CN100393211C - Application of 2-cydno-3-amino-3-phenylethyl acrylate for preventing and treating patty rice bakanae disease - Google Patents
Application of 2-cydno-3-amino-3-phenylethyl acrylate for preventing and treating patty rice bakanae disease Download PDFInfo
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- CN100393211C CN100393211C CNB2004100651456A CN200410065145A CN100393211C CN 100393211 C CN100393211 C CN 100393211C CN B2004100651456 A CNB2004100651456 A CN B2004100651456A CN 200410065145 A CN200410065145 A CN 200410065145A CN 100393211 C CN100393211 C CN 100393211C
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Abstract
The present invention provides the application of a compound, namely 2-cyano-3-amino-3-ethyl phenylacrylate in preventing and treating bakanae disease of paddy rice, and a synergistic pesticide composition of the compound and other bactericidal agents. The synergistic pesticide composition is prepared from the effective components of the 2-cyano-3-amino-3-ethyl phenylacrylate and a bactericidal agent and can be prepared into suspended seed treating agents, emulsible solutions and water dispersible granules. The application method of the synergistic pesticide composition comprises seed treatment or leaf surface spray. The synergistic pesticide composition can be used for effectively preventing and treating paddy rice diseases, such as bakanae disease of the paddy rice, etc., to improve the production yield and the quality of the paddy rice.
Description
Technical field
The present invention relates to the composition pesticide that compound 2-cyano group-3-amino-the 3-ethyl phenylacrylate is prevented and treated the application of bakanae disease of rice and contained this compound.Belong to the agriculture plant protection field.
Background technology
As compound 2-cyano group of the present invention-3-amino-3-ethyl phenylacrylate, CAS number is [39491-78-6], at U.S. chemical abstract CA 125:275357 report is arranged, and finds first and reports but its bio-bactericidal activity is the applicant of patent of the present invention
[1]Find after the bactericidal activity of this compound, carried out the research of fungicidal spectrum and bio-bactericidal activity, except the applicant at patent " 2-cyano group-3-amino-3-ethyl phenylacrylate in agricultural production as the application of bactericide "
[1]Outside the middle remarkable activity of describing of preventing and treating wheat scab, this compound does not appear in the newspapers with application to the bactericidal activity of bakanae disease of rice.
Bakanae disease of rice is common rice disease, Rice Production is threatened very big, and the general underproduction 10～20% is fallen ill when serious the underproduction more than 50%.In recent years along with the continuous expansion of japonica rice area and the popularization of non-irrigated seedling-cultivation technique, being on the rise of bakanae disease
[2]The method of preventing and treating bakanae disease on the domestic Rice Production is based on seed treatment, and medicament has: captan, and carbendazim is disliked the seedling spirit, bronopol, Prochloraz, the seed soaking spirit, fludioxonil, Japan also has fluorine bacterium azoles and pefurazoate etc.
[2]Because the control pharmacy variety is few, exist the problem that frequent medication easily produces resistance, so the control of rice bakanae disease needs pharmaceutical preparations.
Summary of the invention
The purpose of this invention is to provide the amino 3-ethyl phenylacrylate of compound 2-cyano group-3-and prevent and treat the application of bakanae disease of rice
Another object of the present invention provides the composition pesticide that contains above-claimed cpd.
Another object of the present invention provides the synergetic pesticide composition that contains above-claimed cpd and other bactericide, wherein it is an effective ingredient with 2-cyano group-3-amino-3-ethyl phenylacrylate and bactericide, the weight ratio of 2-cyano group-3-amino-3-ethyl phenylacrylate and bactericide is 1: 0.01～100, the optimum weight ratio of 2-cyano group-3-amino-3-ethyl phenylacrylate and bactericide is 1: 0.1～50, described bactericide is selected from Prochloraz, dithiocyano-methane, fludioxonil, tmtd hymexazo, carboxin, fluorine bacterium azoles, in the pefurazoate one or more, composition pesticide formulation are the suspension seed treatments, missible oil, water dispersion granule.
Through further investigation, find that this compound has excellent activity to bakanae disease of rice, and find when preventing and treating bakanae disease, to have synergistic effect, not only can enlarge fungicidal spectrum with the A group is bactericide compounded, but also can reduce working pressure, prolong the service life of new product.
