Abstract
The title compound, C12H4Cl2F6N4OS {systematic name: 5-amino-1-[2,6-di-chloro-4-(tri-fluoro-meth-yl)phen-yl]-4-[(tri-fluoro-methane)sulfinyl]-1H-pyrazole-3-carbo-nitrile}, is a member of the phenyl-pyrazole group of acaricides, and one of the phenyl-pyrazole group of insecticides. The dihedral angle between the planes of the pyrazole and benzene rings is 89.03 (9)°. The fluorine atoms of the tri-fluoro-methyl substituent on the benzene ring are disordered over two sets of sites, with occupancy ratios 0.620 (15):0.380 (15). In the crystal, C-N⋯π inter-actions [N⋯ring centroid = 3.607 (4) Å] together with N-H⋯N and C-H⋯F hydrogen bonds form a looped chain structure along [10[Formula: see text]]. Finally, N-H⋯O hydrogen bonds and C-Cl⋯π inter-actions [Cl⋯ring centroid = 3.5159 (16) Å] generate a three-dimensional structure. Additionally, there are a short inter-molecular F⋯ F contacts present.
Highlights
The title compound, C12H4Cl2F6N4OS {systematic name: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethane)sulfinyl]-1H-pyrazole3-carbonitrile}, is a member of the phenylpyrazole group of acaricides, and one of the phenylpyrazole group of insecticides
Fipronil is an insecticide that belongs to the phenylpyrazole group
The toxicity of fipronil is attributed to its ability to act at the GABA receptor as a non-competitive inhibitor of the GABA-gated chloride channels of neurons in the central nervous system
Summary
Fipronil is an insecticide that belongs to the phenylpyrazole group. Fipronil contains a trifluoromethylsulfinyl substituent that is not present in any other agrochemicals and this is thought to contribute to its remarkable potency in the field (Hainzl & Casida, 1996). It is a highly effective and broad-spectrum insecticide against piercing–sucking, contact and chewing pests and is widely used to control many species of soil and foliar insects on various crops including rice, vegetables and fruits (Kaur et al, 2015). H atoms are shown as small spheres of arbitrary radius
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More From: Acta crystallographica. Section E, Crystallographic communications
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