CN111316992A - Fungicidal composition and application thereof - Google Patents
Fungicidal composition and application thereof Download PDFInfo
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- CN111316992A CN111316992A CN201811531838.8A CN201811531838A CN111316992A CN 111316992 A CN111316992 A CN 111316992A CN 201811531838 A CN201811531838 A CN 201811531838A CN 111316992 A CN111316992 A CN 111316992A
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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
- A01N43/48—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
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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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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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
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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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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Abstract
The invention belongs to the field of agricultural bactericides, and particularly 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-1F and salts thereof, and the active component B is selected from triazole bactericides. The fungicidal compositions according to the invention are particularly suitable for controlling a variety of phytopathogenic fungal diseases, such as powdery mildew, scab, rust, leaf mold, sheath blight or damping off.
Description
Technical Field
The invention belongs to the field of agricultural bactericides, and particularly relates to a pyrimidine-containing fungicidal composition containing a substituted pyrazole compound and a triazole bactericide and application thereof.
Background
WO2016184378 discloses a pyrimidine-containing substituted pyrazole compound and its use, wherein the compound shown in the following general formula I-1F is reported to have good activity on various fungal diseases.
The usage history of the bactericide shows that the same type of medicament is repeatedly used for a long time, so that part of strains of diseases easily generate medicament resistance, and the medicament effect is obviously reduced.
Disclosure of Invention
The invention aims to provide a pyrimidine-containing fungicidal composition of a substituted pyrazole compound and a triazole fungicide and application thereof, so as to delay the generation of drug resistance of pathogenic bacteria and prolong the service life of a medicament.
In order to achieve the purpose, the invention adopts the following technical scheme:
a fungicidal composition comprises 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 as a general formula I-1F or a salt thereof.
In the formula:
R3selected from hydrogen, hydroxy, formyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylthio radical, C2-C4Alkenylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkenyl, halo C2-C4Alkynyl, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkylsulfinyl, halogeno C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylaminosulfonyl, di (C)1-C4Alkyl) aminosulfonyl, C1-C4Alkylsulfonylaminocarbonyl group, C1-C4Alkylcarbonylaminosulfonyl radical, C3-C4Cycloalkyloxycarbonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkyl carbonyl radical C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylaminocarbonyl, di (C)1-C4Alkyl) aminocarbonyl, C2-C4Alkenyloxycarbonyl radicalBase, C2-C4Alkynyloxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkoxycarbonyl group, C1-C4Alkylaminosulfenyl, di (C)1-C4Alkyl) aminosulfanyl, (hetero) arylcarbonyl C which is unsubstituted or further substituted by 1 to 51-C4Alkyl, (hetero) arylcarbonyl, (hetero) aryloxycarbonyl, (hetero) aryl C1-C4Alkyloxycarbonyl, (hetero) aryl C1-C4Alkyl, halogen, nitro, cyano;
R4、R5can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group; wherein R is4、R5C attached thereto may also form C3-C4A ring of (a);
R6、R7can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group; wherein R is6、R7C attached thereto may also form C3-C4A ring of (a);
R8、R9can be the same or different and are respectively selected from hydrogen, cyano, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted (hetero) aryl, (hetero) arylmethyl, (hetero) arylcarbonyl, (hetero) arylmethylcarbonyl or (hetero) aryloxycarbonyl;
R11selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C1-C4Alkylthio, halo C1-C4Alkylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, C2-C4Alkenyloxy, halogeno C2-C4Alkenyloxy radical, C2-C4Alkynyloxy, halo C2-C4Alkynyloxy, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxycarbonyloxy, halo C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group; n is an integer of 0 to 5, and when n is 0, no substituent is arranged on a benzene ring; when n is greater than 1, R11May be the same or different;
R14、R15、R16or R17Can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy or C3-C4A cycloalkyl group;
w is selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkoxy radical, C1-C4Alkylthio or C1-C4An alkylsulfonyl group;
the active component B is selected from one or more of triazole bactericides.
