CN105724398B - A kind of Fungicidal composition and its application - Google Patents
A kind of Fungicidal composition and its application Download PDFInfo
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Abstract
The invention belongs to disinfectant use in agriculture field, specifically a kind of Fungicidal composition.Composition is two kinds of active components of A, B；Wherein, the weight ratio between two component of component A and component B is 1:100~100:1；Component A is selected from following general formula compound represented:
Description
Technical field
The invention belongs to disinfectant use in agriculture field, specifically a kind of Fungicidal composition.
Background technique
It is reported in patent WO2011116671 " a kind of substituted diphenylamine amine compound and its preparation and application " following logical
Formulas I compound represented has activity well to a variety of fungal diseases.
Wherein, R1=H, R2=Cl, R3=NO2、R4=R8=Cl, R5=R7=H, R6=NO2Compound A1
(compound 43 in WO2011116671) has activity well to multiple diseases.
The fungicide of amides such as metalaxyl, dimethomorph, flumorph, fluopicolide are widely used in agricultural production
The obligate fungicide of one kind to Oomycete fungal disease with prominent control efficiency.Because such fungicide has good interior suction
Property, and action site is single, and after part kind such as metalaxyl, M 9834 are reused for a long time, germ drug resistance is very
Seriously, field efficacy is remarkably decreased.
In the practice of fungicide application, people will often have different role mechanism or different role side consciously
The fungicide of formula is used in mixed way, and improves the protection effect of medicament, and also to achieve the purpose that saving of work and time.
Summary of the invention
The purpose of the present invention is to provide a kind of Fungicidal composition and its applications, to delay the production of pathogen drug resistance
It is raw, extend the service life of medicament.
To achieve the above object, the invention adopts a technical scheme as:
A kind of Fungicidal composition, containing two kinds of active components of A, B, the weight ratio between two component of component A and component B is
1:100~100:1；
Component A is selected from following general formula I compound represented:
In formula:
R1Selected from hydrogen, C1-C12Alkyl, C3-C12Naphthenic base, halogenated C1-C12Alkyl, C1-C12Alkyl-carbonyl, halogenated C1-C12
Alkyl-carbonyl, C1-C12Alkoxy carbonyl, C1-C12Alkyl amino-carbonyl, C1-C12Alkylthio group, halogenated C1-C12Alkylthio group, C1-C12
Alkyl sulphonyl, C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkoxy C1-C12Alkyl-carbonyl, C1-C12Alkoxy carbonyl C1-C12
Alkyl, C1-C12Alkyl amino sulfenyl, C2-C12Dialkyl amido sulfenyl or CO-X-CO2R9, wherein X is selected from (CHR9)n、CR9=
CR10Or C6H4, n=1-6；
R2Selected from halogen, halogenated C1-C12Alkyl, C1-C12Alkoxy, halogenated C1-C12Alkoxy, C1-C12Alkyl amino, halogen
For C1-C12Alkyl amino, C1-C12Alkylthio group, halogenated C1-C12Alkylthio group, C1-C12Alkyl sulphonyl, C3-C12Naphthenic base, C2-C12
Dialkyl amido, C3-C12Alkenyloxy group, halogenated C3-C12Alkenyloxy group, C3-C12Alkynyloxy group, halogenated C3-C12Alkynyloxy group, C1-C12Alkyl
Carbonyl oxygroup, C1-C12Alkyl-carbonyl-amino, C1-C12Alkyl sulphonyl oxygroup, C1-C12Alkoxy C1-C12Alkoxy, C1-C12Alkane
Epoxide carbonyl C1-C12It is alkoxy, unsubstituted or by 1-5 R11Substituted following radicals aryloxy group, fragrant amino, arylmethyl oxygen
