CN102007916B - Agricultural and gardening antifungal composition - Google Patents
Agricultural and gardening antifungal composition Download PDFInfo
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- CN102007916B CN102007916B CN 201010523940 CN201010523940A CN102007916B CN 102007916 B CN102007916 B CN 102007916B CN 201010523940 CN201010523940 CN 201010523940 CN 201010523940 A CN201010523940 A CN 201010523940A CN 102007916 B CN102007916 B CN 102007916B
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Abstract
The invention relates to an agricultural and gardening antifungal composition, in particular to an antifungal composition containing benzamidoxime derivatives and triazoles. The composition comprises an active component A and an active component B), wherein the active component A) is one or more benzamidoxime derivatives represented by a formula (I); and the active component B) is one or more triazoles represented by a formula (II).
Description
Technical field
A kind of agricultural of the present invention and garden antifungal composition relate to the Fungicidal composition, particularly a kind of benzamidoxime derivative and mycocidal bactericidal composition of triazole type of containing that a kind of agricultural and gardening are used.
Background technology
In recent years, because single drug and the medication of non-science, cause many diseases that the agricultural chemicals of current use has been produced resistance, as the powdery mildew of cereal, melon, drupe class, grape, flowers etc., become a great problem of chemical control.Simultaneously frequent dispenser causes peasant burden to increase the weight of and increasing environmental pollution again.Therefore be badly in need of the antifungal new varieties of efficient, low toxicity, environmental protection.
Be the sustainable development of assurance agricultural production and the service life that prolongs medicament, seek the method for preventing and treating that has prevention and delaying drug resistance generation and can do with the resistance pathogen and seem particularly important.
Preventing and treating pathogen with the novel pesticide that does not have cross resistance is a good solution.But develop a novel pesticide at present and need screen 10,000-1.2 ten thousand compounds, hundred million dollars of expensive 1.2-1.5, the construction cycle is 5-10, is difficult to catch up with the speed that the pathogen resistance produces.Other method such as crop allocation adjustment, different agricultural chemicals are rotated etc., in the process of practical operation, are difficult to really play obvious effects.
By the preparation of the benzamidoxime derivative of formula (I) expression and to the effect of harmful germ by document known (JP2696342, WO96/19442, CN1170404).
Triazole type antifungal bactericidal mechanism principle is very complicated, mainly is the biosynthesis that suppresses the thalline ergosterol, thereby the growth, the growth of mycelia and the formation of spore that suppress or disturb thalline to adhere to spore and haustorium.Better to the powdery mildew effect, but the risk that exists resistance to strengthen.
The mycocidal combination of benzamidoxime derivative and triazole type is disclosed among the EP1625790.Document shows that said composition has obvious synergistic effect.But its disclosed benzamidoxime derivative and the mycocidal percentage by weight of triazole type are 1: 0.01-1,000, preferred 1: 1-100, scope is too wide, and is inapplicable when agricultural is specifically used.
Summary of the invention
The objective of the invention is at above-mentioned weak point, the Fungicidal composition that provides a kind of agricultural and gardening to use uses on a kind of suitable agricultural, disease is had the efficient bactericidal composite that synergistic effect is arranged of outstanding control efficiency.
By a large amount of biologicall test screenings, found the mass ratio of the best when benzamidoxime derivative and triazole class compounds are composite.When benzamidoxime derivative and triazole type antifungal were composite, mass ratio was 1: 1-1:, be preferably 1 at 15 o'clock: 5-1: 10 o'clock, and to control efficiency the best of disease.
