Clothianidin 噻虫胺

噻虫胺

中文通用名：噻虫胺
英文通用名：clothianidin
分子式：C6H8ClN5O2S
化学名称：(E)-1-(2-氯-1,3-噻唑-5-基甲基)-3-甲基-2-2-硝基胍
结构式：
理化性质：原药外观为结晶固体粉末，无嗅，熔点176.8℃。
蒸气压：1.3×10Pa(25℃)。溶解度：水0.327g/L，丙酮15.2 g/L，甲醇6.26 g/L，乙酸乙酯2.03 g/L，二氯甲烷1.32 g/L，二甲苯0.0128 g/L，正庚烷<0.00104 g/L，正辛醇0.938 g/L（测定温度：水25℃，有机溶剂20℃）。

毒性：急性经口LD50>5000mg/kg(雌/雄) 急性经皮LD50>2000mg/kg（雄/雌)

噻虫胺是新烟碱类中的一种杀虫剂，是一类高效安全、高选择性的新型杀虫剂，其作用与烟碱乙酰胆碱受体类似，具有触杀、胃毒和内吸活性。主要用于水稻、蔬菜、果树及其他作物上防治蚜虫、叶蝉、蓟马、飞虱等半翅目、鞘翅目、双翅目和某些鳞翅目类害虫的杀虫剂，具有高效、广谱、用量少、毒性低、药效持效期长、对作物无药害、使用安全、与常规农药无交互抗性等优点，有卓越的内吸和渗透作用，是替代高毒有机磷农药的又一品种。其结构新颖、特殊，性能与传统烟碱类杀虫剂相比更为优异，有可能成为世界性的大型杀虫剂品种。

新烟碱类杀虫荆噻虫胺(dothisnidJn)由拜耳公司和日本Takeda武田公司共同进行全球市场开发。该品种已在日奉用于水稻、果树、茶叶、草皮和观赏作物。clothianidin是武田公司继烯啶虫胺(nitenpyram)之后，发现的又一个烟碱类杀虫剂，属第二代，与第一代的nitenpyram 相比，其分子结构的主要差别为：一是用氯代噻唑基团取代了吡啶基团；二是用硝基亚胺取代了硝基亚甲基部分。5位上的甲基提高了对刺吸害虫的活性．而2一氯一5一噻唑基杂环则对咀嚼口器害虫产生更高的效果 。

目前国内外报道的合成方法主要有：(1)2-氯-5-氯甲基-1,3-噻唑与N-甲基-N/-硝基-S-甲基异硫脲反应；(2)2-氯-5-氯甲基-l，3-噻唑与N-甲基-N，-硝基脲反应；(3)2-氯-5-氯甲基-1，3-噻唑与N-硝基-S-甲基异硫脲反应。得到1-(2-氯-噻唑甲基)-N-硝基-S-甲基异硫脲，再甲胺化得到产物；(4)通过分解1-(2-氯噻唑-5-甲基) -2-硝基亚胺基-3,5-二甲基-六氢-1,3,5-三嗪制备产物。

clothianidin
Insecticide
IRAC 4A; neonicotinoid

NOMENCLATURE
Common name clothianidin (BSI, pa ISO)
IUPAC name (E)-1-(2-chloro-1,3-thiazol-5-ylmethyl)-3-methyl-2-nitroguanidine
Chemical Abstracts name (E)-N-[(2-chloro-5-thiazolyl)methyl]-N'-methyl-N''-nitroguanidine
CAS RN [210880-92-5]; (formerly [205510-53-8]) Development codes TI-435 (Takeda)

PHYSICAL CHEMISTRY
Mol. wt. 249.7 M.f. C6H8ClN5O2S Form Colourless, odourless powder. M.p. 176.8 °C V.p. 1.3 ´ 10-4 mPa (25 °C, EEC A4). KOW logP = 0.7 (25 °C) Henry 2.9 ´ 10-11 Pa m3 mol-1 (20 °C) S.g./density 1.61 (20 °C) Solubility In water 0.304 (pH 4), 0.340 (pH 10) (both g/l, 20 °C). In heptane <0.00104, xylene 0.0128, dichloromethane 1.32, methanol 6.26, octanol 0.938, acetone 15.2, ethyl acetate 2.03 (all in g/l, 25 °C). pKa 11.09 (20 °C)

COMMERCIALISATION
History Discovered by Takeda Chemical Industries (now Sumitomo Chemical Takeda Agro Company Ltd) and under development jointly with Bayer AG. Reported by Y. Ohkawara et al., Proc. BCPC Conf. - Pests Dis., 2002, 1, 51 and M. Schwarz et al., ibid., 59. Manufacturers Bayer CropScience; Sumitomo Chemical Takeda

APPLICATIONS
Biochemistry Agonist of the nicotinic acetylcholine receptor, affecting the synapses in the insect central nervous system. Mode of action Translaminar and root systemic activity. Uses Soil, foliar, paddy and seed insecticide, under development for control of sucking and chewing insects in rice, fruit and vegetables, maize and rape. Formulation types FS. Selected products: 'Dantotsu' (Sumitomo Chemical Takeda); 'Poncho' (Bayer CropScience, Sumitomo Chemical Takeda); 'Clutch' (Arvesta)

OTHER PRODUCTS
'Fullswing' (Sumitomo Chemical Takeda) mixtures: 'Dantotsupadan' (+ cartap hydrochloride) (Sumitomo Chemical Takeda); 'Dantotsupadanvalida' (+ validamycin+ cartap hydrochloride) (Sumitomo Chemical Takeda); 'Delausdantotsu' (+ diclocymet) (Sumitomo Chemical Takeda); 'Hustler' (+ ferimzone+ phthalide+ validamycin+ cartap hydrochloride) (Sumitomo Chemical Takeda); 'Windantotsu' (+ carpropamid) (Sumitomo Chemical Takeda)

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male and female rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >2000 mg/kg. Slightly irritating to eyes, not a skin irritant (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for male and female rats >6.1 mg/l. NOEL (2 y) for male rats 27.4, female rats 9.7 mg/kg b.w. daily; (1 y) for male dogs 7.8, female dogs 8.5 mg/kg b.w. daily. Other Not mutagenic. Not oncogenic in rats and mice. Not teratogenic in rats and rabbits.

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2000 mg/kg. Dietary LC50 for bobwhite quail and mallard ducks >5200 ppm. Fish LC50 (96 h) for rainbow trout >100, carp >100, bluegill sunfish >120 mg/l. Daphnia EC50 (48 h) >120 mg/l. Algae ErC50 (72 h) for Scenedesmus subspicatus >270 mg/l. Bees Harmful to honeybees by direct contact, but no problems expected when not sprayed into flowering crops, or when used as a seed treatment. Worms LC50 (14 d) 13.2 mg/kg soil.