Tefluthrin 七氟菊酯

七氟菊酯

CAS: 79538-32-2
英文名称: tefluthrin
化学名称: 2,3,5,6-四氟-甲基苄基(顺)-(1RS,RS)-3-(2-氯-2,3,3-三氟丙-1-烯基)-2,2-二甲基环丙烷羧酸酯；2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(1RS,3RS)-3-(2-chloro-3,3,3-triflu
其他名称: PP993；TF3754；TF3755， Force，Forza；Komer
分子式: C17H14ClF7O2
分子量: 418.73

理化性质: 纯品为白色固体，原药为米色, 水中溶解度0.002mg/L(净化水和缓冲水，pH5和pH9)．21℃时，在许多普通溶剂中溶解，丙酮、二氯甲烷、乙酸乙酯、己烷、甲苯（21℃）大于0.5，甲醇263。。熔点为44.6℃，蒸气压8mPa(120℃)。在15～25℃时．至少稳定9个月，无特殊气味。

毒性: tefluthrin的急性毒性比标准的有机磷和氨基甲酸酯土壤杀虫剂的毒性要低, 尤其在推荐剂量下则明显低。原药对白兔皮肤和眼有轻微刺激。对禽鸟低毒，对鱼和其他水生脊椎动物的毒性高而对蚯蚓低毒。 急性经口和经皮LD50值差别很大，该值取决于载体、试验品系及其性别、年龄和生长阶段，典型的急性经口 LD50大鼠22～35（玉米油载体mg/kg），小鼠45～56；野鸭4190，鹌鹑730。急性经皮LD50:雄大鼠148～148O，雌大小鼠262。饲喂试验中无作用剂量：大鼠（2年）25mg/(kg·d）。鱼毒LC50（96h,mg/L）：虹鳟60，蓝鳃130。财蜜蜂LD50为280mg／蜜蜂（接触）、188ng／蜜峰（经口）。在田间条件下，本品被河泥和悬浮物吸附，可避兔危窖．

作用特点及杀虫谱: 本品是第1个可用作土壤杀虫剂的拟除虫菊酯，对鞘翅目、鳞翅目和双翅目昆虫高效, 可以颗粒剂、土壤喷洒或种子处理的方式旖用。它的挥发性好：可在气相中充分移行以防治土壤害虫。据认为它在土壤中杀虫是通过蒸气而不是经触杀起作用的。本品及其在土壤中的降解产物不会被地下水渗滤；在大田中的半衰期约1个月，因而它既能对害虫保持较长残效，而又不致在土壤中造成长期残留。

防治对象: 防治鞘翅目、鳞翅目和双翅目害虫效果很高。在剂量为12～150g(有效成分)/ha时，可广谱地防治土壤节肢动物，包括南瓜十二星甲、金针虫、跳甲、金龟子、甜菜隐食甲、地老虎、玉米螟、瑞典麦杆蝇等。

剂型: 3％粒剂和1．5％粒剂；乳油(100g/kg)；胶悬荆(100g／kg)。

生产方法：以三氯三氟乙烷为原料，与3，3-二甲基-4-戊烯酸乙酯加成反应，经环合、脱氯化氢、水解转变成(z)-(1RS,3RS)-3-(2-氯-3,3,3-三氟丙-1-丙烯基)-2,2-二甲基环丙甲酸(功夫酸)。对苯二甲酸与氯气在碘存在下以发烟硫酸为溶剂进行氯化制备四氯对苯二甲酸;再以DMF为催化剂与二氯亚砜反应生成四氯对苯二甲酰氯;以氟化钾为氟化剂,环丁砜为溶剂置换氟化,再与甲醇酯化得到四氟对苯二甲酸甲酯;以KBH4-LiCl为还原剂二甲醚为溶剂反应制得四氟对苯二甲基苄醇;以氯苯为溶剂在溴化氢溶液中溴化得到溴化产物;在乙醇溶液中经镁粉还原得到4-甲基-2,3,5,6-四氟苄醇; 甲基苄醇与(z)-(1RS,3RS)-3-(2-氯-3,3,3-三氟丙-1-丙烯基)-2,2-二甲基环丙甲酸(功夫酸)在催化剂二环己基碳二亚胺(DCC)和4-二甲氨基吡啶(DMAP)作用下缩合得到七氟菊酯,

生产情况：1986年由英国帝国化学工业公司（现先正达公司）开发生产。国内生产企业：连云港市华通化学有限公司；有限公司；南京金土地化工有限公司；如皋市油脂化工有限责任公司；江苏优士化学有限公司（50t/a）；贵阳柏丝特化工有限公司；江苏七洲绿色化工股份有限公司

tefluthrin
Insecticide
IRAC 3; pyrethroid

NOMENCLATURE
Common name tefluthrin (BSI, ANSI, draft E-ISO); téfluthrine ((f) draft F-ISO)
IUPAC name 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(1RS,3RS)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
Roth: 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
Chemical Abstracts name [1a,3a(Z)]-(?-(2,3,5,6-tetrafluoro-4-methylphenyl)methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate
CAS RN [79538-32-2] Development codes PP993; ICIA0993 (both ICI)

