CN1309897A - Unsaturated oximino ether bactericide - Google Patents

Unsaturated oximino ether bactericide Download PDF

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Publication number
CN1309897A
CN1309897A CN 00110143 CN00110143A CN1309897A CN 1309897 A CN1309897 A CN 1309897A CN 00110143 CN00110143 CN 00110143 CN 00110143 A CN00110143 A CN 00110143A CN 1309897 A CN1309897 A CN 1309897A
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compound
methyl
control compound
formula
control
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CN 00110143
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CN1114590C (en
Inventor
张立新
刘冬青
史蒂夫·H·塞伯
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Research Institute of Chemical Industry Co Ltd
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Abstract

The present invention relates to unsaturated oximino ether and its stereoisomer as fungicide compound. Compared with available unsaturated oximino ether, the present invention has high fungicidal activity.

Description

Unsaturated oximino ether bactericide
The invention belongs to disinfectant use in agriculture.
In the open CN1191670A of Chinese patent, reported bactericide with unsaturated oxime ether structure.The compound of these unsaturated oxime ether structures has broad spectrum of activity---can be used for preventing and treating on various crops by multiple fungus-caused diseases such as Phycomycetes, Oomycete, Ascomycetes and deuteromycetes.But we constantly bring forth new ideas the demand for development on modern agriculture and the gardening, develop the disinfectant use in agriculture that using dosage is littler, drug effect is more outstanding.
In order to obtain under littler dosage, just can control the active compound of various fungal diseases, present inventors have proceeded number of research projects on the basis of aforementioned invention, synthesize, filter out the have general formula compound of unsaturated oxime ether structure of (I).These compounds have the bactericidal activity of wide spectrum, compare with disclosed compound in the prior art, and they have higher bactericidal activity, have good preventive effect under lower dosage, thereby have finished the present invention.
The present invention relates to can be used as bactericide unsaturated oxime ether derivative, their preparation method and contain these compound compositions.
The invention provides the have general formula unsaturated oxime ether compound and the stereoisomer thereof of (I):
X in the formula 1-X 5Be selected from hydrogen, halogen, alkyl, alkoxyl, nitro, alkylhalide group.
Halogen comprises fluorine, chlorine, bromine and iodine.
In compound of the present invention, because carbon-to-carbon double bond is connected different substituting groups and can forms geometric isomer (representing different configurations with E and Z respectively) with the two keys of carbon-nitrogen, the present invention includes the mixture of E-isomer and Z type isomer and any ratio thereof.
Can the present invention be described with the compound in the following table (I), but not limit the present invention.
Table (I)
Numbering ????X 1 ????X 2 ????X 3 ????X 4 ????X 5
????1 ????2-Cl ????3-H ????4-H ????5H ????6-Cl
????2 ????2-Cl ????3-Cl ????4-H ????5H ????6-H
????3 ????2-Cl ????3-H ????4-Cl ????5-H ????6-H
????4 ????2-Cl ????3-H ????4-H ????5-Cl ????6-H
????5 ????2-H ????3-Cl ????4-Cl ????5-H ????6-H
????6 ????2-H ????3-Cl ????4-H ????5-Cl ????6-H
????7 ????2-Cl ????3-Cl ????4-Cl ????5-H ????6-H
????8 ????2-Cl ????3-Cl ????4-H ????5-Cl ????6-H
????9 ????2-Cl ????3-Cl ????4-H ????5-H ????6-Cl
????10 ????2-Cl ????3-H ????4-Cl ????5-Cl ????6-H
????11 ????2-Cl ????3-H ????4-Cl ????5-H ????6-Cl
????12 ????2-H ????3-Cl ????4-Cl ????5-Cl ????6-H
????13 ????2-Cl ????3-Cl ????4-Cl ????5-Cl ????6-H
????14 ????2-Cl ????3-Cl ????4-Cl ????5-H ????6-Cl
????15 ????2-Cl ????3-Cl ????4-H ????5-Cl ????6-Cl
????16 ????2-Cl ????3-Cl ????4-Cl ????5-Cl ????6-Cl
????17 ????2-F ????3-H ????4-H ????5H ????6-F
????18 ????2-F ????3-F ????4-H ????5H ????6-H
????19 ????2-F ????3-H ????4-F ????5-H ????6-H
????20 ????2-F ????3-H ????4-H ????5-F ????6-H
????21 ????2-H ????3-F ????4-F ????5-H ????6-H
????22 ????2-H ????3-F ????4-H ????5-F ????6-H
????23 ????2-Br ????3-H ????4-H ????5H ????6-Br
????24 ????2-Br ????3-Br ????4-H ????5H ????6-H
????25 ????2-Br ????3-H ????4-Br ????5-H ????6-H
????26 ????2-Br ????3-H ????4-H ????5-Br ????6-H
????27 ????2-H ????3-Br ????4-Br ????5-H ????6-H
