CN104488906B - A kind of containing methylsulfonyl bacterium azoles and the complex composition of benziothiazolinone and antibacterial - Google Patents
A kind of containing methylsulfonyl bacterium azoles and the complex composition of benziothiazolinone and antibacterial Download PDFInfo
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Abstract
The invention discloses a kind of containing methylsulfonyl bacterium azoles and the complex composition of benziothiazolinone, it is with methylsulfonyl bacterium azoles and benziothiazolinone as main active, and wherein the chemical name of methylsulfonyl bacterium azoles is 2 (to fluorophenyl) 5 mesyl 1,3,4 diazole；The weight ratio of methylsulfonyl bacterium azoles and benziothiazolinone is (100～1): (1～40), more preferably (40～1): (1～10).The weight summation of active components A and B accounts for the 0.1 90% of said composition gross weight.The complex composition of the present invention shows obvious synergistic function, reduces the Drug resistance of disease simultaneously.Can be used for preventing and treating various crop bacterial disease, such as bacterial diseases such as bacterial leaf streak of rice, bacterial blight of rice, cucumber bacterial angular leaf spot, bacterial wilt of tomato, soft rot of Chinese cabbage, citrus bacterial canker diseases.
Description
Technical field
The present invention relates to technical field of pesticide, particularly relate to containing methylsulfonyl bacterium azoles and the complex composition of benziothiazolinone and sterilization
Agent.
Background technology
Along with weather, the change of pattern of farming, the generation of bacterial diseases of crops, the loss caused increases the weight of year by year, but
It is that the correlational study of bacterial disease does not obtain enough attention, the Prevention Technique of bacterial disease is lagged behind fungus relatively
Disease, causes bacterial disease to be increasingly becoming the Major Diseases having a strong impact on agricultural production in some areas.Secondly, at present to carefully
The preferable pharmacy variety of fungal disease drug effect is few.
To this end, Guizhou University's independent research have new type bactericide " the one class preventing and control crop antibacterial of independent intellectual property rights
The diazole sulfone compound (Patent No. ZL201110314246.2) of disease ", its structural formula is:
The step of preparation process of this compound and condition:
(1) preparation of different replacing acid methyl ester intermediate: with different organic acid and absolute methanol as raw material, at concentrated sulphuric acid
Lower back flow reaction 6-10 hour of catalysis, reduce pressure separating methanol, and after saturated sodium bicarbonate aqueous solution adjusts ph=7, separatory obtains different first
Acid methyl ester；
(2) preparation of different substituted formylhydrazine intermediate: be dissolved in methanol with different methyl formates, the most slowly add
40%-80% hydrazine hydrate, till back flow reaction is complete, separates out different substituted formylhydrazine after cooling；
(3) 2-sulfydryl-5-replaces the preparation of-1,3,4-diazole intermediate: with the formylhydrazine of above-mentioned preparation and KOH, two
Nitric sulfid is raw material, and ethanol is solvent, and back flow reaction is complete, de-ethanol, adjusts PH=5 to obtain 2-sulfydryl-5-and replaces-1,3,4-
Diazole；
(4) 2-thioether-5-replaces the preparation of-1,3,4-diazole intermediate: replace-1,3,4-with above-mentioned 2-sulfydryl-5-
Diazole is raw material, after hydro-oxidation sodium water dissolution, is reacted by dimethyl sulfate (second) ester or the halogenated hydrocarbons etc. of mole with 1-2
To corresponding sulfide compound；
(5) 2-methyl (ethyl) sulfonyl-5-replaces the preparation of-1,3,4-diazole.
With corresponding thioether as raw material, it is dissolved in glacial acetic acid, 2%-7% potassium permanganate solution or 30% hydrogen peroxide
Oxidation obtains corresponding sulfone compound.
Summary of the invention
For diazole sulfone compound, applicant researches and develops further, as Rn fluorine in halogen atom, R2Select C1-C5
The methyl of alkyl i.e. obtains the structural formula of diazole sulfone compound:
Its chemical name is 2-(to fluorophenyl)-5-mesyl-1,3,4-diazole, is called for short methylsulfonyl bacterium azoles.
The concrete syntheti c route of compound methylsulfonyl bacterium azoles is as follows:
(1) synthesis to fluorobenzoyl hydrazine
(2) the 2-sulfydryl-5-synthesis to fluorophenyl-1,3,4-diazole
(3) the 2-Dimethyl sulfide-5-synthesis to fluorophenyl-1,3,4-diazole
(4) 2-(to fluorophenyl)-5-mesyl-1,3,4-diazole target compound is prepared
Applicant further study show that, methylsulfonyl bacterium azoles is a kind of novel bacterial disease pesticide control, can ooze
Enter plant epidermis, after Uptake and translocation, act on target leaf, synthesized by the energy of suppression antibacterial, finally suppress antibacterial
Growth and breeding.Show that bacterial blight of rice, cucumber bacterial angular leaf spot, Citrus are burst by methylsulfonyl bacterium azoles through great many of experiments
The series disease such as infections disease, bacterial wilt of peanut, soft rot of cabbage has good control effect.This medicament production technology is simple, right
Environmental friendliness, discharge without three industrial wastes, production cost is relatively low, meets the environmental protection theory that modern agricultural production is advocated.
