- Preparation method of cyazofamid
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The invention discloses a preparation method of cyazofamid, comprising the following steps: carrying out a reaction on 5-(para-toluene)-1H-imidazole, anhydrous potassium carbonate, ethyl acetate and N,N-dimethylamino sulfonyl chloride at 50-77 DEG C for 6-12 h, cooling to room temperature, washing with water, extracting, drying, evaporating to remove ethyl acetate to obtain an intermediate A crudeproduct, and recrystallizing to obtain an intermediate A; (2) carrying out a reaction on the intermediate A, copper salt, a cyanation reagent, an oxidizing agent and N,N-dimethylformamide at 110-130DEG C for 6-12 h, cooling to room temperature, recovering N,N-dimethylformamide, washing with water, extracting, drying, evaporating to remove ethyl acetate to obtain an intermediate B crude product,and recrystallizing to obtain an intermediate B; and (3) stirring and carrying out a reaction on the intermediate B, N-chlorosuccinimide and acetonitrile at room temperature for 2-6 h, recovering thesolvent acetonitrile after the reaction, neutralizing to neutral level by adding a sodium bicarbonate solution, extracting, drying, evaporating to remove ethyl acetate to obtain a cyazofamid crude product, and recrystallizing to obtain cyazofamid. The preparation method of the invention has high reaction yield and good selectivity.
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Paragraph 0019; 0024; 0025; 0026-0032; 0033-0039
(2019/01/06)
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- PROCESS FOR THE PREPARATION OF 2-CYANOIMIDAZOLE COMPOUNDS
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It is an object of the present invention to provide a novel and advantageous process for commercially preparing of 2-cyanoimidazole compounds. More particularly, it relates to an efficient method of preparation of cyazofamid synthetic precursor by simultaneous conversion of aldoxime group to the corresponding cyano-derivative and reducing of N-oxygenated-imidazole ring to imidazole under mild conditions using reducing agent selected from the group consisting of metal salts of sulfur-containing derivatives in the presence of a polar organic solvent.
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- Synthesis method of cyazofamid
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The invention discloses a synthesis method of cyazofamid. The synthesis method of cyazofamid comprises the following steps: synthesizing 2,2-halogenated-4'-methyl acetophenone; synthesizing 1-hydroxy-4-(4-methyl phenyl)-2-oxime imidazole-3-oxide; synthesizing 2-cyan-4-chlorine-5-(4'-methyl phenyl)imidazole; adding methanol into 1-hydroxy-4-(4-methyl phenyl)-2-oxime imidazole-3-oxide, performing ice-water bath reaction, adding sulfoxide chloride, performing temperature-rising reaction, adding acetonitrile and N-chlorosuccinimide, and performing reaction; and synthesizing cyazofamid: adding 2-cyan-4-chlorine-5-(4'-methyl phenyl)imidazole, anhydrous potassium carbonate, ethyl acetate and N,N-dimethylsulfamoyl chloride into a reaction kettle, and performing refluxing reaction. The synthesis method of cyazofamid has the advantages of rich raw material source, easily available raw materials, low cost, mild reaction condition, no need of special equipment, high economic property, high total yield and good industrialized prospect.
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- Synthetic method of 4-chloride-2-cyano-1-dimethylaminosulfonyl-5-(4-methylphenyl) imidazole
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The invention discloses a synthetic method of 4-chloride-2-cyano-1-dimethylaminosulfonyl-5-(4-methylphenyl) imidazole and relates to the technical field of organic synthesis. The synthetic method comprises the following steps: taking 4(5)-chloride-2-cyano-5(4)-(4-methylphenyl) imidazole and dimethylaminosulfonyl chloride as reaction raw materials, ethyl acetate and cyclohexane as reaction solvents, and potassium carbonate as an acid binding agent, adding in two batches and preparing a product, namely the 4-chloride-2-cyano-1-dimethylaminosulfonyl-5-(4-methylphenyl) imidazole through substitution reaction. The synthetic method disclosed by the invention has the benefits that the low-purity and low-content raw material, namely the 4(5)-chloride-2-cyano-5(4)-(4-methylphenyl) imidazole, does not need to be highly purified and can be used for preparing a target product; through the synthetic method, the molar yield of the product reaches 80 percent or above, and the purity reaches 99 percent, so that the yield and the purity of the product are ensured.
