91465-08-6

Basic information

• Product Name: Cyhalothrin
• Synonyms: a-cyano-3-phenoxybenzyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylate;Cyano-3-phenoxybenzyl(1S+1R)-cis-3-(z-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylate;LAMBDA-CYHALOTHRIN PESTANAL, 100 MG;LAMBDA-CYHALOTHRIN, 100MG, NEAT;cishalothrin;Darate;α-Cyano-3-phenoxybenzyl 3-(2-chloro-3,3,3-trifluoro-prop-1-enyl)-2,2,-dimethylcyclopropane 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-
• CAS NO: 91465-08-6
• Molecular Formula: C₂₃H₁₉ClF₃NO₃
• Molecular Weight: 449.85
• EINECS: 415-130-7
• Product Categories: INSECTICIDE;AcaricidesPesticides&Metabolites;Alpha sort;C;CAlphabetic;CO - CZMethod Specific;Insecticides;Oeko-Tex Standard 100;Pesticides;Pesticides&Metabolites;PesticidesPesticides;Pyrethroids;Agro-Products;Aromatics
• Mol File: 91465-08-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 49.2°C
• Boiling Point: 187-190°C
• Flash Point: 255.5 °C
• Appearance: /
• Density: 1.3225 (estimate)
• Storage Temp.: 2-8°C
• Merck: 13,2787
• CAS DataBase Reference: Cyhalothrin(CAS DataBase Reference)
• NIST Chemistry Reference: Cyhalothrin(91465-08-6)
• EPA Substance Registry System: Cyhalothrin(91465-08-6)

Safety Data

• Hazard Codes: T+;N,N,T+,Xn
• Statements: 21-25-26-50/53-20/21/22
• Safety Statements: 1/2-28-36/37/39-38-45-60-61-13
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• RTECS: GZ1227780
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 91465-08-6(Hazardous Substances Data)

Usage

Description

Cyhalothrin is a broad-spectrum pesticide and acaricide that is used to control a wide range of pests in a variety of applications. It belongs to the pyrethroid, a class of synthetic insecticides which has the similar structure and insecticidal activity of the naturally occurring insecticide pyrethrum, derived from the flowers of chrysanthemums. It is commercially used for controlling insects on non-food crops, greenhouses, hospitals, and crops, such as cotton, cereals, hops, ornamentals, potatoes, vegetables, etc. and it targets various kinds of pests, including aphids, Colorado beetles and butterfly larvae. Besides, it is effective to used in public health applications to control insects identified as potential disease vectors, such as cockroaches, mosquitoes, ticks, and flies. Registered with the EPA in 1988, Cyhalothrin is often preferred as an active ingredient in insecticides because it is proved to be mostly insoluble in water, which is an unlikely water contaminant. It is also nonvolatile, which makes it remain effective for extended periods of time.

References

https://en.wikipedia.org/wiki/Cyhalothrin http://pmep.cce.cornell.edu/profiles/extoxnet/haloxyfop-methylparathion/lambda-cyhalothrin-ext.html http://www.toxipedia.org/display/toxipedia/Lambda-Cyhalothrin

Chemical Properties

olorless to beige powder; or viscous yellowish-brown liquid. Mild odor. Liquid formulations containing organic solvents may be flammable.

Uses

Insecticide; pyrethrin analog

Agricultural Uses

Insecticide; acaridide: A U.S. EPA restricted Use Pesticide (RUP). Only cyhalothrin is banned for use in EU; not lamda-isomer; CAS 68085-85-8). Used to control a variety of pests in many crops. Also used in structural pest situations..

Trade name

CHARGE?; COMMODORE?; DEMAND?; DEMAND CS?; DOUBLE BARREL?; EXCALIBER?; GRENADE?; HALLMARK?; ICON?; IMPASSE?; KARATE?; MATADOR?; NINJA?; PP321?; RATE?; SABER?; SAMURAI?; SCIMITAR?; SENTINEL?; WARRIOR?

Potential Exposure

Pyrethroid insecticide and acaridide used to control a variety of pests in many crops. Also used in structural pest situations. A United States Environmental Protection Agency Restricted Use Pesticide (RUP). Only cyhalothrin is banned for use in EU; not the lamda-isomer (CAS 68085-85-8).

