CN100410244C - Application of isoxazole compounds as bactericide - Google Patents
Application of isoxazole compounds as bactericide Download PDFInfo
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- CN100410244C CN100410244C CNB2005100471528A CN200510047152A CN100410244C CN 100410244 C CN100410244 C CN 100410244C CN B2005100471528 A CNB2005100471528 A CN B2005100471528A CN 200510047152 A CN200510047152 A CN 200510047152A CN 100410244 C CN100410244 C CN 100410244C
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Abstract
The present invention discloses one kind of isoxazole compound and its application as germicide, and the compound has structure as shown in the general expression.
Description
Technical field
The invention belongs to the disinfectant use in agriculture field, relate to of the application of a kind of isoxazole compounds specifically as sterilant.
Background technology
De isoxazole compounds shown in the following general formula:
In the formula: R is selected from hydrogen, halogen, cyano group, nitro, C
1-C
12Alkyl, C
2-C
12Thiazolinyl, C
2-C
12Alkynyl, C
1-C
12Haloalkyl, C
1-C
12Alkoxyl group, C
1-C
12Halogenated alkoxy, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl, C
1-C
12Alkoxy carbonyl, C
1-C
12Alkoxy carbonyl C
1-C
12The amino of alkyl, replacement; R
1Be selected from hydrogen, halogen, cyano group, nitro, C
1-C
12Alkyl, C
1-C
12Alkoxyl group, C
1-C
12Alkoxy carbonyl, C
1-C
12Alkoxy carbonyl C
1-C
12Alkyl; N is selected from 1～5; M is selected from basic metal, mantoquita, ammonium salt, zinc salt.
Although these compounds are known mostly, there is not the fungicidal activity report.
Patent US3781438 once disclosed the compound of following general formula, had eelworm-killing activity:
Point out X=Cl, Br, CN in these patent claims, they are made by intermediate X=OH.However, this patent does not disclose its intermediate (X=OH) biologically active.
Patent EP396215 discloses following general formula and particular compound thereof, has eelworm-killing activity:
Known some isoxazole compounds has fungicidal activity, but De isoxazole compounds difference is very big shown in the general formula that its structure and the present invention propose.For example:
The following compound of reports such as patent GB1009801 has fungicidal activity, and the drazoxolon commercialization is arranged.
Patent JP 51127072 discloses following compound, has fungicidal activity:
Hymexazo (hymexazol) is commercial sterilant, and chemical structure is as follows:
Summary of the invention
Novel germicide for the various crop pests of control that obtain new mechanism of action uniqueness, inventor of the present invention has carried out research in depth to the fungicidal activity of De isoxazole compounds shown in the following general formula, found that this compounds has the fungicidal activity of wide spectrum---can be used for control on various crops by multiple germ diseases such as Oomycete, Basidiomycetes, ascomycetes and imperfect fungis, and because these compounds have very high biological activity makes just can obtain good effect under very low dosage.This compounds is to uncinula necator, oidium; Powdery mildew of cucumber, oidium; Rice sheath blight disease, rice blast, bakanae disease; Cotton wilt; Early blight of tomato, late blight; Diseases such as wheat rust, leaf spot, Powdery Mildew all have good preventive effect.
Provided by the present invention to can be used as the isoxazole compounds that sterilant uses main shown in following general formula (I), also comprises its isomer (II) and salt thereof or complex compound (III) simultaneously.
In the formula:
R is selected from hydrogen, halogen, cyano group, nitro, C
1-C
12Alkyl, C
2-C
12Thiazolinyl, C
2-C
12Alkynyl, C
1-C
12Haloalkyl, C
1-C
12Alkoxyl group, C
1-C
12Halogenated alkoxy, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl, C
1-C
12Alkoxy carbonyl, C
1-C
12Alkoxy carbonyl C
1-C
12Alkyl, replacement or unsubstituted amino;
R
1Be selected from hydrogen, halogen, cyano group, nitro, C
1-C
12Alkyl, C
1-C
12Alkoxyl group, C
1-C
12Alkoxy carbonyl or C
1-C
12Alkoxy carbonyl C
1-C
12Alkyl;
N is selected from 1～5;
M is selected from basic metal, alkaline-earth metal, mantoquita, ammonium salt or zinc salt.
