Primisulfuron-methyl 氟嘧磺隆

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氟嘧磺隆

CAS号:86209-51-0;113036-87-6
化学名称:2-[4,6-双(二氟甲氧基)嘧啶-2-基氨甲酰磺酰胺基]苯甲酸甲酯

英文名:Fluorisulfuron;primisulfuiron-methyl
别名: Beacon,Tell (瑞士汽巴-嘉基);
分子式: C14H10F4N4O7S

分子量:454.3

理化性质:无色结晶,熔点203℃。20℃时蒸气压<1nPa,20℃时在pH值7水中的溶解度为0.07g/L。微溶于有机溶剂。

毒  性:对人畜低毒.大鼠急性口服LD50>5050毫克/公斤,急性经皮LD50>2010毫克/公斤.对兔眼睛及皮肤无刺激作用.对鸟类、鱼类低毒.对蜜蜂无毒.。
作用特点及杀草谱:氟嘧黄隆是黄酰脲类高效内吸选择性除草剂.可被根、茎叶吸收并迅速传导到分生组织.对玉米安全,可防除禾本科杂草和阔叶杂草。适用于玉米田防除禾本科杂草和阔叶杂草.,用量为10~20g/ha。

剂型:制剂有5%可溶性颗粒剂及75%可湿性粉剂。

生产方法:以硫脲和丙二酸二乙酯为起始原料,经过环化、甲基化、双(二氟甲氧基)化、氧化、氨解和加成等六步反应,最终制得氟嘧磺隆。优化工艺条件为:环化过程物料比为n(硫脲):n(丙二酸二乙酯):n(甲醇钠)=1:1:1.3,甲醇为溶剂,回流反应5小时,制备4,6-二羟基嘧啶-2-硫酚钠的收率为94.5%;甲基化物料比为n(4,6-二羟基嘧啶-2-硫酚钠):n(硫酸二甲酯):n(氢氧化钠)=1:1.2:3,0-10℃反应4小时,制备4,6-二羟基-2-甲硫基嘧啶的收率为92.8%;双(二氟甲氧基)化时,催化剂A用量4%,n(氢氧化钠):n(4,6-二羟基-2-甲硫基嘧啶)=8:1,一氯二氟甲烷(0.5MPa),60-70℃反应4小时,制备4,6-双(二氟甲氧基)-2-甲硫基嘧啶的收率为50%;氧化和氨解利用经典工艺,收率稳定且高,分别为94.7%和93.6%;加成合成终产品时,n(邻甲氧羰基苯磺酰异氰酸酯):n[4,6-双(二氟甲氧基)-2-氨基嘧啶]=1.4:1,80℃反应3小时,制备氟嘧磺隆的收率为78%。氟嘧磺隆的总体收率提高到30.3%。
生产情况:氟嘧磺隆是目前全球范围内的重要除草剂品种,2001年全球年销售额为1.5亿美元左右。国内登记生产企业:江苏省金坛市鸿泰化工有限公司;江苏快达农化股份有限(40吨/年)
 

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primisulfuron-methyl
Herbicide
HRAC B WSSA 2; sulfonylurea

  primisulfuron-methyl

NOMENCLATURE
primisulfuron-methyl
Common name primisulfuron-methyl (BSI, draft E-ISO)
IUPAC name methyl 2-[4,6-bis(difluoromethoxy)pyrimidin-2-ylcarbamoylsulfamoyl]benzoate
Chemical Abstracts name methyl 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoate
CAS RN [86209-51-0] Development codes CGA 136872 (Ciba-Geigy)

primisulfuron
Common name primisulfuron (BSI, draft E-ISO)
CAS RN [113036-87-6]

