Emamectin benzoate 甲氨基阿维菌素苯甲酸盐

用于蔬菜、果树、水稻、玉米、茶叶、葡萄、棉花防治鳞翅目类，蚜虫等刺吸性害虫等众多作物害虫。2011年6月26日到期。先正达（原默克）公司开发。2009年市场为1.45亿美元。1998年上市。

甲氨基阿维菌素苯甲酸盐

简介
分子式：Bla：C49H75NO13.C7H6O2
Blb：C48H73NO13.C7H6O2
分子量：Bla：1008.26 Blb：994.23
CAS登记号：137512-74-4
理化性状：
原药为白色或淡黄色结晶粉末；熔点：141-146℃；溶于丙酮和甲醇、微溶于水、不溶于己烷；稳定性：在通常贮存的条件下稳定。

毒 性
1.毒性及中毒症状：原药中高毒，制剂低毒（近无毒）；中毒后早期症状为瞳孔放大，行动失调，肌肉颤抖，严重时导致呕吐。
2.中毒救治：经口：立即引吐并给患者服用吐根糖浆或麻黄素，但勿给昏迷患者催吐或灌任何东西。抢救时避免给患者使用增强γ－氨基丁酸活性的药物?如（巴比妥、丙戊酸等)。大量吞服时可洗胃。
甲氨基阿维菌素苯甲酸盐(甲维盐)
是从发酵产品阿维菌素B1开始合成的一种新型高效半合成抗生素杀虫剂，它具有超高效，低毒(制剂近无毒)，无残留，无公害等生物农药的特点，与阿维菌素比较首先杀虫活性提高了1-3个数量级，对鳞翅目昆虫的幼虫和其它许多害虫及螨类的活性极高，既有胃毒作用又兼触杀作用，在非常低的剂量(0.084~2g/ha)下具有很好的效果，而且在防治害虫的过程中对益虫没有伤害，有利于对害虫的综合防治，另外扩大了杀虫谱，降低了对人畜的毒性。

甲维盐应用情况概述
1、安全环保，国家倡导，发展前景广阔（属于无残留，无公害的生物农药）；
2、超高效，杀虫谱广。
3、杀虫活性高。是阿维菌素的几十倍。
4、目前性价比最高的化合物之一。
5、目前在蔬菜、瓜果、果树、大田作物等方面得到广泛的应用。

甲维盐的缺点及解决方案
3小时光照分解50%，8小时光照分解90%。
解决方案：提升抗光解能力是保证甲维盐效果的关键。如：以松树油为基础提取的APE增效植物油溶剂，很好的弥补传统乳油的危害及不足，解决传统乳油对环境的危害（污染环境、引起白血病、癌症等），对甲维盐增效作用相对比较明显。
在对于甲维盐产品的研究中发现，在含有甲维盐的产品中，加入0.35%的抗分解剂wgwin D902，可以有效地防止甲维盐的分解，同时能提高甲维盐对鳞翅目，螨类、鞘翅目及同翅目害虫的活性，提供药效。

防治害虫
甲维盐对很多害虫具有其它农药无法比拟的活性，尤其对鳞翅目、双翅目、蓟马类超高效，如红带卷叶蛾、烟蚜夜蛾、棉铃虫、烟草天蛾、小菜蛾粘虫、甜菜夜蛾、旱地贪夜蛾、纷纹夜蛾、甘蓝银纹夜蛾、菜粉蝶、菜心螟、甘蓝横条螟、番茄天蛾、马铃薯甲虫、墨西哥瓢虫等。

生产厂家
原药生产厂家：以浙江升华拜克为代表的数十家
制剂生产厂家：国内较多，多大上百家资

emamectin benzoate
See also The BioPesticide Manual, 2nd Ed., entry 2:111
Insecticide
IRAC 6; avermectin

NOMENCLATURE
emamectin benzoate
CAS RN [155569-91-8]; formerly [137512-74-4] and [179607-18-2] Development codes MK 244 (Merck & Co.)

