122453-73-0

Usage

Reference

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3039634/ https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-129093_01-Jan-01.pdf https://sitem.herts.ac.uk/aeru/ppdb/en/Reports/136.htm https://en.wikipedia.org/wiki/Chlorfenapyr https://www.pwrc.usgs.gov/resshow/Albers/albers1.htm

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 122453-73-0 differently. You can refer to the following data:
1. Chlorfenapyr is a halogenated pyrrole based pro-insecticide. Chlorfenapyr functions by metabolizing into an active insecticide after entering the host. Chlorfenapyr is used primarily as a means of pes t control on cotton.
2. Insecticide. Acaricide.

Hazard

A poison by ingestion. Moderately toxic by inhalation.

Agricultural Uses

Acaracide, Insecticide, Miticide: Severely Restricted for use in EU. Active in U.S. as a foliar spray in greenhouses for ornamental crops and target pests including mites, caterpillar pests, thrips, and fungus gnats. No food use in U.S. Used on ornamental crops in commercial greenhouses to control mites, caterpillar pests, thrips and fungus gnats. Not for food use. Not an approved substance in EU countries. Registered for use in the U.S.

Trade name

AC 303630?; CL 303630?; PHANTOM?; PIRATE? 3 F; PYLON?; SUMILARV? chlorfenapyr Chemical class: Pyrrole (Pyrazole); Organofluorine

InChI:InChI=1/C15H11BrClF3N2O/c1-2-23-8-22-13(9-3-5-10(17)6-4-9)11(7-21)12(16)14(22)15(18,19)20/h3-6H,2,8H2,1H3

Synthetic route

tralopyril (122454-29-9) + ethyl chloromethyl ether (3188-13-4) → chlorfenapyr (122453-73-0)

Conditions	Yield
Stage #1: tralopyril With sodium hydroxide at 20℃; for 0.333333h; Stage #2: ethyl chloromethyl ether at 60℃; for 2h; Reagent/catalyst; Temperature;	98%
Stage #1: tralopyril With sodium hydroxide at 20℃; for 0.333333h; Stage #2: ethyl chloromethyl ether at 60℃; for 2h; Reagent/catalyst; Temperature;	98%
In tetrahydrofuran

formaldehyde diethyl acetal (462-95-3) + tralopyril (122454-29-9) → chlorfenapyr (122453-73-0)

Conditions	Yield
Stage #1: formaldehyde diethyl acetal; tralopyril With trichlorophosphate In toluene at 97℃; for 0.5h; Stage #2: With triethylamine In toluene at 97℃; for 5h;	92.3%
Stage #1: formaldehyde diethyl acetal; tralopyril With trichlorophosphate In toluene at 97℃; for 0.5h; Stage #2: With triethylamine In toluene at 97℃; for 5h;	92.3%
Stage #1: formaldehyde diethyl acetal; tralopyril With trichlorophosphate In N,N-dimethyl-formamide; toluene at 35 - 53℃; for 0.666667h; Inert atmosphere; Stage #2: With triethylamine In N,N-dimethyl-formamide; toluene at 35 - 45℃; for 2h;
Stage #1: formaldehyde diethyl acetal; tralopyril With trichlorophosphate In toluene at 45 - 65℃; for 1h; Stage #2: With N-ethyl-N,N-diisopropylamine In toluene at 40 - 50℃; for 1h; Reagent/catalyst;

dimethylformamide [DMF] + formaldehyde diethyl acetal (462-95-3) + tralopyril (122454-29-9) → chlorfenapyr (122453-73-0)

Conditions	Yield
With triethylamine; trichlorophosphate In water; toluene

4-bromo-1-(chloromethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile → chlorfenapyr (122453-73-0)

Conditions	Yield
With sodium ethanolate In ethanol

2-(4-Chlorophenyl)glycine (6212-33-5) → chlorfenapyr (122453-73-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine; trichlorophosphate / 5 h / 65 °C 2.1: 20 °C / Reflux 3.1: acetic acid; sodium acetate; bromine / 2.17 h / 90 - 110 °C 4.1: sodium hydroxide / 0.33 h / 20 °C 4.2: 2 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1.1: triethylamine; trichlorophosphate / 5 h / 65 °C 2.1: 20 °C / Reflux 3.1: acetic acid; sodium acetate; bromine / 2.17 h / 90 - 110 °C 4.1: trichlorophosphate / toluene / 0.5 h / 97 °C 4.2: 5 h / 97 °C View Scheme

