- Discovery of novel 3-{[(5,5-dimethyl-4,5-dihydroisoxazol-3-yl)sulfonyl]methyl}benzo[d]isoxazole analogs as promising very long chain fatty acids inhibitors
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Very long chain fatty acids (VLCFAs) are one of the most principal and promising targets for herbicides discovery. In order to explore and find novel VLCFAs inhibitors with higher herbicidal activity and improved crop safety, a variety of new 3-{[(5,5-dimethyl-4,5-dihydroisoxazol-3-yl)sulfonyl]methyl}benzo[d]isoxazole derivatives were reasonably designed and synthesized. The results of greenhouse experiments indicated that several compounds exhibited good herbicidal activity against Digitaria sanguinalis, Echinochloa crus-galli, and Setaria faberii at rates of 150 g ai/ha. Compounds g4 and h1 displayed promising herbicidal activity against D sanguinalis and E crus-galli at rates of 75 g ai/ha, which is better than commercial pyroxasulfone and S-metolachlor. Moreover, compound h1 displayed higher activity against E crus-galli, D sanguinalis, and S faberii than pyroxasulfone and S-metolachlor even at a rate of 37.5 and 18.75 g ai/ha. Furthermore, both of the compounds g4 and h1 were much safer to these tested crops, especially to rice, wheat and rape, at the rate of 150 g ai/ha than pyroxasulfone. Therefore, h1 may act as a new lead structure for novel herbicides discovery.
- Lin, Jian,Li, Yitao,Hu, Xiaoyun,Chi, Weilin,Zeng, Shuiming,Xu, Junxing
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p. 226 - 240
(2020/10/19)
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- ISOXAZOLINE DERIVATIVES AND THEIR USES IN AGRICULTURE
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Provided are isoxazoline derivatives and uses thereof in agriculture; in particular, provided a compound having formula (I), a stereoisomer, an N-oxide or a salt thereof, preparation methods thereof, and compositions containng these compounds and uses thereof in agriculture, particularly uses as active ingredients of herbicide for controlling unwanted plants; wherein R1, R2, R3, R4, n, R5, R6, Ra, Rb, Rc, Rd and Re are defined as described in the invention.
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Paragraph 00158
(2021/02/12)
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- Method for preparing pyroxasulfone intermediate 5, 5-dimethyl-4, 5-dihydroisoxazole-3-thioformamidine hydrochloride
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The invention relates to the field of pesticide herbicide synthesis, in particular to a method for preparing a sulfonylpyraflufen-ethyl intermediate 5, 5-dimethyl-4, 5-dihydroisoxazole-3-thioformamidine hydrochloride, which comprises the following steps: reacting a compound IV with strong acid to form salt to obtain a compound III; directly carrying out chlorination reaction on the compound III and chlorine without purification to obtain a chlorination product compound II; and reacting the compound II with thiourea in an organic solvent in the presence of inorganic acid to obtain a compound I. According to the method, the compound IV is used as a raw material, the raw material cost is low, salifying and chlorination are performed to obtain the product compound II, byproducts are few, reaction operation is easy and convenient, and pollution is small; AND finally, the compound I is prepared by directly reacting with thiourea in the presence of inorganic acid, the yield of a finished product is up to 90% or above, the purity can reach 99%, a used solvent can be completely recycled, and the method is very suitable for industrial production.
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Paragraph 0056-0057; 0063-0065; 0067-0068; 0070-0072
(2021/04/14)
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- Pyroxasulfone synthesis method
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The invention provides a pyroxasulfone synthesis method. The method comprises the steps of: adopting a compound I as a starting raw material, carrying out cyclization reaction to synthesize an intermediate II, and carrying out chlorination reaction on the intermediate II under the action of a chlorination reagent to obtain an intermediate III; reacting the intermediate III with thiourea to obtaina hydrochloride intermediate IV, wherein the chlorination reagent is phosphorus pentachloride and/or phosphorus oxychloride; reacting the hydrochloride intermediate IV and a compound VI with formaldehyde to obtain an intermediate VII, carrying out difluoromethoxylation reaction on the intermediate VII to obtain an intermediate VIII, and oxidizing the intermediate VIII with hydrogen peroxide in thepresence of a catalyst to obtain pyroxasulfone IX, wherein the catalyst is sodium tungstate and acid. According to the method, the total yield is increased to 31-38%, the raw materials are simple andeasily available, the reaction process is simple and safe, the yield is high, and the method has certain significance for industrial production.
