The discovery of thiamethoxam: a second-generation neonicotinoid
| Autor: | Alfred Rindlisbacher, Hanspeter Huerlimann, Markus Walti, Joerg Haettenschwiler, Hansruedi Dettwiler, Peter Maienfisch, Evelyne Sieger, Laurenz Dr Gsell |
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| Rok vydání: | 2001 |
| Předmět: |
Integrated pest management
Insecticides Insect Control Anabasine Toxicology Neonicotinoids Soil Structure-Activity Relationship chemistry.chemical_compound Imidacloprid Oxazines Chemistry Agricultural Animals Molecular Structure Chemistry Imidazoles Pesticide Residues Neonicotinoid Water Biological activity General Medicine Plants Pesticide Nitro Compounds Thiazoles Insect Science Seed treatment Biological Assay Thiamethoxam Pharmacophore Agronomy and Crop Science |
| Zdroj: | Pest Management Science. 57:165-176 |
| ISSN: | 1526-4998 1526-498X |
| DOI: | 10.1002/1526-4998(200102)57:2<165::aid-ps289>3.0.co;2-g |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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