And sterilize and general extensively various bacterial disease had good control effect, there is high-efficiency low-toxicity, wide spectrum, the feature of safety,
It is a kind of to there is exploitation for the novel green pesticide of large tonnage product potential quality.
Benziothiazolinone is a kind of novel, wide-spectrum bactericide, is mainly used in preventing and treating and treatment cucumber downy mildew, pear scab, Herba Marsileae Quadrifoliae
The really various bacteria of shot hole, citrus anthracnose, grapevine anthracnose etc., fungal disease.Its bactericidal action mechanism, mainly includes
Destroy pathogenic bacteria nuclear structures so that it is lose core position and exhaustion is dead and the metabolism of interference pathogenic bacteria cell so that it is raw
Reason disorder, ultimately results in dead two aspects.
Through our substantial amounts of experiment, show that methylsulfonyl bacterium azoles can effectively prevent and delay soft rot, Peptic Ulcers, green grass or young crops
The generation of the diseases such as rot and extension.Methylsulfonyl bacterium azoles is mixed with benziothiazolinone, on the one hand methylsulfonyl bacterium azoles suppression antibacterial, and induction is planted
Strain disease resistance, on the other hand, benziothiazolinone is the most also a kind of broad-spectrum germicide, not only can significantly improve methylsulfonyl bacterium azoles
Preventive effect, moreover it is possible to expand the preventing and treating spectrum of complex composition, guarantee yield to greatest extent.
In view of this, for drawbacks described above, it is an object of the invention to: a kind of answering containing methylsulfonyl bacterium azoles and benziothiazolinone is provided
Combo compound and antibacterial thereof, show obvious synergistic function at preventing and treating bacterial disease.
In order to reach the mesh of invention, the technical solution used in the present invention is:
A kind of containing methylsulfonyl bacterium azoles and the complex composition of benziothiazolinone, described complex composition is with methylsulfonyl bacterium azoles and thiophene
Mould ketone is active component, and wherein the chemical name of methylsulfonyl bacterium azoles is 2-(to fluorophenyl)-5-mesyl-1,3,4-bis-
Azoles；The weight ratio of methylsulfonyl bacterium azoles and benziothiazolinone is (100～1): (1～40).
Above-described containing methylsulfonyl bacterium azoles and the complex composition of benziothiazolinone, described methylsulfonyl bacterium azoles and the weight of benziothiazolinone
Amount ratio is preferably (40～1): (1～10).
Above-described containing methylsulfonyl bacterium azoles and the complex composition of benziothiazolinone, described methylsulfonyl bacterium azoles and the weight of benziothiazolinone
Amount ratio is preferably (20～1): (1～5).
The present invention also provides for a kind of containing methylsulfonyl bacterium azoles and the preparation of benziothiazolinone, contains 0.1～more than 90% by weight
Arbitrary described complex composition, remaining is acceptable auxiliary agent and carrier on pesticide, is then prepared as preventing and treating crop pest
Antibacterial.
Above-described containing methylsulfonyl bacterium azoles and the preparation of benziothiazolinone, described antibacterial contains 1～80% by weight
Complex composition described in any of the above.
Above-described containing methylsulfonyl bacterium azoles and the preparation of benziothiazolinone, described antibacterial is configured to water dispersible granules, wettable
Property powder, microemulsion, suspending agent, aqueous emulsion, cream, suspension seed-coating agent.
Auxiliary agent of the present invention can include surfactant, defoamer, thickening agent, disintegrating agent and antifreezing agent as required
In one or more, it is also possible to include other auxiliary agents that the industry is conventional as required.
Surfactant used preferably is selected from polyoxyethylene sorbitan fatty acid ester series, fatty alcohol-polyoxyethylene ether system
Row, condensation compound of alkyl phenol and epoxy ethane OP series, NPE series, styrylphenol formaldehyde resin polyoxy
Ethylene-oxypropylene block type polyether series, triphen ethyl phenol polyoxyethylene ether series, double phenethyl phenol polyethenoxy ether system
Row, in calcium dodecyl benzene sulfonate (i.e. 500#) one or more.
Wetting dispersing agent preferably is selected from sodium lauryl sulphate, diisobutyl LOMAR PWA EINECS 246-676-2 (abbreviation pulls open powder), the di-2-ethylhexylphosphine oxide bitter edible plant
Sodium sulfonate (be called for short NNO), acrylic acid and propionic acid amide. copolymer, dispersing agent MF (being called for short MF), sodium polyacrylate,
Desaccharide the sodium lignin sulfonate of classification, desaccharide, the sodium lignin sulfonate of condensation and modification, lignosulfonates, polycarboxylic acids derive
In thing sodium lignin sulfonate one or more.
