Acrinathrin 杀螨菊酯

杀螨菊酯

CAS号: 101007-06-1
英文名称：acrinathrin
化学名称：（S)α-氰基-3-苯氧基苄基（Z）-（1R,3R)-3-（2,2,2-三氟-1-三氟甲基乙氧基甲酰）乙烯基2,2-二甲基环丙烷羧酸酯
其他名称：罗速发、罗速、罗素发、氟脂菊酯、氟丙菊酯
分子式: C26H21F6NO5
分子量: 541.44

理化性质：原药有效成分含量≥95%，外观为白色粉末，熔点约81.5℃，蒸气压39×10-7帕（25℃），水分含量＜0.1%（m/m)，在水中溶解度＜0.02μg/ml(25℃),乙酸乙酯中＞50%（m/v),丙酮、氯仿、二氯甲烷＞50%（m/v)，乙醇4%，乙烷1%，甲醇5%，正辛醇1%，甲苯50%（m/v)。辛醇/水中分配比为1.8×105（25℃），密度0.5（20℃），pH7。55℃时，在空气中贮存1个月无变化，光稳定性（半衰期50小时，常温贮存稳定性大于2年。在酸性条件下稳定，中性或碱性中易分解，且随pH值和温度升高而增强。在水中半衰期小于7天。
毒性：按我国农药毒性分级标准，氟丙菊酯属低毒杀螨、杀虫剂。原药大鼠急性经口LD50＞5000毫克/公斤，经皮LD50＞2000毫克/公斤，吸入LC501600毫克/米3。对兔眼睛有轻微刺激，无皮肤刺激和致敏作用。大鼠亚慢性（90天）无作用剂量为30毫克/公斤（饲料）或2.4毫克/公斤。大、小鼠两年慢性无作用剂量约2毫克/公斤（饲料）。致突变试验为阴性。对大鼠两代繁殖和兔、大鼠致畸无不良影响。对大、小鼠无致癌作用。母鸡试验无迟发性神经毒性。推荐的ADI为0.02毫克/公斤/天。两倍用量对蚯蚓无危害，试验室条件下对鱼剧毒。鹌鹑LD502250毫克/公斤（饲料）。蜜蜂经口LD500.102-0.147微克/只，接触LD501.208-1.898微克/只。

氟丙菊酯对人、畜低毒，在水中半衰期小于7天，在沙质土壤中半衰期约为52天；在植物上如苹果和甘蓝上，无代谢产物蓄积，残留量小于0.2毫克／千克。2％乳油对皮肤有轻微刺激，对眼睛有强刺激性，但稀释后的喷洒液无刺激性。每日允许摄入量：0.02 mg/kg；但对鱼类毒性高，LC50 （mg/L）分别为：虹鳟鱼5.66，鲤鱼0.12，绿藻>0.82，蚯蚓>1 000mg/kg；对蜜蜂：经口LC50 （48小时）150~200ng/蜂，接触（48小时）200~500 ng/蜂；对天敌：急性经口LD50 （mg/kg）：北美鹑>2 250，野鸭>1 000。

作用特点及杀虫谱：：氟丙菊酯属拟除虫菊酯类杀螨、杀虫剂，主要作用于昆虫神经上的钠离子通道（Na+），干扰电压依赖的Na+通道闸门开闭的动力学，使得Na+通道延迟关闭，引起重复后放和突触传递的阻断，使昆虫中毒死亡。作用方式主要为胃毒和触杀，无内吸和渗透作用。对成、若螨高效，击倒速度快，持效期达20天以上，并对多种蚜虫、蓟马、潜叶蛾、卷叶蛾、小绿叶蚕、木虱等有良好的防治效果。
本品属拟除虫菊酯类杀螨、杀虫剂，对多种植食性害螨有良好的触杀和胃毒作用。对桔全爪螨、短须螨、二叶螨、苹果红蜘蛛的幼、若螨及成螨均有良好防效。同时对刺吸式口器的害虫及鳞翅目害虫也有杀虫活性。
使用方法：
(1)茶树害虫 防治茶短须螨、咖啡小爪螨，用2％乳油2 000～4 000倍液喷雾，持效期14～20天。防治茶小绿叶蝉，用2％乳油1 330～2 000倍液喷雾，持效期7天左右。
(2)果树害虫 防治苹果红蜘蛛、山楂红蜘蛛，用2％乳油1 000～2 000倍液喷雾，持效期约30天。当叶螨和食心虫混合发生时，可用2％乳油1 000～1 500倍液喷雾，持效期10～14天，并可兼治绣线菊蚜。防治橘全爪螨，用2％乳油800～1 500倍液喷雾，持效期20天左右，并兼治潜叶蛾、橘蚜。
(3)棉花害虫 防治棉花二点叶螨，用2％乳油1 500～2 000倍液喷雾，持效期10天左右，并兼治棉蚜。
(4)茄子、豇豆等蔬菜红蜘蛛 在螨发生初期，平均每叶有螨2～3头时，喷2％乳油1 0。
(5)大豆和花生叶螨类 用2％乳油1 000～2 000倍液喷雾，亩喷药液30～40千克，尤其要注意喷洒叶背面。可兼治蚜虫、潜叶蝇及卷叶螟等害虫。