The Fungicidal composition that a kind of agricultural and gardening are used is characterized in that comprising active component A) a kind of or
Multiple benzamidoxime derivative by formula (I) expression
Wherein, R
1It is straight or branched C1-C4 alkyl; By general formula R
3CH
2The group of expression, wherein R
3Be selected from C
3-C
8Cycloalkyl, C
1-C
3Haloalkyl, C
1-C
3Alkoxyl, C
1-C
3Alkylthio group, C
1-C
3Alkyl sulphinyl, C
1-C
3Alkyl sulphonyl, C
1-C
3Alkoxyl, cyano group, amino, C
1-C
3Alkyl monosubstituted amino, C
1-C
3Dialkyl amido, acyl amino and cyano group; C
2-C
4Thiazolinyl or C
2-C
4Alkynyl;
R
2Be randomly to have substituent phenyl or randomly have substituent heterocycle;
X
1Be C
1-C
4Haloalkyl;
X
2, X
3, X
4And X
5Be respectively hydrogen, halogen, C separately
1-C
4Alkyl, C
1-C
4Haloalkyl, C
1-C
4Alkoxyl, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio group, C
1-C
4Alkyl sulphinyl, C
1-C
4Alkyl sulphonyl, nitro, amino or C
1-C
4Alkyl oxycarbonyl amino;
r
1And r
2Be respectively hydrogen, halogen, C separately
1-C
4Alkyl, C
1-C
4Haloalkyl, C
1-C
4Alkoxyl, C
1-C
4Alkylthio group or amino, perhaps r
1And r
2Form carbonyl together,
With active component B) one or more triazole class compounds by formula (II) expression
R wherein
1Represent phenyl, 4-chlorphenyl, 4-chlorobenzene ethyl, 4-fluorite phenyl, 2,4-dichlorophenyl, or 4-chlorophenoxy;
R
2Represent the n-butyl, the tert-butyl, phenyl, 2-fluorite phenyl or molecular formula (III):
And R
3Represent hydroxyl, oxygen root or cyanogen root,
Described active component A) and mass ratio B) be 1: 1-1: 15.
The Fungicidal composition that described agricultural and gardening are used, the benzamidoxime derivative that wherein said active component A is represented by formula I, R
1Be C
1-C
4The C that replaces
3-C
5Cycloalkyl; R
2Be phenyl; X
1Be halogen, C
1-C
4Alkylhalide group or C
1-C
4The oxyhalogen base; X
2, X
3, X
4, X
5Be respectively hydrogen base or halogen; r
1And r
2Be hydrogen.
The Fungicidal composition that described agricultural and gardening are used, the wherein said preferred cyflufenamid of being represented by formula I of benzamidoxime derivative.
The Fungicidal composition that described agricultural and gardening are used, wherein said active component B be by the triazole class compounds that formula II represents, selects in Tebuconazole, cyproconazole, triticonazole, own azoles alcohol, Flutriafol, nitrile bacterium azoles, the Difenoconazole one or more for use.
The Fungicidal composition that described agricultural and gardening are used wherein comprises active component cyflufenamid and Tebuconazole.
The Fungicidal composition that described agricultural and gardening are used wherein comprises active component cyflufenamid and Difenoconazole.
The Fungicidal composition that described agricultural and gardening are used wherein comprises active component cyflufenamid and nitrile bacterium azoles.
The Fungicidal composition that described agricultural and gardening are used wherein comprises active component cyflufenamid and Flutriafol.
The Fungicidal composition that described agricultural and gardening are used wherein comprises active component cyflufenamid and triticonazole.
The Fungicidal composition that described agricultural and gardening are used wherein comprises active component cyflufenamid and own azoles alcohol.
The Fungicidal composition that described agricultural and gardening are used wherein comprises active component cyflufenamid and cyproconazole.
The Fungicidal composition that described agricultural and gardening are used, wherein active component A) and mass ratio B) be preferably 1: 5-1: 10.
The Fungicidal composition that described agricultural and gardening are used, wherein active component A) and the percentage composition that accounts for composition of weight B) be 5-20%
The Fungicidal composition that described agricultural and gardening are used, wherein active component A) and the percentage composition that accounts for composition of weight B) be preferably 8-15%.
The Fungicidal composition that described agricultural and gardening are used, active component A) and B) and known auxiliary agent and excipient be re-dubbed any one formulation that allows on the agricultural chemicals, selecting formulation for use is wetting powder, water dispersible granules, suspending agent, aqueous emulsion.
The application of the Fungicidal composition that described a kind of agricultural and gardening are used in diseases such as each fruit trees powdery mildew of control, vegetables powdery mildew, cereal class powdery mildew, flowers powdery mildew.
Table 1 has provided the compound of the preferred benzamidoxime derivative of part:
(r
1r
2＝H)
Table 1(Continued)
The preferred cyflufenamid of described benzamidoxime derivative (cyflufenamid); In the preferred Tebuconazole of described triazole type antifungal, cyproconazole, triticonazole, own azoles alcohol, Flutriafol, nitrile bacterium azoles, the Difenoconazole one or more.
The present composition can be prepared into known method and be fit to the formulation that agricultural is used, and wherein the weight percentage of active component benzamidoxime derivative and triazole class compounds accounts for the 5-20% of composition, preferred 8-15%.
