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CN1114590C - Unsaturated oximino ether bactericide - Google Patents

Unsaturated oximino ether bactericide Download PDF

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Publication number
CN1114590C
CN1114590C CN 00110143 CN00110143A CN1114590C CN 1114590 C CN1114590 C CN 1114590C CN 00110143 CN00110143 CN 00110143 CN 00110143 A CN00110143 A CN 00110143A CN 1114590 C CN1114590 C CN 1114590C
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compound
methyl
control compound
hydrogen
formula
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CN1309897A (en
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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 an unsaturated oxime ether structure in a general formula (I) and a stereomeric bactericidal compound of the structure. In the general formula, X1 to X5 are selected from hydrogen, halogen, alkyl groups, alkoxyl groups, nitro groups and alkyl halide groups. Compared with the existing unsaturated oxime ether bactericide, the components have better bactericidal activity.

Description

Unsaturated oximino ether bactericide
The invention belongs to disinfectant use in agriculture.
In the open CN1191670A of Chinese patent, reported sterilant with unsaturated oxime ether structure.The compound of these unsaturated oxime ether structures have 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 fungicidal activity of wide spectrum, compare with disclosed compound in the prior art, and they have higher fungicidal activity, have good preventive effect under lower dosage, thereby have finished the present invention.
The present invention relates to can be used as sterilant 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 steric isomer thereof of (I):
Figure C0011014300041
X in the formula 1-X 5Be selected from hydrogen, halogen, alkyl, alkoxyl group, nitro, alkylhalide group.
Halogen comprises fluorine, chlorine, bromine and iodine.
In general formula (I) compound, X 1-X 5The number that is selected from hydrogen must not be more than or equal to 4; Work as X 1, X 3, X 5When being selected from hydrogen, X 2, X 4Be not selected from chlorine.
Further, X in the general formula (I) 1, X 5Be selected from halogen, X 2-X 4Be selected from hydrogen, halogen, alkyl, alkoxyl group, nitro or alkylhalide group.
More preferably compound is X in the general formula (I) 1, X 5Be selected from halogen, X 2-X 4Be hydrogen.
More preferred three compounds are as follows:
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-propenyl) amino) oxygen base) methyl) phenyl]-2-methoxyl group imido grpup ethanamide, structural formula is:
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-propenyl) amino) oxygen base) methyl) phenyl]-2-methoxyl group imido grpup ethanamide, structural formula is:
Figure C0011014300052
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-propenyl) amino) oxygen base) methyl) phenyl]-2-methoxyl group imido grpup ethanamide, structural formula is:
Figure C0011014300053
In compound of the present invention, because carbon-to-carbon double bond is connected different substituting groups and can forms geometrical 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.
Figure C0011014300054
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 formula.Wherein the definition of X is the same, and Z is a leavings group, as halogen (chlorine, bromine or iodine).
Figure C0011014300081
The compound of general formula (IV) can prepare like this: in appropriate solvent as dimethyl formamide, tetrahydrofuran (THF), acetone or butanone, handle the oxime shown in the general formula (III) with suitable alkali as sodium hydroxide, sodium methylate 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 oxammonium hydrochloride in appropriate solvent (as methyl alcohol or ethanol), and reaction obtains to have suitable alkali (as sodium hydroxide or salt of wormwood) 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 aqueous methylamine solution reaction of general formula (IV).
Compound of the present invention is more effective sterilant.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 recondita) and other rust; Barley and wheat powdery mildew, powdery mildew of cucumber, apple mildew and uncinula necator.
Wheat hypochnus and glume blight ( Septoria nodorum).Length on the cereal wriggle spore, the mouth spore is mould, Septoria is sick, caryosphere shell Pseudomonas disease, Pseudocercosporella HerpotrichoidesWith Gaeumannomyces GraminisPeanut Cercospora arachidicolaWith Cercosporidium PersonataThe mould genus of other tail spore on beet, soybean and the paddy is sick.Tomato, cucumber, grape grey mould ( Botrytic cinerea).Hinge spore on the vegetables (as cucumber) belongs to sick.Anthrax on the cucumber, scab of apple, cucumber downy mildew, downy mildew of garpe, the epidemic disease on potato and the tomato is mould, on the paddy Thanatephorus CucumerisAnd other rhizoctonia on 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 simplification compound of the present invention or several compounds.
According to composition of the present invention, preferably contain from the activeconstituents 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 activeconstituents 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, fungicidal composition.
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 iso-butyl ketone (MIBK) and cyclohexyl ketone; Ether; Aromatic hydrocarbons such as benzene, toluene and dimethylbenzene; Petroleum fractions such as kerosene and mineral oil; Hydrochloric ether such as tetracol phenixin, tetrachloroethylene and trichloroethane.Usually, these mixtures of liquids also are suitable.
Desinsection, fungicidal 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 tensio-active agent.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.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; Glycol, sorbyl alcohol, the condenses of 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 or sulfonate; In molecule, contain the sulfuric acid of at least 10 carbon atoms or the basic metal or the alkaline earth salt of sulphonate, particular certain cancers; Sodium lauryl sulfate for example, the secondary alkyl ester 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 wettable powder, pulvis, granule and solution, emulsible enriching agent, emulsion, suspension enriching agent, aerosol and smoke substance.Wettable powder contains 25 usually, 50 or 75% (weight) activeconstituents, and except that solid inert carrier, also contain the dispersion agent of 3-10% (weight) usually, and can add 0-10% (weight) stablizer and/or other additive such as permeate agent or tackiness agent if need.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 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 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, the 1-50%W/V activeconstituents, other additive of 2-20%W/V emulsifying agent and 0-20%W/V such as stablizer, permeate agent and corrosion inhibitor, suspension enriching agent contain 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) compound.In addition, but the fungicidal activity of other sterilant mutual-through type (I) compound has synergism.The example that can be included in the fungicide compound in the present composition has: nitrile bacterium azoles, triadimefon, F-1991, derosal, m-tetrachlorophthalodinitrile, Cupravit, Bordeaux mixture, fuberidazole, the hot salt of biguanides, hymexazol, Fujione, kasugamycin, zinc manganese ethylenebisdithiocarbamate, maneb, zineb, Polyoxin, propineb, thiophanate methyl, thiram, tridemorph, dimethomorph 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.
Compound of the present invention is compared with disclosed unsaturated oximino ether bactericide in the prior art has better fungicidal 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 fungicidal activity still is better than control compound greatly.The sterilization 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 aqueous sodium hydroxide 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 oxammonium hydrochlorides (0.093 mole) and 12.9 gram (0.093 mole) salt of wormwood refluxed 3 hours in 150 milliliters of ethanol.Reaction mixture is concentrated, and dilute with water is also used ethyl acetate extraction.The extracting solution 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-(brooethyl) benzoyl group methyl-formiate-O-methyloxime, dinethylformamide solution (10 milliliters) is added in the reaction mixture, at room temperature continues to stir 2 hours.Mixture is poured in the water, used ethyl acetate extraction 2 times.The extracting solution that merges washes with water 3 times, and is dry then, concentrated, gets thick product.Mixed solution (1: 5) with ethyl acetate and sherwood oil obtains light yellow oil 1.28 grams, yield 29.43% for elutriant carries out column chromatography.
