CN112189663B - Fungicidal and bacterial composition and application - Google Patents
Fungicidal and bacterial composition and application Download PDFInfo
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- CN112189663B CN112189663B CN201910609653.2A CN201910609653A CN112189663B CN 112189663 B CN112189663 B CN 112189663B CN 201910609653 A CN201910609653 A CN 201910609653A CN 112189663 B CN112189663 B CN 112189663B
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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
- 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
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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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
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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
- A01N43/74—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 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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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
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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)
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- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to a fungicidal and bactericidal composition and a method of use thereof, the composition comprising A, B two active ingredients, wherein ingredient A is selected from compounds of formula I:
Description
Technical Field
The invention belongs to the field of agricultural bactericides, and particularly relates to a fungicidal and bactericidal composition and application thereof.
Background
Chinese invention patent CN201611199611.9 and PCT application WO CN16111411 disclose malononitrile oxime ether compounds, which have good control effect on plant pathogenic fungi and bacteria. The malononitrile oxime ether compound has good control effect on various plant diseases caused by plant pathogenic fungi such as oomycetes, basidiomycetes, ascomycetes, deuteromycetes and the like, including cucumber downy mildew, cucumber gray mold, cucumber anthracnose, cucumber powdery mildew, tomato early blight, tomato late blight, pepper phytophthora blight, grape downy mildew, grape white rot, apple ring rot, apple alternaria leaf spot, rice sheath blight, rice blast, wheat rust, wheat leaf spot, wheat powdery mildew, rape sclerotinia rot, corn small spot and the like; meanwhile, the composition has good control effects on various plant diseases caused by plant pathogenic bacteria such as pseudomonas, erwinia, xanthomonas, acidophilus and the like, including tomato bacterial wilt, tobacco bacterial wilt, citrus canker, kiwi canker, Chinese cabbage soft rot, cucumber bacterial angular leaf spot and the like.
The benziothiazolinone is an organic heterocyclic bactericide, has good control effect on various plant fungi and bacterial diseases, and can be used for controlling diseases such as cucumber fusarium wilt, wheat scab, cucumber damping off, rice bacterial leaf blight, cucumber bacterial angular leaf spot and the like.
Practical agricultural experience and extensive scientific research data have shown that the long-term repeated and specific application of one type of compound for controlling plant fungi and bacterial diseases leads in many cases to a rapid selectivity of pathogenic bacteria and fungal strains, some strains developing an adapted resistance to a particular active compound, resulting in a significant reduction, or even a complete loss, of the control effect of the active compound.
Disclosure of Invention
The present invention aims to provide a fungicidal and bacterial composition and the use thereof in order to reduce the risk of resistance of pathogenic fungi and bacteria to active compounds and to improve the control of pathogenic fungi and bacteria.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a fungicidal and bactericidal composition comprises a component A and a component B; the weight ratio of the A, B components is 1: 100-100: 1; wherein, the component A is malononitrile oxime ether compound shown in a general formula I; the component B is benziothiazolinone;
the malononitrile oxime ether compound shown in the general formula I:
in the formula:
l is selected from- (CR)1R2)n-；
n is selected from 1 or 2;
when n ═ 2, W is phenyl; when n is 1, W is selected from W1、W2、W3、W4、W12、W16、W21、W23、W47、W48、W49、W59、W67、W68、W69、W70、W71、W72、W73、W74、W79、W80、W81、W82、W83Or W84；
Wherein:
X1、X2、X3、X4、X5、X6、X7、X8、X9each independently selected from hydrogen, halogen, cyano, nitro, C1-C3Alkyl radical, C1-C3Haloalkyl, -OR3、-N(R4)S(＝O)2R5、-S(＝O)2NR3R5、-CH2ON＝C(CN)2Phenyl and pyridyl unsubstituted or optionally substituted by halogen, cyano, C1-C3A haloalkyl group; when W is W1When, X1、X2、X3、X4、X5Not hydrogen at the same time; or W1Is composed of
Z is selected from hydrogen and C1-C3Alkyl, phenylmethyl;
k is selected from oxygen;
R3selected from hydrogen, C1-C3Alkyl radical, C1-C3Haloalkyl, phenyl or pyridyl unsubstituted or optionally substituted by halogen or C1-C3A haloalkyl group;
R4、R5each independently selected from hydrogen and C1-C3An alkyl group;
q is selected from Q1-2One of the groups shown, phenyl and pyridyl which are unsubstituted or optionally substituted by the following groups, wherein the following groups are halogen and C1-C3An alkyl group;
t is selected from phenyl and pyridyl which are unsubstituted or optionally substituted by halogen, cyano, C1-C3Alkyl, halo C1-C3Alkyl, halo C1-C3An alkoxy group.
