EPRINOMECTIN (AMINOAVERMECTIN)

EPRINOMECTIN

PRODUCT IDENTIFICATION

CAS NO.

123997-26-2, 133305-88-1 (B_1a), 133305-89-2 (B_1b)

EINECS NO.

FORMULA C₅₀H₇₅NO₁₄ (B_1a), C₄₉H₇₃NO₁₄(B_1b)

MOL WT. 914, 900

H.S. CODE

TOXICITY

SYNONYMS Aminoavermectin;

Component B_1a: (4"R)-4"-(Acetylamino)-5-0-demethyl-4"-deoxyavermectin A_1a; 4"-Epiacetamido-4"-deoxyavermectin B_1a; (2aE,4E,5'S,6S,6'R,7S,8E,11R,13S,15S,17aR,20aR,20bS)- 6'-(S)-sec-Butyl-5',6,6',7,10,11,14,15,17a,20,20a,20b-dodecahydro-20,20b-dihydroxy- 5',6,8,19-tetramethyl-17-oxospiro [11,15-methano-2H,13H,17H-furo [4,3,2-pq] [2,6]benzo dioxacyclooctadecin -13,2'-[2H]pyran]-7-yl 4-O-(4-acetamido-2,4,6-trideoxy- 3-O-methyl-alpha- L-lyxo-hexopyranosyl)-2,6-dideoxy-3-O-methyl- alpha-L-arabino- hexopyranoside; Component B_1b: (4"R)-4"-(Acetylamino)-5-0-demethyl-25-de(1-methylpropyl)-4"-deoxy- 25-(1-methylethyl) avermectin A_1a; 4"-Epiacetylamino-4"-deoxyavermectin B_1b; 4"-Epiacetamido-4"-deoxyavermectin B_1b; (2aE,4E,5'S,6S,6'R,7S,8E,11R,13S,15S,17aR,20aR,20bS)- 5',6,6',7,10,11,14,15,17a,20,20a,20b- Dodecahydro-20,20b-dihydroxy-6'-isopropyl-5',6,8,19- tetramethyl- 17-oxospiro[11,15-methano-2H,13H,17H-furo [4,3,2-pq][2,6]benzo dioxacyclooctadecin-13,2'-[2H]pyran]-7-yl 4-O-(4-acetamido-2,4,6-trideoxy-3-O-methyl-alpha- L-lyxo-hexopyranosyl)-2,6-dideoxy-3-O-methyl- alpha-L-arabino-hexopyranoside

SMILES

CLASSIFICATION

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white crystalline powder

MELTING POINT 163 - 166 C

BOILING POINT

SPECIFIC GRAVITY 1.23

SOLUBILITY IN WATER

pH 7 - 8

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 B_1a(more than 90%) and avermectin B_1b (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 B_1a (at least 90%) and 22,23-dihydro-avermectin B_1b (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 A_1b 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 B_1a (> 90%) and B_1b (< 10%).

Avermectin

Avermectin class acaricides or insecticides include:

Abamectin (CAS #: 71751-41-2)

Avermectin B_1a (CAS #: 65195-55-3)
Avermectin B_1b (CAS #: 65195-56-4)

Ivermectin (CAS #: 70288-86-7)

22,23-Dihydroxy-avermectin B_1a (CAS #: 70161-11-4)
22,23-Dihydroxy-avermectin B_1b (CAS #: 70209-81-3)

Doramectin (117704-25-3)

25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)-avermectin A_1a

Emamectin

(4"R)-4"-deoxy-4"-(methylamino)-avermectin B_1a (CAS #: 119791-41-2)
(4"R)-4"-deoxy-4"-(methylamino)-avermectin B_1b (CAS #: 137335-79-6)

Eprinomectin (CAS #: 123997-26-2)

4"-Deoxy-4"-epiacetylamino-avermectin B_1a (CAS#: 133305-88-1)
4"-Deoxy-4"-epiacetylamino-avermectin B_1b (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 A_1a

SALES SPECIFICATION

APPEARANCE

white to off-white crystalline powder

IDENTIFICATION

Complies

ASSAY

B_1a+ B_1b: 90.0% min (B_1a: 88.0% min)

HEAVY METALS

10ppm max

WATER

5.0% max

TRANSPORTATION

PACKING

HAZARD CLASS 6.1 (Packing Group: II)

UN NO. 2811

OTHER INFORMATION

Hazard Symbols: XN, Risk Phrases: 25-48, Safety Phrases: 50

AVERMECTIN PRODUCTS

PRICE INFORMATION