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- Isoxazoline derivative and applications in agriculture
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The invention provides an isoxazoline derivative and applications in agriculture, specifically a compound represented by a formula (I) or a stereoisomer, a nitrogen oxide or a salt thereof, a preparation method of the compound, a composition containing the compound, and applications of the composition in agriculture, particularly application of the composition as a herbicide active ingredient in prevention and treatment of unwanted plants, wherein R, R, R, R, n, R, R, X and Cy are defined in the specification.
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Paragraph 0231; 0237-0240
(2020/03/25)
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- ISOXAZOLINE DERIVATIVES AND THEIR USES IN AGRICULTURE
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Provided are isoxazoline derivatives and uses thereof in agriculture; in particular, provided are a compound having formula (I), a stereoisomer, an N-oxide or a salt thereof, preparation methods thereof, and compositions containing these compounds and uses thereof in agriculture, particularly uses as herbicide active ingredients for controlling unwanted plants; wherein each of R1, R2, R3, R4, n, R5, R6, X and Cy is as described in the invention.
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Paragraph 00163
(2020/03/29)
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- Method for producing thiocarboxamidine salt compound
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The present disclosure provides an industrially preferable, economical, and environmentally friendly method for producing a compound [C1] of formula (5), namely, a (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound. The present disclosure relates to a method wherein: a reaction expressed by reaction formula [C2] is caused so as to produce a compound of formula (4) by reacting a compound of formula (3) with a halogenation agent in the presence of a nitrile solvent, and the compound of formula (4) is subsequently reacted with an isothiouronium-forming agent, thereby producing a compound of formula (5).
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Page/Page column 19-24
(2020/12/07)
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- PROCESS FOR PREPARATION OF PYROXASULFONE
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The present invention discloses a process for the preparation of Pyroxasulfone of Formula (I) or salt thereof. Particularly, the present invention discloses an improved process for the preparation of hydroxycarbonimidic dibromide compound of Formula (III) or salt thereof, wherein bromine anion is recycled by using a suitable oxidizing agent. Moreover, the present invention relates to a continuous flow process for preparing of compound of Formula (I) or salt thereof.
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Page/Page column 21-22
(2020/12/11)
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- ISOXAZOLINE DERIVATIVES AND THEIR USES IN AGRICULTURE RELATED APPLICATION
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The present invention provides isoxazoline derivatives and uses thereof in agriculture; in particular, the present invention provides a compound having formula (I), or a stereoisomer, an N-oxide or a salt thereof, preparation methods thereof, and compositions containing these compounds and uses thereof in agriculture, particularly uses as herbicide active ingredients for controlling unwanted plants; wherein R1, R2, R3, R4, n, R5, R6 and Hy are as described in the invention.
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Paragraph 00213
(2019/04/26)
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- A two-valence sulfonyl isoxazole derivatives and use thereof
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The invention discloses a bi-titer sulfonyl isoxazole derivative in the technical field of organic compound weedicides, and application thereof. The bi-titer sulfonyl isoxazole derivative has a molecular structural formula shown as a general formula I. The invention further discloses a preparation method of the bi-titer sulfonyl isoxazole derivative. The bi-titer sulfonyl isoxazole derivative has very high activity of inhibiting weed growth and killing and removing weeds, and can be used in agricultural production, and is classified as a novel active component for weedicides.
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Paragraph 0010; 0018; 0023-0024
(2017/10/07)
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- Method for Producing 5,5-Disubstituted 4,5-Dihydroisoxazol-3-Thiocarboxamidine Salts
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A process for preparing 5,5-disubstituted 4,5-dihydroisoxazole-3-thiocarboxamidine salts of the formula (I), wherein 3-unsubstituted 4,5-dihydroisoxazoles are first reacted with a chlorinating or brominating reagent to give 3-halogenated 4,5-dihydroisoxazoles and the latter then react with thiourea to give the compounds of the formula (I).
