Flurochloridone 氟咯草酮

氟咯草酮

CAS登录号：61213-25-0
化学名称：（3rs,4rs,3rs,4rs）-3-氯-4-氯甲基-1-（α，α，α-三氟间甲基）-2-吡咯烷酮（比例3：1`）
英文名称：fluorochloridone;racer;(3rs,4rs,3rs,4rs)-3-chloro-4-chloromethyl-1-α,α,α-trifluoro-m-tolyl-2-pyrrolidone(3:1);3-chloro-4-(chloromethyl)-1-(3-(trifluoromethyl)phenyl)-2-pyrrolidione
分子式：C12H10Cl2F3NO
分子量：312.1

理化性质：原药为棕色固体，熔点42～73℃，蒸气压800 pa（25℃），20℃水中溶解度28mg/l，易溶于并酮、氯苯、二甲苯，乙醇100～150g/l，煤油小于5g/l。

毒性LD50(mg/kg)：急性经口ld50：雄大鼠4000，鹌鹑大于2150。兔急性经皮ld50大于5000。对兔皮肤和眼镜有轻微刺激。ames试验和小鼠淋巴组织结果表明，本品无致突变性。鱼毒lc50(96h,mg/l)：蓝噻5，虹鳟4。蜜蜂ld50小于0.1mg/蜜蜂（接触或经口）。
作用特点及杀草谱：本品属吡咯烷酮类除草剂，是类胡萝卜素合成抑制剂。以500～750g（a.i.）/ha芽前施用．可有效防除冬小麦和冬黑麦田繁缕、常春藤叶婆婆纳和田堇菜，棉花田反枝苋、马齿苋和龙葵，马铃薯田的猪殃映．龙葵和波斯水苦菜，以及向日葵田的许多杂草。如，以750g(a.i.)/ha施于马铃薯和胡萝卜田，可防除包括难防除杂草在内的各种阔叶杂草（黄本樨草和蓝蓟），对作物安全．在轻质土中生长的胡萝卜，以500g(a.i.)/ha施用可获得相同的防效，并增加产量。

剂型：35.0%（EC）；25%EC；10%EC
生产方法：间－三氟甲基苯胺用二氯代乙酰氯酰化，然后与3-溴代丙烯反应，反应产物在氯化丁基三苯基磷的存在下，在125℃下加热反应17h，即制得氟咯草酮。

生产情况：氟咯草酮是由美国斯托弗化学公司开发的吡咯烷酮类除草剂，国内生产企业：江西安利达化工有限公司（原温州康达化工科技有限公司）；上海泰禾集团有限公司

flurochloridone
Herbicide
HRAC F1 WSSA 12

NOMENCLATURE
Common name flurochloridone (BSI, draft E-ISO, draft F-ISO); fluorochloridone (WSSA)
IUPAC name (3RS,4RS;3RS,4SR)-3-chloro-4-chloromethyl-1-(a,a,a-trifluoro-m-tolyl)-2-pyrrolidinone (in ratio 3:1)
Chemical Abstracts name 3-chloro-4-(chloromethyl)-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone
CAS RN [61213-25-0] unstated stereochemistry EEC no. 262-661-3 Development codes R-40244 (Stauffer)

PHYSICAL CHEMISTRY
Composition A mixture of cis- and trans- isomers in the ratio 1:3. Mol. wt. 312.1 M.f. C12H10Cl2F3NO Form Brown-beige, waxy solid. M.p. 40.9 °C (eutectic); 69.5 °C (trans- isomer) B.p. 212.5 °C/10 mmHg V.p. 0.44 mPa (25 °C) KOW logP = 3.36 Henry 3.9 ´ 10-3 Pa m3 mol-1 (calc.) S.g./density 1.19 (20 °C) Solubility In water 35.1 (distilled), 20.4 (pH 9) (both in mg/l, 25 °C). In ethanol 100, kerosene <5 (both in g/l, 20 ºC). Readily soluble in acetone, chlorobenzene, and xylene. Stability Stable to hydrolysis at pH 5, 7 and 9 (25 °C); in acidic media and at elevated temperatures, decomposition occurs; DT50 138 d (100 ºC), 15 d (120 ºC). DT50 (60 ºC) 7 d (pH 4), 18 d (pH 7). Aqueous photolysis DT50 4.3 d (cis-/trans-), 2.4 d (cis-), 4.4 d (trans-) (all pH 7, 25 °C).

