N-去甲基噻虫嗪

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: N-去甲基噻虫嗪
• 英文名称: N-desmethyl thiamethoxam
• 英文别名: N-Desmethylthiamethoxam, analytical standard；N-[3-[(2-chloro-1,3-thiazol-5-yl)methyl]-1,3,5-oxadiazinan-4-ylidene]nitramide
• 化学式: C₇H₈ClN₅O₃S
• 分子量: 277.691
• InChiKey: LOXCNVOJGRNBFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-去甲基噻虫嗪 在 sodium hydride 、 氯甲基丙基醚 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 0.25h， 以29%的产率得到3-(2-chloro-thiazol-5-yl-methyl)-4-nitroimino-5-n-propoxymethyl-perhydro-1,3,5-oxadiazine
  参考文献：
  名称：

  Cyclic guanidine derivatives and their use as pesticides

  摘要：

  本发明涉及一种新的胍衍生物，其化学式为(I)，其中A、R1、R2、R3和Z如描述中所定义，以及其制备方法和用于控制动物害虫的用途。

  公开号：

  US06683028B1
• 作为产物：
  描述：

  2-氯-5-氯甲基噻唑 、 4-nitroimino-1,3,5-oxadiazinane 在 吡啶 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到N-去甲基噻虫嗪
  参考文献：
  名称：

  Synthesis and Properties of Thiamethoxam and Related Compounds

  摘要：

  新烟碱类杀虫剂是最成功的化学类杀虫剂之一，其销售额在2003年达到了10亿美元以上，主要是由于咪唑烟碱和噻虫嗪的市场表现优异。本文描述了噻虫嗪及其相关化合物的发现、合成和杀虫活性，并报告了噻虫嗪的水解稳定性和降解途径，以及降解产物的合成。

  DOI：

  10.1515/znb-2006-0401

文献信息

• PESTICIDAL COMPOSITIONS
  申请人：Syngenta Participations AG

  公开号：EP0900024B1

  公开（公告）日：2003-06-18
• The discovery of thiamethoxam: a second-generation neonicotinoid
  作者：Peter Maienfisch、Hanspeter Huerlimann、Alfred Rindlisbacher、Laurenz Gsell、Hansruedi Dettwiler、Joerg Haettenschwiler、Evelyne Sieger、Markus Walti

  DOI：10.1002/1526-4998(200102)57:2<165::aid-ps289>3.0.co;2-g

  日期：2001.2

  Neonicotinoids represent a novel and distinct chemical class of insecticides with remarkable chemical and biological properties. In 1985, a research programme was started in this field, in which novel nitroimino heterocycles were designed, prepared and assayed for insecticidal activity. The methodology for the synthesis of 2-nitroimino-hexahydro-1,3,5-triazines, 4-nitroimino-1,3,5-oxadiazinanes and 4-nitroimino-1,3,5-thiadiazinanes is outlined. Bioassays demonstrated that 3-(6-chloropyridin-3-ylmethyl)-4-nitroimino-1,3,5-oxadiazinane exhibited better insecticidal activity than the corresponding 2-nitroimino-hexahydro-1,3,5-triazine and 4-nitroimino-1,3,5-thiadiazinane. In most tests, this compound was equally or only slightly less active than imidacloprid. A series of structural modifications on this lead structure revealed that replacement of the 6-chloro-3-pyridyl group by a 2-chloro-5-thiazolyl moiety resulted in a strong increase of activity against chewing insects, whereas the introduction of a methyl group as pharmacophore substituent increased activity against sucking pests. The combination of these two favourable modifications led to thiamethoxam (CGA 293 343).Thiamethoxam is the first commercially available second-generation neonicotinoid and belongs to the thianicotinyi sub-class. It is marketed under the trademarks Actara(R) for foliar and soil treatment and Cruiser(R) for seed treatment. The compound has broad-spectrum insecticidal activity and offers excellent control of a wide variety of commercially important pests in many crops. Low use rates, flexible application methods, excellent efficacy and the favourable safety profile make this new insecticide well-suited for modern integrated pest management programmes in many cropping systems. (C) 2001 Society of Chemical Industry.
• PESTICIDAL COMPOSITION
  申请人：Novartis AG

  公开号：EP0915656A1

  公开（公告）日：1999-05-19
• Pesticidal composition
  申请人：——

  公开号：US20030166618A1

  公开（公告）日：2003-09-04

  Composition for controlling insects and representatives of the order Acarina, which comprises a combination of variable amounts of one or more compounds of the formula 1 in which A is an unsubstituted or, depending on the possibility of substitution on the ring system, mono- to tetrasubstituted, aromatic or non-aromatic monocyclic or bicyclic heterocyclic radical, in which the substituents of A are chosen from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy, halogen, halo-C 1 -C 3 alkyl, cyclopropyl, halocyclopropyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, halo-C 2 -C 3 alkenyl, halo-C 2 -C 3 alkynyl, halo-C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylthio, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro; R is hydrogen, C 1 -C 6 alkyl, phenyl-C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl; and X is N—NO 2 or N—CN, in the free form or in salt form, if appropriate tautomers, in the free form or salt form, and one or more of the compounds: azamethiphos; chlorfenvinphos; cypermethrin, cypermethrin high-cis; cyromazin; diafenthiuron; diazinon; dichlorvos; dicrotophos; dicyclanil; fenoxycarb; fluazuron; furathiocarb; isazofos; jodfenphos; kinoprene; lufenuron; methacriphos; methidathion; monocrotophos; phosphamidon; profenofos; diofenolan; a substance obtainable from a Bacillus thuringiensis strain; pymetrozine; bromopropylate; methoprene; disulfuton; quinalphos; tau-fluvalinate; thiocyclam; or thiometon and at least one auxiliary; a method of controlling pests, a process for the preparation of the composition, its use and plant propagation material treated with it, and the use of the compound of the formula (A) for the preparation of the composition are described.
• Method of controlling termites
  申请人：Reid L. Byron

  公开号：US20070157507A1

  公开（公告）日：2007-07-12

  A method for controlling termites comprising applying at a locus a particulate termiticidal composition in the substantial absence of water.