Carfentrazone-ethyl 唑草酯，唑草酮，唑酮草酯，三唑酮草酯 氟唑草酮

用于麦类、水稻、玉米防除阔叶杂草和莎草。2008年8月30日到期。FMC公司开发。2009年市场为0.95亿美元。1997年上市。

唑酮草酯

中文别名： (RS)-2-氯-3(2-氯-5-(4-二氟甲基-4,5-二氢-3-甲基-5-氧-1H-1,2,4-三唑-1-基)-4-氟苯基)丙酸乙酯;福农;唑草酯
英文名称： carfentrazone
英文别名：
Affinty;ethyl (RS)-2-chloro-3-(2-chloro-5-(4-difluirimethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorophenyl)propionate;ethyl-2-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorobenzenepropanate;carfentrazone (free acid);CARFENTRAZONE;ethyl-(RS)-2-chloro-3-[2-chloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol)-4-fluorophenyl] propionate;F 116426;F 8426;2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoic acid;
分子式： C13H10Cl2F3N3O3
分子量： 384.138
InChI： InChI=1/C13H10Cl2F3N3O3/c1-5-19-21(13(24)20(5)12(17)18)10-3-6(2-8(15)11(22)23)7(14)4-9(10)16/h3-4,8,12H,2H2,1H3,(H,22,23)
密度： 1.67g/cm3
沸点： 472.8°C at 760 mmHg
闪点： 239.7°C

唑酮草酯由美国FMC公司开发 ,属内吸性除草剂 ,主要用于防除小麦、大麦、燕麦、水稻、玉米、大豆、柑桔、咖啡、棉花、高粱、葡萄园、草坪等中的阔叶杂草和莎草。
【中文名】三唑酮草酯；福农；快灭灵；（RS）-2-氯-3（2-氯-5-（4-二氟甲基-4，5-二氢-3-甲基-5-氧-1H-1，2，4-三唑-1-基）-4-氟苯基）丙酸乙酯 【英文名】carfentrazone-ethyl;Affinty;ethyl (RS)-2-chloro-3-(2-chloro-5-(4-difluirimethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorophenyl)propionate;ethyl-2-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorobenzenepropanate 【CAS号】128621-72-7
【分子式】c15h14cl2f3n3o3
【分子量】
【密度】1.457(20℃)
【熔点】-22.1℃
【沸点】350～335℃/mmHg
【闪点】 【粘度】
【蒸气压】1.6E-5(25℃)
【折射率】 【毒性LD50】急性经口LD50：大鼠5143，野鸭大于1000。兔急性经皮LD50大于4000。对兔眼睛有轻微刺激，对兔皮肤无刺激。Ames试验呈阴性。小鼠淋巴瘤和活体小鼠微核试验呈阴性。WHO原药毒性分级为Ⅱ类。
【性状】纯品为黏稠黄色液体
【溶解情况】水中溶解度（μg/L）：12（20℃）、22（25℃）
【用途】三唑啉酮类除草剂。对禾谷类作物，如小麦、大麦、水稻、玉米等具有选择性的苗后除草剂．可用于防除阔叶杂草如猪殃殃、野芝麻、婆婆纳、苘麻、红心藜、空管牵牛、藜、反枝苋、小果亚麻、地肤、龙葵、白芥等杂草．对猪殃殃、苘麻、红心藜、空管牵牛等杂草具有优异的防效；对磺苋脲类除草剂产生抗性的杂草如 Kochia scoperiade等具有很好的活性．因其在土壤中的半衰期仅为几小时，故对下茬作物亦安全．其可方便的进行茎叶处理，使用剂量为20～35kg(a.i.)/ha。
【制备或来源】以邻氟苯胺为起始原料，经酰化、氯化、水解制得中间体4-氯-2－氟苯胺；经重氮化还原制得中间体取代苯肼，再与丙酮酸缩合、与二苯基磷酰叠氮化物反应制得中间体取代的三唑啉酮，熔点189～191；三唑啉酮与氯氟甲烷反应后再硝化、还原再经重氮化与丙烯酸乙酯应应，处理即得目的物。
【备注】原卟啉原氧化酶的抑制剂。即通过抑制叶绿素生物合成过程中原卟啉原氧化酶而引起细胞膜破坏，使叶片迅速干枯、死亡。

carfentrazone-ethyl
Herbicide
HRAC E WSSA 14; triazolinone

NOMENCLATURE
Common name carfentrazone-ethyl (BSI, pa ISO, ANSI)
IUPAC name ethyl (RS)-2-chloro-3-[2-chloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorophenyl]propionate
Chemical Abstracts name ethyl a,2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-4-fluorobenzenepropanoate
CAS RN [128621-72-7] (for the acid); [128639-02-1] (for the ethyl ester) Development codes F8426; F116426 (both FMC)

