- An Integrated Experimental and Computational Approach for Characterizing the Kinetics and Mechanism of Triadimefon?Racemization
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Enantiomers of chiral molecules commonly exhibit differing pharmacokinetics and toxicities, which can introduce significant uncertainty when evaluating biological and environmental fates and potential risks to humans and the environment. However, racemization (the irreversible transformation of one enantiomer into the racemic mixture) and enantiomerization (the reversible conversion of one enantiomer into the other) are poorly understood. To better understand these processes, we investigated the chiral fungicide, triadimefon, which undergoes racemization in soils, water, and organic solvents. Nuclear magnetic resonance (NMR) and gas chromatography / mass spectrometry (GC/MS) techniques were used to measure the rates of enantiomerization and racemization, deuterium isotope effects, and activation energies for triadimefon in H2O and D2O. From these results we were able to determine that: 1) the alpha-carbonyl carbon of triadimefon is the reaction site; 2) cleavage of the C-H (C-D) bond is the rate-determining step; 3) the reaction is base-catalyzed; and 4) the reaction likely involves a symmetrical intermediate. The B3LYP/6–311?+?G** level of theory was used to compute optimized geometries, harmonic vibrational frequencies, nature population analysis, and intrinsic reaction coordinates for triadimefon in water and three racemization pathways were hypothesized. This work provides an initial step in developing predictive, structure-based models that are needed to identify compounds of concern that may undergo racemization. Chirality 28:633–641, 2016.
- Cheng, Qianyi,Teng, Quincy,Marchitti, Satori A.,Dillingham, Caleb M.,Kenneke, John F.
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- Method for preparing trifloxystrobin by adopting microchannel reactor
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The invention belongs to the technical field of organic synthesis, and particularly relates to a method for preparing trifloxystrobin by adopting a microchannel reactor. The method comprises the following steps: dissolving a raw material methyl (E)-2-(2-chloromethylphenyl)-2-methoxyiminoacetate or methyl (E)-2-(2-bromomethylphenyl)-2-methoxyiminoacetate and m-trifluoromethyl acetophenone oxime into a solvent; dissolving sodium methoxide in a solvent; and finally, pumping the two solutions into a micro-channel reactor for complete reaction to obtain a trifloxystrobin feed liquid, and carrying out elutriation and recrystallization to obtain the trifloxystrobin product,wherein the content of trifloxystrobin is 99% or above, and the yield of the step can reach 94% or above. The preparation method provided by the invention has the advantages of simple process operation, high product quality, high yield, less three wastes, small environmental pollution, continuous production, safety and the like, and is suitable for industrial production.
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Paragraph 0044-0050; 0058-0064; 0072-0077
(2021/09/04)
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- Methods and Compositions for Use in Glued-Wood Products
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The present invention relates to biocide-composites providing high retention of biocides in glueline-treated glued-wood products that are hot-pressed or hot-pressed and block-stacked during manufacture.
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- Preparation method of trifloxystrobin
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The invention discloses a preparation method of trifloxystrobin. The method comprises the following steps: step 1, carrying out ultrasonic reaction on 3-trifluoromethylacetophenone oxime and (E)-2-(2'-bromomethyl phenyl)-2- carbonylacetic acid methyl ester -O-methylketone oxime in the presence of an acid-binding agent and an organic solvent; step 2, after finishing of the reaction, performing filtering to remove solids, performing washing with water, and carrying out reduced pressure distillation to remove a solvent to obtain a trifloxystrobin crude product; and step 3, recrystallizing a trifloxystrobin crude product with a low-polarity organic solvent, prforming filtering and drying to obtain a trifloxystrobin finished product. Compared with the traditional preparation method, the preparation method disclosed by the invention has the beneficial effects that firstly, an ultrasonic reaction instrument is adopted for reaction, and a low-boiling-point solvent is used for replacing a high-boiling-point reaction solvent, so that the production safety of the product is improved; secondly, the preparation method provided by the invention uses an ultrasonic reaction instrument for reaction, so that the reaction time is greatly shortened, the raw material conversion rate is high, the impurity content is obviously reduced; meanwhile, the production efficiency and the purity of the trifloxystrobin product are improved.
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Paragraph 0027-0037
(2020/07/12)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF TRIFLOXYSTROBIN
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The present invention relates to an improved process for the preparation of trifloxystrobin of formula (I), which is simple, economical, efficient, user and environment friendly, moreover commercially viable with higher yield and chemical purity.
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Page/Page column 17
(2019/04/10)
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- Trifloxystrobin and preparation method of intermittent thereof
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The invention relates to a preparation method of trifloxystrobin. Preparation reaction of the trifloxystrobin is as shown in the description, wherein R is selected from C2-C5 linear alkyl or C3-C5 branched alkyl; in bromination reaction, a brominating agent is selected from NBS or 1,3-dibromo-5,5-dimethylhydantoin.