Any one or two kinds that thickening agent preferably is selected from xanthan gum, aluminium-magnesium silicate.
Disintegrating agent includes potassium phosphate, potassium carbonate, potassium sulfate, sodium chloride, sodium sulfate, sodium phosphate, ammonium sulfate.
Antifreezing agent includes isopropanol, propylene glycol, glycerol, ethylene glycol, carbamide.
Film former includes animal glue, pectin, Polyethylene Glycol.
Binding agent includes ethyl cellulose, starch, polyvinyl alcohol.
Carrier of the present invention can be solid or liquid, and the carrier being generally used for compositions formulated antibacterial all can make
With.
Described solid carrier preferably is selected from white carbon, Kaolin, water, potter's clay, bentonite, kieselguhr, earth powder, lightweight carbonic acid
One or more in calcium
During described bactericidal composition preparation liquid dosage form, the liquid-carrier used includes water and organic solvent, You Jirong
Agent is toluene, dimethylbenzene, methyl oleate, solvent naphtha, Oleum Terebinthinae, vegetable oil, dichloromethane, chloroform, methanol, ethanol, different
Propanol, butanol, isoamyl alcohol, Ketohexamethylene, isophorone, 1-Phenylethanone., ethyl acetate, butyl acetate, N-Methyl pyrrolidone, diformazan
Base sulfoxide, methyl cellosolve, ethyl cellosolve, solvent naphtha 200#, solvent naphtha 150#, methyl naphthalene can be used alone, it is possible to two kinds
Or use mixed above.
As preferably, organic solvent of the present invention is ethanol, solvent naphtha 200#, solvent naphtha 150#, methyl naphthalene, N methyl
In ketopyrrolidine one or more.
Complex composition of the present invention can be configured to wettable powder, water-dispersible according to method generally in the art
Granule, microemulsion, aqueous emulsion, suspending agent, seed coat agent, cream.
Complex composition of the present invention is applicable to prevent and treat crop bacterial disease and some fungi sexually transmitted disease (STD) evil, such as Chinese cabbage
Soft rot, watermelon blight, cucumber bacterial angular leaf spot and downy mildew, tobacco bacterial wilt, citrus bacterial canker disease and shot hole, Oryza sativa L.
Slice is sick and bacterial leaf-blight sick, Fructus Lycopersici esculenti shot hole and Peptic Ulcers, downy mildew of garpe, the antibacterial such as bacterial wilt of melon and solanaceous vegetable
Fungal disease.
The compositions of the present invention can be used by commonsense method, processes as added water spray stem and leaf, it is also possible to root is executed, and also may be used
Use with seed dressing or seed pelleting.It is mainly used in the crops such as Oryza sativa L., Nicotiana tabacum L., Fructus Cucumidis sativi, Fructus Lycopersici esculenti, Citrus, prevents and control antibacterial
Sexually transmitted disease (STD) evil, it is ensured that yield.
Complex composition of the present invention has the advantages that compared to existing technology
1, methylsulfonyl bacterium azoles and benziothiazolinone compound, and prevent and treat its co-toxicity coefficient of crop pest and be more than in the range of certain proportion
120, show obvious synergistic function.
2. reduce the usage amount of pesticide,
Guarantee yield the most to greatest extent: methylsulfonyl bacterium azoles is all broad-spectrum germicide with benziothiazolinone simultaneously, effective object
Predominantly plant pathogenetic bacteria, has bigger difference in the mechanism of action, can play complementary potentiation, increase each other effect
The effect effectiveness of target, such that it is able to guarantee crop yield to the full extent.
Detailed description of the invention
Present invention the following example illustrates, but does not limits the scope of the invention.Methylsulfonyl used in the present invention
The former medicine of bacterium azoles is provided by Guizhou University, and other former medicines used and preparation are commercial.Wherein active component (A) is methylsulfonyl bacterium
Azoles (is called for short methylsulfonyl) in below table；Active component (B) is benziothiazolinone.
In preparation embodiment, wetting dispersing agent used includes diisobutyl sodium naphthalene sulfonate (abbreviation pulls open powder), the di-2-ethylhexylphosphine oxide bitter edible plant
Sodium sulfonate (be called for short NNO), acrylic acid and propionic acid amide. copolymer (being called for short DA), dispersing agent MF (being called for short MF), poly-
The sodium lignin sulfonate (being called for short M-9) of sodium acrylate (being called for short DC), desaccharide classification, the sodium lignin sulfonate of desaccharide condensation and modification
(being called for short M-10), lignosulfonates (being called for short M-11), poly carboxylic acid derivative's (being called for short CF), sodium lignin sulfonate (are called for short M-
14)。
Surfactant selected from polyoxyethylene sorbitan fatty acid ester series include T-20, T-40, T-60, T-80,
T-85, fatty alcohol-polyoxyethylene ether series includes that AEO-9, AEO-15, AEO-20, OS-15, JFC, alkyl phenol contract with oxirane
Compound series includes that OP-10, OP-15, OP-18, OP-20, NPE series include NP-10, NP-15, NP-
18, NP-20, styrylphenol formaldehyde resin PULLRONIC F68 block type polyether series include 33#, 34#, 36#,
37#, triphen ethyl phenol polyoxyethylene ether series includes that 601#, 602#, 603#, double phenethyl phenol polyethenoxy ether series include
604#, 605#, 606#, anion surfactant calcium dodecyl benzene sulfonate (500#).
