Chlorpyrifos Methyl 甲基毒死蜱

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甲基毒死蜱

简介
【中文名称】甲基毒死蜱;甲基氯蜱硫磷;O,O-二甲基-O-3,5,6-三氯-2-吡啶基硫逐磷酸酯
【英文名称】chlorpyrifos-methyl;Reldan;Dowreldan; O,O-dimethyl O-3,5,6-trichloro-2-pyridyphosp-horothioate
【CA主题索引名及CAS登录号】
O,O-dimethyl O-(3,5,6-trichloro-2-pyridinyl)phosphorothioate(9CI)
O,O-dimethyl O-3,5,6-trichloro-2-pyridinylphosphorothioate(8CI)[5598-13-0]
R.H.Rigterink和E.E.Kenaga首先介绍其杀虫性,1966年由美国Dow Chemical Company 开发。

性质
【结构或分子式】
【相对分子量或原子量】322.47
【熔点(℃)】45.5~46.5
【性状】
纯品为白色结晶,具有轻微的硫醇味。
【溶解情况】
25℃水中溶解度为4mg/L,易溶于大多数有机溶剂。
【用途】
是一种广谱的有机磷杀虫剂,通过触杀、胃毒和熏蒸均有效,无内吸性,用于防治贮藏谷物中的害虫和各种叶类作物上的害虫,也可用来防治蚊成虫、蝇类、水生幼虫和卫生害虫。在土壤中无持效性。
【制备或来源】
吡啶在330℃、催化剂存在下,用氯气氯化,得五氯吡啶,而后以乙腈为溶剂,于78℃下缓慢滴加锌粉/氯化铵水溶液,反应3h,得2,3,5,6-四氯吡啶,然后在95~100℃、氢氧化钾存在下进行水解,用浓硫酸酸化至pH3.5,历时18h,得2-羟基-3,5,6-三氯吡啶,最后在其加热于氢氧化钠水溶液中溶解后,降温,加入少量氯化钠、氢氧化钠、硼酸、苄基三乙基氯化铵、1-甲基咪唑及二氯甲烷,42℃、搅拌下,加入O,O-二甲基硫代磷酰氯,加毕,回流1.5h,分离有机相,水洗、减压蒸除有机溶剂,即得甲基毒死蜱。制剂有:40%乳油。
【消耗定额(t/t)】
吡啶(工业品)0.60,O,O-二甲基硫代磷酰氯0.80。
【其他】
在一般贮藏条件下稳定,在中性pH6~8的介质中相对稳定,在酸性介质和碱性介质中易水解,在碱性条件下,水解速度较快。急性经口毒性LD50(mg/kg):雄大白鼠为2472,雌大白鼠为1828,雄小白鼠为2254,雌小白鼠为2032。大、小白鼠(雄、雌)急性经皮毒性LD50均大于2800mg/kg。允许残留量:米0.01mg/kg,蔬菜、甜菜0.03mg/kg。ADI为0.01mg/kg。

使用方法
1.贮粮害虫对有机械输送设备的粮库,可在粮食入库时在输送带上按4~10毫克/升的药剂量对食粮流进行喷雾,无输送设备时可按同样剂量药液人工喷雾拌和粮食,或用药剂砻糠载体法拌和粮食。对粮袋、仓墙可按每平方米0.5~1克有效成分 剂量喷雾处理。
2.对卫生害虫和作物害虫可采用喷雾处理。

注意事项
1、不能与碱性农药混用。
2、按规定剂量防治贮粮害虫,仅限于处理原粮,成品粮土不能使用。
3、发生中毒事故,按有机磷农药的解毒方法处理,解毒剂为阿托品。

 

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chlorpyrifos-methyl
Insecticide, acaricide
IRAC 1B; organophosphate

  Chlorpyrifos Methyl

NOMENCLATURE
Common name chlorpyrifos-methyl (BSI, E-ISO, ANSI, ESA); chlorpyriphos-methyl ((m) F-ISO, JMAF)
IUPAC name O,O-dimethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate
Chemical Abstracts name O,O-dimethyl O-(3,5,6-trichloro-2-pyridinyl) phosphorothioate
CAS RN [5598-13-0] Development codes Dowco 214 (Dow) Official codes OMS 1155; ENT 27 520