Preferably, the component A in the composition is malononitrile oxime ether compounds shown in the general formula I:
wherein L is selected from: - (CR)1R2)n-；
n is selected from 1;
R1、R2selected from hydrogen;
w is selected from W1、W2、W3、W4、W12、W16、W21、W23、W48、W49、W59、W67、W68、W69、W70、W71、W72、W73、W74、W79、W80、W81、W82、W83Or W84；
X1、X2、X3、X4、X5、X6、X7、X8、X9Each independently selected from hydrogen, halogen, cyano, nitro, C1-C3Alkyl radical, C1-C3Haloalkyl, -OR3Phenyl and pyridyl unsubstituted or optionally substituted by halogen, cyano, C1-C3A haloalkyl group; when W is W1When, X1、X2、X3、X4、X5Not hydrogen at the same time;
z is selected from hydrogen and C1-C3An alkyl group;
k is selected from oxygen;
R3is selected from C1-C3Alkyl radical, C1-C3Haloalkyl, phenyl or pyridyl unsubstituted or optionally substituted by halogen or C1-C3A haloalkyl group;
q is selected from Q1-2One of the groups shown, phenyl and pyridyl which are unsubstituted or optionally substituted by the following groups, wherein the following groups are halogen and C1-C3An alkyl group;
t is selected from phenyl and pyridyl which are unsubstituted or optionally substituted by halogen, cyano, C1-C3Alkyl, halo C1-C3Alkyl, halo C1-C3An alkoxy group;
the component B is benziothiazolinone;
wherein the weight ratio of the A, B components is 1: 90-90: 1.
further preferably, the weight ratio of the A, B components is 1: 75-75: 1; wherein, the component A is malononitrile oxime ether compound shown in the general formula I:
in the formula (I), the compound is shown in the specification,
l is selected from- (CR)1R2)n-；
n is selected from 1;
R1、R2selected from hydrogen;
w is selected from W1、W2、W3、W4、W16、W49、W59、W69、W70、W71、W72、W79、W80Or W81；
X1、X2、X3、X4、X5、X6Each independently selected from hydrogen, halogen, cyano, nitro, C1-C3Alkyl radical, C1-C3Haloalkyl, -OR3Phenyl which is unsubstituted or optionally substituted by halogen, cyano, C1-C3A haloalkyl group; when W is W1When, X1、X2、X3、X4、X5Not hydrogen at the same time;
z is selected from hydrogen;
k is selected from oxygen;
R3is selected from C1-C3Alkyl radical, C1-C3A haloalkyl group;
q is selected from Q1-2One of the groups shown, phenyl and pyridyl which are unsubstituted or optionally substituted by the following groups, wherein the following groups are halogen and C1-C3An alkyl group;
t is selected from phenyl and pyridyl which are unsubstituted or optionally substituted by halogen and C1-C3Alkyl, halo C1-C3Alkyl, halo C1-C3An alkoxy group;
the component B is benziothiazolinone.
In a further preferred aspect, the A, B weight ratio between the two components is 1: 50-50: 1; wherein, the component A is malononitrile oxime ether compound shown in the general formula I:
in the formula (I), the compound is shown in the specification,
l is selected from- (CR)1R2)n-；
n is selected from 1;
R1、R2selected from hydrogen;
w is selected from W1、W2、W3、W4、W16、W49Or W69；
X1、X2、X3、X4、X5Each independently selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, chloromethyl, bromomethyl, difluoromethyl, trifluoromethyl, -OR3Phenyl which is unsubstituted or optionally substituted by halogen or cyano; when W is W1When, X1、X2、X3、X4、X5Not hydrogen at the same time;
R3selected from methyl or trifluoromethyl;
the component B is benziothiazolinone.
