Ethofumesate 乙呋草黄

乙呋草黄;(±)-2-乙氧基-2，3-二氢-3，3-二甲基苯并呋喃-5-基甲磺酸;ethofumesate;Nortron;Tramat;(±)-2-ethoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl-methanesulfonate;(±)-2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzfuranyl-methanesulfonate
分子式：C13H18O3S
分子量：286.3
CAS号：26225-79-6

熔点：70～72℃
蒸气压：0.065mPa(25℃)
毒性LD50(mg/kg)：急性经口LD50：大鼠大于6400，鹌鹑大于8743，日本鹌鹑大于1600，野鸭大于3445。大鼠急性经皮LD50大于1440。鱼毒LC50(96h,mg/L)：太阳鱼320、虹鳟鱼大于180。以0.015mg/只蜜蜂剂量，触杀和口服试验表明均无不良影响。
性状：纯品为无色结晶固体
溶解情况：25℃溶解度（g/L)：水中0.05，丙酮、苯、氯仿、二噁烷400，乙醇100，己烷4。
用途：芽前芽后除草剂．以1.0～2.0kg(a.i.)/ha剂量；防除甜菜、草皮、黑麦草和其它牧场中杂草。本品可有效地防除许多重要的禾本科和阔叶杂草，土壤中持效期较长．甜菜地中用量1.0～3.0kg/ha，但呋草黄与其它甜菜地用触杀型除草剂桶混的推荐剂量为0.5～2.0kg/ha草莓、向日葵和烟草基于不同的施药时期对该药有较好的耐受性。洋葱的耐药性中等。
制备或来源：对苯醌与2-甲基丙醛反应制得。
备注：pH7时水解稳定，pH1时DT50为30d，pH13为10d；每天光照12h，土壤表面DT50为8～13d。土壤中DT50：在潮湿、温暖的条件下小于35d，干燥、凉爽条件下大于98d。
类别：除草剂

ethofumesate
Herbicide
HRAC N WSSA 8; benzofuran

NOMENCLATURE
Common name ethofumesate (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name (?-2-ethoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulfonate
Chemical Abstracts name (?-2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate
CAS RN [26225-79-6] EEC no. 247-525-3 Development codes AE BO49913 (AgrEvo); NC 8438 (Fisons); SN 49913 (Schering); ZK 49913

PHYSICAL CHEMISTRY
Mol. wt. 286.3 M.f. C13H18O5S Form White, crystalline solid; (tech. is a light brown crystalline solid; mild aromatic odour). M.p. 70-72 ºC; tech., 69-71 °C V.p. 0.12 to 0.65 mPa (25 °C) KOW logP = 2.7 (pH 6.5-7.6, 25 °C) Henry 3.7 ´ 10-3 to 6.8 ´ 10-3 Pa m3 mol-1 S.g./density 1.29 (20 °C, tech.) Solubility In water 50 mg/l (25 ºC). In acetone, dichloromethane, dimethyl sulfoxide, ethyl acetate >600, toluene, p-xylene 300-600, methanol 120-150, ethanol 60-75, isopropanol 25-30, hexane 4.67 (all in g/l, 25 ºC). Stability Stable to hydrolysis in water at pH 7 and 9. At pH 5.0, DT50 940 d, forming the hydroxy analogue. Phototransformed in water, DT50 31 h. Degraded in air, DT50 4.1 h.

COMMERCIALISATION
History Herbicide reported by R. K. Pfeiffer (Symp. New Herbic., 3rd, 1969, p. 1). Introduced by Fisons Ltd, Agrochemical Division (now Bayer CropScience) in 1974. Patents GB 1271659 Manufacturers Bayer CropScience; Feinchemie Schwebda; Griffin; Punjab; Sharda; Synthesia; United Phosphorus

APPLICATIONS
Biochemistry Inhibits lipid synthesis (not ACCase inhibition). Mode of action Selective systemic herbicide, absorbed by the emerging shoots (grasses) and roots (broad-leaved plants), with translocation to the foliage. Not readily absorbed by leaves after the plant has generated a mature cuticle. Inhibits the growth of meristems, retards cellular division, and limits formation of waxy cuticle. Uses Used pre- and/or post-emergence in sugar and other beet crops, turf, ryegrass and the other pasture grasses, at 0.3-2.0 kg/ha. It is effective in controlling a wide range of important grasses and broad-leaved weeds, with a good persistence of activity in the soil. In beet crops, 1.0-2.0 kg/ha can be used, but ethofumesate is normally recommended at 0.2-2.0 kg/ha in tank-mixtures or co-formulations with other residual or contact herbicides for use in beet. A high degree of tolerance is also shown by strawberries, sunflowers, Phaseolus beans and tobacco, depending on the time of application. Phytotoxicity Onions, peas, beans, carrots, and cotton are tolerant to some extent. Formulation types EC; SC. Selected products: 'Betanal Progress' (Bayer CropScience); 'Ethosat' (Feinchemie Schwebda); 'Ethosin' (Agriphar); 'Keeper' (Barclay); 'Kubist' (Griffin); 'Nortron' (Bayer CropScience); 'Prograss' (Bayer CropScience); 'Tramat' (Bayer CropScience); mixtures: 'Betanal Tandem' (+ phenmedipham) (Bayer CropScience)

