WO2018157649A1 - Composition microbicide contenant un dérivé d'émodine et de la benzisothiazolinone - Google Patents

Composition microbicide contenant un dérivé d'émodine et de la benzisothiazolinone Download PDF

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Publication number
WO2018157649A1
WO2018157649A1 PCT/CN2017/116695 CN2017116695W WO2018157649A1 WO 2018157649 A1 WO2018157649 A1 WO 2018157649A1 CN 2017116695 W CN2017116695 W CN 2017116695W WO 2018157649 A1 WO2018157649 A1 WO 2018157649A1
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Prior art keywords
emodin
aloe
methyl ether
active component
mbit
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PCT/CN2017/116695
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English (en)
Chinese (zh)
Inventor
仲汉根
季自华
季红进
花伟
季定根
韦建峰
王莹
王英
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江苏辉丰生物农业股份有限公司
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Publication of WO2018157649A1 publication Critical patent/WO2018157649A1/fr

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    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals

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 a emodin derivative and benzisothiazolinone.
  • Both Physcion and Aloeemodin belong to terpenoids.
  • these compounds are widely used, such as immunoregulation, scavenging oxygen free radicals, antibacterial, anti-inflammatory, antiviral effects, diuretic effects, protective effects on cerebral ischemic injury, cardiovascular pharmacological effects, and anti-tumor effects.
  • these terpenoids are gradually being used in agriculture for the control of fungal or bacterial diseases.
  • This kind of compound is a kind of high-activity plant-derived fungicide extracted from the roots and stems of Chinese herbal plant rhubarb. It is a terpenoid compound, powdery mildew, downy mildew, gray mold, anthrax on vegetables, fruits, grains, etc.
  • Diseases and other diseases have good control effects. At the same time, they are low-toxic to humans and animals, environmentally friendly, and have no cross-resistance with other chemical agents. They have good systemic conduction and strong persistence. Its bactericidal mechanism is to interfere with the biosynthesis of chitin in the cell wall of pathogenic fungi, inhibit the germination of pathogenic spores, the growth of hyphae, the formation of aspirator, thereby blocking the spread of the disease, and also induce the crop to produce an anti-retroviral reaction. The effect of disease prevention.
  • 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.
  • 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 process for the preparation of a bactericidal composition comprising two active ingredients A and B and to combat crop diseases in the agricultural sector.
  • the object of the invention can be achieved by the following measures:
  • a bactericidal composition comprising two active components A and B, wherein the active component A is one of emodin derivatives selected from the group consisting of emodin methyl ether and aloe emodin, wherein the active component A Component B is a structural compound having the formula (I), and the weight ratio between the two components is from 10 to 1:1 to 50.
  • 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 used for controlling bacterial or fungal diseases of crops, and the control effect is obvious, 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 of the active component A to the active component B is from 1:1 to 40, and the weight ratio may be more preferably from 1:1 to 30 in order to make the effect more remarkable. Still more preferably, the weight ratio of emodin methyl ether to 1,2-benzisothiazolin-3-one is 1:1 to 30.
  • 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, 1:31, 1:32, 1:33, 1: 34, 1:35, 1:36, 1:37, 1:38, 1:39, 1:40, 1:41, 1:42, 1:43, 1:44, 1:45, 1:46, 1:47, 1:48, 1:49, 1:50, it is also possible to select within the range of any two of the above ratios, which can be understood as a weight ratio or a molar ratio.
  • 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 1 to 85% by weight of the active ingredient and from 99 to 15% by weight of the pesticide adjuvant or 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 dosage forms acceptable for pesticides, including but not limited to emulsifiable concentrates, suspending agents, wettable powders, water-dispersible granules, powders, granules, aqueous preparations, aqueous emulsions, microemulsions, micro
