Azinphos-methyl 甲基谷硫磷,保棉磷

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甲基谷硫磷

CAS编码: 86-50-0
Development Codes : Bayer
IUPAC名称: S-(3,4-dihydro-4-oxobenzo[d]-[1,2,3]-triazin-3-ylmethyl) O,O-dimethyl pho
英文通用名称: Azinphos-methyl
中文通用名称: 甲基谷硫磷
英文商品名称: Azinphos methyl;Azinphosmethyl;Bayer 17147;Carfene;Gusathion M;Guthion;R 1582;O,O-Dimethyl S-[(4-oxo
中文化学名:二硫代磷酸-O,O-二甲基-S-[(4-氧代-1,2,3-苯并三嗪-3-[4H]基)甲基]酯
中文商品名称: 谷硫磷;谷硫磷-M;谷赛昂;谷速松[台];酷杀星;保棉磷;甲基谷赛昂
英文化学名称: O,O-dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] phosphorodithi
分子式: C10H12N3O3PS2
分子量: 317.3

是一种具胃毒作用和触杀作用的有机磷杀虫剂。纯品是白色晶体,密度1.44,熔点73-74℃,折射率1.6115(76℃)。溶于大多数有机溶剂。难溶于水。用于防治棉花后期害虫,对棉铃虫有良好效果。也能杀螨。残效期长,杀虫谱广。有剧毒!使用时要注意安全。由O,O-二甲基二硫代磷酸钠与3-氯甲基-4-氧代-4H-1,2,3-苯并三嗪在丙酮中反应而制得。

储存条件 0-6°C
保棉磷(谷硫磷)是一种神经毒素,具有良好的杀虫效力,用于如草莓,夏日水果和马铃薯等作物的虫害防治,属于广谱有机磷杀虫剂。但是美国环保局认为,它对农场工人而言带有无法接受的风险并也在扩散到水里时杀死了鱼。美国环保局决定,2012年夏天之后任何人不得使用保棉磷。而樱桃种植者是最后一批使用保棉磷的农户之一。50年来,种植者一直依靠保棉磷使水果不受蠕虫和驱虫之害。保棉磷来源于一战的神经毒气。当他们喷洒保棉磷的时候,果园里的每只小虫子都必死无疑。一小部分种植者一直在试图寻找保棉磷的替代品。
新西兰环境风险管理局(ERMA)一直将保棉磷的使用评估作为更广泛的化合物审查的一部分,并决定在5年内将之逐步淘汰出市,该机构还将在这段时间内加强控制,以减少对人和环境造成的威胁。这些措施包括禁止国内使用或空中喷洒,并限制一年中的使用次数。ERMA称将淘汰期设定为5年是因为这是发展替代产品所需要的时间。
类别 农药
毒性分级 剧毒
急性毒性 口服-大鼠 LD50: 7 毫克/公斤; 口服-小鼠 LD50: 8.6 毫克/公斤
刺激数据 眼睛-兔子 24.4 毫克 重度
可燃性危险特性 明火可燃; 受热放出有毒氧化硫、氧化氮、氧化磷气体
储运特性 库房通风低温干燥; 与食品原料分开储运 种具胃毒作用和触杀作用的有机磷杀虫剂。纯品是白色晶体,密度1.44,熔点73-74℃,折射率1.6115(76℃)。溶于大多数有机溶剂。难溶于水。

 

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azinphos-methyl
Insecticide
IRAC 1B; organophosphate

  Azinphos-methyl

NOMENCLATURE
Common name azinphos-methyl (BSI, E-ISO, (m) F-ISO); azinphosmethyl (ESA); metiltriazotion * (former exception, USSR)
IUPAC name S-(3,4-dihydro-4-oxobenzo[d]-[1,2,3]-triazin-3-ylmethyl) O,O-dimethyl phosphorodithioate
Chemical Abstracts name O,O-dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] phosphorodithioate
CAS RN [86-50-0] EEC no. 201-676-1 Development codes Bayer 17 147; R 1582; E1582 Official codes ENT 23 233; OMS 186

PHYSICAL CHEMISTRY
Mol. wt. 317.3 M.f. C10H12N3O3PS2 Form Yellowish crystals. M.p. 73 ºC V.p. 5 ´ 10-4 mPa (20 ºC); 1 ´ 10-3 mPa (25 °C) KOW logP = 2.96 Henry 5.7 ´ 10-6 Pa m3 mol-1 (20 °C, calc.) S.g./density 1.518 (21 ºC) Solubility In water 28 mg/l (20 ºC). In dichloroethane, acetone, acetonitrile, ethyl acetate, dimethyl sulfoxide >250, n-heptane 1.2, xylene 170 (all in g/l, 20 ºC). Stability Rapidly hydrolysed in alkaline and acidic media; DT50 (22 ºC) 87 d (pH 4), 50 d (pH 7), 4 d (pH 9). Photodegrades on soil surfaces and readily photodegrades in water. Decomposes above 200 ºC.