Base, arylmethyl amino, heteroaryl oxygroup or heteroaryl amino, and by R11When substituted number is greater than 1, R11It may be the same or different；
R3Selected from hydrogen, halogen, nitro, cyano, C (=O) NR9R10, C (=S) NR9R10、C1-C12Alkyl amino-carbonyl, C1-
C12Alkoxy carbonyl, halogenated C1-C12Alkyl or C1-C12Alkyl sulphonyl；
R4、R8What be may be the same or different is selected from hydrogen, halogen, cyano, nitro, C (=O) NR9R10、C1-C12Alkyl, halogenated C1-
C12Alkyl, C1-C12Alkoxy, halogenated C1-C12Alkoxy, C2-C12Alkenyl, C2-C12Alkynyl, C1-C12Alkyl sulphonyl, C1-C12
Alkyl-carbonyl, C1-C12Alkoxy carbonyl, C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkoxy carbonyl C1-C12It is alkyl, unsubstituted
Or by 1-5 R11Substituted aryl, arylmethyl, aryloxy group, fragrant amino, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl,
Aromatic yl aminocarbonyl or heteroaryl oxygroup, and by R11When substituted number is greater than 1, R11It may be the same or different；
R5、R7What be may be the same or different is selected from hydrogen, halogen, cyano, nitro, C (=O) NR9R10、C1-C12Alkyl, halogenated C1-
C12Alkyl, C1-C12Alkoxy, halogenated C1-C12Alkoxy, C1-C12Alkyl amino, halogenated C1-C12Alkyl amino, C1-C12Alkane sulphur
Base, halogenated C1-C12Alkylthio group, C2-C12Alkenyl, C2-C12Alkynyl, C1-C12Alkyl sulphonyl, C1-C12Alkyl-carbonyl, C1-C12Alkane
Epoxide carbonyl, C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkyl carbonyl epoxide, C1-
C12Alkoxy-carbonyl oxy, C1-C12Alkyl amino carbonyl oxy, C1-C12Alkyl sulphonyl oxygroup, C1-C12Alkoxy C1-C12Alkane
Oxygroup, halogenated C1-C12Halogenated alkoxy C1-C12Alkoxy, C1-C12Alkoxy carbonyl C1-C12It is alkoxy, unsubstituted or by 1-
5 R11Substituted aryl, arylmethyl, aryloxy group, fragrant amino, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, arylamino
Carbonyl or heteroaryl oxygroup, and by R1When substituted number is greater than 1, R11It may be the same or different；
R6Selected from hydrogen, halogen, cyano, nitro, carboxyl, C (=O) NR9R10、C1-C12Alkyl, halogenated C1-C12Alkyl, C1-
C12Alkoxy, halogenated C1-C12Alkoxy, C2-C12Alkenyl, C2-C12Alkynyl, C1-C12Alkyl sulphonyl, C1-C12Alkyl-carbonyl,
C1-C12Alkoxy carbonyl, C1-C12Alkoxy C1-C12Alkyl, C1-C12Alkoxy carbonyl C1-C12Alkyl, C1-C12Alkoxy C1-
C12Alkoxy, halogenated C1-C12Halogenated alkoxy C1-C12It is alkoxy, unsubstituted or by 1-5 R11Substituted aryl, Fang Jia
Base, aryloxy group, fragrant amino, aryl carbonyl, arylmethyl carbonyl, aryloxycarbonyl, aromatic yl aminocarbonyl or heteroaryl oxygroup, and by
R11When substituted number is greater than 1, R11It may be the same or different；
But R4、R5、R6、R7、R8It is not simultaneously selected from H；
R9、R10What be may be the same or different is selected from hydrogen or C1-C6Alkyl；
R11Selected from halogen, nitro, cyano, C1-C6Alkyl, halogenated C1-C6Alkyl, C1-C6Alkoxy, halogenated C1-C6Alcoxyl
Base, C1-C6Alkylthio group, C1-C6Alkyl-carbonyl, C1-C6Alkoxy carbonyl, C2-C6Alkenyl, halogenated C2-C6Alkenyl, C3-C6Alkenyloxy group,
Halogenated C3-C6Alkenyloxy group, C2-C6Alkynyl, halogenated C2-C6Alkynyl, C3-C6Alkynyloxy group, halogenated C3-C6Alkynyloxy group, halogenated C1-C6Alkane sulphur
Base, halogenated C1-C6Alkyl-carbonyl, C1-C6Alkyl amino, halogenated C1-C6Alkyl amino, C2-C8Dialkyl amido, C1-C6Alkyl oxycarbonyl
Base amino, halogenated C1-C6Alkyl-carbonyl-amino, C1-C6Alkyl amino-carbonyl or halogenated C1-C6Alkyl amino-carbonyl；
Or the salt of compound of Formula I.
