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Abamectin 阿维菌素

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阿维菌素
 
应用类别:杀虫剂,杀螨剂
化学类别:大环内酯双糖类
 
命名:
中文通用名:阿维菌素
别名:灭虫丁;灭虫灵;阿巴丁;螨虫素;7051杀虫素;齐螨素;爱福丁;克螨灵;爱弗菌素
英文通用名:abamectin
中文化学名:5-O-双甲基阿维菌素A1a(i)与5-O-去甲基-25-去(1-甲基丙基)-25-(1-甲基乙基)阿维菌素A1a(ii)(CAS)
英文化学名:5-O-demethylavermectin A1a (i) mixture with 5-O-demethyl-25-de(1-methylpropyl)-25-(1-methylethyl)avermectin A1a (ii)  (CAS)
CAS No. [71751-41-2] (abamectin); [65195-55-3] (i); [65195-56-4] (ii) 
 
理化性质:
分子式:C48H72O14(B1a)·C47H70O14(B1b)   
分子量:(873.09);(859.06)   
密度:1.16   
熔点:150-155 ℃   
外观:原药精粉为白色或黄色结晶(含B1a≥90%)
蒸气压:<3.7 ´ 10-3 mPa (25 °C) 
熔点:161.8-169.4 °C (decomp.) 
溶解度:水中7-10 mg/l (20 ºC). 在甲苯中 350, 丙酮中100, 异丙醇 70, 氯仿 25, 乙醇 20, 甲醇 19.5, 正丁醇10, 环己烷 6 (g/l, 21 ºC). 
稳定性:在25 ℃,pH5-9 的溶液中无分解现象。对强酸强碱敏感。光不稳定,紫外线照射可导致转化,先转化为8,9-Z-异构体,然后转化为未识别的降解产物。 
KOW(油水分配系数): logP=4.4±0.3(pH 7.2, 室温)。

分析方法:
产品含量分析 高效液相色谱,紫外探测器
残留分析 高效液相色谱,通过转换为荧光产物的荧光检测法 . 参考 T. Wehner et al. in Comp. Anal. Profiles, Chapt. 4. 

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毒理数据:
经口 急性经口LD50 (香油做溶剂) 大鼠10毫克/千克, 小鼠 13.6 毫克/千克; (水做溶剂) for 大鼠 221 毫克/千克. 
皮肤及眼 兔急性经皮 LD50 >2000 毫克/千克. 对皮肤无刺激作用,对眼晴有轻微刺激作用(兔). 
ADI每日容许摄入量): (JMPR) 0.002 毫克/千克 体重 [1997] (以阿维菌素和其8,9-Z-异构体总计); 0.001 毫克/千克 体重  [1995] (残留物不含D-8,9-异构体). 
其它 无致突变作用(Ames test). 
毒性级别 EPA (制剂) IV 
慢性毒性:大鼠三代繁殖试验,无作用剂量为0.12毫克/千克/天。大鼠两年无作用剂量为2毫克/ 千克/天。

环境毒理数据:
野鸭急性经口LD50为86.4毫克/千克, 鹌鹑急性经口LD50大于2000毫克/千克。 
虹鳟鱼96小时LC50为3.2微克/升,蓝鳃太阳鱼96小时LC50为9.6微克/升。
水蚤: EC50 (48 h) 0.34 ppb. 
藻类: 月芽藻 (Pseudokirchneriella subcapitata)72 小时>100 mg/l. 
其它水生生物:桃红对虾96小时LC50 1.6ppb.  , 青蟹(Callinectes sapidus) 96小时LC50 为153 ppb. 
蜜蜂 对蜜蜂高毒,经口LD50为0.009微克/头,接触LD50为0.002微克/头,但残留在叶面的LT50为4小时,4小时以后残留在叶面的药剂对蜜蜂低毒。. 
蠕虫 对蚯蚓28天LC50 为 28 毫克/千克土壤. 

环境降解与影响
动物 快速消除 (96小时内消除80-100%), 主要通过粪便消除,尿路仅排除0.5-1.4%。
植物 在三种不同的植物中的代谢及降解相似,主要通过植物表面的光解作用进行。残留物为阿维菌素B1和8,9-z-阿维菌素B1光异构体联合残留。
土壤/环境 与土壤紧密结合,被土壤中的微生物快速降解。无生物富集。

作用及使用:
生物化学: 阿维菌素对螨类和昆虫具有胃毒和触杀作用,不能杀卵。作用机制与一般杀虫剂不同的是干扰神经生理活动,刺激释放γ-氨基丁酸,而氨基丁酸对节肢动物的神经传导有抑制作用。螨类成虫、若虫和昆虫幼虫与阿维菌素接触后即出现麻痹症状,不活动、不取食,2~4天后死亡。因不引起昆虫迅速脱水,所以阿维菌素致死作用较缓慢。
作用方式 触杀及胃毒,极小的植物内吸作用,但会发生叶片转移。.
防治对象:活动阶段的螨类,潜叶蝇,科罗拉多甲虫等。也可用于防治红火蚁。
作物:观赏植物,棉花,柑橘类水果,坚果仁果类水果,蔬菜,谷物,土豆,和其他作物。
剂量:(有效成份)螨类5.6 - 28 克/公顷, 斑潜蝇克/公顷。
药害: 与克菌丹混用时可能对仁果造成药害。. 
制剂 EC.
配伍 不能与克菌丹同用。 