PHYSICAL CHEMISTRY
Composition Tech. material is c. 92% pure. Mol. wt. 418.7 M.f. C17H14ClF7O2 Form Colourless solid; (tech., off-white). M.p. 44.6 ºC; (tech., 39-43 ºC) B.p. 156 ºC/1 mmHg V.p. 8.4 mPa (20 ºC); 50 mPa (40 ºC) KOW logP = 6.4 (20 ºC) Henry 2 ´ 102 Pa m3 mol-1 (calc.) S.g./density 1.48 g/ml (25 ºC) Solubility In water 0.02 mg/l (purified and buffered, pH 5 and 9, 20 ºC). In acetone, hexane, toluene, dichloromethane, ethyl acetate >500, methanol 263 (all in g/l, 21 ºC). Stability Stable for at least 9 months at 15-25 ºC. Stable for >84 days at 50 ºC. Stable to hydrolysis at pH 5-7 for >30 days. At pH 9, 7% hydrolysis in 30 days. At pH 7, 27-30% loss in aqueous solution exposed to sunlight for 31 days. pKa >9 (hydrolysis prevents measurement) F.p. 124 ºC

COMMERCIALISATION
History Insecticide reported by A. R. Jutsum et al. (Proc. 1986 Br. Crop Prot. Conf. - Pests Dis., 1, 97). Introduced in Belgium (1986) by ICI Agrochemicals (now Syngenta AG). Patents EP 31199; US 4405640 Manufacturers Syngenta

APPLICATIONS
Biochemistry Acts on the nervous system of insects, disturbs the function of neurons by interaction with the sodium channel. Uses Control of a wide range of soil insect pests, particularly those of the orders Coleoptera, Lepidoptera, and Diptera, in maize, sugar beet, wheat and other crops, as granular and seed treatment products. Formulation types CS; EC; GR. Selected products: 'Force' (Syngenta); 'Fireban' (Crompton); mixtures: 'Imprimo' (+ imidacloprid) (Bayer CropScience); 'Traffic' (+ imidacloprid) (Bayer CropScience)

OTHER PRODUCTS
'Evict' (Syngenta, Bayer CropScience); 'Forca' (Syngenta); 'Forza' (Syngenta); 'Attack' (Sopra); 'Force ST' (Bayer CropScience) mixtures: 'Austral Plus' (+ anthraquinone+ fludioxonil) (Syngenta); 'Montur' (+ imidacloprid) (Bayer CropScience) Discontinued products mixtures: 'Austral' * (+ anthraquinone+ oxine-copper) (seed treatment) (La Quinoléine); 'Elyxor Star' * (+ anthraquinone+ fludioxonil) (Novartis)

ANALYSIS
Product and residue analysis by glc. Details available from Syngenta.

MAMMALIAN TOXICOLOGY
Oral Oral and percutaneous LD50 values of tefluthrin depend on such factors as carrier, the test species, its sex, age and degree of fasting; values reported sometimes differ markedly. Acute oral LD50 for male rats 22, female rats 35 (corn oil carrier), male mice 46, female mice 57 mg/kg. Skin and eye Acute percutaneous LD50 for male rats 316, female rats 177 mg/kg. Slight eye and skin irritation (rabbits). No skin sensitisation (guinea pigs). Inhalation LC50 (4 h) for male rats 0.05, female rats 0.04 mg/l. NOEL (2 y) for rats 25 mg/kg diet; (1 y) for dogs 0.5 mg/kg daily. ADI 0.005 mg/kg. Toxicity class WHO (a.i.) Ib EC classification (T+; R26/28 | R24 | N; R50)

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks 4190, bobwhite quail 730 mg/kg. Sub-acute dietary LC50 (5 d) for mallard ducks 2317, bobwhite quail 15 000 mg/kg. Fish LC50 (96 h) for rainbow trout 60, bluegill sunfish 130 ng/l. Under field conditions, adsorption of tefluthrin on bottom and suspended sediments should prevent any hazard. Daphnia EC50 (48 h) 70 ng/l. Algae Selenastrum capricornutum >1.05 mg/l. Bees LD50 (contact) 280 ng/bee; (oral) 1880 ng/bee. Worms 0.32 mg/kg soil.

ENVIRONMENTAL FATE
Animals For a study of the metabolism of tefluthrin in the goat, see Pestic. Sci., 1989, 25, 375. Plants No residues have been found on major crops treated at recommended rates (limit of detection 0.01 mg/kg). Soil/Environment DT50 in soil 150 d (5 ºC), 24 d (20 ºC), 17 d (30 ºC), partly due to loss by volatilisation. At normal application rates, there was no effect on soil microflora or earthworms.