23496-29-9

Usage

Use

Broad-spectrum, non-systemic, low toxicity insecticide

Application

Control of insects in various agricultural and horticultural crops

Mechanism of action

Affects the nervous system of insects, causing paralysis and death

Veterinary use

Control of external parasites on livestock

Environmental concern

Highly toxic to aquatic organisms

Risk

Poses a risk to the environment if not used properly and responsibly

Upstream product

• 79-36-7 dichloroacethyl chloride 
• 100-61-8 N-methylaniline 
• 708-88-3 N-methyl-N-(trichlorovinyl)aniline 
• 56-23-5 tetrachloromethane 
• 579-10-2 N-acetyl-N-methylaniline 
• 79-34-5 1,1,2,2-tetrachloroethane 
• 79-43-6 dichloro-acetic acid 
• 36558-96-0 N-methyl-N-phenyltrichloroacetamide 

Downstream Products

• 2210-39-1 N-Methyl-anilinoaethylen-1.2-bis-(tributylphosphonium)-dichlorid 
• 1134192-65-6 4-(4-bromophenyl)-3-hydroxy-1-methylquinolin-2(1H)-one 
• 2620-05-5 N-methyl-2-chloroacetanilide 
• 704-27-8 N-Methyl-N-phenyl-1.2-dichlor-vinylamin 

Relevant academic research and scientific papers

A New and Practical Synthesis of Indolones

A variety of indolones can be obtained from α-haloanilides through a radical cyclisation mediated by a combination of nickel powder and acetic acid.

Synthesis and Mechanistic Insights of the Formation of 3-Hydroxyquinolin-2-ones including Viridicatin from 2-Chloro- N,3-diaryloxirane-2-carboxamides under Acid-Catalyzed Rearrangements

N-Benzyl-2-chloro-N,3-diaryloxirane-2-carboxamides, easily obtained from aromatic aldehydes and anilides of dichloroacetic acid under Darzens condensation conditions, proved to be excellent starting compounds for the synthesis of 3-hydroxyindolin-2-ones, cyclohepto[b]pyrrole-2,3-diones, and 1-azaspiro[4.5]deca-3,6,9-triene-2-ones via the C(sp2)-C(sp2) bond formation in the first case and C(sp2)-C(sp3) bond formation in the second and third cases. Under optimized reaction conditions, 3-hydroxyindolin-2-ones are obtained in a one-pot process, which involves the treatment of N-benzyl-2-chloro-N,3-diaryloxirane-2-carboxamides with CF3CO2H or AcOH/H2SO4. In the case of intramolecular cyclization, the detailed reaction channels depend strongly on the substituents present in the anilide component and in the aromatic ring of the aldehyde component of N-benzyl-2-chloro-N,3-diaryloxirane-2-carboxamides, as well as the temperature and duration of the reaction. A combined experimental and DFT mechanistic study of the formation of 1-benzyl-3-hydroxy-4-arylquinolin-2(1H)-ones showed that there are three competing reaction channels: (a) ring-closure via the ipso site, (b) ring-closure via the 1,2-Cl shift, and (c) ring-closure via the ortho site. Such mechanistic insights enabled an effective one-pot gram-scale synthesis of viridicatin from benzaldehyde and 2,2-dichloro-N-(4-methoxybenzyl)-N-phenylacetamide.

Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel-Crafts Alkylation Strategy

The new efficient synthesis of biologically important 3-hydroxy-4-arylquinolin-2-ones through the Darzens condensation (epoxidation) of dichloroacetanilides with aromatic aldehydes followed by one-pot dechlorative epoxide-arene cyclization is described. T

Investigation of the Potential of Molybdenum(VI) Hydrazido(2-) Complexes as Sources of Nitrenium Ions: Cleavage of the N-N Bond and Incorporation of the β-Nitrogen Group into Solvent Molecules

Photolyis or thermolysis of bis(N,N-dimethyldithiocarbamato)bismolybdenum(VI) complexes in 1,1,2,2-tetrachloroethane results predominantly in transfer of the hydrazido group to the solvent with formation of dichloroacetohydrazides.A small amount of the corresponding dichloroacetamides are produced by N-N cleavage and N(R)Ph transfer.In contrast, the latter process dominates the reaction of dichlorobis(N,N-dimethyldithiocarbamato)mono-molybdenum(VI) complexes with silver nitrate in alcohols occuring concomitantly with ring methoxylation and nitration and N-nitrosation.Neither transfer of N(R)Ph appears to involve free nitrenium ions.

HYDRODEHALOGENATION OF TRICHLOROACETAMIDES DURING THERMOCATALYTIC DECOMPOSITION OF SODIUM TRICHLOROACETATE

N-Substituted trichloroacetamides are reduced to the corresponding dichloroacetamides during the thermal decomposition of sodium trichloroacetate in chloroform in the presence of benzyltriethylammonium chloride as phase-transfer catalyst.The relative reac

THE REACTION OF DICHLOROCARBENE WITH TETRTIARY CARBOXAMIDES. PREPARATION OF α-CHLOROMETHYLENELACTAMS AND (E)-CHLOROACRYLAMIDES

An easy method is described for the preparation of (E)-3-chloroacrylamides and α-chloromethylenelactams which is based on the simple treatment of tertiary carboxamides and lactams with dichlorocarbene.

Substituted chloroacylanilides

The invention concerns a process for the preparation of substituted chloroacylanilides of the general formula: SPC1 Wherein R1 represents an alkyl group having from 1 to 4 carbon atoms or a phenyl group; R2 represents a hydrogen atom or halogen atom; R3 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms and X1 and X 2 , which may be the same or different, represent a hydrogen atom, a halogen atom, a methyl group or an ethyl group. The process comprises acylating a substituted aniline of the general formula: SPC2 Wherein R1, X1 and X2 are as above defined, in the presence of phosphoryl chloride under substantially anhydrous conditions with a chlorocarboxylic acid of the general formula: EQU1 wherein R2 and R3 are as above defined. Particularly suitable compounds of general Formula II are N-methyl aniline and N-isopropyl aniline, and particularly suitable compounds of general Formula III are chloroacetic acid, dichloroacetic acid and α-chloropropionic acid and α-chlorobutyric acid. The compounds of general Formula I have phytotoxic effects and some are active herbicides.