
Application Example 5:
2-cyano group-3-amino-3-ethyl phenylacrylate is prevented and treated the wheat scab field plot trial
Establish the processing such as blank of 2-cyano group-3-amino-3-ethyl phenylacrylate 10% cream preparation, 50,20,10,5 gram/mus and carbendazim 50,20,10,5 gram/mus and spray clear water respectively, every processing triplicate, randomized arrangement, sub-district area are 25 square metres.Be selected in dispenser at dusk after the rainfall, artificial water spray was preserved moisture 15 days " Invest, Then Investigate " preventive effects three days.Grade scale is carried out the living chamber of surveying, the Ministry of Agriculture agriculture chemical examination institution and is compiled " pesticide field efficacy medicine test criterion ", is that inverse indicator is calculated preventive effect with the disease index.
Table 6 JS399 prevents and treats the 20th, 34 days investigation results (Nanjing, the 5-6 month in 2003) of head blight
Medicament Dosage 20d 34d
Average disease refers to Preventive effect (%) Average disease refers to Preventive effect (%)
JS399 5 0.3697 59.88 0.4858 50.00
10 0.3833 58.40 0.4068 58.11
20 0.2297 75.07 0.2203 77.13
50 0.1195 87.03 0.0837 90.90
Carbendazim 5 0.6321 31.39 0.7223 25.62
10 0.5482 40.50 0.5815 40.12
20 0.5797 37.08 0.5062 47.87
50 0.4090 55.61 0.3097 68.11
The disease of blank refers to be 0.9214 The disease of blank refers to be 0.9712
The sub-district, field is the screening test result show, 2-cyano group-3-amino-3-ethyl phenylacrylate to the preventive effect of gibberella saubinetii apparently higher than carbendazim; To wheat safety.

Claims (3)

1, the application of following formula: compound 2-cyano group-3-amino-3-ethyl phenylacrylate for preventing agronomic crop disease
Figure A2006101259210002C1
2, according to the application of claim 1, the pathogen of wherein said corps diseases is sickle-like bacteria, rest fungus, botrytis cinerea.
3, a kind of composition pesticide is characterized in that it contains compound 2-cyano group-3-amino-3-ethyl phenylacrylate as active component, forms with acceptable carrier on the agricultural chemicals.
CNB2006101259216A 2004-02-18 2004-02-18 Application of 2-cyano-3-amino-3-ethyl phenylacrylate for preventing agronomic crop disease Expired - Fee Related CN100435635C (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102715176A (en) * 2012-05-22 2012-10-10 安徽省农业科学院植物保护与农产品质量安全研究所 Bactericidal composition containing 2-cyano-3-amino-3-ethyl phenylacrylate and clorine-nalidixic-methyl
CN105594727A (en) * 2016-03-02 2016-05-25 扬州市邗江区农作物技术推广中心 Composition containing dinotefuran and phenamacril, preparation method and application

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3361451D1 (en) * 1982-03-05 1986-01-23 Fbc Ltd Fungicidal cyanopropenoates and compositions containing them
CN1160318C (en) * 2001-05-08 2004-08-04 江苏省农药研究所 2-cyano-3-substituted phenylacrylate compounds, compositions and their preparing prcess and application as disinfectant of agricultural crops

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102715176A (en) * 2012-05-22 2012-10-10 安徽省农业科学院植物保护与农产品质量安全研究所 Bactericidal composition containing 2-cyano-3-amino-3-ethyl phenylacrylate and clorine-nalidixic-methyl
CN105594727A (en) * 2016-03-02 2016-05-25 扬州市邗江区农作物技术推广中心 Composition containing dinotefuran and phenamacril, preparation method and application

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