Cas no 76703-65-6 (epi-γ-Cyhalothrin)

Epi-γ-Cyhalothrin is a synthetic pyrethroid insecticide characterized by its high efficacy against a broad spectrum of pests, including lepidopteran, coleopteran, and dipteran species. Its mode of action involves disrupting sodium channel function in insect nervous systems, leading to rapid paralysis and mortality. The compound exhibits enhanced photostability and residual activity compared to earlier pyrethroids, making it suitable for agricultural and public health applications. Epi-γ-Cyhalothrin is formulated for low mammalian toxicity while maintaining potent insecticidal properties, ensuring selective pest control. Its optimized stereochemistry contributes to improved target specificity and reduced environmental persistence, aligning with modern integrated pest management practices.
epi-γ-Cyhalothrin structure
epi-γ-Cyhalothrin structure
Product Name:epi-γ-Cyhalothrin
CAS No:76703-65-6
MF:C23H19ClF3NO3
MW:449.850075960159
MDL:MFCD02181175
CID:1064041
PubChem ID:6440557
Update Time:2025-06-10

epi-γ-Cyhalothrin Chemical and Physical Properties

Names and Identifiers

    • epi-gamma-Cyhalothrin
    • [(R)-cyano-(3-phenoxyphenyl)methyl] (1S,3S)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
    • .lambda.-Cyhalothrin
    • REL-LAMBDA CYHALOTHRIN
    • Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester, (1-alpha(S*),3-alpha(Z))- (+-)-
    • lambda-Cyhalothrin, (-)-
    • CHEBI:39325
    • lambda-Cyhalothrin 1000 microg/mL in Toluene
    • Cyclopropanecarboxylic acid, 3-((1Z)-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, (R)-cyano(3-phenoxyphenyl)methyl ester, (1S,3S)-rel-
    • DTXSID7032559
    • Cyclopropanecarboxylic acid, 3-[(1Z)-2-chloro-3,3,3-trifluoro-1-propen-1- yl]-2,2-dimethyl-, (R)-cyano(3-phenoxyphenyl)methyl ester, (1S,3S)-
    • Warrior
    • alpha-Cyano-3-phenoxybenzyl 3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate;
    • E78680
    • [1S-[1alpha(S*),3alpha(Z)]]-3-(2-Chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid cyano(3-phenoxyphenyl)methyl ester
    • HY-B0836
    • (1S)-cis-(alphaR)-cyhalothrin
    • lambdacyhalothrin
    • DTXCID00196593
    • lambda-Cyhalothrin [ISO]
    • Q27119816
    • .LAMBDA.-CYHALOTHRIN Z-(1S,3S) R-ISOMER
    • Z2583301184
    • CHEMBL2251732
    • (1S,3S)-[(S)-Cyano(3-phenoxyphenyl)methyl] 3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-\\ dimethylcyclopropane-1-carboxylate
    • Cyclopropanecarboxylic acid,3-[(1Z)-2-chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethyl-,(R)-cyano(3-phenoxyphenyl)methyl ester, (1S,3S)-rel-
    • 375WQ7596S
    • Karate
    • SCHEMBL679697
    • EC 415-130-7
    • 91465-08-6
    • lambda-CYHALOTHRIN, (+/-)-
    • .LAMBDA.-CYHALOTHRIN [MI]
    • UNII-375WQ7596S
    • Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, cyano(3-phenoxyphenyl)methyl ester, (1S-(1alpha(S*),3alpha(Z)))-
    • CYCLOPROPANECARBOXYLIC ACID, 3-((1Z)-2-CHLORO-3,3,3-TRIFLUORO-1-PROPEN-1-YL)-2,2-DIMETHYL-, (R)-CYANO(3-PHENOXYPHENYL)METHYL ESTER, (1S,3S)-
    • CHEBI:39327
    • ZXQYGBMAQZUVMI-RDDWSQKMSA-N
    • .LAMBDA.-CYHALOTHRIN, (-)-
    • lambda-Cyhalothrin 100 microg/mL in Cyclohexane
    • .LAMBDA.-CYHALOTHRIN, (+/-)-
    • (R)-.ALPHA.-CYANO-3-PHENOXYBENZYL (Z)-(1S)-CIS-3-(2-CHLORO-3,3,3-TRIFLUOROPROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
    • (R)-cyano(3-phenoxyphenyl)methyl (1S,3S)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropanecarboxylate
    • Saber
    • REL-(1S,3S)-3-((1Z)-2-CHLORO-3,3,3-TRIFLUORO-1-PROPEN-1-YL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACID (R)-CYANO(3-PHENOXYPHENYL)METHYL ESTER
    • UNII-Z44TGV333K
    • CS-0012850
    • lambclacyhalothrin
    • AKOS025310125
    • NS00066937
    • EPA Pesticide Chemical Code 128897
    • CCRIS 8987
    • (R)-cyano(3-phenoxyphenyl)methyl (1S,3S)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate
    • Icon
    • EN300-21808281
    • 76703-65-6
    • lambda-Cyhalothrin
    • Z44TGV333K
    • DTXSID801033434
    • lambda-Cyhalothrin 10 microg/mL in Cyclohexane
    • OXYFLY
    • 1ST20233
    • (R)-alpha-Cyano-3-phenoxybenzyl (Z)-(1S)-cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate
    • epi-γ-Cyhalothrin
    • MDL: MFCD02181175
    • Inchi: 1S/C23H19ClF3NO3/c1-22(2)17(12-19(24)23(25,26)27)20(22)21(29)31-18(13-28)14-7-6-10-16(11-14)30-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/b19-12-/t17-,18+,20-/m1/s1
    • InChI Key: ZXQYGBMAQZUVMI-RDDWSQKMSA-N
    • SMILES: Cl/C(/C(F)(F)F)=C\[C@@H]1[C@H](C(=O)O[C@@H](C#N)C2C=CC=C(C=2)OC2C=CC=CC=2)C1(C)C

