cas 94361-06-5, Cyproconazole | Articles data

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AN IMPROVED PROCESS FOR PREPARATION OF AN AZOLE FUNGICIDE
The present invention relates to improved process for the preparation of a fungicide of the class of azoles. The present invention specifically relates to an improved process for the preparation of (2RS,3RS;2SR,3SR)-2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol having the following Formula I.
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Page/Page column 7-12

(2021/06/26)

Method for preparing cyproconazole with 2,4'-dichloroacetophenone being raw material
The invention relates to the field of organic synthesis and especially relates to a method for preparing cyproconazole with 2,4'-dichloroacetophenone being a raw material. The method includes: a) performing a nucleophilic substitution reaction on the 2,4'-dichloroacetophenone and 1,2,4-triazole or 1,2,4-triazole salt to obtain 1-(4-chlorophenyl)-2-(1H-1,2,4-triazole-1-yl)ethyl ketone; b) performing a nucleophilic addition reaction on the 1-(4-chlorophenyl)-2-(1H-1,2,4-triazole-1-yl)ethyl ketone with one or more of a 3-halogenated-1-butylene Grignard reagent, a 3-halogenated-1-butylene organozinc reagent, a 1-halogenated-2-butylene Grignard reagent and a 1-halogenated-2-butylene organozinc reagent, thus generating 2-(4-chlorophenyl)-3-methyl-1-(1H-1,2,4-triazole-1-yl)-4-pentene-2-ol; c) performing a ring forming reaction on the 2-(4-chlorophenyl)-3-methyl-1-(1H-1,2,4-triazole-1-yl)-4-pentene-2-ol with one or more Simmons-Smith reagents prepared from dihalogenated methane, thus preparing the cyproconazole. The preparation method is short in route, gentle in reaction and high in yield. The reactions are free of dangerous reagents, so that the method is suitable for large scale industrial production.
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(2019/04/26)

Through 1 - chloro -2 - (4 - chlorophenyl) -3 - methyl -4 - pentene -2 - alcohol preparation triabimefron method
The invention relates to the field of organic synthesis, in particular to a through 1 - chloro - 2 - (4 - chlorophenyl) - 3 - methyl - 4 - pentene - 2 - ol preparation triabimefron method, comprises the following steps: (1) 2, 4' - dichloro ethanone deprotecting reagent or organic zinc reagent nucleophilic addition reaction, generating 1 - chloro - 2 - (4 - chlorophenyl) - 3 - methyl - 4 - pentene - 2 - ol, 2 - (4 - chlorophenyl) - 2 - (d - 3 - en - 2 - yl) - ethylene oxide or a mixture of both; (2) step (1) the product obtained with the halogeno methane ring 1 - chloro - 2 - (4 - chlorophenyl) - 3 - cyclopropyl-d - 2 - ol, 2 - (4 - chlorophenyl) - 2 - (1 - cyclopropyl-ethyl) - ethylene oxide or a mixture of both; (3) step (2) product with 1, 2, 4 - triazole or 1, 2, 4 - three nitrogen zuozuo salt undergo nucleophilic substitution reaction to obtain triabimefron. The invention provides a method for preparing triabimefron short route, high yield, the reaction process does not use a foul smell of sulfur reagent, not with the use of toxic reagent, also without the use of a noble metal catalyst, suitable for large-scale industrial production.
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(2019/03/24)

In order to 1 - (4 - chlorophenyl) -2 - (1 H - 1, 2, 4 - triazole -1 - yl) ethanone synthetic triabimefron method
The invention relates to the field of organic synthesis, in particular to a using the intermediate 1 - (4 - chlorophenyl) - 2 - (1 H - 1, 2, 4 - triazole - 1 - yl) ethanone synthetic triabimefron method, comprises the following steps: (1) 2, 4' - dichloro ethanone with 1, 2, 4 - triazole or 1, 2, 4 - three nitrogen zuozuo salt undergo nucleophilic substitution reaction to obtain 1 - (4 - chlorophenyl) - 2 - (1 H - 1, 2, 4 - triazole - 1 - yl) ethyl ketone; (2) 1 - (4 - chlorophenyl) - 2 - (1 H - 1, 2, 4 - triazole - 1 - yl) ethanone with 1 - cyclopropyl halogenated ethane Grignard reagent, 1 - cyclopropyl halogenated ethane organic zinc reagent or a mixture thereof a nucleophilic addition reaction triabimefron. The present invention provides a method of synthesis of triabimefron short route, mild reaction, high yield, the reaction process does not use a foul smell of sulfur ylide reagent, does not need to use dangerous [...], also will not produce a large amount of phosphorus-containing waste water, suitable for large-scale industrial production.
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Paragraph 0027; 0030; 0031