The active component A is a salt of a compound shown as a general formula I-1F, wherein the salt of the compound shown as the general formula I-1F is a salt formed by the compound shown as the general formula I-1F 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, fumaric acid, sorbic acid, malic acid or citric acid.
According to the invention, the weight ratio of A, B to 50:1 is 1: 50-50;
the active component A is a compound shown as a general formula I-1F or a salt thereof;
in the general formula R3Selected from hydrogen, hydroxy, formyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylthio radical, C2-C4Alkenylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkenyl or halogeno C2-C4An alkynyl group;
R4、R5can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
R6、R7can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
R8、R9can be the same or different and are respectively selected from hydrogen, cyano, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl or halo C1-C4An alkoxycarbonyl group;
R11selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylamino or halogeno C1-C4An alkylamino group; n is an integer of 0 to 5, and when n is greater than 1, R11May be the same or different;
R14、R15、R16or R17Can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
w is selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkoxy or C1-C4An alkylthio group;
the active component B is selected from one or more of tebuconazole B1, propiconazole B2, difenoconazole B3, epoxiconazole B4, triadimefon B5, flusilazole B6, high-efficiency diniconazole B7, myclobutanil B8, diniconazole B9, penconazole B10, hexaconazole B11, triadimenol B12, cyproconazole B13, fluquinconazole B14, flutriafol B15, metconazole B16, imibenconazole B17, prothioconazole B18, ipconazole B19, triticonazole B20, bitertazol B21, epoxiconazole B22, tetraconazole B23, imazalil B24, high-efficiency imazalil B25, tetraconazole 26 or metconazole 28.
The active component A is a salt of a compound shown in a general formula I-1F, wherein the salt of the compound shown in the general formula I-1F is a salt formed by the compound shown in the general formula I-1F and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid or maleic acid.
Further preferred according to the invention, the weight ratio of A, B two active ingredients in the composition is 1:20-20: 1;
the active component A is a compound in a general formula I-1F or a salt thereof;
in the general formula R3Selected from hydrogen, hydroxy, formyl, C1-C4Alkyl or halo C1-C4An alkyl group; r4、R5Can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl or halo C1-C4An alkyl group; r6、R7Can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl or halo C1-C4An alkyl group; r8、R9Can be the same or different and are respectively selected from hydrogen, cyano, halogen and C1-C4Alkyl or halo C1-C4An alkyl group; r11Selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl or halo C1-C4An alkyl group; n is an integer of 0 to 5, and when n is greater than 1, R11May be the same or different; r14、R15、R16Or R17Can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl or halo C1-C4An alkyl group; w is selected from hydrogen, halogen, C1-C4Alkyl or halo C1-C4An alkyl group;
the active component B is selected from one or more of tebuconazole B1, propiconazole B2, difenoconazole B3, epoxiconazole B4, triadimefon B5, flusilazole B6, diniconazole B7, myclobutanil B8, hexaconazole B11, cyproconazole B13, flutriafol B15, imibenconazole B17, prothioconazole B18, triticonazole B20, bitertanol B21 or tetraconazole B23.
The active component A is a salt of a compound shown in a general formula I-1F, wherein the salt of the compound shown in the general formula I-1F is a salt formed by the compound shown in the general formula I-1F and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid or methanesulfonic acid.
