120068-56-6

Basic information

• Product Name: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-1H-pyrazole-3-carbonitrile
• Synonyms: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-1H-pyrazole-3-carbonitrile
• CAS NO: 120068-56-6
• Molecular Weight: 381.208
• Mol File: 120068-56-6.mol

Chemical Properties

• CAS DataBase Reference: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-1H-pyrazole-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-1H-pyrazole-3-carbonitrile(120068-56-6)
• EPA Substance Registry System: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-1H-pyrazole-3-carbonitrile(120068-56-6)

Safety Data

• Hazardous Substances Data: 120068-56-6(Hazardous Substances Data)

Upstream product

• 181587-01-9 ethiprole 
• 74-96-4 ethyl bromide 
• 130755-46-3 4,4'-dithiobis [5-amino-3-cyano-1-{2,6-dichloro-4-(trifluoromethyl)phenyl}-1H-pyrazole] 
• 24279-39-8 2,6-dichloro-4-(trifluoromethyl)aniline 
• 120068-79-3 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole 

Downstream Products

• 181587-01-9 ethiprole 
• 209966-76-7 5-bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-1H-pyrazole-3-carbonitrile 
• 209965-86-6 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-ethylthio-1H-pyrazole-3-carboximidamide 
• 251544-24-8 5-amino-4-ethylthio-l-(2,6-dichloro-4-trifluoro-methylphenyl)-3-thiocarbamoyl-pyrazole 
• 120068-68-0 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]4(ethylsulfonyl)-1H-pyrazole-3-carbonitrile 
• 1222566-09-7 5-(2,2,2-trichloroethylideneamino)-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylsulfenylpyrazole 
• 1222566-19-9 C₁₇H₁₃Cl₆F₃N₄OS 
• 1222566-27-9 C₁₆H₁₂Cl₅F₃N₄O₂S 
• 1222566-28-0 C₁₇H₁₄Cl₅F₃N₄O₂S 
• 1222566-29-1 C₁₈H₁₆Cl₅F₃N₄O₂S 
• 1222566-30-4 C₁₇H₁₃Cl₅F₄N₄O₂S 
• 1222566-31-5 C₁₇H₁₃Cl₆F₃N₄O₂S 
• 1222566-15-5 C₁₆H₁₂Cl₅F₃N₄OS 
• 1222566-16-6 C₁₇H₁₄Cl₅F₃N₄OS 

Relevant articles and documents

Design, synthesis and insecticidal activity of novel phenylpyrazoles containing a 2,2,2-trichloro-1-alkoxyethyl moiety

A series of novel phenylpyrazoles containing a 2,2,2-trichloro-1- alkoxyethyl moiety were designed and synthesized via the key intermediate 5-trichloroethylideneimino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl) -4-alkylsulfenylpyrazole (5). The addition reaction of the imine 5 was closely related with the nature of the alcohol. The target compounds were confirmed by 1H NMR and elemental analysis. The results of bioassays indicated that the target compounds possessed excellent activities against a broad spectrum of insects such as bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens) and diamondback moth (Plutella xylostella). Especially, the foliar contact activity against bean aphid of compound 7h at 2.5 mg kg -1 was 89%, the larvacidal activity against mosquito of compound 6c at 2.5 μg kg-1 was 100%, the activity against diamondback moth of compound 7a at 5 mg kg-1 was 87%, and all of these activities were much higher than the contrast ethiprole. The results of insecticidal activities showed that the two pairs of enantiomers 7d-1 and 7d-2 gave activities without distinctive difference, and it was the similar situation for 7e-1 and 7e-2. Interestingly, the target compounds exhibited high selectivity between diamondback moth and oriental armyworm, both of which are of the order Lepidoptera. The 2,2,2-trichloro-1-alkoxyethyl moiety was essential for high insecticidal activities.

A convenient conversion of pyrazolyl disulfide to sulfides by sodium dithionite and synthesis of sulfoxides

Indirectly introduce trifluoromethylthio-, alkylthio-, and trifluoromethylsulfinyl to pyrazole ring by a convenient reaction of a pyrazolyl disulfide with F3CBr and alkyl halides in the presence of sodium dithionite at room temperature. Followed by selective oxidation with H2O2 or trichloroisocyanuric acid (TCCA) to give trifluoromethylsulfenyl phenylpyrazole, alkylsulfenyl phenylpyazole, trifluoromethylsulfinyl phenylpyrazole 4a (a highly efficient insecticide named fipronil) and ethylsulfinyl phenylpyrazole 4c derivatives, respectively.

Phenylpyrazole Insecticide Photochemistry, Metabolism, and GABAergic Action: Ethiprole Compared with Fipronil

Ethiprole differs from fipronil, the major phenylpyrazole insecticide, only in an ethylsulfinyl substituent replacing the trifluoromethylsulfinyl moiety. This study compares their photochemistry, metabolism, action at the γ-aminobutyric acid (GABA) receptor, and insecticidal potency. On exposure to sunlight as a thin film, ethiprole undergoes oxidation (major), reduction, and desethylsulfinylation but not desulfinylation whereas the major photoreaction for fipronil is desulfinylation. Metabolic sulfone formation is more rapid with ethiprole than fipronil in human expressed CYP3A4 in vitro and mouse brain and liver in vivo. High biological activity is observed for the sulfide, sulfoxide, sulfone, and desulfinyl derivatives in both the ethiprole and the fipronil series in GABA receptor assays (human recombinant β3 homomer and house fly head membranes) with [3H]EBOB and in topical toxicity to house flies with and without the P450-inhibiting synergist piperonyl butoxide. On an overall basis, the ethiprole series is very similar in potency to the fipronil series.

Derivatives of N-phenylpyrazoles

N-Phenylpyrazole derivatives of the formula: STR1 wherein R1 represents cyano, nitro, halogen, acetyl or formyl; R2 represents R5 SO2, R5 SO or R5 S in which R5 is optionally halogen substituted alkyl, alkenyl or alkynyl; R3 represents a hydrogen atom or a group NR6 R7 wherein R6 and R7 each represent hydrogen, alkyl, alkenylalkyl, alkynylalkyl, formyl, optionally halogen substituted alkanoyl, optionally halogen substituted alkoxycarbonyl, or alkoxymethyleneamino, halogen, or R6 and R7 together form a cyclic imide and R4 represents a substituted phenyl group possess arthropodicidal, plant nematocidal, anthelmintic and anti-protozoal properties; their preparation, compositions containing them and their use are described.

Derivatives of N-phenylpyrazoles

N-Phenylpyrazole derivatives of the formula: wherein R1 represents cyano, nitro, halogen, acetyl or formyl:, R2 represents R5SO2, R5SO or R5S in which R5 is optionally halogen substituted alkyl, alkenyl or alkynyl;, R3 represents a hydrogen atom or a group NR6R7 wherein R6 and R7 each represent hydrogen, alkyl, alkenylalkyl, alkynylalkyl, formyl, optionally halogen substituted alkanoyl, optionally halogen substituted alkoxycarbonyl, or alkoxymethyleneamino, halogen, or R6 and R7 together form a cyclic imide and R4 represents a substituted phenyl group possess arthropodicidal, plant nematocidal, anthelmintic and anti-protozoal properties; their preparation, compositions containing them and their use are described.