剂型：2％乳油，3％可湿性粉剂。与炔螨特复配41．5％乳油(重量／容重)。
生产方法：由(1R，Cis)二溴菊酸乙酯为起始原料，经交换、加成、氧化和缩合反应得杀螨菊酯成品，含量为96．2％，总收率为56％。

acrinathrin
Acaricide, insecticide
IRAC 3; pyrethroid

NOMENCLATURE
Common name acrinathrin (BSI, draft E-ISO); acrinathrine (draft F-ISO)
IUPAC name (S)-a-cyano-3-phenoxybenzyl (Z)-(1R,3S)-2,2-dimethyl-3-[2-(2,2,2-trifluoro-1-trifluoromethylethoxycarbonyl)vinyl]cyclopropanecarboxylate
Roth: (S)-a-cyano-3-phenoxybenzyl (Z)-(1R-cis)-2,2-dimethyl-3-[2-(2,2,2-trifluoro-1-trifluoromethylethoxycarbonyl)vinyl]cyclopropanecarboxylate
Chemical Abstracts name cyano(3-phenoxyphenyl)methyl 2,2-dimethyl-3-[3-oxo-3-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]-1-propenyl]cyclopropanecarboxylate
CAS RN [101007-06-1] as defined; [103833-18-7] unstated stereochemistry Development codes RU 38 702 (Roussel Uclaf); HOE 076003 (Hoechst); AE F 076003 (AgrEvo); NU 702

PHYSICAL CHEMISTRY
Composition Material is a single isomer. Mol. wt. 541.4 M.f. C26H21F6NO5 Form White powder (tech.). M.p. 81.5 ºC (pure); 82 ºC (tech.) V.p. 4.4 ´ 10-5 mPa (20 °C) KOW logP = 5.6 (a.i., 25 ºC) Henry 4.8 ´ 10-2 Pa m3 mol-1 (calc.) Solubility In water £0.02 mg a.i./l (25 ºC). In acetone, chloroform, dichloromethane, ethyl acetate, dimethylformamide >500, di-isopropyl ether 170, ethanol 40, hexane 10, n-octanol 10 (all in g a.i./l). Stability Stable in acid, but hydrolysis and epimerisation more important at pH >7. DT50 >1 y (pH 5, 50 ºC), 30 d (pH 7, 30 ºC) 15 d (pH 9, 20 ºC), 1.6 d (pH 9, 37 ºC). Stable for 7 d under 100 W light (tech.). Specific rotation [a]D20 +17.5?

COMMERCIALISATION
History Acaricide and insecticide reported by J. R. Tessier et al. (IUPAC Pestic. Chem., 1983, 5, 95). Introduced in France (1990) by Roussel Uclaf (now Bayer CropScience). Licensed to Cheminova in 2003. Patents EP 48186; FR 2486073 Manufacturers Bayer CropScience

APPLICATIONS
Biochemistry Acts on the nervous system of insects, disturbs the function of neurons by interaction with the sodium channel. Mode of action Contact and stomach action. Uses An ingested and contact acaricide effective against a wide range of phytophagous mites on citrus, cotton, fruit, hops, ornamentals, soya beans, tobacco, vegetables and vines. It also shows insecticidal properties, in particular with high efficacy on thrips species on fruit trees, vines and vegetables. Formulation types EC; EW; SC; WP. Compatibility May not be compatible with alkaline products. Selected products: 'Rufast' (Cheminova, Bayer CropScience)

OTHER PRODUCTS
'Ardent' (Cheminova, Bayer CropScience); 'Orytis' (Cheminova, Bayer CropScience); 'Taflis' (Cheminova, Bayer CropScience); 'Tagloo' (Cheminova, Bayer CropScience)

ANALYSIS
Product analysis by hplc. Residues in plants, soil and water determined by glc with ECD.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats and mice >5000 mg/kg (for tech. in corn oil). Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to eyes and skin of rabbits. Not skin-sensitising to guinea pigs. Inhalation LC50 (4 h) for rats 1.6 mg/l air. NOEL (90 d) for male rats 2.4 mg/kg b.w., for female rats 3.1 mg/kg b.w.; (1 y) for dogs 3 mg/kg b.w. Non-mutagenic and non-teratogenic in rats (2 mg/kg b.w. daily) and rabbits (15 mg/kg b.w. daily). ADI 0.02 mg/kg. Other Low solubility in water and high adsorption on soil mean that low LC50 or LD50 values under laboratory conditions do not present significant hazard under practical field conditions. Toxicity class WHO (a.i.) U; EPA (formulation) IV

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2250, mallard ducks >1000 mg/kg. LC50 (8 d) for bobwhite quail 3275, mallard ducks 4175 mg/kg diet. Fish LC50 for rainbow trout 5.66, mirror carp 0.12 mg/l. Daphnia LC50 (48 h) 0.57 mg/l. Algae EC50 (96 h) for green algae >0.82 mg/l. Bees LC50 (48 h) (oral) 150-200 ng/bee; (48 h) (contact) 200-500 ng/bee. Worms LC50 (14 d) for earthworms >1000 mg/kg; NOEC biomass 1.6 mg/kg.

ENVIRONMENTAL FATE
Animals No metabolites found representing >10% of parent compound. Plants The main residue is the parent compound. Soil/Environment Strongly adsorbed onto soil and immobile (irrespective of pH and o.m. content); Kd 2460-2780; Koc 127 500-319 610. Soil column leaching: <1% of applied acrinathrin found in leachate. DT50 5-100 d (4 soil types). DT50 under aerobic conditions (pH 6.2, o.m. 3.1%) 52 d.