Component B is selected from one or more of the fungicide of amides.
The present invention more preferably technical solution are as follows: in above-mentioned Fungicidal composition, active component A R in general formula I1=
H、R2=Cl, R3=NO2、R4=R8=Cl, R5=R7=H, R6=NO2Compound A1.
The fungicide of component B amides is selected from flumorph (flumorph) B1, dimethomorph (dimethomorph) B2, fluorine
Pyrrole bacterium amine (fluopicolide) B3, mandipropamid (mandipropamid) B4, zoxamide (zoxamide) B5, isopropyl
Bacterium amine (iprovalicarb) B6, cymoxanil (cymoxanil) B7, metalaxyl (metalaxyl-M) B8 or M 9834
(benalaxyl-M)B9。
The further preferred technical solution of the present invention are as follows: in the Fungicidal composition, active component A is selected from compound
A1；Active component B is selected from flumorph B1, dimethomorph B2, fluopicolide B3, mandipropamid B4 or zoxamide B5；It is described
A, the weight ratio between two kinds of active components of B is 1:50~50:1.
The technical solution of the present invention still more preferably are as follows: in the Fungicidal composition, active component A is selected from chemical combination
Object A1；Active component B is selected from flumorph B1, dimethomorph B2 or fluopicolide B3；Weight between two kinds of active components of described A, B
Amount is than being 10:1~1:40.
A kind of application of Fungicidal composition, the Fungicidal composition are used to prepare prevention and treatment plant pathogenic fungi disease
Drug.
Effective component of the true composition of sterilization as drug, effective content is 0.1~95wt%.
The Fungicidal composition is configured to dispersible agent, aqueous emulsion, suspending agent, water dispersible granules or wettable powder
Agent.
It was unexpectedly observed that active component A is applied in combination with active component B in the technical solution that inventor states on the implementation,
In different mixed ratios, the control efficiency of composition is significantly improved, and synergistic function is fairly obvious.
Fungicidal composition of the present invention is to the especially vegetable category of multiple diseases caused by Oomycete fungal (cucumber, muskmelon, west
Melon, tomato etc.), fruit tree (lichee), climbing plant (grape, Kiwi berry), cereal crops (rice, potato) and industrial crops
Downy mildew, peronospora tabacina, late blight, epidemic disease, balck shank, samping off in (tobacco, hops) etc. have prevention and treatment effect well
Fruit.
Fungicidal composition of the present invention is particularly suitable for preventing and treating following plants disease: cucumber downy mildew, muskmelon downy mildew, grape
Downy mildew, hop downy mildew, peronophythora litchi, tomato late blight, the late blight of potato, capsicum epidemic disease, watermelon epidemic disease, Mi
Monkey peach phytophthora root rot, cucumber samping off, eggplant samping off, capsicum samping off, rice samping off, tobacco black shank etc..
According to the occurrence degree of corps diseases, use concentration of the present composition in crop planting region is 5~
1500mg/L (active constituent content, similarly hereinafter), preferably 50~1000mg/L.
Technical solution of the present invention further includes use of the composition as the purposes of fungicide and the above-mentioned disease of prevention and treatment
Method, i.e. component A and at least one component B are prepared in advance according to appropriate proportioning provided by the invention or are prepared in use site
Or individually successively use, show significant protection effect or the obvious prevention and treatment type for expanding disease.
The present composition can be made into the pharmaceutical preparation containing 0.1~95% (weight) active component, preferably comprise 5~
The pharmaceutical preparation of 80% (weight) active component.
Fungicidal composition of the invention can be processed into the aqueous or oily suspensions for directly using or using after being watered, powder
A variety of dosage forms such as end, particulate matter.Above-mentioned various preparations can be prepared in a known manner.Such as by active component and solvent and/or
Carrier is mixed and is prepared, if desired, the auxiliary agents such as emulsifier, dispersing agent, wetting agent and surfactant can be added.These preparations
Including liquid preparation and solid pharmaceutical preparation, as dispersible agent (DC), aqueous emulsion (EW), suspending agent (SC), water dispersible granules (WG),
The common formulations of pesticide such as wettable powder (WP).
