IVERMECTIN

PRODUCT IDENTIFICATION
CAS NO.

70288-86-7, 70161-11-4 (B1a), 70209-81-3 (B1b)

 

EINECS NO. 274-536-0, 274-384-5
FORMULA C48H74O13  (B1a), C47H72O15 (B1b)
MOL WT. 891.10 (B1a), 877.08 (B1b)

H.S. CODE

  

TOXICITY

  
SYNONYMS

22,23-Dihydroxy-avermectin B;

5-O-demethyl-22,23-dihydro- avermectin A; (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'-(perhydro pyran)-12-yl 2,6-dideoxy-4-O-(2,6- dideoxy-3-O-methyl-alpha- L-arabino hexopyranosyl)- 3-O-methyl-alpha-L-arabino hexopyranoside + (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-trioxa tetracyclo [15.6.1.14,8.020,24] pentacosa-10,14,16,22-tetraene)-6- spiro-2'-(perhydropyran)-12-yl 2,6-dideoxy -4-O-(2,6-dideoxy-3-O-methyl-alpha- L-arabino hexopyranosyl)-3-O-methyl- alpha-L-arabino  hexopyranoside;
DERIVATION

 

CLASSIFICATION

  

PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE white crystalline powder
MELTING POINT  
BOILING POINT  
SPECIFIC GRAVITY  
SOLUBILITY IN WATER  
pH  
VAPOR DENSITY

 

AUTOIGNITION

 

NFPA RATINGS

  

REFRACTIVE INDEX

  
FLASH POINT

 

STABILITY Stable under ordinary conditions.

GENERAL DESCRIPTION & APPLICATIONS
Avermectin: any of a group of pentacyclic sixteen-membered lactones derived from the soil bacterium Streptomyces avermitilis. Avermectins are insecticidal or anthelmintic compounds for domestic animals and sometimes humans. Abamectin is the mixture of individual avermectin B1a(more than 90%) and avermectin B1b (not more than 10%) components. A-series compounds are methoxylated at 5 position, whereas the B-series have an underivatized hydroxyl group at the position. The 1-subset compound has an olefinic bond between C22 and C23; the 2-subset possesses a hydroxyl group at position 23 due to the hydration of the double bonds. They are considered to have very similar biological activities and toxicological properties. Ivermectin is the most common avermectin. It is a broad spectrum antiparasitic drug for oral administration. It is sometimes used to treat human onchocerciasis. It is the mixture of 22,23-dihydro-avermectin B1a (at least 90%) and 22,23-dihydro-avermectin B1b (less than 10 %), differing by a single methylene group at 26 position. These are also known as 5-O-demethyl-22,23-dihydro-avermectin A1a and 5-O-demethyl-22,23-dihydro- avermectin A1b respectively. Ivermectin is a white to yellowish crystalline powder; nonhygroscopic; melting point 155 C; insoluble in water; soluble in methanol and ethanol. Doramectin has the closer structural similarity with abamectin than ivermectin. There is a different substituent at the 25 position without the dihydro modification at the 22,23 position. Doramectin is used as an endoparasitic agent in non-lactating cattle. Eprinomectin is the amino-avermectin derived from avermectin B1 with modified terminal oleandrose moiety. It is the mixture of 4"-epiacetylamino-4"-deoxy-avermectin B1a (> 90%) and B1b (< 10%).

Avermectin

Avermectin class acaricides or insecticides include:

  • Abamectin (CAS #: 71751-41-2)
    • Avermectin B1a (CAS #: 65195-55-3)
    • Avermectin B1b (CAS #: 65195-56-4)
  • Ivermectin (CAS #: 70288-86-7)
    • 22,23-Dihydroxy-avermectin B1a (CAS #: 70161-11-4)
    • 22,23-Dihydroxy-avermectin B1b (CAS #: 70209-81-3)
  • Doramectin (117704-25-3)
    • 25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)-avermectin A1a
  • Emamectin
    • (4"R)-4"-deoxy-4"-(methylamino)-avermectin B1a (CAS #: 119791-41-2)
    • (4"R)-4"-deoxy-4"-(methylamino)-avermectin B1b (CAS #: 137335-79-6)
  • Eprinomectin (CAS #: 123997-26-2)
    • 4"-Deoxy-4"-epiacetylamino-avermectin B1a (CAS#: 133305-88-1)
    • 4"-Deoxy-4"-epiacetylamino-avermectin B1b (CAS #: 133305-89-2)
  • Selamectin (CAS #: 165108-07-6)
    • (5Z,25S)-25-Cyclohexyl-4'-O-de(2,6-dideoxy-3-O-methyl-alpha-L-arabino- hexopyranosyl)-5-demethoxy- 25-de(1-methylpropyl)-22,23-dihydro- 5-(hydroxyimino)-avermectin A1a
SALES SPECIFICATION