Still further preferred in the present invention, the composition is A, B, the weight ratio of the two active components is 1:10-10: 1;
the active component A is a compound shown as a general formula I-1F or a salt thereof, wherein R in the general formula3Selected from hydrogen, hydroxy, formyl or C1-C4An alkyl group; r4、R5Can be the same or different and are respectively selected from hydrogen, halogen or C1-C4An alkyl group; r6、R7Can be the same or different and are respectively selected from hydrogen, halogen or C1-C4An alkyl group; r8、R9Can be the same or different and are respectively selected from hydrogen, cyano, halogen or C1-C4An alkyl group; r11Selected from halogen, hydroxy, amino, cyano, nitro or C1-C4An alkyl group; n is an integer of 0 to 5, and when n is greater than 1, R11May be the same or different; r14、R15、R16Or R17Can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro or C1-C4An alkyl group; w is selected from hydrogen, halogen or C1-C4An alkyl group;
the active component B is selected from one or more of tebuconazole B1, propiconazole B2, difenoconazole B3, epoxiconazole B4, triadimefon B5, flusilazole B6, myclobutanil B8, hexaconazole B11, cyproconazole B13, flutriafol B15, imibenconazole B17, prothioconazole B18 or tetraconazole B23.
The active component A is a salt of a compound shown in a general formula I-1F, wherein the salt of the compound shown in the general formula I-1F is a salt formed by the compound shown in the general formula I-1F and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid or acetic acid.
Even more preferably, the composition is A, B, the weight ratio of the two active components is 1:5-5: 1;
the active component A is a compound shown as a general formula I-1F or a salt thereof, wherein R in the general formula3Selected from hydrogen, R4、R5Are each selected from hydrogen, R6、R7Are each selected from hydrogen, R8、R9Are each selected from hydrogen, R11Selected from 4-chloro, R14、R15、R16Or R17Are respectively selected from hydrogen, and W is selected from hydrogen.
The active component B is selected from one or more of tebuconazole B1, propiconazole B2, difenoconazole B3, epoxiconazole B4, triadimefon B5, flusilazole B6, myclobutanil B8, prothioconazole B18 or tetraconazole B23.
The active component A is a salt of a compound shown in a general formula I-1F, wherein the salt of the compound shown in the general formula I-1F is a salt formed by the compound shown in the general formula I-1F and sulfuric acid.
Use of a fungicidal composition for the preparation of a medicament for the control of phytopathogenic fungal diseases.
The plant pathogenic fungus diseases are plant powdery mildew, scab, rust disease, leaf mold, banded sclerotial blight, black nevus, ring spot, alternaria leaf spot or damping off.
The active ingredient of the preparation of the sterilization preparation is the fungicidal composition, and the weight percentage of the fungicidal composition is 0.1-95%.
The composition of the present invention is used at a concentration of 5 to 500mg/L (content of active ingredient, the same shall apply hereinafter) in the area where crops are grown, preferably 50 to 200mg/L, depending on the degree of occurrence of crop diseases.
The active component A and at least one active component B in the composition are prepared in advance or prepared on the site of use or the two components are separately and sequentially used according to a proper proportion provided by the invention.
The composition is suitable for application in prevention and control of fungal diseases of trees (apples, rubber, pears, oranges, hawthorns, chestnuts, peppers, medlar, mangoes, papayas and the like), vines (grapes), melons (tomatoes, eggplants, hot peppers, cucumbers, melons, white gourds, watermelons, pumpkins, balsam pears, luffa, chayords, cucurbits, pumpkin, carrots, lettuce, potatoes), beans (soybeans, peas, kidney beans, cowpeas), cereals (wheat, rice, corns), onions and garlics (shallots, garlic, onions), flowering plants 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 powdery mildew, apple tree rust, rubber powdery mildew, pear rust, citrus powdery mildew, hawthorn powdery mildew, Chinese chestnut powdery mildew, pepper powdery mildew, medlar powdery mildew, mango powdery mildew, papaya powdery mildew, grape powdery mildew, tomato powdery mildew, eggplant powdery mildew, hot pepper powdery mildew, cucumber powdery mildew, melon powdery mildew, wax gourd powdery mildew, watermelon powdery mildew, pumpkin powdery mildew, balsam pear powdery mildew, towel gourd powdery mildew, chayote powdery mildew, cucurbit powdery mildew, pumpkin powdery mildew, carrot powdery mildew, lettuce powdery mildew, soybean rust, pea powdery mildew, kidney bean rust, kidney bean powdery mildew, cowpea rust, potato black rust, wheat grain, wheat powdery mildew, rice grain, corn rust, onion rust, monthly powdery mildew, Chinese rose powdery mildew, Chinese flowering cabbage, tomato powdery mildew, tomato, Rose powdery mildew, chrysanthemum powdery mildew, turfgrass rust and the like.
