Abamectin

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Abamectin
Category Agricultural
Catalog number BBF-05730
CAS 71751-41-2
Molecular Weight 1732.14
Molecular Formula C48H72O14.C47H70O14
Purity >95% a mixture of B1a and B1b

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Description

Avermectin B1 (Abamectin) is a widely used insecticide and anthelmintic. It is a mixture of avermectins containing more than 80% avermectin B1a and less than 20% avermectin B1b, which have very similar biological and toxicological properties. Avermectin B1 is a natural fermentation product of this bacterium.

Specification

Related CAS 65195-55-3 (Avermectin B1a) 65195-56-4 (Avermectin B1b) 86753-29-9 100920-72-7 122666-97-1 138794-43-1 181658-85-5 1047643-53-7
Synonyms Avomec; Agri-Mek; Avid; Agrimek; Vertimec; Affirm; Zephyr; MK 936; MK 0936; NSC 758202; Avermectin B1; MK-936; Spiro[11,15-methano-2H,13H,17H-furo[4,3,2-pq][2,6]benzodioxacyclooctadecin-13,2'-[2H]pyran], avermectin B1 deriv.; A 14906; A 8612; Abamektin; Abamitel; Abarex; Abastate; Abastate EW; Abathor; Abba; Agador; AgMectin; Agri-Mek; Agri-Mek SC; Agrimec; Avermectin B1a-Avermectin B1b mixt.; Aversectin S; Avert; Avicta; Avicta 400FS; Avid 0.15EC; CHA 2061; CHA 2062; Dalamectin; Dalamektin; Epi-Mek; Fitoverm; Fitoverm M; Genesis Oral Drench; Genesis Pour-on for Cattle and Deer; Kraft; KRAFT 36 EC; L 676; Lirosect; Lyrosekt; Mectin; Phytoverm; PT 310; Rustomectin; STAN; Temprano; Vermitec; Vertigo (pesticide); Vertigo 018EC; Vertimec 018SC; Zoro
Shelf Life Limited shelf life, expiry date on the label
Storage Store at -20°C
IUPAC Name (1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-21',24'-dihydroxy-12'-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethyl-2-propan-2-ylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one;(1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-2-[(2S)-butan-2-yl]-21',24'-dihydroxy-12'-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one
Canonical SMILES CCC(C)C1C(C=CC2(O1)CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC)OC)C)C.CC1C=CC=C2COC3C2(C(C=C(C3O)C)C(=O)OC4CC(CC=C(C1OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)O)OC)OC)C)OC7(C4)C=CC(C(O7)C(C)C)C)O
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
InChI Key IBSREHMXUMOFBB-MVGRHBATSA-N

Properties

Appearance White or Light Yellow Crystal Powder
Antibiotic Activity Spectrum Parasites
Boiling Point 940.9±65.0 °C at 760 mmHg
Melting Point 155-160°C
Density 1.16 g/cm3
Solubility Soluble in Chloroform (Sparingly, Sonicated), DMSO (Slightly), Ethyl Acetate (Slightly)

Toxicity

Toxicity Rat: Oral LD50 300 mg/kg.
Rabbit: Dermal LD50 >1800 mg/kg.
Moderate eye irritation, very slight primary skin irritation

Reference Reading

1.Suspected levamisole intoxication in calves.
Müller KR1, Dwyer C1. N Z Vet J. 2016 Mar 3:1-4. [Epub ahead of print]
CASE HISTORY: A group of 32 Friesian and four Hereford calves, 3-4 months old with body weights between 100-120 kg, were purchased from a weaner sale. On arrival at the property the Hereford calves were treated with a combination anthelmintic containing 2 g/L abamectin and 80 g/L levamisole hydrochloride. Shortly afterwards they developed tremors and frothing from the mouth, and two died overnight. The Friesian calves were treated with the same anthelmintic on the following day, when some showed hypersalivation and frothing from the mouth.
2.Analysis of the relationship between P-glycoprotein and abamectin resistance in Tetranychus cinnabarinus (Boisduval).
Xu Z1, Shi L1, Peng J1, Shen G1, Wei P1, Wu Q1, He L2. Pestic Biochem Physiol. 2016 May;129:75-82. doi: 10.1016/j.pestbp.2015.10.021. Epub 2015 Oct 31.
Abamectin is an effective acaricide and widely used in the control of Tetranychus cinnabarinus. With the increase of control failures, it is however important to clarify the resistance mechanism to improve the control of this mite. P-glycoprotein (Pgp) is an ATP-dependent drug efflux pump for xenobiotic compounds and is involved in multidrug resistance. In this study, the results showed that verapamil, the specific inhibitor of Pgp, could enhance the lethal effect of abamectin on mites, and this effect is more enhanced in abamectin-resistant strain (AbR, mortality increased 74.51%) than that in susceptible strain (SS, 19.91%). Further analysis showed that the activity of Pgp ATPase in AbR was significantly higher (1.65-fold) than that in SS. After exposure to sublethal concentration of abamectin, the ATPase activity in AbR was significantly increased 1.43-fold to that in control; but there was no significant difference in SS after treatment.
3.Abamectin in soils: Analytical methods, kinetics, sorption and dissipation.
Dionisio AC1, Rath S2. Chemosphere. 2016 May;151:17-29. doi: 10.1016/j.chemosphere.2016.02.058. Epub 2016 Mar 15.
Abamectin is a broad-spectrum antiparasitic agent that has been widely employed in veterinary medicine and has also been used as a pesticide in agriculture. Veterinary drugs may reach the soil and may be transported to surface and ground waters, posing risks to terrestrial and aquatic organisms. Sorption, transformation and transport processes are primarily responsible for the fate of these substances in the environment. In this study, the sorption and the aerobic dissipation of abamectin in Brazilian soils (sand, clay and sandy-clay) were evaluated. For sorption studies, batch equilibrium experiments were performed. Sorption and desorption isotherms were fitted to the Freundlich model. Abamectin showed a high affinity to soil particles, with Freundlich sorption and desorption coefficients ranging from 44 to 138 μg(1-1/n) (cm(3))(1/n) g(-1) and from 89 to 236 μg(1-1/n) (cm(3))(1/n) g(-1), respectively. Dissipation of abamectin was evaluated in sterile and non-sterile soils in an aerobic and dark environment under controlled temperature and humidity.
4.Estimated crop loss due to coconut mite and financial analysis of controlling the pest using the acaricide abamectin.
Rezende D1, Melo JW2, Oliveira JE3, Gondim MG Jr1. Exp Appl Acarol. 2016 Apr 8. [Epub ahead of print]
Reducing the losses caused by Aceria guerreronis Keifer has been an arduous task for farmers. However, there are no detailed studies on losses that simultaneously analyse correlated parameters, and very few studies that address the economic viability of chemical control, the main strategy for managing this pest. In this study the objectives were (1) to estimate the crop loss due to coconut mite and (2) to perform a financial analysis of acaricide application to control the pest. For this, the following parameters were evaluated: number and weight of fruits, liquid albumen volume, and market destination of plants with and without monthly abamectin spraying (three harvests). The costs involved in the chemical control of A. guerreronis were also quantified. Higher A. guerreronis incidence on plants resulted in a 60 % decrease in the mean number of fruits harvested per bunch and a 28 % decrease in liquid albumen volume. Mean fruit weight remained unaffected.

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