For the sake of unification, preparation embodiment set forth below, dispersant and emulsifying agent all use abbreviation or commercial disignation.
Embodiment prepared by preparation:
One, the preparation of water dispersible granules
By methylsulfonyl bacterium azoles, benziothiazolinone, wetting dispersing agent, binding agent, white carbon, disintegrating agent, carrier mix homogeneously, through gas
After stream pulverizer is pulverized, stirring 30min, mediate with water, rear addition carries out pelletize, is dried, obtains in fluidized-bed granulation dryer
The water dispersible granules of antibacterial of the present invention.
Two, the preparation of microemulsion
Methylsulfonyl bacterium azoles and benziothiazolinone are added in organic solvent, after stirring, obtains transparent mixed liquor；To above-mentioned
Adding surfactant in mixed liquor, stirring to emulsifying agent is completely dissolved；Under the mixing speed of 50r/min, add water to
In the above-mentioned mixed liquor being dissolved with surfactant, at ambient temperature, stir 30min, obtain the microemulsion of homogeneous transparent；Upwards
State addition antifreezing agent in microemulsion, stir, obtain the microemulsion of antibacterial of the present invention.Formula forms:
Three, the preparation of suspending agent
By surfactant, antifreezing agent, thickening agent, moisture content mixing, through high speed shear mix homogeneously, it is sequentially added into methylsulfonyl
Bacterium azoles, benziothiazolinone, abrading-ball 2～3 hours in ball crusher, prepare antibacterial of the present invention suspending agent.
Four, the preparation of aqueous emulsion
By methylsulfonyl bacterium azoles, benziothiazolinone, surfactant, organic solvent mixing, it is dissolved into uniform oil phase；By part
Water, antifreezing agent mix uniformly aqueous phase；Oil phase adds while high-speed stirred aqueous phase in a kettle., and unlatching is cut
The machine of cutting carries out high speed shear, and adds remaining water and supply, and shears about half an hour, forms aqueous emulsion.I.e. prepare of the present invention
The aqueous emulsion of antibacterial.
Five, the preparation of wettable powder
By methylsulfonyl bacterium azoles, benziothiazolinone, wetting dispersing agent, white carbon, carrier mix homogeneously, pulverize through jet mill
After, stir 30min, obtain the wettable powder of antibacterial of the present invention.
Comparative examples is 20% methylsulfonyl bacterium azoles wettable powder.
Six, the preparation of cream
Methylsulfonyl bacterium azoles and benziothiazolinone are added in organic solvent, add obtain after surfactant stirs transparent
Mixed liquor, i.e. prepare the cream of antibacterial of the present invention
Seven, suspension seed-coating agent
By methylsulfonyl bacterium azoles and benziothiazolinone through comminution by gas stream, add surfactant, film former, thickening agent, antifreezing agent with
Water is thoroughly mixed rear, puts into sand mill in proportion and grinds 2 times, until it is 2-3 μm that the fineness of the particles of suspension reaches D50, and D90
＜ 8 μm, obtains the suspension seed-coating agent of antibacterial of the present invention.
The present composition is in addition to can being made into above dosage form, it is also possible to make micro-capsule suspension, injection drying agent, super-low capacity
The multiple dosage forms such as amount.
Toxicity Determination
The test of following indoor biometrics uses the abundant method of Sun Yun to calculate co-toxicity coefficient (CTC) and evaluates mixed effect.
Toxicity index TI (B)=(EC of standard agent A50The EC of ÷ B agent50)×100
Actual toxicity index ATI (AB)=(EC of A50The EC of ÷ AB50)×100
Theoretical toxicity index TTI (AB)=TI (A) × A percent+TI (B) × B percentage in mixture in mixture
Number
Actual measurement toxicity index (ATI)=(standard agent EC50÷ reagent agent EC50)×100
Percentage composition+B medicament the toxicity index of A in theoretical toxicity index (TTI)=A medicament toxicity index × mixture × mixed
The percentage composition of B in agent
Co-toxicity coefficient (CTC)=[mixture actual measurement toxicity index (ATI) ÷ mixture theory toxicity index (TTI)] × 100 are commented
Price card standard is: co-toxicity coefficient >=120 show as potentiation；Co-toxicity coefficient≤80 show as antagonism；80 < co-toxicity coefficient <
120 show as summation action.
