CN116349686A - Fungicidal composition containing substituted triazolinone ether compound and application thereof - Google Patents

Fungicidal composition containing substituted triazolinone ether compound and application thereof Download PDF

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CN116349686A
CN116349686A CN202111614454.4A CN202111614454A CN116349686A CN 116349686 A CN116349686 A CN 116349686A CN 202111614454 A CN202111614454 A CN 202111614454A CN 116349686 A CN116349686 A CN 116349686A
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alkyl
methyl
acid
general formula
active component
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Inventor
兰杰
孙庚�
杨吉春
孙芹
李志念
李轲轲
王斌
刘长令
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Jiangsu Yangnong Chemical Co Ltd
Shenyang Sinochem Agrochemicals R&D Co Ltd
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Jiangsu Yangnong Chemical Co Ltd
Shenyang Sinochem Agrochemicals R&D Co Ltd
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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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N37/44—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 nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—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 nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

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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

The invention belongs to the field of agricultural bactericides, and in particular relates to a fungicidal composition and application thereof. The composition comprises A, B two active components, wherein the weight ratio of the active component A to the active component B is 1:99-99:1; the active component A is selected from compounds shown in the following general formula I and salts thereof, and the active component B is selected from respiratory inhibitor bactericides. The invention killsThe bacterial composition is particularly suitable for controlling a variety of phytopathogenic fungal diseases, such as powdery mildew, anthracnose, leaf spot, downy mildew, anthracnose, white rot, epidemic disease, cladosporium cucumerinum, rust, scab, leaf mold, gray mold, clubroot, black nevus, rice blast, sheath blight, sclerotium disease or damping off.

Description

Fungicidal composition containing substituted triazolinone ether compound and application thereof
Technical Field
The invention belongs to the field of agricultural bactericides, and particularly relates to a fungicidal composition for substituting triazolinone ether compounds and respiratory inhibitor bactericides and application thereof.
Background
Patent CN102336744B discloses a compound containing substituted triazolinone ether and its use, wherein the compound shown in the following general formula I is reported to have good activity against various fungal diseases.
Figure BDA0003436289560000011
The respiration inhibitor bactericide inhibits the growth of pathogenic bacteria by acting on the mitochondrial respiratory chain of fungi to block the electron transfer and interfere the energy metabolism, and has good activity on fungus diseases. Most respiratory inhibitor bactericides have wide bactericidal spectrum, have protection and treatment effects and better permeation and systemic effects, but have single action mechanism and action sites, and frequently use for a long time to cause pathogenic bacteria to generate resistance, so that the prevention effect is reduced, and the prevention cost is increased due to the increase of the application dosage and the application times. The composition can make up for the advantages of each medicament and exert the advantages of each medicament through the research and development and application of the composition while developing new medicaments, so that the generation of drug resistance is delayed, the prevention and control objects are enlarged, the administration times are reduced, the cost is reduced, and the economic benefit is improved.
Disclosure of Invention
The invention aims to provide a fungicidal synergistic composition of a substituted triazolinone ether compound and a respiratory inhibitor bactericide and application thereof.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a fungicidal composition comprising A, B two active components, wherein the weight ratio of active component A to active component B is 1:99-99:1;
the active component A is a compound shown in a general formula I or a salt thereof.