The invention has the advantages of
According to the invention, the active component A and the bactericide active component B are combined according to different proportions, so that the disease control effect is effectively improved. After scientific calculation by adopting a professional formula, the observation effect values of the experimental mixture ratios of the composition are far higher than the calculation effect values, and the synergistic effect is very obvious.
Detailed Description
The synergistic effect of the compositions according to the invention on harmful fungi is further illustrated by the following examples, to which, however, the invention is in no way restricted. Wherein the active components are the active component A and the triazole fungicide B in the antifungal composition; and the preparation of active component A is described in WO 2016184378.
The test method and the evaluation method are as follows:
the active samples to be detected are respectively active component A, active component B, and the composition of active component A and active component B.
The active component A is active component A1 or active component A2.
The active component A is a compound A1 shown in a general formula I-1F:
in the formula:
R3selected from hydrogen, R4、R5Are respectively selected from hydrogen R6、R7Are each selected from hydrogen, R8、R9Are each selected from hydrogen, R11Selected from 4-chloro, R14、R15、R16Or R17Are respectively selected from hydrogen, W is selected from hydrogen, namely the compound A1;
the active component A2 is a salt of compound A1 with sulfuric acid.
The active component B is tebuconazole B1, propiconazole B2, difenoconazole B3, epoxiconazole B4, triadimefon B5, flusilazole B6, myclobutanil B8, prothioconazole B18 or tetraconazole B23.
The composition to be tested is a composition consisting of an active component A1, tebuconazole B1 or propiconazole B2, difenoconazole B3, epoxiconazole B4, triazolone B5, flusilazole B6, myclobutanil B8, prothioconazole B18 and tetraconazole B23 respectively; or a composition consisting of the active component A2 and tebuconazole B1 or propiconazole B2, difenoconazole B3, epoxiconazole B4, triadimefon B5, flusilazole B6, myclobutanil B8, prothioconazole B18 or tetraconazole B23.
The specific mode is as follows:
dissolving the above active components or compositions in acetone or water (volume ratio of acetone amount to liquid spray amount is equal to or less than 0.05), diluting with water containing 0.1% Tween 80 to obtain solution to be tested with desired concentration, and preparing the solution to be tested according to a set proportion. Spraying the solution to be detected on the disease host plants on a crop sprayer, and inoculating diseases after 24 hours. According to the characteristics of diseases, plant diseases needing temperature and moisture control culture are inoculated and then cultured in a climate chamber, and after the diseases are infected, the plants are transferred into a greenhouse for culture. After the contrast is sufficiently diseased, determining the percentage of the area of the leaves of the pathogen infected with the crops, and calculating by using an Abbot formula to obtain the observation effect (W):
W＝(1-α/β)×100
in the formula:
α percent fungal infestation of treated crops;
β percent fungal infestation of untreated (blank) crops;
an efficacy of "0" indicates that the level of infestation of the treated crop is the same as the level of infestation of the untreated control crop; an efficacy of "100" indicates that the treated crop is not infested.
The expected efficacy (calculated efficacy) of the composition was determined using the Colby formula (see r.s. Colby, Weeds (Weeds), 1967, 15, 20-22) and compared to the observed efficacy.
E＝X+Y–XY/100
In the formula:
e: the expected efficacy (calculated efficacy in the tables below) when using the combination of active components a and B at concentrations a and B, expressed as% of the untreated control;
x: the efficacy of active ingredient a at the concentration a used, expressed as% of the untreated control;
y: the efficacy of active ingredient B at the concentration B used is expressed as% of the untreated control.