When using as sterilant in the above-mentioned isoxazole compounds comparatively preferably: in the general formula (I)～(III)
R is selected from hydrogen, halogen, cyano group, nitro, C
1-C
6Alkyl, C
2-C
6Thiazolinyl, C
2-C
6Alkynyl, C
1-C
6Haloalkyl, C
1-C
6Alkoxyl group, C
1-C
6Halogenated alkoxy, C
1-C
6Alkylthio, C
1-C
6Alkyl sulphonyl, C
1-C
6Alkoxy carbonyl, C
1-C
6Alkoxy carbonyl C
1-C
6Alkyl, replacement or unsubstituted amino;
R
1Be selected from hydrogen, halogen, cyano group, nitro, C
1-C
6Alkyl, C
1-C
6Alkoxyl group, C
1-C
6Alkoxy carbonyl, C
1-C
6Alkoxy carbonyl C
1-C
6Alkyl;
N is selected from 1～5;
M is selected from basic metal, alkaline-earth metal, mantoquita, ammonium salt or zinc salt.
Further preferred compound is: in the general formula (I)～(III)
R is selected from hydrogen, chlorine, bromine, fluorine, cyano group, nitro, C
1-C
3Alkyl, C
1-C
6Haloalkyl, C
1-C
6Alkoxyl group, C
1-C
6Halogenated alkoxy, C
1-C
6Alkylthio, C
1-C
6Alkyl sulphonyl, C
1-C
3Alkoxy carbonyl, C
1-C
3Alkoxy carbonyl C
1-C
3Alkyl or amino;
R
1Be selected from hydrogen, chlorine, bromine, cyano group, nitro, C
1-C
3Alkyl, C
1-C
3Alkoxyl group, C
1-C
3Alkoxy carbonyl, C
1-C
3Alkoxy carbonyl C
1-C
3Alkyl;
N is selected from 1～5;
M is selected from Na, K, Ca, Cu, Zn or ammonium salt.
Further preferred compound is: in the general formula (I)～(III)
R is selected from hydrogen, chlorine, bromine, fluorine, cyano group, nitro, C
1-C
3Alkyl or C
1-C
3Alkoxyl group;
R
1Be selected from hydrogen or C
1-C
3Alkyl;
N is selected from 1～3.
In the definition of the compound that provides above (I)～(III), compile the following substituting group of used term general proxy:
Halogen: refer to fluorine, chlorine, bromine and iodine.
Alkyl: straight or branched alkyl, for example methyl, ethyl, propyl group, sec.-propyl and the tertiary butyl.
Haloalkyl: the straight or branched alkyl, the hydrogen atom on these alkyl can partly or entirely be replaced by halogen atom, for example, haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl.
Alkoxyl group: the straight or branched alkyl is connected on the structure through the Sauerstoffatom key.
Halogenated alkoxy: the straight or branched alkoxyl group, the hydrogen atom on these alkoxyl groups can partly or entirely be replaced by halogen atom.For example, halogenated alkoxy such as chlorine methoxyl group, dichloro methoxyl group, trichlorine methoxyl group, fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, chlorine fluorine methoxyl group.
Alkynyl: straight or branched also can have triple bond on any position, for example ethynyl, propargyl.Substituted alkynyl comprises the sweet-smelling alkynyl of any replacement.
Ammonium salt: organic ammonium salt and inorganic ammonium salt.Organic amine refers to triethylamine, pyridine etc.
The indication heteroaryl is to contain one or more N, O, the heteroatomic 5 yuan of rings of S or 6 yuan of rings among the present invention.For example pyridine, furans, pyrimidine.
Because general formula (I), (II), (III) compound are known mostly, therefore can change the preparation method who is provided when the platform thing discloses first and obtain needed purpose product according to this.
Summary is got up, and general formula of the present invention (I) compound can prepare by the method shown in the following reaction:
In appropriate solvent, in the presence of the suitable alkali (also can without alkali), general formula (IV) and oxammonium hydrochloride reaction handle promptly getting the purpose product.