We find 2-cyano group-3-amino-3-ethyl phenylacrylate, and (Chinese is general by name: 2-cyano-3-amino-3-phenylancryic acetate, No. the 024th, the agricultural marking-up of the whole nation pesticide standard Secretariat of technical committee (2004), call 2-cyano-3-amino-3-phenylancryic acetate in the following text) have the biologically active of control rice bakanae disease after, the research and development personnel just recognize the work of how giving full play to its effect and prolonging its service life.Through a large amount of research work, found to prevent and treat the pesticide synergistic composition of bakanae disease of rice, have exploitation and be worth.
The composition pesticide of 2-cyano-3-amino-3-phenylancryic acetate-containing can be a unitary agent, also can be complex preparation.The type of preparation can be suspension seed treatment, missible oil, water dispersion granule etc.When preventing and treating bakanae disease, can seed treatment, also can foliar spray; When control seeding stage bakanae disease, based on seed treatment, when control tillering stage and fringe phase during bakanae disease, based on foliar spray.
1, the bactericide 2-cyano-3-amino-3-phenylancryic acetate is an effective agent of preventing and treating bakanae disease of rice, to mycelia EC
50Be 0.4592 μ g/mL, EC
90Be 2.8195 μ g/mL.And Prochloraz is to the EC of mycelia
50Be 1.4645 μ g/mL, to 3.7574 μ g/mL of spore.From indoor activity analysis, 2-cyano-3-amino-3-phenylancryic acetate has high activity to bakanae disease of rice.
2, compound 2-cyano group of the present invention-3-amino-3-ethyl phenylacrylate is the bactericide of effectively preventing bakanae disease of rice, can mix with other bactericide to use or form composition and prevent and treat multiple diseases such as bakanae disease of rice, dried point knot worm.When preventing and treating bakanae disease of rice, the bactericide of compatibility can be one or more among the A group bactericide II to IX with it.A group bactericide II～IX:
The II Prochloraz, prochloraz, N-propyl group-N-[α-(2,4, the 6-Trichlorophenoxy) ethyl]-1H-imidazoles-1-formamide;
The III dithiocyano-methane, methane dithiocyanate, methene dithiocyano ester
The IV fludioxonil, fludioxonil, 4-(2,2-two fluoro-1,3-benzo dioxole-4-yl)-1-hydrogen-pyrroles-3-nitrile,
The V tmtd, thiram, tetramethyl thiuram disulfide
The VI hymexazo, hymexazol, 3-hydroxy-5-methyl base isoxazole
The VII carboxin, carboxin, 5,6-dihydro-2-methyl isophthalic acid, 4-oxygen thia-3-formyl is for aniline
VIII fluorine bacterium azoles, triflumizole, (E)-and 4-chloro-α, α, α-three fluoro-N-(1-imidazoles-1-1-base-α-third oxygen ethylidene) neighbour-toluidines
The IX pefurazoate, pefurazoate, penta-4-thiazolinyl-N-furfuryl group-TMSIM N imidazole-1-base carbonyl-DL high lactamine ester
A group bactericide is the known material of pesticide field, all can from
Http:// www.chinapesticide.gov.cnThe pesticide active ingredient inquiry confirms in the webpage.
By in composition pesticide, adding one or more bactericide of A group, make it can have the more activity of wide spectrum than independent 2-cyano-3-amino-3-phenylancryic acetate.In addition, it is emphasized that when 2-cyano-3-amino-3-phenylancryic acetate and other bactericide are used in combination, produced synergistic effect.The example that can be included in the fungicide compound in the present composition has: Prochloraz, dithiocyano-methane, fludioxonil, tmtd ， hymexazo, carboxin, fluorine bacterium azoles, pefurazoate etc.Because the mechanism of action of 2-cyano-3-amino-3-phenylancryic acetate is studied, and might be novel action mechanism, with known biocides be dissimilar, therefore, the medicament of the different mechanisms of action has produced synergistic effect each other.
3, in the composition pesticide of 2-cyano-3-amino-3-phenylancryic acetate-containing, one or more of the 2-cyano-3-amino-3-phenylancryic acetate of per 1 weight portion and 0.01～100 weight portion are taken from the compound of A group, and particularly 0.1～50.
