111992-17-7

Basic information

• Product Name: 2-(2,4-Dichloro-5-nitrophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one
• Synonyms: 2-(2,4-Dichloro-5-nitrophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one
• CAS NO: 111992-17-7
• Molecular Formula: C10H6Cl2F2N4O3
• Molecular Weight: 339.08
• Mol File: 111992-17-7.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.79
• CAS DataBase Reference: 2-(2,4-Dichloro-5-nitrophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,4-Dichloro-5-nitrophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one(111992-17-7)
• EPA Substance Registry System: 2-(2,4-Dichloro-5-nitrophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one(111992-17-7)

Safety Data

• Hazardous Substances Data: 111992-17-7(Hazardous Substances Data)

Usage

General Description

The chemical 2-(2,4-Dichloro-5-nitrophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one, also known as diflumidone, is a systemic fungicide used to control a wide range of fungal diseases in crops and plants. It works by inhibiting the enzyme succinate dehydrogenase in the fungal cells, disrupting the energy production process and ultimately leading to the death of the fungi. Diflumidone is commonly used in agriculture, horticulture, and forestry, and is known for its long-lasting protective effects and low toxicity to non-target organisms. However, it is important to use this chemical with caution and in accordance with safety guidelines to minimize environmental and health risks.

Upstream product

• 111992-16-6 4,5-dihydro-3-methyl-4-difluoromethyl-1-(2,4-dichlorophenyl)-1,2,4-triazol-5(1H)-one 
• 22863-24-7 1-phenyl-3-methyl-1H-1,2,4-triazol-5-one 
• 109913-40-8 1-(2-chlorophenyl)-3-methyl-1H-1,2,4-triazol-5(4H)-one 
• 103998-84-1 2-(2-(2,4-dichlorophenyl)hydrazono)propanoic acid 
• 79604-49-2 4,5-dihydro-1-(2,4-dichlorophenyl)-3-methyl-1,2,4-triazol-5(1H)-one 
• 554-00-7 2,4-Dichloroaniline 

Downstream Products

• 122836-35-5 sulfentrazone 

Relevant articles and documents

Preparation method of farm chemical intermediate aryl triazolinone compound

The invention discloses a preparation method of a farm chemical intermediate aryl triazolinone compound, which comprises the following steps: S1, adding raw materials and a solvent into a reactor, dropwisely adding a nitration reagent into the reactor whi

Method for synthesizing Sulfentrazone

The invention relates to a method for synthesizing Sulfentrazone. The method is characterized by comprising the steps of liberating o-chlorophenylhydrazine from o-chlorophenylhydrazine hydrochloride, which serves as a raw material, by an alkali, subjecting o-chlorophenylhydrazine to a reaction with trimethyl orthoacetate and potassium cyanate so as to obtain 1-o-chlorophenyl-3-methyl-1H-1,2,4-triazol-5-one, and then, subjecting 1-o-chlorophenyl-3-methyl-1H-1,2,4-triazol-5-one to N-alkylation, chlorination, nitration, reduction and sulfonylation, thereby obtaining the Sulfentrazone, wherein a composite catalyst and a solvent, i.e., dichloroethane are adopted in a chlorination reaction. The method for synthesizing the Sulfentrazone, disclosed by the invention, has the advantages that the o-chlorophenylhydrazine hydrochloride serves as the raw material, so that the steric hindrance of an intermediate product can be low, and the yield of the product is increased; and meanwhile, in the chlorination reaction, the composite catalyst is adopted, thus, the orientation effect on all atoms is good, and the solvent is dichloroethane, so that the recycling of the solvent is facilitated.

Design and synthesis of 1-(benzothiazol-5-yl)-1H-1,2,4-triazol-5-ones as protoporphyrinogen oxidase inhibitors

Protoporphyrinogen oxidase (PPO, E.C. 1.3.3.4) is the action target for several structurally diverse herbicides. A series of novel 4-(difluoromethyl)-1- (6-halo-2-substituted-benzothiazol-5-yl)-3-methyl-1H-1,2,4-triazol-5(4H)-ones 2a-z were designed and synthesized via the ring-closure of two ortho-substituents. The in vitro bioassay results indicated that the 26 newly synthesized compounds exhibited good PPO inhibition effects with Ki values ranging from 0.06 to 17.79 μM. Compound 2e, ethyl 2-{[5-(4- (difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl) -6-fluorobenzo-thiazol-2-yl]thio}acetate, was the most potent inhibitor with Ki value of 0.06 μM against mtPPO, comparable to (Ki = 0.03 μM) sulfentrazone. Further green house assays showed that compound 2f (Ki = 0.24 μM, mtPPO), ethyl 2-{[5-(4-(difluoromethyl)-3-methyl-5- oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-yl]thio} propanoate, showed the most promising post-emergence herbicidal activity with broad spectrum even at concentrations as low as 37.5 g ai/ha. Soybean exhibited tolerance to compound 2f at the dosages of 150 g ai/ha, whereas they are susceptible to sulfentrazone even at 75 g ai/ha. Thus, compound 2f might be a potential candidate as a new herbicide for soybean fields.