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Paragraph 0098-0101
(2018/12/13)
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- A NOVEL PROCESS FOR THE PREPARATION OF TRIFLOXYSTROBIN
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The present invention relates to a novel process for preparation of methyl (αE)-(α- (methoxyimino)-2-[[[(E)-[1-[3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] benzeneaceate (Trifloxystrobin) compound of formula (I) in free form or in agro chemically acceptable salt form useful as a pest control agent.The present invention also relates to a novel process for preparation of methyl (2E)-[2-(bromomethyl) phenyl] (methoxyimino) ethanoate of formula (X) intermediate of Trifloxystrobin. [Formula should be inserted here].
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- The photocyclization-dependent ratiometric fluorescent switch: Synthesis, characterization and properties of some terpyridyl-based dithienylethenes
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Some terpyridyl-based dithienylethenes were synthesized and their structures were confirmed by NMR spectroscopy, mass spectroscopy and elemental analysis. The photochromic properties and fluorescence behaviors of these compounds have been measured upon ir
- Hu, Fang,Jiang, Chuanyin,Liu, Wenju,Wang, Jinjian,Yin, Jun,Liu, Sheng Hua
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p. 161 - 167
(2016/09/02)
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- Synthesis process of triazolone
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The invention discloses a synthesis process of triazolone, which includes the steps of: A) preparing triazole; B) dissolving parachlorophenol and potassium carbonate in an organic solvent to form a mixture system, heating the mixture system to 90-100 DEG C and dropwise adding chloropinacolone to the mixture system, and maintaining the temperature for 3-5 h to obtain a first intermediate; C) dropwise adding a chlorine source to an organic solution of the first intermediate, and maintaining the temperature for 3 h at 50-60 DEG C; D) adding the triazole to the mixture system in the step C), heating the mixture system to 100-120 DEG C and maintaining the temperature for 2-3 h to prepare the triazolone. The synthesis process is simple and is low in content of byproducts during synthesis. By adjusting the content of inorganic substances in reaction products, the reaction proceeds towards positive direction, thus increasing reaction yield. The synthesis process is suitable for industrial production.
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Paragraph 0019-0023
(2017/10/07)
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- Trifloxystrobin synthesizing method
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The invention discloses a trifloxystrobin synthesizing method, and relates to the preparation of trifloxystrobin in organic chemicals. The trifloxystrobin synthesizing method comprises the following steps of using hydroxy methyl phenylacetic acid lactone as raw material to react with TBN (tributyrin), absolute methanol and sodium methoxide to obtain (E)-3-keto-4-(isonitroso)isochroman; using the (E)-3-keto-4-(isonitroso)isochroman to react with acetone and potassium carbonate, and dropwise adding the acetone solution of dimethyl sulfate after a large amount of bright yellow solids occurs, so as to obtain (E)-3-keto-4-(methoxyimino)isochroman; dissolving the obtained (E)-3-ketone-4-(methoxyimino)isochroman by methanol, and dropwise adding thionyl chloride under the low-temperature condition to prepare (E)-2-chlororated methyl-alpha-methoxyimino methyl phenylacetate; after the catalysis of 3-(trifluoromethyl)acetophenone and hydroxylamine hydrochloride, using absolute ethyl alcohol and as solvent to obtain light earthy yellow solid (E)-3-(trifluoromethyl)acetophenone oxime; enabling the (E)-2-bromomethyl-alpha-methoxyimino methyl phenylacetate and the (E)- 3-(trifluoromethyl)acetophenone oxime to react in a DMF (dimethyl formamide) solution of the potassium hydroxide, so as to obtain the white solid of trifloxystrobin.
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- AN IMPROVED PROCESS FOR THE SYNTHESIS OF STROBILURIN FUNGICIDES VIZ TRIFLOXYSTROBIN AND KRESOXIM-METHYL
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The present invention relates to an improved process for the synthesis of E-isomer of compound of formula (5). It further relates to the conversion of formula (5), wherein R is H, to Intermediate (I) and subsequently to substantially pure Trifloxystrobin, compound of formula (I) in good yield.
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- Synergistic Active Compound Combinations Comprising Phenyltriazoles
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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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- 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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- Pyrazolyl benzyl ether derivatives containing a fluoromethoxyimino group and use thereof as pesticides
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The invention relates to novel pyrazolyl benzyl ethers, to a plurality of processes for their preparation and to their use for controlling harmful organisms.
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- Protective agents for wood
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Solvent-free coating materials and treating agents used as water-based wood or material protective agents containing emulsifiable binding agents, quaternary ammonium compounds and optional additional active agents. The wood or material protective agents are non-flammable and enable a uniform distribution of the binding agent and the quaternary ammonium compounds in the substrates. As a result, the quaternary ammonium compounds function as a dissolving mediator for the binding agents which are dispersed in water without opacifying effects and are used as a biocide. The agents can additionally absorb water-insoluble organic biocides without impairing the homogeneity or stability of the formulation of the homogeneity of the distribution in the substrate.