More preferably, the weight ratio between the A, B two components is 1: 20-20: 1; wherein, the component A is malononitrile oxime ether compound shown in the general formula I:
in the formula (I), the compound is shown in the specification,
l is selected from- (CR)1R2)n-；
n is selected from 1;
R1、R2selected from hydrogen;
w is selected from W1；
X1、X2、X3、X4、X5Each independently selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, chloromethyl, bromomethyl, difluoromethyl, trifluoromethyl, -OR3Phenyl which is unsubstituted or optionally substituted by halogen or cyano; when W is W1When, X1、X2、X3、X4、X5Not hydrogen at the same time;
R3selected from methyl or trifluoromethyl;
component B is selected from benziothiazolinone.
The use of said fungicidal, bacterial compositions as a control against phytopathogenic harmful fungi, bacteria.
The compositions are useful for controlling harmful fungi, bacterial infections, infestations of plants, seeds, soils, areas, materials or spaces.
The composition is used for preventing and treating plant fungi and bacterial diseases of grains, rice, fruit trees, vegetables, flowers, traditional Chinese medicinal materials or lawns.
The fungicidal and bacterial composition is used for preventing and treating plant fungi and bacterial diseases by adopting a mode of spraying, irrigating roots or soaking seeds on leaf surfaces or the whole plants.
The preferred technical solution of the fungicidal, bacterial composition according to the invention is that component a is selected from the compounds listed in the following table:
the composition of the invention is suitable for controlling various harmful fungi and bacteria, especially various diseases of cereals, vegetables, fruit trees, ornamental plants, lawns and tropical crops, and various storage diseases.
When preparing the composition, at least one of the A-component compound and the B-component compound may be added thereto with other active substances effective against harmful pathogenic microorganisms or other pests, or with active compounds or fertilizers having herbicidal action as well as growth regulating action.
The combination, whether used in any form, i.e., the combined use of at least one of the a-component compounds and the B-component compounds, exhibits a significant increase in the spectrum of disease control and enhanced control of certain diseases, including a variety of plant diseases caused by a variety of pathogenic microorganisms, such as pathogenic fungi and bacteria. The composition is especially important for preventing and controlling fungal and bacterial diseases of various crops such as grains, rice, vegetables, fruit trees and flowers, and is used for dressing seeds and protecting the crops. Is particularly suitable for preventing and treating the following plant fungal and bacterial diseases: rice blast, rice sheath blight, rice bacterial leaf streak, cucumber fusarium wilt, cucumber downy mildew, cucumber powdery mildew, cucumber gray mold, cucumber bacterial angular leaf spot, tomato leaf mold, tomato bacterial wilt, apple ring rot, apple alternaria leaf spot, pepper blight, watermelon fusarium wilt, wheat scab, wheat take-all, soybean root rot, citrus canker, kiwi canker, tobacco bacterial wilt, Chinese cabbage soft rot, melon bacterial fruit blotch and the like.
In controlling plant diseases, the composition of the present invention may be applied before or after sowing of the plant, or by spraying or dusting the seed, plant or soil before or after emergence of the plant.
The invention has the advantages that:
the fungicidal and bacterial composition has very obvious synergistic effect, obviously improves the control effect on crop diseases, and can expand the bactericidal spectrum and delay the occurrence of drug resistance of pathogenic substances;
the invention combines the compounds with different action mechanisms and chemical structure types, can more effectively control harmful microorganisms influencing the growth of crops, and has synergistic effect so as to achieve the aims of effectively treating resistance and effectively controlling plant diseases.
Detailed Description
The synergistic effect of the fungicidal, bacterial compositions according to the invention on harmful fungi and bacterial diseases can be illustrated by the following examples, to which the invention is in no way restricted.
The active compounds, alone or in combination, are prepared as acetone or DMSO stock solutions containing 0.25% by weight of active compound. 1% by weight of emulsifier
EL (a wetting agent based on ethoxylated alkylphenol with emulsifying and dispersing action) is added to the stock solution and the active compound or mixture is diluted with water to the concentration required in the examples below.
The expected potency of the active compound mixtures was determined using the Colby formula [ S.R.Colby.calcium synergy and antibiotic Responses of pharmaceutical compositions.Weeds, 1967,15(1):20-22] and compared with the observed potency.
Colby formula: e ═ x + y-xy/100
E: the expected efficacy when using mixtures of active compounds a and B at concentrations a and B, respectively, is expressed as% of the untreated control.
x efficacy when using active compound a at a concentration a, expressed as% of untreated control;
y efficacy when using active compound B at a concentration of B, expressed as% of the untreated control.
