Synthesis and herbicidal activity of substituted pyrazole isothiocyanates

Molecules

Volumn 17, Issue 10, 2012, Pages 12187-12196

  Wu, Hua ^a   Feng, Jun Tao ^a   Lin, Kai Chun ^b   Zhang, Xing ^a  

^a NORTHWEST A F UNIVERSITY   (China)

^b Hubei Green Tiandi Bioengineering Co Ltd   (China)

Author keywords

Herbicidal activity; Isothiocyanates; Substituted pyrazoles; Synthesis

Indexed keywords

HERBICIDE; ISOTHIOCYANIC ACID DERIVATIVE; PYRAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; DRUG EFFECT; GROWTH, DEVELOPMENT AND AGING; SYNTHESIS; WEED;

HERBICIDES; ISOTHIOCYANATES; PLANT WEEDS; PYRAZOLES;

EID: 84868104645     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules171012187     Document Type: Article

References (23)

1. Du, X.H. Amide Thiourea and 1, 2, 4-Triazoles Synthesis and Plant Growth Regulating Activity. Ph.D. Dissertation, China Agricultural University, Beijing, China, 1997.
2. Wong, R.; Dolman, S.J. Isothiocyanates from Tosyl Chloride Mediated Decomposition of in situ Generated Dithiocarbamic Acid Salts. J. Org. Chem. 2007, 72, 3969-3971.
3. Munch, H.; Hansen, J.S.; Pittelkow, M.; Christensen, J.B.; Boas, U. A new efficient synthesis of isothiocyanates from amines using di-tert-butyl dicarbonate. Tetrahedron Lett. 2008, 49, 3117-3119.
4. Ono, H.; Adachi, K.; Fuke, Y.; Shinhara, K. Purification and structural analysis of substance in wassabi that suppress the growth of MKN-28 human stomach cancer cells. J. Jpn. Soc. Food Sci. 1996, 43, 1092-1097.
5. Murata, M.; Yamashita, N.; Inoue, S.; Kawanishi, S. Mechanism of oxidative DNA damage induced by carcinogenic allyl isothiocynate. Free Radic. Biol. Med. 2000, 28, 797-805.
6. Petersen, J.; Belz, R.; Walker, F.; Hurle, K. Weed Suppression by Release of Isothiocyanates from Turnip-Rape Mulch. Agron. J. 2001, 93, 37-43.
7. Norsworthy, J.K.; Brandenberger, L.; Burgos, N.R.; Riley, M. Weed suppression in Vigna unguiculata with a spring-seeded brassicaceae green manure. Crop Prot. 2005, 24, 441-447.
8. Haramoto, E.R.; Gallandt, E.R. Brassica cover cropping for weed management: A review. Renew. Agric. Food Syst. 2005, 19, 187-198.
9. Chen, H.S.; Li, Z.M.; Li, J.F. Synthesis of 2-Pyrazoyl-5-substituted-1, 3, 4-oxadiazoles and Their Biological Activities. Chem. J. Chin. Univ. 2000, 21, 1520-1523.
10. Zhang, K.S.; Mu, L.J.; Long, W.X. Synthesis and Preliminary Bio activity Studies of α-Pyrazyl-N-phenyl-α-aminophosphonates. Chem. J. Chin. Univ. 1999, 20, 741-743.
11. Zhao, W.G.; Chen, H.S.; Li, Z.M.; Han, Y.F.; Yan, H.; Lai, J.Y.; Wang, S.H. Synthesis of Pyrazolyl-heterocycles and Their Fungicidal Activities. Chin. J. Chem. 2001, 22, 939-942.
12. Okafa, I.; Okul, S. Pyrazole derivative, insecticidal or miticidal composition containing the same as the effective ingredient. U.S. Patent 4, 950, 668, 21 August 1990.
13. Hiromichi, I.; Takeshi, M.; Toshiji, O.; Toshiki, N.; Masakazu, T.; Hirokazu, Y.; Masako, Y. Triazole derivative and herbicide. Hokko Chem. Ind. JP Patent 1993-163254, 29 June 1993.
14. Zhao, W.G.; Cao, Y.B.; Li, Z.M.; Gao, F.W.; Wang, S.H.; Wang, J.G. Synthesis and Biological Activity of 1-Sulfonyl-3, 5-diamino-1H-Pyrazole Derivatives. Chin. J. Appl. Chem. 2001, 18, 423-427.
15. Fuchs, U.; Erdelen, C. Substituted pyrazoline derivatives. EP Patent 0679644, 11 November 1995.
16. Yoshikawa, Y.; Tomiya, K.; Kitajima, T.; Katsuta, H.; Takahashi, O.; Inami, S. Yanase, Y.; Tomura, N.; Kishi, J.; Kawasima, H. Substituted thiopene derivative and plant disease control agent comprising the same as active ingredient. EP Patent 0841336, 9 February 1999.
17. Hatton, L.R.; Parnell, E.W.; Roberts, D.A. N-Phenylpyrazole derivatives. U.S. Patent 4, 496, 390, 29 January 1985.
18. Hatton, L.R.; Parnell, E.W.; Roberts, D.A. 4- Trifluoromethylphenylhydrazinomethylene malononitriles. U.S. Patent 4, 541, 963, 17 September 1985.
19. Hatton, L.R.; Buntain, I.G.; Hawkins, D.W.; Parnell, E.W.; Pearson, C.J.; Roberts, D.A. Derivatives of N-phenylpyrazoles. EP Patent 0967206, 29 June 1999.
20. Hatton, L.R.; Buntain, I.G.; Hawkins, D.W.; Parnell, E.W.; Pearson, C.J.; Roberts, D.A. Derivatives of N-phenylpyrazoles. EP Patent 295117, 20 August 1996.
21. Zhao, W.G.; Wang, S.H.; Wang, W.Y. Improved synthesis of disulfide acetal chemical reagents. Chem. Reag. 2000, 22, 376-377.
22. Liu, H.; Wang, H.Q.; Liu, Z.J. Synthesis and herbicidal activity of novel pyrazolo[3, 4-d]pyrimidin-4-one derivatives containing aryloxyphenoxypropionate moieties. Bioorg. Med. Chem. Lett. 2007, 17, 2203-2209.
23. Zou, X.W. Studies on Synthesis and Biological Activities of Six Phenmethyl Urea Compounds. M.Sc. Dissertation, Huazhong Agricultural University, Wuhan, China, 2007.