????28 ????2-H ????3-Br ????4-H ????5-Br ????6-H
????29 ????2-Br ????3-Br ????4-Br ????5-H ????6-H
????30 ????2-Br ????3-Br ????4-H ????5-Br ????6-H
????31 ????2-Br ????3-Br ????4-H ????5-H ????6-Br
????32 ????2-Br ????3-H ????4-Br ????5-Br ????6-H
????33 ????2-Br ????3-H ????4-Br ????5-H ????6-Br
????34 ????2-H ????3-Br ????4-Br ????5-Br ????6-H
????35 ????2-Br ????3-Br ????4-Br ????5-Br ????6-H
????36 ????2-Br ????3-Br ????4-Br ????5-H ????6-Br
????37 ????2-Br ????3-Br ????4-H ????5-Br ????6-Br
????38 ????2-Br ????3-Br ????4-Br ????5-Br ????6-Br
????39 ????2-Cl ????3-H ????4-H ????5H ????6-F
????40 ????2-Cl ?????3-F ?????4-H ????5H ????6-H
????41 ????2-F ?????3-Cl ?????4-H ????5H ????6-H
????42 ????2-Cl ?????3-H ?????4-F ????5-H ????6-H
????43 ????2-F ?????3-H ?????4-Cl ????5-H ????6-H
????44 ????2-F ?????3-H ?????4-H ????5-Cl ????6-H
????45 ????2-Cl ?????3-H ?????4-H ????5-F ????6-H
????46 ????2-H ?????3-Cl ?????4-F ????5-H ????6-H
????47 ????2-H ?????3-F ?????4-Cl ????5-H ????6-H
????48 ????2-H ?????3-Cl ?????4-H ????5-F ????6-H
????49 ????2-F ?????3-Cl ?????4-Cl ????5-H ????6-H
????50 ????2-Cl ?????3-F ?????4-Cl ????5-H ????6-H
????51 ????2-Cl ?????3-Cl ?????4-F ????5-H ????6-H
????52 ????2-F ?????3-F ?????4-Cl ????5-H ????6-H
????53 ????2-Cl ?????3-F ?????4-F ????5-H ????6-H
????54 ????2-F ?????3-Cl ?????4-F ????5-H ????6-H
????55 ????2-F ?????3-F ?????4-F ????5-H ????6-H
????56 ????2-F ?????3-Cl ?????4-H ????5-Cl ????6-H
????57 ????2-Cl ?????3-F ?????4-H ????5-Cl ????6-H
????58 ????2-Cl ?????3-Cl ?????4-H ????5-F ????6-H
????59 ????2-F ?????3-F ?????4-H ????5-Cl ????6-H
????60 ????2-Cl ?????3-F ?????4-H ????5-F ????6-H
????61 ????2-F ?????3-Cl ?????4-H ????5-F ????6-H
????62 ????2-F ?????3-F ?????4-H ????5-F ????6-H
????63 ????2-F ?????3-Cl ?????4-H ????5-H ????6-Cl
????64 ????2-Cl ?????3-F ?????4-H ????5-H ????6-Cl
????65 ????2-Cl ?????3-Cl ?????4-H ????5-H ????6-F
????66 ????2-F ?????3-F ?????4-H ????5-H ????6-Cl
????67 ????2-F ?????3-Cl ?????4-H ????5-H ????6-F
????68 ????2-Cl ?????3-F ?????4-H ????5-H ????6-F
????69 ????2-F ?????3-F ?????4-H ????5-H ????6-F
????70 ????2-F ?????3-H ?????4-Cl ????5-Cl ????6-H
????71 ????2-Cl ?????3-H ?????4-F ????5-Cl ????6-H
????72 ????2-Cl ?????3-H ?????4-Cl ????5-F ????6-H
????73 ????2-F ?????3-H ?????4-F ????5-Cl ????6-H
????74 ????2-F ?????3-H ?????4-Cl ????5-F ????6-H
????75 ????2-Cl ?????3-H ?????4-F ????5-F ????6-H
????76 ????2-F ?????3-H ?????4-F ????5-F ????6-H
????77 ????2-F ?????3-H ?????4-Cl ????5-H ????6-Cl
????78 ????2-Cl ?????3-H ?????4-F ????5-H ????6-Cl
????79 ????2-F ?????3-H ?????4-F ????5-H ????6-Cl
????80 ????2-F ?????3-H ?????4-Cl ????5-H ????6-F
????81 ????2-F ?????3-H ?????4-F ????5-H ????6-F
????82 ????2-F ????3-F ?????4-H ????5-F ????6-F
????83 ????2-F ????3-F ?????4-F ????5-F ????6-F
????84 ????2-Cl ????3-H ?????4-H ????5H ????6-CH3
????85 ????2-CH3 ????3-H ?????4-Cl ????5-H ????6-Cl
????86 ????2-Cl ????3-H ?????4-CH3 ????5-H ????6-Cl
????87 ????2-CH3 ????3-H ?????4-CH3 ????5-H ????6-Cl
????88 ????2-CH3 ????3-H ?????4-Cl ????5-H ????6-CH3
????89 ????2-CH3 ????3-H ?????4-CH3 ????5-H ????6-CH3
????90 ????2-Br ????3-H ?????4-Cl ????5-H ????6-Cl
????91 ????2-Cl ????3-H ?????4-Br ????5-H ????6-Cl
????92 ????2-Br ????3-H ?????4-Br ????5-H ????6-Cl
????93 ????2-Br ????3-H ?????4-Cl ????5-H ????6-Br
????94 ????2-Br ????3-H ?????4-H ????5H ????6-F
????95 ????2-F ????3-H ?????4-Br ????5-H ????6-Br
????96 ????2-Br ????3-H ?????4-F ????5-H ????6-Br
????97 ????2-F ????3-H ?????4-F ????5-H ????6-Br
????98 ????2-F ????3-H ?????4-Br ????5-H ????6-F
????99 ????2-Cl ????3-H ?????4-H ????5H ????6-OCH3
????100 ????2-OCH3 ????3-H ?????4-Cl ????5-H ????6-Cl
????101 ????2-Cl ????3-H ?????4-OCH3 ????5-H ????6-Cl
????102 ????2-OCH3 ????3-H ?????4-OCH3 ????5-H ????6-Cl
????103 ????2-OCH3 ????3-H ?????4-Cl ????5-H ????6-OCH3
????104 ????2-Cl ????3-H ?????4-H ????5H ????6-NO2
????105 ????2-NO2 ????3-H ?????4-Cl ????5-H ????6-Cl
????106 ????2-Cl ????3-H ?????4-NO2 ????5-H ????6-Cl
????107 ????2-NO2 ????3-H ?????4-Cl ????5-H ????6-NO2
????108 ????2-Cl ????3-H ?????4-H ????5H ????6-CF3
????109 ????2-Cl ????3-H ?????4-CF3 ????5-H ????6-Cl
????110 ????2-Cl ????3-Cl ?????4-CF3 ????5-H ????6-CF3
????111 ????2-F ????3-H ?????4-H ????5H ????6-CF3
????112 ????2-Cl ????3-H ?????4-H ????5H ????6-I
The compound of general formula of the present invention (I) can prepare by the step shown in the following reaction equation.Wherein the definition of X is the same, and Z is a leaving group, as halogen (chlorine, bromine or iodine).