The adjuvant that uses in the composition of the present invention comprises that dispersant, wetting agent, antifreezing agent, bleeding agent etc. and other are of value to the known substance that active ingredient is stablized and drug effect is brought into play in storing and using, all be the various compositions of using or allow use in the pesticidal preparations always, be not particularly limited, concrete composition and consumption require to determine by simple experiment according to prescription.
Product described in the invention can the finished product preparation form provide, and namely each material mixes in the composition, and the composition of composition also can provide with single agent form, directly directly mixes in bucket or jar before the use, is diluted to required concentration then.
Bactericidal composition of the present invention is mainly used in preventing and treating the application in the diseases such as each fruit trees powdery mildew, vegetables powdery mildew, cereal class powdery mildew, flowers powdery mildew.
Compared with prior art, the beneficial effect of the present invention's generation is:
(1) the present invention is on a large amount of experiment basis, and the proportioning of the best when the combination of benzamidoxime derivative and triazole class compounds is provided is conducive to reach best drug effect when agricultural or flowers application said composition;
(2) the present invention accounts for the quality percentage composition of the best of composition when the combination of benzamidoxime derivative and triazole class compounds is provided on a large amount of experiment basis, reduces the field dosage, effectively reduces environmental pollution and residue of pesticide, reduces and produces and use cost;
Embodiment
In order to make purpose of the present invention, technical scheme and advantage clearer, the present invention describes with following specific embodiment, but the present invention is limited to these examples absolutely not.
The agricultural chemicals of different cultivars shows three kinds of type of action: summation action, synergistic effect and antagonism after mixing usually.But be specially which kind of effect, unpredictable, have only by a large amount of experiments and just can know.Compound synergic is well filled a prescription, owing to obviously improved actual control efficiency, reduced the usage amount of agricultural chemicals, thereby delayed the generation of disease drug resistance greatly, and be the important means of integrated control.
The present composition is active ingredient with benzamidoxime derivative and triazole bactericidal agent, the combination antagonism property of medicine has obvious role in synergism between them, and be not only the simple addition of two kinds of medicament effects, specifically be illustrated with following biologicall test example.
Biologicall test example 1: cyflufenamid and Tebuconazole composite toxicity test and proportioning screening at wheat powdery mildew
Laboratory reference " pesticide bioassay technology " (old spring chief editor, publishing house of Beijing Agricultural University publishes), and " agricultural chemicals indoor bioassay experiment criterion NY/T1156.2-2006 ". this experiment adopts the wheat powdery mildew dish to plant determination method.On the basis of preliminary experiment, select 2 leaf periods, the consistent melon seedling of growing way, write tag number, insert in the potted plant seedling basin with permanent pen, discharging according to the order of sequence, adopt the foliar spray method, medicament is sprayed on the seedling leaf, will tries material after spraying is handled and in fume hood or greenhouse, dry in the shade and inoculate behind the 24h.Cultivate 7d investigation prevention result in the greenhouse, grade scale is carried out State Standard of the People's Republic of China " pesticide field efficacy medicine test criterion () ", calculates control efficiency with disease index, carries out statistical analysis with the DPS data processing software, calculates the EC of each medicament
50, press the abundant method of Sun Yun then and calculate co-toxicity coefficient (CTC).
When CTC≤80, then compositions table reveals antagonism, and when 80＜CTC＜120, then compositions table reveals summation action, and when CTC 〉=120, then compositions table reveals synergistic effect.
Actual measurement toxicity index (ATI)=(standard medicament EC
50/ reagent agent EC
50) X100
The percentage composition of B in percentage composition+B medicament toxicity index X mixture of A in theoretical toxicity index (TTI)=A medicament toxicity index X mixture
Co-toxicity coefficient (CTC)=[mixture actual measurement toxicity index (the ATI)/theoretical toxicity index (TTI) of mixture] X100
Table 2 cyflufenamid and Tebuconazole are to Toxicity Determination and the proportioning screening of wheat powdery mildew
The result shows, cyflufenamid and Tebuconazole are at proportioning 1: 1-1: obvious synergistic effect is arranged between 15, and co-toxicity coefficient is more than 120.
