Flurtamone 呋草酮

呋草酮

CAS号：96525-23-4
英文名称：flurtamone
化学名称：（RS）-5-甲胺基-2-苯基-4-（α，α，α-三氯-间-甲苯基）呋喃-3（2H）-酮;(RS)-5-methylamino-2-phenyl-4-(α,α,α-trifluoro-m-tolyl)furan-3(2H)-one;(±)-5-(methylamino)-2-pheny-4-(3-(triflurormethyl)phenyl)-3(2H)-furanone
分子式：C18H14F3NO2
分子量：317.3

理化性质：纯品为乳白色固体粉末，熔点：152～155℃，溶解度（20℃）：水35mg/L，溶于丙酮、甲醇、二氯甲烷，微溶于异丙醇。挥发性极差。相对稳定，避免与强酸和碱接触。
毒性LD50(mg/kg)：大鼠急性经口LD50为500mg/kg，兔急性经皮LD50为500mg/kg。Ames试验表明为无诱变性。
作用特点及杀草谱：本品属呋喃－3（2H）－酮类除草剂，是类胡萝卜素合成抑制剂。对棉花、花生、高梁和向日葵有选择性。植前拌土、芽前或芽后处理，可防除许多禾本科杂草和阔叶杂草，如苘麻、美国豚草、马松子、马齿苋、大果田菁、刺黄花稔、龙葵以及苋、芸苔、山扁豆、蓼等杂草。推荐使用剂量随土壤结构和有机质含量不同而改变，在较粗结构、低有机质土壤上作植前混士处理时，施药量为0.56～0.84kg（a.i.）/ha，而在较细结构、高有机质含量的土壤上，施药量为0.84～1.12kg(a.i.)/ha或高于此量。为扩大杀草谱，最好与防除禾本科杂草的除草剂混用。本品通过植物根和芽吸收而起作用，敏感品种发芽后立即呈现普遍褪绿白化作用。
生产方法：3－（三氟甲基）苯乙腈与苯乙酸乙酯和乙醇钠在乙醇中回渣18h，再与溴在乙酸中，于室温下反应16h，得到的环合产物与硫酸二甲酯反应，即制得呋草酮。
生产情况：拜耳公司产品，国内没有企业生产。没有专利保护。

flurtamone
Herbicide
HRAC F1 WSSA 12

NOMENCLATURE
Common name flurtamone (BSI, ANSI, draft E-ISO)
IUPAC name (RS)-5-methylamino-2-phenyl-4-(a,a,a-trifluoro-m-tolyl)furan-3(2H)-one
Chemical Abstracts name (?-5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]-3(2H)-furanone
CAS RN [96525-23-4] Development codes RE-40 885 (Chevron)

PHYSICAL CHEMISTRY
Mol. wt. 333.3 M.f. C18H14F3NO2 Form Ivory powder. M.p. 152-155 ºC Solubility In water 35 mg/l (20 ºC). Soluble in acetone, dichloromethane, methanol; slightly soluble in isopropanol. Stability Stable, but avoid concentrated acids or bases.

COMMERCIALISATION
History Herbicide reported by D. D. Rogers et al. (Proc. 1987 Br. Crop Prot. Conf. - Weeds, 1, 69). Introduced by Chevron Chemical Co. and later acquired by Rhône-Poulenc Agrochimie (now Bayer CropScience). Patents US 4568376; GB 2142629 Manufacturers Bayer CropScience

APPLICATIONS
Biochemistry Blocks carotenoid biosynthesis, by inhibition of phytoene desaturase. Uses Pre-plant incorporated, pre-emergence or post-emergence control of broad-leaved and some grass weeds in small grains, peanuts, cotton, peas and sunflowers, at 250-375 g/ha. Phytotoxicity Transitory bleaching effect. Formulation types SC; WG; WP. Selected products: mixtures: 'Bacara' (+ diflufenican) (Bayer CropScience)

OTHER PRODUCTS
'Benchmark' (Bayer CropScience); 'Roulette' (Bayer CropScience) mixtures: 'Carat' (+ diflufenican) (Bayer CropScience); 'Graduate' (+ diflufenican) (Bayer CropScience); 'Ingot' (+ isoproturon+ diflufenican) (Bayer CropScience); 'Nikeyl' (+ aclonifen) (Bayer CropScience); 'Snap!' (+ diflufenican) (Me2)

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats 500 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 500, rats >5000 mg/kg. Non-irritating to skin and transient eye irritant (rabbits). NOEL c. 50 mg/kg daily. Other Not mutagenic in the Ames assay. EC classification N; R50, R53

ECOTOXICOLOGY
Birds LC50 for bobwhite quail >6000, mallard ducks 2000 mg/kg diet. Fish LC50 (96 h) for bluegill sunfish 11, rainbow trout 7 mg/l. Bees LD50 (48 h, contact) >100 mg/bee.

ENVIRONMENTAL FATE
Plants No residues in peanuts and in cereals at harvest. Soil/Environment Field DT50 46-65 d; the main metabolite is trifluoromethylbenzoic acid. Moderately adsorbed on soil colloids; flurtamone residues remained in the upper 20 cm, and the metabolite in the upper 10 cm of soil. No residues of either material could be detected 10 mo after application (R. J. Wicks et al., Proc. 9th IUPAC Int. Congr. Pestic. Chem., London, 1998, 2, 7C-023).