CN1824648A - Indene substituted oximinoether kind bactericide and insecticide - Google Patents
Indene substituted oximinoether kind bactericide and insecticide Download PDFInfo
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Abstract
The present invention discloses a kind of indene substituted oximinoether fungicide and insecticide and its preparation method. Said invention also provides its general formula. The invented compound not only is a good fungicide, but also is a good insecticide for effectively controlling various plant diseases and killing various injurious pests.
Description
Technical field
The invention belongs to pesticide sterilizing, sterilant technical field.Relate to class indene substituted oximinoether kind compound and preparation method thereof, contain the sterilizing insecticide of indene substituted oximinoether kind compound.
Background technology
1999, U.S.'s ROHM AND HAAS (ROHM AND HASS) company reported phenyl propenylidene oximinoether kind bactericide, sterilant, and the patent No. is: EP936213, and its structural formula is as follows:
It is reported that the compound of these unsaturated oxime ether structures has broad spectrum of activity, can be used for preventing on various crops by multiple fungus-caused diseases such as Phycomycetes, Oomycete, Ascomycetes and deuteromycetes.
2000, U.S.'s ROHM AND HAAS (ROHM AND HASS) company reported that again a class aryl rings propyl substituted oximinoether kind bactericide agent patent No. is: US6063956, and its structural formula is as follows:
2002, LG-DOW benefit farming (DOW AGROSCIENCES) company also reported the agent of another kind of aryl rings propyl substituted oximinoether kind bactericide, and the patent No. is: WO2002046142, and its structural formula is as follows:
Back two series bactericidal agents have replaced the aryl propenylidene of disclosed compound among the EP936213 with the aryl rings propyl, it is reported that this compounds has the broad-spectrum sterilization activity equally, wheat leaf rust, wheat powdery mildew, tomato late blight, rice blast and other plurality of plant diseases are all had good preventive effect.
Summary of the invention
The objective of the invention is to replace aryl rings propyl or aryl propenylidene, develop high-efficiency broad spectrum sterilization, the sterilant of a class formation novelty with the indenes substituting group.
The present invention relates to can be used as the indene substituted oximinoether kind derivative of sterilization, sterilant, their preparation method and contain these compound compositions.
The invention provides indene substituted oximinoether kind compound, even and find that such compound has very high biological activity thereby still can obtain the good sterilization effect under very low dosage with general formula I.
Wherein:
R
1Be hydrogen, halogen, C
1-C
4Alkyl or C
1-C
4Alkoxyl group;
R
2Be hydrogen, halogen, C
1-C
4Alkyl or C
1-C
4Alkoxyl group;
R
3Be hydrogen, C
1-C
4Alkyl, C
3-C
6Cycloalkyl, phenyl or substituted-phenyl;
Q is selected from one of group as follows:
X is O or NH.
The compound that embodiment preferred is a general formula I, wherein a R of the present invention
1Be hydrogen, fluorine, chlorine, C
1-C
4Alkyl or C
1-C
4Alkoxyl group; R
2Be hydrogen, fluorine, chlorine, C
1-C
4Alkyl or C
1-C
4Alkoxyl group; R
3Be CH
3Q is selected from Q
1, Q
2, one of group.
Compound of the present invention can be prepared by following method:
General formula I-Q
1, I-Q
2Compound can prepare like this: the compound of the oxime shown in the general formula I I and general formula III or general formula I V is added appropriate solvent, add suitable alkali, reacted 4-10 hour down at 80 ℃.
Preferred solvent is N, dinethylformamide or acetonitrile.
Preferred alkali is salt of wormwood or yellow soda ash.
General formula I-Q
3Compound can be by general formula I-Q
2Compound and aqueous methylamine solution reaction and obtain at an easy rate.
The compound of general formula I I can prepare like this: with N, dinethylformamide is a solvent, is catalyzer with the palladium, add an amount of alkali, phase-transfer catalyst, lithium chloride is at the 50-120 ℃ of halogen-substituted formaldehyde in following ortho position and derivative and vinylcarbinol derivative generation 2-carbonyl substituted indene derivative.The synthetic 2-of institute carbonyl substituted indene derivative and oxammonium hydrochloride in the presence of alkali, in aqueous ethanolic solution backflow 1-4 hour, can be obtained the oxime among the general formula I I.
