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中文通用名称： 弥拜菌素
英文通用名称： milbemectin
商品名称： Milbeknock
试验代号： SI-8601、B-41、E-187
化学名称：
(10E,14E,16E,22Z)-(1R,4S,5'S,6R,6'R,8R,13R,20R,21R,24S)-21,24-dihydro-5',6 ',11,13,22-pentamethyl-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6-spiro-2'-tetrahydropyran-2-one (milbemectin A3)
(10E,14E,16E,22Z)-(1R,4S,5'S,6R,6' R,8R,13R,20R,21R,24S)-6' -ethyl-21,24-dihy-dro-5',11,13,22-tetramethyl-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6-spiro-2'-tetrahydropyran-2-one (milbemectin A4)
CA主题索引名及CAS登录号:
milbemectin A 3：(6R,25R)-5-O-demethyl-28-deoxy-6,28-epoxy-25-methyl milbe-mectin B
[51596-10-2]；
milbemectin A 4：(6R,25R)-5-O-demethyl-28-deoxy-6,28-epoxy-25-ethyl milbe-mectin B
[51596-11-3]
理化性质：
milbemectin A 3：纯品熔点212-215℃，密度1.1270(25℃)。蒸气压1.3×10-8Pa(25℃)。水中溶解度(20℃)：0.88ppm，其它溶剂中溶解度(20℃，g/l) ：甲醇 64.8、乙醇41.9、丙酮 66.1、乙酸乙酯 69.5、苯 143.1、正己烷1.4。
milbemectin A 4：纯品熔点212-215℃，密度1.1270(25℃)。蒸气压1.3×10-8Pa(25℃)。水中溶解度(20℃)：7.2ppm，其它溶剂中溶解度(20℃，g/l) ：甲醇458.8、乙醇234.0、丙酮 365.3、乙酸乙酯 320.4、苯 524.2、正己烷6.5。
毒性： 急性经口LD50(mg/kg)：大鼠雄 762、雌 456，小鼠雄 324、雌 313；大、小鼠急性经皮LD50：>5000mg/kg。无 “三致” 。
应用： 主要用于果树如柑橘等防治各种害螨。活性与阿维菌素相似，但毒性低，比阿维菌素安全。
开发公司： 三共公司
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milbemectin
See also The BioPesticide Manual, 2nd Ed., entry 2:124
Acaricide, insecticide
IRAC 6
NOMENCLATURE
Common name milbemectin (BSI, pa E-ISO)
IUPAC name A mixture of: (10E,14E,16E,22Z)-(1R,4S,5'S,6R,6'R,8R,13R,20R,21R,24S)-21,24-dihydroxy-5',6',11,13,22-pentamethyl-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6-spiro-2'-tetrahydropyran-2-one and (10E,14E,16E,22Z)-(1R,4S,5'S,6R,6'R,8R,13R,20R,21R,24S)-6'-ethyl-21,24-dihydroxy-5',11,13,22-tetramethyl-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6-spiro-2'-tetrahydropyran-2-one in the ratio 3 to 7
Chemical Abstracts name A3: (6R,25R)-5-O-demethyl-28-deoxy-6,28-epoxy-25-methylmilbemycin B;
A4: (6R,25R)-5-O-demethyl-28-deoxy-6,28-epoxy-25-ethylmilbemycin B
CAS RN [51596-10-2] A3; [51596-11-3] A4 Development codes B-41; E-187; SI-8601 (Sankyo)
PHYSICAL CHEMISTRY
Composition A mixture of the homologues milbemycin A3 (methyl) and milbemycin A4 (ethyl) in the ratio 3 to 7. Mol. wt. A3: 528.7; A4: 542.7 M.f. A3: C31H44O7; A4: C32H46O7 Form White, crystalline powder. M.p. A3: 212-215 °C; A4: 212-215 °C V.p. A3: <1.3 ´ 10-5; A4: <1.3 ´ 10-5 (both in mPa, 20 °C) KOW A3: logP = 5.3; A4: logP = 5.9 Henry <9.93 ´ 10-4 Pa m3 mol-1 (calc.) S.g./density A3: 1.1270; A4: 1.1265 (both 25 °C) Solubility A3: In water 0.88 ppm (20 °C). In methanol 64.8, ethanol 41.9, acetone 66.1, n-hexane 1.4, benzene 143.1, ethyl acetate 69.5 (all in g/l, 20 °C). A4: In water 7.2 ppm (20 °C). In methanol 458.8, ethanol 234.0, acetone 365.3, n-hexane 6.5, benzene 524.2, ethyl acetate 320.4 (all in g/l, 20 °C). Stability Unstable to alkali.
COMMERCIALISATION
History Introduced in Japan in 1990 by Sankyo Co., Ltd. Manufacturers Sankyo Agro
APPLICATIONS
Biochemistry GABA agonist. Acts on the peripheral nervous system by enhancing binding of GABA, resulting in increased chloride ion flow. Mode of action Contact and stomach action. Limited plant systemic activity but exhibits translaminar movement. Uses Control of Tetranychus urticae Koch on apples, aubergines, pears and strawberries; Tetranychus kanzawai Kishida on aubergines, pears, strawberries and tea; Panonychus citri McGregor on citrus fruit and pears; Panonychus ulmi Koch on apples; Aculops pelekassi Keifer on citrus fruit. Effective against all development stages. Applied at 5.6-28 g/ha. Also active against nematodes such as Bursaphelenchus xylophilus (pine wood nematode). Formulation types EC; WP. Selected products: 'Milbeknock' (Sankyo Agro); 'Ultiflora' (Gowan, Sankyo Agro)
OTHER PRODUCTS
'Koromite' (Sankyo Agro); 'Matsuguard' (pine wood nematode) (Sankyo Agro); 'Mesa' (Gowan, Sankyo Agro)
MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male mice 324, female mice 313, male rats 762, female rats 456 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rats >5000 mg/kg. Not a skin irritant. Inhalation LC50 (4 h) for male rats 1.90, female rats 2.80 mg/kg. NOEL for male rats 6.81, female rats 8.77, male mice 18.9, female mice 19.6 mg/kg daily. ADI 0.03 mg/kg (Japan). Other Not carcinogenic, not teratogenic, not mutagenic.
ECOTOXICOLOGY
Birds LD50 for male chickens 660, female chickens 650, male Japanese quail 1005, female Japanese quail 968 mg/kg. Fish LC50 (96 h) for rainbow trout 4.5, carp 17 mg/l. Daphnia LC50 (3 h) for D. pulex >100 ppm. Algae NOEL (72 h) ³7.3 mg/l. Bees LD50 (oral) 0.46 mg/bee; (contact) 0.025 mg/bee. Worms LC50 (14 d) for Eisenia foetida 61 ppm.
ENVIRONMENTAL FATE
Soil/Environment Soil DT50 16-33 d.
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