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WO2018059606A1 - Composition bactéricide contenant de la benzisothiazolinone et du mandipropamide - Google Patents

Composition bactéricide contenant de la benzisothiazolinone et du mandipropamide Download PDF

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Publication number
WO2018059606A1
WO2018059606A1 PCT/CN2017/113035 CN2017113035W WO2018059606A1 WO 2018059606 A1 WO2018059606 A1 WO 2018059606A1 CN 2017113035 W CN2017113035 W CN 2017113035W WO 2018059606 A1 WO2018059606 A1 WO 2018059606A1
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WO
WIPO (PCT)
Prior art keywords
composition
dipropionamide
active component
composition according
bactericidal composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/CN2017/113035
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English (en)
Chinese (zh)
Inventor
仲汉根
季自华
季红进
花伟
韦建峰
季定根
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangsu Huifeng Bio Agriculture Co Ltd
Original Assignee
Jiangsu Huifeng Bio Agriculture Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication of WO2018059606A1 publication Critical patent/WO2018059606A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids

Definitions

  • the invention belongs to the field of agricultural plant protection, in particular to a germicidal composition with improved properties, in particular to a germicidal composition comprising benzisothiazolinones and dipropionin.
  • Benzoisothiazolinones are a new type of broad-spectrum fungicide mainly used for the prevention and treatment of various bacterial and fungal diseases such as cereal crops, vegetables and fruits.
  • the mechanism of bactericidal action mainly includes destroying the nuclear structure of the pathogen, causing it to lose the heart part and failing to death and interfering with the metabolism of the pathogenic cells, causing its physiological disorder and ultimately leading to death. It can effectively protect plants from pathogens in the early stage of disease occurrence. Increasing the dosage after disease occurrence can obviously control the spread of pathogens, thus achieving the dual functions of protection and eradication.
  • Mandipropamid is an amide fungicide. Its mechanism of action is to inhibit the biosynthesis of phospholipids, and it has good control effect on the majority of leaf and fruit diseases caused by oomycetes. It has high activity against spores in the germination stage and inhibits mycelial growth and sporulation. It can be quickly absorbed by the leaves and stays in the leaf wax layer to protect the leaves.
  • the object of the present invention is to solve the resistance of the bactericide in practical application and the problem of soil residue, and to screen out the fungicides with different sterilization principles to obtain a new fungicide composition, so as to improve the control effect of the bactericide and delay the resistance.
  • Sexual production reducing the amount of application, reducing the cost of prevention.
  • Another object of the present invention is to provide a bactericidal composition comprising two active ingredients A and B and their use in controlling agricultural crop diseases in the agricultural field.
  • the object of the invention can be achieved by the following measures:
  • a synergistic fungicidal composition comprising two active components A and B, wherein active component A is a structural compound having formula (I) and active component B is dipropionin .
  • R is selected from H or a C 1 - C 8 alkyl group.
  • the C 1 -C 8 alkyl group in the present invention means a linear or branched alkyl group having 1 to 8 carbon atoms, and includes a C 1 alkyl group (e.g., methyl group) and a C 2 alkyl group (e.g., ethyl group). , C 3 alkyl (such as n-propyl, isopropyl), C 4 alkyl (such as n-butyl, isobutyl, tert-butyl, sec-butyl), C 5 alkyl (such as n-pentyl, etc.) , C 6 alkyl, C 7 alkyl, C 8 alkyl. It includes, but is not limited to, C 1 -C 6 alkyl, C 1 -C 5 alkyl, C 1 -C 4 alkyl, and the like.
  • R is selected from H or a C 1 -C 4 alkyl group.
  • R is selected from the group consisting of H, -CH 3 or -C 4 H 9 .
  • A is 1,2-benzisothiazolin-3-one (abbreviated as BIT in the specification).
  • R is CH 3
  • A is 2-methyl-1,2-benzisothiazolin-3-one (abbreviated as MBIT in the specification).
  • R is C 4 H 9
  • A is 2-butyl-1,2-benzisothiazolin-3-one
  • the "butyl group” in the formula is preferably n-butyl (instruction Referred to as BBIT).
  • the inventors have found through experiments that the composition of the present invention is effective for controlling bacterial or fungal diseases of crops, and more importantly, the application amount is reduced and the use cost is lowered.
  • the compounds containing component A and component B have different structural types and different mechanisms of action. The combination of the two can expand the bactericidal spectrum, and can delay the generation and development of pathogen resistance to a certain extent, and component A and group There is no cross-resistance between points B.
  • the weight ratio between the two components in the bactericide composition of the present invention is from 10 to 1:1 to 30.
  • the weight ratio between the two components of the components A and B can be further optimized to 5 to 1:1 to 20.
  • the weight ratio between the two components of A and B can be arbitrarily adjusted within the range of the following ratios: 10:1, 9:1, 8:1, 7:1, 6:1 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1: 9, 1:10, 1:11, 1:12, 1:13, 1:14, 1:15, 1:16, 1:17, 1:18, 1:19, 1:20, 1:21, 1:22, 1:23, 1:24, 1:25, 1:26, 1:27, 1:28, 1:29, 1:30, or within the range of any two of the above ratios Selection is made, and these ratios can be understood as weight ratios, and may also include molar ratios.
  • composition of the present invention can be made into a pesticide-acceptable dosage form from the active ingredient and agrochemical adjuvant or adjuvant. Further, the composition comprises from 2 to 80% by weight of the active ingredient and from 98 to 20% by weight of the pesticide adjuvant to form a pesticide-acceptable dosage form.
  • the present invention provides the use of a bactericidal composition comprising component A and component B for controlling crop diseases in the agricultural sector, in particular for controlling fungal or bacterial diseases of certain crops.