Methylamine 40% aqueous solution reflux in 50 ml methanol of 0.75 gram (0.00172 mole) above-claimed cpd and 3 times of mol ratios is spent 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 aqueous sodium hydroxide 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 oxammonium hydrochlorides (0.093 mole) and 12.9 gram (0.093 mole) salt of wormwood refluxed 3 hours in 150 milliliters of ethanol.Reaction mixture is concentrated, and dilute with water is also used ethyl acetate extraction.The extracting solution 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-(brooethyl) benzoyl group methyl-formiate-O-methyloxime, dinethylformamide solution (10 milliliters) is added in the reaction mixture, at room temperature continues to stir 2 hours.Mixture is poured in the water, used ethyl acetate extraction 2 times.The extracting solution that merges washes with water 3 times, and is dry then, concentrated, gets thick product.Mixed solution (1: 5) with ethyl acetate and sherwood oil obtains light yellow oil 1.38 grams, yield 31.73% for elutriant carries out column chromatography.
Methylamine 40% aqueous solution reflux in 50 ml methanol of 0.75 gram (0.00172 mole) above-claimed cpd and 3 times of mol ratios is spent 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 oily matter, 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 aqueous sodium hydroxide 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 oxammonium hydrochlorides (0.093 mole) and 12.9 gram (0.093 mole) salt of wormwood were refluxed 3 hours in 150 milliliters of ethanol.Reaction mixture is concentrated, and dilute with water is also used ethyl acetate extraction.The extracting solution 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-(brooethyl) benzoyl group methyl-formiate-O-methyloxime, dinethylformamide solution (10 milliliters) is added in the reaction mixture, at room temperature continues to stir 2 hours.Mixture is poured in the water, used ethyl acetate extraction 2 times.The extracting solution that merges washes with water 3 times, and is dry then, concentrated, gets thick product.Mixed solution (1: 5) with ethyl acetate and sherwood oil obtains light yellow oil 1.35 grams, yield 31.04% for elutriant carries out column chromatography.
Methylamine 40% aqueous solution reflux in 50 ml methanol of 0.75 gram (0.00172 mole) above-claimed cpd and 3 times of mol ratios is spent 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 oily matter, 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 aqueous sodium hydroxide 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 oxammonium hydrochlorides (0.093 mole) and 12.9 gram (0.093 mole) salt of wormwood refluxed 3 hours in 150 milliliters of ethanol.Reaction mixture is concentrated, and dilute with water is also used ethyl acetate extraction.The extracting solution 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-(brooethyl) benzoyl group methyl-formiate-O-methyloxime, dinethylformamide solution (10 milliliters) is added in the reaction mixture, at room temperature continues to stir 2 hours.Mixture is poured in the water, used ethyl acetate extraction 2 times.The extracting solution that merges washes with water 3 times, and is dry then, concentrates, and gets thick product.Mixed solution (1: 5) with ethyl acetate and sherwood oil obtains light yellow oil 1.18 grams, yield 29.35% for elutriant carries out column chromatography.
Methylamine 40% aqueous solution reflux in 50 ml methanol of 0.75 gram (0.00186 mole) above-claimed cpd and 3 times of mol ratios is spent 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 oily matter, 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 aqueous sodium hydroxide 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 oxammonium hydrochlorides (0.093 mole) and 12.9 gram (0.093 mole) salt of wormwood were refluxed 3 hours in 150 milliliters of ethanol.Reaction mixture is concentrated, and dilute with water is also used ethyl acetate extraction.The extracting solution 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-(brooethyl) benzoyl group methyl-formiate-O-methyloxime, dinethylformamide solution (10 milliliters) is added in the reaction mixture, continues under the room temperature to stir 2 hours.Mixture is poured in the water, used ethyl acetate extraction 2 times.The extracting solution that merges washes with water 3 times, and is dry then, concentrated, gets thick product.Mixed solution (1: 5) with ethyl acetate and sherwood oil obtains light yellow oil 1.24 grams, yield 29.63% for elutriant carries out column chromatography.
Methylamine 40% aqueous solution reflux in 50 ml methanol of 0.75 gram (0.00179 mole) above-claimed cpd and 3 times of mol ratios is spent 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 oily matter, 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 dodecylbenzene sulphonate 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 adduct of 1 mole of castor oil and prepares missible oil (active compound content is 9%).
Give birth to and survey embodiment
Example 7
Part of compounds has been carried out the fungicidal 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 per-cent, is divided into A, B, C, D level Four with respect to blank, and inverse amplification factor 90%-100% is the A level, and inverse amplification factor 75%-90% is the B level, and inverse amplification factor 50%-75% is the C level, and inverse amplification factor 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 - 0
*Control compound is the compound among the CN1191670A, is the numbering in this patent compound table in the bracket.
Under 25mg/l concentration, compound inverse amplification factor of the present invention is the A level, is the C level and have only the inverse amplification factor of compound 5 in the control compound, and all the other all are the D level; Under 6mg/l concentration, compound inverse amplification factor 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 - 0
*Control compound is the compound among the CN1191670A, is the numbering in this patent compound table in the bracket.
Under 25mg/l concentration, compound inverse amplification factor of the present invention is the A level, and all control compound inverse amplification factors are all below the B level; Under 6mg/l concentration, compound inverse amplification factor 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 inverse amplification factor of the present invention is the A level, and all control compound inverse amplification factors are all below the B level; Under 6mg/l concentration, compound inverse amplification factor 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 - 0
*Control compound is the compound among the CN1191670A, is the numbering in this patent compound table in the bracket.
Under 25mg/l concentration, compound inverse amplification factor of the present invention is the A level, and all control compound inverse amplification factors are all below the B level; Under 6mg/l concentration, compound inverse amplification factor 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 - 0
*Control compound is the compound among the CN1191670A, is the numbering in this patent compound table in the bracket.
Under 25mg/l concentration, compound inverse amplification factor of the present invention is the A level, and all control compound inverse amplification factors are all below the B level; Under 6mg/l concentration, compound inverse amplification factor 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 - 0
*Control compound is the compound among the CN1191670A, is the numbering in this patent compound table in the bracket.
Under 25mg/l concentration, compound inverse amplification factor of the present invention is the A level, and all control compound inverse amplification factors are all below the B level; Under 6mg/l concentration, compound inverse amplification factor of the present invention is the A level, and the inverse amplification factor 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 (8)