PHYSICAL CHEMISTRY
Composition 97% pure. Mol. wt. 322.5 M.f. C7H7Cl3NO3PS Form White crystals, with a slight mercaptan odour. M.p. 45.5-46.5 ºC V.p. 3 mPa (25 °C) KOW logP = 4.24 Henry 3.72 ´ 10-1 Pa m3 mol-1 (calc.) S.g./density 1.64 (23 °C) Solubility In water 2.6 mg/l (20 ºC). In acetone >400, methanol 190, hexane 120 (all in g/kg, 20 ºC). Stability Hydrolysis DT50 27 d (pH 4), 21 d (pH 7), 13 d (pH 9). Aqueous photolysis DT50 1.8 d (June), 3.8 d (December). F.p. 182 ºC (COC)

COMMERCIALISATION
History Insecticide reported by R. H. Rigterink & E. E. Kenaga (J. Agric. Food Chem., 1966, 14, 304). Introduced by Dow Chemical Co. (now Dow AgroSciences). First marketed in the US in 1985. Patents US 3244586 Manufacturers Aimco; Dow AgroSciences; Sharda

APPLICATIONS
Biochemistry Cholinesterase inhibitor. Mode of action Non-systemic insecticide and acaricide with contact, stomach, and respiratory action. Uses Control of Coleoptera, Diptera, Homoptera and Lepidoptera in cereals (including stored grains), and various foliar crop pests in pome fruit, stone fruit, citrus fruit, bush and cane fruit, vines, strawberries, vegetables, tomatoes, tea, rice, cotton, and other crops. Applied to stored grain at 6-10 cc/ton; foliar application at 250-1000 g/ha. Industrial and public health uses include control of Muscidae and crawling insects; also employed in disease vector control programs (e.g. Anopheles spp., vectors of malaria). Formulation types EC; HN; UL. Compatibility Incompatible with alkaline and strongly acidic materials. Selected products: 'Reldan' (Dow AgroSciences)

OTHER PRODUCTS
Mixtures: 'Decisprime' (+ deltamethrin) (Bayer CropScience) Discontinued products: 'Nuvagrain' * (Ciba); 'Pyriban M' * (Aimco); 'Smite' * (AgrEvo EH)

ANALYSIS
Product analysis by hplc. Residues determined by glc (Man. Pestic. Residue Anal., 1987, I, 6, S19; Anal. Methods Residues Pestic., 1988, Part I, M2, M5; Analyst (London), 1979, 104, 425; 1985, 110, 765; P. Bottomley & P. G. Baker, ibid., 1984, 109, 85). Details available from Dow AgroSciences.

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 65, 67, 92 (see part 2 of the Bibliography). Oral Acute oral LD50 for rats >3000, mice 1100-2250, guinea pigs 2250, rabbits 2000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000, rats >3700 mg/kg. Non-irritating to skin and eyes. Inhalation LC50 (4 h) for rats >0.67 mg/l. NOEL In 2 y feeding trials, NOEL, based on plasma cholinesterase levels, 0.1 mg/kg daily for dogs and rats. ADI (JMPR) 0.01 mg/kg b.w. [2001, 1992]. Toxicity class WHO (a.i.) U; EPA (formulation) III

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks >1590, bobwhite quail 923 mg/kg. Dietary LC50 (8 d) for mallard ducks 2500-5000 mg/kg. Fish LC50 (96 h) for rainbow trout 0.41, bluegill sunfish 0.88 mg/l. Daphnia LC50 (24 h) 0.016-0.025 ppm. Algae EC50 (72 h) for Selenastrum capricornutum 0.57 mg/l. Other aquatic spp. Toxic to crustaceans. LC50 (36 h) for crayfish 0.004 mg/l. Bees Very toxic to bees. LD50 (contact) 0.38 mg/bee. Worms LC50 (15 d) for Eisenia foetida 182 mg/kg soil.

ENVIRONMENTAL FATE
EHC 63 (WHO, 1986; a general review of organophosphorus insecticides). Animals In rats and other mammals, following oral administration, rapid metabolism occurs, the principal metabolite being 3,5,6-trichloropyridin-2-ol. Excretion is principally in the urine. Soil/Environment In soil, undergoes microbial degradation to 3,5,6-trichloropyridin-2-ol, which is subsequently degraded to organochlorine compounds and CO2; DT50 1.5-33 d, DT90 14-47 d, depending upon soil type and microbial activity. Kd 3.5-407 ml/g, depending on soil type. Koc is more constant: 1190-8100 ml/g.