Figure BDA0003436289560000012
In the general formula:
q is selected from Q1 or Q2 as shown below:
Figure BDA0003436289560000021
w is selected from O;
R 1 selected from methyl;
when Q is selected from Q1: r is R 2 Selected from hydrogen, halogen, cyano, nitro, CH 2 CN, C1-C6 alkyl, halogenated C1-C6 alkyl or C3-C6 cycloalkyl, R 3 Selected from hydrogen, C1-C6 alkyl or halogenated C1-C6 alkyl;
when Q is selected from Q2: r is R 2 Selected from halogen, C1-C6 alkyl, halogenated C1-C6 alkyl or C3-C6 cycloalkyl, R 3 Selected from C1-C6 alkyl or halogenated C1-C6 alkyl;
R 4 selected from halogen, cyano, nitro, hydroxy, C1-C4 alkyl, halogenSubstituted C1-C3 alkyl, C1-C3 alkoxy, halogenated C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfonyl, phenyl or phenoxy, unsubstituted or substituted with 1 to 5 groups independently selected from chloro, bromo, fluoro, nitro, cyano, trifluoromethyl, C1-C3 alkyl, C1-C3 alkoxy or halogenated C1-C3 alkoxy; n=0-5;
R 5 、R 6 can be identical or different and is selected from hydrogen, halogen, nitro, cyano, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, phenyl, pyridyl, furyl, thienyl or thiazolyl, which are unsubstituted or substituted by 1 to 5 radicals independently selected from halogen, cyano, nitro, CO 2 (C1-C4 alkyl), C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio or C1-C6 alkylsulfonyl;
y is selected from halogen, OR 7 、SR 7 、SOR 7 、SO 2 R 7 Or NHR 7 The method comprises the steps of carrying out a first treatment on the surface of the Wherein R is 7 Selected from hydrogen or C1-C4 alkyl;
the active component B is selected from pyraclostrobin B1, enestroburin B2, azoxystrobin B3, isopyrazam B4, fluxapyroxad hydroxylamine B5, fluazinam B6, trifloxystrobin B7, cyazofamid B8, fluxapyroxad B9, fluopyram B10, fluoroether mycoamide B11, fluorophenylamide B12, fluoroamide B13, thifluzamide B14, benzovindiflupyr B15, penflufen B16, fluxapyroxad B17, ipratropium B18, inpyrfluxam B19, isoflucypram B20, pyraziflumid B21, pyrafungone B22, carboxin B23, fenhexamid B12, fenhexamid B17, penflufen B18, iprovalicarb and pyriproxil B22 one or more of carboxin B24, furbenomyl B25, fenhexamid B26, meflofen B27, silthiopham B28, enestroburin 29, pyraclostrobin 30, pyraclostrobin 31, cyproconazole B32, boscalid B33, bixafen B34, picoxystrobin 35, kresoxim-methyl 36, fluoxastrobin B37, coumoxystrobin B38, kresoxim-methyl B39, chlorpyriproxyfen B40, phenoxypenoxsulam B41, trifloxystrobin B42, benthiavalicarb 43, fenpiclamid B44, florylpicoxamid B45, metarylpicoxamid B, zoxamide B47, pyribenzoxim B48 and penthiopyrad B49.
Preferably, the active component A is selected from compounds represented by the general formula I or salts thereof.
In the general formula:
q is selected from Q1 or Q2 as shown below:
w is selected from O;
R 1 selected from methyl;
when Q is selected from Q1: r is R 2 Selected from hydrogen, fluorine, chlorine, bromine or C1-C4 alkyl, R 3 Selected from hydrogen or C1-C6 alkyl;
when Q is selected from Q2: r is R 2 Selected from C1-C4 alkyl, R 3 Selected from C1-C6 alkyl;
R 4 selected from halogen, cyano, nitro, C1-C4 alkyl, halogenated C1-C3 alkyl, C1-C3 alkoxy, halogenated C1-C3 alkoxy or C1-C3 alkylsulfonyl;
n＝0-3；
R 5 、R 6 which may be the same or different, are each selected from hydrogen, chlorine, bromine, fluorine, nitro, cyano, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy or halogenated C1-C4 alkoxy;
y is selected from Cl, OR 7 Or SR (S.J) 7 The method comprises the steps of carrying out a first treatment on the surface of the Wherein R is 7 Selected from C1-C4 alkyl;
the salt of the compound shown in the general formula I is the salt formed by the compound shown in the general formula I and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid and fumaric acid;
the active component B is selected from pyraclostrobin B1, enestroburin B2, azoxystrobin B3, isopyrazam B4, fluoxastrobin B5, fluoxastrobin B6, trifloxystrobin B7, cyazofamid B8, fluoxastrobin B9, fluopyram B10, fluoxastrobin B11, fluoxastrobin B12, thifluzamide B14, benzovindiflupyr B15, penflufen B16, ipratropium B18, inpyrfluxam B19, isoflucypram B20, pyraziflumid B21, pyrapoyne B22, enestroburin 29, pyraclostrobin 30, pyraclostrobin 31, boscalid B33, bixafen B34, picoxystrobin 35, kresoximide 36, fluoxastrobin B37, coumoxystrobin B38, kresoxim B39, chloromycetin B40, zoxamide B41, zoxamide B42, penciclovir 35, penciclovir B45, penoxsulam 35, penoxsulam 45;
A. the weight ratio of the two active components is 1:50-50:1.
Further preferably, the active component A is selected from the group consisting of compounds of formula I or salts thereof.