Narrated methyl acrylate base synthetic for the compound of the general formula III of (E) configuration among US4723034, US5554578, the EP203606.
WO200246142, US5650434 have narrated the compound of general formula I V.
Be the concrete structure formula of the part of compounds of the present invention below, be used for further specifying the present invention, but do not mean that restriction the present invention with general formula I.
Part of compounds physical properties in the general formula I,
1H NMR (CDCl
3, 300MHz), IR (smear) data are as follows:
IS-1: faint yellow oily thing
1H NMR (CDCl
3, 300MHz) 2.15 (3H, s), 3.67 (2H, s), 3.69 (3H, s), 3.81 (3H, s), 5.11 (2H, s), 7.02 (1H, s), 7.14-7.18 (1H, m), 7.19-7.22 (1H, m), 7.30-7.42 (5H, m), 7.50-7.53 (1H, m), 7.59 (1H, s).IR？max(cm
-1)2950，1710，1635，1435，1255，1130，1020，760，720。
IS-2: yellow oil
1H NMR (CDCl
3, 300MHz) 2.58 (3H, s), 3.62 (2H, d, J=8.4Hz), 3.69 (3H, s), 3.81 (3H, s), 5.12 (2H, s), 6.94 (1H, s), 7.29-7.36 (4H, m), 7.46 (1H, d, J=7.8), 7.50 (1H, m), 7.61 (1H, m), 7.95 (1H, d, J=7.8).IR？max(cm
-1)2950，1710，1635，1470，1435，1250，1115，870，765。
IS-3: yellow oil
1H NMR (CDCl
3, 300MHz) 2.18 (3H, s), 3.64 (2H, s), 3.77 (3H, s), 3.79 (3H, s), 5.25 (2H, s), 7.03 (1H, s), 7.16-7.28 (2H, m), 7.35-7.40 (5H, m), 7.54-7.57 (1H, m).
IS-4: pale brown look oily matter
1H NMR (CDCl
3, 300MHz) 2.17 (3H, s), 3.61 (2H, d, J=8.7Hz), 3.77 (3H, s), 3.79 (3H, s), 5.26 (2H, s), 6.84-6.96 (2H, m), 7.01-7.11 (1H, m), and 7.24-7.31 (1H, m), 7.34-7.39 (3H, m), 7.52-7.60 (1H, m).IR？max(cm
-1)2940，1740，1620，1470，1440，1360，1225，1095，1030，870，765。
IS-5: yellow oil
1H NMR (CDCl
3, 300MHz) 2.19 (3H, s), 2.81 (3H, s), 3.59 (2H, s), 3.68 (3H, s), 5.31 (2H, s), 7.14-7.25 (3H, m), 7.30-7.40 (5H, m), 7.52-7.55 (1H, m).
IS-6: pale brown look oily matter
1H NMR (CDCl
3, 300MHz) 2.17 (3H, s), 2.89 (3H, s), 3.60 (2H, d, J=9.0Hz), 3.70 (3H, s), 5.31 (2H, s), 6.00 (1H, s), 6.83-6.96 (2H, m), 7.01-7.11 (1H, m), 7.26-7.34 (4H, m), 7.51-7.54 (1H, m).IR？max(cm
-1)3360，1680，1520，1470，1225，1020，870，765。
The compound of general formula I of the present invention is effective sterilant.These compounds have systemic activity and can be used as the blade face and soil fungicides.Plurality of plant diseases be can prevent and treat effectively, barley and wheat powdery mildew, powdery mildew of cucumber, uncinula necator, apple mildew, cucumber downy mildew, downy mildew of garpe etc. for example prevented and treated.Be particularly suitable for preventing and treating wheat powdery mildew and cucumber downy mildew.
The compound of general formula I of the present invention is the effective insecticidal agent, and mythimna separata, small cabbage moth, black peach aphid, carmine spider mite, culex pipiens pollens are all had good preventive effect, is particularly suitable for the integrated control to insect.
