68085-85-8

Basic information

• Product Name: Cyhalothrin
• Synonyms: cyano-3-phenoxybenzyl (1s+1r)-cis-3-(z-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylate;cyano(3-phenoxyphenyl)methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate;3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid cyano(3-phenoxyphenyl) methyl ester;(rs)-alpha-cyano-3-phenoxybenzyl(z)-(1rs)-cis-3-(2-chloro-3,3,3-trifluoroprope;(rs)-alpha-cyano-3-phenoxybenzyl(z)-(1rs,3rs)-(2-chloro-3,3,3-trifluoropropen;[1alpha,3alpha(z)]-(+-)-cyano-(3-phenoxyphenyl)methyl3-(2-chloro-3,3,3-triflu;3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylicacid;cyan(3-phenoxyphenyl)methylester.
• CAS NO: 68085-85-8
• Molecular Formula: C₂₃H₁₉ClF₃NO₃
• Molecular Weight: 449.85
• EINECS: 268-450-2
• Product Categories: AcaricidesPesticides&Metabolites;Alpha sort;C;CAlphabetic;CO - CZMethod Specific;Insecticides;Oeko-Tex Standard 100;Pesticides;Pesticides&Metabolites;PesticidesPesticides;Pyrethroids
• Mol File: 68085-85-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: <10 °C
• Boiling Point: 498.9 ºC at 760 mmHg
• Flash Point: 2 °C
• Appearance: Colorless solid
• Density: 1.344 g/cm³
• Vapor Pressure: 1×10-6pa 20°C
• Storage Temp.: 2-8°C
• Water Solubility: 0.004 mg l-1 (20 °C)
• CAS DataBase Reference: Cyhalothrin(CAS DataBase Reference)
• NIST Chemistry Reference: Cyhalothrin(68085-85-8)
• EPA Substance Registry System: Cyhalothrin(68085-85-8)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36-52/53
• Safety Statements: 26-36/37-61-16
• RIDADR: 2902
• WGK Germany: 2
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 68085-85-8(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Cyhalothrin is used as an insecticide and acaricide for the control of a variety of insect pests in various crops. It is particularly effective against pests such as the Colorado beetle in potatoes, cereals, hops, vegetables, cotton, and other crops.
Used in Animal Health:
Cyhalothrin is also used mainly for ectoparasite control on animals, helping to protect them from harmful insects and mites.
Used in Public Health:
Lambda-cyhalothrin, a form of Cyhalothrin, has public health applications and is utilized for the control of insect-borne diseases by targeting the insects that transmit them.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Cyhalothrin is a trifluoromethyl pyrethrine derivative.

Metabolic pathway

Cyhalothrin is similar in structure to cypermethrin but with one of the chlorine atoms replaced by a trifluoromethyl group. This substitution appears to result in greater lipophilicity. Cyhalothrin is used in animal health and the more active isomer mixture, lambda-cyhalothrin, has the main crop use. Only a limited amount of information has been published in the scientific literature. What is available indicates that the metabolism and environmental fate of the cyhalothrins are very similar to those of cypermethrin. Both compounds have been the subject of UK Pesticide Safety Directorate evaluations (referred to as PSD in parentheses below).

Degradation

Cyhalothrin is stable to decomposition and to cis-trans isomerisation for at least 4 years in the dark. It is a photostable pyrethroid. It is hydrolysed at high pH to afford the acid (2) and the cyanohydrin (3) which decomposes to 3-phenoxybenzaldehyde (4,3PBAl).