Figure A0011014300071
Figure A0011014300081
The compound of general formula (IV) can prepare like this: in appropriate solvent as dimethyl formamide, oxolane, acetone or butanone, handle the oxime shown in the general formula (III) with suitable alkali as sodium hydroxide, sodium methoxide or sodium hydride, add the compound of general formula (II) then.
The oxime of general formula (III) can be by corresponding α, beta unsaturated ketone and hydroxylamine hydrochloride in appropriate solvent (as methyl alcohol or ethanol), and reaction obtains to have suitable alkali (as sodium hydroxide or potash) to exist down.
Having narrated Z in the European patent application EP 254426 is the compound of the general formula (II) of bromine (E) configuration.
The compound of general formula (I) can be obtained easily by the compound and the methylamine water solution reaction of general formula (IV).
Compound of the present invention is more effective bactericide.They have systemic activity and can be used as the blade face and soil fungicides.Be particularly suitable for preventing and treating the following plants disease:
Rice blast (Pyricularia oryzae); Stripe rust of wheat (Puccinia striiformis), leaf rust (Puccinia recondita) and other rust; Big wheat yellow rust (Puccinia striiformis), leaf rust (Puccinia recandita) and other rust; Barley and wheat powdery mildew, powdery mildew of cucumber, apple mildew and grape powdery mildew.
Wheat sharp eyespot and glume blight (Septoria nodorum).Length on the cereal wriggle spore, the mouth spore is mould, Septoria is sick, caryosphere shell Pseudomonas disease, Pseudocercosporella herpotrichoides and Gaeumannomyces graminis.The mould genus of other tail spore on peanut Cercospora arachidicola and Cercosporidiumpersonata beet, soybean and the paddy is sick.Tomato, cucumber, grape grey mould (Botrytic cinerea).Hinge spore on the vegetables (as cucumber) belongs to sick.Anthracnose on the cucumber, apple scab, cucumber downy mildew, downy mildew of garpe, the epidemic disease on potato and the tomato is mould, other rhizoctonia on the Thanatephorus cucumeris on the paddy and other host such as wheat and barley, the vegetables.
The present invention also provides preparation of compositions method as defined above, and method is that the compound of general formula (I) and at least a carrier are mixed.This composition can contain the mixture of unification compound of the present invention or several compounds.
According to composition of the present invention, preferably contain from the active component of 1-99% weight.Carrier of the present invention is the material that satisfies following condition: being convenient to be applied to pending site after it and active component are prepared, for example can be plant, seed or soil; Perhaps help storing, transport or operation.Carrier can be solid or liquid, comprises being generally gas but being compressed into the material of liquid and can having used any usually used carrier in preparation desinsection, bactericidal composition.
Suitable solid carrier comprises natural and synthetic clay and silicate, for example diatomite, talcum, Attagel, alumina silicate (kaolin), montmorillonite and mica, calcium carbonate, calcium sulphate, ammonium sulfate; Synthetic silica and synthetic calcium silicate or alumina silicate; Element such as carbon and sulphur; Natural and synthetic resin such as cumarone resin, polyvinyl chloride and styrene polymer and copolymer; Solid polystream phenol; Pitch; Wax such as beeswax, paraffin.
Suitable liquid-carrier comprises water; Alcohol is as isopropyl alcohol and ethanol; Ketone such as acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK) and cyclohexyl ketone; Ether; Aromatic hydrocarbons such as benzene, toluene and dimethylbenzene; Petroleum distillate such as kerosene and mineral oil; Chlorohydrocarbon such as carbon tetrachloride, perchloroethylene and trichloroethanes.Usually, these mixtures of liquids also are suitable.
Desinsection, bactericidal composition usually before using with its dilution.Having of a spot of supporting surfactant helps dilution.In composition of the present invention, contain a kind of carrier at least, preferably make carrier with surfactant.For example composition can contain at least two kinds of carriers, and wherein at least a is surfactant.
Surfactant can be emulsifier, dispersant or wetting agent; It can be surfactant nonionic or ion.Suitable surfactant comprises the sodium salt or the calcium salt of polyacrylic acid and lignin sulfonic acid; Contain the fatty acid of at least 12 carbon atoms or the condensation product of fatty amine or acid amides and oxirane and/or expoxy propane in the molecule; Glycol, sorbierite, the condensation product of sucrose or pentaerythritol fatty ester and these esters and oxirane and/or expoxy propane; Fatty alcohol or alkylphenol such as paraoctyl phenol or to the condensation product of octyl group cresols and oxirane and/or expoxy propane; The sulphate of these condensation products or sulfonate; In molecule, contain the sulfuric acid of at least 10 carbon atoms or the alkali metal or the alkali salt of sulphonic acid ester, particular certain cancers; Sodium lauryl sulfate for example, the secondary Arrcostab sodium of sulfuric acid, sulfonated castor oil sodium salt, alkyl aryl sulfonic acid ester sodium such as pelopon A.
The example of composition of the present invention is wetting powder, pulvis, granule and solution, emulsible concentrating agents, emulsion, suspension concentrating agents, aerosol and aerosol.Wetting powder contains 25 usually, 50 or 75% (weight) active component, and except that solid inert carrier, also contain the dispersant of 3-10% (weight) usually, and can add 0-10% (weight) stabilizing agent and/or other additive such as bleeding agent or sticker if need.Pulvis may be molded to the pulvis concentrating agents that has the composition similar to wetting powder but do not have dispersant usually, further with the solid carrier dilution, is contained 0.5-10% (weight) composition of active components usually in the ground.Granula is prepared into usually has 10 and 100 order (1.676-0.152mm) sizes, and available agglomerating or injection technique preparation.Usually, granula contains the active component of 0.5-75% (weight) and 0-10% (weight) additive such as stabilizing agent, surfactant, slowly-releasing modifying agent.So-called " dry powder can flow " is made up of the relatively little particle with relative high concentration active component.Outside but emulsion concentrate desolventizes, when needs, contain cosolvent usually, the 1-50%W/V active component, other additive of 2-20%W/V emulsifier and 0-20%W/V such as stabilizing agent, bleeding agent and corrosion inhibitor, suspension concentrating agents contain the active component of 10-75% (weight), the dispersant of 0.5-15% (weight), other additive such as defoamer, corrosion inhibitor, stabilizing agent, bleeding agent and the sticker of 0.1-10% (weight) usually.
