(S)-(-)-Chlocyphos
[CAS# 98674-86-3]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: (S)-(-)-Chlocyphos
• Synonyms: (S)-(-)-4-(2-Chlorophenyl)-2-hydroxy-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide
• Molecular Formula: C₁₁H₁₄ClO₄P
• Molecular Weight: 276.65
• CAS Registry Number: 98674-86-3
• EC Number: 623-314-5
• SMILES: CC1(COP(=O)(O[C@@H]1C2=CC=CC=C2Cl)O)C

Properties

• Melting point: 228-234 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

(S)-(-)-Chlocyphos is an organophosphorus compound that has garnered attention in the field of agricultural chemistry due to its effectiveness as an insecticide. This chiral molecule is known for its specific enantiomeric form, which plays a crucial role in its biological activity.

The discovery of (S)-(-)-Chlocyphos can be traced back to the search for potent and selective pesticides that can effectively control insect populations while minimizing environmental impact and toxicity to non-target species. Researchers in the mid-20th century began exploring the potential of organophosphorus compounds, which inhibit acetylcholinesterase, an enzyme crucial for nerve function in insects. This inhibition leads to the accumulation of acetylcholine, causing paralysis and death in pests.

(S)-(-)-Chlocyphos, being an organophosphate, functions by this mechanism but stands out due to its chiral nature. The (S)-enantiomer of Chlocyphos has been found to be significantly more effective than its (R)-enantiomer, which highlights the importance of chirality in the design and application of insecticides. The enhanced effectiveness of the (S)-enantiomer means that lower doses can be used to achieve the desired pest control, thereby reducing the overall chemical load in the environment.

One of the primary applications of (S)-(-)-Chlocyphos is in agricultural pest management. It is used to protect crops from a wide range of insect pests, thereby ensuring higher yields and better quality produce. Its application extends to various crops, including cereals, vegetables, and fruits, making it a versatile tool for farmers. The use of (S)-(-)-Chlocyphos helps in reducing crop damage and preventing the spread of plant diseases carried by insects.

In addition to its use in agriculture, (S)-(-)-Chlocyphos has applications in public health. It is employed in controlling vector-borne diseases by targeting insect vectors such as mosquitoes, which are responsible for spreading diseases like malaria and dengue fever. The effective control of these vectors helps in reducing the incidence of such diseases, thereby protecting public health.

The safety and environmental profile of (S)-(-)-Chlocyphos have been the subject of extensive study. While effective as an insecticide, its use must be carefully managed to avoid potential negative impacts on non-target organisms, including beneficial insects, wildlife, and humans. Regulatory bodies have established guidelines and restrictions to ensure that (S)-(-)-Chlocyphos is used in a manner that minimizes risks while maximizing benefits.

Overall, (S)-(-)-Chlocyphos represents an important advancement in the field of insecticide development. Its discovery and application underscore the significance of chirality in chemical compounds and its impact on biological activity. As research continues, there is potential for developing even more selective and environmentally friendly pest control agents based on the principles demonstrated by (S)-(-)-Chlocyphos.

References

none