emamectin
Common name emamectin (BSI, pa E-ISO, ANSI); emamectine ((f) pa F-ISO)
IUPAC name A mixture containing 90% of (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-3-O-methyl-4-O-(2,4,6-trideoxy-3-O-methyl-4-methylamino-a-L-lyxo-hexopyranosyl)-a-L-arabino-hexopyranoside and 10% of (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-3-O-methyl-4-O-(2,4,6-trideoxy-3-O-methyl-4-methylamino-a-L-lyxo-hexopyranosyl)-a-L-arabino-hexopyranoside
Chemical Abstracts name (4"R)-5-O-demethyl-4"-deoxy-4"-(methylamino)avermectin A1a + (4"R)-5-O-demethyl-25-de(1-methylpropyl)-4"-deoxy-4"-(methylamino)-25-(1-methylethyl)avermectin A1a (9:1)
CAS RN [119791-41-2]; formerly [123997-28-4] and [137335-79-6]

PHYSICAL CHEMISTRY
emamectin benzoate
Composition A mixture of emamectin B1a (³90%) and emamectin B1b (£10%), as their benzoate salts. Mol. wt. 1008.3 (B1a); 994.2 (B1b) M.f. C56H81NO15 (B1a); C55H79NO15 (B1b) Form White to off-white powder. M.p. 141-146 °C V.p. 4 ´ 10-3 mPa (21 °C) KOW logP = 5.0 (pH 7) S.g./density 1.20 (23 °C) Solubility In water 0.024 g/l (pH 7, 25°C).

emamectin
Mol. wt. 886.1 (B1a); 872.1 (B1b) M.f. C49H75NO13 (B1a); C48H73NO13 (B1b)

COMMERCIALISATION
Production Isolated from fermentation of Streptomyces avermitilis, a naturally occuring soil Actinomycete. History Discovery and initial development was by Merck & Co., Inc. (now Syngenta AG). First sales in Israel and Japan in 1997. Manufacturers Merck & Co.

APPLICATIONS
emamectin benzoate
Biochemistry Acts by stimulating the release of g-aminobutyric acid, an inhibitory neurotransmitter, thus causing paralysis. Mode of action Non-systemic insecticide which penetrates leaf tissues by translaminar movement. Paralyses the lepidoptera, which stop feeding within hours of ingestion, and die 2-4 dat. Uses For control of Lepidoptera on vegetables, brassicas and cotton, at up to 16 g/ha, and in pine trees, at 5-25 g/ha. Formulation types EC; SG. Selected products: 'Banlep' (Syngenta); 'Denim' (Syngenta); 'Proclaim' (Syngenta)

ANALYSIS
Product and residues determined by hplc. Details available from Syngenta.

MAMMALIAN TOXICOLOGY
emamectin benzoate
Oral Acute oral LD50 for rats 76-89 mg/kg. Skin and eye Acute dermal LD50 for rabbits >2000 mg/kg. It is not irritant to skin, and has no sensitising potential. Inhalation LC50 (4 h) for rats 2.12-4.44 mg/m3. NOEL (1 y) for dogs 0.25 mg/kg b.w. ADI 0.0025 mg/kg. Other Not tumorigenic. Toxicity class WHO (a.i.) II (company classification)

ECOTOXICOLOGY
emamectin benzoate
Birds Acute oral LD50 for mallard ducks 46, bobwhite quail 264 mg/kg. Dietary LC50 (8 d) for mallard ducks 570, bobwhite quail 1318 ppm. Fish LC50 (96 h) for rainbow trout 174, sheepshead minnow 1430 mg/l. Daphnia LC50 0.99 mg/l. Bees Toxic to bees. Worms LC50 >1000 mg/kg dry soil. Other beneficial spp. Safe to a wide range of beneficial insects, due rapid breakdown of the a.i., limiting contact activity to <48 h.

ENVIRONMENTAL FATE
Animals Emamectin benzoate is partially metabolised but rapidly cleared (DT50 following oral dosing 34-51 h), indicating that it has no potential for bioaccumulation. Plants Metabolism has been investigated in lettuce, cabbage and sweet corn. It is non-systemic, and rapidly degrades in sunlight to various complex residues in which undegraded parent is the only significant residue. The residues were very low. Soil/Environment Rapidly degraded.