- Synthesis method of metconazole
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The invention discloses a synthesis method of metconazole, and relates to the technical field of pesticides. Comprising the following steps: carrying out condensation reaction on 2, 2-dimethyl cyclopentanone and benzaldehyde to obtain 5-benzal-2, 2-dimethyl cyclopentanone; then, carrying out epoxidation reaction to obtain 7-benzal-4, 4-dimethyl-1-oxaspiro [2, 4] heptane; the preparation method comprises the following steps: carrying out a ring-opening reaction to obtain 5-benzal-2, 2-dimethyl-1-(1H-1, 2, 4-triazole-1-yl methyl) cyclopentanol, and then carrying out a ring-opening reaction to obtain 5-benzal-2, 2-dimethyl-1-(1H- The preparation method comprises the following steps: carrying out a reduction reaction on 2, 2-dimethyl-1-(1H-1, 2, 4-triazole-1-yl methyl) cyclopentanol to obtain 5-benzyl-2, 2-dimethyl-1-(1H-1, 2, 4-triazole-1-yl methyl And then carrying out a chlorination reaction to obtain metconazole. The 2, 2-dimethylcyclopentanone and benzaldehyde are used as raw materials, condensation, reduction, epoxidation, ring opening and chlorination are sequentially performed, the raw materials are cheap, easy to obtain, light in environmental load, green, clean and environmentally friendly, the yield of the obtained metconazole product is high, and the metconazole product has potential industrial production value.
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- Synthesis method of triazole bactericide
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The invention relates to a triazole bactericide synthesis method, which comprises: (a) mixing a cyclopentanone compound, a solid alkali, 1,2,4-triazole sodium and an organic solvent, stirring, heating, introducing an inert gas, carrying out bubbling dehydration, and adding trimethyl sulfoxide halide to form a reaction system so as to carry out a reaction; and (b) stopping introduction of the inertgas when the content of the cyclopentanone compound in the reaction system is lower than 1%, and sequentially concentrating, recrystallizing and drying to obtain the triazole bactericide. Compared with the prior art, the method simplifies the reaction process, is safer and more environment-friendly, reduces the production cost, and is convenient for industrial production.
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Paragraph 0031-0034
(2020/10/14)
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- A NOVEL FORM OF METCONAZOLE, A PROCESS FOR ITS PREPARATION AND USE OF THE SAME
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A crystalline modification I of 5- (4-chlorobenzyl) -2, 2-dimethyl-1- (1H-1, 2, 4-triazol-1-ylmethyl) cyclopentanol (metconazole) is provided. The crystalline modification is characterized, for example by exhibiting at least 3 of the following reflexes, in any combination, as 2θ ± 0.2 degree in an X-ray powder diffractogram (X-RPD) recorded using Cu-Kα radiation at 25℃ : 2θ = 10.3 ± 0.2 (1) 2θ = 15.8 ± 0.2 (4) 2θ = 20.6 ± 0.2 (5) 2θ = 22.2 ± 0.2 (6) 2θ = 23.3 ± 0.2 (7). A method of preparing the crystalline modification, compositions comprising the crystalline modification and its use in controlling fungal infestations are also provided.
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Paragraph 0078-0082
(2020/08/28)
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- Preparation method of metconazole (by machine translation)
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The method comprises the following steps: 2 - (2 - chlorobenzylidene) 2 - 2 -methylcyclopentanone and p-chlorobenzaldehyde react to obtain an epoxide; the epoxide reacts with triazole to obtain an epoxide; and the epoxide is reacted with triazole to obtain an open-loop product; and the ring-opening product 4 - is subjected -2 to 2 - catalytic hydrogenation to obtain the 2 - myclobutanil . 4 - beta-(4 -chlorbenzydrospirone; 5 -2 -5 -chlorobenzyl) 5 - and methylcyclopentanone react. Corey-Chayyyysky is obtained. The preparation method is low in cost, easy to obtain in the market; the reaction steps are all conventional reactions, reaction steps are simple, implementation; process is simple, reaction conditions are mild, operation; conversion rate is high, reaction time is short, control, and industrialization production. (by machine translation)
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- Preparation method of metconazole
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The invention relates to a new method for preparing metconazole. The method comprises the following steps: performing reaction on 4,4-dimethyl-7-(4-chlorobenzyl)-1-oxo-spiro[2,4]heptane of a formula (1) and hydrazine hydrate of a formula (2) to produce a compound of formula (3) as shown in the specification, and reacting with N-dichloromethamidine of a formula (4) to prepare a metconazole compoundof a formula (5). According to the method, the process is simple, the raw materials are easy to obtain, the cost is relatively low and few three wastes are produced; furthermore, the defect of generation of 1,3,4-triazole isomer is overcome, the content and the yield of the target product metconazole are increased, the content can reach to 95 percent or more, and the method is suitable for industrialized production.
