Tau-fluvalinate 氟胺氰菊酯

氟胺氰菊酯

CAS号：102851-06-9
化学名称：
（RS）-α-氰基-3-苯氧基苄基N-（2-氯-α，α-α-三氟-对-甲苯基）-D-缬氨酸酯；(RS)-α-cyano-3-phenoxybenzyl N-(2-chloro-α,α,α-trifluoro-p-tolyl)-D-valinate;
其他名称：马扑立克(Mavrik)
分子式：C26H22CLF3N2O3
分子量：502.9

理化性质：其原药为粘稠的黄色抽状液体，密度：1.29，沸点：大于450℃（外推法）℃，闪点：10℃，蒸气压：大于0.013mPa(25℃)，溶解度：水0.002mg/kg、丙酮＞1000g/kg、甲醇760g/kg、氯仿1000g/kg（25℃），任意溶于芳烃、二氯甲烷、乙醚。稳定性：暴露在日光下DT50为9.3～10.7分钟（水溶液，缓冲至pH5。），约1天（在玻璃上呈薄膜），13天（在土壤表面）。

毒性LD50(mg/kg)：大鼠急性经口 LD50：雄 282，雌261；兔急性经皮LD50大于2000，对兔皮肤有轻微刺激作用，对兔眼睛有中度刺激作用。大鼠急性吸入LC50(4h)大于0.56mg(以240g/L乳油）/空气。

作用特点及杀虫谱：本品具触杀和胃毒作用，是高效广谱叶页施用的杀虫、杀螨剂。以 56～168（a i．）／ha可有效地防洽棉花、烟草、果树、观赏植物、蔬菜、树木和葡萄上的蚜虫、叶蝉、鳞翅目、缨翅目害虫、温室粉属和叶螨等，如烟芽夜蛾、棉铃虫、棉红铃虫、波纹夜蛾、蚜虫、盲蝽象、叶螂、烟天蛾、烟草跳甲、菜粉蝶、菜蛾、甜菜夜蛾、玉米螟、苜蓿叶象甲等。25～75mg／L可防治苹果、葡萄上的蚜虫，100～200mg／L可防治桃和梨树上的螨类害虫。对蜜蜂蜂螨有特效。
生产方法：

（1）α-溴代代异戊酸用氯化亚矾进行氯化，生成α-溴代异戊酰氯，然后在吡啶存在下，与α－氰基-3-苯氧基苄醇反应，生成物与2-氯-4-三氟甲基苯胺反应，即可得氟胺氰菊酯。（2）α-溴代异戊酸，与对三氟甲基苯胺、N-氯代琥珀酰亚胺反应，主成物最后与α－氰基-3-苯氧基苄醇反应，，即制得氟胺氰菊酯。
生产情况：瑞士山德士公司，汪氏蜂业四川资阳蜂药厂

tau-fluvalinate
Insecticide, acaricide
IRAC 3; pyrethroid

NOMENCLATURE
Common name tau-fluvalinate (BSI, draft E-ISO)
IUPAC name (RS)-a-cyano-3-phenoxybenzyl N-(2-chloro-a,a,a-trifluoro-p-tolyl)-D-valinate
Chemical Abstracts name cyano(3-phenoxyphenyl)methyl N-[2-chloro-4-(trifluoromethyl)phenyl]-D-valinate
CAS RN [102851-06-9] tau-fluvalinate; [69409-94-5] fluvalinate (DL- isomers) - many references in the literature have been made, erroneously, to the latter rather than the former Development codes SAN 527 I (Sandoz); MK 128

PHYSICAL CHEMISTRY
Composition Material is a 1:1 mixture of (R)-a-cyano-, 2-(R)- and (S)-a-cyano-, 2-(R)- diastereoisomers. Mol. wt. 502.9 M.f. C26H22ClF3N2O3 Form Viscous amber oil, with a moderate or weak sweetish odour (tech.). B.p. 164 ºC/0.07 mmHg (tech.) V.p. 9 ´ 10-8 mPa (20 °C) KOW logP = 4.26 (25 ºC) Henry 4.04 ´ 10-5 Pa m3 mol-1 (calc.) S.g./density 1.262 (25 ºC) Solubility In water 1.03 ppb (pH 7, 20 ºC). Soluble in toluene, acetonitrile, isopropanol, dimethylformamide, n-octanol; in iso-octane 108 g/l. Stability Tech. material is stable for 2 years at room temperature (20-28 ºC). Undergoes decomposition on exposure to sunlight; DT50 9.3-10.7 min (aqueous solution buffered pH 5), c. 1 d (thin film on glass), 13 d (on soil surface). On hydrolysis (25 ºC), DT50 for a 9 ppb aqueous solution was 48 d (pH 5), 38.5 d (pH 7), 1.1 d (pH 9). F.p. 90 ºC (tech.; Pensky-Martens closed cup)