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Page/Page column 11
(2012/10/23)
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- Synthesis and herbicidal activity of novel N -(2,2,2)- trifluoroethylpyrazole derivatives
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A series of novel N-(2,2,2)-trifluoroethylpyrazole derivatives were synthesized, and their structures were characterized by IR, mass spectroscopy, 1H NMR, and elementary analysis. The herbicidal activities of target compounds 10a?c and 11a?c we
- Ma, Hong-Ju,Li, Yong-Hong,Zhao, Qian-Fei,Zhang, Tao,Xie, Ru-Liang,Mei, Xiang-Dong,Ning, Jun
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experimental part
p. 4356 - 4360
(2011/08/04)
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- PROCESS FOR PRODUCTION OF (4,5-DIHYDROISOXAZOL-3-YL)THIO- CARBOXAMIDINE SALTS
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To provide a method for producing a (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound simply, safely and in good yield, whereby drawbacks of prior art have been solved. A method for producing a (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound of the formula (2): wherein each of R1 and R2 which are independent of each other, is a hydrogen atom, an alkyl group or a cycloalkyl group, each of R3 and R4 which are independent of each other, is a hydrogen atom or an alkyl group, provided that R1 and R2, or R2 and R3, may be bonded to each other to form a cycloalkyl group together with the carbon atoms to which they are bonded, and X2 is a halogen or an anionic residue derived from an acid, which comprises reacting a 3-halogeno-4,5-dihydroisoxazole compound of the formula (1) : wherein R1, R2, R3 and R4 are as defined above, and X1 is a halogen, with thiourea in the presence of an acid.
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- HERBICIDAL ISOXAZOLINE COMPOUNDS
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Novel compounds of formula (I): wherein R1, R2, R3, R4, m, R5, R6, n and Y are as defined in claim 1; or N-oxides, salts and optical isomers thereof. Furthermore, the present invention relates to processes for preparing compounds of formula (I), to herbicidal compositions comprising them and to methods of using them to control plants or to inhibit plant growth.
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- PROCESS FOR PRODUCING 5-HYDROXY-4-THIOMETHYLPYRAZOLE COMPOUND
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A pyrazole compound represented by general formula (1) is reacted with a sulfur compound represented by general formula (2) in the presence of a base and formaldehyde, to thereby produce a 5-hydroxy-4-thiomethylpyrazole compound represented by general formula (3). The 5-hydroxy-4-thiomethylpyrazole compound may easily be produced in a good yield, by using such a process. Further, this process may easily provide the 5-hydroxy-4-thiomethylpyrazole compound under a mild condition in a single step, without using a special apparatus, an expensive catalyst, or a transition metal, etc. In addition, this process may be conducted substantially without producing a harmful waste which can be derived from a catalyst, etc., and therefore this process is friendly to the environment and industrially valuable.
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Page/Page column 13
(2008/06/13)
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- PROCESS FOR PRODUCTION OF (4,5-DIHYDROISOXAZOL-3-YL)THIO- CARBOXAMIDINE SALTS
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The invention provides a process for producing (4,5-dihydro- isoxazol-3-yl)thiocarboxamidine salts easily and safely in a high yield which is freed from the disadvantages of the prior art. Specifically, a process for producing (4,5-dihydro- isoxazol-3-yl)thiocarboxamidine salts represented by the general formula (2): (2) [wherein R1 and R2 are each hydrogen, alkyl, or the like; R3 and R4 are each hydrogen or alkyl; or R1 and R2 or R2 and R3 together with the carbon atom(s) to which they are bonded may form cycloalkyl; and X2 is halogen or an anionic residue derived from an acid] by reacting a 3-halogeno-4,5-dihydroisoxazole represented by the general formula (1): (1) [wherein R1, R2, R3 and R4 are each as defined above; and X1 is halogeno] with thiourea in the presence of an acid.
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Page/Page column 9-10
(2008/06/13)
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- Herbicide compositions
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A herbicidal composition which comprises i) an isoxazoline derivative represented by the following general formula (I) or its salt and ii) at least one compound selected from the Group A: Formula (I) wherein R1, R2, R3, R4, R5 and R6 are defined in the specification.
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Page/Page column 27
(2010/02/14)
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- ISOXAZOLINE DERIVATIVE AND HERBICIDE COMPRISING THE SAME AS ACTIVE INGREDIENT
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An isoxazoline derivative represented by the following general formula [I]: wherein R1 and R2 may be the same or different and are each an alkyl group; ???R3, R4, R5 and R6 are each a hydrogen atom; ???Y is an optionally substituted 5- to 6-membered aromatic heterocyclic group or fused aromatic heterocyclic group having a hetero atom selected from a nitrogen atom, a oxygen atom and a sulfur atom; and ???n is an integer of 0 to 2. The isoxazoline derivative has an excellent herbicidal effect and an excellent selectivity between crop and weed.
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Page/Page column 189-190
(2010/02/07)
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- ISOXAZOLINE DERIVATIVES AND HERBICIDES CONTAINING THE SAME AS THE ACTIVE INGREDIENT
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The isoxazoline derivative of the present invention is represented by the following general formula [I]: [wherein Q is a group represented by -S(O)n-(CR5R6)m- (wherein n is an integer of 0 to 2, m is an integer
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