Triflusulfuron-methyl 氟胺磺隆

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氟胺磺隆

【中文名称】氟胺磺隆;3-(4-二甲基氨基-6-(2,2,2-三氟乙氧基)-1,3,5-三嗪-2-氨基甲酰氨基磺酰基)间甲基苯甲酸甲酯
【英文名称】triflulsulfuron-methyl;methyl 2-((4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)carbamkoylaulfamoyl)-m-methylbenzaote;methyl-2-(((4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)carbonoylaminosulfonyl)-3-methylbensoate
【商品名】Debut;Safari;Upbeet;
【CAS登录号】
126535-15-7
【结构或分子式】
【相对分子量或原子量】492.4
【熔点(℃)】160~163
【毒性LD50(mg/kg)】
大鼠急性经口大于5000,兔急性经皮大于2000。原药对兔眼睛无刺激作用,对豚鼠皮肤无过敏性。Ames试验为阴性。
【溶解情况】
水溶解度分别为(25℃,mg/L):1(pH3)、3(pH5)、110(pH7)、11000(pH9)
【用途】
本品属磺酰脲类除草剂。抑制植物的乙酰乳酸酶(ALS)合成,阻断侧链氨基酸生物合成,从而影响细胞的分裂和生长.本品的防除甜菜田许多阔叶杂草和禾本科杂草,而且是安全性高的芽后除草剂,按两倍的推荐用量施用,对甜菜仍极安全,在l~2叶以上的甜菜中的DT50<6h。添加非离子表面活性剂或植物油有助于改善其互溶性,并提高活性。推荐用量为10~25g(a.i.)/ha,并加入0.05%~0.25%(体积)的表面活性剂或0.5~1.0(体积)的植物油.
【其他】
稳定性:在25℃水中DT50为3.7d(pH5),32d(pH7)、36d(pH9)

 

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triflusulfuron-methyl
Herbicide
HRAC B WSSA 2; sulfonylurea

  triflusulfuron-methyl

NOMENCLATURE
triflusulfuron-methyl
Common name triflusulfuron-methyl
IUPAC name methyl 2-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylcarbamoylsulfamoyl]-m-toluate
Chemical Abstracts name methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate
Other names JT478 CAS RN [126535-15-7] Development codes DPX-66037 (DuPont); IN 66037

triflusulfuron
Common name triflusulfuron (BSI, pa E-ISO, ANSI)
IUPAC name 2-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylcarbamoylsulfamoyl]-m-toluic acid
Chemical Abstracts name 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoic acid
CAS RN [135990-29-3]

PHYSICAL CHEMISTRY
triflusulfuron-methyl
Composition Tech. is >96%. Mol. wt. 492.4 M.f. C17H19F3N6O6S Form White, crystalline solid. M.p. 160-163 ºC; (tech., 155-158 °C) V.p. 6 ´ 10-7 mPa (Knudsen gas effusion, 25 ºC) KOW logP = 0.96 (pH 7) Henry <5.9 ´ 10-5 Pa m3 mol-1 (pH 7) S.g./density 1.45 Solubility In water 1 (pH 3), 3.8 (pH 5), 260 (pH 7), 11 000 (pH 9) (all in mg/l, 25 ºC). In dichloromethane 580, acetone 120, methanol 7, toluene 2, acetonitrile 80 (all in mg/ml, 25 °C). Stability Rapidly hydrolysed in water, DT50 3.7 d (pH 5), 32 d (pH 7), 36 d (pH 9) (all 25 ºC). pKa 4.4

triflusulfuron
Mol. wt. 478.4 M.f. C16H17F3N6O6S

COMMERCIALISATION
History Reported by L. A. Peeples et al. (Proc. Br. Crop Prot. Conf. - Weeds, 1991, 1, 25). Introduced by E. I. du Pont de Nemours and Co. Manufacturers DuPont

APPLICATIONS
triflusulfuron-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 is due to rapid metabolism in sugar beet (M. K. Koeppe et al., Proc. Br. Crop Prot. Conf. - Weeds, 1993, 1, 177). Metabolic basis of selectivity in sulfonylureas reviewed (M. K. Koeppe & H. M. Brown, Agro-Food-Industry, 6, 9-14 (1995)). Mode of action Post-emergence selective herbicide. Symptoms occur first in meristematic tissue. Uses Post-emergence control of many annual and perennial broad-leaved weeds in sugar beet, at 10-30 g/ha. Formulation types WG. Compatibility Compatible with other sugar beet herbicides. Selected products: 'Debut' (W. Europe) (DuPont); 'Safari' (E. Europe & Scandinavia) (DuPont); 'Upbeet' (USA) (DuPont)

OTHER PRODUCTS
triflusulfuron-methyl
'TFS 50' (Landgold)

ANALYSIS
By lc/u.v. and lc/ms/ms detection. Methods for sulfonylurea residues in crops, soil and water reviewed (C.R. Powley, Handbook of Residue Analytical Methods, pp 400-410).

MAMMALIAN TOXICOLOGY
triflusulfuron-methyl
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Non-irritating to skin and eyes (rabbits). Non-sensitising to skin (guinea pigs). Inhalation LC50 (4 h) for rats >5.1 mg/l. NOEL (1 y) for dogs 875 ppm; (18 mo) for mice 150 ppm; (2 y) for male rats 100, female rats 750 ppm. ADI (UK) 0.05 mg/kg. Other Non-mutagenic in the Ames test. Toxicity class WHO (a.i.) U

ECOTOXICOLOGY
triflusulfuron-methyl
Birds LD50 for mallard ducks and bobwhite quail 2250 mg/kg. Dietary LC50 for mallard ducks and bobwhite quail >5620 ppm. Fish LC50 (96 h) for bluegill sunfish 760, trout 730 mg/l. Daphnia LC50 (48 h) >960 mg/l. Algae EC50 (120 h) for green algae 0.62 mg/l. Other aquatic spp. LC50 (14 d) for Lemna gibba 9.0 mg/l. Bees Oral LD50 (48 h) >1000 ppm. Worms LD50 for earthworms >1000 mg/kg.

ENVIRONMENTAL FATE
The compound rapidly degrades in water, soil, plants, and animals. The primary metabolic pathways in all the systems are the cleavage of the sulfonylurea bridge, yielding methyl saccharin and triazine amine, followed by N-demethylation to N-desmethyl triazine amine, and N,N-bis-desmethyl triazine amine. The metabolic pathway is consistent in aquatic, soil, and biological systems. Soil/Environment Degrades rapidly in soil by chemical and microbial mechanisms. Microbial degradation is important in alkaline conditions, but plays only a minor role in neutral and acidic conditions because chemical hydrolysis is very rapid. Half-life in soil 3 d. Bioaccumulation is unlikely to occur.