Metabolic pathway

The solution and solid-phase photodecomposition of cyhalothrin involves E/Z and cis/trans isomerization reactions and frees radical processes leading to decarboxylation, ester cleavage, proton abstraction, oxygen scavenging, and reactions with solvent- generated radicals. The major degradation products are decarboxylated analogs which are also isomerized at the cyclopropyl and vinyl groups. In vitro incubation of 14C-cyhalothrin with honey bee mid-guts yields the principal metabolite identified as 4-hydroxy-3-phenoxybenzyl alcohol with a small amount of 3-phenoxybenzoic acid. In vivo metabolism with honey bees shows the major metabolites 4'-hydroxy-and 2'-hydroxy-3-phenoxybenzyl alcohols and 4'-hydroxy-3-phenoxybenzoic acid. Prochloraz delays the metabolism, detoxication, and excretion of cyhalothrin by inhibition of microsomal oxidation, effectively enhancing the toxicity to the honey bee.

Shipping

UN3349 Pyrethroid pesticide, solid toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous material. UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.br UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Incompatibilities

May react violently with strong oxidi- zers, bromine, 90% hydrogen peroxide, phosphorus trichloride, silver powders, or dust. Incompatible with silver compounds. Mixture with some silver compounds forms explosive salts of silver oxalate. Hydrolyzed by water

Synthetic route

(1R,3R)-3-((Z)-2-Chloro-3,3,3-trifluoro-propenyl)-2,2-dimethyl-cyclopropanecarboxylic acid cyano-(3-phenoxy-phenyl)-methyl ester (91465-08-6) → (S)-α-cyano-3-phenoxybenzyl (Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropane carboxylate (91465-08-6)

Conditions	Yield
With diisopropylamine In water; isopropyl alcohol at -5℃; for 65h;	97%

sodium cyanide (773837-37-9) + (Z)-3-(2-chloro-2-trifluoromethylvinyl)-2,2-dimethylcyclopropionyl chloride (139237-90-4) + 3-Phenoxybenzaldehyde (39515-51-0) → (S)-α-cyano-3-phenoxybenzyl (Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropane carboxylate (91465-08-6)

Conditions	Yield
In hexane; water at 6℃; for 8h;	32%

(Z)-3-(2-chloro-2-trifluoromethylvinyl)-2,2-dimethylcyclopropionyl chloride (139237-90-4) + (S)-m-phenoxybenzaldehyde cyanohydrin (39515-47-4, 52315-06-7, 61826-76-4, 71962-66-8) → λ-cyhalothrin (76703-63-4) + (S)-α-cyano-3-phenoxybenzyl (Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropane carboxylate (91465-08-6)

Conditions	Yield
Stage #1: (Z)-3-(2-chloro-2-trifluoromethylvinyl)-2,2-dimethylcyclopropionyl chloride; (S)-m-phenoxybenzaldehyde cyanohydrin In cyclohexane at 80℃; for 25.5h; Stage #2: With pyridine In cyclohexane for 3h; Heating / reflux;
With pyridine In toluene at -10℃; for 2 - 4h;
With Sodium borate In hexane; water at 10℃; for 2h; pH=9;

Upstream product

• 393870-46-7 3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarbonyl chloride 
• 111-51-3 N,N,N',N'-tetramethyl-1,4-butanediamine 
• 39515-51-0 3-Phenoxybenzaldehyde 
• 82561-08-8 N-(α-cyano-3-phenoxybenzyl)-N,N,N-trimethylammonium methylsulfate 
• 108-10-1 4-methyl-2-pentanone 
• 139237-90-4 (Z)-3-(2-chloro-2-trifluoromethylvinyl)-2,2-dimethylcyclopropionyl chloride 
• 39515-47-4 (S)-m-phenoxybenzaldehyde cyanohydrin 
• 39515-47-4 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile 
• 773837-37-9 sodium cyanide 

Relevant articles and documents

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 PRPARING GAMMA-CYHALOTHRIN

A process for the preparation of gamma-cyhalothrin comprising steps of a) chlorinating 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid to give 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride and b) esterifying 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride with the (S)-cyanohydrin of 3-phenoxy benzaldehyde (III).

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.