(2019/04/10)

Novel preparation method of cycloazole alcohol
The invention relates to the field of organic synthesis, in particular to a novel preparation method of cycloazole alcohol. The method includes following steps: (1), allowing 2, 4'-dichloroacetophenone to be in nucleophilic addition reaction with 1-cyclopropyl halogenated ethane Grignard reagent or 1-cyclopropyl halogenated ethane organic zinc reagent to generate 1-chloro-2-(4-chlorphenyl)-3-cyclopropyl butyl-2-alcohol or 2-(4-chlorphenyl)-2-(1-cyclopropy ethyl)-ethylene oxide or a mixture of the two; (2), enabling the product of the step (1) to be in nucleophilic substitution reaction with 1,2, 4-triazole or 1, 2, 4-triazole salt to obtain cycloazole alcohol; or enabling 1-chloro-2-(4-chlorphenyl)-3-cyclopropyl butyl-2-alcohol to react with alkali to generate 2-(4-chlorphenyl)-2-(1-cyclopropy ethyl)-ethylene oxide, then being in ring-opening reaction with 1, 2, 4-triazole or 1, 2, 4-triazole salt to obtain cycloazole alcohol. The preparation method is short in path, high in yield, needless of sulfur reagent with foul odor, highly toxic reagent and noble metal catalyst expensive in price in the process of reaction and suitable for large-scale industrial production.
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(2019/03/24)

Preparation method for cyproconazole
The invention discloses a preparation method for cyproconazole. The preparation method comprises the following steps: (1) dropwise adding dimethylsulfide to dimethyl sulfate and acetonitrile solution,to obtain solution A; (2) adding sodium methylate to the solution A, and dropwise adding acetonitrile solution of Alpha-methyl-4-chlorphenylcyclopropyl methyl ketone, after mixing, to obtain solutionB; (3) performing decompression treatment on the solution B, adding water and ethyl acetate for extracting, treating to obtain epoxide; (4) mixing triazole and the epoxide in N,N-dimethylformamide solution, adding sodium hydride, treating to obtain solution C; and (5) performing chloroform extraction on the solution C, after treatment, to obtain the cyproconazole. The preparation method is simplein process, and lower in production cost.
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Paragraph 0031-0048

(2019/03/08)

Preparation method of cyproconazole
The invention relates to a preparation method of cyproconazole as shown in the chemical structural formula I. According to the preparation method, 4-chlorobenzaldehyde is selected as a raw material to undergo a Grignard reaction to obtain a key intermediate 1-(4-chlorophenyl)-2-cyclopropyl-1-propanol; and 1-(4-chlorophenyl)-2-cyclopropyl-1-propanol undergoes an oxidation reaction, and then Sulfur ylide reaction and ring-opening reaction are successively carried out to prepare cyproconazole. Preparation reaction is as shown in the specification, wherein an oxidizing agent is selected from N-halosuccinimide, 1,3-dihalo-5,5-dimethyl hydantoin or ketone-alkoxy-aluminium; a sulfur ylide reagent is prepared by carrying out a reaction between (CH3)2S and (CH3)2SO4 under the action of KOH in isobutanol; DBU is 1,8-diazabicyalo[5.4.0]C11-7-en; and NMP is N-methylpyrrolidine.
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(2017/04/08)

Synergistic Active Compound Combinations Comprising Phenyltriazoles
The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and R2 have the meanings given in the description. and at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.
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(2011/07/29)

