Bifenazate 联苯肼酯

联苯肼酯

简介
CAS号: 149877-41-8
CIPAC数字代号：736
英文名称：BIFENAZATE
化学名称：3-(4-甲氧基联苯基-3-基)肼基甲酸异丙酯
其他名称：NC-1111;CRAMITE; D2341;FLORAMITE;
分子式: C17H20N2O3
分子量: 300.35
结构式：

理化性质：
联苯肼酯是联苯肼类杀螨剂。其纯品外观为白色固体结晶；溶解度（20℃）：在水中为2．1mg/L；有机溶剂中（g/L）：甲苯中24．7，乙酸乙酯中102，甲醇中44.7，乙腈中95.6；分配系数（正辛醇/水）：Log Pow=3.5。

毒性：
联苯肼酯原药对大鼠急性经口、经皮LD50均>5000mg/kg， 急性吸人LC50>/L；对兔眼睛、皮肤无刺激性：豚鼠皮肤致敏试验结果为无致敏性。大鼠90d亚慢性喂养试验结果最大无作用剂量：雄性大鼠为/kg·d．雌性大鼠为/kg·d；4项致突变试验：Ames试验、微核试验、体外哺乳动物基因突变试验、体外哺乳动物染色体畸变试验均为阴性，未见致突变作用。联苯肼酯480克/升悬浮剂对大鼠急性经El LD50>5000mg/kg，急性经皮LD50>2000mg/kg，急性吸2LLC∞>2mg/L；对兔皮肤无刺激性，兔眼睛有刺激性，但无腐蚀作用：豚鼠皮肤无致敏性。
联苯肼酯480克/升悬浮剂对虹鳟鱼96h的/L，斑马鱼96h的/L；鹌鹑LD50(7d)为/kg；蜜蜂48h急性经口LD50>110μg a.i./蜂，急性接触LD50>μg a.i./；家蚕二龄LD50为/kg。该制剂用于苹果树，对鱼类高毒，高风险性；对鸟中等毒，低风险性；对蜜蜂、家蚕低毒，低风险性。使用时应注意远离河塘等水体施药，禁止在河塘内清洗施药器具。

作用特点及杀虫谱：
联苯肼酯是一种新型选择性叶面喷雾用杀螨剂。其作用机理为对螨类的中枢神经传导系统的一氨基丁酸(GABA)受体的独特作用。其对螨的各个生活阶段有效，具有杀卵活性和对成螨的击倒活性(48～72h)，且持效期长。持效期14d左右，推荐使用剂量范围内对作物安全。对寄生蜂、捕食螨、草蛉低风险。
用于苹果和葡萄防治苹果红蜘蛛、二斑叶螨和McDaniel 螨，以及观赏植物的二斑叶螨和Lewis螨。

剂型：
24%、50%联苯肼酯悬浮剂，2.5%联苯肼酯水乳剂

生产情况：
国内尚无生产报道，浙江工业大学有这方面合成研究。

其他：
美国科聚亚公司08年在我国获得登记。登记作物和防治对象为苹果树红蜘蛛。

bifenazate
Acaricide

NOMENCLATURE
Common name bifenazate (ANSI, BSI proposed)
IUPAC name isopropyl 3-(4-methoxybiphenyl-3-yl)carbazate
Chemical Abstracts name 1-methylethyl 2-(4-methoxy[1,1'-biphenyl]-3-yl)hydrazinecarboxylate
CAS RN [149877-41-8] Development codes D2341; NC-1111 (Nissan)

PHYSICAL CHEMISTRY
Composition Tech. is >95% m/m. Mol. wt. 300.4 M.f. C17H20N2O3 Form White, odourless crystals; (tech. is a beige solid). M.p. 123-125 °C (pure a.i.) V.p. <1 ´ 10-2 mPa (25 °C) KOW logP = 3.4 (25 °C, pH 7) Henry 1 ´ 10-3 Pa m3 mol-1 S.g./density 1.31 Solubility In water 2.06 mg/l (20 °C). In acetonitrile 95.6, ethyl acetate 102, methanol 44.7, toluene 24.7, hexane 0.232 g/l. Stability Stable for >1 y at 20 °C and 50% r.h. DT50 (hydrolysis) 9.10 (pH 4), 5.4 (pH 5), 0.8 (pH 7), 0.08 (pH 9) (all in d, 25 °C); DT50 (photolysis) 17 h (25 °C, pH 5). pKa 12.94 (23 °C) F.p. ³110 °C (Setaflash) Other properties Surface tension 64.9 mN/m (22 ºC).

