Cyhalothrin information

Lambda-cyhalothrin
	; λ-cyhalothrin (racemic)
Names
	IUPAC name (R)-α-cyano-3-phenoxybenzyl (1S)-cis-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate and (S)-a-cyano-3-phenoxybenzyl (1R)-cis-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate
	Other names Cyhalothrine
Identifiers
	Compounds; Lambda: λ-Cyhalothrin; (RS)-α-cyano (1RS,3RS): Cyhalothrin; Gamma: γ-Cyhalothrin;
CAS Number	Lambda: 91465-08-6 ; (RS)-α-cyano (1RS,3RS): 68085-85-8 ; Gamma: 76703-62-3 ;
3D model (JSmol)	Gamma: Interactive image;
ChEBI	Gamma: CHEBI:39323;
ChEMBL	Gamma: ChEMBL2270530;
ChemSpider	Lambda: 9680967 ; Gamma: 4944812 ;
ECHA InfoCard	100.062.209
EC Number	(RS)-α-cyano (1RS,3RS): 268-450-2; Gamma: 616-373-3;
PubChem CID	Lambda: 71464055; (RS)-α-cyano (1RS,3RS): 5281873; Gamma: 6440554;
RTECS number	Lambda: GZ1227780;
UNII	Lambda: Z44TGV333K ; (RS)-α-cyano (1RS,3RS): V0V73PEB8M ; Gamma: GOI9BD654Y ;
UN number	2588
CompTox Dashboard (EPA)	Lambda: DTXSID6023997 ;
	InChI Lambda: InChI=1S/2C23H19ClF3NO3/c21-22(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/h23-12,17-18,20H,1-2H3/b219-12-/t217-,18+,20-/m10/s1 Key: BFPGVJIMBRLFIR-GUCBCRIZSA-N; (RS)-α-cyano (1RS,3RS): InChI=1S/4C23H19ClF3NO3/c41-22(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/h43-12,17-18,20H,1-2H3/b419-12-/t217-,18+,20-;2*17-,18-,20-/m1010/s1 Key: OOAOVGPMANECPJ-RWEUCVCFSA-N; Gamma: 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-/m0/s1 Key: ZXQYGBMAQZUVMI-GCMPRSNUSA-N; Key: ZXQYGBMAQZUVMI-UHFFFAOYSA-N;
	SMILES Gamma: CC1([C@H]([C@H]1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)/C=C(/C(F)(F)F)\Cl)C;
Properties
Chemical formula	C23H19ClF3NO3
Molar mass	449.85 g·mol−1
Appearance	Colourless solid
Density	1.33 g/cm3
Melting point	49.2 °C (120.6 °F; 322.3 K)
Boiling point	Decomposes before boiling
Solubility in water	0.005 mg/L [20 °C]
Solubility in other solvents	Very soluble in hexane, toluene, methanol, acetone
log P	5.5
Acidity (pKa)	Not applicable
Pharmacology
ATCvet code	QP53AC06 (WHO)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H312, H330, H410
Precautionary statements	P260, P264, P270, P271, P273, P280, P284, P301+P310, P302+P352, P304+P340, P310, P312, P320, P321, P322, P330, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)	3 1 1
Flash point	225 °C (437 °F; 498 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyhalothrin is the ISO common name^[3] for an organic compound that, in specific isomeric forms, is used as a pesticide.^[4] It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as cyhalothrin are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.^[5]

^ Pesticide Properties Database. "lambda-Cyhalothrin". University of Hertfordshire.
^ "[(R)-Cyano-(3-phenoxyphenyl)methyl] 3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate". Retrieved 2020-02-02.
^ "Compendium of Pesticide Common Names". BCPC.
^ Pesticide Properties Database. "Cyhalothrin". University of Hertfordshire.
^ Metcalf, Robert L.; Horowitz, Abraham R. (2014). "Insect Control, 1. Fundamentals". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a14_263.