In the general formula:
q is selected from Q1 or Q2;
w is selected from O;
R 1 selected from methyl;
when Q is selected from Q1: r is R 2 Selected from hydrogen or methyl, R 3 Selected from hydrogen, methyl or ethyl;
when Q is selected from Q2: r is R 2 Selected from methyl, R 3 Selected from methyl;
R 4 selected from halogen, cyano, nitro, methyl, ethyl, isopropyl, t-butyl, CF 3 、CH 3 O or CF 3 O；
n＝0-3；
R 5 、R 6 May be the same or different and are each selected from hydrogen, chlorine, bromine, fluorine or C1-C4 alkyl;
y is selected from Cl, CH 3 O or CH 3 S；
The salt of the compound shown in the general formula I is a salt formed by the compound shown in the general formula I and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid and benzoic acid.
The active component B is selected from one or more of pyraclostrobin B1, enestroburin B2, azoxystrobin B3, isopyrazam B4, fluoxastrobin B5, fluoxastrobin B6, trifloxystrobin B7, cyazofamid B8, fluoxastrobin B9, fluopyram B10, thifluzamide B14, benzovindiflupyr B15, iprfluxam B19, isoflucypram B20, pyraziflumid B21, pyrapoyne B22, enestroburin 29, pyraclostrobin 30, pyraclostrobin 31, boscalid B33, picoxystrobin 35, kresoxim 36, fluoxastrobin B37, coumoxystrobin B38, fluoxastrobin B40, fenpyraclostrobin B41, fenpiclamid B44, florylpicoxamid B, metarylpicoxamid B, zoxaprop B47 and pyrimethanil B49;
the weight ratio of the A, B active components is 1:20-20:1.
Still further preferably, the active ingredient a is selected from the group consisting of compounds of formula I or salts thereof.
In the general formula:
q is selected from Q2;
w is selected from O;
R 1 selected from methyl;
R 2 selected from methyl, R 3 Selected from methyl;
R 4 selected from fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, CF 3 、CH 3 O or CF 3 O；
n=0, 1, 2 or 3;
R 5 、R 6 may be the same or different and are each selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl or isopropyl;
y is selected from Cl or CH 3 O；
The salt of the compound shown in the general formula I is a salt formed by the compound shown in the general formula I and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid and acetic acid;
the active component B is selected from one or more of pyraclostrobin B1, enestroburin B2, azoxystrobin B3, isopyrazam B4, fluxapyroxad hydroxylamine B5, fluazinam B6, trifloxystrobin B7, fluxapyroxad B9, fluopyram B10, thifluzamide B14, benzovindiflupyr B15, ippyrfluxam B19, isoflucypram B20, pyraziflumid B21, pyrapoyne B22, pyraclostrobin 31, boscalid B33, picoxystrobin 35, coumoxystrobin B38, fenpicloramid B44, florylpicoxamid B, metarylpicoxamid B, zoxamide B47 and pyrithiobacmid B49;
the weight ratio of the A, B active components is 1:10-10:1.
Still further preferably, the active ingredient a is selected from the group consisting of compounds of formula I or salts thereof.
In the general formula:
q is selected from Q2; w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; n=0; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3O);
or Q is selected from Q2; w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; r is R 4 Selected from fluorine; n=1; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3 O)；
Or Q is selected from Q2; w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; r is R 4 Selected from chlorine; n=1; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3 O)；
The salt of the compound shown in the general formula I is a salt formed by the compound shown in the general formula I, hydrochloric acid and sulfuric acid;
the active component B is selected from one or more of pyraclostrobin B1, enestroburin B2, azoxystrobin B3, isopyrazam B4, fluxapyroxad hydroxylamine B5, fluazinam B6, trifloxystrobin B7, fluxapyroxad B9, fluopyram B10, thifluzamide B14, benzovindiflupyr B15, pyriproxam B19, pyrapoyne B22, boscalid B33, fenpicoxamid B44, florylpicoxamid B45, metarylpicoxamid B46 and zoxamide B47;
the weight ratio of the A, B active components is 1:4-4:1.
Use of a fungicidal composition for the preparation of a medicament for controlling phytopathogenic fungal diseases.
The plant pathogenic fungus disease is plant powdery mildew, anthracnose, leaf spot, downy mildew, black pox, white rot, epidemic disease, cladosporium cucumerinum, rust, scab, leaf mold, gray mold, clubroot, black nevus, rice blast, banded sclerotial blight, sclerotial blight or damping off.
The composition of the present invention is used at a concentration of 5 to 500mg/L (active ingredient content, the same applies hereinafter) in the crop planting area, preferably 50 to 200mg/L, depending on the occurrence degree of crop diseases.
The composition of the invention comprises an active component A and at least one active component B which are prepared in advance or prepared on the site of use according to the proper proportion provided by the invention or the two components are used separately and sequentially.