The Toxicity Determination of preventing and treating cucumber downy mildew:
Test method: prepare some source of disease blades, with 4 DEG C of distillation washing lower blade back side Pseudoperonospora cubensis Sporangiums, is made into
1 × 107 Sporangium/ml of suspension.Medicament mother solution is diluted to corresponding concentration with 0.05% Tween 80 aqueous solution, uniformly sprays
Impose on the plant leaf two sides cultivated in advance to 4～6 leaf periods to whole moistenings, often process 4 times and repeat, if using fresh water spraying
Process be blank, after dispenser 24h, Fresh spores capsule suspension spray is inoculated in vacuum side of blade, at continuous light every day
According to/dark each 12h alternately, temperature is 22 DEG C, and relative humidity is to cultivate under conditions of more than 90%.When blank sickness rate reaches
To more than 50% time stage investigation incidence, calculate disease index and preventive effect, according to each drug concentration logarithm value and correspondence
Preventive effect probability value calculates the EC of lattice medicament50And co-toxicity coefficient.
Table 1 methylsulfonyl bacterium azoles and benziothiazolinone compound the Toxicity Determination result of preventing and treating cucumber downy mildew
| Composition | EC50(μg/ml) | ATI | TTI | CTC |
| Methylsulfonyl bacterium azoles (A) | 27.38 | 100.00 | / | / |
| Benziothiazolinone (B) | 14.92 | 183.51 | / | / |
| A:B=100:1 | 22.31 | 122.73 | 100.83 | 121.72 |
| A:B=60:1 | 19.27 | 142.09 | 101.37 | 140.17 |
| A:B=40:1 | 17.84 | 153.48 | 102.04 | 150.41 |
| A:B=20:1 | 16.67 | 164.25 | 103.98 | 157.97 |
| A:B=10:1 | 15.94 | 171.77 | 107.59 | 159.65 |
| A:B=5:1 | 13.26 | 206.49 | 113.92 | 181.26 |
| A:B=2:1 | 11.19 | 244.68 | 127.84 | 191.40 |
| A:B=1:1 | 9.43 | 290.35 | 141.76 | 204.82 |
| A:B=1:2 | 8.72 | 313.99 | 155.67 | 201.70 |
| A:B=1:5 | 9.37 | 292.21 | 169.59 | 172.30 |
| A:B=1:10 | 10.34 | 264.80 | 175.92 | 150.52 |
| A:B=1:20 | 11.57 | 236.65 | 179.54 | 131.81 |
| A:B=1:30 | 12.10 | 226.28 | 180.82 | 125.14 |
| A:B=1:40 | 12.49 | 219.22 | 181.48 | 120.80 |
| A:B=1:50 | 13.15 | 208.21 | 181.87 | 114.48 |
From table 1, methylsulfonyl bacterium azoles is compounded in above ratio with benziothiazolinone, and in 15 proportionings, in addition to 1:50, remaining is joined
It is all higher than 120 than CTC, therefore in (100～1): between (1～40), there is potentiation in varying degrees；When proportioning (40～
1): time between (1～10), potentiation is especially pronounced, and co-toxicity coefficient is more than 150.
The Toxicity Determination of preventing and treating citrus bacterial canker disease:
Test method: (the old spring edits, and publishing house of Beijing Agricultural University goes out with reference to " pesticide bioassay technology " in test
Version) and " farm-chemical indoor determination test rule NY/T1156.2-2006 ".This test uses inhibition zone method.Aseptic behaviour
In station, NA culture medium being poured on NA flat board, after drying, the citrus processing bacteria suspension spreading rod taking 0.1ml is uniform
Be applied on NA flat board.After drying, punch in flat board central authorities with the card punch of diameter 7mm, then take 100 μ l medicinal liquids in aperture
In.Each concentration 5 repetition.The process of sterilized water is added as blank in aperture.The perseverance of 28 ± 0.5 DEG C it is placed on after process
Incubator aseptic culture, takes out after 2d.Decussation method is used to measure the antibacterial circle diameter (in units of millimeter) of each process respectively,
And calculate the meansigma methods of antibacterial circle diameter, suppression ratio.Carry out statistical analysis with DPS data processing software, calculate each medicament
EC50, then press the abundant method of Sun Yun and calculate co-toxicity coefficient (CTC).