APPEARANCE

 white to off-white crystalline powder

IDENTIFICATION

Complies

ASSAY

B1a + B1b : 95.0% min (B1a : 90.0% min)

OPTICAL ROTATION

-17° ~ -20°

RELATED SUBSTANCE

5.0% max

ETHANOL

5.0% max

FORMAMIDE

3.0% max

RESIDUE ON IGNITION

0.1% max
HEAVY METALS

20ppm max

LOSS ON DRYING

1.0% max
TRANSPORTATION
PACKING

 

HAZARD CLASS  
UN NO.  
AVERMECTIN PRODUCTS

Product

CAS RN
(23S)-25-De(1-methylpropyl)-22,23-dihydro-23-hydroxy-25- (1-methylethyl) avermectin A1a 65195-54-2
(23S)-22,23-Dihydro-23-hydroxyavermectin A1a 65195-53-1
22,23-Dihydroavermectin B1a 71827-03-7
25-De(1-methylpropyl)-25-(1-methylethyl)avermectin A1a 65195-52-0
27-Hydroxyavermectin 109084-58-4
4''-Epiacetylamino-4''-deoxyavermectin B1 160902-72-7
5-O-Demethylavermectin A1a 65195-55-3
Abamectin 71751-41-2
Avermectin 73989-17-0
Avermectin A1 71751-39-8
Avermectin A1a 65195-51-9
(4''R)- 22,23-Dihydro-4''-(acetylamino)-5-O-demethyl-4''-deoxy-26- ((2-methoxyethoxy) methoxy)avermectin A1a 148865-44-5
(13R,23S)- 22,23-dihydro-5-O-demethyl-23-hydroxyavermectin A1a 135680-93-2
22,23-Dihydro-5-O-demethyl-26-((2-methoxyethoxy)methoxy) avermectin A1a 156153-56-9
(8Z)-3'',5-di-O-demethylavermectin A1a 123237-30-9
(4''R)-4''-(Acetylamino)-26-(benzoyloxy)-5-O-demethyl-4''-deoxyavermectin A1a 148864-94-2
(4''R)-4''-(Acetylamino)-5-O-demethyl-4''-deoxy-26-((2-methoxyethoxy) methoxy) avermectin A1a 148865-00-3
(4''R)-4''-(Acetylamino)-5-O-demethyl-4''-deoxy-26-methoxyavermectin A1a 156153-52-5
(13R)-5-O-Demethylavermectin A1a hydrate 135681-09-3
5-O-Demethyl-26-hydroxyavermectin A1a 86629-72-3
5-O-Demethyl-26-hydroxy-4''-O-((2-methoxyethoxy)methyl)avermectin A1a 148865-08-1
5-O-Demethyl-25-de(1-methylpropyl)-25-(1-methylethyl)avermectin A1a 65195-56-4
(23S)-5-O-Demethyl-25-de(1-methylpropyl)-22,23-dihydro-23-hydroxy- 25-(1-methylethyl) avermectin A1a 65195-58-6
(4''R)-4''-Deoxy-4''-(methylamino)avermectin B1 119791-41-2; 137335-79-6
Avermectin B2 71751-42-3
Avermectin B2a 65195-57-5
Doramectin 117704-25-3
Emamectin benzoate 137512-74-4; 155569-91-8
Eprinomectin B1a 133305-88-1
Eprinomectin B1b 133305-89-2
Eprinomectin 123997-26-2
Ivermectin B1a 70161-11-4
Ivermectin B1b 70209-81-3
Ivermectin luminol 122047-12-5
Ivermectin 70288-86-7
Selamectin 220119-17-5; 165108-07-6