The composition is suitable for the prevention and treatment of fungi diseases of trees (apples, rubber, pears, oranges, haws, chinese chestnut, peppers, medlar, mangoes, papaya and the like), vines (grapes), melons (tomatoes, eggplants, peppers, cucumbers, melons, white melons, watermelons, pumpkins, balsam pears, luffa, chayote, cucurbits, zucchini, carrots, lettuce, potatoes, cabbages and rape), beans (soybeans, peas, kidney beans and cowpeas), cereals (wheat, rice and corn), shallots and garlic (onions, garlic and onion), flowers and lawns, seed treatment, fruit preservation and the like.
The fungicidal compositions according to the invention are particularly suitable for controlling the following plant diseases: apple tree powdery mildew, apple tree rust, apple brown spot, rubber tree powdery mildew, pear rust, citrus powdery mildew, hawthorn powdery mildew, chestnut powdery mildew, prickly ash powdery mildew, medlar powdery mildew, mango powdery mildew, papaya powdery mildew, rod powdery mildew, grape black spot, and white rot of grape, powdery mildew of tomato, powdery mildew of eggplant, powdery mildew of capsicum, powdery mildew of cucumber, powdery mildew of melon, powdery mildew of white gourd, powdery mildew of watermelon, powdery mildew of pumpkin, powdery mildew of bitter gourd, powdery mildew of luffa, powdery mildew of chayote, powdery mildew of cucurbit, powdery mildew of zucchini, powdery mildew of melon, gummy stem blight of cucumber, powdery mildew of melon, powdery mildew of white gourd, powdery mildew of watermelon, powdery mildew of pumpkin, powdery mildew of bitter gourd, powdery mildew of luffa, powdery mildew of chayote, powdery mildew of pumpkin carrot powdery mildew, lettuce powdery mildew, soybean rust, pea powdery mildew, kidney bean rust, kidney bean powdery mildew, cowpea rust, melon anthracnose, melon brown spot, potato black nevus, potato late blight, capsicum epidemic, celery cabbage clubroot, rape sclerotium disease, wheat rust, wheat sheath blight, wheat powdery mildew, wheat scab, rice sheath blight, corn rust, onion rust, garlic rust, onion rust, rose powdery mildew, chrysanthemum powdery mildew, turf grass rust black nevus, damping off of various potato plants, and the like.
The invention has the advantages that
The invention combines the active component A and the active component B according to different proportions, effectively improves the disease control effect, has obvious synergistic effect, and can delay the generation of drug resistance of pathogenic bacteria and prolong the service life of the medicament by combining the active component A and the active component B according to specific proportions.
Detailed Description
The synergistic effect of the compositions of the present invention on harmful fungi is further illustrated by the following examples, but the invention is by no means limited thereto. Wherein the active components are the active component A and the respiration inhibitor bactericide B in the fungicidal composition; and the preparation of the active component A is described in patent CN 102336744B.
The test method and the evaluation method are as follows:
the active samples to be tested are respectively an active component A, an active component B, and a composition of the active component A and the active component B.
The active component A is an active component A1 or an active component A2.
The active component A is a compound A1 shown in a general formula I (taking the compound as an example):
Figure BDA0003436289560000061
in the general formula:
q is selected from Q2 shown below:
Figure BDA0003436289560000062
w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; n=0; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3 O); namely, the compound A1.
The active component A2 is a salt formed by the compound A1 and sulfuric acid;
the active components B are pyraclostrobin B1, enestroburin B2, azoxystrobin B3, fluxapyroxad hydroxylamine B5, trifloxystrobin B7, thifluzamide B14 and benzovindiflupyr B15.
The composition to be tested is a composition composed of an active component A1, pyraclostrobin B1, enestroburin B2, azoxystrobin B3, fluxapyroxad hydroxylamine B5, trifloxystrobin B7, thifluzamide B14 and benzovindiflupyr B15; or a composition consisting of an active component A2, pyraclostrobin B1, enestroburin B2, azoxystrobin B3, fluxapyroxad hydroxylamine B5, trifloxystrobin B7, thifluzamide B14 and benzovindiflupyr B15.
The specific mode is as follows:
dissolving the above active components or compositions with acetone or water (the volume ratio of acetone to spray amount is equal to or less than 0.05), diluting with water containing 0.1% Tween 80, and preparing into desired concentration solution to be tested, and mixing the solutions to be tested according to a set proportion. And spraying the liquid to be detected on the disease host plants on a crop sprayer, and inoculating the disease after 24 hours. According to the disease characteristics, the disease plants which need to be subjected to temperature control and moisture preservation culture are inoculated and then placed in a climatic chamber for culture, and after the infection of the disease is completed, the plants are transferred into a greenhouse for culture. After the control is sufficiently ill, the percentage of leaf area of the pathogen-infected crop is determined and calculated using the Abbot formula to obtain the observed efficacy (W):
W＝(1-α/β)×100
wherein:
alpha: percent fungal infestation of the treated crop;
beta: percent fungal infestation of untreated (control) crops;
efficacy of "0" means that the level of infestation of the treated crop is the same as the level of infestation of the untreated control crop; efficacy of "100" means that the treated crop was not infested.
