Tebufenozide 虫酰肼

虫酰肼

中文名 虫酰肼
英文通用名 tebufenozide
化学名称 N - 叔丁基 -N-（4- 乙基苯甲酰基）- 3，5 - 二甲基苯甲酰肼
商品名：米满，Confir，Mimic
分子式：C22H28N2O2
分子量：352
CAS登记号：112410-23-8
剂 型：20%胶悬剂，可湿性粉剂

理化性质
纯品为白色粉末。熔点191℃；水中溶解度（20℃），在其他溶剂中溶解度不大，94℃下贮存7天稳定，25℃，PH=7水溶液中光照稳定。蒸气压为3×10-8mmHg(25℃)。KOWlogP=4.25(PH＝7)。虫酰肼属蜕皮激素类杀虫剂，通过干扰昆虫的正常发育使害虫蜕皮而死，低毒，大鼠急性经口LD50大于5000mg / kg，对人、哺乳动物、鱼类和蚯蚓安全无害，对环境十分安全，是综合防治中理想安全的杀虫剂。其纯品为白色固体。

作用特点：
虫酰肼是非甾族新型昆虫生长调节剂，是最新研发的昆虫激素类杀虫剂。虫酰肼杀虫活性高，选择性强，对所有鳞翅目幼虫均有效，对抗性害虫棉铃虫、菜青虫、小菜蛾、甜菜夜蛾等有特效。并有极强的杀卵活性，对非靶标生物更安全。虫酰肼对眼睛和皮肤无刺激性，对高等动物无致畸、致癌、致突变作用，对哺乳动物、鸟类、天敌均十分安全。

用 途：
主要用于防治柑桔、棉花、观赏作物、马铃薯、大豆、烟草、果树和蔬菜上的蚜科、叶蝉科、鳞翅目、斑潜蝇属、叶螨科、缨翅目、根疣线虫属、鳞翅目幼虫如梨小食心虫、葡萄小卷蛾、甜菜夜蛾等等害虫。 本品主要用于持效期2～3周。对鳞翅目害虫有特效。高效，亩用量0.7～6g(活性物)。用于果树、蔬菜、浆果、坚果、水稻、森林防护。

毒 性：
急性口服LD50大鼠、小鼠>5000mg/kg；急性经皮LD50大鼠>5000mg/kg；眼刺激、皮肤刺激：极少；诱变性：阴性；环境毒性：野鸭8天日食量LC50>5000mg/kg，虹鳟鱼96小时LC50：5.7mg/L，水蚤属48小时EC503.8mg/L，蜜蜂96小时接触LD50>234μg/只，对幼蜜蜂生长无影响；有益节肢动物：在实验室条件下，对食肉瓢虫、食肉螨和一些食肉黄蜂和蜘蛛等进行试验，显示阴性

使用方法：
①防治枣、苹果、梨、桃等果树卷叶虫、食心虫、各种刺蛾、各种毛虫、潜叶蛾、尺蠖等害虫，用20％悬浮剂1000-2000倍液喷雾。
②防治蔬菜、棉花、烟草、粮食等作物的抗性害虫棉铃虫、小菜蛾、菜青虫、甜菜夜蛾及其他鳞翅目害虫，用20%悬浮剂1000-2500倍液喷雾。

tebufenozide
Insecticide
IRAC 18; diacylhydrazine

NOMENCLATURE
Common name tebufenozide (BSI, pa E-ISO, ANSI)
IUPAC name N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide
Chemical Abstracts name 3,5-dimethylbenzoic acid 1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide
CAS RN [112410-23-8] Development codes RH-5992; RH-75922 (both Rohm & Haas)

PHYSICAL CHEMISTRY
Mol. wt. 352.5 M.f. C22H28N2O2 Form Off-white powder. M.p. 191 ºC V.p. <1.56 ´ 10-4 mPa (25 ºC, gas saturation method) KOW logP = 4.25 (pH 7) Henry <6.59 ´ 10-5 Pa m3 mol-1 (calc.) S.g./density 1.03 (20 ºC, pycnometer method) Solubility In water 0.83 ppm (25 ºC). Slightly soluble in organic solvents. Stability Stable at 94 ºC for 7 d. Stable to light in pH 7 aqueous solution (25 ºC). Stable in dark, sterile water 30 d (25 ºC). DT50 in natural pond water 67 d, in light, 30 d (25 ºC).