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Paragraph 0016; 0017; 0019; 0021; 0023; 0025; 0027
(2017/08/31)
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- A 4-chloro-2-cyano-N, N-dimethyl-5 - (4 the [...] -methyl-phenyl) - 1H-imidazole-1-sulfonamide synthesis method
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The invention discloses a synthesis method of 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide (cyazofamid). According to the synthesis method, methylacetophenone is taken as a raw material, selenium dioxide is used for oxidation to prepare an intermediate, namely 2-carbonyl-2-p-benzyl aldehyde, then N,N-dimethylformamide and the like are taken as solvents, thionyl chloride is taken as a chlorinating agent and reducing agent for preparing the intermediate, and then intermediate further reacts with N,N-dimethyl sulfonamide chloride to synthesize the cyazofamid. Compared with the prior art, the synthesis method has the advantages that the reaction period is shortened, the post-treatment process is simplified and the synthesis method is suitable for mass industrial production.
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- 4-chloro-2-cyano-N, N-dimethyl-5-P-tolyl-imidazole-1-sulfonamide synthesis method
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The invention discloses a method for synthesizing 4-chloro-2-cyano-N,N-dimethyl-5-p-methylphenylimidazole-1-sulfamide. The method is characterized in that 2-carbonyl-2-P-benzyl acetaldehyde is used as a raw material and reacted with glyoxylic acid to synthesize an imidazole ring, and then ammoniation, dehydration, chlorination and sulfonylation are performed, so that 4-chloro-2-cyano-N,N-dimethyl-5-p-methylphenylimidazole-1-sulfamide is finally synthesized. The purity of 4-chloro-2-cyano-N,N-dimethyl-5-p-methylphenylimidazole-1-sulfamide prepared by adopting the synthesizing method reaches over 98.0%, and the total yield reaches over 44.5%. The method is cheap and readily available in raw materials, simple, mild in reaction conditions and low in environmental pollution, and produces little wastewater. The method is mainly applied to synthesis of 4-chloro-2-cyano-N,N-dimethyl-5-p-methylphenylimidazole-1-sulfamide serving as a pesticide bactericide.
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- Agent for controlling animal diseases caused by parasites
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The present invention provides an agent for controlling animal diseases caused by parasites, which contains, as an active ingredient, an imidazole compound represented by the formula (I): 1wherein R1 is a cyano group, R2 is an alkyl group which may be substituted, or a phenyl group which may be substituted, R3 is a chlorine atom, and R4 is a dimethylamino group.
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- PESTICIDAL COMPOSITION AND METHOD FOR CONTROLLING PESTS
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A pesticidal composition comprising at least one specific imidazole compound and at least one fungicide selected from the group consisting of 3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide and N-( alpha -cyano-2-thienyl)-4-ethyl-2-(ethylamino)-5-thiazole carboxyamide, as active ingredients.
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- Composition for controlling harmful bio-organisms and method for controlling harmful bio-organisms using the same
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A composition for controlling harmful bio-organisms comprising (a) at least one imidazole compound represented by formula (I): wherein R represents a lower alkyl group or a lower alkoxy group; and n represents an integer of 1 to 5, as an active ingredient, and (b) at least one inorganic phosphorus compound and/or at least one fungicide for Phycomycetes as an active ingredient or (c) a spreader as an activity-enhancing ingredient, and a method for controlling harmful bio-organisms comprising applying the composition for controlling harmful bio-organisms onto harmful bio-organisms.
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- Processes for producing 1-substituted-2-cyanoimidazole compounds
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A process for producing 1-substituted-2-cyanoimidazole compounds is described, which comprises (1) undergoing a reaction of a compound represented by formula (IV), hydroxylamine or a mineral acid salt thereof, and glyoxal or glyoxime to produce a compound represented by formula (III), (2) undergoing a reaction of the compound represented by formula (III) with thionyl chloride or thionyl bromide in the presence of N,N-dialkylamide to produce a reaction mixture, and then reacting the produced reaction mixture with sulfur chloride to produce a 2-cyanoimidazole compound represented by formula (II), and (3) undergoing a sulfamoylation reaction and an isomerization reaction of the 2-cyanoimidazole compound represented by formula (II) and a compound represented by formula (V) in the presence of at least one base selected from carbonates of alkali metals and bicarbonates of alkali metals and a polar solvent to produce a 1-substituted-2-cyanoimidazole compound represented by formula (I-b). The formulae and substituents formulae are specifically defined in the specification. STR1
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