  • composition may specifically comprise an agrochemical adjuvant or an auxiliary such as one or more of a carrier, a solvent, a dispersing agent, a wetting agent, an adhesive, a thickener, a binder, a surfactant or a fertilizer.
  • auxiliary such as one or more of a carrier, a solvent, a dispersing agent, a wetting agent, an adhesive, a thickener, a binder, a surfactant or a fertilizer.
  • auxiliary such as one or more of a carrier, a solvent, a dispersing agent, a wetting agent, an adhesive, a thickener, a binder, a surfactant or a fertilizer.
  • auxiliary such as one or more of a carrier, a solvent, a dispersing agent, a wetting agent, an adhesive, a thickener, a binder, a surfactant or a fertilizer.
  • Common auxiliaries can be mixed during the application.
  • auxiliaries or auxiliaries may be solid or liquid, they are usually materials commonly used in the processing of dosage forms, such as natural or regenerated minerals, solvents, dispersants, wetting agents, adhesives, thickeners, binders. .
  • the method of application of the compositions of the invention comprises the use of the compositions of the invention for aerial parts of plants, in particular leaves or foliage. You can choose to soak or apply to the surface of the control object.
  • the frequency of administration and the amount administered will depend on the biological and climatic conditions of the pathogen.
  • the plant growth site such as rice fields, may be wetted with a liquid formulation of the composition, or the composition may be applied to the soil in solid form, such as in the form of granules (soil application), the composition may be passed from the soil to the plant through the roots of the plant. In vivo (systemic action).
  • composition of the present invention can be prepared into various pesticide-acceptable dosage forms including, but not limited to, emulsifiable concentrates, suspending agents, wettable powders, water-dispersible granules, powders, granules, aqueous preparations, aqueous emulsions, microemulsions, poison baits.
  • the dosage form of the invention employs a wettable powder, a suspending agent, a water-dispersible granule, an aqueous emulsion or a microemulsion.
  • the compositions may be applied by spraying, misting, dusting, spreading or pouring, and the like.
  • composition of the present invention can be prepared into various dosage forms by a known method, and the active ingredient and the auxiliary agent, such as a solvent, a solid carrier, and, if necessary, can be uniformly mixed and ground together with the surfactant to prepare a desired preparation. Dosage form.
  • the above solvent may be selected from aromatic hydrocarbons, preferably containing from 8 to 12 carbon atoms, such as a mixture of xylenes or substituted benzenes, phthalates such as dibutyl phthalate or dicaprylic acid, aliphatic hydrocarbons such as rings.
  • aromatic hydrocarbons preferably containing from 8 to 12 carbon atoms, such as a mixture of xylenes or substituted benzenes, phthalates such as dibutyl phthalate or dicaprylic acid, aliphatic hydrocarbons such as rings.
  • Alkenes or paraffins, alcohols and glycols and their ethers and esters such as ethanol, ethylene glycol, ethylene glycol monomethyl
  • ketones such as cyclohexanone
  • highly polar solvents such as N-methyl-2 Pyrrolidone, dimethyl sulfoxide or dimethylformamide
  • vegetable or vegetable oils such as soybean oil.
  • the above solid carriers are typically natural mineral fillers such as talc, kaolin, montmorillonite or activated clay.
  • a highly dispersible silicic acid or a highly dispersible adsorbent polymer carrier such as a particulate adsorbent carrier or a non-adsorbing carrier, and a suitable particulate adsorbent carrier is porous, such as pumice, bentonite or Bentonite; a suitable non-adsorbing carrier such as calcite or sand.
  • a large amount of pre-granulated materials of inorganic or organic nature can be used as a carrier, in particular dolomite.
  • Suitable surfactants are lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, alkaline earth metal or amine salts, alkylarylsulfonates, alkyl groups Sulfate, alkyl sulfonate, fatty alcohol sulfur Acid salt, fatty acid and sulfated fatty alcohol glycol ether, condensate of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensate of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octyl phenyl ether , ethoxylated isooctyl phenol, octyl phenol, nonyl phenol, alkyl aryl polyglycol ether, tributyl benzene polyglycol
  • the active ingredient A can be first dissolved in certain specific basic substances to form a benzisothiazolin metal salt.
  • suitable basic substances include: alkali metal carbonates, alkali metal hydrogens Oxide (such as sodium hydroxide, potassium hydroxide), alkali metal alkoxy carbonate, alkali metal alkoxide or magnesium methoxide.
  • the two active ingredients in the compositions of the present invention exhibit synergistic effects, the activity of which is more pronounced than the expected sum of activity using a single compound, and the individual activity of a single compound.
  • the synergistic effect is manifested by allowing for a reduced application rate, a broader fungicidal control profile, quicker effect, longer lasting control effect, better control of plant harmful fungi by only one or a few applications, and broadening of possible application. Intervals. These properties are particularly desirable in the practice of plant fungi control.
  • the fungicide composition of the invention can be applied to the field of agricultural diseases for controlling crop diseases, and the specific diseases targeted include, but not limited to, wheat diseases (such as wheat scab, wheat powdery mildew, wheat rust, etc.) and rice diseases (such as: Rice sheath blight, rice blast disease, rice blast, rice bacterial streaks, etc., corn diseases (such as: corn smut, corn big spot, corn spot), cucumber diseases (such as: cucumber frost Mold disease, cucumber powdery mildew, cucumber anthracnose, cucumber bacterial angular spot disease, etc., tomato diseases (such as: tomato anthracnose, tomato gray mold, tomato bacterial angular spot disease, etc.), grape diseases (such as: grape frost Mildew, grape gray mold, grape powdery mildew), apple disease (such as apple ring disease, apple anthracnose, etc.), citrus disease (citrus canker disease, citrus canker, citrus anthracnose), tobacco disease (tobacco wildfire disease) )Wait.