[PPDBlambda-1] Pesticide Properties Database. "lambda-Cyhalothrin". University of Hertfordshire.

[pubchem-2] "[(R)-Cyano-(3-phenoxyphenyl)methyl] 3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate". Retrieved 2020-02-02.

[3] "Compendium of Pesticide Common Names". BCPC.

[4] Pesticide Properties Database. "Cyhalothrin". University of Hertfordshire.

[Ullmann-5] Metcalf, Robert L.; Horowitz, Abraham R. (2014). "Insect Control, 1. Fundamentals". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a14_263.

Cyhalothrin information

and 30 Related for: Cyhalothrin information

Cyhalothrin

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Glossary of chemical formulae

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Environmental impact of pesticides

Names
λ-cyhalothrin (racemic)
IUPAC name (R)-α-cyano-3-phenoxybenzyl (1S)-cis-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate and (S)-a-cyano-3-phenoxybenzyl (1R)-cis-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate
Other names Cyhalothrine
Identifiers
Compounds Lambda: λ-Cyhalothrin (RS)-α-cyano (1RS,3RS): Cyhalothrin Gamma: γ-Cyhalothrin
CAS Number	Lambda: 91465-08-6^Y (RS)-α-cyano (1RS,3RS): 68085-85-8^Y Gamma: 76703-62-3^Y
3D model (JSmol)	Gamma: Interactive image
ChEBI	Gamma: CHEBI:39323
ChEMBL	Gamma: ChEMBL2270530
ChemSpider	Lambda: 9680967^Y Gamma: 4944812^Y
ECHA InfoCard	100.062.209
EC Number	(RS)-α-cyano (1RS,3RS): 268-450-2 Gamma: 616-373-3
PubChem CID	Lambda: 71464055 (RS)-α-cyano (1RS,3RS): 5281873 Gamma: 6440554
RTECS number	Lambda: GZ1227780
UNII	Lambda: Z44TGV333K^Y (RS)-α-cyano (1RS,3RS): V0V73PEB8M^Y Gamma: GOI9BD654Y^Y
UN number	2588
CompTox Dashboard (EPA)	Lambda: DTXSID6023997
InChI Lambda: InChI=1S/2C23H19ClF3NO3/c21-22(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/h23-12,17-18,20H,1-2H3/b219-12-/t217-,18+,20-/m10/s1 Key: BFPGVJIMBRLFIR-GUCBCRIZSA-N (RS)-α-cyano (1RS,3RS): InChI=1S/4C23H19ClF3NO3/c41-22(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/h43-12,17-18,20H,1-2H3/b419-12-/t217-,18+,20-;2*17-,18-,20-/m1010/s1 Key: OOAOVGPMANECPJ-RWEUCVCFSA-N Gamma: 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-/m0/s1 Key: ZXQYGBMAQZUVMI-GCMPRSNUSA-N Key: ZXQYGBMAQZUVMI-UHFFFAOYSA-N
SMILES Gamma: CC1([C@H]([C@H]1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)/C=C(/C(F)(F)F)\Cl)C
Properties^[1]
Chemical formula	C₂₃H₁₉ClF₃NO₃
Molar mass	449.85 g·mol⁻¹
Appearance	Colourless solid
Density	1.33 g/cm³
Melting point	49.2 °C (120.6 °F; 322.3 K)
Boiling point	Decomposes before boiling
Solubility in water	0.005 mg/L [20 °C]
Solubility in other solvents	Very soluble in hexane, toluene, methanol, acetone
log P	5.5
Acidity (pK_a)	Not applicable
Pharmacology
ATCvet code	QP53AC06 (WHO)
Hazards^[2]
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H312, H330, H410
Precautionary statements	P260, P264, P270, P271, P273, P280, P284, P301+P310, P302+P352, P304+P340, P310, P312, P320, P321, P322, P330, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)	3 1 1
Flash point	225 °C (437 °F; 498 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references