The present invention also provides a kind of sterilization, insect-killing composition and preparation method thereof.Said composition is an active ingredient with the simplification compound of general formula I or the mixture of several compounds, and the compound of the general formula I that its preparation method is mixes with at least a carrier.The weight of active ingredient is 1-99% in the common composition of the present invention.
Effect of the present invention and benefit are:
At carrier is the material that satisfies 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, can use any used carrier in configuration desinsection, fungicidal composition usually.
The solid carrier that is fit to 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 or synthetic resin such as coumarone resin, polyvinyl chloride and styrene polymer and multipolymer; Solid polystream phenol; Pitch; Wax such as beeswax, paraffin.
The liquid vehicle that is fit to 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 fit to.
Sterilization, insect-killing composition are processed into spissated form usually and are used for transportation with this, by user it are diluted before using.Contain a spot of tensio-active agent in the composition and help 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 has two kinds of carriers at least, 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 the tensio-active agent that is fit to comprises polyacrylic acid and xylogen vitriolic sodium salt or calcium salt; Contain the lipid acid of at least 12 carbon atoms or the condenses of acid amides and oxyethane and/or propylene oxide in the molecule.The condenses of glycol, Sorbic Acid, 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 or to the condenses of octyl group cresylol and oxyethane and/or propylene oxide; The vitriol of these condensess and sulfonate; In molecule, contain the sulfuric acid of 10 carbon atoms or the alkaline earth salt of sulphonate at least, particular certain cancers, for example sodium lauryl sulfate, the secondary alkane ester of sulfuric acid sodium, sulfonated castor oil sodium salt, alkyl aryl sulfonic acid ester sodium, alkyl aryl sulfonic acid ester sodium is as sodium dodecylbenzene salt.
Sterilization of the present invention, insect-killing composition can be processed into multiple formulation as required, for example wettable powder, pulvis, granule and solution, the agent of emulsible agricultural institute, emulsion, suspension enriching agent, aerosol and smoke substance.Wettable powder contains the activeconstituents of 25,50 or 75% weight 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 additives 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 similar composition of wettable powder but do not have dispersion agent usually, further with the solid carrier dilution, is contained the composition of 0.5-10% taskwork component usually again.Pulvis is prepared into usually has 10 and 100 orders (1.676-0.152 millimeter) size, 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 " has the relatively little granulometric composition of relative high density activeconstituents again.Outside but emulsion concentrate desolventizes, when needs, contain cosolvent usually, 1-50%W/V activeconstituents, other additive of 2-20%W/V emulsifying agent and 2-20%W/V such as stablizer, permeate agent and corrosion inhibitor.The suspension thickner contains the activeconstituents of 10-75% weight usually.Other additives of the dispersion agent of 0.5-15% weight, 0.1-10% weight such as defoamer, corrosion inhibitor, stablizer, permeate agent and tackiness agent.
By in composition, adding other one or more sterilant, make it can have the more activity of wide spectrum than independent compound of Formula I.In addition, but the fungicidal activity of other sterilant mutual-through type I compound has synergism.Also general formula 1 compound and other sterilant can be used with, or use with another kind of sterilant and other sterilant simultaneously.The example that can be included in the Fungicidal compounds in the present composition has: cyanogen bacterium azoles, triadimefon, F-1991, derosal, Baijunling, king's ketone, Bordeaux mixture, fuberidazole, the hot salt of biguanides, hymexazol, Fujione, kasugamycin, zinc manganese ethylenebisdithiocarbamate, maneb, zineb, Polyoxin, propineb, thiophanate methyl, thiram, tridemorph, rare morpholide etc.
Can comprise Rogor, omethoate, Chlorpyrifos 94, chlorpyrifos_methyl, acephatemet, monocrotophos, Tiguvon, Volaton, triaxamate, Provado and pyrethroid such as fenvalerate, Fenvalerate, taufluvalinate, cyhalothrin etc. with the suitable sterilant of compound formation composition of the present invention.
Embodiment
Following example and living test are tested the result and be can be used to further specify the present invention, but do not mean that restriction the present invention.