If the actual observed efficacy (O) is greater than the expected efficacy (E), the effect of the combination is a synergistic effect, which corresponds mathematically to a positive difference in (O-E). If the actual observed efficacy (O) is equal to the expected efficacy (E), the effect of the combination is a purely additive effect, showing no synergy, mathematically the difference corresponding to (O-E) is zero. If the actual observed potency (O) is less than the expected potency (E), then the effect of the combination is an antagonistic effect, mathematically the difference corresponding to (O-E) is negative.
Application example 1 test for controlling bacterial leaf blight of rice
Potted rice seedlings of cultivar "wanxiangyou No. 1" were cultivated to the trefoil stage and sprayed to the drip point with an aqueous suspension of the active compound at the concentrations described below. After 24 hours, the leaves of the rice plants are inoculated with an aqueous suspension of Xanthomonas oryzae pv. oryzae, and the rice seedlings are then cultured for 7 days in a climatic chamber at 25 to 30 ℃ and a relative humidity of 95 to 99%. And finally, visually measuring the development degree of pathogen infection on the rice leaves.
The data and results of the individual active ingredients and the composition of the invention for controlling bacterial blight of rice are shown in tables 1 and 2. The results show that the observed efficacy values of the composition are all larger than the calculated efficacy values, which indicates that the composition shows a synergistic effect in the range of the experimental mixture ratio.
TABLE 1 Activity of the Individual active ingredients
TABLE 2 Activity of the compositions of the invention
Application example 2 test for controlling tomato bacterial wilt
Potted tomato seedlings of cultivar "donglily" were cultivated to the two-leaf stage and sprayed to the drip point with an aqueous suspension of the active compound at the concentration described below. After 24 hours, tomato seedlings were inoculated with an aqueous suspension of Ralstonia solanacearum, and then the seedlings were cultured in a climate chamber at 22 to 26 ℃ and a relative humidity of 95 to 99% for 3 days. And finally, visually measuring the development degree of pathogen infection on the tomato seedlings.
The data and results of the individual active ingredients and the inventive compositions for controlling tomato bacterial wilt are shown in tables 3 and 4. The results show that the observed efficacy values of the composition are all larger than the calculated efficacy values, which indicates that the composition shows a synergistic effect in the range of the experimental mixture ratio.
TABLE 3 Activity of the Individual active Components
TABLE 4 Activity of the compositions of the invention
Application example 3 test for controlling cucumber powdery mildew
Potted cucumber seedlings of the cultivar "Shandong Mici" were cultivated to the two-leaf stage and sprayed to the drip point with an aqueous suspension of the active compound at the concentrations stated below. After 24 hours, the cucumber leaves are inoculated with an aqueous spore suspension of cucumber powdery mildew (Sphaerotheca fuliginea), after which the cucumber seedlings are cultivated for 3 days in a climate chamber at 24 to 28 ℃ and a relative humidity of 90 to 95%. And finally, visually measuring the development degree of pathogen infection on the cucumber leaves.
The data and results of the individual active ingredients and the inventive compositions for controlling cucumber powdery mildew are given in tables 5 and 6. The results show that the observed efficacy values of the composition are all larger than the calculated efficacy values, which indicates that the composition shows a synergistic effect in the range of the experimental mixture ratio.
TABLE 5 Activity of the Individual active Components
TABLE 6 Activity of the compositions of the invention
Application example 4 field plot experiment for controlling bacterial leaf streak of rice
A field block which generates rice bacterial leaf streak (Xanthomonas oryzae pv. oryzicola) all the year round is selected to carry out field plot experiments, and the rice cultivar is Wanxiangyou No. 1. The test adopts a random block design, the area of a cell is 25 square meters, the cell is repeated for four times, and the medicament treatment is carried out for two times in total at one week interval. The first treatment with the agent was started when bacterial leaf streak lesions were first observed in the field, and the rice plants were sprayed with an aqueous suspension of the active compound at the concentrations described below using a knapsack sprayer, one week later with a second spraying treatment. One week after the last spraying treatment, the degree of development of pathogen infestation on the rice leaves was determined visually and the average of four replicates of each treatment was calculated (see tables 7 and 8).