Compound shown in the general formula (IV) can be commercial, also can prepare according to reported method such as known references such as US3781438.
The optional tetrahydrofuran (THF) freely of appropriate solvent, acetonitrile, toluene, dimethylbenzene, benzene, N, dinethylformamide, methyl alcohol or ethanol etc.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, yellow soda ash, salt of wormwood, sodium bicarbonate, triethylamine, pyridine or sodium hydride etc.
Reaction is carried out to the solvent boiling point temperature range in room temperature usually, and suitable temperature of reaction is 20～100 ℃.
Reaction times is 30 minutes to 20 hours, common 1～10 hour.
General formula (I) and compound (II) are tautomers, and the compound of general formula (III) can be by general formula (I) and (II) compound and suitable alkali reaction make.The optional sodium methylate freely of suitable alkali, sodium ethylate, potassium hydroxide, sodium hydroxide, calcium hydroxide, triethylamine, pyridine or sodium hydride etc.
General formula (I) and (II) compound also can form complex compound with suitable salt such as mantoquita (copper sulfate etc.), zinc salt (as zinc chloride etc.).
Can the present invention be described with the compound of listing in the following Table I, but not limit the present invention.
Table 1
| Numbering | R n | R | Fusing point ℃ |
| 1 | H | H | 145-147 |
| 2 | 2-Cl | H | |
| 3 | 3-Cl | H | 101-103 |
| 4 | 4-Cl | H | 162-166 |
| 5 | 2-Br | H | |
| 6 | 3-Br | H | |
| 7 | 4-Br | H | 173-178 |
| 8 | 2-F | H | |
| 9 | 3-F | H | |
| 10 | 4-F | H | 134-136 |
| 11 | 2-CH 3 | H | 94-94.5 |
| 12 | 3-CH 3 | ||
| 13 | 4-CH 3 | H | 135-136 |
| 14 | 4-C 2H 5 | H | 83-84 |
| 15 | 4-C 3H 7 | H | 99-100 |
| 16 | 3-CF 3 | H | |
| 17 | 4-CF 3 | H | |
| 18 | 4-NO 2 | H | 246-248 |
| 19 | 4-CH 3S | H |
| 20 | 2-OCH 3 | H | |
| 21 | 3-OCH 3 | H | |
| 22 | 4-OCH 3 | H | |
| 23 | 4-OC 2H 5 | H | 1355-136 |
| 24 | 4-OCH 2CF 3 | H | |
| 25 | 3，5-Cl 2 | H | |
| 26 | 2，4-Cl 2 | H | |
| 27 | 3，4-Cl 2 | H | 129-131 |
| 28 | 2，4-Cl 2-5-F | H | |
| 29 | 3，4-(OCH 3) 2 | H | |
| 30 | 3，4-Cl 2 | H | |
| 31 | 3，5-Cl 2 | H | |
| 32 | 4-Ph | H | |
| 33 | 4-(4-Cl-Ph) | H | |
| 37 | 2，6-Cl 2 | H | |
| 38 | 2，4-(CH 3) 2 | H | 128-129 |
| 39 | 4-CN | H | 137-141 |
| 40 | 2-Cl | CH 3 | |
| 41 | 4-Cl | CH 3 | 208-210 |
| 42 | 4-Br | CH 3 | |
| 43 | 4-F | CH 3 | |
| 44 | 2-CH 3 | CH3 | |
| 45 | 3-CH 3 | CH 3 | |
| 46 | 4-CH 3 | CH 3 | |
| 47 | 4-C 2H 5 | CH 3 | |
| 48 | 4-C 3H 7 | CH 3 | |
| 49 | 3-CF 3 | CH 3 | |
| 50 | 4-CF 3 | CH 3 | |
| 51 | 4-NO 2 | CH 3 | |
| 52 | 4-CH 3S | CH 3 | |
| 53 | 2-OCH 3 | CH 3 | |
| 54 | 3-OCH 3 | CH 3 | |
| 55 | 4-OCH 3 | CH 3 | |
| 56 | 4-OC 2H 5 | CH 3 | |
| 57 | 4-OCH 2CF 3 | CH 3 | |
| 58 | 3，5-Cl 2 | CH 3 | |
| 59 | 2，4-Cl 2 | CH 3 | |
| 60 | 3，4-Cl 2 | CH 3 | |
| 61 | 2，4-Cl 2-5-F | CH 3 | |
| 62 | 3，4-Cl 2 | CH 3 | |
| 63 | 3，5-Cl 2 | CH 3 | |
| 64 | 4-Ph- | CH 3 | |
| 65 | 4-(4-Cl-Ph) | CH 3 |
Because the present invention has found that first the De isoxazole compounds has excellent fungicidal activity shown in general formula (I), (II), (III), they have systemic activity and can be used as the blade face and soil fungicides, therefore this compounds can be applied in the disease on the various crops of control, be particularly suitable for preventing and treating the following plants disease: downy mildew of garpe, rice sheath blight disease, rice blast, early blight of tomato, tomato late blight, wheat rust, speckled leaf blotch, wheat powdery mildew, powdery mildew of cucumber, cucumber downy mildew, gray mold of cucumber etc.