Water dispersant and emulsion, for example by dilute with water according to the composition that wetting powder of the present invention or concentrate 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 bactericide, make it have the more activity of wide spectrum than independent general formula (I) compound.In addition, but the bactericidal activity of other bactericide mutual-through type (I) compound has synergistic effect.The example that can be included in the fungicide compound in the present composition has: nitrile bacterium azoles, triadimefon, benomyl, carbendazim, tpn, Cupravit, bordeaux mixture, furidazol, the hot salt of biguanides, hydroxyisoxazole, Fujione, kasugarnycin, mancozeb, maneb, zineb, Polyoxin, propineb, thiophanate methyl, tmtd, tridemorph, dimethomorph etc.
Can comprise Rogor, flolimat, chlopyrifos, chlorpyrifos-methyl, acephatemet, nuvacron, fenthion, phoxim, triaguron, Imidacloprid and pyrethroid such as sumicidin, fenpropathrin, taufluvalinate, cyhalothrin etc. with the suitable insecticide of compound formation composition of the present invention.
Compound of the present invention is compared with disclosed unsaturated oximino ether bactericide in the prior art has better bactericidal activity.Compound among the open CN1191670A of Chinese patent is effective to its testing compound concentration of efficiency test of various fungal diseases during for 100mg/L; And compound provided by the present invention when its concentration reduce to control compound 1/4 even 1/16 the time, its bactericidal activity still is better than control compound greatly.The bactericidal effect of this excellence has reached inventor of the present invention and invents a kind of purpose that just can control the active compound of various fungal diseases under littler dosage, has finished another important invention in the unsaturated oximino ether bactericide field.
With specific embodiment the present invention is described below, but does not limit the present invention.
Synthetic embodiment
Synthesizing of example 1 compound 1
17.5 gram (0.1 mole) 2, the 6-dichlorobenzaldehyde is dissolved in 100 milliliters of acetone, to the sodium hydrate aqueous solution of the gram of Dropwise 5 wherein 10%, keeps temperature to be no more than 40 ℃ in the dropping process.Drip and continue to stir one hour.Mixture is poured in the water, uses ethyl acetate extraction, washes extract again with water three times, and is dry concentrated that light yellow oil is 2,6-dichlorostyrene ylmethyl ketone 20.4 grams, yield 94.9%.
With 10 gram (0.0465 moles) 2,6-dichlorostyrene ylmethyl ketone, 7.77 gram hydroxylamine hydrochlorides (0.093 mole) and 12.9 gram (0.093 mole) potash refluxed 3 hours in 150 milliliters of ethanol.Reactant mixture is concentrated, and dilute with water is also used ethyl acetate extraction.The extract that merges is dry to be concentrated, and gets 2, and 6-dichlorostyrene ylmethyl ketoxime 9.3 grams are light yellow solid.Yield 86.93%.
At room temperature with 2.3 gram (0.01 moles) 2, the N of 6-dichlorostyrene ylmethyl ketoxime, dinethylformamide solution (10 milliliters) are added drop-wise to the N that contains 0.4 gram (0.01 mole) sodium hydroxide, in the dinethylformamide suspension (10 milliliters).After half an hour, with 2.86 grams (0.01 mole) (E)-N of 2-(bromomethyl) benzoyl group methyl formate-O-methyloxime, dinethylformamide solution (10 milliliters) is added in the reactant mixture, at room temperature continues to stir 2 hours.Mixture is poured in the water, used ethyl acetate extraction 2 times.The extract that merges washes with water 3 times, and is dry then, concentrated, gets thick product.Mixed liquor (1: 5) with ethyl acetate and benzinum obtains light yellow oil 1.28 grams, yield 29.43% for eluent carries out column chromatography.
0.75 methylamine 40% aqueous solution that restrains (0.00172 mole) above-claimed cpd and 3 times of mol ratios is added hot reflux in 50 ml methanol spend the night, concentrate back ethyl acetate extraction 2 times, the extract that merges washes with water 3 times, dry then, concentrate, obtain title compound 0.55 gram, be white solid, yield 73.3%.Fusing point 131-133 ℃
Nuclear magnetic resonance data: 2.03 (3H is unimodal) 2.82-2.87 (3H is bimodal) 3.87 (3H is unimodal) 4.97 (2H is unimodal) 6.5-6.6 (1H multimodal) 6.71 (2H is unimodal) 6.80-7.50 (7H multimodal)
Synthesizing of example 2 compounds 2
17.5 gram (0.1 mole) 2,3 dichloro benzaldehyde is dissolved in 100 milliliters of acetone, inwardly the sodium hydrate aqueous solution of Dropwise 5 gram 10% keeps temperature to be no more than 40 ℃ in the dropping process, continues afterwards to stir one hour.Mixture is poured in the water, adds ethyl acetate extraction, washes with water three times, dry concentrate light yellow oil 2,3-dichlorostyrene ylmethyl ketone 20.2 grams, yield 93.9%.
With 10 gram (0.0465 moles) 2,3-dichlorostyrene ylmethyl ketone, 7.77 gram hydroxylamine hydrochlorides (0.093 mole) and 12.9 gram (0.093 mole) potash refluxed 3 hours in 150 milliliters of ethanol.Reactant mixture is concentrated, and dilute with water is also used ethyl acetate extraction.The extract that merges is dry to be concentrated, and gets 2, and 3-dichlorostyrene ylmethyl ketoxime 9.5 grams are light yellow solid, yield 88.8%.