When the observed efficacy value is greater than the calculated efficacy value, the composition is shown to have a synergistic effect; when the observed efficacy value is equal to the calculated efficacy value, indicating that the composition is additive; when the observed potency value is less than the calculated potency value, the composition is indicated as antagonistic.
EXAMPLE 1 wheat powdery mildew control test
The method comprises the following steps of spraying aqueous solutions (effective component concentrations are shown in the table below) of active components or compositions on two-leaf stage wheat seedlings cultivated in pots of Liaochun 15, shaking off wheat powdery mildew spores on wheat leaves after 24 hours, culturing in a greenhouse, and measuring the development degree of germ infection on the leaves after 7 days.
The data on the activity of the individual active ingredients and the compositions according to the invention for controlling wheat powdery mildew are shown in tables 1 and 2.
TABLE 1 Activity of the Individual active ingredients
TABLE 2 Activity of the compositions of the invention
The results show that the observed efficacy values of the compositions are all larger than the calculated efficacy values, and the compositions show synergistic effect within the range of the experimental mixture ratio.
Example 2 test for controlling cucumber powdery mildew
The cucumber seedlings in the two-leaf period of the potted plant of the variety 'Xintai Mici' are treated by spraying with aqueous solutions (the concentration is shown in the table below) of the active components or the compositions, after 24 hours, the cucumber powdery mildew spore suspension is inoculated on the cucumber leaves and is cultured in a greenhouse, and after 15 days, the development degree of germ infection on the leaves is measured.
The individual active ingredients and the activity data of the compositions according to the invention for controlling cucumber powdery mildew are shown in tables 3 and 4.
TABLE 3 Activity of the Individual active Components
TABLE 4 Activity of the compositions of the invention
The results show that the observed efficacy values of the compositions are all larger than the calculated efficacy values, and the compositions show synergistic effect within the range of the experimental mixture ratio.
Example 3 corn rust control test
The method comprises the following steps of spraying and treating potted two-leaf stage corn seedlings of 'golden yellow glutinous' varieties by using aqueous solutions (the concentration is shown in the table below) of active components or compositions, inoculating corn rust germ spore suspension on corn leaves after 24 hours, culturing in a climatic chamber, transferring the corn leaves into a greenhouse for culturing after the diseases are infected, and measuring the development degree of germ infection on the leaves after 12 days.
The activity data for the individual active components and for the compositions according to the invention for maize rust are shown in tables 5 and 6.
TABLE 5 Activity of the Individual active Components
TABLE 6 Activity of the compositions of the invention
The results show that the observed efficacy values of the compositions are all larger than the calculated efficacy values, and the compositions show synergistic effect within the range of the experimental mixture ratio.
Example 4 Soybean Rust control test
Selecting potted soybean seedlings (variety: Liaodou 10) with uniform growth, cutting off growing points, reserving 2 true leaves, carrying out spray treatment by using aqueous solutions (the concentration is shown in the table) of active components or compositions, inoculating a soybean rust spore suspension, culturing in a climatic chamber, transferring into a greenhouse for culturing after the infection of diseases is finished, and measuring the development degree of the pathogen infection on the leaves after 10 days.
The results of the data on the activity of the individual active ingredients and of the compositions according to the invention against soybean rust are shown in tables 7 and 8.
TABLE 7 Activity of the Individual active Components
TABLE 8 Activity of the compositions of the invention
The results show that the observed efficacy values of the compositions are all larger than the calculated efficacy values, and the compositions show synergistic effect within the range of the experimental mixture ratio.
Example 5 test for controlling Rice sheath blight disease
Selecting rice potted seedling (variety: Liaoxing No. 2) with uniform growth, spraying with aqueous solution (concentration shown in the following table) of each active component or composition, inoculating by using a sandwich inoculation method after 24 hours, inoculating to the base of the rice seedling, culturing in a greenhouse, and measuring the development degree of germ infection on leaf sheath after 5 days.