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Paragraph 0010; 0017; 0019-0020; 0022-0023; 0025
(2019/09/17)
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- [...] and its preparation method (by machine translation)
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The invention discloses a high-purity [...] and its preparation method; its preparation as follows: cyclopentanone and P-formaldehyde condensation reaction to obtain the exocyclic double bond of the α, β - unsaturated ketone (II); then and methylation reagent reaction to obtain the α ', α' - double-methyl substituted exocyclic double bond of the α, β - unsaturated ketone (III); then under the action of catalyst and hydrogen reduction of the double bond is obtained by reaction of 2, 2 - dimethyl - 5 - (4 - benzylic) cyclopentanone (IV); the reduction product (IV) generating Johnson - Corey - Chaykovsky reaction to obtain the epoxy propane compound (V); finally the epoxy propane compounds (V) and 1, 2, 4 - triazole reaction and after recrystallized to obtain high-purity [...] (I). Preparation method of this invention the raw material is cheap, short route, good selectivity, high total yield, good atom economy advantages, is extremely suitable for industrial production. (by machine translation)
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- New and convenient approach for synthesis of metconazole
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In terms of environmental and food supply protection, development of green, efficient, and less toxic pesticides is of great importance and in continuous demand. Metconazole, a triazole antiseptic, possesses such advantages, being environmentally friendly and high efficiency with broad-spectrum activity against bacteria and fungi. However, previously reported synthetic routes for metconazole have many disadvantages, for example, requiring multiple steps, being complicated, and suffering from high cost. We report herein a new, convenient, and high-yield four-step (aldol condensation, dimethylation, hydrogenation, and one-pot triazolation) synthesis for metconazole with relatively low cost.
- Chen, Shusheng,Zhou, Muxing,Zhang, Zhenfeng,Zhang, Wanbin
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p. 6293 - 6298
(2017/10/03)
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- METHOD FOR PRODUCING TRIAZOLYL METHYL CYCLOALKANOL DERIVATIVE AND TRIAZOLYL METHYL CYCLOALKANOL DERIVATIVE-CONTAINING COMPOSITION
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Generation of by-product is reduced by producing a triazolylmethyl cycloalkanol derivative by reacting a cycloalkanone derivative and an alkali metal salt of 1,2,4-triazole in the presence of a sulfur ylide at a reaction temperature of higher than 110°C and 140°C or lower.
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Paragraph 0057; 0058
(2015/03/16)
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- FUNGICIDAL MIXTURES
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The present invention relates to fungicidal mixtures comprising, as active components, 1) azolylmethyloxiranes of the general formula I wherein the variables have the meanings described in the application, 2) a fungicidal compound II, and 3) optionally a further fungicidal compound II, where the compounds II of components 2 and 3 independently of one another are selected from the group consisting of the compounds described in the application, with the proviso that components 2 and 3 are not identical, and to the use of the fungicidal mixtures for controlling phytopathogenic fungi and to the compositions comprising them.
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- FUNGICIDAL MIXTURES
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The present invention relates to fungicidal mixtures comprising, as active components, 1) azolylmethyloxiranes of the general formula I in which the variables have the meanings described in the application, and 2) a fungicidal compound II, where the compounds II of component 2 are selected from among the compounds described in the application, and to the use of the fungicidal mixtures for controlling phytopathogenic fungi and to the compositions comprising them.
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- Synergistic Fungidical Active Substance Combinations
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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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- Arylphenyl-substituted cyclic keto enols
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The present invention relates to novel arylphenyl-substituted cyclic ketoenols, their preparation and the use of such ketoenols as pesticides and/or herbicides. The novel arylphenyl-substituted cyclic ketoenols are of the formula (I) in which CKE refers to the cyclic ketoenol and W, X, Y and Z are as defined in the specification.
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- Process for producing trimethylsulfoxonium bromide
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In a process for producing trimethylsulfoxonium bromide by reacting dimethyl sulfoxide and methyl bromide, methyl bromide is added to a mixture of dimethyl sulfoxide and a stabilizing agent under atmospheric pressure intermittently or continuously so that the final molar ratio of methyl bromide to dimethyl sulfoxide becomes 0.40:1 to 0.70:1, with the temperature of dimethyl sulfoxide being maintained at a temperature of 50° to 75° C. This process can realize a reduction of reaction time, an improvement of yield and establishment of safety of producing operations.
