4-Cyanotetrahydropyran

Synthesis

4-Cyanotetrahydropyran can be obtained by chlorination of phenol with chlorine gas to obtain 2,4,6-trichlorophenol, which is then condensed with p-nitrochlorobenzene.

Description

Chlornitrofen is an obsolete rice herbicide, It has a low aqueous solubility and is non-volatile. It is moderately toxic to fish, algae and aquatic invertebrates. Chlornitrofen has a low oral mammalian toxicity and may be a reproduction/developmental toxin.

Chemical Properties

Yellow crystalline powder. Melting point 107°C, boiling point 210°C (0.8-0.93kPa), relative density 1.6424 (23/4°C). Vapor pressure 47Pa at 109°C. Freely soluble in benzene, toluene, slightly soluble in ether, insoluble in water (0.25ppm at 25°C).

Uses

Herbicide.

Definition

ChEBI: Chlornitrofen is an aromatic ether, a member of chlorobenzenes and a C-nitro compound. It has a role as an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor and a herbicide.

Mechanism of action

Selective, contact. Protoporphyrinogen oxidase inhibitor.

Safety Profile

Low toxicity by ingestion and skincontact. Mutation data reported. Used as an herbicide.When heated to decomposition it emits very toxic fumesof NOx and Clí.

Metabolic pathway

Degradation of chlornitrofen by microorganisms isolated from soils gives rise to the reduction of the nitro group of chlornitrofen to the amino analog, and the successive N-acetylation or N-methylation and the cleavage of the ether linkage are dominant metabolic pathways. The metabolic pathways, however, differ depending on microorganisms and the media. The replacement of the amino group by hydroxyl group, the reduction and successive formylation of p-nitrophenol, and the cleavage of the phenyl ring ultimately to produce CO2 are also observed.

Pesticide Type

Herbicide