Chemical Properties
Brown solid. Easily soluble in acetone, chlorobenzene, ethanol, xylene and other organic solvents, with a solubility of 100-150g/L. Solubility in kerosene <5g/L. The solubility in water is 28mg/L. Partition coefficient (n-octanol/water) 2300 (20°C). The half-life is 7d at 60°C and pH 4, 18d at 60°C and pH 7, and the half-life in soil is 11-100d.
Uses
Flurochloridon can be used in herbicidal composition to control weed in crop fields.
Definition
ChEBI: Flurochloridone is a member of pyrrolidines, a member of (trifluoromethyl)benzenes and an organochlorine compound. It has a role as a carotenoid biosynthesis inhibitor, an agrochemical and a herbicide.
Synthesis
The synthesis of Fluorochloridone is as follows:To a 1L three-neck flask, N-allyl-N-dichloroacetyl-m-trifluoromethylaniline (31.1 g, 0.1 mol) and 715 ml of 1,2-dichloroethane were added as a solvent, dissolved under stirring, and then added. Cuprous chloride (2.97g, 0.03mol) and 2,2-bipyridyl (4.68g, 0.03mol) were reacted at 80°C for 3 hours, cooled to room temperature, and the reaction solution was filtered through a short silica gel column to give dichloromethane. Elution and desolvation yielded 31.3 g of pyrotropone, a content of 97%, an anti-contrast ratio of ≥3:1, and a yield of 97.6%.
Metabolic pathway
From hydrolytic and photolytic studies of
flurochloridone in buffer solution, no hydrolysis of
flurochloridone occurs at pH 5, 7, or 9 at 25°C or at
pH 5 at 40°C. Appreciable hydrolysis occurs at
40°C at pH 7 and 9 with half-lives of 190 and
140 days, respectively. Five hydrolytic degradation
products and six photolytic degradation products are
identified. The major photolytic degradation product
which contains 39% of the radioactivity is
4-(chloromethyl)-3-hydroxy-1-[3-
(trifluoromethyl)phenyl]-2-pyrrolidinone with a mixture
of cis and trans isomers. The formation of this major
degradation product suggests that the major
photolytic pathway involves homolytic cleavage of the
carbon ? chlorine bond at the 3-position of the
pyrrolidinone ring and the free radical intermediate can react with water to give the major product or
eliminate the hydrogen radical to form 4-
(chloromethyl)-1,5-dihydro-1-[3-
(trifluoromethyl)phenyl]pyrrol-2H-one.
Mode of action
Flurochloridone is the active substance of some pre-emergence herbicides. It has an inhibitory effect on the synthesis of carotenoids, which protect chlorophylls against oxidative stress.
Toxicity evaluation
The acute oral LD50 of male rats is 4000 mg/kg, the acute transdermal LD50 of rabbits is >5000 mg/kg, and the acute inhalation of rats is LC50 10.3 mg/L (4h). Slightly irritating to rabbit skin and eyes.
