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MedKoo Cat#: 558532 | Name: Ethiprole
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ethiprole is a chiral phenylpyrazole insecticide. Specifically, it is used to used to control chewing and sucking insects in rice, fruit and vegetable crops.

Chemical Structure

Ethiprole
Ethiprole
CAS#181587-01-9

Theoretical Analysis

MedKoo Cat#: 558532

Name: Ethiprole

CAS#: 181587-01-9

Chemical Formula: C13H9Cl2F3N4OS

Exact Mass: 395.9800

Molecular Weight: 397.20

Elemental Analysis: C, 39.31; H, 2.28; Cl, 17.85; F, 14.35; N, 14.11; O, 4.03; S, 8.07

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
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Related CAS #
No Data
Synonym
Ethiprole; Kirappu; RAP 107382; RAP107382; RAP-107382;
IUPAC/Chemical Name
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(ethylsulfinyl)-1H-pyrazole-3-carbonitrile
InChi Key
FNELVJVBIYMIMC-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H9Cl2F3N4OS/c1-2-24(23)11-9(5-19)21-22(12(11)20)10-7(14)3-6(4-8(10)15)13(16,17)18/h3-4H,2,20H2,1H3
SMILES Code
N#CC1=NN(C2=C(Cl)C=C(C(F)(F)F)C=C2Cl)C(N)=C1S(CC)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 397.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Elzaki ME, Zhang W, Han Z. Cytochrome P450 CYP4DE1 and CYP6CW3v2 contribute to ethiprole resistance in Laodelphax striatellus (Fallén). Insect Mol Biol. 2015 Jun;24(3):368-76. doi: 10.1111/imb.12164. Epub 2015 Feb 18. PubMed PMID: 25693611. 2: Zhang Q, Shi H, Gao B, Tian M, Hua X, Wang M. Enantioseparation and determination of the chiral phenylpyrazole insecticide ethiprole in agricultural and environmental samples and its enantioselective degradation in soil. Sci Total Environ. 2016 Jan 15;542(Pt A):845-53. doi: 10.1016/j.scitotenv.2015.10.132. Epub 2015 Nov 8. PubMed PMID: 26556749. 3: Garrood WT, Zimmer CT, Gorman KJ, Nauen R, Bass C, Davies TG. Field-evolved resistance to imidacloprid and ethiprole in populations of brown planthopper Nilaparvata lugens collected from across South and East Asia. Pest Manag Sci. 2016 Jan;72(1):140-9. doi: 10.1002/ps.3980. Epub 2015 Feb 19. PubMed PMID: 25612154; PubMed Central PMCID: PMC4964955. 4: Caboni P, Sammelson RE, Casida JE. Phenylpyrazole insecticide photochemistry, metabolism, and GABAergic action: ethiprole compared with fipronil. J Agric Food Chem. 2003 Nov 19;51(24):7055-61. PubMed PMID: 14611171. 5: Zhao X, Ning Z, He Y, Shen J, Su J, Gao C, Zhu YC. Differential resistance and cross-resistance to three phenylpyrazole insecticides in the planthopper Nilaparvata lugens (Hemiptera: Delphacidae). J Econ Entomol. 2011 Aug;104(4):1364-8. PubMed PMID: 21882705. 6: Zhang X, Liao X, Mao K, Zhang K, Wan H, Li J. Insecticide resistance monitoring and correlation analysis of insecticides in field populations of the brown planthopper Nilaparvata lugens (stål) in China 2012-2014. Pestic Biochem Physiol. 2016 Sep;132:13-20. doi: 10.1016/j.pestbp.2015.10.003. Epub 2015 Oct 21. PubMed PMID: 27521908. 7: Arthur FH. Efficacy of ethiprole applied alone and in combination with conventional insecticides for protection of stored wheat and stored corn. J Econ Entomol. 2002 Dec;95(6):1314-8. PubMed PMID: 12539848. 8: Wang Y, Wu C, Cang T, Yang L, Yu W, Zhao X, Wang Q, Cai L. Toxicity risk of insecticides to the insect egg parasitoid Trichogramma evanescens Westwood (Hymenoptera: Trichogrammatidae). Pest Manag Sci. 2014 Mar;70(3):398-404. doi: 10.1002/ps.3571. Epub 2013 Jul 29. PubMed PMID: 23633188. 