4, the present invention also provides preparation of compositions method as defined above.
According to composition of the present invention, preferably contain 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 seed, plant, 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 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.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.
Bactericidal composition 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 product 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 acid 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 composition of the present invention is suspension seed treatment, missible oil, water-dispersible granules.Outside but emulsion concentrate desolventizes, when needs, contain cosolvent usually, 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.Granula is prepared into and has 10～100 orders (1.676～0.152mm) sizes, available agglomerating or injection technique preparation usually.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.
Embodiment
Formulation examples 1:20% suspending agent
20 parts of 2-cyano-3-amino-3-phenylancryic acetates
10 parts of ethylene glycol
5 parts of neopelexes
0.5 part of xanthans
4.5 parts of stabilizing agents
60 parts in water
Formulation examples 2:10% missible oil
10 parts of 2-cyano-3-amino-3-phenylancryic acetates
12 parts of Tween 80s
N, 3 parts of dinethylformamides
75 parts of dimethylbenzene
Formulation Example 3:40% water dispersible granules
40 parts of 2-cyano-3-amino-3-phenylancryic acetates
3 parts of stabilizing agents
12 parts of sldium lauryl sulfates
10 parts of Lignosites
35 parts of kaolin
Formulation Example 4:25% suspending agent
10 parts of 2-cyano-3-amino-3-phenylancryic acetates
15 parts of Prochlorazs
15 parts of ethylene glycol
15 parts of neopelexes
5 parts of xanthans
40 parts in water
Formulation Example 5:5% missible oil
3 parts of 2-cyano-3-amino-3-phenylancryic acetates
2 parts of dithiocyano-methanes
10 parts of tweens
N, 10 parts of dinethylformamides
75 parts of dimethylbenzene
Formulation Example 6:10% suspending agent
5 parts of 2-cyano-3-amino-3-phenylancryic acetates
5 parts of fludioxonils
15 parts of ethylene glycol
15 parts of neopelexes
5 parts of xanthans
55 parts in water
Formulation examples 7:20% suspending agent
10 parts of 2-cyano-3-amino-3-phenylancryic acetates
10 parts of fludioxonils
10 parts of ethylene glycol
5 parts of neopelexes
0.5 part of xanthans
4.5 parts of stabilizing agents
60 parts in water
Formulation examples 8:18% suspending agent
10 parts of 2-cyano-3-amino-3-phenylancryic acetates
8 parts of tmtd
10 parts of ethylene glycol
7 parts of neopelexes
0.5 part of xanthans
4.5 parts of stabilizing agents
60 parts in water
Formulation examples 9:15% suspending agent
5 parts of 2-cyano-3-amino-3-phenylancryic acetates
10 parts of hymexazos
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 examples 10:15% suspending agent
5 parts of 2-cyano-3-amino-3-phenylancryic acetates
10 parts of carboxins
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 examples 11:10% suspending agent
3 parts of 2-cyano-3-amino-3-phenylancryic acetates
7 parts of fluorine bacterium azoles
10 parts of ethylene glycol
5 parts of neopelexes
0.5 part of xanthans
4.5 parts of stabilizing agents
70 parts in water
Formulation examples 12:10.5% missible oil
10 parts of 2-cyano-3-amino-3-phenylancryic acetates
0.5 part of pefurazoate
10 parts of tweens
N, 10 parts of dinethylformamides
69.5 parts of dimethylbenzene
Formulation examples 13:22% missible oil
0.5 part of 2-cyano-3-amino-3-phenylancryic acetate
6.5 parts of dithiocyano-methanes
15 parts of pefurazoates
10 parts of tweens
N, 10 parts of dinethylformamides
58 parts of dimethylbenzene
Formulation examples 14:35% suspending agent
5 parts of 2-cyano-3-amino-3-phenylancryic acetates
20 parts of carboxins
10 parts of fluorine bacterium azoles
5 parts of ethylene glycol
10 parts of neopelexes
1.5 parts of xanthans
3.5 parts of stabilizing agents
45 parts in water
Formulation Example 15:25% suspending agent
10 parts of 2-cyano-3-amino-3-phenylancryic acetates
8 parts of Prochlorazs
2 parts of fludioxonils
15 parts of ethylene glycol
15 parts of neopelexes
5 parts of xanthans
40 parts in water
Formulation Example 16:25% suspending agent
10 parts of 2-cyano-3-amino-3-phenylancryic acetates
10 parts of tmtd
5 parts of pefurazoates
5 parts of ethylene glycol
5 parts of neopelexes
5 parts of xanthans
60 parts in water
Formulation Example 17:18.2% suspending agent
0.2 part of 2-cyano-3-amino-3-phenylancryic acetate
10 parts of tmtd
8 parts of pefurazoates
6.8 parts of ethylene glycol
10 parts of neopelexes
5 parts of xanthans
60 parts in water
Formulation Example 18:25% suspending agent
1 part of 2-cyano-3-amino-3-phenylancryic acetate
10 parts of tmtd
10 parts of pefurazoates
5 parts of ethylene glycol
9 parts of neopelexes
5 parts of xanthans
60 parts in water
Application example 1:
The fungicidal spectrum test of 2-cyano-3-amino-3-phenylancryic acetate.