The present invention also provides a kind of fungicidal composition, contains general formula (I)～(III) compound with fungicidal activity in the composition, and the weight percentage of active ingredient is 0.1-99% in the composition.
The present invention also provides preparation of compositions method as defined above: the compound of general formula (I)～(III) is mixed with carrier.This composition can contain the mixture of simplification compound of the present invention or several compounds.
Carrier system in the present composition satisfies the material of following condition: being convenient to be applied to pending site after it and activeconstituents are prepared, for example can be plant, seed or soil; Perhaps help storing, transport or operation.Carrier can be solid or liquid, comprises the material that is generally gas but has been compressed into liquid, and used carrier all can use in the preparation fungicidal composition usually.
Suitable solid carrier comprises natural and synthetic clay and silicate, for example diatomite, talcum, attapulgite, pure aluminium silicate (kaolin), montmorillonite and mica; Lime carbonate; Calcium sulfate; Ammonium sulfate; Synthetic silicon oxide and synthetic calcium silicate or pure aluminium silicate; Element such as carbon and sulphur; Natural and synthetic resin such as coumarone resin, polyvinyl chloride and styrene polymer and multipolymer; Solid polystream phenol; Pitch; Wax such as beeswax, paraffin.
Suitable liquid vehicle comprises water; Alcohol is as Virahol and ethanol; Ketone such as acetone, methyl ethyl ketone, methyl isopropyl Ketone, cyclohexyl ketone; Ether; Aromatic hydrocarbons such as benzene,toluene,xylene; Petroleum fractions such as kerosene and mineral oil; Hydrochloric ether such as tetracol phenixin, tetrachloroethylene and trieline.Usually, these mixtures of liquids also are suitable.
Fungicidal composition is processed into the form of enriched material usually and is used for transportation with this, by the user it is diluted before using.Having of a spot of supporting surfactant helps dilution.Like this, according to having preferably tensio-active agent of a kind of carrier in the composition of the present invention at least.For example composition can contain at least two kinds of carriers, and wherein at least a is tensio-active agent.
Tensio-active agent can be emulsifying agent, dispersion agent or wetting agent; It can be non-ionic or the ionic tensio-active agent.The example of suitable tensio-active agent comprises the sodium salt or the calcium salt of polyacrylic acid and lignosulfonic acid; Contain the lipid acid of at least 12 carbon atoms or the condenses of aliphatic amide or acid amides and oxyethane and/or propylene oxide in the molecule.The condenses of glycol, sorbyl alcohol, sucrose or pentaerythritol fatty ester and these esters and oxyethane and/or propylene oxide; Fatty Alcohol(C12-C14 and C12-C18) or alkylphenol such as paraoctyl phenol or to the condenses of octyl group cresylol and oxyethane and/or propylene oxide; The vitriol of these condensation products and sulfonate; In molecule, contain the sulfuric acid of 10 carbon atoms or the basic metal or the alkaline earth salt of sulphonate at least, particular certain cancers, sulfuric acid laurate sodium for example, the secondary alkyl ester sodium of sulfuric acid, the sulfonated castor oil sodium salt, alkyl aryl sulfonic acid ester sodium is as pelopon A.
