Transformations of chlorodibromomethyl-4-chlorophenyl sulfone into new compounds with potential pesticidal activity

• Autorzy: Ochal Z. , Wójcicki J.
• Języki publikacji: EN

Abstrakty

EN

The synthesis of chlorodibromomethyl-4-cfilorophcnyl sulfone derivatives as new potential pesticides is reported. The title sulfonc was obtained starting from chlorobenzene, its chlorosulfonation, reduction to the sulfinyl salt, which was transformed with bromofbrm or diehloroacetic acid natrium salt to dibromo-mcthyl-4-ch!orophenylsulfonc 4, or chloromcthyl-4-clilorophcnylsulfone 5. Sulfone 4 was chlorinated by hypohalite and sulfone 5 was brominated by bromine chloride or hypobromite to a final product 6. Chlorodibromomethyl-4-chiorophenyl sulfone was nitrated and then subjected to the SNAr reaction with amines and hydrazine to give 2-nitroaniline and 2-nitrophenylhydra7ioe derivatives. The last one was rransfonncd into hydrazonc, semicarbazide and tiosemicarbazidc derivatives.

Słowa kluczowe

EN

chlorodibromomethylphenyl sulfone derivatives; SNAr reactions; 2-nitroaniline and phenylhydrazone derivatives; pesticides

PL

sulfon; pochodne sulfonu; reakcja SNAr; nitroanilina; pochodne nitroaniliny; pochodne fenylohydrazonu; pestycydy

• Wydawca: Centrum Materiałów Polimerowych i Węglowych PAN
• Czasopismo: Polish Journal of Applied Chemistry
• Rocznik: 2007
• Tom: Vol. 51, nr 1-2
• Strony: 29--41
• Opis fizyczny: Bibliogr. 18 poz.

Twórcy

autor

Ochal Z.

autor

Wójcicki J.

• Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, PL. 00-664 Warsaw, Poland,

Bibliografia

• [1] US Patent 2,484489, (1949); Chem. Abstr., 445387e (1950).
• [2] Japan Patent 7 594.126, (1975); Chem. Abstr., 84, 13509g (1976).
• [3] US Patent 3.557.353, (1972); Chem. Abstr., 77, 151671k; (1972).
• [4] US Patent 3.927.110, (1975); Chem. Abstr., 84, 135301d; (1976).
• [5] US Patent 4.185.120, (1980); Chem. Abstr., 92, 203585s; (1980).
• [6] Japan Patent 60.239.402, (1985); Chem. Abstr., 104, 125071w; (1986).
• [7] Japan Patent 63.243.067, (1988); Chem. Abstr., 110, 212359p (1989).
• [8] Japan Patent 58.128.305, (1983); Chem. Abstr., 99, 117868z (1983).
• [9] US Patent 4.247.559, (1981); Chem. Abstr., 95, 24808g (1981).
• [10] Japan Patent 54.090.145, (1979); Chem. Abstr., 92, 6236c (1980).
• [11] Z. ECKSTEIN, M. ZAWISTOWSKA, D. PALUT and E. POLUBIEC, Przem. Chem., 45(6), 314-320 (1966).
• [12] Z. OCHAL and R. KAMIŃSKI, Pol. J. Appl. Chem., 49, 215-225 (2005).
• [13] PI Patent 172321 B1 (1997) Chem. Abstr., 128, P75189p (1998).
• [14] Z. EJMOCKI, Z. ECKSTEIN, E. GRADON, Z. OCHAL, D. RUSEK and B. STAWSKA, Pol. J. Chem., 57, 1037-1042(1983).
• [15] W. MLDDELBOS, J. STRATING and B. ZWANENBURG, Tetrahedron Lett., 351 (1971).
• [16] A. MIZERSKI, Z. OCHAL, S. ZAŁĘCKI and Z. EJMOCKI, Pesticides, (1,2), 29-41 (2001).
• [17] Z. EJMOCKI, Z. OCHAL, T. FIRLĄG and S. ZAŁĘCKI, Pesticides, (4), 5-19 (1998).
• [18] F.G. BORDWELL and W.T. BRANNEN, J. Am. Chem. Soc., 86, 4645-4652 (1964).