The results of the data of the activity of each individual active component and the composition of the invention for controlling rice sheath blight disease are shown in tables 9 and 10.
TABLE 9 Activity of the Individual active Components
TABLE 10 Activity of the compositions of the invention
The results show that the observed efficacy values of the compositions are all larger than the calculated efficacy values, and the compositions show synergistic effect within the range of the experimental mixture ratio.
Claims (10)
1. A fungicidal composition characterized by: 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 as a general formula I-1F or a salt thereof.
In the formula:
R3selected from hydrogen, hydroxy, formyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylthio radical, C2-C4Alkenylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkenyl, halo C2-C4Alkynyl, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkylsulfinyl, halogeno C1-C4Alkylsulfinyl radical, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylaminosulfonyl, di (C)1-C4Alkyl) aminosulfonyl, C1-C4Alkylsulfonylaminocarbonyl group, C1-C4Alkylcarbonylaminosulfonyl radical, C3-C4Cycloalkyloxycarbonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkyl carbonyl radical C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylaminocarbonyl, di (C)1-C4Alkyl) aminocarbonyl, C2-C4Alkenyloxycarbonyl radical, C2-C4Alkynyloxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkoxycarbonyl group, C1-C4Alkylaminosulfenyl, di (C)1-C4Alkyl) aminosulfanyl, (hetero) arylcarbonyl C which is unsubstituted or further substituted by 1 to 51-C4Alkyl, (hetero) arylcarbonyl, (hetero) aryloxycarbonyl, (hetero) aryl C1-C4Alkyloxycarbonyl, (hetero) aryl C1-C4Alkyl, halogen, nitro or cyano;
R4、R5can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group; wherein R is4、R5C attached thereto may also form C3-C4A ring of (a);
R6、R7can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group; wherein R is6、R7C attached thereto may also form C3-C4A ring of (a);
R8、R9can be the same or different and are respectively selected from hydrogen, cyano, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl, unsubstituted or substituted by 1 to 5R11Substituted (hetero) aryl, (hetero) arylmethyl, (hetero) arylcarbonyl, (hetero) arylmethylcarbonyl or (hetero) aryloxycarbonyl;
R11selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylamino, halogeno C1-C4Alkylamino radical, di (C)1-C4Alkyl) amino, halo-di (C)1-C4Alkyl) amino, C1-C4Alkylthio, halo C1-C4Alkylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, C2-C4Alkenyloxy, halogeno C2-C4Alkenyloxy radical, C2-C4Alkynyloxy, halo C2-C4Alkynyloxy, C1-C4Alkylsulfonyl, halo C1-C4Alkylsulfonyl radical, C1-C4Alkylcarbonyl, halo C1-C4Alkylcarbonyl group, C1-C4Alkoxycarbonyl, halo C1-C4Alkoxycarbonyl group, C1-C4Alkoxy radical C1-C4Alkyl, halo C1-C4Alkoxy radical C1-C4Alkyl radical, C1-C4Alkylthio group C1-C4Alkyl, halo C1-C4Alkylthio group C1-C4Alkyl radical, C1-C4Alkoxycarbonyl radical C1-C4Alkyl, halo C1-C4Alkoxycarbonyl radical C1-C4Alkyl radical, C1-C4Alkylthio carbonyl group C1-C4Alkyl, halo C1-C4Alkylthio carbonyl group C1-C4Alkyl radical, C1-C4Alkylcarbonyloxy, halo C1-C4Alkylcarbonyloxy, C1-C4Alkoxy carbonyl oxygen radicalHalogen substituted C1-C4Alkoxycarbonyloxy, C1-C4Alkylsulfonyloxy, halo C1-C4Alkylsulfonyloxy, C1-C4Alkoxy radical C1-C4Alkoxy or halo C1-C4Alkoxy radical C1-C4An alkoxy group; n is an integer of 0 to 5, and when n is greater than 1, R11May be the same or different;
R14、R15、R16or R17Can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy or C3-C4A cycloalkyl group;
w is selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkoxy radical, C1-C4Alkylthio or C1-C4An alkylsulfonyl group;
the active component B is selected from one or more of triazole bactericides.