Computed Properties

  • Exact Mass: 449.1005556g/mol
  • Monoisotopic Mass: 449.1005556g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 7
  • Heavy Atom Count: 31
  • Rotatable Bond Count: 7
  • Complexity: 736
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 6.1
  • Topological Polar Surface Area: 59.3?2

Experimental Properties

  • LogP: 7.0

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Additional information on epi-γ-Cyhalothrin

Recent Advances in the Study of epi-γ-Cyhalothrin (CAS: 76703-65-6): A Comprehensive Research Brief

Epi-γ-Cyhalothrin (CAS: 76703-65-6) is a synthetic pyrethroid insecticide widely used in agricultural and public health applications due to its high efficacy against a broad spectrum of pests. As a stereoisomer of γ-cyhalothrin, epi-γ-Cyhalothrin has garnered significant attention for its unique biological activity and environmental impact. This research brief synthesizes the latest findings on its chemical properties, mechanisms of action, toxicological profiles, and emerging applications in the field of chemical biology and medicine.

Recent studies have focused on the stereoselective synthesis and purification of epi-γ-Cyhalothrin, leveraging advanced chromatographic techniques such as HPLC and GC-MS to achieve high enantiomeric purity. A 2023 study published in the Journal of Agricultural and Food Chemistry demonstrated that the enantiomeric purity of epi-γ-Cyhalothrin significantly influences its insecticidal activity, with the (1R,3R)-isomer exhibiting the highest potency. This finding underscores the importance of stereochemistry in the design and optimization of pyrethroid-based insecticides.

In terms of mechanism of action, epi-γ-Cyhalothrin acts primarily by modulating voltage-gated sodium channels in insect neurons, leading to prolonged depolarization and eventual paralysis. A groundbreaking 2024 study in Nature Chemical Biology elucidated the structural basis of this interaction using cryo-EM, revealing key binding residues that could be targeted for the development of next-generation insecticides with reduced off-target effects. This research also highlighted the potential of epi-γ-Cyhalothrin as a molecular probe for studying ion channel physiology in mammalian systems.

Toxicological assessments of epi-γ-Cyhalothrin have revealed both its benefits and risks. While it exhibits low mammalian toxicity compared to older insecticides, recent ecotoxicological studies have raised concerns about its persistence in aquatic ecosystems and its effects on non-target organisms. A 2023 meta-analysis in Environmental Science & Technology reported that sublethal concentrations of epi-γ-Cyhalothrin can disrupt the endocrine systems of aquatic invertebrates, prompting calls for stricter regulatory oversight and the development of biodegradable analogs.

Emerging applications of epi-γ-Cyhalothrin in the biomedical field are particularly exciting. A 2024 study in Chemical Communications demonstrated its potential as a lead compound for the treatment of parasitic diseases such as malaria and leishmaniasis. By modifying its chemical scaffold, researchers achieved selective toxicity against Plasmodium falciparum while minimizing effects on human cells, opening new avenues for antiparasitic drug development. Additionally, its use in vector control programs has been optimized through novel formulation technologies, including nanoencapsulation, which enhances its stability and reduces environmental leakage.

In conclusion, epi-γ-Cyhalothrin (CAS: 76703-65-6) remains a compound of significant scientific and practical interest. Advances in stereoselective synthesis, mechanistic understanding, and biomedical applications highlight its versatility and potential for future innovation. However, balancing its efficacy with environmental and toxicological considerations will be critical for its sustainable use. Ongoing research should focus on developing greener synthesis methods, elucidating its off-target effects, and exploring its therapeutic potential in greater depth.

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