122454-29-9

Usage

Uses

Used in Pest Control Applications:
4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile is used as an active ingredient in the development of pro-insecticides. It functions by metabolizing into an active insecticide after entering the host, providing effective pest control.
Used in Marine Antifouling Coatings:
In the marine industry, 4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile is used as a marine antifouling agent. It is incorporated into antifouling coatings applied to boat hulls, oil rig structures, and drilling platform legs that are submerged underwater. The compound helps control the growth of barnacles and other invertebrate animal fouling organisms, reducing the negative impact on the performance and efficiency of these structures.
Used in Pharmaceutical Research:
Due to its unique chemical structure, 4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile may also hold potential in the pharmaceutical industry as a starting material for the synthesis of new drugs or drug candidates. Its specific application in this field would depend on further research and development to explore its biological activities and potential therapeutic uses.

preparation

Tralopyril is an important intermediate in the synthesis of carbofuran, and bromine is the core raw material for the synthesis of Tralopyril. Tralopyril is a pyrrole resulting from the N-dealkylation of the ethoxymethyl group of chlorfenapyr. Chlorfenapyr is the first commercial proinsecticide developed by introducing ethoxymethyl group into the pyrrole N of tralopyril.

InChI:InChI=1/C12H5BrClF3N2/c13-9-8(5-18)10(19-11(9)12(15,16)17)6-1-3-7(14)4-2-6/h1-4,19H

Upstream product

• 122454-23-3 2-(p-chlorophenyl)-5-(trifluoromethyl)-pyrrole-3-carbonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 122460-66-6 4-(p-chlorophenyl)-2-(trifluoromethyl)-1,3-oxazol-5-one 
• 6212-33-5 2-(4-Chlorophenyl)glycine 

Downstream Products

• 122453-73-0 chlorfenapyr 
• 890929-85-8 4-bromo-2-(4-chlorophenyl)-1-((2-(methylsulfinyl)ethoxy)methyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 890929-86-9 4-bromo-2-(4-chlorophenyl)-1-((2-(methylsulfonyl)ethoxy)methyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 890929-78-9 4-bromo-1-((2-chloroethoxy)methyl)-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 890929-76-7 4-bromo-1-((chloromethoxy)methyl)-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 890929-87-0 4-bromo-1-((3-chloropropoxy)methyl)-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 890929-80-3 4-bromo-2-(4-chlorophenyl)-1-((2-fluoroethoxy)methyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 890929-81-4 4-bromo-1-((2-bromoethoxy)methyl)-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 

Relevant academic research and scientific papers

Preparation method of trobiglide

The present invention discloses a method of preparation of trilobiril, specifically related to the field of agricultural technology, the preparation method provided by the present invention comprises the following steps: step 1, p-chlorobenzonitrile disso

Evaluation of the molluscicidal activities of arylpyrrole on Oncomelania hupensis, the intermediate host of Schistosoma japonicum

The snail Oncomelania hupensis is the only intermediate host of the highly invasive parasite Schistosoma japonicum. Molluscicide is often used to curb transmission of S. japonicum. Niclosamide, the only World Health Organization (WHO) recognized molluscicide, presents major drawbacks, including high cost and toxicity towards aquatic animals. In the present study, a number of aryl pyrrole derivatives (ADs) were synthesized to serve as potential molluscicides and were tested on O. hupensis. To uncover the underlying mechanisms, adenosine triphosphate (ATP) and adenosine diphosphate (ADP) levels were assessed in the soft body of ADs-exposed O. hupensis, using high performance liquid chromatography (HPLC). The effect of C6 on key points of energy metabolism (the activities of complexes I, III, IV and the membrane potential) was determined. We demonstrated that the Compound 6 (C6, 4-bromo-1-(bromomethyl)-2-(4-chlorophenyl)-5- (trifluoromethyl)-1H-pyrrole-3-carbonitrile) exerted the strongest molluscicidal activity against adult O. hupensis at LC50 of 0.27, 0.19, and 0.13 mg/L for 24, 48, and 72 h respectively. Moreover, we found that the bromide on the pyrrole ring of C6 was essential for molluscicidal activity. Furthermore, the ATP content reduced from 194.46 to 139.75 mg/g after exposure to 1/2 LC50, and reduced to 93.06 mg/g after exposure to LC50. ADP, on the other hand, remained the same level before and after C6 exposure. We found that C6, at 1/2 LC50, reduced the membrane potential of O. hupensis, while no significant changes were observed in the activities of complexes I, III, and IV. C6 was identified with excellent activities on O. hupensis. The obtained structure-activity relationship and action mechanism study results should be useful for further compound design and development.