2. The fungicidal composition according to claim 1, characterized in that: the active component A is a salt of a compound shown as a general formula I-1F, wherein the salt of the compound shown as the general formula I-1F is a salt formed by the compound shown as the general formula I-1F 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, fumaric acid, sorbic acid, malic acid or citric acid.
3. The fungicidal composition according to claim 1, characterized in that: the weight ratio of A, B to 50:1 of the two active components in the composition is 1:50-50: 1;
the active component A is a compound shown as a general formula I-1F or a salt thereof;
in the general formula R3Selected from hydrogen,Hydroxy, formyl, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylthio radical, C2-C4Alkenylthio radical, C2-C4Alkenyl radical, C2-C4Alkynyl, halo C2-C4Alkenyl or halogeno C2-C4An alkynyl group;
R4、R5can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
R6、R7can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
R8、R9can be the same or different and are respectively selected from hydrogen, cyano, halogen and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxycarbonyl or halo C1-C4An alkoxycarbonyl group;
R11selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy, halo C1-C4Alkoxy radical, C3-C4Cycloalkyl radical, C1-C4Alkylamino or halogeno C1-C4An alkylamino group; n is an integer of 0 to 5, and when n is greater than 1, R11May be the same or different;
R14、R15、R16or R17Can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl, halo C1-C4Alkyl radical, C1-C4Alkoxy or halo C1-C4An alkoxy group;
w is selected from hydrogen, halogen, C1-C4Alkyl, halo C1-C4Alkyl radical, C3-C4Cycloalkyl radical, C1-C4Alkoxy or C1-C4An alkylthio group;
the active component B is selected from one or more of tebuconazole B1, propiconazole B2, difenoconazole B3, epoxiconazole B4, triadimefon B5, flusilazole B6, high-efficiency diniconazole B7, myclobutanil B8, diniconazole B9, penconazole B10, hexaconazole B11, triadimenol B12, cyproconazole B13, fluquinconazole B14, flutriafol B15, metconazole B16, imibenconazole B17, prothioconazole B18, ipconazole B19, triticonazole B20, bitertazol B21, epoxiconazole B22, tetraconazole B23, imazalil B24, high-efficiency imazalil B25, tetraconazole 26 or metconazole 28.
4. The fungicidal composition according to claim 3, characterized in that: the active component A is a salt of a compound shown in a general formula I-1F, wherein the salt of the compound shown in the general formula I-1F is a salt formed by the compound shown in the general formula I-1F and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid or maleic acid.
5. The fungicidal composition according to claim 3, characterized in that: the weight ratio of A, B to 20:1 of the two active components in the composition is 1:20-20: 1;
the active component A is a compound in a general formula I-1F or a salt thereof;
in the general formula R3Selected from hydrogen, hydroxy, formyl, C1-C4Alkyl or halo C1-C4An alkyl group; r4、R5Can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl or halo C1-C4An alkyl group; r6、R7Can be the same or different and are respectively selected from hydrogen, halogen and C1-C4Alkyl or halo C1-C4An alkyl group;R8、R9can be the same or different and are respectively selected from hydrogen, cyano, halogen and C1-C4Alkyl or halo C1-C4An alkyl group; r11Selected from halogen, hydroxy, amino, cyano, nitro, C1-C4Alkyl or halo C1-C4An alkyl group; n is an integer of 0 to 5, and when n is greater than 1, R11May be the same or different; r14、R15、R16Or R17Can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro and C1-C4Alkyl or halo C1-C4An alkyl group; w is selected from hydrogen, halogen, C1-C4Alkyl or halo C1-C4An alkyl group;
the active component B is selected from one or more of tebuconazole B1, propiconazole B2, difenoconazole B3, epoxiconazole B4, triadimefon B5, flusilazole B6, diniconazole B7, myclobutanil B8, hexaconazole B11, cyproconazole B13, flutriafol B15, imibenconazole B17, prothioconazole B18, triticonazole B20, bitertanol B21 or tetraconazole B23.