Suitable solvent or auxiliary agent are mainly water, benzene, dimethylbenzene, toluene, alkylbenzene, aliphatic hydrocarbon, alcohols, esters, ketone
Class, there are also vegetable oil and the molten fiber of methyl etc..Meanwhile the mixture of different liquids is also applicable.
Suitable surfactant be lignin sulfonic acid, naphthalene sulfonic acids, phenolsulfonic acid, dibutyl naphthalenesulfonic acid alkali metal salt,
Alkali salt and ammonium salt, alkylaryl sulfonates, alkyl sulfate, alkylsulfonate, aliphatic alcohol sulfate etc..
Suitable wetting agent is sldium lauryl sulfate, lauryl sodium sulfate, dodecyl sodium sulfate, alkyl benzene sulphonate
Sodium, Negel, sorbitan fatty acid ester polyoxyethylene ether etc..
The preparating example of certain formulations is listed below, wherein the active component is Fungicidal composition of the invention
In diphenylamine compound A1 and acid amide fungicides B, the suitable proportion between two kinds of active components of A, B is as previously described.
Suspending agent (SC)
In the ball mill of stirring, the 20% composition active component crushed, 5% part of naphthalene sulfonate formaldehyde condensation is added
Object, 0.08% xanthan gum, 0.1% White Carbon black, 4.0% agriculture breast 0201B, 4% ethylene glycol, a little defoaming agent are finally supplied with water
To 100%, active component suspending agent fine crushing is made.It is diluted with water to obtain suspension, is used for cauline leaf by spraying or soil pours.
Water dispersible granules (WG)
By 50% composition active component of grinding fine crushing, 12% castor oil ethylene oxide adduct, 2% polyethylene pyrrole
Pyrrolidone, 10% base phenol polyethenoxy base ether formaldehyde condensation products sulfate of alkane, 2.8% phenolic resin, the mixing of 23.2% gypsum are borrowed
Extruder, spray tower, fluidized bed are helped, water dispersible or water-soluble granular formulation is made.It is diluted with water to obtain dispersion or solution, use
It is sprayed in cauline leaf or soil pours.
Wettable powder (WP)
By 40% composition active component grind and be added in rotor-stator grinder 1.8% sldium lauryl sulfate,
10% White Carbon black, 8% sodium lignin sulfonate, 6% bis- (alkyl) naphthalenesulfonate formaldehyde condensation compounds, 34.2% precipitated calcium carbonate, system
At powder preparation.It is diluted with water to obtain dispersion or solution, is used for cauline leaf by spraying or soil pours.
In addition, the present invention can be added in a plurality of types of oil, wetting agent, adjuvant, herbicide, fungicide, other pesticides
In composition.These ingredients are usually mixed with the present composition with the weight ratio of 1:30~30:1.
Advantage for present invention: the present invention is to contain substituted diphenylamine amine compound shown in general formula I as activity
Component passes through a large number of experiments and research together, it is determined that with substituted diphenylamine amine compound shown in general formula I and amides
Fungicide is the suitable mixed ratio of the Fungicidal composition of active component, obtains Fungicidal composition, plays its synergistic effect,
To improve the control efficiency to corps diseases, and reduce composition dosage, it is often more important that there will be different role machine
The antimicrobial combination of reason uses, and can delay the generation of pathogen drug resistance, extend the service life of medicament.
Specific embodiment
The present composition can be described further the synergistic function of harmful fungoid by the following example, but this
Invention is only limitted to absolutely not this.Wherein the active component is the diphenylamine compound in Fungicidal composition of the invention
One of compound A1 and amides part fungicide B.
Wherein, compound A1 can according to patent WO2011116671 " a kind of substituted diphenylamine amine compound and its preparation with
Using " in record obtain.Component B is commercially available or is prepared according to known methods.