Table 2 methylsulfonyl bacterium azoles and benziothiazolinone compound the Toxicity Determination result of preventing and treating citrus bacterial canker disease
| Composition | EC50(μg/ml) | ATI | TTI | CTC |
| Methylsulfonyl bacterium azoles (A) | 7.48 | 100.00 | / | / |
| Benziothiazolinone (B) | 46.37 | 16.13 | / | / |
| A:B=100:1 | 6.27 | 119.30 | 99.17 | 120.30 |
| A:B=75:1 | 5.89 | 126.99 | 98.90 | 128.41 |
| A:B=40:1 | 4.97 | 150.50 | 97.95 | 153.65 |
| A:B=30:1 | 4.68 | 159.83 | 97.29 | 164.27 |
| A:B=20:1 | 4.47 | 167.34 | 96.01 | 174.30 |
| A:B=10:1 | 4.61 | 162.26 | 92.38 | 175.65 |
| A:B=5:1 | 4.87 | 153.59 | 86.02 | 178.55 |
| A:B=3:1 | 5.20 | 143.85 | 79.03 | 182.01 |
| A:B=1:1 | 6.54 | 114.37 | 58.07 | 196.97 |
| A:B=1:3 | 11.19 | 66.85 | 37.10 | 180.18 |
| A:B=1:5 | 15.73 | 47.55 | 30.11 | 157.93 |
| A:B=1:10 | 20.67 | 36.19 | 23.76 | 152.33 |
| A:B=1:20 | 27.03 | 27.67 | 20.12 | 137.51 |
| A:B=1:40 | 33.47 | 22.35 | 18.18 | 122.95 |
| A:B=1:50 | 36.78 | 20.34 | 17.78 | 114.41 |
From table 2, methylsulfonyl bacterium azoles is compounded in above ratio with benziothiazolinone, and in 15 proportionings, in addition to 1:50, remaining is joined
It is all higher than 120 than CTC, therefore in (100～1): between (1～40), there is potentiation in varying degrees；When proportioning (40～
1): time between (1～10), potentiation is especially pronounced, co-toxicity coefficient is more than 150.
The Toxicity Determination of preventing and treating cucumber bacterial angular leaf spot:
Test method: be that 108cfu mL-1 pathogen adds in each diameter 9cm sterilizing culture dish by bacteria suspension concentration
Enter 0.5mL, then pour 15mL into and be cooled in 45 DEG C of gravy peptone culture medium, fully mix, solidification.At culture dish bottom marker positive three
The 3 Ge Ju center equidistant Angle Position of 2.5cm of dihedral, prevent Oxford cup (high 10mm, internal diameter 6mm), and dropping equivalent difference is dense
The medicament diluent of degree, cultivates 7d under 28 DEG C of constant temperature aseptic conditions, measures antibacterial circle diameter, and calculates the flat of antibacterial circle diameter
Average, suppression ratio.Carry out statistical analysis with DPS data processing software, calculate the EC of each medicament50, then press the abundant method of Sun Yun and calculate
Co-toxicity coefficient (CTC).
Table 3 methylsulfonyl bacterium azoles and benziothiazolinone compound the Toxicity Determination result of preventing and treating cucumber bacterial angular leaf spot
| Composition | EC50(μg/ml) | ATI | TTI | CTC |
| Methylsulfonyl bacterium azoles (A) | 9.67 | 100.00 | / | / |
| Benziothiazolinone (B) | 57.46 | 16.83 | / | / |
| A:B=100:1 | 8.02 | 120.57 | 99.18 | 121.57 |
| A:B=60:1 | 7.28 | 132.83 | 98.64 | 134.67 |
| A:B=40:1 | 6.46 | 149.69 | 97.97 | 152.79 |
| A:B=30:1 | 5.58 | 173.30 | 97.32 | 178.08 |
| A:B=20:1 | 4.74 | 204.01 | 96.04 | 212.42 |
| A:B=10:1 | 4.39 | 220.27 | 92.44 | 238.29 |
| A:B=5:1 | 5.37 | 180.07 | 86.14 | 209.05 |
| A:B=1:1 | 8.84 | 109.39 | 58.41 | 187.26 |
| A:B=1:2 | 12.19 | 79.33 | 44.55 | 178.05 |
| A:B=1:5 | 18.71 | 51.68 | 30.69 | 168.40 |
| A:B=1:10 | 25.67 | 37.67 | 24.39 | 154.45 |
| A:B=1:20 | 31.95 | 30.27 | 20.79 | 145.58 |
| A:B=1:30 | 38.77 | 24.94 | 19.51 | 127.83 |
| A:B=1:40 | 42.49 | 22.76 | 18.86 | 120.68 |
| A:B=1:50 | 47.82 | 20.22 | 18.46 | 109.54 |
From table 3, methylsulfonyl bacterium azoles is compounded in above ratio with benziothiazolinone, and in 15 proportionings, in addition to 1:50, remaining is joined
It is all higher than 120 than CTC, therefore in (100～1): between (1～40), there is potentiation in varying degrees；When proportioning (40～
1): time between (1～10), potentiation is especially pronounced, co-toxicity coefficient is more than 150.
