Synthesis and herbicidal activities of N-[4-Cyano-2-fluoro-5-(substituted)phenyl]-3,4,5,6-tetrahydrophthalimide

N-[4-Cyano-2-fluoro-5-(substituted)phenyl]-3,4,5,6-tetrahydrophthalimide 유도체의 합성과 제초활성

  • 류재욱 (한국화학연구원 생물화학부) ;
  • 정근회 (한국화학연구원 생물화학부) ;
  • 고영관 (한국화학연구원 생물화학부) ;
  • 우재춘 (한국화학연구원 생물화학부) ;
  • 구동완 (한국화학연구원 생물화학부) ;
  • 김태준 (한국화학연구원 생물화학부) ;
  • 최정섭 (한국화학연구원 생물화학부) ;
  • 박채현 (동부한농(주) 농업기술연구소) ;
  • 김대황 (한국화학연구원 생물화학부)
  • Published : 2005.03.31

Abstract

A series of N-[4-cyano-2-fluoro-5-(2-pyrimidinyloxy, 2-benzyloxy or 2-pyridinyloxy)phenyl]-3,4,5,6-tetrahydrophthalimides was synthesized, and the herbicidal activities of those deivatives were evaluated through pre- and post-emergence application under upland conditions in a greenhouse. The results showed that most compounds resulted in stronger herbicidal activity on broadleaf weeds than on grass weeds and higher through post-emergence than pre-emergence application. The N-[(4-cyano-2-fluoro-5-(2-pyrimidinyloxy) phenyl]-3,4,5,6-tetrahydrophthalimide showed the best weed control efficacy and marginal corn safety at a rate of 60 g/ha through pre-emergence application.

N-[4-Cyano-2-fluoro-5-(2-pyrimidinyloxy, 2-benzyloxy 혹은 2-pyridinyloxy)phenyl]-3,4,5,6-tetrahyophtha-limide 유도체를 합성하였고, 밭 조건에서 토양 및 경엽처리후의 제초활성을 온실에서 조사하였다. 이 화합물들의 제초효과는 토양처리보다 경엽처리에서 강하였으며, 광엽 잡초에 대한 제초활성이 화본과 잡초에 대한 활성보다 우수하였다. N-[(4-cyano-2-fluoro-5-(2-pyrimidinyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide가 가장 강한 제초활성을 나타내었을 뿐 만아니라 60 g/ha 농도의 토양처리에서 옥수수에 비교적 안전하였다.

Keywords

References

  1. Gheodoridis, G. (1997) Structure-activity relationship of herbicidal aryltriazolinones. Pesticide Science 50:283-290 https://doi.org/10.1002/(SICI)1096-9063(199708)50:4<283::AID-PS600>3.0.CO;2-L
  2. Hirai, K. (1999) Structural evolution and synthesis of diphenyl ethers, cyclic imides and related compounds. pp.24-37, In Peroxidising herbicides (ed. Boger, P. and K. Wakanayashi), Springer, Berlin
  3. Hirai, K., A. Uchida and R. Ohno (2002) Major synthetic routes for modern herbicide classes and agrochemical characteristics, pp.255-278, In Herbicide classes in development (ed. Boger, P. and K. Wakanayashi), Springer, Berlin
  4. Hiratsuka, M., N. Hirata and K. Saito (1991) Preparation of pyrimidine derivatives as wide spectrum herbicides, JP 03240787
  5. Ichiki, T. (1986) Process for producing tetrahydrophthalimides, US 4563535
  6. Lyga, J. W., R. M. Patera, G. Theodoridis, B. P. Halling, F. W. Hotzman and M. J. Plummer (1991) Synthesis and quantitative structure-activity relationships of herbicidal N-(2-fluoro-5-methoxyphenyl)-3,4,5,6-tetrahydrophthalimides. J. Agric. Food Chem. 39: 1667-1673 https://doi.org/10.1021/jf00009a025
  7. Theodoridis, G. (1989) Preparation of N-phenyl tetrahydrophthalimides as herbicides, US 4816065
  8. Theodoridis, G., T. B. Bahr, S. Crawford, B. Dugan, W. H. Hotzman, L. L. Maravetz, S. Sehgel and D. P. Suarez (2002) Synthesis and structure-activity of novel 3-(4,6-substituted benzoheterocydyl)uracil herbicides, pp. 96-107, In Synthesis and chemistry of agrochemicals VI, ACS symposium series 800, (ed. Baker, D. R., J. G. Fenyes, G. P. Laahm, T. P. Selby and T. M. Stevenson), ACS, Washington
  9. 김대황, 정근회, 장해성, 고영관, 류재욱, 우재춘, 구동완, 김태준, 최정섭 (2003) 제초활성을 가지는 3,4,5,6-테트라히드로프탈이미드계 화합물. 대한민국 특허:03-69321
  10. 류재욱, 김병철, 정근회, 장해성, 고영관, 우재춘, 구동완, 김대황 (2002) 신규 Sulfonylurea 제초제의 합성과 제초특성. 농약과학회지 9(4):320-323
  11. 조광연 (1998) 신농약 효능검사 및 기반기술연구, p.901, 과학기술부 선도기술개발사업 2단계 최종보고서