COMMERCIALISATION
History Reported by M. A. Dekeyser et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1996, 2, 487). Discovered by Uniroyal Chemical Co., Inc. (now part of Crompton Corp.). Developed jointly by Uniroyal and Nissan Chemical and first marketed in 2000. Patents US 5367093; US 5438123 Manufacturers Crompton

APPLICATIONS
Mode of action Non-systemic acaricide with predominantly contact action and long residual action. Uses Under development by Crompton Corp. for control of phytophagous mites (both eggs and motile stages) on crops including citrus, tree fruits, vines, hops, nuts, vegetables, ornamentals, cotton and maize. Proposed use rates are 0.15-0.75 kg/ha. Formulation types SC; WG; WP. Selected products: 'Acramite' (Crompton); 'Floramite' (Crompton)

OTHER PRODUCTS
'Mito-kohne' (Nissan)

ANALYSIS
Product analysis by rp hplc with OCECD.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Very slight skin irritation, slight eye irritation (rabbits); not classified as a skin or eye irritant according to EPA or EU criteria. Not a guinea pig skin sensitiser (Buehler); is a skin sensitiser (Magnusson & Kligman). Inhalation LC50 for rats >4.4 mg/l. NOEL NOEL (90 d) for rats 40 ppm (2.7 and 3.2 mg/kg daily for males and females respy.), dogs 40 ppm (0.9 and 1.3 mg/kg daily for males and females respy.). NOEL (1 y) for dogs 40 ppm (1.014 and 1.051 mg/kg daily for males and females, respy.). NOEL (2 y) for rats 20 ppm (1.0 and 1.2 mg/kg daily for males and females, respy.). NOEL (78 week) for mice 10 ppm (1.5 and 1.9 mg/kg daily for males and females, respy.). ADI 0.01 mg/kg. Other Negative in Ames test, not mutagenic, not teratogenic in rats and rabbits. Not carcinogenic to rats and mice.

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail 1142 mg/kg. Dietary LC50 (5 d) for bobwhite quail 2298, mallard ducks 726 mg/kg diet. Fish LC50 (96 h) for bluegill sunfish 0.58, rainbow trout 0.76 mg/l. Daphnia EC50 (48 h) 0.50 mg/l. Algae ErC50 (96 h) for Selenastrum capricornutum 0.90 mg/l. Bees LD50 (48 h, oral) >100 mg/bee; (contact) 8.5 mg/bee. Worms LC50 (14 d) >1250 mg/kg. Other beneficial spp. Harmless to predacious mites such as the phytoseiids Amblyseius fallacis, Galendromus occidentalis and Zetzellia mali. 'Harmless' to Chrysoperla carnea, Orius variegatus. Encarsia formosa and Poecilus cupreus (IOBC).

ENVIRONMENTAL FATE
Animals In animals, the product is considered to be of poor bioavailability, and most of the dose is excreted in the faeces. Absorption is dose dependent (80-85% at 10 mg/kg, 22-29% at 1000 mg/kg). The absorbed dose undergoes oxidation to the corresponding azo compound, and hydroxylation; hydroxylated metabolites appear in the urine as sulfate or glucuronide conjugates. Plants Considered to be non-systemic; most residues stay on the surface and peel of the crops, where it is mostly not metabolised. Traces that penetrated the peel were metabolised as for animals. Soil/Environment DT50 in aerobic soil c. 7 h; DT50 (anaerobic) c. <1 d. Neither bifenazate nor its degradation products leached in a variety of soil types; Koc (by hplc) 1778. DT50 in natural water 45 min.; DT50 for field dissipation £5 d.