TABLE 7 Activity of the Individual active Components
TABLE 8 Activity of the compositions of the invention
The data results of the individual active components and the composition for preventing and treating the bacterial leaf streak of the rice show that the observation efficacy values of the composition are all larger than the calculation efficacy values, which indicates that the composition shows a synergistic effect in the range of the experimental mixture ratio.
Claims (6)
1. A fungicidal, bacterial composition, characterized in that: the composition comprises a component A and a component B; the weight ratio of the A, B components is 1: 20-20: 1; wherein, the component A is malononitrile oxime ether compound shown in a general formula I; the component B is benziothiazolinone;
in the formula:
l is selected from- (CR)1R2)n-；R1、R2Selected from hydrogen;
n is selected from 1 or 2;
when n ═ 2, W is phenyl; when n is 1, W is selected from
2. Use of the fungicidal, bacterial composition according to claim 1, characterized in that: the composition is used for controlling plant pathogenic harmful fungi and bacteria.
3. The use of a fungicidal, bacterial composition according to claim 2, characterized in that: the composition is used for controlling harmful fungi, bacterial infection, and plant or soil invasion.
4. The use of a fungicidal, bacterial composition according to claim 2, characterized in that: the composition is used for preventing and treating harmful fungi, bacterial infection and invasion of seeds.
5. The use of a fungicidal, bacterial composition according to claim 3 or 4, characterized in that: the composition is used for preventing and treating plant fungi and bacterial diseases of grains, fruit trees, vegetables, flowers, traditional Chinese medicinal materials or lawns.
6. The use of a fungicidal, bacterial composition according to claim 2, characterized in that: the fungicidal and bacterial composition is used for preventing and treating plant fungi and bacterial diseases by adopting a mode of spraying, irrigating roots or soaking seeds on leaf surfaces or the whole plants.
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Citations (6)
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|---|---|---|---|---|
| US3694482A (en) * | 1970-04-15 | 1972-09-26 | Exxon Research Engineering Co | Malononitrile oxime derivatives |
| CN1109686A (en) * | 1993-05-18 | 1995-10-04 | 希巴-盖吉股份公司 | O-benzyl oxime ether derivatives and their use as pesticides |
| WO1997007099A1 (en) * | 1995-08-16 | 1997-02-27 | Agrevo Uk Limited | Alpha-methoxymethylene or alpha-methoxyimino naphthylacetic acid derivatives and their use as fungicides |
| CN1250046A (en) * | 1998-10-07 | 2000-04-12 | 湖南化工研究院 | Biocidal oximido ether compound |
| CN102227423A (en) * | 2008-12-02 | 2011-10-26 | 纳幕尔杜邦公司 | Fungicidal heterocyclic compounds |
| CN106916084B (en) * | 2015-12-25 | 2019-06-11 | 沈阳中化农药化工研发有限公司 | A kind of malononitrile oximido ether compound and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE525907T1 (en) * | 2005-10-19 | 2011-10-15 | Bayer Cropscience Inc | FUNGICIDE CONTROL OF MOLD |
-
2019
- 2019-07-08 CN CN201910609653.2A patent/CN112189663B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3694482A (en) * | 1970-04-15 | 1972-09-26 | Exxon Research Engineering Co | Malononitrile oxime derivatives |
| CN1109686A (en) * | 1993-05-18 | 1995-10-04 | 希巴-盖吉股份公司 | O-benzyl oxime ether derivatives and their use as pesticides |
| WO1997007099A1 (en) * | 1995-08-16 | 1997-02-27 | Agrevo Uk Limited | Alpha-methoxymethylene or alpha-methoxyimino naphthylacetic acid derivatives and their use as fungicides |
| CN1250046A (en) * | 1998-10-07 | 2000-04-12 | 湖南化工研究院 | Biocidal oximido ether compound |
| CN102227423A (en) * | 2008-12-02 | 2011-10-26 | 纳幕尔杜邦公司 | Fungicidal heterocyclic compounds |
| CN106916084B (en) * | 2015-12-25 | 2019-06-11 | 沈阳中化农药化工研发有限公司 | A kind of malononitrile oximido ether compound and application thereof |
| CN109942461A (en) * | 2015-12-25 | 2019-06-28 | 沈阳中化农药化工研发有限公司 | Malononitrile oximido ether compound and application thereof |
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