Biologicall test example 2: cyflufenamid and Difenoconazole composite toxicity test and proportioning screening to apple mildew
Experimental subjects: apple mildew experiment
Test is with reference to " pesticide bioassay technology " (old spring chief editor, publishing house of Beijing Agricultural University publishes), and " agricultural chemicals indoor bioassay experiment criterion NY/T1156.2-2006 ". and the potted plant determination method of apple mildew is adopted in this experiment.On the basis of preliminary experiment, select to be in 3 leaf phases, the seedling of growing way unanimity, write tag number, insert in the potted plant seedling basin with permanent pen, the foliar spray method is adopted in discharging according to the order of sequence, medicament is sprayed on the seedling leaf, will tries material after spraying is handled and in fume hood or greenhouse, dry in the shade and inoculate behind the 24h.In the greenhouse, cultivate 7d investigation prevention effect, grade scale is carried out State Standard of the People's Republic of China " pesticide field efficacy medicine test criterion () ", calculate control efficiency with disease index, carry out statistical analysis with the DPS data processing software, calculate the EC50 of each medicament, press the abundant method of Sun Yun then and calculate co-toxicity coefficient (CTC).
Table 3 cyflufenamid and Difenoconazole are to Toxicity Determination and the proportioning screening of apple mildew
The result shows, cyflufenamid and Difenoconazole are at proportioning 1: 1-1: obvious synergistic effect is arranged between 10, and co-toxicity coefficient is more than 120.
Biologicall test embodiment 3: cyflufenamid and own azoles alcohol composite toxicity test and proportioning screening to grape powdery mildew
As embodiment 1 and 2, adopt spray-on process, the cyflufenamid of mensuration different proportion and own azoles alcohol compound drug are to the indoor virulence of grape powdery mildew.
Table 4 cyflufenamid and own azoles alcohol are to Toxicity Determination and the proportioning screening of grape powdery mildew
The result shows, cyflufenamid and own azoles alcohol are at proportioning 1: 1-1: obvious synergistic effect is arranged between 14, and co-toxicity coefficient is more than 120.
Biologicall test example 4: cyflufenamid and myclobutanil compositional are to Toxicity Determination and the proportioning screening of powdery mildew of strawberry bacterium
Adopt spray-on process, the cyflufenamid of mensuration different proportion and myclobutanil compositional medicament are to the indoor virulence of powdery mildew of strawberry.
Table 5 cyflufenamid and own azoles alcohol are to Toxicity Determination and the proportioning screening of powdery mildew of strawberry
The result shows, cyflufenamid and nitrile bacterium azoles are at proportioning 1: 1-1: obvious synergistic effect is arranged between 8, and co-toxicity coefficient is more than 120.
Bactericidal composition of the present invention can be prepared into known method and be fit to any one formulation that agricultural goes up use, and reasonable formulation is wetting powder, water dispersible granules, suspending agent and aqueous emulsion.Below describe with specific embodiment.Percentage all is weight percentage in all prescriptions.The processing technology of the various preparations of the present composition is prior art, can change to some extent according to this situation together.
Embodiment 1:12% cyflufenamid+tebuconazole suspension concentrates
Cyflufenamid 2%
Tebuconazole 10%
Methyl naphthalene sulfonate formaldehyde condensate 10%
Xanthans 1%
Bentonite 1%
Glycerine 5%
Water complements to 100%
The ratio of each component such as active component, dispersant, wetting agent and water according to prescription mixed, after grinding and/or high speed shear, obtain 11% cyflufenamid+tebuconazole suspension concentrates.
This embodiment is used for the control wheat powdery mildew.By 2500 extraordinarily water dilution sprayings, 7 days control efficiency is 91.3% behind the medicine with 12% cyflufenamid+tebuconazole suspension concentrates.The single agent of 100g/L cyflufenamid SC and 25% tebuconazole aqueous emulsion are used with quadrat method and are used by 1000 times of dilutions, and 7 days preventive effect is respectively 71% and 70% behind the medicine.The synergistic effect of the composite back of cyflufenamid and Tebuconazole is obvious, to the preventive effect of wheat powdery mildew significantly better than single agent; Because pharmacy control efficacy improves, the amount ratio of compound drug active ingredient uses obviously separately and reduces, thereby has alleviated peasant's medication burden, has also alleviated the pollution to environment.
Embodiment 215% cyflufenamid+Difenoconazole wetting powder
Cyflufenamid 7.5%
Difenoconazole 7.5%
Lauryl sodium sulfate 2%
Sodium lignin sulfonate 5%
White carbon 10%
Kaolin complements to 100%
Ratio composition in prescription such as active component, various auxiliary agent and filler is mixed, after ultrafine crusher is pulverized, namely obtain 15% cyflufenamid+Difenoconazole wetting powder.
