The discovery of thiamethoxam: a second-generation neonicotinoid.
The discovery of thiamethoxam: a second-generation neonicotinoid.
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DOI：
10.1002/1526-4998(200102)57:2
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发表时间：
2001-02
影响因子：
4.1
通讯作者：
P. Maienfisch;H. Huerlimann;A. Rindlisbacher;L. Gsell;Hansruedi Dettwiler;J. Haettenschwiler;Evelyne Sieger
中科院分区：
文献类型：
--
作者：
P. Maienfisch;H. Huerlimann;A. Rindlisbacher;L. Gsell;Hansruedi Dettwiler;J. Haettenschwiler;Evelyne Sieger
新烟碱类化合物代表了一类具有显著化学和生物学特性的新型和独特的化学杀虫剂。1985年，在这一领域开始了一项研究计划，其中设计、制备并测定了新的硝基亚氨基杂环的杀虫活性。概述了2-硝基亚氨基-六氢-1，3，5-三嗪、4-硝基亚氨基-1，3，5-恶二嗪和4-硝基亚氨基-1，3，5-噻二嗪的合成方法。生物活性测定表明，3-（6-氯吡啶-3-基甲基）-4-硝基亚氨基-1，3，5-恶二嗪烷比相应的2-硝基亚氨基-1，3，5-六氢-1，3，5-三嗪和4-硝基亚氨基-1，3，5-噻二嗪烷具有更好的杀虫活性。在大多数试验中，该化合物的活性与吡虫啉相当或仅略低于吡虫啉。对该先导结构的一系列结构修饰表明，用2-氯-5-噻唑基取代6-氯-3-吡啶基导致对咀嚼昆虫的活性强烈增加，而引入甲基作为药效团取代基增加了对吸吮害虫的活性。这两个有利的修改的组合导致噻虫嗪（CGA 293 343）。噻虫嗪是第一种市售的第二代类烟碱，属于噻虫啉亚类。它以用于叶面和土壤处理的商标Actara和用于种子处理的商标Cruiser销售。该化合物具有广谱杀虫活性，并对许多作物中的各种商业上重要的害虫提供优异的防治。低使用率、灵活的施用方法、优异的功效和有利的安全性使这种新杀虫剂非常适合许多种植系统的现代综合虫害管理方案。
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 thianicotinyl sub-class. It is marketed under the trademarks Actara for foliar and soil treatment and Cruiser 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.