田间应用举例:
① 防治小菜蛾、菜青虫,在低龄幼虫期使用1000-1500倍2%阿维菌素乳油+1000倍1%甲维盐,可有效地控制其为害,药后14天对小菜蛾的防效仍达90-95%,对菜青虫的防效可达95%以上。
② 防治金纹细蛾、潜叶蛾、潜叶蝇、美洲斑潜蝇和蔬菜白粉虱等害虫,在卵孵化盛期和幼虫发生期用3000-5000倍1.8%阿维菌素乳油+1000倍高氯喷雾,药后7-10天防效仍达90%以上。
③防治甜菜夜蛾,用1000倍1.8%阿维菌素乳油,药后7-10天防效仍达90%以上。
④防治果树、蔬菜、粮食等作物的叶螨、瘿螨、茶黄螨和各种抗性蚜虫,使用4000-6000倍1.8%阿维菌素乳油喷雾。
⑤防治蔬菜根结线虫病,按每亩用500毫升,防效达80-90%。

中毒急救及注意事项:
见:
阿维菌素原药MSDS
阿维菌素制剂MSDS
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生产工艺:
菌种培养→发酵→过滤→萃取→结晶→成品
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产品规格/行业标准:
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研发,商业历史,国外产品:见英文资料部分

国主要厂家
原药:华北制药,齐鲁制药,河北威远,大庆志飞,浙江海正,浙江钱江生化,升华拜克,桂林集琦等.华北制药爱诺公司阿维精粉专供先正达产量亚洲最大。   
制剂:厂家较多,价格参差不齐,质量差异很大。   
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abamectin
See also The BioPesticide Manual, 2nd Ed., entry 2:97
Insecticide, acaricide
IRAC  6; avermectin


  abamectin

 

NOMENCLATURE
Common name abamectin (BSI, draft E-ISO, ANSI); abamectine ((f) draft F-ISO)
IUPAC name (10E,14E,16E,22Z)-(1R,4S,5'S,6S,6'R,8R,12S,13S,20R,21R,24S)-6'-[(S)-sec-butyl]-21,24-dihydroxy-5',11,13,22-tetramethyl-2-oxo-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6-spiro-2'-(5',6'-dihydro-2'H-pyran)-12-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-a-L-arabino-hexopyranosyl)-3-O-methyl-a-L-arabino-hexopyranoside (i) mixture with (10E,14E,16E,22Z)-(1R,4S,5'S,6S,6'R,8R,12S,13S,20R,21R,24S)-21,24-dihydroxy-6'-isopropyl-5',11,13,22-tetramethyl-2-oxo-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6-spiro-2'-(5',6'-dihydro-2'H-pyran)-12-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-a-L-arabino-hexopyranosyl)-3-O-methyl-a-L-arabino-hexopyranoside (ii) (4:1) 
Chemical Abstracts name 5-O-demethylavermectin A1a (i) mixture with 5-O-demethyl-25-de(1-methylpropyl)-25-(1-methylethyl)avermectin A1a (ii) 
Other names avermectin B1 
CAS RN [71751-41-2] (abamectin); [65195-55-3] (i); [65195-56-4] (ii) 
EEC no. 265-610-3 (avermectin B1a); 265-611-9 (avermectin B1b) 
Development codes MK-0936 (Merck & Co.); C-076 (Ciba); L-676,863 

 

PHYSICAL CHEMISTRY
Composition A mixture containing ³80% avermectin B1a (i) and £20% avermectin B1b (ii). 
Mol. wt. 873.1 (avermectin B1a); 859.1 (avermectin B1b) 
M.f. C48H72O14 (avermectin B1a); C47H70O14 (avermectin B1b) 
Form Colourless to pale yellow crystals. 
M.p. 161.8-169.4 °C (decomp.) 
V.p. <3.7 ´ 10-3 mPa (25 °C) 
KOW logP = 4.4?.3 (pH 7.2, room temperature) 
Henry 2.7 ´ 10-3 Pa m3 mol-1 (25 °C) 
S.g./density 1.18 (22 °C) 
Solubility In water 7-10 mg/l (20 ºC). In toluene 350, acetone 100, isopropanol 70, chloroform 25, ethanol 20, methanol 19.5, n-butanol 10, cyclohexane 6 (all in g/l, 21 ºC). 
Stability Stable to hydrolysis in aqueous solutions at pH 5, 7, and 9 (25 ºC). Sensitive to stronger acid and base. U.V. irradiation causes conversion first to the 8,9-Z- isomer, then to unidentified decomposition products. 
Specific rotation [a]D22 +55.7?(c=0.87, CHCl3) 