Test method and evaluation method is as follows:
Active sample to be measured is respectively compound A1, flumorph B1, dimethomorph B2, fluopicolide B3, mandipropamid
B4, zoxamide B5, metalaxyl B8；Specially compound A1 and flumorph B1, compound A1 and dimethomorph B2, compound A1
With fluopicolide B3, compound A1 and mandipropamid B4, compound A1 and zoxamide B5, compound A1 and metalaxyl B8.
Concrete mode:
Reactive compound sample or composition sample are prepared into effectively by the method that the preparating example of above-mentioned preparation is enumerated
The wettable powder that content is 40%；Appropriate formulation samples are weighed, are configured to required concentration prepare liquid after adding water.
On crops sprayer, above-mentioned prepare liquid is sprayed on disease host plant, disease inoculation is carried out after 24 hours.
It according to disease feature, cultivates being placed in climatic chamber after the disease plant inoculating for needing temperature control moisturizing culture, is invaded to disease completion
After dye, hot-house culture is moved into.After the onset of compareing sufficiently, measurement pathogen infects Crop leaf area percentage, uses Abbot public affairs
Formula calculates to arrive observation effect (W):
W=(1- α/β) × 100
In formula:
α: the fungal infection percentage of crop is handled；
β: the fungal infection percentage of untreated (blank control) crop；
Effect be " 0 " indicate processing crop infect it is horizontal with untreated control crop to infect level identical；Effect is
" 100 " indicate that processing crop is not infected.
The expection effect (calculate effect) of composition using Colby formula (see R.S.Colby, weeds (Weeds), 1967,
15,20-22) it determines, and compared with observing effect.
E=X+Y-XY/100
In formula:
E: using active component A and B that concentration is a and b composition when expection effect (calculating in following table is imitated
Power), it is indicated with the % of untreated control；
X: using concentration be a when active component A effect, indicated with the % of untreated control；
Y: using concentration be b when active component B effect, indicated with the % of untreated control.
When observing effect value greater than effect value is calculated, indicate that composition has synergistic effect；When observation effect value is equal to
When calculating effect value, expression composition is adduction；When observing effect value less than effect value is calculated, indicate that composition is short of money
Anti- effect.
Implementation of an application example 1 prevents and treats cucumber downy mildew test
It is two leaf phase of potting cucumber seedling prepare liquid (concentration the is as described below) spraying treatment of " the close thorn in Xintai City " by kind,
After 24 hours, test plants are inoculated with the sporangia suspension of cucumber downy mildew.By test plants be placed in temperature be 22 ± 2 DEG C and
It is cultivated in the climatic chamber that relative humidity is 90 ± 5%, after 24 hours, moves into greenhouse normal management.After 5 days, disease on blade is measured
The degree that bacterium is infected.The activity data of each independent active component and present composition prevention and treatment cucumber downy mildew the results are shown in Table 1 He
Table 2.
The results show that the observation effect value of composition, which is all larger than, calculates effect value.Illustrate composition in test ratio range
Inside show as synergistic effect.
The activity of the independent active component of table 1
The activity of 2 present composition of table
Implementation of an application example 2 prevents and treats downy mildew of garpe test
Kind is spraying for the grape potting five leaf phases cuttage seeding prepare liquid (concentration is as described below) of " the seedless Cold boiled chicken heart "
Processing after 24 hours, is inoculated with test plants with the sporangia suspension of downy mildew of garpe.By test plants be placed in temperature be 23 ±
It is cultivated in the climatic chamber that 2 DEG C are 90 ± 5% with relative humidity, after 24 hours, moves into greenhouse normal management.After 7 days, blade is measured
The degree that upper germ is infected.The activity data of each independent active component and present composition prevention and treatment downy mildew of garpe the results are shown in Table
3 and table 4.
The results show that the observation effect value of composition, which is all larger than, calculates effect value.Illustrate composition in test ratio range
Inside show as synergistic effect.
The activity of the independent active component of table 3
The activity of 4 present composition of table
Implementation of an application example 3 prevents and treats tomato late blight test
This test uses spore germination method, that is, presses design concentration, take high concentration prepare liquid to mix with sporangia suspension, obtain
To active sample to be measured -- sporangium mixed liquor, and be added in 96 well culture plates, it is subsequently placed in incubator and cultivates (22 DEG C ± 1
DEG C), microscopy after 4 hours.The sporangium Germination suppression rate of composition and each individual active component is obtained according to the following formula.Composition
Interaction analysis uses mentioned-above Colby formula.Each individual active component and present composition prevention and treatment tomato evening
The activity data of epidemic disease the results are shown in Table 5 and table 6.
