| 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 | Flurochloridone (FLC) is a monophenyl pyrrolidinone selective herbicide that can be used in herbicidal composition to control weed in crop fields. It is commonly used to inhibit weeds that occur during the growth of crop plants, such as grains, sunflowers, and potatoes. |
| 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%.
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| Metabolic pathway | From hydrolytic and photolytic studies offlurochloridone in buffer solution, no hydrolysis offlurochloridone occurs at pH 5, 7, or 9 at 25°C or atpH 5 at 40°C. Appreciable hydrolysis occurs at40°C at pH 7 and 9 with half-lives of 190 and140 days, respectively. Five hydrolytic degradationproducts and six photolytic degradation products areidentified. The major photolytic degradation productwhich contains 39% of the radioactivity is4-(chloromethyl)-3-hydroxy-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone with a mixtureof cis and trans isomers. The formation of this majordegradation product suggests that the majorphotolytic pathway involves homolytic cleavage of thecarbon ? chlorine bond at the 3-position of thepyrrolidinone ring and the free radical intermediate can react with water to give the major product oreliminate 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. |
| References | [1] Patent: CN107868029, 2018, A. Location in patent: Paragraph 0012-0018 |