1, unsaturated oximino ether bactericide is characterized in that this sterilant has the unsaturated oxime ether structure and the steric isomer thereof of general formula (I):
In the formula: X 1-X 5Be selected from hydrogen, halogen, alkyl, alkoxyl group, nitro or alkylhalide group must not be more than or equal to 4 but be selected from the number of hydrogen; Halogen comprises fluorine, chlorine, bromine or iodine; Work as X 1, X 3, X 5When being selected from hydrogen, X 2, X 4Can not be selected from chlorine.
2, compound according to claim 1 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 group, nitro or alkylhalide group.
3, compound according to claim 2 is characterized in that: X in the formula (I) 1, X 5Be selected from halogen, X 2-X 4Be hydrogen.
4, compound according to claim 3 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-propenyl) amino) oxygen base) methyl) phenyl]-2-methoxyl group imido grpup ethanamide, structural formula is:
5, compound according to claim 3 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-propenyl) amino) oxygen base) methyl) phenyl]-2-methoxyl group imido grpup ethanamide, structural formula is:
Figure C0011014300031
6, compound according to claim 3 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-propenyl) amino) oxygen base) methyl) phenyl]-2-methoxyl group imido grpup ethanamide, structural formula is:
7, a kind of Bactericide composition is characterized in that: it is that activeconstituents and agricultural go up acceptable carrier or thinner that said composition contains the compound described in the claim 1.
8, the compound of general formula (I) or its composition on the control crop by the purposes of Phycomycetes, Oomycete, Ascomycetes and the fungus-caused disease of deuteromycetes.
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