The expected efficacy (calculated efficacy) of the composition was determined using the Colby formula (see r.s. Colby, weeds, 1967, 15, 20-22) and compared to the observed efficacy.
E＝X+Y–XY/100
Wherein:
e: the expected efficacy (calculated efficacy in the tables below) when using the compositions of active components a and B at concentrations a and B, expressed as% of untreated control;
x: efficacy of active ingredient a at a concentration a was used, expressed as% of untreated control;
y: the efficacy of active ingredient B at a concentration B was used, expressed as% of untreated control.
When the observed efficacy value is greater than the calculated efficacy value, the composition is indicated to have a synergistic effect; when the observed efficacy value is equal to the calculated efficacy value, the composition is indicated to be additive; when the observed efficacy value is less than the calculated efficacy value, the composition is indicated to be antagonistic.
Example 1 test for controlling powdery mildew of wheat
The seedling of wheat in the two-leaf stage of pot plant of Liaochun 15 is sprayed with water solution of each active component or composition, the concentration of the active component is shown in the following table, and after 24 hr, wheat powdery mildew spores are shaken off on wheat leaves and cultured in a greenhouse for 7 days, and the development degree of germ infection on the leaves is measured.
The activity data of each individual active component and the composition of the invention for preventing and treating wheat powdery mildew are shown in tables 1 and 2.
The results show that the observed efficacy values of the compositions are all greater than the calculated efficacy values, and that the compositions exhibit a synergistic effect over the range of the tested formulation.
TABLE 1 Activity of the individual active ingredients
Figure BDA0003436289560000071
Figure BDA0003436289560000081
TABLE 2 Activity of the compositions of the invention
Figure BDA0003436289560000082
Figure BDA0003436289560000091
Example 2 test for controlling wheat rust
The potted two-leaf wheat seedlings of the variety Liaochun 15 were sprayed with an aqueous solution of each active ingredient or composition (the concentrations of the active ingredients are shown in the following table), inoculated with a wheat rust spore suspension after 24 hours, and cultured in a greenhouse for 7 days, and the extent of development of pathogen infection on the leaves was determined.
The activity data of each individual active ingredient and the composition of the invention for controlling wheat rust are shown in tables 3 and 4.
The results show that the observed efficacy values of the compositions are all greater than the calculated efficacy values, and that the compositions exhibit a synergistic effect over the range of the tested formulation.
TABLE 3 Activity of the individual active ingredients
Figure BDA0003436289560000092
Figure BDA0003436289560000101
TABLE 4 Activity of the compositions of the invention
Figure BDA0003436289560000102
EXAMPLE 3 test for controlling soybean rust
Potted soybean seedlings (variety: liao beans 10) which grow well and consistently are selected, 2 true leaves are cut off from the growing points, the leaves are sprayed with an aqueous solution of each active ingredient or composition (the concentrations are described in the following table), after 24 hours, soybean rust spore suspensions are inoculated on soybean leaves and cultured in a greenhouse, and the extent of development of pathogen infestation on the leaves is determined after 15 days.
The activity data for each individual active ingredient and the compositions of the present invention for controlling soybean rust are shown in tables 5 and 6.
The results show that the observed efficacy values of the compositions are all greater than the calculated efficacy values, and that the compositions exhibit a synergistic effect over the range of the tested formulation.
TABLE 5 Activity of the individual active ingredients
Figure BDA0003436289560000111
TABLE 6 Activity of the compositions of the invention
Figure BDA0003436289560000112
/>
Figure BDA0003436289560000121
Example 4 test for controlling powdery mildew of Capsici fructus
Pepper seedlings of the variety "Hangzhou pepper No. one" were sprayed with aqueous solutions of the respective active ingredients or compositions (concentrations as described in the following table), 24 hours later, pepper powdery mildew spore suspensions were inoculated on pepper leaves, cultured in a greenhouse, and after 15 days, the extent of development of pathogen infection on the leaves was determined.
The activity data of each individual active ingredient and the composition of the invention for controlling powdery mildew of capsicum are shown in tables 7 and 8.