9: Garrood WT, Zimmer CT, Gutbrod O, Lüke B, Williamson MS, Bass C, Nauen R, Emyr Davies TG. Influence of the RDL A301S mutation in the brown planthopper Nilaparvata lugens on the activity of phenylpyrazole insecticides. Pestic Biochem Physiol. 2017 Oct;142:1-8. doi: 10.1016/j.pestbp.2017.01.007. Epub 2017 Jan 5. PubMed PMID: 29107231; PubMed Central PMCID: PMC5672059. 10: Hu M, Liu X, Wu X, Dong F, Xu J, Chen W, Zheng Y. Characterization of the fate and distribution of ethiprole in water-fish-sediment microcosm using a fugacity model. Sci Total Environ. 2017 Jan 15;576:696-704. doi: 10.1016/j.scitotenv.2016.10.087. Epub 2016 Oct 28. PubMed PMID: 27810756. 11: Tanaka T, Suzuki T, Inomata A. Reproductive and neurobehavioral effects of maternal exposure to ethiprole in F(1) -generation mice. Birth Defects Res. 2018 Feb 15;110(3):259-275. doi: 10.1002/bdr2.1162. Epub 2017 Nov 17. PubMed PMID: 29148216. 12: Paradis D, Bérail G, Bonmatin JM, Belzunces LP. Sensitive analytical methods for 22 relevant insecticides of 3 chemical families in honey by GC-MS/MS and LC-MS/MS. Anal Bioanal Chem. 2014 Jan;406(2):621-33. doi: 10.1007/s00216-013-7483-z. Epub 2013 Nov 21. PubMed PMID: 24253411. 13: Tanaka T, Inomata A. Reproductive and Neurobehavioral Effects of Ethiprole Administered to Mice in the Diet. Birth Defects Res. 2017 Nov 15;109(19):1568-1585. doi: 10.1002/bdr2.1092. Epub 2017 Aug 1. PubMed PMID: 28762667. 14: Takeuchi H, Endo N. Insecticide susceptibility of Nezara viridula (Heteroptera: Pentatomidae) and three other stink bug species composing a soybean pest complex in Japan. J Econ Entomol. 2012 Jun;105(3):1024-33. PubMed PMID: 22812144. 15: Li S, Wang P, Liu X, Wu X, Dong F, Xu J, Zheng Y. Polyoxymethylene passive samplers to assess the effectiveness of biochar by reducing the content of freely dissolved fipronil and ethiprole. Sci Total Environ. 2018 Jul 15;630:960-966. doi: 10.1016/j.scitotenv.2018.02.221. Epub 2018 Mar 7. PubMed PMID: 29554781. 16: Vidau C, Brunet JL, Badiou A, Belzunces LP. Phenylpyrazole insecticides induce cytotoxicity by altering mechanisms involved in cellular energy supply in the human epithelial cell model Caco-2. Toxicol In Vitro. 2009 Jun;23(4):589-97. doi: 10.1016/j.tiv.2009.01.017. Epub 2009 Feb 6. PubMed PMID: 19490841. 17: Gao J, Qu H, Zhang C, Li W, Wang P, Zhou Z. Direct chiral separations of the enantiomers of phenylpyrazole pesticides and the metabolites by HPLC. Chirality. 2017 Jan;29(1):19-25. doi: 10.1002/chir.22661. Epub 2016 Dec 21. PubMed PMID: 28000946. 18: Sheng CW, Casida JE, Durkin KA, Chen F, Han ZJ, Zhao CQ. Fiprole insecticide resistance of Laodelphax striatellus: electrophysiological and molecular docking characterization of A2'N RDL GABA receptors. Pest Manag Sci. 2018 May 2. doi: 10.1002/ps.5059. [Epub ahead of print] PubMed PMID: 29718557. 19: Zhao X, Wu C, Wang Y, Cang T, Chen L, Yu R, Wang Q. Assessment of toxicity risk of insecticides used in rice ecosystem on Trichogramma japonicum, an egg parasitoid of rice lepidopterans. J Econ Entomol. 2012 Feb;105(1):92-101. PubMed PMID: 22420260. 20: Zhao Q, Li Y, Xiong L, Wang Q. Design, synthesis and insecticidal activity of novel phenylpyrazoles containing a 2,2,2-trichloro-1-alkoxyethyl moiety. J Agric Food Chem. 2010 Apr 28;58(8):4992-8. doi: 10.1021/jf1001793. PubMed PMID: 20349960.