Composition of the present invention can be made multiple formulation according to ordinary method, for example wettable powder, pulvis, granule and solution, emulsible enriching agent, emulsion, suspension enriching agent, aerosol and smoke substance.Wettable powder contains 25,50 or 75% weight activeconstituents usually, and usually except that solid inert carrier, also contains the dispersion agent of 3-10% weight, and if needs to add stablizer and/or other additive such as the permeate agent or the tackiness agent of 0-10% weight.Pulvis may be molded to the pulvis enriching agent that has the composition similar to wettable powder but do not have dispersion agent usually, further with the solid carrier dilution, is contained the composition of 0.5-10% weight active ingredient usually again.Granula is prepared into usually has 10 to 100 order (1.676-0.152mm) sizes, and available agglomerating or implantttion technique preparation.Usually granula contains the activeconstituents of 0.5-75% weight and 0-10% weight additive such as stablizer, tensio-active agent, slowly-releasing modifying agent.So-called " dry powder can flow " is by the relatively little granulometric composition with relative high density activeconstituents.Outside but emulsion concentrate desolventizes, when needs, contain cosolvent usually, 1-50%W/V activeconstituents, other additives of 2-20%W/V emulsifying agent and 0-20%W/V such as stablizer, permeate agent and corrosion inhibitor.The suspension enriching agent contains the activeconstituents of 10-75% weight, the dispersion agent of 0.5-15% weight, other additive such as defoamer, corrosion inhibitor, stablizer, permeate agent and the tackiness agent of 0.1-10% weight usually.
Water dispersant and emulsion, for example by dilute with water according to the composition that wettable powder of the present invention or enriched material obtain, also list the scope of the invention in.Said emulsion can have water-in-oil or two types of oil-in-water.
By in composition, adding other one or more sterilant, make it have the more activity of wide spectrum than independent general formula (I)～(III) compound.In addition, but the fungicidal activity of other sterilant mutual-through type (I) compounds has synergism.Also general formula (I)～(III) compound and other sterilants can be used with, or use with another kind of sterilant and other sterilants simultaneously.
Embodiment
Below concrete example can further specify the present invention.
Synthetic embodiment
Example 1: the preparation method of compound 1
At room temperature, with 51 gram ethyl benzoylacetates, 33.1 gram oxammonium hydrochlorides reflux stirring reaction 5 hours in 400 milliliters of ethanol, cooling has solid to separate out, and filters, and methyl alcohol washes twice, wash twice to such an extent that title compound 20.6 restrains; Concentrated target compound 6.5 grams of getting back of filtrate.Altogether 27.1 gram products.
Nuclear magnetic data (
1H NMR, 300MHz, interior mark TMS, solvent DMSO) as follows:
δppm 7.46(3H，m)，7.70(2H，m)。
Example 2: the preparation method of compound 13
At room temperature, 25.5 gram 4-chlorobenzoyl ethyl acetate are dissolved in 125 milliliters of ethanol, 10.3 the gram oxammonium hydrochloride is dissolved in 20 ml waters, mixes the back to wherein adding 2.5 gram sodium hydroxide, the adularescent solid generates, stirred overnight at room temperature, pour in 500 milliliters of frozen water solid filtering, washing into, drying gets product 10 grams; Filtrate and washing lotion extract with benzene, concentrate after drying, again solid (target compound) 5 grams.Altogether 15 gram products.
Nuclear magnetic data (
1H NMR, 300MHz, interior mark TMS, solvent DMSO) as follows:
δppm 2.39(3H，s)，7.28(2H，m)，7.58(2H，m)。
Other compounds can be synthetic with reference to aforesaid method.
The nuclear magnetic data of part of compounds (
1H NMR, 300MHz, interior mark TMS, solvent DMSO) as follows:
Compound 4: δ ppm 7.53 (2H, m), 7.74 (2H, m).
Compound 18: δ ppm 7.80 (2H, m), 8.19 (2H, m).
Be metered into behind the active compound folding hundred in the example of formulations prescription.
Example 3 60% wettable powders
Compound 1 60% (weight)
Dodecyl sodium naphthalene sulfonate 2% (weight)
Sodium lignosulfonate 9% (weight)
Kaolin complements to 100% (weight)
Each component (being solid) mixes, and pulverizes in pulverizer, reaches standard up to particle.