6. The fungicidal composition according to claim 5, characterized in that: the active component A is a salt of a compound shown in a general formula I-1F, wherein the salt of the compound shown in the general formula I-1F is a salt formed by the compound shown in the general formula I-1F and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid or methanesulfonic acid.
7. The fungicidal composition according to claim 5, characterized in that: the weight ratio of the A, B active components is 1:10-10: 1;
the active component A is a compound shown as a general formula I-1F or a salt thereof, wherein R in the general formula3Selected from hydrogen, hydroxy, formyl or C1-C4An alkyl group; r4、R5Can be the same or different and are respectively selected from hydrogen, halogen or C1-C4An alkyl group; r6、R7Can be the same or different and are respectively selected from hydrogen and halogenOr C1-C4An alkyl group; r8、R9Can be the same or different and are respectively selected from hydrogen, cyano, halogen or C1-C4An alkyl group; r11Selected from halogen, hydroxy, amino, cyano, nitro or C1-C4An alkyl group; n is an integer of 0 to 5, and when n is greater than 1, R11May be the same or different; r14、R15、R16Or R17Can be the same or different and are respectively selected from hydrogen, halogen, hydroxyl, amino, cyano, nitro or C1-C4An alkyl group; w is selected from hydrogen, halogen or C1-C4An alkyl group;
the active component B is selected from one or more of tebuconazole B1, propiconazole B2, difenoconazole B3, epoxiconazole B4, triadimefon B5, flusilazole B6, myclobutanil B8, hexaconazole B11, cyproconazole B13, flutriafol B15, imibenconazole B17, prothioconazole B18 or tetraconazole B23.
8. The fungicidal composition according to claim 7, characterized in that: the active component A is a salt of a compound shown in a general formula I-1F, wherein the salt of the compound shown in the general formula I-1F is a salt formed by the compound shown in the general formula I-1F and hydrochloric acid, sulfuric acid, phosphoric acid, formic acid or acetic acid.
9. Use of a fungicidal composition according to claim 1, characterized in that: the fungicidal compositions are used for the preparation of medicaments for controlling phytopathogenic fungal diseases.
10. Use of a fungicidal composition according to claim 9, characterized in that: the plant pathogenic fungus diseases are plant powdery mildew, scab, rust disease, leaf mold, banded sclerotial blight, black nevus, ring spot, alternaria leaf spot or damping off.
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| WO2012165266A1 (en) * | 2011-05-27 | 2012-12-06 | Ishihara Sangyo Kaisha, Ltd. | Method for controlling plant diseases |
| CN104710436A (en) * | 2013-12-13 | 2015-06-17 | 中国中化股份有限公司 | Pyrazolyl pyrilamine compound and use thereof |
| CN106167484A (en) * | 2015-05-18 | 2016-11-30 | 沈阳中化农药化工研发有限公司 | Substituted pyrazolecarboxylic compounds containing pyrimidine and its production and use |
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| WO2012165266A1 (en) * | 2011-05-27 | 2012-12-06 | Ishihara Sangyo Kaisha, Ltd. | Method for controlling plant diseases |
| CN104710436A (en) * | 2013-12-13 | 2015-06-17 | 中国中化股份有限公司 | Pyrazolyl pyrilamine compound and use thereof |
| CN106167484A (en) * | 2015-05-18 | 2016-11-30 | 沈阳中化农药化工研发有限公司 | Substituted pyrazolecarboxylic compounds containing pyrimidine and its production and use |
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| WO2021104171A1 (en) * | 2019-11-25 | 2021-06-03 | 沈阳中化农药化工研发有限公司 | Bactericidal composition and use thereof |
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