Cycloprothrin 乙氰菊酯

乙氰菊酯

CAS号：63935-38-6
英文名称：cycloprothrin
化学名称：；（RS）-α-氰基-3-苯氧苄基-（RS）-2，2-二氯-1（4-乙氧基苯基）环丙烷羧酸；(RS)-α-cyano-3-phe-noxybenzy(RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclo propanecarboxylate
其他名称：赛乐收，稻虫菊酯；杀螟菊酯
分子式：C26H21Cl2NO4
分子量：482.36

理化性质：纯品为透明粘稠液体。密度1.256，沸点140～145℃（0．13Pa）、180～184℃（1．33Pa），蒸气压213.3×10-8帕（20℃）。溶懈度（25℃）：水0.091mg／L，在有机溶剂中溶解度（g/L)：丙酮大于2000、甲醇467、乙醇101、氯仿＞2000、已烷26、苯＞2000、二甲苯2000、乙醚＞2000、乙酸乙酯、甲苯＞2000。稳定性：＜190℃稳定，对光和酸性介质中稳定，在碱性溶液中不稳定，在稻田土壤中DT50约4天。

毒性LD50（mg/kg）：按我国农药毒性分级标准，乙氰菊酯属低毒杀虫剂。雄、雌大、小鼠急性经口LD50均在5000以上，鸡、日本鹌鹑分别大于2000、5000。急性经皮2000以上，大鼠急性吸入LC50（4h）大于1.5mg/L空气。原药对皮肤和眼睛无刺激作用，2％颗粒剂和1%粉剂则有中等刺激作用。无致畸、致癌、致突变作用。鱼毒LC50(48h,mg/L)：鲤鱼大于50、金鱼大于10、虹鳟1.57。对蜜蜂和蚕有毒。90天饲喂试验中，大鼠无作用剂量为100mg/kg饲料，大米中允许残留量为0.1mg/kg。乙氰菊酯是替代禁用高毒有机磷农药的推荐品种。

作用特点及用途：本品属拟除虫菊酯类杀虫剂，具有触杀活性，几乎无胃毒作用，能抑制产卵。能有效地防洽二化螟、斜纹夜蛾、小莱蛾、菜粉蝶、褐带卷叶蛾、黑尾叶蝉、桃蚜、稻根象、稻象甲、二十八星瓢虫等、对有机磷和氨基甲酸酯类杀虫剂产生抗性的黑尾叶蝉品系，其活性高于敏感品系。叶面喷雾50mg／L,可长期抑制桃蚜繁殖，防洽桃小食心虫的施药浓度为100mg/L，防治甘蓝、白菜上的菜膏虫、小菜蛾、甘蓝夜蚜、蚜虫和大豆上的春蟓类害虫，十药浓度为100～250mg/L；防治水稻螟虫、叶蝉、稻象甲等，施药量为10～13.3g／亩、防治室内卫生害虫时，要加人少量苯醚菊酯。本品也能防治茶树和果树上的害虫。

剂型： 10%赛乐收乳油和2%赛乐收颗粒剂　，　10%赛乐收乳油　

生产方法：拟除虫菊酯类农药的合成一般分为两部分，酸的合成和醇的合成。

醇的合成以间苯氧基苯甲醛（俗称醚醛）为原料与亚硫酸钠加成生成相应的羟基磺酸钠，再与氰化钠反应生成α-氰基间苯氧基苯甲醇。

酸的合成以对羟基苯乙酸为起始原料，经与硫酸二乙酯反应生成对乙氧基苯乙酸乙酯，再经缩合、水解反应，再与甲醛、氯仿反应，再生成2，2-二氯-1-（4-乙氧苯基）环丙烷羧酸。

最后醇与酸缩合生成菊酯化合物。

生产情况：乙氰菊酯国际上主要生产厂家是日本化药公司（Nippon kagaku K.K），产量约20吨/年，国内安徽华星化工，扬农化工有生产。

cycloprothrin
Insecticide
IRAC 3; pyrethroid

NOMENCLATURE
Common name cycloprothrin (BSI, draft E-ISO); cycloprothine ((f) draft F-ISO)
IUPAC name (RS)-a-cyano-3-phenoxybenzyl (RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate
Chemical Abstracts name cyano(3-phenoxyphenyl)methyl 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate
CAS RN [63935-38-6] unstated stereochemistry Development codes GH-414 (CSIRO); NK-8116 (Nippon Kayaku) Official codes OMS 3049

PHYSICAL CHEMISTRY
Mol. wt. 482.4 M.f. C26H21Cl2NO4 Form Yellow to brown viscous liquid (tech.). B.p. 140-145 ºC/0.001 mmHg V.p. 2.13 ´ 10-3 mPa (20 ºC) KOW logP = 4.19 S.g./density 1.256 (25 ºC) Solubility In water 0.091 mg/l (25 ºC). Readily soluble in most organic solvents, but only moderately soluble in aliphatic hydrocarbons. Stability Stable £190 ºC and to light.

COMMERCIALISATION
History Insecticide invented at CSIRO and reported by G. Nolan et al. (Nature (London), 1978, 272, 734), and its development described by S. Kirihara & Y. Sakurai (Jpn. Pestic. Inf., 1988, No. 53, 22). Introduced in Japan (1987) by Nippon Kayaku Co., Ltd. Manufacturers Nippon Kayaku

APPLICATIONS
Biochemistry Acts on the nervous system of insects, disturbs the function of neurons by interaction with the sodium channel. Mode of action Insecticide with contact and stomach action. Also exhibits antifeeding and repellent activities. Uses Control of rice water weevils (Lissorhoptrus oryzophilus) and other insects in paddy rice, fruit, vegetables, tea, cotton, soya beans, and in forestry. Applied at 20-40 g/ha. Formulation types DP; EC; GR. Selected products: 'Cyclosal' (Nippon Kayaku)

ANALYSIS
Product and residue analysis by glc.

MAMMALIAN TOXICOLOGY
Reviews J. Pestic. Sci., 16, 697-702 (1991). Oral Acute oral LD50 for rats and mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg; no skin or eye irritation by tech., moderate irritation by GR and DP. Inhalation LC50 (4 h) for rats >1.5 mg/l air. NOEL (101 w) for rats 20 ppm. Other No teratogenic, carcinogenic or reproductive effects in rats in lifetime tests. Toxicity class WHO (a.i.) U

ECOTOXICOLOGY
Birds Acute oral LD50 for Japanese quail >5000, hens >2000 mg/kg. Fish LC50 (48 h) for carp >50, goldfish >10, rainbow trout 1.6 mg/l. Daphnia LC50 (3 h) >10 mg/l. Bees Toxic to honeybees.

ENVIRONMENTAL FATE
Animals In continual oral administration to rats, cycloprothrin is rapidly and completely excreted in urine and faeces (K. Seguchi et al., J. Pestic. Sci., 16, 591-598 (1991)). Plants For metabolism in rice plants, see K. Seguchi et al., J. Pestic. Sci., 16, 599-607 (1991). Soil/Environment When cycloprothrin was applied to simulated paddy water, the concentration absorbed in rice plants increased with time to a maximum within 7 days. The concentration was very low, and unchanged cycloprothrin was not found in the grain.