4-(p-chlorophenyl)-2-(trifluoromethyl)-1,3-oxazol-5-one (122460-66-6) → chlorfenapyr (122453-73-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 20 °C / Reflux 2.1: acetic acid; sodium acetate; bromine / 2.17 h / 90 - 110 °C 3.1: sodium hydroxide / 0.33 h / 20 °C 3.2: 2 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1.1: 20 °C / Reflux 2.1: acetic acid; sodium acetate; bromine / 2.17 h / 90 - 110 °C 3.1: trichlorophosphate / toluene / 0.5 h / 97 °C 3.2: 5 h / 97 °C View Scheme

2-(p-chlorophenyl)-5-(trifluoromethyl)-pyrrole-3-carbonitrile (122454-23-3) → chlorfenapyr (122453-73-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic acid; sodium acetate; bromine / 2.17 h / 90 - 110 °C 2.1: sodium hydroxide / 0.33 h / 20 °C 2.2: 2 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1.1: acetic acid; sodium acetate; bromine / 2.17 h / 90 - 110 °C 2.1: trichlorophosphate / toluene / 0.5 h / 97 °C 2.2: 5 h / 97 °C View Scheme

4-diazo-2-tosyl-1,4-dihydroisoquinolin-3(2H)-one + chlorfenapyr (122453-73-0) → 2-(4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrol-3-yl)-4-tosyl-4,5-dihydrooxazolo[5,4-c]isoquinoline

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 35℃; Schlenk technique;	47%

chlorfenapyr (122453-73-0) → 2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile + 2-(4-chlorophenyl)-1-(ethoxymethyl)-4-fluoro-5-(trifluoromethyl)pyrrole-3-carbonitrile

Conditions	Yield
With tert.-butyl lithium; N-fluorobis(benzenesulfon)imide 1.) THF, pentane, -78 deg C, 0.5 h, 2.) THF, pentane, a) -78 deg C, 1 h, b) RT, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

Upstream product

• 122454-29-9 tralopyril 
• 3188-13-4 ethyl chloromethyl ether 
• 462-95-3 formaldehyde diethyl acetal 
• 6212-33-5 2-(4-Chlorophenyl)glycine 
• 122460-66-6 4-(p-chlorophenyl)-2-(trifluoromethyl)-1,3-oxazol-5-one 
• 122454-23-3 2-(p-chlorophenyl)-5-(trifluoromethyl)-pyrrole-3-carbonitrile 

Relevant academic research and scientific papers

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.

NOVEL CRYSTALLINE FORM OF CHLORFENAPYR, PROCESS FOR ITS PREPARATION AND USE

Provided herein are the crystalline form of chlorfenapyr of formula (I), the crystal preparation process, the analyses of the crystal through various analytical methods, using the crystal to prepare stable agrochemical formulation, and the use of various solvents towards the crystalline form preparation conditions.

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).

ACTIVE COMPOUND COMBINATIONS HAVING INSECTICIDAL AND ACARICIDAL PROPERTIES

The novel active compound combinations comprising a compound of the formula (I-1) or (I-2) and the active compounds (1) to (26) listed in the description have very good insecticidal and acaricidal properties.

Chemical uncouplers for the treatment of obesity

This invention relates to chemical uncouplers with a broader safety window making the use of them in treating obesity and, consequently, in the treatment of obesity related diseases and conditions such as atherosclerosis, hypertension, diabetes, especially type 2 diabetes (NIDDM (non-insulin dependent diabetes mellitus)), impaired glucose tolerance, dyslipidemia, coronary heart disease, gallbladder disease, osteoarthritis and various types of cancer such as endometrial, breast, prostate and colon cancers and the risk for premature death as well as other conditions, such as diseases and disorders, which conditions are improved by an increase in mitochondrial respiration, more attractive.

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.

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.