COMMERCIALISATION
History Herbicide reported by F. Pereiro et al. (Proc. Br. Crop Prot. Conf. - Weeds, 1982, 1, 225). Introduced by Stauffer Chemical Co. (now Syngenta AG) in 1985. Rights acquired by Agan Chemical Manufacturers Ltd in 2002. Patents DE 2612731 Manufacturers Agan

APPLICATIONS
Biochemistry Inhibits synthesis of carotenoids (which prevent chlorophyll from undergoing photo-oxidation) by inhibition of phytoene desaturase. Mode of action Selective herbicide, absorbed by the roots, stems, and coleoptiles. Uses Applied at 250-750 g/ha pre-emergence to control a wide range of weeds in sunflowers, carrots and other umbelliferous crops; Stellaria media, Veronica hederifolia and Viola arvensis in winter wheat and winter rye; Galium aparine, Solanum nigrum and Veronica persica in potatoes. Formulation types CS; EC. Selected products: 'Racer' (Agan)

OTHER PRODUCTS
'Rainbow' (Agan) mixtures: 'Racer Duo' (+ acetochlor) (Agan); 'Twin Pack Gold' (+ S-metolachlor) (Agan); 'Twin Pack Premix' (+ acetochlor) (Agan)

ANALYSIS
Product analysis by gc. Residues in crops or soils determined by gc. Details of analytical methods available from Agan.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 4000, female rats 3650 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >5000 mg/kg; practically non-irritating to skin, not irritant to eyes (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >0.121 mg/l air. NOEL (2 y) for male rats 100 mg/kg diet (3.9 mg/kg b.w. daily), female rats 400 mg/kg diet (19.3 mg/kg b.w. daily). Other Genotoxicity negative. Toxicity class WHO (a.i.) U

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2000 mg/kg. Dietary LC50 (5 d) for mallard ducks and bobwhite quail >5000 mg/kg diet. Fish LC50 (96 h) for rainbow trout 3.0, bluegill sunfish 6.7 mg/l. Daphnia LC50 (48 h) 5.1 mg/l. Algae EbC50 (96 h) for Chlorella vulgaris 0.0064 mg/l. Bees Not hazardous to bees. LD50 (contact and oral) >100 mg/bee. Worms LC50 691 mg/kg. Other beneficial spp. Harmless to carabid beetles, Lycosid spider, Aphidius and Typhlodromus.

ENVIRONMENTAL FATE
Animals Flurochloridone is extensively metabolised and rapidly excreted in rats; >95% of orally applied dose was excreted in 90 h. Metabolism by oxidation, hydrolysis and glutathione conjugation yielded numerous metabolites in urine and faeces. Plants Flurochloridone is rapidly metabolised in plants. Numerous minor metabolites are formed through oxidation and conjugation. Residue levels of flurochloridone in crops are generally <0.05 mg/kg. Soil/Environment In the lab., flurochloridone is readily degraded in soil, mostly forming CO2 and a bound residue; DT50 (3 soil types, aerobic, 28 °C) 4, 5 and 27 d; two metabolites were formed, which were readily degraded further. In aerobic sediment, flurochloridone degraded with DT50 3-18 d (2 soils). In the field, DT50 9-70 d. Koc 680-1300, Kd 8-19, indicating low potential mobility on the McCall classification scale; flurochloridone does not leach because it is adsorbed and readily degraded in soil. For water, see Stability.