The results show that the observed efficacy values of the compositions are all greater than the calculated efficacy values, and that the compositions exhibit a synergistic effect over the range of the tested formulation.
TABLE 7 Activity of the individual active ingredients
Figure BDA0003436289560000122
TABLE 8 Activity of the compositions of the invention
Figure BDA0003436289560000131
Example 5 test for controlling wheat scab
Potted corn seedlings (variety: golden glutinous) which grow neatly and consistently are selected, sprayed with an aqueous solution (concentrations of each active ingredient or composition are as described in the following table), inoculated with a scab spore suspension after 24 hours, and cultured in a climatic chamber for 4 days, and the extent of development of pathogen infestation on the leaves is determined.
The results of the activity data for the control of wheat scab for each individual active ingredient and the compositions of the invention are shown in tables 9 and 10.
The results show that the observed efficacy values of the compositions are all greater than the calculated efficacy values, and that the compositions exhibit a synergistic effect over the range of the tested formulation.
TABLE 9 Activity of the individual active ingredients
Figure BDA0003436289560000141
TABLE 10 Activity of the compositions of the invention
Figure BDA0003436289560000142
/>
Figure BDA0003436289560000151
Example 6 test for controlling sheath blight of rice
Selecting rice potted seedlings (variety: liaoxing No. 2) which grow neatly and consistently, spraying with aqueous solutions of each active component or composition (the concentrations are shown in the following table), inoculating for 24 hours by a method of inoculating by a fungus block method, inoculating to the base of the rice seedlings, culturing in a greenhouse, and measuring the development degree of pathogen infection on leaf sheaths after 5 days.
The results of the activity data for controlling rice sheath blight disease of each individual active ingredient and the composition of the present invention are shown in tables 11 and 12.
The results show that the observed efficacy values of the compositions are all greater than the calculated efficacy values, and that the compositions exhibit a synergistic effect over the range of the tested formulation.
TABLE 11 Activity of the individual active ingredients
Figure BDA0003436289560000152
/>
Figure BDA0003436289560000161
TABLE 12 Activity of the compositions of the invention
Figure BDA0003436289560000162
/>
Figure BDA0003436289560000171
/>

Claims (7)

1. A fungicidal composition comprising a substituted triazolinone ether compound, characterized in that: the composition comprises A, B two active components, wherein the weight ratio of the active component A to the active component B is 1:99-99:1;
the active component A is a compound shown in a general formula I or a salt thereof;
Figure FDA0003436289550000011
in the general formula:
q is selected from Q1 or Q2 as shown below:
Figure FDA0003436289550000012
w is selected from O;
R 1 selected from methyl;
when Q is selected from Q1: r is R 2 Selected from hydrogen, halogen, cyano, nitro, CH 2 CN, C1-C6 alkaneA radical, a halogenated C1-C6 alkyl radical or a C3-C6 cycloalkyl radical, R 3 Selected from hydrogen, C1-C6 alkyl or halogenated C1-C6 alkyl;
when Q is selected from Q2: r is R 2 Selected from halogen, C1-C6 alkyl, halogenated C1-C6 alkyl or C3-C6 cycloalkyl, R 3 Selected from C1-C6 alkyl or halogenated C1-C6 alkyl;
R 4 selected from halogen, cyano, nitro, hydroxy, C1-C4 alkyl, halo C1-C3 alkyl, C1-C3 alkoxy, halo C1-C3 alkoxy, C1-C3 alkylthio, C1-C3 alkylsulfonyl, phenyl or phenoxy, unsubstituted or substituted with 1 to 5 groups independently selected from chloro, bromo, fluoro, nitro, cyano, trifluoromethyl, C1-C3 alkyl, C1-C3 alkoxy or halo C1-C3 alkoxy; n=0-5;
R 5 、R 6 can be identical or different and is selected from hydrogen, halogen, nitro, cyano, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, phenyl, pyridyl, furyl, thienyl or thiazolyl, which are unsubstituted or substituted by 1 to 5 radicals independently selected from halogen, cyano, nitro, CO 2 (C1-C4 alkyl), C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio or C1-C6 alkylsulfonyl;
y is selected from halogen, OR 7 、SR 7 、SOR 7 、SO 2 R 7 Or NHR 7 The method comprises the steps of carrying out a first treatment on the surface of the Wherein R is 7 Selected from hydrogen or C1-C4 alkyl;
the active component B is selected from pyraclostrobin B1, enestroburin B2, azoxystrobin B3, isopyrazam B4, fluxapyroxad hydroxylamine B5, fluazinam B6, trifloxystrobin B7, cyazofamid B8, fluxapyroxad B9, fluopyram B10, fluoroether mycoamide B11, fluorophenylamide B12, fluoroamide B13, thifluzamide B14, benzovindiflupyr B15, penflufen B16, fluxapyroxad B17, ipratropium B18, inpyrfluxam B19, isoflucypram B20, pyraziflumid B21, pyrafungone B22, carboxin B23, fenhexamid B12, fenhexamid B17, penflufen B18, iprovalicarb and pyriproxil B22 one or more of carboxin B24, furbenomyl B25, fenhexamid B26, meflofen B27, silthiopham B28, enestroburin 29, pyraclostrobin 30, pyraclostrobin 31, cyproconazole B32, boscalid B33, bixafen B34, picoxystrobin 35, kresoxim-methyl 36, fluoxastrobin B37, coumoxystrobin B38, kresoxim-methyl B39, chlorpyriproxyfen B40, phenoxypenoxsulam B41, trifloxystrobin B42, benthiavalicarb 43, fenpiclamid B44, florylpicoxamid B45, metarylpicoxamid B, zoxamide B47, pyribenzoxim B48 and penthiopyrad B49.
