Asulam 磺草灵

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磺草灵

【中文名称】磺草灵;4-氨基苯磺基氨基甲酸甲酯
【英文名称】asulam;Asilan;Asulox

【相对分子量或原子量】230.2
【熔点(℃)】142~144
【蒸气压(Pa)】小于1mPa(20℃)
【毒性LD50(mg/kg)】 大白鼠、小白鼠、兔、购急性经口大于4000,大白鼠急性经皮大于1200。大白鼠90天饲喂无作用剂量为400mg/kg饲料,鱼毒LC50(96h)为:虹鳟、金鱼大于1700mg/L。
【性状】 无色结晶。
【溶解情况】 溶解性(g/L):5(20~25℃),二甲基甲酰胺大于800,丙酮340,甲醇280,甲乙酮280,乙醇120,烃和氯代烃小于20。
【用途】传导性除草剂,可被植物茎叶和根部吸收,茎叶吸收后能传导至地下根茎的生长点,并使地下根茎呼吸受抑制,丧失繁殖能力。如防除甘蔗田杂草,以2250~5250g/ha喷雾。此外,还可用于棉田、大豆、谷物、甜菜、番茄、洋葱等作物中防除狗尾草、冰草、田蓟、马唐、稗等。
【制备或来源】
(1)4-氨基苯磺酰胺与氯代甲酸甲酯反应,该反应在水或有机溶剂中进行,缚碱剂存在下,在水介质中的最适宜反应温度为10~20℃,在有机介质中于回流温度下,前者用氢氧化钠,后者在丙酮中用碳酸钾,即制得磺草灵。
(2)14kg(10.0mol)4-乙酰氨基苯磺酰胺、1.75kg(12.7mol)无水碳酸钾和16L丙酮的混合物在搅拌下,缓慢加入1.14kg(12.1mol)氯甲酸甲酯。加毕,混合物搅拌下回流18小时,然后冷却制室温,过滤,固体部分悬浮水中,用盐酸酸化,得中间物粗品,然后溶解在1mol碳酸氢钠水溶液中,过滤后的绿叶再用盐酸酸化至酸性,精制的中间物乙酰氨基苯磺酰氨基甲酸甲酯,收率45.9%,产量1.25kg,白色固体,熔点235~237℃。将572g(2.1mol)中间物溶解在2mol氢氧化钠中,室温下放置2天后,用浓盐酸酸化,生成的沉淀物用2mol/L盐酸提取,起先得到的提取盐酸加到滤液中,然后用50%情;氢氧化钠水溶液调PH值至4,得289g(1.25mol)磺草灵,收率60%,熔点145~146℃。用盐酸提取子不溶物(218g,0.8mol)加水分解的残留物为中间物,可循环使用,水解收率达96%。

 

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asulam
Herbicide
HRAC I WSSA 18; carbamate (DHP)

  Asulam

NOMENCLATURE
asulam
Common name asulam (BSI, E-ISO, ANSI, WSSA, JMAF); asulame ((m) F-ISO); no name (Germany)
IUPAC name methyl sulfanilylcarbamate
Chemical Abstracts name methyl [(4-aminophenyl)sulfonyl]carbamate
CAS RN [3337-71-1] Development codes M&B 9057 (May & Baker)

asulam-sodium
Common name asulam-sodium
CAS RN [2302-17-2]

PHYSICAL CHEMISTRY
asulam
Mol. wt. 230.2 M.f. C8H10N2O4S Form Colourless crystals. M.p. 142-144 ºC (decomp.) V.p. <1 mPa (20 ºC) Solubility In water 5 g/l (20-25 ºC). In dimethylformamide >800, acetone 340, methanol 280, methyl ethyl ketone 280, ethanol 120, hydrocarbons and chlorinated hydrocarbons <20 (all in g/l, 20-25 ºC). Other salts: in water, potassium >400, ammonium >400, calcium >200, magnesium >400 (all in g/l, 20-25 ºC). Stability Stable in boiling water ³6 h. Stable >4 y (pH 8.5, room temperature). pKa 4.82, forming water-soluble salts

asulam-sodium
Mol. wt. 252.2 M.f. C8H9N2NaO4S Solubility In water >600 g/l (20-25 ºC)