  • the dosage form of the present invention is a suspending agent, a liquid, a wettable powder or an aqueous emulsion.
  • the compositions may be applied by spraying, misting, dusting, spreading or pouring, and the like.
  • the active component B may be first dissolved in a basic substance to form a benzisothiazolin metal salt.
  • Suitable basic substances include: alkali metal carbonates, alkali metal hydroxides (such as hydroxides). Sodium, potassium hydroxide), alkali metal alkoxy carbonate, alkali metal alkoxide or magnesium methoxide.
  • 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 Sulfates, alkyl sulfonates, fatty alcohol sulphates, fatty acids and sulfated fatty alcohol glycol ethers, as well as condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, naphthalene or naphthalene sulfonic acid with phenol and formaldehyde Condensate, polyoxyethylene octyl phenyl ether, ethoxylated isooctyl phenol, octyl phenol, nonyl phenol, alkyl aryl polyglycol ether, tributyl benzene poly
  • 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 agricultural field for controlling crop diseases, and the crop diseases referred to herein are grape powdery mildew, cucumber powdery mildew, cucumber downy mildew, bitter gourd powdery mildew, tomato gray mold disease, wheat powdery mildew. Rice blast disease.
  • the composition of the present invention can prevent and cure specific diseases including but not limited to wheat diseases (such as wheat scab, wheat powdery mildew, wheat rust, etc.), rice diseases (such as rice stalks).
  • corn diseases such as: corn smut, corn big spot, corn small spot disease
  • cucumber diseases such as: cucumber powdery mildew, cucumber anthracnose, cucumber Botrytis, cucumber bacterial leaf spot, etc.
  • tomato diseases eg tomato powdery mildew, tomato anthracnose, tomato virus disease, tomato bacterial angular spot disease, etc.
  • grape diseases eg grape downy mildew, grapes
  • Gray mold apple diseases
  • apple ring disease apple anthracnose, etc.
  • citrus diseases such as: citrus scab, citrus anthracnose
  • tobacco diseases such as: tobacco wildfire, tobacco brown spot disease
  • rape Diseases such as: Sclerotinia sclerotiorum
  • cotton diseases such as: cotton verticillium wilt, cotton blight.
  • 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 very different, the mechanism of action is completely Different, there is no cross-resistance, which can delay the resistance problem caused by the two single agents used alone; 3.
  • the composition of the invention is safe and effective against 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 ingredient B are mixed with the components such as the surfactant and water in a ratio of the formulation to obtain a finished product.
  • Active ingredient A emodin methyl ether
  • active ingredient B BIT
  • Example 1 2.2% emodin methyl ether BIT water (10:1)
  • Active ingredient A emodin methyl ether
  • active component B MBIT
  • Example 3 2.2% emodin methyl ether ⁇ MBIT water agent
  • the emodin methyl ether was 0.25%, MBIT was 5%, and the remaining components were prepared in accordance with the method of Example 2.
  • the emodin methyl ether was 0.25%, BBIT was 5%, and the remaining components were prepared in accordance with the method of Example 2.
  • Active ingredient A aloe emodin
  • active ingredient B BIT
  • Aloe-emodin 0.25%, BIT 5%, and the remaining components were prepared according to the method of Example 2.
  • Active ingredient A aloe emodin
  • active ingredient B MBIT
  • Aloe-emodin 0.25%, MBIT 5%, and the remaining components were prepared according to the method of Example 2.
  • Active ingredient A (aloe emodin) and active ingredient B (BBIT) preparation of water agent
  • Aloe-emodin 0.25%, BBIT 5%, and the remaining components were prepared according to the method of Example 2.
  • 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% emodin methyl ether ⁇ BIT wettable powder (1:1)
  • Example 14 15.5% emodin methyl ether ⁇ BIT wettable powder (1:30)
  • Example 15 6% emodin methyl ether ⁇ MBIT wettable powder
  • Example 16 15.5% emodin methyl ether ⁇ MBIT wettable powder
  • the emodin methyl ether was 0.5%, the MBIT was 15%, and the remaining components were prepared in the same manner as in Example 14.