The field control effectiveness test of preventing and treating cucumber downy mildew:
Test method and drug effect computational methods: with reference to GB/T17980.26-2000 pesticide field efficacy medicine test criterion (one):
Bactericidal agent for preventing and treating cucumber downy mildew；Controlling object: cucumber downy mildew；
Test site: Nanning doube bridge.
Experimental plot: 24 communities are chosen in field, is divided into 6 groups, often 4 repetitions of group, random number；
Test method: processing different districts with test medicine respectively and use directed spraying method, dispenser for the first time is away from second time
Spraying time is spaced apart 7 days.
Investigation method: Yao Qianmei community takes a bit, every 5 strains, every strain 2 leaf (from top to bottom), 5, Yao Houmei community takes
Sample, 10 clumps every, every strain 2 leaf (from top to bottom).Within after dispenser 7 days, 14 days, investigate respectively once.
Stage division:
0 grade: blade is without scab；
1 grade: lesion area accounts for less than the 5% of whole leaf area；
3 grades: lesion area accounts for the 6%～10% of whole leaf area；
5 grades: lesion area accounts for the 11%～25% of whole leaf area；
7 grades: lesion area accounts for the 26%～50% of whole leaf area；
9 grades: lesion area accounts for more than the 51% of whole leaf area.
Comparison medicament: 3% benziothiazolinone wettable powder, registration card PD20100161, the big HuaTe Science industry in west, Shaanxi has
Limit company, commercial.
The field control effectiveness test result of cucumber downy mildew prevented and treated by table 4
Result of the test: as shown in Table 4, from the preventive effect of preventing and treating cucumber downy mildew, methylsulfonyl bacterium azoles+benziothiazolinone and single dose
Methylsulfonyl bacterium azoles or benziothiazolinone are compared, and in the case of effective ingredient consumption is identical even less, methylsulfonyl bacterium azoles+benziothiazolinone is prevented
Control 14d prevention effect (effective ingredient dosage 15g/667m of cucumber downy mildew2) it is respectively higher than single dose 20% first sulphur sulfonyl bacterium
Azoles WP (effective ingredient dosage 10g/667m2) and benziothiazolinone WP (effective ingredient dosage 20g/667m2) prevention effect be
More than 14.95% and more than 18.38, and remain to reach the preventive effect of more than 74% at 14d, the lasting period is long.
The field control effectiveness test of preventing and treating citrus bacterial canker disease:
Test method: with reference to GB/T17980.103-2004 pesticide field efficacy medicine test criterion (two) the 103rd part: sterilization
Agent preventing and treating citrus bacterial canker disease；
Controlling object: citrus bacterial canker disease
Test site: Nanning Shi Bu
Experimental plot: choose 24 communities, random alignment, each community 3 strain becomes fruit tree in age, each process 4 repetition；
Test method: using directed spraying method, dispenser for the first time is spaced apart 7 days away from second time spraying time.
Investigation method: two strains are investigated in every community, every strain takes 5 points, chooses 10 fruits and two blade tips, before dispenser at every
Investigation once, is investigated once for after dispenser 20 days for the first time.
Stage division:
0 grade: anosis；
1 grade: every leaf (really) has scab 1-5；
3 grades: every leaf (really) has scab 6-10；
5 grades: every leaf (really) has scab 11-15；
7 grades: every leaf (really) has scab 16-20；
9 grades: every leaf (really) has scab more than 21.
Comparison medicament: 3% benziothiazolinone wettable powder, registration card PD20100161, the big HuaTe Science industry in west, Shaanxi has
Limit company, commercial.
The field control effectiveness test result of citrus bacterial canker disease prevented and treated by table 5
Result of the test: as shown in Table 5, from the preventive effect of preventing and treating citrus bacterial canker disease, methylsulfonyl bacterium azoles+benziothiazolinone and single dose
Methylsulfonyl bacterium azoles or benziothiazolinone are compared, and in the case of effective ingredient consumption is identical even less, methylsulfonyl bacterium azoles+benziothiazolinone is prevented
Control 14d prevention effect (effective ingredient dosage 15g/667m of citrus bacterial canker disease2) it is respectively higher than single dose methylsulfonyl bacterium azoles (effectively
Composition dosage 15g/667m2) and benziothiazolinone (effective ingredient dosage 20g/667m2) prevention effect be more than 15.56% and
18.4%；And remaining to reach the preventive effect of more than 69% at 14d, the lasting period is long.
The field control effectiveness test of preventing and treating cucumber bacterial angular leaf spot:
Test method: with reference to GB/T17980.103-2004 pesticide field efficacy medicine test criterion (two) the 110th part: sterilization
Agent preventing and treating cucumber bacterial angular leaf spot.
Test site: Nanning doube bridge
Experimental plot: choose 24 communities, random alignment, each community 20, each process 4 repetition；
Test method: using directed spraying method, dispenser for the first time is spaced apart 7 days away from second time spraying time.