The preparation of the compound of example 1 general formula I:
3-methoxyl group-2-[2-((1-(1H-indenes-2-yl) ethylidene) amino oxygen methyl) phenyl] methyl acrylate (IS-1) synthetic:
In 20 milliliters two-mouth bottle, add 1-(2-indenyl)-ethyl ketone oxime (0.3 gram, 1.75 mmoles) respectively, intermediate III (0.50 gram, 1.75 mmole), salt of wormwood (0.48 gram, 3.5 mmoles), 6 milliliters of acetonitriles, heating, induction stirring, temperature rise to 80 ℃ of backflows, the TLC detection reaction, stopped reaction after 5 hours.In reaction solution, add 20 ml waters, with 3 * 20 milliliters of ethyl acetate extractions.Use anhydrous magnesium sulfate drying, the decompression precipitation separates (ethyl acetate/petroleum ether=1/10) through silica gel column chromatography and gets product 0.37 gram, yield 54%.
N-methoxyl group-N-[2-((1-(1H-indenes-2-yl) ethylidene) amino oxygen methyl) phenyl] Urethylane (IS-3) synthetic
In 20 milliliters two-mouth bottle, add 1-(2-indenyl)-ethyl ketone oxime (0.26 gram, 1.5 millis rub) that respectively, N-2-2-bromomethylphenyl-N-methoxyl group Urethylane (intermediate compound IV, 0.52 gram, 1.8 mmoles), salt of wormwood (0.41 gram, 3 mmoles), 5 milliliters of acetonitriles, heating, induction stirring, temperature rises to 80 ℃ of backflows, and TLC follows the tracks of detection reaction, stopped reaction after 3.5 hours.In reaction solution, add 20 ml waters, with 3 * 20 milliliters of ethyl acetate extractions.Use anhydrous magnesium sulfate drying, the decompression precipitation separates (ethyl acetate/petroleum ether=1/10) through silica gel column chromatography and gets product 0.34 gram, yield 62%.
N-methoxyl group-N-[2-((1-(1H-indenes-2-yl) ethylidene) amino oxygen methyl) phenyl] carbamyl methylamine 1S-5 synthetic
In 20 milliliters two-mouth bottle, add N-methoxyl group-[2-[[[[1-(2-indenyl) ethylidene] amino respectively] the oxygen base] methyl] phenyl] Urethylane (0.18 gram, 0.5 mmole), methylamine (0.37 gram, 3 mmoles, 25% aqueous solution), 2 milliliters of methyl alcohol, heating, induction stirring, temperature rises to 80 ℃ of backflows, along with reaction is carried out, constantly add methylamine and methyl alcohol, to prevent volatilization, the TLC detection reaction, stopped reaction after 21 hours.In reaction solution, add 20 ml waters, with 3 * 20 milliliters of ethyl acetate extractions. use anhydrous magnesium sulfate drying, the decompression precipitation separates (ethyl acetate/petroleum ether=1/10) through silica gel column chromatography and gets product 0.16 gram, yield 87.9%.
The preparation of the compound of example 2 general formula I I:
Synthesizing of 1-(1H-indenes-2-yl) ethyl ketone
In 50 milliliters of two-mouth bottles, add 2-bromobenzaldehyde (0.56 gram, 3 mmoles) respectively, 3-butene-2-alcohol (0.26 gram, 3.6 mmoles), (34 milligrams of palladium, 0.15 mmole), sodium acetate (0.62 gram, 7.5 mmoles,) tetrabutylammonium chloride (1.67 grams, 6 mmoles), lithium chloride (0.26 gram, 6 mmoles).With reaction flask for several times, with the protection of nitrogen ball, in reaction flask, inject 30 milliliters of N then with needle tubing with nitrogen wash, dinethylformamide, reaction is 4 hours under 110 ℃, stopped reaction.Add 60 ml waters in reaction solution, with 3 * 60 milliliters of ethyl acetate extractions, anhydrous magnesium sulfate drying, the decompression precipitation separates (ethyl acetate/petroleum ether=1/5) through silica gel column chromatography, gets faint yellow solid 0.32 gram, yield 67%.