Upstream product

• 393870-46-7 3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarbonyl chloride 
• 39515-47-4 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile 
• 82561-08-8 N-(α-cyano-3-phenoxybenzyl)-N,N,N-trimethylammonium methylsulfate 
• 108-10-1 4-methyl-2-pentanone 
• 111-51-3 N,N,N',N'-tetramethyl-1,4-butanediamine 
• 39515-51-0 3-Phenoxybenzaldehyde 
• 773837-37-9 sodium cyanide 
• 78246-90-9 cyhalothrin chloride 

Downstream Products

• 74609-46-4 3-(2-chloro-3,3,3-trifluoroprop-1-en-yl)-2,2-dimethylcyclopropanecarboxylic acid 
• 39515-47-4 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile 

Relevant articles and documents

Preparation method of cyanogen chrysanthemum ester insecticide

The invention discloses a preparation method of a Clocythrin pesticide. The method comprises the following steps: a) mixing chrysanthemic acid and chrysanthemyl chloride and placing the mixture into a reaction vessel, adding triethylamine and introducing phosgene, slowly heating to 55-110 DEG C and fully reacting for 1-4 h so as to generate Chrysanthemoyl chloride; and b) dissolving sodium cyanide in an aqueous-phase Triton micellar solution, adding a catalyst and heating to 40 DEG C, slowly and dropwise adding mixed liquor of Chrysanthemoyl chloride and m-Phenoxybenzaldehyde, keeping the temperature and reacting for 1-4 h, cooling to 10 DEG C, adding a few amount of water and crystal seed, fully stirring and precipitating solids, and washing the precipitated solids with alkali, washing, filtering and drying so as to obtain a final product Clocythrin. The solvent in the invention can be recycled, use of the catalyst and water is reduced, and discharge of toxic wastewater and exhaust gas is minimized. The post-processing procedure is simple, and extraction and solvent distillation are not required. The final product can be obtained through simple centrifugation, washing and filtration. Discharge of solid wastes is decreased.

AGRICULTURAL CHEMICALS

The present invention relates to derivatives of compounds which are known to be of use in the field of agriculture. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more changes one or more of which may be considered to represent a change of oxidation state relative to the groups in the original compound. We refer to these compounds generally as redox derivatives. The compounds are of use as insecticides, herbicides and insect repellents.

AGRICULTURAL CHEMICALS

The present invention relates to derivatives of compounds which are known to be of use in the field of agriculture. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more changes one or more of which may be considered to represent a change of oxidation state relative to the groups in the original compound. We refer to these compounds generally as redox derivatives. The compounds are of use as insecticides, herbicides and insect repellents.

Process for the preparation of pyrethroid type ester compounds

The present invention relates to a novel process for the preparation of insecticidally active esters of the general formula (I) STR1 wherein R1 and R2 are the same or diferent from each other and represent a hydrogen or a halogen atom; R3 represents STR2 (wherein R4 and R5 represent a chlorine or bromine atom or a methyl group when R4 is identical to R5, but R4 represents a chlorine or bromine atom or a methyl group and R5 represents a trifluoromethyl group when R4 is different from R5, and R6 represents a halogen atom or a difluoromethoxy group); and R8 represents a hydrogen or a cyano group. The characteristic of the present invention is a one-step procedure comprising directly condensing an organic acid, an aldehyde (and a water-soluble cyanide) in the presence of a phase transfer catalyst and a water-soluble inorganic base by the use of a sulphonyl compound as a condensing reagent.

Cyanophenoxybenzyl amines

The invention concerns novel compounds of the formula I STR1 wherein A, B, D and E are chosen from hydrogen, halogen, C1 to C6 alkyl, C1 to C6 haloalkyl and C1 to C6 alkoxy and Z is a tertiary or quaternary amino group. The compounds are useful intermediates for the preparation of pyrethroids. In further embodiments the invention provides processes for the preparation of the compounds of formula I and processes for the synthesis of pyrethroids utilizing the compounds of formula I.

Preparation of esters

Certain alpha-cyano esters are prepared by reacting an acyl halide with an aldehyde in a substantially water-immiscible aprotic solvent and an aqueous solution of water-soluble cyanide salt in the presence of an amine or cryptate rate-promoting agent.

Insecticidal perhaloalkylvinylcyclopropanecarboxylates

Perhaloalkylvinylcyclopropanecarboxylates having the general formula STR1 are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR1 where R1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.

Preparation of esters

Certain alpha-cyano esters are prepared by reacting an acyl halide with an aldehyde in a substantially water-immiscible aprotic solvent and an aqueous solution of water-soluble cyanide salt in the presence of an amine or cryptate rate-promoting agent.