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- Wood preservatives
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Wood preservatives having biocidal properties which include quaternary ammonium compounds of general formula (I): wherein R1 is a C8-18-alkyl group or an optionally substituted benzyl group, R2 is a C8-18-alkyl group, R3 is a C1-4-alkyl group or a group of the formula —[CH2—CH2—O]n—H, R4 is a C1-4-alkyl group, n is a number from 0.5 to 8, preferably from 1 to 5, and A?is the anion of an organic carboxylic acid which contains 2 to 12 C atoms and carries at least one hydroxyl, amino or sulfonic acid group. The wood preservatives also penetrate deeply into the wood without the use of pressure, and have only a mild corrosive action on metals. Furthermore, a process for treating timbers with these compositions, concentrates for the preparation thereof, the use of new and known quaternary ammonium compounds in wood preservatives and new quaternary ammonium compounds and their use as biocides.
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- Synthesis of 8-substituted 5H,9H-6-oxa-7-azabenzocyclononene- 10,11- dione- 11-O-methyloximes, a new [1,2]-oxazonine ring system
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Reaction of (2-bromomethyl-phenyl)-methoxyimino-acetic acid methyl ester 4 with oximes 1 in the presence of NaH/DMF yields 8-substituted 5H,9H-6-oxa- 7-aza-benzocyclononene-10,11-dione-11-O-methyloximes 3 together with the expected open chain compounds 2. Some spectroscopic data as well as synthetic and mechanistic aspects of the formation of the novel compounds 3 are discussed. (C) 2000 Elsevier Science Ltd.
- Pascual, Alfons,Ziegler, Hugo,Trah, Stephan,Ertl, Peter,Winkler, Tammo
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p. 1381 - 1384
(2007/10/03)
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- Iminoacetic acid amides and their use as pest control agents
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PCT No. PCT/EP96/04345 Sec. 371 Date Apr. 15, 1998 Sec. 102(e) Date Apr. 15, 1998 PCT Filed Oct. 7, 1996 PCT Pub. No. WO97/14673 PCT Pub. Date Apr. 24, 1997Iminoacetamides of the formula (I) in which A represents a single bond or optionally substituted alkylene, Q represents oxygen or sulphur, R1 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R2 represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R3 represents hydrogen or respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl, R4 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclcyl a process for their preparation, pesticidal compositions containing them, and their use for controlling pests.
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- Patch preparations for treating plants
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The following invention introduces a patch preparation for treating plants, whereas the patch preparations comprise a chemical layer composed of at least one agrochemically active compound, at least one adhesive and optionally, one or more additives. The components are dispersed in a matrix state on a substrate which are then introduced on the roots of the plant to be treated.
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- Method for the treatment of plants with agrochemical tablet compositions
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Novel method for applying agrochemicals to plants, which method consists in attaching to the surface of the plants tablets comprising at least one agrochemically active compound and at least one adjuvant, which is solid, liquid of pasty at room temperature, and optionally, one or more excipients optionally in admixture with one or more other additives and/or water.
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- Pesticidal compositions in paste form
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Novel pasty compositions for the control of animal pests and fungal diseases on plants, which compositions comprise at least one pesticidally active or fungicidally active compound and at least one adjuvant, which is solid, liquid or pasty at room temperature and optionally, one or more excipients and water.
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- Microbicidal benzotriazoles
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Novel benzotriazoles of the formula STR1 in which R, X1, X2, X3, X4 and Y have the meanings given in the description, and their acid addition salts and metal salt complexes, a process for the preparation of these substances and their use as microbicides in crop protection and in material protection.
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- Halogen alkenyl azolyl microbicides
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Novel halogenoalkenyl-azolyl derivatives of the formula STR1 in which R1 represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted aryl or represents optionally substituted heteroaryl, R2 represents alkyl, halogenoalkyl, 1-hydroxyalkyl, 2-hydroxyalkyl, 1-hydroxyhalogenalkyl, 1-alkenyl or 2-alkenyl, X1 represents fluorine, chlorine, bromine or iodine, X2 represents fluorine, chlorine, bromine or iodine, and Y represents nitrogen or a CH group, and addition products thereof with acids or metal salts are very active as microbicides in plant protection and in the protection of materials.
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- Acylated 5-aminopyrazoles and the use thereof to combat animal parasites
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The present invention relates to new acylated 5-aminopyrazoles of the formula (I) STR1 in which R1, R2, R3, R4 and R5 have the meaning given in the description, to processes for their preparation and to their use as pesticides.