At room temperature with 2.3 gram (0.01 moles) 2, the N of 3-dichlorostyrene ylmethyl ketoxime, dinethylformamide solution (10 milliliters) are added drop-wise to the N that contains 0.4 gram (0.01 mole) sodium hydroxide, in the dinethylformamide suspension (10 milliliters).After half an hour, with 2.86 grams (0.01 mole) (E)-N of 2-(bromomethyl) benzoyl group methyl formate-O-methyloxime, dinethylformamide solution (10 milliliters) is added in the reactant mixture, at room temperature continues to stir 2 hours.Mixture is poured in the water, used ethyl acetate extraction 2 times.The extract that merges washes with water 3 times, and is dry then, concentrated, gets thick product.Mixed liquor (1: 5) with ethyl acetate and benzinum obtains light yellow oil 1.38 grams, yield 31.73% for eluent carries out column chromatography.
0.75 methylamine 40% aqueous solution that restrains (0.00172 mole) above-claimed cpd and 3 times of mol ratios is added hot reflux in 50 ml methanol spend the night, concentrate back ethyl acetate extraction 2 times, the extract that merges washes with water 3 times, dry then, concentrated, obtain title compound 0.65 gram, be thickness grease, yield 86.63%.
Nuclear magnetic resonance data: 2.04 (3H is unimodal) 2.82-2.87 (3H is bimodal) 3.89 (3H is unimodal) 5.01 (2H is unimodal) 6.5-6.6 (1H multimodal) 6.70 (2H is unimodal) 6.80-7.50 (7H multimodal)
Synthesizing of example 3 compounds 3
17.5 gram (0.1 mole) 2,4 dichloro benzene formaldehyde is dissolved in 100 milliliters of acetone, to the sodium hydrate aqueous solution of the gram of Dropwise 5 wherein 10%, keeps temperature to be no more than 40 ℃ in the dropping process, continues afterwards to stir one hour.Mixture is poured in the water, adds ethyl acetate extraction, washes with water three times again, and is dry concentrated that light yellow oil 2,4 dichloro benzene ethenyl methyl ketone 20.6 restrains yield 95.8%.
10 gram (0.0465 mole) 2,4 dichloro benzene ethenyl methyl ketones, 7.77 gram hydroxylamine hydrochlorides (0.093 mole) and 12.9 gram (0.093 mole) potash were refluxed 3 hours in 150 milliliters of ethanol.Reactant mixture is concentrated, and dilute with water is also used ethyl acetate extraction.The extract that merges is dry to be concentrated, and gets 2,4 dichloro benzene ethenyl methyl ketone oxime 9.1 grams, is light yellow solid, yield 85.06%.
At room temperature with the N of 2.3 gram (0.01 mole) 2,4 dichloro benzene ethenyl methyl ketone oximes, dinethylformamide solution (10 milliliters) is added drop-wise to the N that contains 0.4 gram (0.01 mole) sodium hydroxide, in the dinethylformamide suspension (10 milliliters).After half an hour, with 2.86 grams (0.01 mole) (E)-N of 2-(bromomethyl) benzoyl group methyl formate-O-methyloxime, dinethylformamide solution (10 milliliters) is added in the reactant mixture, at room temperature continues to stir 2 hours.Mixture is poured in the water, used ethyl acetate extraction 2 times.The extract that merges washes with water 3 times, and is dry then, concentrated, gets thick product.Mixed liquor (1: 5) with ethyl acetate and benzinum obtains light yellow oil 1.35 grams, yield 31.04% for eluent carries out column chromatography.
0.75 methylamine 40% aqueous solution that restrains (0.00172 mole) above-claimed cpd and 3 times of mol ratios is added hot reflux in 50 ml methanol spend the night, concentrate back ethyl acetate extraction 2 times, the extract that merges washes with water 3 times, dry then, concentrated, obtain title compound 0.63 gram, be thickness grease, yield 83.96%.
Nuclear magnetic resonance data: 2.03 (3H is unimodal) 2.82-2.87 (3H is bimodal) 3.88 (3H is unimodal) 5.01 (2H is unimodal) 6.4-6.6 (1H multimodal) 6.68 (2H is unimodal) 6.75-7.50 (7H multimodal)
Synthesizing of example 4 compounds 17
14.2 gram (0.1 mole) 2, the 6-difluorobenzaldehyde is dissolved in 100 milliliters of acetone, and inwardly the sodium hydrate aqueous solution of Dropwise 5 gram 10% will keep temperature to be no more than 40 ℃ in the dropping process, continues to stir one hour.Mixture is poured in the water, adds ethyl acetate extraction, washes with water three times, dry concentrate light yellow oil 2,6-difluoro styryl methyl ketone 15.7 grams, yield 86.26%.
With 8.46 gram (0.0465 moles) 2,6-difluoro styryl methyl ketone, 7.77 gram hydroxylamine hydrochlorides (0.093 mole) and 12.9 gram (0.093 mole) potash refluxed 3 hours in 150 milliliters of ethanol.Reactant mixture is concentrated, and dilute with water is also used ethyl acetate extraction.The extract that merges is dry to be concentrated, and gets 2, and 6-difluoro styryl methyl ketone oxime 7.91 grams are light yellow solid.Yield 86.37%.
At room temperature with 1.97 gram (0.01 moles) 2, the N of 6-difluoro styryl methyl ketone oxime, dinethylformamide solution (10 milliliters) are added drop-wise to the N that contains 0.4 gram (0.01 mole) sodium hydroxide, in the dinethylformamide suspension (10 milliliters).After half an hour, with 2.86 grams (0.01 mole) (E)-N of 2-(bromomethyl) benzoyl group methyl formate-O-methyloxime, dinethylformamide solution (10 milliliters) is added in the reactant mixture, at room temperature continues to stir 2 hours.Mixture is poured in the water, used ethyl acetate extraction 2 times.The extract that merges washes with water 3 times, and is dry then, concentrates, and gets thick product.Mixed liquor (1: 5) with ethyl acetate and benzinum obtains light yellow oil 1.18 grams, yield 29.35% for eluent carries out column chromatography.
