Flufenoxuron 氟虫脲

氟虫脲

基本信息

英文名: flufenoxuron
又名: 氟芬隆
分子式：C21H11CLF6N2O3
分子量：488.1
性状：其原药（纯度98%～100%为无色固体）
纯品为无色晶体。熔点169～172℃(分解)。不溶于水，可溶于丙酮。LD50 >3000mg/kg。

药品简介

20世纪80年代出现的苯甲酰脲类昆虫生长调节剂，可由异氰酸-2,6-二氟苯甲酰酯与相应的邻氟对苯氧基苯胺反应制取。
对昆虫的作用为抑制几丁质合成，对未成熟的螨和昆虫的效果较好，用于棉花、果树、柑橘等作物上防治多种螨和害虫。
制剂有乳油。
氟虫脲分子式：C21H11CLF6N2O3熔点：169～172（分解）℃性状：其原药（纯度98%～100%为无色固体，纯品为无色晶体。溶解情况：溶解度（15℃，g/L）：水中7E-11（pH7），4μg/L(20℃)，丙酮74、82（25℃），二甲苯6，二氯甲烷24（25℃），己烷0.023（20℃）

用途

本品属苯甲酰脲类杀虫剂，是几丁质合成抑制剂，其杀虫活性、杀虫谱和作用速度均具特色，并有很好的叶面滞留性．尤其对未成熟阶段的螨和害虫有高的活性，广泛用于柑橘、棉花、葡萄、大豆、果树、王米和咖啡上，防治食植性螨类（刺瘿螨、短须螨、全爪螨、锈螨、红叶螨等）和许多其它害虫，并有很好的持效作用，对捕食性螨和昆虫安全。平均使用剂量为5～10g(a.i.)/ha或20～40g(a.i.)/ha。田间防治苹果树上的苹果全爪螨和梨潜叶蛾、柑橘树上的橘全爪螨，剂量为10～30g（a.i.）/ha。

制备或来源

以邻氟硝基苯为原料，制得2-氟－4-羟基苯胺，再与3，4-二氯三氟甲苯在氢氧化钾存在下于二甲基亚砜中反应，制得4-（4-三氟甲基－2-氯苯氧基）-2-氟苯胺。然后与以2，6-二氟苯甲腈为原料，制得的2，6-二氟苯甲酰氰酸酯反应，即得氟虫脲。

备注

稳定性≤190℃稳定；自然日光下，在水中DT50为11d；模拟日光下，玻璃板上的薄膜稳定>100h；对水解（20C）DT50206d（PH5），267d（pH7），36.7d（pH9），巳2.7d（pH12）；士埂中强烈地被吸附，在田间实际使用时，有好的水解性和光稳定性，对热稳定。原药对哺乳动物的急性毒性LD50:大鼠急性经口大于3000，大鼠和小鼠急性经皮大于2000，鹌鹑急性经口大于2000。对兔眼睛和皮肤无刺激作用。对虹鳟LC50（96h）大于100mg/L。

flufenoxuron
Insecticide, acaricide
IRAC 15; benzoylurea

NOMENCLATURE
Common name flufenoxuron (BSI, draft E-ISO, (m) draft F-ISO)
IUPAC name 1-[4-(2-chloro-a,a,a-trifluoro-p-tolyloxy)-2-fluorophenyl]-3-(2,6-difluorobenzoyl)urea
Chemical Abstracts name N-[[[4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl]amino]carbonyl]-2,6-difluorobenzamide
CAS RN [101463-69-8] Development codes WL 115 110 (Shell); SKI-8503; AC 182621; AC 811 678 (both Cyanamid); BAS 307I (BASF)

PHYSICAL CHEMISTRY
Composition ³950 g/kg pure. Mol. wt. 488.8 M.f. C21H11ClF6N2O3 Form Tech. is a white, crystalline solid. M.p. 169-172 ºC (decomp.) V.p. 6.52 ´ 10-9 mPa (20 ºC) KOW logP = 4.0 (pH 7) Henry 7.46 ´ 10-6 Pa m3 mol-1 S.g./density 0.62 Solubility In water 0.0186 (pH 4), 0.00152 (pH 7), 0.00373 (pH 9) (mg/l, 25 ºC). In acetone 82, xylene 6, dichloromethane 24, n-hexane 0.11, cyclohexane 95, dichloromethane 18.8, methanol 3.5, acetone 73.8 (all in g/l, 25 ºC). Stability Stable £190 ºC; to natural sunlight; thin film on glass stable >100 h in simulated sunlight. DT50 11 d (ambient in water). On hydrolysis (25 ºC), DT50 112 d (pH 5), 104 d (pH 7), 36.7 d (pH 9), 2.7 d (pH 12). pKa 10.1 (calc.) F.p. Not autoflammable; no explosive properties

COMMERCIALISATION
History Insecticide reported by M. Anderson et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1986, 1, 89). Evaluated by Shell Research Ltd. Product later marketed by American Cyanamid Co. (now BASF AG). Patents EP 161019 Manufacturers BASF

APPLICATIONS
Biochemistry Chitin synthesis inhibitor. Mode of action Insect and acarid growth regulator with contact and stomach action. Treated larvae die at the next moult or during the ensuing instar. Treated adults lay non-viable eggs. Uses Control of immature stages of many phytophagous mites (Aculus, Brevipalpus, Panonychus, Phyllocoptruta, Tetranychus spp.) and insect pests on pome fruit, vines, citrus fruit, tea, cotton, maize, soya beans, vegetables and ornamentals. Applied at 25-200 g/ha, depending on the crop and pests. Phytotoxicity None recorded. Formulation types EC; DC; WG. Selected products: 'Cascade' (BASF)

OTHER PRODUCTS
'Motto' (BASF); 'Pampass' (BASF) mixtures: 'Tenopa' (+ alpha-cypermethrin) (BASF, Sorex)

ANALYSIS
Product by lc. Residues by hplc. Details from BASF.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >3000 mg tech./kg. Skin and eye Acute percutaneous LD50 for rats and mice >2000 mg/kg. Non-irritating to eyes and skin (rabbits). Not a skin sensitiser (guinea pigs, M&K). Inhalation LC50 (4 h) for rats >5.1 mg/l air. NOEL (1 y) for dogs 100 mg/kg diet (3.6 mg/kg b.w. daily); (2 y) for rats 50 mg/kg diet (2.5 mg/kg b.w. daily); (2 y) for mice 1000 mg/kg diet (170 mg/kg b.w. daily) ADI 0.025 mg/kg b.w. Toxicity class WHO (a.i.) U; EPA (formulation) III

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2000 mg/kg. Fish LC50 (96 h) for rainbow trout >4.9 mg/l. Daphnia LC50 (48 h) 0.04 mg/l. Algae EC50 (96 h) for Selenastrum capricornutum >4 mg/l. Bees LD50 (oral) >109.1 mg/bee, (contact) >100 mg/bee. Worms >1000 mg/kg Other beneficial spp. Low hazard to predatory mites and other predatory and parasitic arthropods.

ENVIRONMENTAL FATE
Soil/Environment Strongly adsorbed in soil, DT50 42 d (clay loam). Use in orchards over 3 years at a dose of 97.5 g/ha gave rise to low residues in soil which did not significantly affect soil organisms, including earthworms (J. M. Gilbert et al., Proc. Br. Crop Prot. Conf. - Pests Dis., 1992, 2, 805-810).