Abamectin

Abamectin

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Systematic (IUPAC) name
mixture of: (10E,14E,16E)-(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-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside and (10E,14E,16E)-(1R,4S,5′S,6S,6′R,8R,12S,13S,20R,21R,24S)-21,22-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-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
Clinical data
Legal status	ISO 1750 (approved)
Identifiers
CAS Number	71751-41-2 Y
ATCvet code	QP54AA02 (WHO)
ChemSpider	8095964 Y
UNII	5U8924T11H Y
KEGG	D02777 Y
ChEMBL	CHEMBL1630577 N
Synonyms	avermectin B1 (CAS name), MK-936
Chemical data
Formula	C48H72O14 (B1a) C47H70O14 (B1b)
InChI InChI=1S/C48H72O14.C47H70O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38;1-24(2)41-27(5)16-17-46(61-41)22-33-19-32(60-46)15-14-26(4)42(25(3)12-11-13-31-23-54-44-39(48)28(6)18-34(45(50)57-33)47(31,44)51)58-38-21-36(53-10)43(30(8)56-38)59-37-20-35(52-9)40(49)29(7)55-37/h12-15,17-19,25-26,28,30-31,33-45,49-50,52H,11,16,20-24H2,1-10H3;11-14,16-18,24-25,27,29-30,32-44,48-49,51H,15,19-23H2,1-10H3/b13-12+,27-15+,32-14+;12-11+,26-14+,31-13+/t25-,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47+,48+;25-,27-,29-,30-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42-,43-,44+,46+,47+/m00/s1 Y Key:IBSREHMXUMOFBB-JFUDTMANSA-N Y
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Abamectin is a widely used insecticide and anthelmintic.

Chemistry

Abamectin is a mixture of avermectins containing more than 80% avermectin B1a and less than 20% avermectin B1b. These two components, B1a and B1b have very similar biological and toxicological properties. The avermectins are insecticidal and antihelmintic compounds derived from various laboratory broths fermented by the soil bacterium Streptomyces avermitilis. Abamectin is a natural fermentation product of this bacterium.

Activity

Abamectin is an insecticide as well as an acaricide and a nematicide.

Use

Abamectin is used to control insect and mite pests of a range of agronomic, fruit, vegetable and ornamental crops, and it is used by homeowners for control of fire ants. Abamectin is also used as a veterinary antihelmintic. Resistance to abamectin-based antihelmintics, although a growing problem, is not as common as to other classes of veterinary antihelmintics. The benzoate salt emamectin benzoate is also used as an insecticide.

Trade names

Trade names include Abba, Abathor, Affirm, Agri-Mek, Avid, Dynamec, Epi-Mek, Genesis Horse Wormer, Reaper, Vertimec, CAM-MEK 1.8% EC (cam for agrochemicals), Zephyr and Cure 1.8 EC.

References

• "Pesticide Information Profile: Abamectin." Pesticide Management Education Program. May 1994. Cornell University Cooperative Extension. 18 Sep 2007.

External links

• Crop Protection Database: Learn more about abamectin