  • the other characteristics exhibited by the bactericidal composition of the present invention are mainly as follows: 1.
  • the compounding of the composition of the present invention has obvious synergistic effect; 2. Since the chemical composition of the two single agents of the present composition is greatly different, the effect The mechanism is completely different, there is no cross-resistance, and the problem of resistance caused by the separate use of the two single agents can be delayed; 3.
  • the composition of the present invention is safe and safe for crops. It has been proved by experiments that the bactericidal composition of the invention has stable chemical properties, remarkable synergistic effect, and exhibits obvious synergistic effect and complementary effect on the control object.
  • the active ingredient active group A and the active component B, and the auxiliary agent and the filler are uniformly mixed according to the formula, and are pulverized into a wettable powder by a jet stream, and then added with a certain amount of water to be mixed and extruded, granulated, and dried and sieved.
  • a water dispersible granule product A water dispersible granule product.
  • Example 2 54% BIT ⁇ dipropionamide water dispersible granules (1:5)
  • Example 3 11% MBIT ⁇ dipropionamide water dispersible granules
  • Example 4 54% MBIT ⁇ dipropionamide water dispersible granules
  • MBIT was 9%, dipropionamide 45%, and the remaining components were prepared in the same manner as in Example 2.
  • Example 5 11% BBIT ⁇ dipropionamide water dispersible granules
  • Example 6 54% BBIT ⁇ dipropionamide water dispersible granules
  • the active ingredient active group A and the active component B, and the components such as a dispersing agent, a wetting agent, a thickener and water are uniformly mixed according to the formula, and after being sanded and/or sheared at a high speed, a semi-finished product is obtained. After the analysis, the water is mixed and evenly filtered to obtain the finished product.
  • Example 7 10% BIT ⁇ dipropionamide suspension (1:1)
  • MBIT was 5%, bis-profenamide 5%, and the remaining components were prepared in accordance with the procedure of Example 7.
  • the active ingredient A and the B active ingredient are sufficiently mixed with various auxiliary agents and fillers, and are pulverized by an ultrafine pulverizer to obtain a wettable powder.
  • Example 13 6% BIT ⁇ dipropionamide wettable powder (5:1)
  • Example 14 22% BIT ⁇ dipropionamide wettable powder (1:10)
  • Example 15 77.5% BIT ⁇ dipropionamide wettable powder (1:30)
  • Example 16 6% MBIT ⁇ dipropionamide wettable powder
  • Example 17 22% MBIT ⁇ dipropionamide wettable powder
  • Example 18 77.5% MBIT ⁇ dipropionamide wettable powder
  • Example 19 6% BBIT ⁇ dipropionamide wettable powder
  • Example 20 22% BBIT ⁇ dipropionamide wettable powder
  • Example 21 77.5% BBIT ⁇ dipropionamide wettable powder
  • the control effect is converted into the probability value (y), the liquid height ( ⁇ g/ml) is converted into a logarithmic value (x), the virulence equation is calculated by the least squares method, and the neutral concentration EC50 is suppressed, and the virulence of the drug is calculated according to the method of Sun Yunpei. Exponential Co-toxicity Factor (CTC).
  • CTC Exponential Co-toxicity Factor
  • Measured virulence index (ATI) (standard drug EC50 / test drug EC50) * 100
  • Theoretical virulence index (TTI) A virulence index * Percentage of A in the mixture + B virulence index * Percentage of B in the mixture
  • CTC Co-toxicity coefficient [mixture measured virulence index (ATI) / mixed theory virulence index (TTI)] * 100
  • CTC ⁇ 80 the composition showed antagonism, 80 ⁇ CTC ⁇ 120, the composition showed an additive effect, CTC ⁇ 120, and the composition showed synergistic effect.
  • Test method In the early stage of the disease, the first spray was immediately performed, and after 7 days, the second application was carried out, each treatment of 4 cells, 20 square meters per cell. The incidence of the disease was investigated before the drug and 11 days after the second drug. Each plot was randomly sampled at 5 points, and 5 crops were investigated at each point. The percentage of the lesion area per leaf on the whole plant was counted and graded. Disease index and control effect.
  • Grade 1 less than 5 leaf lesions, less than 1 cm in length;
  • Grade 3 6-10 leaf lesions, some lesions are longer than 1 cm;
  • Grade 5 11-25 leaf lesions, some lesions are connected into pieces, and the lesion area accounts for 10-25% of the leaf area;
  • Grade 7 more than 26 leaf lesions, the lesions are connected into pieces, and the lesion area accounts for 26-50% of the leaf area;
  • Grade 9 The lesions are connected into pieces, and the area of the lesions accounts for more than 50% of the leaf area or the whole leaves are dead.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une composition bactéricide, ladite composition comprenant deux principes actifs, A et B, le principe actif A étant un composé ayant une structure répondant à la formule (I), le principe actif B étant le mandipropamide, dans un rapport en poids des deux composants de 10-1:1-30. L'invention concerne également un procédé de préparation de la composition et son utilisation. Les résultats d'essais montrent que la composition bactéricide selon la présente invention a une synergie significative et, plus important, engendre des quantités d'application réduites et des coûts d'usage en baisse. La présente composition bactéricide empêche et traite efficacement certaines maladies bactériennes ou fongiques des cultures. Le mélange de bactéricides ayant des mécanismes et des modes d'action différents élargit le spectre bactéricide, retarde la résistance aux champignons et aux bactéries, et améliore l'effet de prévention et de traitement.
PCT/CN2017/113035 2016-09-28 2017-11-27 Composition bactéricide contenant de la benzisothiazolinone et du mandipropamide Ceased WO2018059606A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201610864318.3A CN106359404A (zh) 2016-09-28 2016-09-28 含有苯并异噻唑啉酮类和双炔酰菌胺的杀菌组合物
CN201610864318.3 2016-09-28