Investigation method: the diagonal five-point type sampling of every community, every 3 strains, investigates whole blade, accounts for every leaf lesion area
The percentage ratio classification of total leaf area；Investigate before dispenser once, within after dispenser 7 days and 14 days, investigate respectively once.
Stage division:
0 grade: blade is without scab；
1 grade: lesion area accounts for less than the 5% of whole leaf area；
3 grades: lesion area accounts for the 6%～10% of whole leaf area；
5 grades: lesion area accounts for the 11%～25% of whole leaf area；
7 grades: lesion area accounts for the 26%～50% of whole leaf area；
9 grades: lesion area accounts for more than the 51% of whole leaf area.
Comparison medicament: 3% benziothiazolinone wettable powder, registration card PD20100161, the big HuaTe Science industry in west, Shaanxi has
Limit company, commercial.
The field control effectiveness test result of cucumber bacterial angular leaf spot prevented and treated by table 6
Result of the test: as shown in Table 6, from the preventive effect of preventing and treating cucumber bacterial angular leaf spot, methylsulfonyl bacterium azoles+benziothiazolinone
Compared with single dose methylsulfonyl bacterium azoles or benziothiazolinone, in the case of effective ingredient consumption is identical even less, methylsulfonyl bacterium azoles+thiophene
14d prevention effect (effective ingredient dosage 10g/667m of mould ketone preventing and treating cucumber bacterial angular leaf spot2) it is respectively higher than single dose first
Sulphur sulfonyl bacterium azoles (effective ingredient dosage 15g/667m2) and benziothiazolinone (effective ingredient dosage 20g/667m2) prevention effect
Being more than 19.39% and 19.07, and remain to reach the preventive effect of more than 70% at 14d, the lasting period is long.
Claims (8)
1. one kind contains methylsulfonyl bacterium azoles and the complex composition of benziothiazolinone, it is characterised in that described complex composition is with methylsulfonyl
Bacterium azoles and benziothiazolinone are main active, wherein the chemical name of methylsulfonyl bacterium azoles be 2-(to fluorophenyl)-5-mesyl-
1,3,4-diazole；The weight ratio of methylsulfonyl bacterium azoles and benziothiazolinone is (100 ~ 1): (1 ~ 40).
The most according to claim 1 containing methylsulfonyl bacterium azoles and the complex composition of benziothiazolinone, it is characterised in that described methylsulfonyl
The weight ratio of bacterium azoles and benziothiazolinone is (40 ~ 1): (1 ~ 10).
The most according to claim 1 containing methylsulfonyl bacterium azoles and the complex composition of benziothiazolinone, it is characterised in that described methylsulfonyl
The weight ratio of bacterium azoles and benziothiazolinone is (20 ~ 1): (1 ~ 5).
4. one kind contain methylsulfonyl bacterium azoles and the preparation of benziothiazolinone, it is characterised in that contain by weight 0.1～90% right will
Seeking 1-3 arbitrary described complex composition, remaining is acceptable auxiliary agent and carrier on pesticide, is then prepared as preventing and treating crop
The antibacterial of disease.
The most according to claim 4 containing methylsulfonyl bacterium azoles and the preparation of benziothiazolinone, it is characterised in that described antibacterial with
Weight meter contains 1～80% arbitrary described complex composition of claim 1-3.
6. according to described in claim 4 or 5 containing methylsulfonyl bacterium azoles and the preparation of benziothiazolinone, it is characterised in that described antibacterial
It is configured to water dispersible granules, wettable powder, microemulsion, suspending agent, aqueous emulsion, cream, suspension seed-coating agent.
7. the application of the arbitrary described complex composition of claim 1-3, it is characterised in that described complex composition is used for preventing
Control crop bacterial disease and/or fungal disease, described bacterial disease and/or fungal disease be soft rot of cabbage,
Watermelon blight, cucumber bacterial angular leaf spot and downy mildew, tobacco bacterial wilt, citrus bacterial canker disease and shot hole, X. c. pv. oryzicola
With bacterial leaf-blight, Fructus Lycopersici esculenti shot hole and Peptic Ulcers, downy mildew of garpe, the melon and bacterial wilt of solanaceous vegetable.
8. claim 4-6 is arbitrary described containing methylsulfonyl bacterium azoles and the application of the preparation of benziothiazolinone, it is characterised in that described
Antibacterial is used for preventing and treating crop bacterial disease and/or fungal disease, described bacterial disease and/or fungal disease
Soft rot of cabbage, watermelon blight, cucumber bacterial angular leaf spot and downy mildew, tobacco bacterial wilt, citrus bacterial canker disease and shot hole,
X. c. pv. oryzicola and bacterial leaf-blight, Fructus Lycopersici esculenti shot hole and Peptic Ulcers, downy mildew of garpe, the melon and bacterial wilt of solanaceous vegetable.
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| CN101812034B (en) * | 2010-05-11 | 2011-12-14 | 贵州大学 | 2-substituent-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole derivative, synthetic method and application thereof |
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