1H?NMR(CDCl
3，300MHz)2.48(3H，s)，3.65(2H，s)，7.32-7.37(2H，m)，7.48-7.55(2H，m)，7.62(1H，s)。IR？max(cm
-1)1650，1555，1460，1370，1335，1190，880，760，720。
Synthesizing of 1-(1H-indenes-2-yl)-ethyl ketone oxime
Difference 2-ethanoyl-indenes (0.47 gram, 3 mmoles) in 20 milliliters two-mouth bottle, oxammonium hydrochloride (0.31 gram, 4.5 mmoles), 10 milliliters of ethanol, heating, induction stirring refluxes TLC detection reaction, stopped reaction after 4 hours.In reaction solution, add 50 milliliters of 0.5N hydrochloric acid, with 2 * 50 milliliters of ethyl acetate extractions.Use anhydrous magnesium sulfate drying, the decompression precipitation separates (ethyl acetate/petroleum ether=1/4) through silica gel column chromatography, gets faint yellow solid 0.552 gram, yield 89.7%
1H?NMR(CDCl
3，300MHz)2.25(3H，s)，3.70(2H，s)，7.13(1H，s)，7.23-7.28(2H，m)，7.39-7.46(2H，m)。IR？max(cm
-1)3200-3400(br)，2390，1635，1010，930，850，755.715。
Other compound can be synthetic with reference to aforesaid method.
Formulation Example
Example 3 9% missible oil
10 parts of heavy Compound I S-1 are dissolved in the following mixture of 90 parts of weights: this mixture contains the oxyethane of 90 parts of heavy dimethylbenzene, 6 parts of heavy polyoxyethylene nonylphenol ethers, 2 parts of heavy calcium dodecylbenzene sulphonates and 2 parts of weights and the affixture (mol ratio 40/1) of Viscotrol C, preparation missible oil (active compound content is 9%).
Example 4 80% liquors
80 parts of (weight) Compound I S-3 are mixed with the N-Methyl pyrrolidone of 20 parts (weight), obtain being fit to the solution of using with small droplets form very (active compound content is 80%).
Biological activity determination
Example 5 fungicidal activities are measured
Compound with general formula I of the present invention is tested the various fungal diseases of plant.The program of test is as follows: plant is tried material carry out potted plant.The former medicinal small amount of N of testing compound, the dinethylformamide dissolving is diluted with water to required concentration, and preparation is diluted with water to required concentration.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 and infect to continue, carry out assessment surveys after waiting to contrast abundant morbidity.The most serious occurring degree (being worth as the basic survey standard with this usually) of " 0 " representative, the no any scab of " 100% " representative.Test result sees Table 1, table 2.
Table 1, part of compounds are to the cucumber downy mildew test result:
| Dosage (ppm) | Compound fungicidal activity (%) |
| IS-1 | IS-2 | IS-4 | IS-6 | BAS490F | |
| 50 | 100 | 100 | 95 | 95 | 90 |
| 12.5 | 98 | 65 | 80 | 85 | 20 |
Table 2, part of compounds are to the wheat powdery mildew test result:
| Dosage (ppm) | Compound fungicidal activity (%) | ||||||
| IS-1 | IS-2 | IS-3 | IS-4 | IS-5 | IS-6 | BAS490F | |
| 400 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
| 50 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
| 12.5 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
| 3.125 | 100 | 100 | 85 | 90 | 40 | 50 | 70 |
Annotate: the BAS490F structural formula is:
The test of example 6 insecticidal activities
Compound with general formula I of the present invention has carried out the insecticidal activity test simultaneously.Experimental technique: the mixed solvent of getting 2.5ml acetone/methanol (1: 1) joins in the weighing bottle that fills the 3mg new compound, stirring is fully dissolved it, adding 2.5ml contains the new compound solution 5ml that obtains 600mg/L after putting tap water, stirring of 1 ‰ tween 80s.Mythimna separata, small cabbage moth, black peach aphid and carmine spider mite adopt the airbrush spray method to handle, and spray pressure is 0.7kg/cm
2, spray amount 0.3ml, 2 repetitions are established in every processing.Mythimna separata and small cabbage moth are at first sprayed and handle blade (mythimna separata is used leaf of Semen Maydis, and small cabbage moth is used cabbage leaves), connect 5 larvas after blade dries in the shade.For cotten aphid and carmine spider mite, then directly cucumber leaves and the Kidney bean blade that target is arranged infected in the spraying processing.Culex pipiens pollens adopts immersion method to go to handle, and being about to soup has in the beaker of 20 larvas direct the adding.