Synergistic Fungidical Active Substance Combinations
The present invention relates to novel active substance combinations which contain spiroxamine, which is known, a known azole and a known carboxamide and which are very suitable for controlling undesired phytopathogenic fungi.
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(2008/12/04)

Fungicide mixture
A composition comprising effective amounts ofa) a carbamate of the formula I where T is CH or N, n is 0, 1 or 2 and R is halogen, C1-C4-alkyl or C1-C4-haloalkyl, it being possible for the radicals R to be different if n is 2, andc) a compound III selected from the group consisting of the oxime ether carboxylate IIIa, the oxime ether carboxamide IIIb and the methoxyacrylate IIIc and optionally an oxime ether (II) and/or an azole (IV) as defined in the specification which exhibits a synergistically enhanced fungicidal effect is described.
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(2008/06/13)

Fungicide mixtures
A fungicidal mixture comprising a) an oxime ether of the formula I where the substituents have the following meanings: X is oxygen or amino (NH); Y is CH or N; Z is oxygen, sulfur, amino (NH) or C1-C4-alkylamino (N-alkyl); R′ is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkylmethyl, or, if desired, substituted benzyl; a) an oxime ether of the formula I where the substituents have the following meanings: X is oxygen or amino (NH); Y is CH or N; Z is oxygen, sulfur, amino (NH) or C1-C4-alkylamino (N—C1-C4-alkyl); R′ is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C2-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkylmethyl, or is benzyl which can be partially or fully halogenated and/or can have attached to it one to three of the following radicals: cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio; and at least one compound from groups b)-c): b.1) the oxime ether carboxylate of the formula IIa, b.2) the oxime ether carboxamide of the formula IIb, b.3) the methoxyacrylate of the formula IIc, c) one or more azole derivatives in a synergistically active amount.
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(2008/06/13)

Fungicidal mixtures
Fungicidal mixture, comprising a) an oxime ether carboxamide of the formula I STR1 where R is hydrogen or halogen and b) an azole derivative II selected from the group of the compounds II.1 to II.17 1-[(2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)-tetrahydrofuryl]-1H-1,2,4-triazole (II.1) 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (II.2) (±)-4-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-yl-methyl)-1,3-dioxolan-2-yl]phenyl 4-chlorophenyl ether (II.3) (E)-(R,S)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (II.4) (Z)-2-(1H-1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)oxirane (II.5) 4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazolylmethyl)butyronitrile (II.6) 3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl) quinazolin-4(3H)-one (II.7) bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-yl-methyl)silane (II.8) (R,S)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol (II.9) (1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimenthyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol [sic] (II.10) N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1-carboxamide (II.11) (±)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (II.12) (R,S)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (II.13) (±)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazolyl)-propyl 1,1,2,2-tetrafluoroethyl ether (II.14) and (E)-1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazole (II.15) (RS)-2,4'-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol (II.16) 2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)-hexanenitrile (II.17) in a synergistically active amount.
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(2008/06/13)

Fungicidal mixtures
A fungicidal mixture containing a) the oxime ether carboxamide of the formula I STR1 and b) an azole derivative II selected from the group of compounds II.1 to II.16 1-[(2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)tetra-hydrofuryl]-1H-1,2,4-triazole (II.1) 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (II.2) (±)-4-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-yl-methyl)-1,3-dioxolan-2-yl]phenyl 4-chlorophenyl ether (II.3) (E)-(R,S)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (II.4) (Z)-2-(1H-1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)oxirane (II.5) 4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazolyl methyl)butyronitrile (II.6) 3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one (II.7) bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-yl-methyl)silane (II.8) (R,S)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-l-yl)-hexan-2-ol (II.9) (1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (II.10) N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]-imidazole-1-carboxamide (II.11) (±)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (II.12) (R,S)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (II.13) (±)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl) propyl 1,1,2,2-tetrafluoroethyl ether (II.14) (E)-1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazole (II.15) and (RS)-2,4'-difluoro-α-(1H-1,2,4-triazol-1-yl-methyl)benzhydryl alcohol (II.16) in a synergistically active amount is described.
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(2008/06/13)