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- Agrochemical formulations for water surface application
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New agrochemical formulations for application to the water of paddy fields, which formulations comprise A) at least one solid core material having an apparent specific density of less than 1 and a particle diameter within the range from about 300 μm to about 1,400 μm, and B) a coating layer comprising at least one biologically active compound, at least one substance having the ability to reduce the interfacial tension between water and air, at least one oily substance and, if appropriate, one or more additives, and the use of such agrochemical formulations for applying biologically active compounds to the water of paddy fields.
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- Substituted tetrahydro-5-nitro-pyrimidines
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The present invention relates to novel substituted in that one tetrahydro-5-nitro-pyrimidine of the formula (I), according to claim 1, STR1 in which n, R1, R2 have the meaning given in the description, to a process for its preparation and to its use for combating animal pests, especially insects, arachnids and nematodes, which are encountered in agricultural, in forestry, in the protection of stored products and of materials and, in the hygiene sector.
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- P-hydroxyaniline derivatives, their preparation and their use
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p-Hydroxyaniline derivatives of the formula I STR1 where the substituents have the following meanings: R1 is unsubstituted or substituted bicycloalkyl or bicycloalkenyl; R2 and R3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy; R4 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, OR5 or NR5 R6, where R5 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, and R6 is hydrogen or alkyl, and their salts, processes for their preparation, compositions containing them and their use for controlling harmful fungi or pests are described.
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- Use of diphenyl ether derivatives for the desiccation and abscission of plant organs
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The use of diphenyl ether derivatives of the general formula I STR1 where A is a radical STR2 where R1 is hydrogen, an alkali metal or alkaline earth metal ion, substituted or unsubstituted ammonium, alkyl of from 1 to 4 carbon atoms or alkoxycarbonylalkyl of a total of 1 to 6 carbon atoms and R2 is alkyl of from 1 to 4 carbon atoms, for the desiccation and abscission of plant organs.
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- Oil-in-water emulsions, and their use
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Novel oil-in-water emulsions, which contain (a) 0.1 to 80% by weight of at least one sparingly water-soluble active compound (as herein defined) selected from agrochemical active compounds, active compounds for combating pests in the domestic field and hygiene field and/or pharmacologically active compounds, (b) 1 to 20% by weight of at least one alkylaryl polyglycol ether of the general formula STR1 wherein R1 represents a hydrogen atom or an alkyl group having 1 to 16 carbon atoms, R3 represents a hydrogen atom or a methyl group, m is 1, 2 or 3, and n is an integer from 10 to 50, if appropriate in a mixture with an alkylarylsulphonic acid salt of the general formula STR2 wherein R3 represents an alkyl group having 8 to 35 carbon atoms and Me≈ represents an alkali metal cation, an equivalent of an alkaline earth metal cation or a cation of the general formula STR3 wherein R', R", R'" and RIV independently of one another represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a hydroxyalkyl group having 1 to 4 carbon atoms, (c) water, (d) if necessary, 1 to 30% by weight of at least one poorly water-miscible organic solvent and/or a solubilizer, and (e) if appropriate 0.05 to 15% by weight of one or more additives, the sum of the components being 100% by weight in each case, a process for the preparation of these emulsions and their use in the field appropriate to the active compound.
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- Preparation of 3,3-dimethyl-1-phenoxy-butan-2-ols as fungicide intermediates
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3,3-Dimethyl-1-phenoxy-butan-2-ols of the formula STR1 in which Y is a halogen atom, an optionally substituted phenyl radical, an optionally substituted phenoxy radical or a nitro, cyano, alkyl, alkoxy, alkoxycarbonyl or cycloalkyl radical, and n is 0, 1, 2 or 3, exhibit plant growth stimulating properties and are also useful in the synthesis of known fungicides. They are produced from tert-butyloxirane and the corresponding phenols.
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- Combating fungi with 1-azol-1-yl-1-phenoxy-2-alkane ethers
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Azolyl ether derivatives of the formula STR1 in which A is CH or a nitrogen atom, R is alkyl, alkenyl, alkynyl, phenyl, benzyl or substituted phenyl or benzyl, X is halogen, alkyl, alkoxy, alkylthio, alkylsulphonyl, halogenoalkyl, alkoxycarbonyl, nitro, cyano, phenyl, phenoxy, phenylthio, or substituted phenyl, phenoxy of phenylthio, Y is alkyl, phenyl, or substituted alkyl or phenyl and n is 0, 1, 2, 3, 4 or 5, which possess fungicidal properties.
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- Antimicrobial agents and their use
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The invention involves the provision of compositions containing a 3,3-dialkyl- or 3-aryl-phenoxy-1-(1,2,4-triazol-1-yl)- and (imidazol-1-yl-alkan-2-ol) ethers which are particularly effective as antimicrobial especially antimycotic, agents. The invention also includes use of said compositions for providing antimicrobial, particularly antimycotic effect.
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