Bupirimate 乙嘧酚磺酸酯

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CAS RN:41983-43-6
分 子 式:C13H24N4O3S
结构式: 如右图。
熔 点:50-51℃
外 观:淡黄色或浅棕色蜡状固体
用 途:内吸性杀菌剂,主要用于防治苹果、温室玫瑰和草莓等作物的白粉病。

理化性质:20℃下蒸气压为0.5*106mmHg。室温时在水中溶解度为22mg/l,溶于大多数有机溶剂,不溶于烷烃。Kow5000(PH7)。稳定性:在稀酸中易水解,在37℃以上长期储存不稳定。土壤中半衰期35-90天(PH5.1-7.3)。工业原药 mp约40-45℃。
毒性:雌大鼠、小鼠、家兔和雄性豚鼠的口服急性LD50 约为4000mg/kg。每日以500 mg/kg的剂量经皮处理大鼠10天后未发现临床症状。对家兔眼睛有轻微刺激。以含药1000ppm浓度的饲料喂大鼠90天,未发现制病作用,对狗饲喂90天的无作用剂量为15mg/kg


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FRAC 8, A2; pyrimidinol


Common name bupirimate (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name 5-butyl-2-ethylamino-6-methylpyrimidin-4-yl dimethylsulfamate
Chemical Abstracts name 5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl dimethylsulfamate
CAS RN [41483-43-6] Development codes PP588 (ICI)

Composition Tech. is 90% pure. Mol. wt. 316.4 M.f. C13H24N4O3S Form Pale tan, waxy solid. M.p. 50-51 ºC; (tech., c. 40-45 ºC) V.p. 0.1 mPa (25 ºC) KOW logP = 3.9 Henry 1.4 ´ 10-3 Pa m3 mol-1 (calc.) S.g./density 1.2 Solubility In water 22 mg/l (pH 5.2, 25 ºC). Soluble in most common organic solvents except paraffins. Stability Stable in dilute alkalis, but readily hydrolysed by dilute acids. Rapidly decomposed by u.v. irradiation in aqueous solution. Unstable on prolonged storage above 37 ºC. F.p. >50 ºC

History Fungicide reported by J. R. Finney et al. (Proc. Br. Insectic. Fungic. Conf., 8th, 1975, 2, 667). Introduced by ICI Plant Protection Division (became Zeneca Agrochemicals) and first marketed in 1975. Sold to Makhteshim-Agan Industries in 2000. Patents GB 1400710 Manufacturers Makhteshim-Agan

Biochemistry Inhibits adenosine deaminase. Mode of action Systemic fungicide with protective and curative action. Absorbed by the leaves, with translocation in the xylem and translaminar action. Acts by inhibiting sporulation. Uses Control of powdery mildews of apples, pears, stone fruit, strawberries, gooseberries, currants, raspberries, vines, roses and other ornamentals, cucurbits, hops, beet, and other crops, at 150-375 g/ha. Phytotoxicity Chrysanthemums, roses, strawberries, and some varieties of apple may suffer slight injury. Formulation types EC; WP. Selected products: 'Nimrod' (Makhteshim-Agan)

Mixtures: 'Nimrod-T' (+ triforine) (Makhteshim-Agan); 'Oscar' (+ hexaconazole) (Makhteshim-Agan)

Product analysis by glc with FID (CIPAC Handbook, 1985, 1C, 2007) or by hplc. Identity by glc, tlc, i.r. or nmr (ibid., 1994, F, 406). Residues determined by glc of a derivative. Details available from Syngenta.

Oral Acute oral LD50 for rats, mice, rabbits, and guinea pigs >4000 mg/kg. Skin and eye Acute percutaneous LD50 for rats 4800 mg/kg. Not irritating to eyes and skin. Moderate skin sensitiser (guinea pigs). Inhalation No effect on rats exposed for 4 h to 0.035 mg respirable particles/l air. NOEL (2 y) for rats 100 mg/kg diet; (90 d) for rats 1000 mg/kg diet, for dogs 15 mg/kg daily. Toxicity class WHO (a.i.) U; EPA (formulation) III EC classification (Xi; R43| N; R51, R53)

Birds Acute oral LD50 for quail >5200, pigeons >2700 mg/kg. Oral LC50 (5 d) for bobwhite quail and mallard ducks >10 000 mg/kg. Fish LC50 (96 h) for rainbow trout 1.4 mg/l. Daphnia LC50 (48 h) 7.3 mg/l. Bees NOEL: 0.20 mg/bee (oral); 0.050 mg/bee (contact).

Animals In mammals, following oral administration, 68% of the dose is eliminated in the urine within 24 hours; 77% is eliminated in the urine and 21% in the faeces within 10 days. Soil/Environment In soil, the major degradation product is ethirimol. Soil DT50 35-90 d (non-sterile flooded or non-flooded soils, pH 5.1-7.3).