Application of 2-aryl substituted pyrrole compound in medicine for killing oncomelania hupensis

The invention relates to an application of 2-aryl substituted pyrrole compound in a medicine for killing oncomelania hupensis and belongs to the technical field of prevention and treatment of bilharziasis, and particularly provides the chemical structure of the 2-aryl substituted pyrrole compound and a preparation method of same. The 2-aryl substituted pyrrole compound, being an active component,is used for preparing the snail killing agent in the forms of suspending agents, emulsions and micro-emulsions for killing the oncomelania hupensis. Immersion killing use amount of the 2-aryl substituted pyrrole compound being the active component of the snail killing agent is 0.1-10.00 mg/l, and immersion killing time is 24-72 h. The use amount of spray application is 1-10 g/m and action timeis 3-7 days. Experiment proves that the 2-aryl substituted pyrrole compound has killing activity on the oncomelania hupensis and is lower than a snail killing agent, niclosamide, in the prior art in toxicity on aquatic organisms. The compound can be processed to prepare the snail killing agents and applied in the field of prevention and treatment of bilharziasis.

Application of 2-aryl substituted pyrrole compound in medicine for killing biomphalarid snails

The invention relates to an application of 2-aryl substituted pyrrole compound in a medicine for killing biomphalarid snails and belongs to the technical field of prevention and treatment of bilharziasis, and particularly provides the chemical structure of the 2-aryl substituted pyrrole compound and a preparation method of same. The 2-aryl substituted pyrrole compound, being an active component, is used for preparing the snail killing agent in the forms of suspending agents, emulsions and micro-emulsions for killing the biomphalarid snail. Immersion killing use amount of the 2-aryl substitutedpyrrole compound being the active component of the snail killing agent is 0.5-10.00 mg/l, and immersion killing time is 24-72 h. Experiment proves that the 2-aryl substituted pyrrole compound has killing activity on the biomphalarid snails and is lower than a snail killing agent, niclosamide, in the prior art in toxicity on aquatic organisms. The compound can be processed to prepare the snail killing agents and applied in the field of prevention and treatment of bilharziasis.

PRODUCTION OF ARYLPYRROL COMPOUNDS IN THE PRESENCE OF DIPEA BASE

The invention relates to a process for the production of compounds of formula (I), comprising Step A of reacting compounds of formula (II) with 2,3-dihalopropionitrile or 2-haloacrylonitrile in the presence of DIPEA. It also relates to a process for the production of compounds of formula (III), comprising Step B of reacting compounds of formula (I) with Br2 in the presence of DIPEA. It also relates to a process C for the production of compounds of formula (IV), comprising Step C of reacting compounds of formula (III) with di(C1-C4-alkoxy)methane and either POCl3, or a mixture comprising POCl3 and DMF, in the presence of DIPEA. It also relates to the use of DIPEA as a base in the production of compounds of formula (I), compounds of formula (III) or compounds of formula (IV).

Synthesis, insecticidal and acaricidal activities of novel 2-arylpyrroles

To search for novel 2-arylpyrroles with unique biological activities, a series of novel 2-arylpyrrole derivatives were designed and synthesized, and their structures were characterized by 1H and 13C NMR spectroscopy, MS spectrometry, and elemental analysis. Their insecticidal activities against Lepidopteran pests (e.g. Mythimna separata) and acaricidal activities against mites (e.g. Tetranychus urticae) were evaluated. The results of bioassays indicate that some of these title compounds exhibited excellent insecticidal and acaricidal activities. For example, 4-bromo-1-((chloromethoxy) methyl)-2-(4-chloro phenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (6a), 4-bromo-2-(4-chlorophenyl)-1-((2-fluoroethoxy)-methyl)-5-(trifluoromethyl) pyrrole-3-carbonitrile (6d) showed insecticidal activity against Mythimna separata and 4-bromo-2-(4-chlorophenyl)-1-((isopropoxymethoxy)methyl)-5- (trifluoro methyl)pyrrole-3-carbonitrile (7d) showed acaricidal activity against Tetranychus urticae. They were more effective than Chlorfenapyr, which has been the only commercialized member of a new class of chemicals of 2-arylpyrroles.

Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl) methyl] arylimidoyl chloride compounds

There is provided a process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl)methyl]arylimidoyl chloride compounds. The 2-aryl-5-(perfluoroalkyl)pyrrole compounds are useful for the control of insect and

Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl)methyl]arylimidoyl chloride compounds

There is provided a process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds of formula I from N-[1-chloro-1-(perfluoroalkyl)methyl]arylimidoyl chloride compounds. The 2-aryl-5-(perfluoroalkyl)pyrrole compounds are useful for the control

Arylpyrroles for subterranean termite control

The present invention provides a method for the control of subterranean termite populations which comprises applying to the soil a termiticidally effective amount of an arylpyrrole compound of formula I. STR1

2-aryl-4-halo-5-(trifluoromethyl)pyrrole-3-carbonitriles for the protection of wood, wood products and wooden structures from insect attack

The present invention provides a method for the protection of wood, wood products and wooden structures from wood-eating insect attack and infestation which comprises treating said wood, wood product or wooden structure or the soil surrounding said wood, wood product or wooden structure with an insecticidally effective amount of an arylpyrrole compound of formula I.