Synthesis and characterization of tributyltin(IV) complexes of 2-[(E)-2-(3-formyl-4-hydroxyphenyl)-1-diazenyl]benzoic acid and 4-[((E)-1-{2-hydroxy-5-[(E)-2-(2-carboxyphenyl)-1-diazenyl]phenyl}methylidene)amino]aryls – crystal structures of polymeric (Bu3Sn[O2CC6H4{NN(C6H3-4-OH-5-CHO)}-o])n and (Bu3Sn[O2CC6H4{NN(C6H3-4-OH(C(H)NC6H4Cl-4))}-o])n – toxicity studies on the second instar of Aedes aegypti mosquito larvae

Abstract

The tri-n-butyltin(IV) complexes of 2-[(E)-2-(3-formyl-4-hydroxyphenyl)-1-diazenyl]benzoic acid and 4-[((E)-1-{2-hydroxy-5-[(E)-2-(2-carboxyphenyl)-1-diazenyl]phenyl}methylidene)amino]aryls (aryls = 4-CH 3 , 4-Br, 4-Cl, 4-OCH 3 ) have been synthesized and characterized by 1 H, 13 C, 119 Sn NMR, IR and 119m Sn Mö ssbauer spectroscopic techniques in combination with elemental analysis. The crystal structures of two compounds, (Bu 3 Sn[O 2 CC 6 H 4 {N@N(C 6 H 3 -4-OH-5-CHO)}-o]) n and (Bu 3 Sn[O 2 CC 6 H 4 -{N@N(C 6 H 3 -4-OH(C(H)@NC 6 H 4 Cl-4))}-o]) n , are reported.The crystallographic and 119 Sn Mö ssbauer data both indicate that the tributyltin complexes form single-stranded polymeric structures in which the carboxylate O atoms of each aryl ligand bridge two Sn atoms. The Sn atoms have a slighly distorted trigonal bipyramidal coordination geometry with equatorial butyl groups and carboxylate O atoms occupying axial positions. The 119 Sn NMR spectroscopic data and the 1 J( 13 C-119/117 Sn) coupling constant indicate a tetrahedral coordination geometry in non-coordinating solvents. The results of a toxicity study of a tributyltin compound on the second larval instar of Aedes aegypti mosquito larvae are reported.

Electrospray ionization mass spectrometry of tributyltin(IV) complexes and their larvicidal activity on mosquito larvae: crystal and molecular structure of polymeric (Bu3Sn[O2CC6H4{NN(C6H3-4-OH(C(H)NC6H4OCH3-4))}-o])n

“…9 ESI mass spectra, both in the positive-and negativeion modes, were measured using acetonitrile solutions of complexes 1-5 and the results are summarized in Tables 1-5. The interpretation of the mass spectra is based on previous studies on ESI-MS measurements of organotin compounds.…”

“…4) (4), which were reported earlier. 9 The asymmetric unit contains two repeats of the principal chemical unit and the structure is built from adjacent SnBu 3 moieties bridged by the two carboxylate oxygen atoms of a single aryl ligand, with the pattern then continuing indefinitely, as illustrated in Fig. 5.…”

“…7 Consequently, a series of azo-butyltin compounds, viz. tributyltin 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoates and tributyltin 2-[(E)-2-(3-formyl-4-hydroxyphenyl)-1-diazenyl]benzoate have been investigated and have shown moderate 8 and better 9 activities respectively. In view of the overall effectiveness of the tributyltins, and in search of better candidates for the control of various mosquito larvae, the present investigation evaluates the toxicity of a series of tributyltin azo-Schiff base complexes derived from 4 (5), has been described in an earlier report, 9 along with the characterization of the compounds by carbon, hydrogen and nitrogen analyses, IR, 1 H, 13 C and 119 Sn NMR, and 119 Sn Mössbauer spectroscopy.…”

“…tributyltin 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoates and tributyltin 2-[(E)-2-(3-formyl-4-hydroxyphenyl)-1-diazenyl]benzoate have been investigated and have shown moderate 8 and better 9 activities respectively. In view of the overall effectiveness of the tributyltins, and in search of better candidates for the control of various mosquito larvae, the present investigation evaluates the toxicity of a series of tributyltin azo-Schiff base complexes derived from 4 (5), has been described in an earlier report, 9 along with the characterization of the compounds by carbon, hydrogen and nitrogen analyses, IR, 1 H, 13 C and 119 Sn NMR, and 119 Sn Mössbauer spectroscopy. The crystal structures of complexes 1 and 4 were also reported, 9 and together with the 119 Sn Mössbauer data revealed that the tributyltin complexes form single-stranded polymeric structures, in which the carboxylate oxygen atoms of each aryl ligand bridge two tin atoms and the tin atoms have a slightly distorted trigonal bipyramidal coordination geometry.…”

“…In view of the overall effectiveness of the tributyltins, and in search of better candidates for the control of various mosquito larvae, the present investigation evaluates the toxicity of a series of tributyltin azo-Schiff base complexes derived from 4 (5), has been described in an earlier report, 9 along with the characterization of the compounds by carbon, hydrogen and nitrogen analyses, IR, 1 H, 13 C and 119 Sn NMR, and 119 Sn Mössbauer spectroscopy. The crystal structures of complexes 1 and 4 were also reported, 9 and together with the 119 Sn Mössbauer data revealed that the tributyltin complexes form single-stranded polymeric structures, in which the carboxylate oxygen atoms of each aryl ligand bridge two tin atoms and the tin atoms have a slightly distorted trigonal bipyramidal coordination geometry. In addition to the results of the toxicity studies, the current report now extends the previous work by describing the crystal structure of complex 5 and the results of an investigation by electrospray ionization mass spectrometry (ESI-MS).…”