Sulfometuron-Methyl 甲嘧磺隆

甲嘧磺隆

英文名称：Sulfometuron-Methyl
CAS NO：74222-97-2
化学名称：2-(4,6-二甲基嘧啶-2-基氨基甲酰氨基磺酰基)苯甲酸甲酯
其他名称：傲杀;奥斯达;甲基嗪磺隆;DPX-T5648，嘧磺隆、森草净、草灌净、林无草、OUST
分子式: C15H16N4O5S
分子量: 364.38

理化性质：原药为白色固体。m.p.203～205℃，蒸气压7.39×10-14Pa，相对密度1.48。25℃时，溶解度为：丙酮2.4g/kg，乙腈1.5g/kg，乙醇137mg/kg，乙醚32mg/kg，二甲苯37mg/kg，水8mg/L (pH=5)、70mg/L (pH=7)。分配系数0.31 (pH=7)。水悬浮液在pH=5时水解半衰期18d,pH=7～9稳定。土壤中半衰期约28d。

毒性：低毒，急性经口LD50为大于5000mg/kg，急性经皮LD50为大于2000mg/kg（兔）

作用特点及杀草谱：磺酰脲类除草剂，抑制支链氨基酸合成，从而抑制植株生长端的细胞分裂，阻止杂草生长至失绿坏死。本品为芽前、芽后灭生性除草剂，适用于林木防除一年生和多年生禾本科杂草及阔叶杂草，或开辟森林隔离带，伐木后林地清理，荒地垦前、休闲非耕地、道路边荒地除草灭灌，如羊茅、一枝黄花、黍、油莎草、阿拉伯高梁、豚草等。用量为210～250g/h m2，可常规喷洒，也可用飞机喷洒。不宜用于农田除草。用于防治非耕地的一年生和多年生禾本科杂草

剂型：10%可溶性粉剂、10％县浮剂、75％可湿性粉剂、75％水分散粒剂。

生产方法：2-氨基-4，6-二甲基嘧啶的制备 先由双氰胺和硝酸铵（或碳酸盐）作用制得硝酸胍盐（或碳酸胍盐），然后将12.2g硝酸胍盐、10g乙酰丙酮、100mL水及8g碳酸钾在室温下反应。经过滤、干燥等后处理得7.4g 2-氨基-4，6-二甲基嘧啶，收率60%。
邻甲酸甲酯苯磺酰基异氰酸酯的制备 参见甲磺隆的制备方法。
嘧磺隆的合成 将2-氨基-4，6-二甲基嘧啶（4g)与邻甲酸甲酯苯磺酰基异氰酸酯 （7.8g)在乙腈 （60mL)溶剂中，于室温下搅拌反应16h，过滤得白色晶体，收率91%。

生产情况：江苏瑞东农药有限公司，西安近代化学研究所，金华市金龙化工有限公司，连云港市新田化工有限公司，江苏快达农化股份有限公司

sulfometuron-methyl
Herbicide
HRAC B WSSA 2; sulfonylurea

NOMENCLATURE
sulfometuron-methyl
Common name sulfometuron-methyl
IUPAC name methyl 2-(4,6-dimethylpyrimidin-2-ylcarbamoylsulfamoyl)benzoic acid; 2-[3-(4,6-dimethylpyrimidin-2-yl)ureidosulfonyl]benzoate
Chemical Abstracts name methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoate
CAS RN [74222-97-2] Development codes DPX T5648 (DuPont)

sulfometuron
Common name sulfometuron (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name 2-(4,6-dimethylpyrimidin-2-ylcarbamoylsulfamoyl)benzoic acid; 2-[3-(4,6-dimethylpyrimidin-2-yl)ureidosulfonyl]benzoic acid
Chemical Abstracts name 2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoic acid
CAS RN [74223-56-6] Development codes DPX T5648 (DuPont)

PHYSICAL CHEMISTRY
sulfometuron-methyl
Composition Tech. is >93%. Mol. wt. 364.4 M.f. C15H16N4O5S Form Colourless solid (tech.). M.p. 203-205 ºC V.p. 7.3 ´ 10-11 mPa (25 ºC) KOW logP = 1.18 (pH 5), -0.51 (pH 7) Henry 1.2 ´ 10-13 Pa m3 mol-1 (25 °C) S.g./density 1.48 Solubility In water 244 mg/l (pH 7, 25 ºC). In acetone 3300, acetonitrile 1800, ethyl acetate 650, diethyl ether 60, hexane <1, methanol 550, dichloromethane 15 000, dimethyl sulfoxide 32 000, octanol 140, toluene 240 (all in mg/kg, 25 ºC). Stability Aqueous suspensions are stable to hydrolysis at pH 7 to pH 9, DT50 c. 18 d (pH 5). pKa 5.2

sulfometuron
Mol. wt. 350.3 M.f. C14H14N4O5S

COMMERCIALISATION
History Introduced as a herbicide by E. I. du Pont de Nemours and Co.; commercially available in 1982. Manufacturers DuPont

APPLICATIONS
sulfometuron-methyl
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Acts by inhibiting biosynthesis of the essential amino acids valine and isoleucine, hence stopping cell division and plant growth. Mode of action Broad-spectrum herbicide, absorbed rapidly by the leaves and roots, with translocation throughout the plant. Uses Control of annual and perennial grasses (especially Sorghum halepense) and broad-leaved weeds in non-crop land. Also used for selective weed control in Bermuda grass and certain other turf grasses; and in forestry to control woody tree species in pine trees. Applied either pre- or post- emergence; range of use rates is 26-420 g/ha. Phytotoxicity Not to be applied near desirable trees and plants. Formulation types WG. Compatibility Incompatible with alkaline materials. Selected products: 'Oust' (DuPont)

OTHER PRODUCTS
sulfometuron-methyl
Mixtures: 'Oustar' (+ hexazinone) (DuPont) Discontinued products mixtures: 'Stampro' * (+ propanil) (Dow AgroSciences)

ANALYSIS
Product and residue analysis by hplc (E. W. Zahnow & T. J. Waeghe, Anal. Methods Pestic. Plant Growth Regul., 1988, 16, 105). Details available from DuPont.

MAMMALIAN TOXICOLOGY
sulfometuron-methyl
Oral Acute oral LD50 for male rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg; slight skin and eye irritant (rabbits). No skin sensitisation (guinea pigs). Inhalation LC50 (4 h) for rats >11 mg/l air. NOEL (2 y) for rats 50 mg/kg diet. In 2-generation reproduction studies, NOEL for rats 500 mg/kg diet. Teratogenicity effects in rats at 1000 mg/kg diet, and in rabbits at 300 mg/kg diet. Toxicity class WHO (a.i.) U; EPA (formulation) IV

ECOTOXICOLOGY
sulfometuron-methyl
Birds Acute oral LD50 for mallard ducks >5000, bobwhite quail >5620 mg/kg. Fish LC50 (96 h) for rainbow trout and bluegill sunfish >12.5 mg/l. Daphnia LC50 >12.5 ppm. Bees Contact LD50 >100 mg/bee.

ENVIRONMENTAL FATE
Animals Metabolised to hydroxylated sulfometuron-methyl. Soil/Environment Degraded by microbial action and by hydrolysis. DT50 in soil c. 4 w. Koc 85.