PHYSICAL CHEMISTRY
primisulfuron-methyl
Mol. wt. 468.3 M.f. C15H12F4N4O7S Form Fine, white powder. M.p. 194.8-197.4 °C (decomp.) V.p. <5 ´ 10-3 mPa (25 ºC) (OECD 104) KOW logP = 0.2 (25 ºC, pH 7) Henry <0.04 Pa m3 mol-1 (calc.) S.g./density 1.64 (20 ºC) Solubility In water 3.7 (pH 5), 390 (pH 7), 11 000 (pH 8.5) (all in mg/l). In acetone 45 000, toluene 5790, n-octanol 130, n-hexane <1 (all in mg/l, 25 ºC). Stability Stable for at least 3 years at room temperature. Hydrolysis DT50 c. 25 d (pH 5, 25 °C), stable at pH 7 & 9. Stable up to 150 ºC. pKa 3.47

primisulfuron
Mol. wt. 454.3 M.f. C14H10F4N4O7S

COMMERCIALISATION
History Herbicidal activity of primisulfuron-methyl reported by W. Maurer et al. (Proc. 1987 Br. Crop Prot. Conf. - Weeds, 1, 41). Introduced by Ciba-Geigy AG (now Syngenta AG) and first marketed in 1990. Patents EP 84020; US 4478635 Manufacturers Syngenta

APPLICATIONS
primisulfuron-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. Selectivity derives from rapid metabolism in the crop. Metabolic basis of selectivity in sulfonylureas reviewed (M. K. Koeppe & H. M. Brown, Agro-Food-Industry, 6, 9-14 (1995)). Mode of action Selective systemic herbicide, absorbed through the roots and foliage, with rapid translocation both acropetally and basipetally. Uses Post-emergence control of problem grass weeds, e.g. Sorghum bicolor (shattercane), Sorghum almum, Sorghum halepense (johnsongrass) and Agropyron repens, and many broad-leaved weeds, in maize, at 20-40 g/ha. Phytotoxicity Maize hybrids differ in their sensitivity to primisulfuron-methyl. Formulation types WG; WP. Compatibility Compatible in tank mixtures with atrazine, bromoxynil, cyanazine, dicamba and 2,4-D. Selected products: 'Beacon' (Syngenta); 'Tell' (Syngenta); mixtures: 'Exceed' (+ prosulfuron) (USA) (Syngenta); 'Ring' (+ prosulfuron) (Syngenta)

OTHER PRODUCTS
primisulfuron-methyl
Mixtures: 'Northstar' (+ dicamba-sodium) (Syngenta); 'Spirit' (+ prosulfuron) (Syngenta) Discontinued products: 'Rifle' * (Novartis)

ANALYSIS
Residues determined by hplc. Methods for sulfonylurea residues in crops, soil and water reviewed (A. C. Barefoot et al., Proc. Br. Crop Prot. Conf. - Weeds, 1995, 2, 707).

MAMMALIAN TOXICOLOGY
primisulfuron-methyl
Oral Acute oral LD50 for rats >5050 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2010, mice >2000 mg/kg. Slightly irritating to eyes; non-irritating to skin (rabbits). No skin sensitisation (guinea pigs). Inhalation LC50 (4 h) for rats >4.8 mg/l air. NOEL (2 y) for rats 13 mg/kg b.w. daily; (19 mo) for mice 45 mg/kg b.w. daily; (1 y) for dogs 25 mg/kg b.w. daily. ADI 0.13 mg/kg b.w. Other Non-mutagenic in several tests (e.g., DNA repair and micronucleus). Toxicity class WHO (a.i.) U; EPA (formulation) IV

ECOTOXICOLOGY
primisulfuron-methyl
Birds Oral LD50 for bobwhite quail and mallard ducks >2150 mg/kg. Fish LC50 (96 h) for rainbow trout 29 mg/l. Daphnia LC50 (48 h) 260-480 mg/l. Algae EC50 (7 d) for Selenastrum 24, Anabaena 176, Navicula >227, Skeletonema >222 mg/l. Bees Non-toxic to honeybees; LC50 (48 h, contact) >100 mg/bee. Worms LD50 (14 d) >100 mg/kg soil.

ENVIRONMENTAL FATE
Animals The major metabolic pathway in the rat and other large animals involves hydroxylation of the pyrimidine ring, and partial cleavage of the sulfonylurea bridge to liberate separate phenyl and pyrimidinyl ring moieties. Plants In maize, primisulfuron-methyl is mainly degraded by ring oxidation, followed by sugar conjugation; one major metabolite is 5-hydroxyprimisulfuron-methyl. At harvest time, residues are not detectable (<0.01-0.05 mg/kg) in grain and fodder. Soil/Environment Weakly adsorbed by soil components, but field studies and lysimeter results indicate very low leaching of primisulfuron-methyl. Degradation in the soil is primarily by microbial means; DT50 (field) 4-29 d.