COMMERCIALISATION
History Herbicide reported by H. J. Cottrell & B. J. Heywood (Nature (London), 1965, 207, 655). Introduced by May & Baker Ltd (now Bayer CropScience). Patents GB 1040541 Manufacturers Bayer CropScience; Dow AgroSciences; High Kite; Synthesia

APPLICATIONS
Biochemistry Inhibition of dihydropteroate synthase. Mode of action Selective systemic herbicide, absorbed by the leaves, shoots, and roots, with translocation in both the symplastic and apoplastic systems to other parts of the plant. Causes a slow chlorosis in susceptible plants. Uses Control of annual and perennial grasses and broad-leaved weeds in spinach, oilseed poppies, alfalfa, some ornamentals, sugar cane, bananas, coffee, tea, cocoa, coconuts, rubber, etc.; wild oats in flax; docks (Rumex spp.) in grassland, fruit trees and bushes, and on non-crop land; and bracken (Pteridium aquilinum) in grassland, non-crop land, and forestry. Application rates from 1-10 kg/ha, depending on crop. Formulation types SL.

asulam
Selected products: 'Sanulam' (Dow AgroSciences)

OTHER PRODUCTS
asulam
'Asilan' (Shionogi, Bayer CropScience); 'Fougerox' (Bayer CropScience)

asulam-sodium
'Asulox' (Bayer CropScience)

ANALYSIS
Product analysis by rplc (CIPAC Handbook, 1998, H, 26; A. Guardigli et al., Anal. Methods Pestic. Plant Growth Regul., 1984, 13, 197) or by hydrolysis with colorimetry of a derivative (C. H. Brockelsby & D. F. Muggleton, ibid., 1973, 7, 497). Residues determined by the latter method (idem, ibid.) or by hplc of a derivative (A. Guardigli et al., loc. cit.).

MAMMALIAN TOXICOLOGY
Reviews M. A. Gallo et al., Effect of asulam in wildlife species, residues and toxicity in bobwhite quail after prolonged exposure, Bull. Environ. Contam. Toxicol., 1975, 13(2), 200-205. B. Ingham & M. A. Gallo, Effect of asulam in wildlife species - acute toxicity to birds and fish, Proc. Northeast Weed Control Conf., 1975, (1), 194-199. Oral Acute oral LD50 for rats, mice, rabbits, and dogs >4000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >1200 mg/kg. Inhalation LC50 (6 h) for rats >1.8 mg/l air. NOEL In 90 d feeding trials, rats receiving 400 mg/kg diet showed no significant ill-effects. No effect observed when fed to cows at 800 ppm over 8 w, or to sheep at 50 mg/kg over 10 d. Non-teratogenic. Toxicity class WHO (a.i.) U; EPA (formulation) IV

ECOTOXICOLOGY
asulam
Birds Acute oral LD50 for mallard ducks, pheasants, and pigeons >4000 mg/kg. Fish LC50 (96 h) for rainbow trout, channel catfish, and goldfish >5000, bluegill sunfish >3000, harlequin fish >1700 mg/l. Bees Not toxic to bees at <2% w/v by direct contact or ingestion.

asulam-sodium
Birds Acute oral LD50 for chickens, pigeons, quail >2000 mg/kg.

ENVIRONMENTAL FATE
Animals In rats, following oral administration, 85-96% of the dose is eliminated, predominantly in the urine, within 3 days. Soil/Environment Has a short persistence in soil, DT50 c. 6-14 d. Soil metabolism is by loss of amino group, cleavage of carbamate group, or acetylation of amino group.