PHYSICAL CHEMISTRY
Mol. wt. 412.2 M.f. C15H14Cl2F3N3O3; C13H10Cl2F3N3O3 for acid Form Viscous yellow liquid. M.p. -22.1 ºC B.p. 350-355 ºC/760 mmHg V.p. 1.6 ´ 10-2 mPa (25 ºC) KOW logP = 3.36 Henry 2.47 ´ 10-4 Pa m3 mol-1 (20 °C, calc.) S.g./density 1.457 (20 ºC) Solubility In water 12 mg/ml (20 ºC), 22 mg/ml (25 ºC), 23 mg/ml (30 ºC). In toluene 0.9, hexane 0.03 (both in g/ml, 20 °C); miscible with acetone, ethanol, ethyl acetate and dichloromethane. Stability Hydrolytic DT50 3.6 h (pH 9), 8.6 d (pH 7), stable (pH 5). Aqueous photolytic DT50 8 d. F.p. >110 ºC

COMMERCIALISATION
History Reported by W. A. van Saun et al. (Proc. Br. Crop Prot. Conf. - Weeds,1993, 1, 19). Introduced in 1997. Manufacturers FMC

APPLICATIONS
Biochemistry Acts by inhibition of protoporphyrinogen oxidase, leading to membrane disruption. Mode of action Absorbed by foliage, with limited translocation. Uses Post-emergence control in cereals of a wide range of broad-leaved weeds, especially Galium aparine, Abutilon theophrasti, Ipomoea hederacea var. hederacea, Chenopodium album and several mustard species, at 9-35 g/ha. Also for desiccation of potatoes, at 60 g/ha. Phytotoxicity Good tolerance in wheat, barley and rice. Formulation types EC; SG; WG. Selected products: 'Aurora' (FMC); 'Spotlight' (FMC); mixtures: 'Affinity' (+ isoproturon) (FMC); 'Platform S' (+ mecoprop-P) (FMC)

OTHER PRODUCTS
'Aim' (FMC); 'Platform' (FMC); 'Shark' (FMC) mixtures: 'Alli?Express' (+ metsulfuron-methyl) (DuPont); 'Ally Express' (+ metsulfuron-methyl) (DuPont); 'Aurora Turbo' (+ mecoprop-P) (Philagro); 'Harmony Express' (+ thifensulfuron-methyl) (DuPont); 'Lexus Class' (+ flupyrsulfuron-methyl-sodium) (DuPont) Discontinued products mixtures: 'Affinity' * (+ isoproturon) (DuPont); 'Platform S' * (+ mecoprop-P) (DuPont)

ANALYSIS
Details from FMC.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for female rats 5143 mg/kg. Skin and eye Acute percutaneous LD50 for rats >4000 mg/kg. Minimally irritating to eyes and non-irritating to skin (rabbits). No skin sensitisation (guinea pigs). Inhalation LC50 (4 h) for rats >5 mg/l. NOEL (2 y) for rats 3 mg/kg daily. ADI 0.03 mg/kg (proposed). Other Non-mutagenic in the Ames test. Toxicity class WHO (a.i.) III (company classification); EPA (formulation) III, IV EC classification N; R50, R53

ECOTOXICOLOGY
Birds LD50 for quail >1000 mg/kg. LC50 for quail and ducks >5000 ppm. Fish LC50 (96 h) 1.6-43 mg/l, depending on species. Daphnia EC50 (48 h) 9.8 mg/l. Algae EC50 12-18 mg/l, depending on species. Other aquatic spp. EC50 (96 h) for eastern oyster 2.05, mysid shrimp 1.16 ppm. Bees LD50 (oral) >35; (contact) >200 mg/bee. Worms LC50 >820 mg/kg soil.

ENVIRONMENTAL FATE
Animals In rats, c. 80% of the administered dose is rapidly absorbed and excreted in the urine within 24 h. The major metabolite was the corresponding acid. Further metabolism appears to involve oxidative hydroxylation of the methyl group or dehydrochlorination to form the corresponding cinnamic acid. Plants Rapidly converted to the free acid, which is hydroxylated and then oxidised at the triazolinone methyl to form the dibasic acid; DT50 (carfentrazone-ethyl) <7 d, DT50 (carfentrazone) <28 d. Soil/Environment Broken down in the soil by microbial action; not susceptible to photodecomposition nor volatility following soil application. Strongly adsorbed to sterile soils (Koc 750?0 at 25 ºC). In non-sterile soils, rapidly converted to the free acid, which has low soil binding (Koc 15-35 at 25 ºC, pH 5.5). In the laboratory, soil DT50 is a few hours, degrading to the free acid, which in turn has DT50 2.5-4.0 d.