0.75 methylamine 40% aqueous solution that restrains (0.00186 mole) above-claimed cpd and 3 times of mol ratios is added hot reflux in 50 ml methanol spend the night, concentrate back ethyl acetate extraction 2 times, the extract that merges washes with water 3 times, dry then, concentrated, obtain title compound 0.51 gram, be thickness grease, yield 68.17%.
Nuclear magnetic resonance data: 2.01 (3H is unimodal) 2.82-2.88 (3H is bimodal) 3.87 (3H is unimodal) 4.97 (2H is unimodal) 6.6-7.40 (10H multimodal)
Synthesizing of example 5 compounds 39
15.8 gram (0.1 mole) 2-chloro-6-fluorobenzaldehyde is dissolved in 100 milliliters of acetone, to the sodium hydrate aqueous solution of Dropwise 5 gram 10% wherein, keeps temperature to be no more than 40 ℃ in the dropping process, continues afterwards to stir one hour.Mixture is poured in the water, adds ethyl acetate extraction, washes with water three times, and is dry, concentrated that light yellow oil 2-chloro-6-fluorobenzene ethenyl methyl ketone 15.7 restrains yield 79.34%.
9.23 gram (0.0465 mole) 2-chloro-6-fluorobenzene ethenyl methyl ketones, 7.77 gram hydroxylamine hydrochlorides (0.093 mole) and 12.9 gram (0.093 mole) potash were refluxed 3 hours in 150 milliliters of ethanol.Reactant mixture is concentrated, and dilute with water is also used ethyl acetate extraction.The extract that merges is dry to be concentrated, and gets 2-chloro-6-fluorobenzene ethenyl methyl ketone oxime 8.38 grams, is light yellow solid.Yield 84.41%.
At room temperature with the N of 2.14 gram (0.01 mole) 2-chloro-6-fluorobenzene ethenyl methyl ketone oximes, dinethylformamide solution (10 milliliters) is added drop-wise to the N that contains 0.4 gram (0.01 mole) sodium hydroxide, in the dinethylformamide suspension (10 milliliters).After half an hour, with 2.86 grams (0.01 mole) (E)-N of 2-(bromomethyl) benzoyl group methyl formate-O-methyloxime, dinethylformamide solution (10 milliliters) is added in the reactant mixture, continues under the room temperature to stir 2 hours.Mixture is poured in the water, used ethyl acetate extraction 2 times.The extract that merges washes with water 3 times, and is dry then, concentrated, gets thick product.Mixed liquor (1: 5) with ethyl acetate and benzinum obtains light yellow oil 1.24 grams, yield 29.63% for eluent carries out column chromatography.
0.75 methylamine 40% aqueous solution that restrains (0.00179 mole) above-claimed cpd and 3 times of mol ratios is added hot reflux in 50 ml methanol spend the night, concentrate back ethyl acetate extraction 2 times, the extract that merges washes with water 3 times, dry then, concentrated, obtain title compound 0.59 gram, be thickness grease, yield 78.85%.
Nuclear magnetic resonance data: 2.02 (3H is unimodal) 2.83-2.88 (3H is bimodal) 3.87 (3H is unimodal) 4.97 (2H is unimodal) 6.4-7.40 (10H multimodal)
Formulation Example
Example 6
The compound 1 of 10 parts (weight) is dissolved in the following mixture, and this mixture contains the calcium dodecyl benzene sulfonate of the polyoxyethylene nonylphenol ether of 90 parts of (weight) dimethylbenzene, 6 parts (weight), 2 parts (weight) and 40 moles of ethylene oxide of 2 parts (weight) and the addition compound product of 1 mole of castor oil and prepares missible oil (reactive compound content is 9%).
Give birth to and survey embodiment
Example 7
Part of compounds has been carried out the bactericidal activity test.Method is as follows: testing compound is dissolved in 1: 1 acetone and carbinol mixture, again with 2: 1: 1 water, acetone and carbinol mixture (volume ratio) be diluted to desired concn.This solution is sprayed onto to be treated to dry on the measuring plants 2 hours, carried out the germ inoculation after one day.Activity in percentage, is divided into A, B, C, D level Four with respect to blank, and control rate 90%-100% is the A level, and control rate 75%-90% is the B level, and control rate 50%-75% is the C level, and control rate 0%-50% is the D level
Powdery mildew of cucumber
Dispenser was inoculated after one day.Investigation in about 7 days is placed in the inoculation back in the greenhouse.Test result sees Table (2)
Table (2)
Compound Concentration (mg/l) Active Concentration (mg/l) Active
?????????1 ????25 ????A ????6 ????A
?????????17 ????25 ????A ????6 ????A
?????????39 ????25 ????A ????6 ????A
Control compound 1 (4) ????25 ????D ????6 ????D
Control compound 2 (5) ????25 ????D ????6 ????D
Control compound 3 (6) ????25 ????D ????6 ????D
Control compound 4 (10) ????25 ????D ????6 ????D
Control compound 5 (2) ????25 ????C ????6 ????D
Control compound 6 (7) ????25 ????D ????6 ????D
Control compound 7 (9) ????25 ????D ????6 ????D
Control compound 8 (11) ????25 ????D ????6 ????D
Control compound 9 (12) ????25 ????D ????6 ????D
Control compound 10 (13) ????25 ????D ????6 ????D
Control compound 11 (19) ????25 ????D ????6 ????D
Control compound 12 (23) ????25 ????D ????6 ????D
Control compound 13 (40) ????25 ????D ????6 ????D
Control compound 14 (42) ????25 ????D ????6 ????D
Control compound 15 (45) ????25 ????D ????6 ????D
????????CK ????- ????O ????- ?????-
* control compound is the compound among the CN1191670A, is the numbering in this patent compound table in the bracket.