  • Example 17 6% emodin methyl ether ⁇ BBIT wettable powder
  • Example 18 15.5% emodin methyl ether ⁇ BBIT wettable powder
  • Example 19 6% aloe-emodin ⁇ BIT wettable powder
  • Example 20 15.5% aloe-emodin ⁇ BIT wettable powder
  • Example 21 6% aloe-emodin ⁇ MBIT wettable powder
  • Example 22 15.5% aloe-emodin ⁇ MBIT wettable powder
  • Example 23 6% aloe-emodin BBIT wettable powder
  • Example 24 15.5% aloe-emodin BBIT wettable powder
  • the active ingredient A and the B active ingredient are mixed well with a solvent, an emulsifier, a dispersing agent, an antifreezing agent, etc., and the water emulsion is prepared by adding water and then uniformly mixing.
  • Example 25 2.75% emodin methyl ether BIT water emulsion (1:10)
  • Example 27 5.1% emodin methyl ether BIT water emulsion (1:50)
  • the emodin methyl ether was 0.25%, the MBIT was 2.5%, and the remaining components were prepared in accordance with the procedure of Example 25.
  • the emodin methyl ether was 0.25%, the MBIT was 10%, and the remaining components were prepared in the same manner as in Example 26.
  • Example 30 5.1% emodin methyl ether ⁇ MBIT water emulsion
  • the emodin methyl ether was 0.25%, BBIT was 2.5%, and the remaining components were prepared in accordance with the procedure of Example 25.
  • Example 33 5.1% emodin methyl ether BBIT water emulsion
  • Aloe-emodin 0.25%, BIT 10%, and the remaining components were prepared according to the method of Example 26.
  • Example 36 5.1% aloe emodin ⁇ BIT water emulsion
  • Aloe-emodin 0.25%, MBIT 2.5%, and the remaining components were prepared according to the method of Example 25.
  • Aloe-emodin 0.25%, MBIT 10%, and the remaining components were prepared according to the method of Example 26.
  • Example 39 5.1% aloe-emodin ⁇ MBIT water emulsion
  • Example 40 2.75% aloe-emodin BBIT water emulsion
  • Aloe-emodin 0.25%, BBIT 10%, and the remaining components were prepared according to the method of Example 26.
  • Example 42 5.1% aloe-emodin BBIT water emulsion
  • the control effect is converted into the probability value (y)
  • the concentration of the drug solution ( ⁇ g/ml) is converted into the logarithm value (x)
  • the virulence equation is calculated by the least squares method and the concentration EC50 is suppressed
  • the virulence index of the drug is calculated according to the method of Sun Yunpei.
  • the co-toxicity coefficient (CTC) is calculated according to the method of Sun Yunpei.
  • 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)
  • 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)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une composition microbicide contenant un dérivé d'émodine et de la benzisothiazolinone. La composition contient deux ingrédients efficaces, c'est-à-dire A et B. Le principe actif A est la pariétine ou l'aloès d'émodine, le principe actif B est un composé structurel de formule (I), et le rapport pondéral des deux composants est de 10-1 : 1-50. L'invention concerne également un procédé de préparation de cette composition et son utilisation. Les résultats des tests montrent que la composition microbicide ci-dessus fournie par la présente invention a un effet synergique significatif, et il est également à noter que la quantité d'application de celle-ci est réduite et le coût d'utilisation de celle-ci est réduit. La composition bactéricide permet de lutter efficacement contre certaines maladies bactériennes ou fongiques spécifiques des cultures. En mélangeant des microbicides ayant des mécanismes d'action et des modes d'action différents, la composition a de bons effets en ce qui concerne l'expansion du spectre bactéricide, le retardement de la résistance des bactéries, et l'amélioration des effets de lutte, etc. Dans la formule (I), R est choisi parmi H ou un alkyle en C1-C8.
PCT/CN2017/116695 2017-02-28 2017-12-16 Composition microbicide contenant un dérivé d'émodine et de la benzisothiazolinone WO2018157649A1 (fr)

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CN201710112986.5A CN106942240B (zh) 2017-02-28 2017-02-28 一种包含大黄素衍生物与苯并异噻唑啉酮的杀菌剂组合物

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CN110537542A (zh) * 2018-12-13 2019-12-06 北京宇悦生物科技有限公司 农药组合物及其应用
CN110537548A (zh) * 2018-12-13 2019-12-06 北京宇悦生物科技有限公司 农药组合物及其应用
CN112480031B (zh) * 2020-11-26 2022-05-20 江苏海洋大学 含1,3,4-噻二唑的大黄素酰胺类衍生物及合成方法与用途
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