COMMERCIALISATION
History Insecticide reported by E. E. Ivy et al. (J. Econ. Entomol., 1955, 48, 293). Developed by W. Lorenz and introduced by Bayer AG. European rights acquired by Makhteshim-Agan in 2002. Patents US 2758115; DE 927270 Manufacturers Bayer CropScience; General Quimica; Makhteshim-Agan

APPLICATIONS
Biochemistry Cholinesterase inhibitor. Mode of action Non-systemic, with contact and stomach action. Uses Control of chewing and sucking insects of the orders Coleoptera, Diptera, Homoptera, Hemiptera, and Lepidoptera, on fruit trees (including citrus), vines, strawberries, nuts, vegetables, potatoes, cereals, maize, cotton, ornamentals, beet, soya beans, tobacco, rice, coffee, sugar cane, forestry, and other crops. Phytotoxicity Russetting is possible on some fruit varieties with the emulsifiable concentrate formulation. Formulation types DP; EC; SC; WP. Compatibility Incompatible with alkaline materials. Selected products: 'Gusathion M' (Makhteshim-Agan, Bayer CropScience); 'Acifon' (General Quimica); 'Azín 200' (Ingeniería Industrial); 'Azinugec' (Sipcam Phyteurop); 'Cotnion-Methyl' (Makhteshim-Agan)

OTHER PRODUCTS
'Guthion' (Makhteshim-Agan, Bayer CropScience); 'Aziflo' (Chemia); 'Azin-PB' (Isagro); 'Crysthyon' (Crystal); 'Mezyl' (Papaeconomou); 'Sniper' (UAP); 'Supervelax' (IQV) Discontinued products: 'Valefos' * (Productos OSA)

ANALYSIS
Product analysis by lc (AOAC Methods, 17th Ed., 989.01, 7.7.02), by rplc (ibid., 989.01; CIPAC Handbook, 1992, E, 12) or by i.r. spectrophotometry (AOAC Methods, 17th Ed., 980.09; CIPAC Handbook, 1985, 1C, 1970) or by colorimetric measurement of the phosphorodithioate moiety as a complex (ibid., 1970, 1, 25; FAO Specification CP/4). Residues determined by glc (Analyst (London), 1977, 102, 858; A. Ambrus et al., J. Assoc. Off. Anal. Chem., 1981, 64, 733; D. H. MacDougall, Anal. Methods Pestic. Plant Growth Regul., 1972, 6, 397) or by spectrometry (AOAC Methods, 17th Ed., 961.12*, see 12th Ed., 29.102-29.107). Methods for the determination of residues are available from Bayer CropScience.

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 62, 64 (see part 2 of the Bibliography). Oral Acute oral LD50 for rats c. 9, male guinea pigs 80, mice 11-20, dogs >10 mg/kg. Skin and eye Acute percutaneous LD50 for rats 150-200 mg/kg (24 h); not a skin irritant; mild eye irritant (rabbits). Inhalation LC50 (4 h) for rats 0.15 mg/l air (aerosol). NOEL (2 y) for rats and mice 5 mg/kg diet; (1 y) for dogs 5 mg/kg diet. ADI (JMPR) 0.005 mg/kg b.w. [1991]. Toxicity class WHO (a.i.) Ib; EPA (formulation) I EC classification T+; R26/28| T; R24| R43| N; R50, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail c. 32 mg/kg. Dietary LC50 (5 d) for Japanese quail 935 mg/kg diet. Fish LC50 (96 h) for rainbow trout 0.02, golden orfe 0.12 mg/l. Daphnia LC50 (48 h) 0.0011 mg/l. Algae ErC50 (96 h) for Scenedesmus 7.15 mg/l. Bees Toxic to bees. Worms LC50 (14 d) 59 mg/kg. Other beneficial spp. Azinphos-methyl is an effective insecticide, therefore an effect on some non-target arthropods cannot be excluded, in particular, where those organisms are directly exposed to the spray treatment.

ENVIRONMENTAL FATE
EHC 63 (WHO, 1986; a general review of organophosphorus insecticides). Animals In mammals, following oral administration, >95% is eliminated in the urine and faeces within 2 days. The major metabolites are the monodesmethyl compound and benzazimide. Plants In plants, major metabolites identified include azinphos-methyl oxon, benzazimide, mercaptomethyl benzazimide and cysteinmethyl benzazimide. Soil/Environment Degradation involves oxidation, demethylation, and hydrolysis. Based on the Koc values and leaching studies, azinphos-methyl can be classified as a compound with low mobility. The half-life in soil is several weeks.