The results show that the observation effect value of composition, which is all larger than, calculates effect value.Illustrate composition in test ratio range
Inside show as synergistic effect.
The activity of the independent active component of table 5
The activity of 6 present composition of table
Implementation of an application example 4 prevents and treats capsicum epidemic disease test
This test uses spore germination method, that is, presses design concentration, take high concentration prepare liquid to mix with sporangia suspension, obtain
To active sample to be measured -- sporangium mixed liquor, and be added in 96 well culture plates, it is subsequently placed in incubator and cultivates (22 DEG C ± 1
DEG C), microscopy after 4 hours.The sporangium Germination suppression rate of composition and each individual active component is obtained according to the following formula.Composition
Interaction analysis uses mentioned-above Colby formula.Each individual active component and the present composition prevent and treat capsicum epidemic disease
The activity data of disease the results are shown in Table 7 and table 8.
The results show that the observation effect value of composition, which is all larger than, calculates effect value.Illustrate composition in test ratio range
Inside show as synergistic effect.
The activity of the independent active component of table 7
The activity of 8 present composition of table
Claims (5)
1. a kind of Fungicidal composition, it is characterised in that: two kinds of active components of composition A, B；
Component A is selected from following general formula I compound represented:
In formula: R1=H, R2=Cl, R3=NO2、R4=R8=Cl, R5=R7=H, R6=NO2Compound A1；
Active component B is selected from flumorph B1, and the weight ratio between two kinds of active components of A, B is 1:16~10:1；
Active component B is selected from dimethomorph B2, and the weight ratio between two kinds of active components of A, B is 1:16~10:1；
Active component B is selected from fluopicolide B3, and the weight ratio between two kinds of active components of A, B is 1:16~10:1；
Active component B is selected from mandipropamid B4, and the weight ratio between two kinds of active components of A, B is 1:16~10:1；
Active component B is selected from zoxamide B5, and the weight ratio between two kinds of active components of A, B is 1:16~10:1；
Active component B is selected from metalaxyl B8, and the weight ratio between two kinds of active components of A, B is 1:10~1:100.
2. a kind of application of Fungicidal composition described in claim 1, it is characterised in that: the Fungicidal composition is for making
The drug of standby prevention and treatment plant pathogenic fungi disease.
3. the application of Fungicidal composition according to claim 2, it is characterised in that: the Fungicidal composition is made
For the effective component of drug, effective content is 0.1~95wt%.
4. the application of Fungicidal composition according to claim 2, it is characterised in that: the Fungicidal composition is configured to
Dispersible agent, aqueous emulsion, suspending agent, water dispersible granules or wettable powder.
5. the application of Fungicidal composition according to claim 2, it is characterised in that: the Fungicidal composition is for making
The standby drug for preventing and treating plant downy mildew, peronospora tabacina, epidemic disease or balck shank.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011076726A2 (en) * | 2009-12-23 | 2011-06-30 | Bayer Cropscience Ag | Pesticidal compound mixtures |
| CN102199095A (en) * | 2010-03-22 | 2011-09-28 | 中国中化股份有限公司 | Substituted diphenylamine compounds and preparation and application thereof |
| CN103301096A (en) * | 2012-03-14 | 2013-09-18 | 中国中化股份有限公司 | Application of substituted diphenylamine compound to preparation of antitumor drugs |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011076726A2 (en) * | 2009-12-23 | 2011-06-30 | Bayer Cropscience Ag | Pesticidal compound mixtures |
| CN102199095A (en) * | 2010-03-22 | 2011-09-28 | 中国中化股份有限公司 | Substituted diphenylamine compounds and preparation and application thereof |
| CN103301096A (en) * | 2012-03-14 | 2013-09-18 | 中国中化股份有限公司 | Application of substituted diphenylamine compound to preparation of antitumor drugs |
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