111992-16-6

Basic information

• Product Name: 2-(2,4-Dichlorophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one
• Synonyms: 2-(2,4-Dichlorophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one;2-(2,4-dichlorophenyl)-4-(difluoromethyl)-5-methyl-1,2,4-triazol-3-one
• CAS NO: 111992-16-6
• Molecular Formula: C10H7Cl2F2N3O
• Molecular Weight: 294.08
• Mol File: 111992-16-6.mol

Chemical Properties

• Melting Point: 111-113 °C
• Boiling Point: 335.639 °C at 760 mmHg
• Flash Point: 156.789 °C
• Appearance: /
• Density: 1.60
• PKA: -2.55±0.20(Predicted)
• CAS DataBase Reference: 2-(2,4-Dichlorophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,4-Dichlorophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one(111992-16-6)
• EPA Substance Registry System: 2-(2,4-Dichlorophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one(111992-16-6)

Safety Data

• Hazardous Substances Data: 111992-16-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Fluconazole is used as an antifungal agent for treating a wide range of fungal infections. It is effective against yeast infections affecting the mouth, throat, esophagus, lungs, bladder, genital area, and blood. The medication works by inhibiting the synthesis of fungal cell membranes, thereby stopping fungal growth.
Used in Oral and Intravenous Administration:
Fluconazole is available in both oral and intravenous forms, providing flexibility in treatment options for patients. The oral form is convenient for outpatient treatment, while the intravenous form is useful for patients who cannot take oral medications or require more immediate and controlled administration.
Used with Caution in Liver or Kidney Disease Patients:
Fluconazole should be used with caution in patients with liver or kidney disease, as it can interact with certain medications and may require dosage adjustments. Monitoring of liver and kidney function is recommended during treatment to ensure safety and efficacy.
Used in Interaction Management:
Due to potential interactions with other medications, healthcare providers need to be aware of the patient's medication profile when prescribing Fluconazole. This ensures that the treatment is safe and does not lead to adverse effects or reduced efficacy of other medications.

Upstream product

• 75-45-6 Chlorodifluoromethane 
• 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 
• 103998-84-1 2-(2-(2,4-dichlorophenyl)hydrazono)propanoic acid 
• 109913-40-8 1-(2-chlorophenyl)-3-methyl-1H-1,2,4-triazol-5(4H)-one 
• 22863-24-7 1-phenyl-3-methyl-1H-1,2,4-triazol-5-one 
• 24660-31-9 acetaldehyde 4-chlorophenylhydrazone 
• 133840-72-9 4,5-dihydro-3-methyl-1-(4-chlorophenyl)-1,2,4-triazol-5(1H)-one 
• 106-47-8 4-chloro-aniline 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 95-51-2 o-chloroaniline 
• 10449-07-7 (2-chlorophenyl)hydrazine 
• 62-53-3 aniline 
• 100-63-0 phenylhydrazine 

Downstream Products

• 111992-18-8 2-(5-amino-2,4-dichlorophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one 

Relevant articles and documents

Preparation method of 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazole-5-one

The invention provides a preparation method of 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazole-5-one. The method comprises the steps: taking aniline as a raw material; reducing witha catalyst X to prepare phenylhydrazine; under the action of acetaldehyde and sodium cyanate, carrying out cyclization on phenylhydrazine to generate 1-phenyl-3-methyl-1H-1,2,4-triazole-5-one; carrying out a reaction on 1-phenyl-3-methyl-1H-1,2,4-triazole-5-one and monochlorodifluoromethane under the action of a catalyst Y to generate 1-phenyl-3-methyl-4-difluoromethyl-1H-1,2,4-triazole-5-one, and carrying out catalytic chlorination through a catalyst Z to prepare 1-(2,4-dichlorophenyl)-4-difluoromethyl-3-methyl-1H-1,2,4-triazole-5-one.

Method for preparing sulfentrazone intermediate

The invention relates to the field of pesticides, in particular to a method for preparing a sulfentrazone intermediate. The method comprises the steps that in the presence of water and a first organicsolvent, a compound with the structure shown in the formula (II) and chlorine are subjected to a contact reaction, X and Y are independently selected from H and Cl, and X and Y are not Cl at the sametime; R is H or difluoromethyl; the contact reaction comprises an oxidation contact reaction and a chlorination contact reaction in sequence, and the conditions of the oxidation contact reaction areas follows: the temperature is 5-35 DEG C, and the time is 30-120 minutes; and the conditions of the chlorination contact reaction are as follows: the temperature is 40-90 DEG C, and the time is 3-6 hours. According to the method, the yield and the purity of the sulfentrazone intermediate with the structure shown in the formula (I) can be effectively improved, and the method is easy to operate andmore environmentally friendly.