Test method: contain toxic medium method.It is 20,2 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 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
2-cyano group-3-amino-3-ethyl phenylacrylate with concentration 20,2ug/ml to 4 kinds of pathogen isolated measurings, carrying out the fungicidal spectrum result of the test shows: drug concentration is 20ug/ml to the mycelial growth inhibition rate of wheat scab, cotton wilt, Phytophthora capsici disease, rice bakanae disease all greater than 85%, drug concentration is 2.0ug/ml to the inhibiting rate of wheat scab, Phytophthora capsici disease, the growth of bakanae disease of rice mycelia all greater than 70%, has greater activity.
Application example 2
2-cyano group-3-amino-3-ethyl phenylacrylate is to the bactericidal activity test of bakanae disease of rice
Adopt the colony diameter method.The medicament mother liquor is diluted to series concentration prepares the pastille medium, every ware is inoculated a bacterium dish, and mycelia faces up.26 ℃ are cultured to the contrast bacterium colony and are covered with culture dish 2/3rds when above, measure the colony diameter that each concentration is handled, and each handles 3 repetitions.Each bacterium colony is measured 2 times by the right-angled intersection method, represents the size of bacterium colony with its mean.Calculate the inhibition of medicament, set up virulence regression equation the thalli growth rate
[5], obtain EC
50, relative virus force.
The virulence of table 2 pair rice bakanae disease bacterium
| Medicament | The toxicity regression line | EC 50(μg/mL) | Relative virus force index |
| 2-cyano group-3-amino-3-ethyl phenylacrylate | Y＝5.5503+1.6261x | 0.4592 | 318.92 |
| Prochloraz | Y＝4.9346+1.1841x | 1.4645 | 100 |
| Dithiocyano-methane | Y＝4.0261+3.0249x | 9.2445 | 15.94 |
2-cyano group-3-amino-3-ethyl phenylacrylate has excellent activity to bakanae disease of rice.Kind Prochloraz commonly used, dithiocyano-methane isoreactivity want high.
Application example 3
2-cyano group-3-amino-3-ethyl phenylacrylate and Prochloraz, dithiocyano-methane etc. are composite to have synergistic effect
Adopt the colony diameter method.The medicament mother liquor is diluted to series concentration prepares the pastille medium, every ware is inoculated a bacterium dish, and mycelia faces up.26 ℃ are cultured to the contrast bacterium colony and are covered with culture dish 2/3rds when above, measure the colony diameter that each concentration is handled, and each handles 3 repetitions.Each bacterium colony is measured 2 times by the right-angled intersection method, represents the size of bacterium colony with its mean.Calculate medicament to the inhibiting rate of thalli growth rate, synergistic effect etc.
Table 3 2-cyano group-3-amino-3-ethyl phenylacrylate, Prochloraz active testing
As can be seen from Table 3,2-cyano group-3-amino-3-ethyl phenylacrylate and Prochloraz, the multiple ester of dithiocyano-methane all have synergistic effect.
