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122453-73-0

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122453-73-0 Usage

Description

Different sources of media describe the Description of 122453-73-0 differently. You can refer to the following data:
1. Chlorfenapyr is a broad spectrum pesticide which is not approved for use in the EU, and only approved for limited applications in the US (applications for ornamental plants in greenhouses). It was originally rejected for FDA approval due to avian and aquatic toxicity. Data on human toxicity is still scarce, but it has moderate mammalian toxicity when taken orally, causing vacuolation of the nervous system in mice and rats. It is not persistent in ecosystems, and has low aqueous solubility. Chlorfenapyr can also be used as an insect-proofing agent in wool, and has been investigated for applications in malaria control.
2. Chlorfenapyr is a pyrrole pro-insecticide that is metabolized in vivo into CL 303268 by mixed function oxidases. Chlorfenapyr increases respiratory activity in German cockroaches when used at concentrations ranging from 1 to 10 μg per insect but has no effect on respiration in Sf9 cells when used at concentrations ranging from 1 to 100 μM and does not affect respiration in isolated rat liver mitochondria up to a concentration of 10 μM. Chlorfenapyr is active against a variety of insects including those susceptible and resistant to pyrethroid and organophosphate insecticides, including horn flies (H. irritans) as well as A. culicifacies and A. stephensi mosquitos that carry malaria (LC50s = 2-2.39% suspension impregnated on paper). Chlorfenapyr is lethal to rats with LD50 values of 441 and 1,152 mg/kg for male and female rats, respectively. Formulations containing chlorfenapyr have been used to control termites and in agriculture to control various insects.

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

Check Digit Verification of cas no

The CAS Registry Mumber 122453-73-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,2,4,5 and 3 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 122453-73:
(8*1)+(7*2)+(6*2)+(5*4)+(4*5)+(3*3)+(2*7)+(1*3)=100
100 % 10 = 0
So 122453-73-0 is a valid CAS Registry Number.
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

122453-73-0 Well-known Company Product Price

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  • Sigma-Aldrich

  • (37913)  Chlorfenapyr  PESTANAL®, analytical standard

  • 122453-73-0

  • 37913-100MG-R

  • 780.39CNY

  • Detail

122453-73-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name chlorfenapyr

1.2 Other means of identification

Product number -
Other names 4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethyl-1H-pyrrole-3-carbonitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:122453-73-0 SDS

122453-73-0Synthetic route

tralopyril
122454-29-9

tralopyril

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

chlorfenapyr
122453-73-0

chlorfenapyr

Conditions
ConditionsYield
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

formaldehyde diethyl acetal

tralopyril
122454-29-9

tralopyril

chlorfenapyr
122453-73-0

chlorfenapyr

Conditions
ConditionsYield
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]

dimethylformamide [DMF]

formaldehyde diethyl acetal
462-95-3

formaldehyde diethyl acetal

tralopyril
122454-29-9

tralopyril

chlorfenapyr
122453-73-0

chlorfenapyr

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In water; toluene
4-bromo-1-(chloromethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

4-bromo-1-(chloromethyl)-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

chlorfenapyr
122453-73-0

chlorfenapyr

Conditions
ConditionsYield
With sodium ethanolate In ethanol
2-(4-Chlorophenyl)glycine
6212-33-5

2-(4-Chlorophenyl)glycine

chlorfenapyr
122453-73-0

chlorfenapyr

Conditions
ConditionsYield
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

4-(p-chlorophenyl)-2-(trifluoromethyl)-1,3-oxazol-5-one

chlorfenapyr
122453-73-0

chlorfenapyr

Conditions
ConditionsYield
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

2-(p-chlorophenyl)-5-(trifluoromethyl)-pyrrole-3-carbonitrile

chlorfenapyr
122453-73-0

chlorfenapyr

Conditions
ConditionsYield
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

4-diazo-2-tosyl-1,4-dihydroisoquinolin-3(2H)-one

chlorfenapyr
122453-73-0

chlorfenapyr

2-(4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrol-3-yl)-4-tosyl-4,5-dihydrooxazolo[5,4-c]isoquinoline

2-(4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrol-3-yl)-4-tosyl-4,5-dihydrooxazolo[5,4-c]isoquinoline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 35℃; Schlenk technique;47%
chlorfenapyr
122453-73-0

chlorfenapyr

A

2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

B

2-(4-chlorophenyl)-1-(ethoxymethyl)-4-fluoro-5-(trifluoromethyl)pyrrole-3-carbonitrile

2-(4-chlorophenyl)-1-(ethoxymethyl)-4-fluoro-5-(trifluoromethyl)pyrrole-3-carbonitrile

Conditions
ConditionsYield
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;

122453-73-0Downstream Products

122453-73-0Relevant articles and documents

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

Dai, Jianrong,Feng, Bainian,Qu, Guoli,Xing, Yuntian,Yao, Jiakai

, (2021/10/01)

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 biomphalarid snails

-

, (2019/01/08)

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

-

Page/Page column 15, (2018/10/19)

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).

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