Synthesizing method of sulfentrazone

The invention discloses a synthesizing method of sulfentrazone. The synthesizing method comprises the following steps of using a compound (II) as the raw material, and performing difluoro methylation,chlorination and bromination; then, performing methylsulfonylation, so as to obtain the final product of the sulfentrazone. The synthesizing method has the advantages that the obtained intermediate after chlorination is firstly brominated, and then the obtained intermediate after bromination and the methanesulfonamide are catalyzed by a catalyst to obtain the sulfentrazone; the chemical selectivity is high, and the dangerous technologies of nitrification, hydrogenation and the like in the traditional technology route are avoided; the production of a large amount of waste acid and waste waterin the nitrification process is avoided, the green effect is better, the efficiency is higher, and the safety and reliability are higher; the whole technology is simple and convenient, and the reaction conditions are mild; by adjusting the reaction conditions, the yield rate of the obtained product is high, the quality of the product is high, and the synthesizing method is suitable for industrialized production.

Method for synthesizing 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone

The invention discloses a method for synthesizing 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone. The method takes p-chloroaniline as a raw material, through diazotization, reduction, and salt forming, p-chlorophenylhydrazine hydrochloride is synthesized, p-chlorophenylhydrazine is obtained through alkali neutralization, under condition that tert-butyl alcohol is taken asa solvent, chlorophenylhydrazine, acetaldehyde, sodium cyanate and sodium hypochlorite are subjected to condensation, cyclisation and an oxidation reaction to generate 1-p-chlorophenyl-3-methyl-1H-1,2,4-triazole-5-ketone, and the 1-p-chlorophenyl-3-methyl-1H-1,2,4-triazole-5-ketone is subjected to salt forming, reaction with chlorodifluoromethane, and chlorination to obtain the 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone (a sulfentrazone intermediate). The synthetic method takes p-chloroanniline as the raw material, the synthetic method is realized by only one-time chlorination, steric hindrance for intermediate synthesis is small, and the impurity is low, so that the yield is increased; in addition, the raw materials required by the synthesis route are easilyacquired, the cost is low, the condition is mild, operation is simple, security is high, and the synthesis method is in favor of realizing industrial production.

Method for synthesizing 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone

The invention discloses a method for synthesizing 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone. The method comprises the following steps: with o-chloroaniline as a raw material, carrying out diazotization, reduction and salific

NOVEL FORM OF SULFENTRAZONE, PROCESS FOR ITS PREPARATION AND USE THEREOF

The invention describes a new crystalline form of sulfentrazone and its preparation process. The invention also describes the analyses of the crystal through various analytical methods and the use of the crystal to prepare stable agrochemical formulation. The novel crystal form is particularly suitable for use in herbicidal compositions and in the control of unwanted plant growth.

Method for synthesizing a sulphur grass amine intermediate and armor sulphur grass amine method

The invention discloses a method for synthesizing a sulfentrazone midbody and sulfentrazone. The method comprises the following steps: preparing the sulfentrazone midbody (III) from 1-phenyl-3-methyl-1H-1,2,4-triazole-5-ketone used as a raw material in an aprotic solvent in the presence of a compound (A) or a compound (B) and alkali, performing difluoro methylation to obtain a midbody (IV), performing chlorination, nitration and reduction, and further performing methyl sulfone chloride sulfonylation to obtain a final product, namely, N(2,4-difluoro-5-(4-difluoro methyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl) phenyl) sulfamide. The method has the main beneficial effects that due to an adopted catalytic hydrogenation process, the nitroreduction is not only high in chemical selectivity, but also is more environment-friendly, efficient, safe and reliable, as triphenylphosphine, polyethylene glycol or crown ether is used as a catalyst which takes the place of a conventional used catalyst such as DMF (Dimethyl Formamide) in the sulfonylation reaction, less side reaction is caused, and the yield is high. The overall process is simple and convenient, the reaction condition is gentle, the yield is high, the product quality is high, and the industrial production is facilitated.

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.

Syntheses and herbicidal activities of novel triazolinone derivatives

Protoporphyrinogen oxidase (Protox, EC 1.3.3.4) has been identified as one of the most important action targets of herbicides. To search for novel Protox inhibitors, a series of title compounds 1, 2, and 3 were designed and synthesized by introducing three types of pharmacophores, cyclic imide, phenylurea, and (E)-methyl 2-methoxyimino-2-o-tolylacetate, into the scaffold of triazolinone. The bioassay results indicated that the resulting cyclic imide-type triazolinones 1 displayed much better herbicidal activities than phenylurea-type triazolinones 2. Most fortunately, compound 3, methyl 2-[3-methyl-(2-fluoro-4-chloro-5-ethylsulfonamidephenyl)-4,5-dihydro-5-oxo-1H-1, 2,4-triazol-4-yl]methyl-enephenyl-2-(E)-methoxyiminoacetate, was found to be the most promising candidate due to its comparable herbicidal activity at 75-150 g of active ingredient/ha with the commercial product sulfentrazone. On the basis of test results of herbicidal spectrum and crop selectivity, compound 3 could be developed as a postemergent herbicide used for the control of broadleaf weeds in rice fields.