Example 4 30% aq suspensions
Compound 4 30% (weight)
Dodecyl sodium naphthalene sulfonate 4% (weight)
Hemicellulose 2% (weight)
Propylene oxide 8% (weight)
Water complements to 100% (weight)
Compound 25 is pulverized in (1mm pearl) in ball mill with 80% and the dodecyl sodium naphthalene sulfonate that should add the water yield.Other components dissolved stirs other component of adding then in remaining water.
Example 5 25% suspension-emulsion enriched materials
Compound 13 25% (weight)
Dodecyl alcohol polyoxyethylene glycol phosphoric acid ester (emulsifying agent 1) 4% (weight)
Oxyethyl group tri-glyceride (emulsifying agent 2) 2% (weight)
Calcium dodecylbenzene sulphonate (emulsifying agent 3) 1.5% (weight)
The epoxy first and second alkane epoxy propane copolymers (dispersion agent) 2.5% (weight)
Pimelinketone (solvent 1) 30% (weight)
Alkylaryl cut (boiling point＞200 ℃) (solvent 2) complements to 100% (weight)
Compound 12 is dissolved in the solvent (should add hold metering 80%), adds emulsifying agent and dispersion agent then, and mixture is thoroughly stirred.Mixture is pulverized in ball mill (1mm pearl), adds remaining solvent then.
Biological activity determination
Example 6 fungicidal activities are measured
With The compounds of this invention the various fungus diseases of plant are tested.The method of test is as follows:
Adopt the potted plant measuring method of live body.The former medicinal small amount of acetone dissolving of testing compound is diluted to required concentration with the water that contains 0.1% tween 80.Spray pesticide carries out the disease inoculation after 24 hours to plant examination material.After the inoculation, plant is placed in the fixed temperature and humidity incubator, makes to infect and continue, wait to contrast abundant morbidity back (being generally week age) and carry out assessment surveys.
The partial test result is as follows:
During 400ppm, compound 18 grades to gray mold of cucumber (Botrytis cinerea) and rice blast preventive effect greater than 100%.
During 400ppm, compound 1,18,41 etc. are 100% to the preventive effect of cucumber downy mildew (Pseudoperonospora cubenis), and preventive effects such as compound 4,7,10,11,13,14,23,38,39 reach more than 80%.
During 400ppm, compound 1 grade is 100% to the preventive effect of wheat powdery mildew (BLumeria graminis), and preventive effects such as compound 18 reach more than 80%.
During 50ppm, compound 1 grade is 100% to the preventive effect of wheat powdery mildew and cucumber downy mildew.
Claims (5)
1. the conduct of De isoxazole compounds shown in the general formula (I)～(III) prevents and treats the application of the sterilant of crop pest:
In the formula:
R is selected from hydrogen, halogen, cyano group, nitro, C
1-C
12Alkyl, C
2-C
12Thiazolinyl, C
2-C
12Alkynyl, C
1-C
12Haloalkyl, C
1-C
12Alkoxyl group, C
1-C
12Halogenated alkoxy, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl, C
1-C
12Alkoxy carbonyl, C
1-C
12Alkoxy carbonyl C
1-C
12Alkyl, amino;
R
1Be selected from hydrogen, halogen, cyano group, nitro, C
1-C
12Alkyl, C
1-C
12Alkoxyl group, C
1-C
12Alkoxy carbonyl or C
1-C
12Alkoxy carbonyl C
1-C
12Alkyl;
N is selected from 1～5;
M is selected from basic metal, alkaline-earth metal.
2. the application of isoxazole compounds according to claim 1 is characterized in that: in the general formula (I)～(III)
R is selected from hydrogen, halogen, cyano group, nitro, C
1-C
6Alkyl, C
2-C
6Thiazolinyl, C
2-C
6Alkynyl, C
1-C
6Haloalkyl, C
1-C
6Alkoxyl group, C
1-C
6Halogenated alkoxy, C
1-C
6Alkylthio, C
1-C
6Alkyl sulphonyl, C
1-C
6Alkoxy carbonyl, C
1-C
6Alkoxy carbonyl C
1-C
6Alkyl, amino;
R
1Be selected from hydrogen, halogen, cyano group, nitro, C
1-C
6Alkyl, C
1-C
6Alkoxyl group, C
1-C
6Alkoxy carbonyl, C
1-C
6Alkoxy carbonyl C
1-C
6Alkyl;
N is selected from 1～5;
M is selected from basic metal, alkaline-earth metal.