List of references
[1] Wang Fengyun, Xu Shangcheng, Ni Jueping etc., the application of the amino 3-ethyl phenylacrylate for preventing agronomic crop disease of 2-cyano group-3-, application number: 200410014097.8
[2] product is wished dragon, Dinke heavily fortified point, Tan Genjia, plant protection system of Agricultural University Of Anhui, the progress of bakanae disease of rice, Anhui agricultural science, 2002,30 (6): 880-883
Claims (3)
1. composition pesticide, wherein it is an active ingredient with the 2-cyano group-3-amino-3-ethyl phenylacrylate of formula (I) and in bactericide prochloraz, fluorine bacterium azoles or the pefurazoate one or more, wherein the weight ratio of 2-cyano group-3-amino-3-ethyl phenylacrylate and above-mentioned bactericide is 1: 0.01～100
2. composition pesticide according to claim 1, wherein the weight ratio of 2-cyano group-3-amino-3-ethyl phenylacrylate and above-mentioned bactericide is 1: 0.1～50.
3. composition pesticide according to claim 1, its formulation are suspension seed treatment, missible oil or water dispersion granule.
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|---|---|---|---|
| CNB2004100651456A CN100393211C (en) | 2004-10-27 | 2004-10-27 | Application of 2-cydno-3-amino-3-phenylethyl acrylate for preventing and treating patty rice bakanae disease |
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| CNB2004100651456A CN100393211C (en) | 2004-10-27 | 2004-10-27 | Application of 2-cydno-3-amino-3-phenylethyl acrylate for preventing and treating patty rice bakanae disease |
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| CN100393211C true CN100393211C (en) | 2008-06-11 |
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| CN102302005B (en) * | 2011-10-11 | 2013-08-07 | 陕西上格之路生物科学有限公司 | Application of JS399-19 (2-cyano-3-amino-3-phenylacrylic acetate) in preventing and controlling wheat take-all diease |
| CN103749479B (en) * | 2012-07-30 | 2016-04-13 | 陕西上格之路生物科学有限公司 | The bactericidal composition of a kind of 2-cyano-3-amino-3-phenylancryic acetate-containing and acid amide fungicides |
| CN103141482B (en) * | 2013-02-04 | 2014-08-27 | 安徽省农业科学院植物保护与农产品质量安全研究所 | Sterilization compound containing JS399-19 and mepanipyrim |
| CN104094942B (en) * | 2014-06-30 | 2016-09-07 | 中国水稻研究所 | A kind of 2-cyano-3-amino-3-phenylancryic acetate-containing and hymexazol composition pesticide |
| CN104186525A (en) * | 2014-08-01 | 2014-12-10 | 海南正业中农高科股份有限公司 | Bactericidal composition containing methylene dithiocyanate and strobilurin components |
| CN104137848B (en) * | 2014-08-07 | 2016-06-08 | 海南正业中农高科股份有限公司 | A kind of containing the fungicidal composition of dithiocyano-methane and prochloraz |
| CN104770366A (en) * | 2015-03-25 | 2015-07-15 | 安徽省农业科学院植物保护与农产品质量安全研究所 | Sterilization composition containing JS399-19 and benzamide |
| CN104719307A (en) * | 2015-03-25 | 2015-06-24 | 安徽省农业科学院植物保护与农产品质量安全研究所 | Fungicidal composition containing probenazole and 2-cyano-3-amino-3-ethyl phenylacrylate |
| CN105494359B (en) * | 2016-02-23 | 2017-11-21 | 南京农业大学 | A kind of composite bactericide for preventing and treating wheat scab and its application |
| CN105594727B (en) * | 2016-03-02 | 2018-01-12 | 扬州市邗江区农作物技术推广中心 | Composition, Preparation method and use containing MTI-446 and 2-cyano-3-amino-3-phenylancryic acetate |
| CN105724392B (en) * | 2016-03-28 | 2017-12-26 | 南京农业大学 | A kind of purposes of composition pesticide containing 2-cyano-3-amino-3-phenylancryic acetate and kind bacterium azoles in bakanae disease of rice is prevented and treated |
| CN106614713A (en) * | 2016-12-16 | 2017-05-10 | 张宗斌 | Corn seed treatment agent containing phenamacril and chlorpyrifos |
| CN107125252A (en) * | 2017-07-03 | 2017-09-05 | 南京农业大学 | A kind of bactericidal composition containing 2-cyano-3-amino-3-phenylancryic acetate and captan |
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