 

COMMERCIALISATION
Production Isolated from fermentation of Streptomyces avermitilis, a naturally occuring soil Actinomycete. 
History Anthelmintic and acaricidal activity of a group of chemically related compounds, the avermectins, reported by I. Putter et al. (Experientia, 1981, 37, 963). A mixture of two of these, avermectin B1a (i) and avermectin B1b (ii) introduced in 1985 as an acaricide and insecticide by Merck Sharp & Dohme Agvet (now Syngenta AG). 
Manufacturers Jingma; Sharda; Sinon; Syngenta; Tide

 

APPLICATIONS
Biochemistry Acts by stimulating the release of g-aminobutyric acid, an inhibitory neurotransmitter, thus causing paralysis. See M. J. Turner & J. M. Schaeffer in Ivermectin and Abamectin, W. C. Cambell ed., Springer-Verlag, New York (1989) p. 73. 
Mode of action Insecticide and acaricide with contact and stomach action. Has limited plant systemic activity, but exhibits translaminar movement. 
Uses Control of motile stages of mites, leaf miners, suckers, Colorado beetles, etc. on ornamentals, cotton, citrus fruit, pome fruit, nut crops, vegetables, potatoes, and other crops. Application rates are 5.6 to 28 g/ha for mite control, 11 to 22 g/ha for control of leaf miners. Also used for control of fire ants.
Phytotoxicity May be phytotoxic to pome fruit when mixed with captan. 
Formulation types EC.
Compatibility Not compatible with captan. 
Selected products: 'Agrimec' (Syngenta); 'Dynamec' (Syngenta); 'Vertimec' (Syngenta); 'Abacide' (Mauget); 'Abamex' (Vapco); 'Biok' (Cequisa); 'Gilmectin' (Gilmore); 'Romectin' (Rotam); 'Satin' (Sanonda); 'Timectin' (Tide); 'Vibamec' (Vipesco)

 

OTHER PRODUCTS
'Affirm' (fire ant control) (Syngenta); 'Agri-Mek' (citrus) (Syngenta); 'Avid' (ornamentals) (Syngenta); 'Clinch' (Syngenta); 'Zephyr' (cotton) (Syngenta); 'Agromec' (Chemvet); 'Apache' (AFRASA); 'Belpromec' (Probelte); 'Crater' (AFRASA); 'Vamectin 1.8 EC' (IQV); 'Vapcomic' (Vapco); 'Vivid' (Florida Silvics)
Discontinued products: 'Agrimectin' * (Agro Chemicals)

 

ANALYSIS
Product analysis by hplc with u.v. detection.
Residues by conversion to a fluorescent product followed by hplc with fluorescence detection. See T. Wehner et al. in Comp. Anal. Profiles, Chapt. 4. 

 

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 74, 80, 82 (see part 2 of the Bibliography). G. Lankas & L. R. Gordon in Toxicology in Ivermectin and Abamectin, W. C. Campbell ed., Springer-Verlag (1989) pp. 89-112. 
Oral Acute oral LD50 (in sesame oil) for rats 10, mice 13.6 mg/kg; (in water) for rats 221 mg/kg. 
Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Mild eye irritant; non-irritating to skin (rabbits). 
ADI (JMPR) 0.002 mg/kg b.w. [1997] (for sum of abamectin and 8,9-Z- isomer); 0.001 mg/kg b.w. [1995] (for residues not containing D-8,9-isomer). 
Other Non-mutagenic in the Ames test. 
Toxicity class EPA (formulation) IV 

 

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks 84.6, bobwhite quail >2000 mg/kg. 
Fish LC50 (96 h) for rainbow trout 3.2, bluegill sunfish 9.6 mg/l. 
Daphnia EC50 (48 h) 0.34 ppb. 
Algae (72 h) for Pseudokirchneriella subcapitata >100 mg/l. 
Other aquatic spp. LC50 (96 h) for pink shrimp (Panaeus duorarum) 1.6, blue crab (Callinectes sapidus) 153 ppb. 
Bees Toxic to bees. 
Worms LC50 (28 d) for earthworms 28 mg/kg soil.

 

ENVIRONMENTAL FATE
Animals Rapidly eliminated (80-100% in 96 h), mainly via faeces; urinary excretion was 0.5-1.4%. 
Plants Degradation/metabolism in each of three different plants is similar and occurs predominantly by photolysis on the plant surfaces. The definition of the residues is thus expressed as the combined residues of avermectin B1 and its 8,9-Z-avermectin B1 photoisomer. 

Soil/Environment: Binds tightly to soil, with rapid degradation by soil micro-organisms. No bioaccumulation.