2. A fungicidal composition according to claim 1, characterized in that: the active component A is selected from compounds shown in a general formula I or salts thereof;
in the general formula:
q is selected from Q1 or Q2 as shown below:
w is selected from O;
R 1 selected from methyl;
when Q is selected from Q1: r is R 2 Selected from hydrogen, fluorine, chlorine, bromine or C1-C4 alkyl, R 3 Selected from hydrogen or C1-C6 alkyl;
when Q is selected from Q2: r is R 2 Selected from C1-C4 alkyl, R 3 Selected from C1-C6 alkyl;
R 4 selected from halogen, cyano, nitro, C1-C4 alkyl, halogenated C1-C3 alkyl, C1-C3 alkoxy, halogenated C1-C3 alkoxy or C1-C3 alkylsulfonyl;
n＝0-3；
R 5 、R 6 which may be the same or different, are each selected from hydrogen, chlorine, bromine, fluorine, nitro, cyano, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy or halogenated C1-C4 alkoxy;
y is selected from Cl, OR 7 Or SR (S.J) 7 The method comprises the steps of carrying out a first treatment on the surface of the Wherein R is 7 Selected from C1-C4 alkyl;
the salt of the compound shown in the general formula I is the salt formed by the compound shown in the general formula I and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid and fumaric acid;
the active component B is selected from pyraclostrobin B1, enestroburin B2, azoxystrobin B3, isopyrazam B4, fluoxastrobin B5, fluoxastrobin B6, trifloxystrobin B7, cyazofamid B8, fluoxastrobin B9, fluopyram B10, fluoxastrobin B11, fluoxastrobin B12, thifluzamide B14, benzovindiflupyr B15, penflufen B16, ipratropium B18, inpyrfluxam B19, isoflucypram B20, pyraziflumid B21, pyrapoyne B22, enestroburin 29, pyraclostrobin 30, pyraclostrobin 31, boscalid B33, bixafen B34, picoxystrobin 35, kresoximide 36, fluoxastrobin B37, coumoxystrobin B38, kresoxim B39, chloromycetin B40, zoxamide B41, zoxamide B42, penciclovir 35, penciclovir B45, penoxsulam 35, penoxsulam 45;
A. the weight ratio of the two active components is 1:50-50:1.
3. A fungicidal composition according to claim 2, characterized in that: the active component A is selected from compounds shown in a general formula I or salts thereof;
in the general formula:
q is selected from Q1 or Q2;
w is selected from O;
R 1 selected from methyl;
when Q is selected from Q1: r is R 2 Selected from hydrogen or methyl, R 3 Selected from hydrogen, methyl or ethyl;
when Q is selected from Q2: r is R 2 Selected from methyl, R 3 Selected from methyl;
R 4 selected from halogen, cyano, nitro, methyl, ethyl, isopropyl, t-butyl, CF 3 、CH 3 O or CF 3 O；
n＝0-3；
R 5 、R 6 May be the same or different and are each selected from hydrogen, chlorine, bromine, fluorine or C1-C4 alkyl;
y is selected from Cl, CH 3 O or CH 3 S；
The salt of the compound shown in the general formula I is the salt formed by the compound shown in the general formula I and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid and benzoic acid;
the active component B is selected from one or more of pyraclostrobin B1, enestroburin B2, azoxystrobin B3, isopyrazam B4, fluoxastrobin B5, fluoxastrobin B6, trifloxystrobin B7, cyazofamid B8, fluoxastrobin B9, fluopyram B10, thifluzamide B14, benzovindiflupyr B15, iprfluxam B19, isoflucypram B20, pyraziflumid B21, pyrapoyne B22, enestroburin 29, pyraclostrobin 30, pyraclostrobin 31, boscalid B33, picoxystrobin 35, kresoxim 36, fluoxastrobin B37, coumoxystrobin B38, fluoxastrobin B40, fenpyraclostrobin B41, fenpiclamid B44, florylpicoxamid B, metarylpicoxamid B, zoxaprop B47 and pyrimethanil B49;
the weight ratio of the A, B active components is 1:20-20:1.