COMMERCIALISATION
History Reported by J. J. Heller et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1992, 1, 59). Developed in USA by Rohm & Haas Co. (now Dow AgroSciences), under licence in Europe by AgrEvo GmbH (now Bayer CropScience) and in Japan by Hokko Chemical Industry Co., Ltd and Nihon Nohyaku Co., Ltd. Patents US 4985461 Manufacturers Dow AgroSciences

APPLICATIONS
Biochemistry Ecdysone agonist which acts by binding to the receptor site of the insect moulting hormone, ecdysone. Mode of action Lethally accelerates moulting process. Uses Control of lepidopteran larvae on rice, fruit, row crops, nut crops, vegetables, vines, and forestry, generally at 0.06-0.3 lb/a. Formulation types DP; GR; SC; SU; WP. Selected products: 'Confirm' (Dow AgroSciences); 'Mimic' (forestry) (Dow AgroSciences); mixtures: 'Conidan' (+ imidacloprid) (Korea) (Bayer CropScience)

OTHER PRODUCTS
'Romdan' (Indonesia, Japan) (Dow AgroSciences, Nihon Nohyaku)

ANALYSIS
Details from Dow AgroSciences.

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 77, 79, 92 (see part 2 of the Bibliography). Oral Acute oral LD50 for rats and mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Non-irritating to eyes and skin (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for male rats >4.3, female rats >4.5 mg/l. NOEL (24 mo) for rats 5.5 mg/kg b.w. daily; (18 mo) for mice 8.1 mg/kg b.w. daily; (12 mo) for dogs 1.9 mg/kg b.w. daily. ADI (JMPR) 0.02 mg/kg b.w. [1996, 2001]. Other Negative in the Ames test, reverse mutation assay, mammalian point mutation (CHO), in vivo and in vitro cytogenetic assay, and in vitro unscheduled DNA synthesis test. Toxicity class EPA (formulation) III (2 SC) EC classification N; R51, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for quail >2150 mg/kg. Dietary LC50 (8 d) for mallard ducks and quail >5000 mg/kg. Fish LC50 (96 h) for rainbow trout 5.7, bluegill sunfish 3.0 mg/l. Daphnia LC50 (48 h) 3.8 mg/l. Algae EC50 (120 h) for Selenastrum >0.64 mg/l; (96 h) for Scenedesmus 0.23 mg/l. Other aquatic spp. LC50 (96 h) for mysid shrimp (Mysidopsis bahia) 1.4, Eastern oyster (Crassostrea virginica) 0.64 mg/l. Bees LD50 (96 h, contact) for honeybees >234 mg/bee. Worms LC50 for earthworms >1000 mg/kg. Other beneficial spp. Safe to predatory mites, wasps and other beneficial species.

ENVIRONMENTAL FATE
Animals In the rat, 16 whole-molecule metabolites are formed as a result of oxidation of the alkyl substituents of the aromatic rings, primarily at the benzylic positions. Plants In apples, grapes, rice and sugar beet, the major component is unchanged tebufenozide. Metabolites which are detected in small amounts result from oxidation of the alkyl substituents of the aromatic ring, primarily at the benzylic positions. Soil/Environment Metabolic DT50 in soil 7-66 d (7 soil types); for aerobic, aquatic soil 100 d (25 ºC, 3 soil types); for anaerobic, aquatic metabolism 179 d (25 ºC, silt loam). DT50 for field dissipation 4-53 d (12 sites). Koc 351-894. Field dissipation studies indicate no mobility below 30 cm.