Under 25mg/l concentration, compound control rate of the present invention is the A level, is the C level and have only the control rate of compound 5 in the control compound, and all the other all are the D level; Under 6mg/l concentration, compound control rate of the present invention is the A level, and all control compounds are invalid substantially.From test result as can be seen, compound of the present invention has good preventive effect to powdery mildew of cucumber, obviously is better than control compound.
Rice blast
Dispenser was inoculated after one day.Preserving moisture in humidistat and be beneficial to infect in 36 hours in the inoculation back, moves into the greenhouse, 7 days left and right sides " Invest, Then Investigate "s.Test result sees Table (3)
Table (3)
Compound Concentration (mg/l) Active Concentration (mg/l) Active
????????1 ????25 ????A ????6 ????A
????????17 ????25 ????A ????6 ????A
????????39 ????25 ????A ????6 ????A
Control compound 1 (4) ????25 ????B ????6 ????D
Control compound 2 (5) ????25 ????C ????6 ????D
Control compound 3 (6) ????25 ????D ????6 ????D
Control compound 4 (10) ????25 ????D ????6 ????D
Control compound 5 (2) ????25 ????C ????6 ????D
Control compound 6 (7) ????25 ????D ????6 ????D
Control compound 7 (9) ????25 ????D ????6 ????D
Control compound 8 (11) ????25 ????D ????6 ????D
Control compound 9 (12) ????25 ????B ????6 ????C
Control compound 10 (13) ????25 ????B ????6 ????D
Control compound 11 (19) ????25 ????D ????6 ????D
Control compound 12 (23) ????25 ????C ????6 ????C
Control compound 13 (40) ????25 ????B ????6 ????D
Control compound 14 (42) ????25 ????D ????6 ????D
Control compound 15 (45) ????25 ????D ????6 ????D
????????CK ????- ????O
* control compound is the compound among the CN1191670A, is the numbering in this patent compound table in the bracket.
Under 25mg/l concentration, compound control rate of the present invention is the A level, and all control compound control rates are all below the B level; Under 6mg/l concentration, compound control rate of the present invention is the A level, and all control compounds are invalid substantially.From test result as can be seen, compound of the present invention has good preventive effect to rice blast, obviously is better than control compound.
Gray mold of cucumber
Dispenser was inoculated after one day.5 days left and right sides " Invest, Then Investigate "s are placed in the inoculation back in climatic chamber.Test result sees Table (4)
Table (4)
Compound Concentration (mg/l) Active Concentration (mg/l) Active
????1 ????25 ????A ????6 ????A
????17 ????25 ????A ????6 ????A
????????39 ????25 ????A ????6 ????A
Control compound 1 (4) ????25 ????D ????6 ????D
Control compound 2 (5) ????25 ????B ????6 ????D
Control compound 3 (6) ????25 ????D ????6 ????D
Control compound 4 (10) ????25 ????D ????6 ????D
Control compound 5 (2) ????25 ????D ????6 ????D
Control compound 6 (7) ????25 ????C ????6 ????D
Control compound 7 (9) ????25 ????D ????6 ????D
Control compound 8 (11) ????25 ????D ????6 ????D
Control compound 9 (12) ????25 ????D ????6 ????D
Control compound 10 (13) ????25 ????B ????6 ????C
Control compound 11 (19) ????25 ????D ????6 ????D
Control compound 12 (23) ????25 ????D ????6 ????D
Control compound 13 (40) ????25 ????C ????6 ????C
Control compound 14 (42) ????25 ????B ????6 ????D
Control compound 15 (45) ????25 ????B ????6 ????C
????????CK ????25 ????D ????6 ????D
* control compound is the compound among the CN1191670A, is the numbering in this patent compound table in the bracket.
Under 25mg/l concentration, compound control rate of the present invention is the A level, and all control compound control rates are all below the B level; Under 6mg/l concentration, compound control rate of the present invention is the A level, and all control compounds are all below the C level.From test result as can be seen, compound of the present invention obviously is better than control compound to the preventive effect of gray mold of cucumber.Wheat leaf rust
Dispenser was inoculated after one day.10 days left and right sides " Invest, Then Investigate "s are placed in the inoculation back in the greenhouse.Test result sees Table (5)
Table (5)
Compound Concentration (mg/l) Active Concentration (mg/l) Active
?????????1 ????25 ????A ????6 ????A
????????17 ????25 ????A ????6 ????A
????????39 ????25 ????A ????6 ????A
Control compound 1 (4) ????25 ????B ????6 ????C
Control compound 2 (5) ????25 ????C ????6 ????D
Control compound 3 (6) ????25 ????D ????6 ????D
Control compound 4 (10) ????25 ????D ????6 ????D
Control compound 5 (2) ????25 ????C ????6 ????D
Control compound 6 (7) ????25 ????D ????6 ????D
Control compound 7 (9) ????25 ????D ????6 ????D
Control compound 8 (11) ????25 ????D ????6 ????D
Control compound 9 (12) ????25 ????B ????6 ????D
Control compound 10 (13) ????25 ????B ????6 ????D
Control compound 11 (19) ????25 ????D ????6 ????D
Control compound 12 (23) ????25 ????B ????6 ????D
Control compound 13 (40) ????25 ????B ????6 ????D
Control compound 14 (42) ????25 ????B ????6 ????D
Control compound 15 (45) ????25 ????D ????6 ????D
????CK ????- ????O
* control compound is the compound among the CN1191670A, is the numbering in this patent compound table in the bracket.
