N-[1-[(2-Chloro-1,3-Thiazol-5-yl)Methyl]-5-Propyl-1,3,5-Triazinan-2-Ylidene]Nitramide置于盐酸,Potassium Carbonate体系中,用 乙醇,N,N-二甲基甲酰胺 用作溶剂,化学反应 24.0H,反应生成噻虫胺 参考文献:A Novel Method For The Preparation Of N,N'-Disubstituted-N''-Nitroguanidines,Including A Practical Synthesis Of The Neonicotinoid Insecticide Clothianidin 标题:A Novel Method For The Preparation Of N,N'-Disubstituted-N''-Nitroguanidines,Including A Practical Synthesis Of The Neonicotinoid Insecticide Clothianidin 摘要:A Novel Method Is Described For The Synthesis Of N,N'-Disubstituted-N"-Nitroguanidines 3 Via 2-Nitroiminohexahydro-1,3,5-Triazine Intermediates 12,Allowing The Introduction Of The Heteroarylmethyl Group Either From A Heteroarylmethyl Amine 9 Or A Heteroarylmethyl Chloride 14,Respectively. This Method Enables An Efficient Synthesis Of The Neonicotinoid Insecticide Clothianidin (3B) In Four Steps From S-Methyl-N-Nitroisothiourea (10). (C) 2000 Elsevier Science Ltd. All Rights Reserved. Doi:10.1016/s0040-4039(00)01225-9
专利号:WO-2025056767-A1 优先权日:2023-09-15 标题 :Process for the preparation of enantiomerically enriched aliphatic amines 发明人:BOU HAMDAN FARHAN; GODINEAU EDOUARD; SMEJKAL TOMAS; DUMEUNIER RAPHAEL; BOUSSEMGHOUNE MOHAMED ABDELOUAHAB; BLUM MATHIAS 权利人:SYNGENTA CROP PROTECTION AG 摘要:The present invention relates to a process for the preparation of enantiomerically enriched cyclobutylamines of formula (I) from α-tertiary cyclobutanones and reacting said enantiomerically enriched cyclobutylamines to enantiomerically enriched cyclobutylamides. Such compounds are useful intermediates in the synthesis of microbiocidal thiazole compounds.
专利号:US-2016073631-A1 优先权日:2013-03-04 标 题 :Process for the preparation of dihydropyrrole derivatives 发明人:EL QACEMI MYRIEM; SMITS HELMARS; CASSAYRE JEROME YVES; MULHOLLAND NICHOLAS PHILLIP; RENOLD PETER; GODINEAU EDOUARD; PITTERNA THOMAS 权利人:SYNGENTA PARTICIPATIONS AG; SYNGENTA LTD 摘要:The present invention provides stereoselective processes for the preparation of compounds of formula (I) n n n n n n n n n n n n wherein n P is phenyl, naphthyl, a 6-membered heteroaryl group containing one or two nitrogen atoms as ring members, or a 10-membered bicyclic heteroaryl group containing one or two nitrogen atoms as ring members, and wherein the phenyl, naphthyl and heteroaryl groups are optionally substituted; n R 1 is chlorodifluoromethyl or trifluoromethyl; n R 2 is optionally substituted aryl or optionally substituted heteroaryl; n n is 0 or 1; n including the process comprising n (a-i) reacting a compound of formula II n n n n n n n n n n n n n n n n wherein P, R 1 and R 2 are as defined for the compound of formula I; n with nitromethane in the presence a chiral catalyst to give a compound of formula III n n n n n n n n n n n n n n n n wherein P, R 1 and R 2 are as defined for the compound of formula I; and n (a-ii) reductively cyclising the compound of formula III to give the compound of formula I. n n n n n The invention also provides intermediates useful for processes for the synthesis of compounds of formula (I).
专利号:US-10202620-B2 优先权日:2014-05-16 标 题:Synthesis of olefinic alcohols via enzymatic terminal hydroxylation 发明人:COELHO PEDRO; CHEN MIKE M Y; MEINHOLD PETER; CHO CATHERINE MEE-HIE; BUI VU; HEEL THOMAS 权利人:PROVIVI INC 摘要:In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.