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Cited By (2)

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US10544112B2 (en) * 2017-03-29 2020-01-28 University Of Kentucky Research Foundation Identification of ebsulfur analogues with broad-spectrum antifungal activity
CN114349569A (zh) * 2021-01-26 2022-04-15 广西壮族自治区农业科学院 一种生态调理型桉树专用肥及其制备方法

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CN108812684A (zh) * 2018-09-28 2018-11-16 陕西西大华特科技实业有限公司 一种含噻霉酮和丁吡吗啉的组合杀菌物
CN110037041A (zh) * 2019-04-30 2019-07-23 三河市霍夫曼化学品制造有限公司 一种异噻唑啉酮类复配微乳型杀菌防霉剂、其制备方法及应用
CN115487181B (zh) * 2020-09-07 2024-03-12 南京艾力彼兽药研究所有限公司 异噻唑啉酮作为抗菌药物的增效剂的应用
CN112544622B (zh) * 2020-12-23 2021-07-02 广西安农聚智科技有限公司 一种用于火龙果溃疡病炭疽病防治剂的制备方法

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US10544112B2 (en) * 2017-03-29 2020-01-28 University Of Kentucky Research Foundation Identification of ebsulfur analogues with broad-spectrum antifungal activity
CN114349569A (zh) * 2021-01-26 2022-04-15 广西壮族自治区农业科学院 一种生态调理型桉树专用肥及其制备方法
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