Under 25mg/l concentration, compound control rate of the present invention is the A level, and all control compound control rates are all below the B level; Under 6mg/l concentration, compound control rate of the present invention is the A level, and all control compounds are invalid substantially.From test result as can be seen, compound of the present invention obviously is better than control compound to the preventive effect of wheat leaf rust.Wheat powdery mildew
Dispenser was inoculated after one day.7 days left and right sides " Invest, Then Investigate "s are placed in the inoculation back in the greenhouse.Test result sees Table (6)
Table (6)
Compound Concentration (mg/l) Active Concentration (mg/l) Active
??????????1 ????25 ????A ????6 ????A
??????????17 ????25 ????A ????6 ????A
??????????39 ????25 ????A ????6 ????A
Control compound 1 (4) ????25 ????C ????6 ????D
Control compound 2 (5) ????25 ????C ????6 ????D
Control compound 3 (6) ????25 ????D ????6 ????D
Control compound 4 (10) ????25 ????D ????6 ????D
Control compound 5 (2) ????25 ????B ????6 ????D
Control compound 6 (7) ????25 ????D ????6 ????D
Control compound 7 (9) ????25 ????D ????6 ????D
Control compound 8 (11) ????25 ????D ????6 ????D
Control compound 9 (12) ????25 ????B ????6 ????C
Control compound 10 (13) ????25 ????B ????6 ????D
Control compound 11 (19) ????25 ????D ????6 ????D
Control compound 12 (23) ????25 ????C ????6 ????D
Control compound 13 (40) ????25 ????B ????6 ????D
Control compound 14 (42) ????25 ????D ????6 ????D
Control compound 15 (45) ????25 ????D ????6 ????D
????CK ????- ????O
* control compound is the compound among the CN1191670A, is the numbering in this patent compound table in the bracket.
Under 25mg/l concentration, compound control rate of the present invention is the A level, and all control compound control rates are all below the B level; Under 6mg/l concentration, compound control rate of the present invention is the A level, and all control compounds are invalid substantially.From test result as can be seen, compound of the present invention has good preventive effect to wheat powdery mildew, obviously is better than control compound.Cucumber anthracnose
Dispenser was inoculated after one day.7 days left and right sides " Invest, Then Investigate "s are placed in the inoculation back in the greenhouse.Test result sees Table (7)
Table (7)
Compound Concentration (mg/l) Active Concentration (mg/l) Active
?????????1 ????25 ????A ????6 ????A
?????????17 ????25 ????A ????6 ????A
?????????39 ????25 ????A ????6 ????A
Control compound 1 (4) ????25 ????B ????6 ????C
Control compound 2 (5) ????25 ????C ????6 ????D
Control compound 3 (6) ????25 ????D ????6 ????D
Control compound 4 (10) ????25 ????D ????6 ????D
Control compound 5 (2) ????25 ????C ????6 ????C
Control compound 6 (7) ????25 ????D ????6 ????D
Control compound 7 (9) ????25 ????D ????6 ????D
Control compound 8 (11) ????25 ????D ????6 ????D
Control compound 9 (12) ????25 ????B ????6 ????D
Control compound 10 (13) ????25 ????B ????6 ????D
Control compound 11 (19) ????25 ????D ????6 ????D
Control compound 12 (23) ????25 ????B ????6 ????D
Control compound 13 (40) ????25 ????B ????6 ????D
Control compound 14 (42) ????25 ????B ????6 ????B
Control compound 15 (45) ????25 ????D ????6 ????D
?????????CK ????- ????O
* control compound is the compound among the CN1191670A, is the numbering in this patent compound table in the bracket.
Under 25mg/l concentration, compound control rate of the present invention is the A level, and all control compound control rates are all below the B level; Under 6mg/l concentration, compound control rate of the present invention is the A level, and the control rate of having only control compound 14 is the B level, and other all control compound is invalid substantially.From test result as can be seen, compound of the present invention has good preventive effect to cucumber anthracnose, obviously is better than control compound.

Claims (9)

1, unsaturated oximino ether bactericide is characterized in that the present invention has the unsaturated oxime ether structure and the stereoisomer thereof of general formula (I):
Figure A0011014300021
X in the formula 1-X 5Be selected from hydrogen, halogen, alkyl, alkoxyl, nitro, alkylhalide group.
Halogen comprises fluorine, chlorine, bromine and iodine.
2, compound according to claim 1 is characterized in that: X in the formula (I) 1-X 5Have at least two to be selected from halogen, alkyl, alkoxyl, nitro, alkylhalide group.
3, compound according to claim 1 and 2 is characterized in that: X in the formula (I) 1, X 5Be selected from halogen, X 2-X 4Be selected from hydrogen, halogen, alkyl, alkoxyl, nitro, alkylhalide group.
4, compound according to claim 1 and 2 is characterized in that: X in the formula (I) 1, X 5Be selected from halogen, X 2-X 4Be hydrogen.
5, compound according to claim 4 is characterized in that: X in formula (I) 1, X 5Be chlorine, X 2-X 4During for hydrogen, described compound is N-methyl 2-[2-((((1-methyl-3-(2 ', 6 '-dichlorophenyl)-2-acrylic) amino) oxygen base) methyl) phenyl]-2-methoxyl group imido grpup acetamide, structural formula is:
6, compound according to claim 4 is characterized in that: X in formula (I) 1Be chlorine, X 2-X 4Be hydrogen, X 5During for fluorine, described compound is N-methyl 2-[2-((((1-methyl-3-(2 '-chloro-6 '-fluorophenyl)-2-acrylic) amino) oxygen base) methyl) phenyl]-2-methoxyl group imido grpup acetamide, structural formula is:
Figure A0011014300031
7, compound according to claim 4 is characterized in that: X in formula (I) 1, X 5Be fluorine, X 2-X 4During for hydrogen, described compound is N-methyl 2-[2-((((1-methyl-3-(2 ', 6 '-difluorophenyl)-2-acrylic) amino) oxygen base) methyl) phenyl]-2-methoxyl group imido grpup acetamide, structural formula is:
8, a kind of microbicide compositions is characterized in that: it is that active component and other agricultural go up acceptable carrier or thinner that said composition contains the compound described in the claim 1.
9, the compound of general formula of the present invention (I) or its preparation can be used for preventing and treating on various crops by multiple fungus-caused diseases such as Phycomycetes, Oomycete, Ascomycetes and deuteromycetes.
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