4. A fungicidal composition according to claim 2, characterized in that: the active component A is selected from compounds shown in a general formula I or salts thereof;
in the general formula:
q is selected from Q2;
w is selected from O;
R 1 selected from methyl;
R 2 selected from methyl, R 3 Selected from methyl;
R 4 selected from fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, CF 3 、CH 3 O or CF 3 O；
n=0, 1, 2 or 3;
R 5 、R 6 may be the same or different and are each selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl or isopropyl;
y is selected from Cl or CH 3 O；
The salt of the compound shown in the general formula I is a salt formed by the compound shown in the general formula I and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid and acetic acid;
the active component B is selected from one or more of pyraclostrobin B1, enestroburin B2, azoxystrobin B3, isopyrazam B4, fluxapyroxad hydroxylamine B5, fluazinam B6, trifloxystrobin B7, fluxapyroxad B9, fluopyram B10, thifluzamide B14, benzovindiflupyr B15, ippyrfluxam B19, isoflucypram B20, pyraziflumid B21, pyrapoyne B22, pyraclostrobin 31, boscalid B33, picoxystrobin 35, coumoxystrobin B38, fenpicloramid B44, florylpicoxamid B, metarylpicoxamid B, zoxamide B47 and pyrithiobacmid B49;
the weight ratio of the A, B active components is 1:10-10:1.
5. The fungicidal composition of claim 4, wherein: the active component A is selected from compounds shown in a general formula I or salts thereof;
in the general formula:
q is selected from Q2; w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; n=0; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3O);
or Q is selected from Q2; w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; r is R 4 Selected from fluorine; n=1; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3 O)；
Or Q is selected from Q2; w is selected from O; r is R 1 Selected from methyl; r is R 2 Selected from methyl, R 3 Selected from methyl; r is R 4 Selected from chlorine; n=1; r is R 5 、R 6 Are all selected from hydrogen; y is selected from CH 3 O)；
The salt of the compound shown in the general formula I is a salt formed by the compound shown in the general formula I, hydrochloric acid and sulfuric acid;
the active component B is selected from one or more of pyraclostrobin B1, enestroburin B2, azoxystrobin B3, isopyrazam B4, fluxapyroxad hydroxylamine B5, fluazinam B6, trifloxystrobin B7, fluxapyroxad B9, fluopyram B10, thifluzamide B14, benzovindiflupyr B15, pyriproxam B19, pyrapoyne B22, boscalid B33, fenpicoxamid B44, florylpicoxamid B45, metarylpicoxamid B46 and zoxamide B47;
the weight ratio of the A, B active components is 1:4-4:1.
6. Use of a fungicidal composition characterized in that: the fungicidal composition is used for preparing medicines for preventing and treating plant pathogenic fungi diseases.
7. The use of a fungicidal composition according to claim 6, wherein: the plant pathogenic fungus disease is plant powdery mildew, anthracnose, leaf spot, downy mildew, black pox, white rot, epidemic disease, cladosporium cucumerinum, rust, scab, leaf mold, gray mold, clubroot, black nevus, rice blast, banded sclerotial blight, sclerotial blight or damping off.
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CN102336743A (en) * 2010-07-20 2012-02-01 中国中化股份有限公司 Triazoline ketone ether-substituted compound and application thereof
WO2018202737A1 (en) * 2017-05-05 2018-11-08 Basf Se Fungicidal mixtures comprising triazole compounds
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Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999011129A1 (en) * 1997-09-04 1999-03-11 E.I. Du Pont De Nemours And Company Enantiomerically enriched compositions and their pesticidal use
WO1999033812A1 (en) * 1997-12-29 1999-07-08 Aventis Cropscience S.A. 3-(5)-benzyloxypyrazole useful as fungicides
CN102336744A (en) * 2010-07-20 2012-02-01 中国中化股份有限公司 Substituted triazoline ether ketone class compound and application thereof as bactericide as well as insecticide and acaricide
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