专利号:US-9233920-B2 优先权日:2010-06-11 标题 :Process for the preparation of dihydropyrrole derivatives 发明人:EL QACEMI MYRIEM; SMITS HELMARS; CASSAYRE JEROME YVES; MULHOLLAND NICHOLAS PHILLIP; RENOLD PETER; GODINEAU EDOUARD; PITTERNA THOMAS 权利人:EL QACEMI MYRIEM; SMITS HELMARS; CASSAYRE JEROME YVES; MULHOLLAND NICHOLAS PHILLIP; RENOLD PETER; GODINEAU EDOUARD; PITTERNA THOMAS; SYNGENTA PARTICIPATIONS AG; SYNGENTA LTD 摘要:The present invention provides stereoselective processes for the preparation of compounds of formula (I) wherein P is phenyl, naphthyl, a 6-membered heteroaryl group containing one or two nitrogen atoms as ring members, or a 10-membered bicyclic heteroaryl group containing one or two nitrogen atoms as ring members, and wherein the phenyl, naphthyl and heteroaryl groups are optionally substituted; R 1 is chlorodifluoromethyl or trifluoromethyl; R 2 is optionally substituted aryl or optionally substituted heteroaryl; n is 0 or 1; including the process comprising (a-i) reacting a compound of formula II wherein P, R 1 and R 2 are as defined for the compound of formula I; with nitromethane in the presence a chiral catalyst to give a compound of formula III Wherein P, R 1 and R 2 are as defined for the compound of formula I; and (a-ii) reductively cyclizing the compound of formula III to give the compound of formula I. The invention also provides intermediates useful for processes for the synthesis of compounds of formula (I).
专利号:US-12344573-B2 优先权日:2018-07-16 标题:Synthesis of straight-chain lepidopteran pheromones through one- or two-carbon homologation of fatty alkenes 发明人:WAMPLER KEITH M; LEE CHOON WOO; ROZZELL DAVID 权利人:PROVIVI INC 摘要:Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.
专利号:US-11155505-B2 优先权日:2017-02-17 标题 :Synthesis of pheromones and related materials via olefin metathesis 发明人:WAMPLER KEITH M; BUI VU; ROZZELL DAVID; COELHO PEDRO; FLORUTI ARTHUR; ONDI LEVENTE; MEHDI HASAN; EROS GABOR 权利人:PROVIVI INC 摘要:Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.
1: Montiel-León JM, Munoz G, Vo Duy S, Do DT, Vaudreuil MA, Goeury K, Guillemette F, Amyot M, Sauvé S. Widespread occurrence and spatial distribution of glyphosate, atrazine, and neonicotinoids pesticides in the St. Lawrence and tributary rivers. Environ Pollut. 2019 Apr 2;250:29-39. doi: 10.1016/j.envpol.2019.03.125. [Epub ahead of print] doi: 10.1016/j.envpol.2019.03.099. [Epub ahead of print] doi: 10.1371/journal.pone.0214787. eCollection 2019. 5: Parte SG, Kharat AS. Aerobic Degradation of Clothianidin to 2-Chloro-methyl Thiazole and Methyl 3-(Thiazole-yl) Methyl Guanidine Produced by Pseudomonas stutzeri smk. J Environ Public Health. 2019 Mar 3;2019:4807913. doi: 10.1155/2019/4807913. eCollection 2019. 6: Morfin N, Goodwin PH, Hunt GJ, Guzman-Novoa E. Effects of sublethal doses of clothianidin and/or V. destructor on honey bee (Apis mellifera) self-grooming behavior and associated gene expression. Sci Rep. 2019 Mar 26;9(1):5196. doi: 10.1038/s41598-019-41365-0.
合成参考文献
摘要:USEPA/Office of Pesticide Programs; Pesticide Fact Sheet- Clothianidin (May 2003). Available from, as of November 7, 2018: 摘要: 摘要:80 FR 10006 (2/25/2015) 摘要: 摘要:Franke C et al; Chemosphere 29: 1501-14 (1994)