Examination material after the processing moves to that (23-25 ℃, 40-60%R.H., L/D are 13h: 11h) in the standard observation ward.Lepidopterous larvae is handled the mortality ratio of back 3 days investigation examination worms, and black peach aphid, carmine spider mite and culex pipiens pollens carry out record according to examination worm mortality ratio to the insecticidal activity of compound in the mortality ratio of processing investigation examination in back 2 days worm.Test result sees Table 3.
Table 3, part of compounds desinsection test result (600ppm)
| Compound number | Compound insecticidal activity (%) | ||||
| Mythimna separata | Small cabbage moth | Black peach aphid | Carmine spider mite | Culex pipiens pollens | |
| IS-1 | 80 | 100 | 100 | 60 | 100 |
| IS-2 | 100 | 100 | 95 | 100 | 100 |
| IS-4 | 100 | 80 | 75 | 0 | 50 |
Claims (8)
1. the compound of general formula I:
Wherein:
R1 is hydrogen, halogen, C1-C4 alkyl or C1-C4 alkoxyl group;
R2 is hydrogen, halogen, C1-C4 alkyl or C1-C4 alkoxyl group;
R3 is hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, phenyl or substituted-phenyl;
Q is selected from one of group as follows:
X is O or NH.
2. the preparation method of compound of Formula I:
Intermediate II and intermediate Q3 or intermediate Q4 obtain the compound of general formula I in the presence of solvent and alkaline matter,
In the formula: R1, R2, R3, X have above-mentioned definition of giving, and L is a leavings group, are selected from chlorine, bromine or iodine;
Temperature of reaction is that room temperature extremely refluxes, and the reaction times is 0.5-24 hour;
Adopted solvent be selected from N, dinethylformamide, dimethyl sulfoxide (DMSO), acetonitrile or tetrahydrofuran (THF);
The alkali that is adopted is selected from sodium hydride, sodium methylate, sodium ethylate, sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood, sodium bicarbonate or saleratus.
3. preparation method according to claim 2 is characterized in that: temperature of reaction is 80 ℃, and the reaction times is 4-10 hour; The solvent that is adopted is selected from N, dinethylformamide or acetonitrile, and the alkali that is adopted is selected from yellow soda ash or salt of wormwood.
4. the compound of general formula I is in the application that prevents and treats on the crop pest.
5. purposes according to claim 4 is characterized in that: compound of Formula I is used to prevent and treat Powdery Mildew and oidium.
6. the compound in the claim 1 and other compounds with similar or complementary fungicidal activity or insecticidal activity are formed composition.
7. the compound in the claim 1 is formed Bactericide composition together as activeconstituents and the various carriers or the thinner that are used for sterilant, and the weight percentage of active ingredient is 1-99% in the composition.
8. the compound in the claim 1 is formed insecticides together as activeconstituents and the various carriers or the thinner that are used for sterilant, and the weight percentage of active ingredient is 1-99% in the composition.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103601716A (en) * | 2013-11-20 | 2014-02-26 | 厦门大学 | Benzothiophene substituted oxime ether compound and preparation method and application thereof |
| CN103980179A (en) * | 2014-05-29 | 2014-08-13 | 厦门大学 | Indole-substituted oxime ether compounds as well as preparation method and application thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103864662B (en) * | 2012-12-10 | 2016-04-06 | 南京农业大学 | Containing the methoxy-methyl acrylate compounds of pyrrolidine-diones, preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6063956A (en) * | 1999-01-27 | 2000-05-16 | Rohm And Haas Company | Aryl and heteroarylcyclopropyl oxime ethers and their use as fungicides and insecticides |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103601716A (en) * | 2013-11-20 | 2014-02-26 | 厦门大学 | Benzothiophene substituted oxime ether compound and preparation method and application thereof |
| CN103980179A (en) * | 2014-05-29 | 2014-08-13 | 厦门大学 | Indole-substituted oxime ether compounds as well as preparation method and application thereof |
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