This embodiment is used for preventing and treating apple mildew.By 4000 extraordinarily water dilution sprayings, 7 days control efficiency is 91.2% behind the medicine with 15% cyflufenamid+Difenoconazole wetting powder.100g/L cyflufenamid SC is by 1000 times of dilutions, and 10% Difenoconazole aqueous emulsion is used with quadrat method and used by 1000 times of dilutions, and 7 days preventive effect is respectively 85.3% and 80.5% behind the medicine.The synergy of the composite back of cyflufenamid and Difenoconazole is obvious, to the preventive effect of apple mildew significantly better than single agent; Because pharmacy control efficacy height, the amount ratio of compound drug active ingredient use obviously minimizing separately, thereby reduced the pollution to environment.
Embodiment 320% cyflufenamid+nitrile bacterium azoles aqueous emulsion
Cyflufenamid 1.25%
Nitrile bacterium azoles 18.75%
N-methyl pyrrolidone 15%
Calcium dodecyl benzene sulfonate 5%
The newborn 600# 5% of farming
Water complements to 100%
Former medicine, solvent, emulsifier are added together, make and be dissolved into even oil phase; With water-soluble component and the mixed water that gets of water; Under high-speed stirred, oil phase is mixed with water, make 20% cyflufenamid+nitrile bacterium azoles aqueous emulsion.
This embodiment is used for the control powdery mildew of strawberry.With 20% cyflufenamid+nitrile bacterium azoles aqueous emulsion by 5000 extraordinarily water dilution sprayings, behind the medicine 7 days control efficiency be 88.5%.50g/L cyflufenamid aqueous emulsion by 1000 extraordinarily water dilutions, 25% nitrile bacterium azoles aqueous emulsion is by 1000 extraordinarily water dilutions.With using with quadrat method, 7 days preventive effect is respectively 79.4% and 43.2% behind the medicine.Synergistic effect is obvious behind cyflufenamid and the myclobutanil compositional, and significantly better than single agent, and the consumption of active ingredient obviously reduces to the preventive effect of apple mildew.
Embodiment 45% cyflufenamid+diniconazole water dispersible granule
Cyflufenamid 1.5%
Own azoles alcohol 3.5%
Sodium lignin sulfonate 4%
Lauryl sodium sulfate 5%
Urea 5%
Kaolin complements to 100%
Active component, dispersant, wetting agent, disintegrant and the filler ratio in prescription is mixed, be ground into wetting powder through air-flow, add a certain amount of water mixing extruding again and make material.Obtain 5% cyflufenamid+diniconazole water dispersible granule after the drying screening.
This embodiment is used for the control grape powdery mildew.With the extraordinarily water dilution spraying of 5% cyflufenamid+diniconazole water dispersible granule 1000,7 days control efficiency is 83.5% behind the medicine.50g/L cyflufenamid aqueous emulsion is by 500 extraordinarily water dilutions, and 10% hexaconazole suspending agent is by 500 extraordinarily water dilutions.With using with quadrat method, 7 days preventive effect is respectively 78% and 76.5% behind the medicine.The composite back synergistic effect of cyflufenamid and own azoles alcohol is obvious, and significantly better than single agent, and the consumption of active ingredient obviously reduces to the preventive effect of grape powdery mildew.
Embodiment 58.8% cyflufenamid+Flutriafol suspending agent
Cyflufenamid 0.8%
Flutriafol 8%
Methyl naphthalene sulfonate formaldehyde condensate 10%
Xanthans 1%
Bentonite 1%
Glycerine 5%
Water complements to 100%
The ratio of each component such as active component, dispersant, wetting agent and water in prescription mixed, after grinding and/or high speed shear, obtain 8% cyflufenamid+Flutriafol suspending agent.
This embodiment is used for the control beet powdery mildew.By 2000 extraordinarily water dilution sprayings, 10 days control efficiency is 93.5% behind the medicine with 8.8% cyflufenamid+Flutriafol suspending agent.100g/L cyflufenamid suspending agent is by 1000 times of liquid thin ups, and 25% Flutriafol SC is by 1000 times of liquid thin ups.The use that uses the same method, 7 days preventive effect is respectively 84.3% and 79.4% behind the medicine.The synergistic effect of the composite back of cyflufenamid and Flutriafol is obvious, and significantly better than single agent, and the consumption of active ingredient obviously reduces to the preventive effect of beet powdery mildew.
