CAS: 69327-76-0; 2-(Tert-Butylimino)-3-Isopropyl-5-Phenyl-1,3,5-Thiadiazinan-4-One

该化合物是属于三丁基锡类的昆虫生长调节器(IGR),主要用于控制黑麦虫病虫害,如白蝇,叶片和植物,其作用是抑制合成,阻断鼻涕和蛋的生长,导致有效抑制害虫.Buprofezin展示了强大的跨鼠活动和残留效果,使之适合综合虫害管理方案.其选择性行动方式尽量减少对有益的昆虫的伤害,包括授粉者和自然捕食者.该化合物与包括稻米,柑橘和蔬菜在内的一系列作物相容.Buprofezin的低哺乳动物毒性和环境持久性进一步提高了其在可持续农业做法中的实用性.

结构式图片

欧盟法规

[ECHA物质ECHA物质C&L通报REACH预注册

上下游产品

tert-butyl isothi°Cyanate N-tert-butyl-N'-isopropylthiourea N-Chloromethyl-N-phenylcarbamoyl chloride N-methylaniline

合成工艺路线路线简述

    叔丁基异硫氰酸酯置于碳酸氢钠体系中,用 水,氯苯 作为反应溶剂,化学反应 6.5H,反应生成 噻嗪酮
    参考文献:一种噻嗪酮的制备方法
    标题:一种噻嗪酮的制备方法
    摘要:本发明提供了一种噻嗪酮的制备方法,包括步骤1):在酯化釜中加入硫氰酸钠和水至溶解;再加入叔丁醇和盐酸得到混酯,再经转位和催化反应得到异硫氰酸叔丁酯;步骤2):将异硫氰酸叔丁酯加入氯苯中搅拌,滴加异丙胺,得到1‑异丙基‑3‑叔丁基硫脲溶液;步骤3):N‑甲基苯胺加入氯苯中;顺次通光气和氯气,得到n‑氯甲基‑n‑苯基氨基甲酰氯的溶液;步骤4):碳酸氢钠加入水中,再加入氯苯中;加入1‑异丙基‑3‑叔丁基硫脲溶液;滴加n‑氯甲基‑n‑苯基氨基甲酰氯的溶液,经过过滤,分层,高真空蒸去氯苯,再经结晶,离心,干燥得到噻嗪酮.本申请的噻嗪酮的制备过程中取代平均收率达到90%以上,成品噻嗪酮含量达98.0%以上,且制备过程中无氨氮废水产生.

    海关参考信息

    专利信息


    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.
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    主要参考文献

    1. Elzaki MEA, Miah MA, Han Z. Buprofezin Is Metabolized by CYP353D1v2, a Cytochrome P450 Associated with Imidacloprid Resistance in Laodelphax striatellus. Int J Mol Sci. 2017 Nov 29;18(12):2564. doi: 10.3390/ijms18122564.

    合成参考文献


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    摘要:S132 | UJIGCAPCICCS | A GC-APCI-IMS-HRMS CCS Library from Izquierdo-Sandoval et al. (2022) | DOI:10.5281/zenodo.15831151
    摘要:Yao H, Jiang C, Ye G, Cheng J. [Insecticide resistance of different populations of white-backed planthopper, Sogatella furcifera (Horváth) (Homoptera:Delphacidae)]. Ying Yong Sheng Tai Xue Bao. 2002 Jan;13(1):101–5.
    参考文献:10.1016/j.chroma.2008.03.017
    摘要:Banerjee K, Patil SH, Dasgupta S, Oulkar DP, Patil SB, Savant R, Adsule PG. Optimization of separation and detection conditions for the multiresidue analysis of pesticides in grapes by comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry. J Chromatogr A. 2008 May 09;1190(1-2):350–7. doi: 10.1016/j.chroma.2008.03.017.
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