S-Methoprene

Base Information

• Chemical Name: S-Methoprene
• CAS No.: 40596-69-8
• Molecular Formula: C19H34O3
• Molecular Weight: 310.477
• Hs Code.: 2918990090
• European Community (EC) Number: 613-834-0
• NSC Number: 758655
• UNII: 4YIQ0A94UR
• DSSTox Substance ID: DTXSID1035783
• Nikkaji Number: J344.494E
• Wikidata: Q27119791
• Metabolomics Workbench ID: 56208
• ChEMBL ID: CHEMBL1875086
• Mol file: 40596-69-8.mol

Synonyms:Altosid;Altosid PS 10;Altosid PS-10;Altosid PS10;Methoprene;ZR 515;ZR-515;ZR515

Chemical Property of S-Methoprene

Chemical Property:

• Vapor Pressure: 3.74E-06mmHg at 25°C
• Melting Point: 164oC
• Refractive Index: 1.462
• Boiling Point: 385.7 °C at 760 mmHg
• Flash Point: 162.4 °C
• PSA: 35.53000
• Density: 0.914 g/cm³
• LogP: 5.06200
• Storage Temp.: 0-6°C
• Water Solubility.: Miscible
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 310.25079494
• Heavy Atom Count: 22
• Complexity: 378

Purity/Quality:

99% ^*data from raw suppliers

Methoprene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, N
• Hazard Codes: Xi,N
• Statements: 36/37/38-51/53
• Safety Statements: 26-36-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)OC(=O)C=C(C)C=CCC(C)CCCC(C)(C)OC
• Isomeric SMILES: C[C@@H](CCCC(C)(C)OC)C/C=C/C(=C/C(=O)OC(C)C)/C
• Description: Methoprene is the common name for a racemic mixture of two enantiomers (R and S in a ratio of 1:1). The activity of the compound as a juvenile hormone (JH) mimic is restricted to the S enantiomer. Methoprene was the first insect growth regulator approved in the 1970s by the US Environmental Protection Agency after extensive studies showing low toxicity to vertebrates and rapid natural chemical degradation in the environment and through organism metabolism. Nowadays, it is one of the most widely used and successful insect growth regulators. Different products containing methoprene (e.g., pesticides, veterinary drugs) are commercially available in different forms (emulsifiable concentrates, granules, pellets, briquettes, aerosols, or sustained-release formulations). Some of these are applied to water for mosquito control whereas others are sprayed in areas where foods are stored to prevent insect infestations. Methoprene may be used in combination with other active insecticides to optimize pest control.
• Uses: Methoprene controls many insect pests (Diptera, Pharaoh’s ants, and also Coleoptera, Homoptera and Siphonaptera) in public health, stored commodities, food handling, processing and storage establishments, mushroom houses, on animals and on plants (including glasshouse plants). Methoprene is a broad-spectrum synthetic JH mimic, which acts as an insect growth regulator (insecticide). It prevents larval insect stages from undergoing metamorphosis to viable adults and thus acts as a larvicide. Methoprene is considered a biochemical pesticide because rather than controlling target pests through direct toxicity, methoprene interferes with the insect life cycle, preventing the insect from reaching maturity or reproducing. It is useful for control of a variety of insect pests including ants, mosquitoes, flies, fleas, beetles, lice, and moths, but is only effective against larvae, not adults or pupae. In order to control some of these insects, methoprene is used in the production of a number of foods including meat, milk, mushrooms, peanuts, rice, and cereals. Many different products (e.g., pesticides, veterinary drugs) and formulations containing methoprene are commercially available. Methoprene products used for protecting pets such as cats and dogs include capsules administered orally and flea collars used externally. Production animals (e.g., cattle) typically receive methoprene in the diet as a food additive. Other formulations of methoprene include emulsifiable concentrates, pellets and tablets, granules, and aerosols. Some of these are applied to water for mosquito control whereas others are sprayed in areas where foods are stored to prevent insect infestations. A potential therapeutic use of methoprene was proposed in the context of African sleeping sickness, since it was observed that this compound killed Trypanosoma brucei in culture. However, methoprene acid, resulting from the insecticide metabolism, exhibited no efficiency as trypanocide. Consistently, methoprene administered to infected mice showed to be unable to eliminate trypanosomes from the blood.

Technology Process of S-Methoprene

There total 41 articles about S-Methoprene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 20.0%

5-(6'-methoxy-2',6'-dimethylheptyl)-3-methyl-2,5-dihydrothiophene-2-carboxylic acid (87416-87-3) → Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate (52341-11-4) + methoprene (40596-69-8) + isopropyl 5-(6'-methoxy-2',6'-dimethylheptyl)-3-methylthiophene-2-carboxylate

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1007/BF00953165

Reference yield: 10.0%

(E)-4-Bromo-11-methoxy-3,7,11-trimethyl-dodec-2-enoic acid isopropyl ester → Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate (52341-11-4) + methoprene (40596-69-8) + isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate (41797-08-4,55290-71-6,58222-78-9,58223-32-8,68218-72-4)

Guidance literature:

With lithium carbonate; lithium bromide; In N,N-dimethyl-formamide; for 1h; Yield given. Title compound not separated from byproducts; Heating;

Reference yield:

diisopropyl ester of 2-methyl-3-isopropoxycarbonyl-2-propenylphosphonic acid (50798-35-1) + S-(-)-7-methoxy-3,7-dimethyloctanal (134678-53-8) → 2-cis-4-trans-S-methoprene (134678-54-9) + (2Z,4E)-(R)-11-Methoxy-3,7,11-trimethyl-dodeca-2,4-dienoic acid isopropyl ester (36557-27-4,40596-69-8,41205-06-5,52020-07-2,52341-11-4,53108-97-7,65733-16-6,65733-17-7,134678-54-9) + R-(-)-11-methoxy-3,7,11-trimethyl-2E,4E-dodecadienoic acid isopropyl ester (65733-17-7) + (S)-methoprene (65733-16-6)

Guidance literature:

With potassium hydroxide; In toluene; at 18 - 22 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1007/BF00958564

upstream raw materials:

Methoprene acid

isopropyl alcohol

7-methoxy-3,7-dimethyloctanal

diisopropyl ester of 2-methyl-3-isopropoxycarbonyl-2-propenylphosphonic acid

Refernces

• 1、 -. "Method for exterminating termites". . . Retrieved 2008/06/13.
• 2、 -. "Insecticidal combination to control mammal fleas, in particular fleas on cats and dogs". . . Retrieved 2008/06/13.