Embodiment 610% cyflufenamid+triticonazole suspending agent
Cyflufenamid 2%
Triticonazole 8%
Methyl naphthalene sulfonate formaldehyde condensate 5%
Xanthans 1%
Bentonite 1%
Glycerine 5%
Water complements to 100%
The ratio of each component such as active component, dispersant, wetting agent and water in prescription mixed, after grinding and/or high speed shear, obtain 10% cyflufenamid+triticonazole suspending agent.
This embodiment is used for control rose powdery mildew.10% cyflufenamid+triticonazole suspending agent is pressed 2000 extraordinarily water dilution sprayings.7 days preventive effect is 92.8% behind the medicine.1000 times of 100g/L cyflufenamid SC thin ups, 1000 times of 25% triticonazole SC thin ups.The use that uses the same method, 7 days preventive effect is respectively 83.5% and 80.5% behind the medicine.The synergistic effect of the composite back of cyflufenamid and triticonazole is obvious, and significantly better than single agent, and the consumption of active ingredient obviously reduces to the preventive effect of rose powdery mildew.
Claims (4)
1. an agricultural and garden antifungal composition is characterized in that comprising active component A) cyflufenamid and active component B) be selected from a kind of in Tebuconazole, own azoles alcohol, nitrile bacterium azoles or the Difenoconazole; Wherein
The mass ratio of cyflufenamid and Tebuconazole is 1: 1-1: 15;
The mass ratio of cyflufenamid and Difenoconazole is 1: 1-1: 10;
The mass ratio of cyflufenamid and own azoles alcohol is 1: 1-1: 14;
The mass ratio of cyflufenamid and nitrile bacterium azoles is 1: 1-1: 8.
2. Fungicidal composition according to claim 1, wherein active component A) and the percentage composition that accounts for composition of weight B) be 5-20%.
3. according to the Fungicidal composition of claim 1 or 2, active component A) and B) and known auxiliary agent and excipient be re-dubbed wetting powder, water dispersible granules, suspending agent or the aqueous emulsion that allows on the agricultural chemicals.
4. the application of Fungicidal composition according to claim 1 and 2 in each fruit trees powdery mildew of control, vegetables powdery mildew, cereal class powdery mildew, flowers powdery mildew disease.
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| EP3616513A4 (en) * | 2017-04-28 | 2021-01-20 | Nippon Soda Co., Ltd. | Suspoemulsion |
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| CN102318607A (en) * | 2011-09-21 | 2012-01-18 | 海利尔药业集团股份有限公司 | Complexly-formulated high-efficient germicidal composition |
| CN102308808A (en) * | 2011-10-10 | 2012-01-11 | 海利尔药业集团股份有限公司 | Antibacterial composition containing cyflufenamid and triazole bactericides |
| CN104094940B (en) * | 2014-07-28 | 2016-03-16 | 陕西上格之路生物科学有限公司 | A kind of bactericidal composition containing cyflufenamid and triazole bactericidal agent |
| CN106922701A (en) * | 2015-12-30 | 2017-07-07 | 江苏龙灯化学有限公司 | A kind of bactericidal composition |
| CN109717191A (en) * | 2017-10-31 | 2019-05-07 | 江苏龙灯化学有限公司 | A kind of application of the bactericidal composition containing cyflufenamid and Tebuconazole |
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| WO2008095890A2 (en) * | 2007-02-05 | 2008-08-14 | Basf Se | Fungicidal mixtures comprising substituted 1-methylpyrazol-4-ylcarboxanilides |
| EP2201839A1 (en) * | 2007-04-25 | 2010-06-30 | Syngenta Participations AG | Fungicidal compositions |
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| DE69921702T2 (en) * | 1998-04-30 | 2005-12-15 | Nippon Soda Co. Ltd. | A fungicidal composition for agriculture and horticulture containing a benzamidoxime compound and a cinnamic acid derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008095890A2 (en) * | 2007-02-05 | 2008-08-14 | Basf Se | Fungicidal mixtures comprising substituted 1-methylpyrazol-4-ylcarboxanilides |
| EP2201839A1 (en) * | 2007-04-25 | 2010-06-30 | Syngenta Participations AG | Fungicidal compositions |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP3616513A4 (en) * | 2017-04-28 | 2021-01-20 | Nippon Soda Co., Ltd. | Suspoemulsion |
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