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- Process for preparation of azolylmethylcycloalkanol derivatives
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A process for preparing a derivative of azolylmethylcycloalkanol of the following formula (I) comprising, providing a solid-liquid two-phase mixture of a cycloalkanone derivative of formula (II), an azole compound of formula (III), a metal oxide of formula (IV), and an organic solvent, and adding a sulfonium compound of formula (V) to said solid-liquid two-phase mixture under heating while stirring, STR1 wherein R1 and R2 individually represent a hydrogen atom or an alkyl group; X is a halogen atom, an alkyl group, a haloalkyl group, a phenyl group, a cyano group, or a nitro group; m is an integer of 0 to 5 (when m is 2 or larger, Xs may be either the same or different); n is an integer of 0 to 2; A represents a nitrogen atom or a group CH; M1 represents an alkali metal atom or an alkaline earth metal atom; M2 represents an alkaline earth metal atom, a zinc atom, or two alkali metal atoms; Y represents a halogen atom or a C1 -C4 alkoxysulfonyloxy group; and p denotes an integer of 0 or 1.
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- Azolylmethyloxabicyclohexane derivatives and fungicidal compositions thereof
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Disclosed herein is a process for preparing a cis-azole derivative represented by the general formula (I) STR1 wherein R1 and R2 denote each a hydrogen atom or an alkyl group, R denotes a halogen atom, a nitro group, a cyano group, an alkyl group, a haloalkyl group or a phenyl group, A denotes a nitrogen atom or a methine group, and n stands for an integer of 1-5, which comprises reducing an azolylmethyloxabicyclohexane derivative represented by the general formula (VI) STR2 wherein R1, R2, R, A and n have the same meanings as defined above. A fungicidal composition comprising the azolylmethyloxabicyclohexane derivative represented by the above-mentioned general formula (VI) is also desclosed.
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- Process for the preparation of cyclopentane derivatives
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The present invention discloses a process to produce a compound of the formula (IA): STR1 or an acid addition salt or metal complex thereof, in which n represents an integer from 0 to 5; each R represents a halogen atom, or a nitro, cyano, alkyl, haloalkyl or phenyl group; R1 and R2 independently represent a hydrogen atom or an alkyl group; and A represents a nitrogen atom or a CH group; which comprises steps of: (1-a) reacting a compound of the formula (VI): STR2 in which n,R,R1 and R2 are as defined above, with a reducing agent to obtain a compound of the formula (IVA); or, as an alternative step, (1-b) reacting a compound of the formula (VII): STR3 in which n, R,R1 and R2 are as defined above and R5 represents a hydrogen atom or an alkyl group, with a reducing agent to obtain a compound of the formula (IVA); (2) reacting a compound of the formula (IVA): STR4 with a compound of the formula (V): in which n,R,R1 and R2 are as defined above and R3 represents a C1-4 alkyl group or a phenyl group each optionally substituted by one or more substituents selected from halogen atoms, nitro, cyano, hydroxyl, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkyl, amino, C1-4 alkylamino, di-C1-4 alkylamino, C1-4 alkoxycarbonyl, carboxyl, C1-4 alkanoyl, C1-4 alkylthio, C1-4 alkylsulphinyl, C1-4 alkylsulphonyl, carbamoyl, C1-4 alkylamido, C3 -8 cycloalkyl and phenyl groups and X represents a halogen atom, in the presence of a base to obtain a compound of the formula (IIA); (3) reacting a compound of the formula (IIA): STR5 with a compound of the formula (III): STR6 in which n,R,R1, R2, R3 and A are as defined above and Q represents a hydrogen or alkali metal atom, in the presence of a base to obtain a compound of the formula (IA), and optionally converting the resulting compound of the formula (IA) into an acid addition salt or metal complex thereof.
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- Process for producing azolylmethylcyclopentanol derivatives
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An azolylmethylcyclopentanol derivative which is useful as an agricultural and horticultural fungicide and which is represented by the formula (II) : wherein R1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R2 represents a hydrogen atom or an alkyl group having 1 or 2 carbon atoms, X represents a halogen atom, an alkyl group having 1 to 4 carbon atoms, a phenyl group, a cyano group, a trifluoromethyl group or a nitro group, A represents a nitrogen atom or a CH group and m is an integer of 1 to 5 is prepared by reacting a cyclopentanone derivative represented by the formula (I) : wherein R1, R2, X and m are as defined above, with an azole compound represented by the formula (III) : wherein A is as defined above and M represents an alkali metal atom or a hydrogen atom, and a sulfonium methylide or a sulfoxonium methylide in a polar solvent or a mixture of a polar solvent and an alcohol having 1 to 5 carbon atoms and, when M represents a hydrogen atom, in the presence of a base.
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