Amino- and urea-substituted thiazoles inhibit photosynthetic electron transfer.
Amino- and urea-substituted thiazoles exhibited in vivo herbicidal activity on duckweed (Lemna paucicostata Hegelm. strain 6746) cultures and appeared to act via inhibition of photosynthetic electron transport system. A small number of the thiazole derivatives tested were active but only at relatively high concentrations. The most active structures were the amino-substituted thiazoles with isopropyl and n-butyl side chains and the urea-substituted thiazole with p-chlorophenyl side chain. Decreasing the length of the side chain had a negative effect on the PSII inhibitory activity. The urea-substituted series was as a group less active than the amino series, and the free acid series had no biological activity. The most active compounds competed for the same binding site as atrazine on PSII. Computer modeling highlighted the structural similarities between some of the thiazoles and the commercial herbicides diuron and atrazine.
Dayan
F E
FE
USDA-ARS Natural Products Utilization Research Unit, University, Mississippi 38677, USA. fdayan@ag.gov
Vincent
A C
AC
Romagni
J G
JG
Allen
S N
SN
Duke
S O
SO
Duke
M V
MV
Bowling
J J
JJ
Zjawiony
J K
JK
D000588:Amines / Q000737:chemistry; D004579:Electron Transport; D006540:Herbicides / Q000737:chemistry / Q000494:pharmacology*; D019684:Magnoliopsida / Q000187:drug effects / Q000378:metabolism*; D015394:Molecular Structure; D010788:Photosynthesis / Q000187:drug effects*; D013844:Thiazoles / Q000737:chemistry / Q000494:pharmacology*; D014508:Urea / Q000737:chemistry
D000588:Amines; D006540:Herbicides; D013844:Thiazoles; D014508:Urea