OTHER PRODUCTS
'Aran' (Barclay); 'Boxer' (Sipcam); 'Darby' (Barclay); 'Kemiron' (Bayer CropScience); 'Legclene' (Bayer CropScience); 'MSS Thor' (Nufarm UK); 'Salute' (United Phosphorus); 'Stapler' (Barclay); 'Stemat' (Stefes) mixtures: 'Beetup Pro' (+ phenmedipham+ desmedipham) (United Phosphorus Ltd); 'Beetup Trio' (+ phenmedipham+ desmedipham) (United Phosphorus Ltd); 'Betamix Progress' (+ phenmedipham+ desmedipham) (Bayer CropScience); 'Betanal Progress OF' (+ phenmedipham+ desmedipham) (Bayer CropScience); 'Betanal Quattro' (+ metamitron+ phenmedipham+ desmedipham) (Bayer CropScience); 'Betanal Trio' (+ metamitron+ phenmedipham) (Bayer CropScience); 'Betasana Trio' (+ phenmedipham+ desmedipham) (United Phosphorus Ltd); 'Betosip Combi' (+ phenmedipham) (Sipcam); 'Bettix Triple' (+ metamitron+ phenmedipham+ desmedipham) (United Phosphorus Ltd); 'Contatto' (+ phenmedipham+ desmedipham) (Feinchemie Schwebda); 'Goalpost' (+ phenmedipham) (Barclay); 'Goldpost' (+ phenmedipham) (Barclay); 'Gremlin' (+ chloridazon) (Sipcam UK); 'Kontakt Twin' (+ phenmedipham) (Feinchemie Schwebda); 'Leyclene' (+ ioxynil+ bromoxynil) (as salts) (Bayer CropScience); 'MagicTandem' (+ phenmedipham) (Stefes); 'Magnum' (+ chloridazon) (BASF); 'Powertwin' (+ phenmedipham) (Feinchemie Schwebda); 'Progress' (+ phenmedipham+ desmedipham) (Bayer CropScience); 'Saherb' (+ phenmedipham+ trifluralin+ desmedipham) (Azot); 'Spectron' (+ chloridazon) (Bayer CropScience); 'Synbetan D Forte' (+ desmedipham) (Synthesia); 'Synbetan P Forte' (+ phenmedipham) (Synthesia); 'Torero' (+ metamitron) (Feinchemie Schwebda); 'Twin' (+ phenmedipham) (Feinchemie Schwebda, Headland) Discontinued products: 'Atlas Thor' * (Atlas); 'Fumat' * (Stefes); 'MSS Ethosan' * (Mirfield); 'Primasan' * (Nufarm Whyte) mixtures: 'Medimat 2' * (+ phenmedipham) (Stefes); 'Tandem' * (+ phenmedipham) (Stefes)

ANALYSIS
Product and residue analysis by glc with FPD (R. J. Whiteoak et al., Anal. Methods Pestic. Plant Growth Regul., 1978, 10, 353). Details available from Bayer CropScience.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats and mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Not a skin or eye irritant. Not a skin sensitiser. Inhalation LC50 (4 h) for rats >3.97 mg/l air. NOEL (2 y) for rats >1000 mg/kg diet (37.6 mg/kg b.w. daily). ADI 0.4 mg/kg. Toxicity class WHO (a.i.) U; EPA (formulation) IV EC classification N; R51, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks >3552, bobwhite quail >8743 mg/kg. Dietary LC50 (8 d) for mallard ducks >1082, bobwhite quail >839 mg/kg b.w. daily. Fish LC50 (96 h) for rainbow trout 11.91-20.2, bluegill sunfish 12.37-21.2, mirror carp 10.92 mg/l. Daphnia EC50 (48 h) 13.52-22.0 mg/l. Algae EC50 3.9 mg/l. Other aquatic spp. EC50 (growth) (96 h) for Crassostrea virginica (Eastern oyster) 1.7 mg/l; LC50 (96 h) Mysidopsis bahia (mysid shrimp) 5.4 mg/l. Bees LC50 (contact and oral) >50 mg/bee. Worms LC50 134 mg/kg soil. Other beneficial spp. LD50 for Aleochara bilineata >1250, for Poecilus cupreus and Chrysoperla carnea >2000 g/ha.

ENVIRONMENTAL FATE
Animals Major metabolite is the lactone or free acid form of the respective 2-oxo compound. Plants In plants, ethofumesate is metabolised to the 2-hydroxy and 2-oxo derivatives, methanesulfonic acid, and CO2. Soil/Environment Ethofumesate is biologically degraded in soil to transient degradates which are rapidly converted to soil-bound residues and mineralised to CO2. Photodegradation also occurs. DT50 ranges from 10-122 d (lab.) and 84-407 d (field). It has been demonstrated under field conditions that ethofumesate does not accumulate in soil and that uptake by succeeding crops is negligible. It is weakly/moderately adsorbed to soil (mean Koc 203), but field lysimeter studies have demonstrated only low mobility, most residues being located in the top 30 cm. It does not leach into groundwater.