3. the application of isoxazole compounds according to claim 2 is characterized in that: in the general formula (I)～(III)
R is selected from hydrogen, chlorine, bromine, fluorine, cyano group, nitro, C
1-C
3Alkyl, C
1-C
6Haloalkyl, C
1-C
6Alkoxyl group, C
1-C
6Halogenated alkoxy, C
1-C
6Alkylthio, C
1-C
6Alkyl sulphonyl, C
1-C
3Alkoxy carbonyl, C
1-C
3Alkoxy carbonyl C
1-C
3Alkyl or amino;
R
1Be selected from hydrogen, chlorine, bromine, cyano group, nitro, C
1-C
3Alkyl, C
1-C
3Alkoxyl group, C
1-C
3Alkoxy carbonyl, C
1-C
3Alkoxy carbonyl C
1-C
3Alkyl;
N is selected from 1～5;
M is selected from Na, K, Ca.
4. the application of isoxazole compounds according to claim 3 is characterized in that: in the general formula (I)～(II)
R is selected from hydrogen, chlorine, bromine, fluorine, cyano group, nitro, C
1-C
3Alkyl or C
1-C
3Alkoxyl group;
R
1Be selected from hydrogen or C
1-C
3Alkyl;
N is selected from 1～3.
5. fungicidal composition, it is characterized in that: contain general formula (I)～(III) compound of preventing and treating the crop pest fungicidal activity that has as claimed in claim 1 in the composition, the weight percentage of active ingredient is 0.1-99% in the composition.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100471528A CN100410244C (en) | 2005-09-08 | 2005-09-08 | Application of isoxazole compounds as bactericide |
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|---|---|---|---|
| CNB2005100471528A CN100410244C (en) | 2005-09-08 | 2005-09-08 | Application of isoxazole compounds as bactericide |
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| CN100410244C true CN100410244C (en) | 2008-08-13 |
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|---|---|---|---|---|
| GB0823002D0 (en) * | 2008-12-17 | 2009-01-28 | Syngenta Participations Ag | Isoxazoles derivatives with plant growth regulating properties |
| CN102516189B (en) * | 2011-12-06 | 2014-04-09 | 西北农林科技大学 | Oxazole organic copper compound, and preparation method and preparation thereof and purpose thereof in control of agricultural plant disease |
| CN102516190B (en) * | 2011-12-06 | 2014-04-09 | 西北农林科技大学 | Oxazolyl quinoline organic copper compound, preparation method of oxazolyl quinoline organic copper compound, oxazolyl quinoline organic copper compound agent, and use of oxazolyl quinoline organic copper compound in prevention and treatment of crop diseases |
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| GB1009801A (en) * | 1961-07-28 | 1965-11-10 | Ici Ltd | Isoxazole derivatives and fungicidal compositions containing them |
| US3370064A (en) * | 1960-11-02 | 1968-02-20 | Ici Ltd | Certain 4-(chlorophenylhydrazono)-2-isoxazolin-5-ones |
| CN1329807A (en) * | 1998-12-08 | 2002-01-02 | 艾利森电话股份有限公司 | Arrangement for establishing connections through network |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3370064A (en) * | 1960-11-02 | 1968-02-20 | Ici Ltd | Certain 4-(chlorophenylhydrazono)-2-isoxazolin-5-ones |
| GB1009801A (en) * | 1961-07-28 | 1965-11-10 | Ici Ltd | Isoxazole derivatives and fungicidal compositions containing them |
| CN1329807A (en) * | 1998-12-08 | 2002-01-02 | 艾利森电话股份有限公司 | Arrangement for establishing connections through network |
Also Published As
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|---|---|
| CN1927847A (en) | 2007-03-14 |
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