COMMERCIALISATION
History Insecticidal and acaricidal activity of the various stereoisomers reported by C. A. Henrick et al. (Pestic. Sci., 1980, 11, 224) and by R. J. Anderson (J. Agric. Food Chem., 1985, 33, 508). Tau-fluvalinate (introduced in 1985) has replaced fluvalinate; both introduced by Zoecon Corp. and purchased by Sandoz Agro AG (became Novartis Crop Protection AG). Sold to Makhteshim-Agan Industries in 2000. Patents US 4243819

APPLICATIONS
Biochemistry Acts on the nervous system of insects, disturbs the function of neurons by interaction with the sodium channel. Mode of action Insecticide and acaricide with contact and stomach action. Uses Control of a wide range of insects (including Lepidoptera, aphids, thrips, leafhoppers, whitefly, etc.) and spider mites on cereals, oilseed rape and potatoes, at 36-48 g/ha, on vines, vegetables and sunflowers, at up to 72 g/ha, and in orchards at up to 144 g/ha; also on indoor and outdoor ornamentals, cotton, tea, tobacco, and turf. Also used (as 'Apistan') for control of Varroa jacobsoni in beehives. Formulation types EC; EW; UL; Controlled release strips; VP. Compatibility Incompatible with alkaline materials. Selected products: 'Klartan' (Makhteshim-Agan); 'Mavrik Aquaflow' (Makhteshim-Agan)

OTHER PRODUCTS
'Apistan' (Wellmark); 'Mavrik' (Makhteshim-Agan); 'Spur' (Makhteshim-Agan); 'Talita' (Makhteshim-Agan) mixtures: 'Mavrik B' (+ thiometon) (Makhteshim-Agan); 'Mavrik Systo' (+ thiometon) (Makhteshim-Agan) Discontinued products: 'Yardex' * (Sandoz)

ANALYSIS
Product analysis of pyrethroids reviewed by E. Papadopoulou-Mourkidou in Comp. Analyt. Profiles. By hplc (W. L. Fitch et al., Anal. Methods Pestic. Plant Growth Regul., 1984, 13, 79) or by glc with FID. Residues determined by glc with ECD (idem, ibid.; AOAC Methods, 17th Ed., 998.01).

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for female rats 261, male rats 282 mg a.i. (in corn oil)/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg; slight skin irritant, mild eye irritant (rabbits). Inhalation LC50 (4 h) for rats >0.56 mg/l air (as 240 g/l EW formulation). NOEL for rats 1 mg/kg b.w. daily. ADI 0.01 mg/kg b.w. Toxicity class WHO (a.i.) U; EPA (formulation) II EC classification Xn; R22| Xi; R38| N; R50, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2510 mg/kg. Dietary LC50 (8 d) for bobwhite quail and mallard ducks >5620 mg/kg diet. Fish LC50 (96 h) for bluegill sunfish 0.0062, rainbow trout 0.0027, carp 0.0048 mg/l. Daphnia LC50 (48 h) 0.001 mg/l. Algae LC50 for Scenedesmus subspicatus >2.2 mg/l. Bees Not hazardous to bees at recommended doses; LD50 (24 h, contact topical) 6.7 mg tech./bee; (ingestion) 163 mg tech./bee. Worms LC50 (14 d) >1000 ppm. Other beneficial spp. Generally safe to moderately toxic to beneficials, except spiders, predatory mites, some lady beetles and some predatory bugs.

ENVIRONMENTAL FATE
Animals In rats, following oral administration, c. 90% is excreted within 4 d, of which 20-40% is in the urine and 60-80% in the faeces. The principal metabolites are "anilino acid", 3-phenoxybenzoic acid (3-PBA) and 4'-3-PBA as faecal metabolites, and 4'-3-PBA, 3-PBA and 3-phenoxybenzyl alcohol as urinary metabolites. Plants The parent compound itself accounts for >90% of the residue following treatment with tau-fluvalinate. Minor residues include decarboxyfluvalinate, "anilino acid", haloaniline, 3-PBA and 4'-hydroxy-3-PBA. DT50 2-6 w. Soil/Environment In soil under aerobic conditions (lab.), DT50 12-92 d. Primary metabolites include the corresponding anilino acids and the parent aniline. Koc(adsorption) >110 000, (desorption) >39 000.