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Studies on herbicidal carbamoyltetrazolinone derivatives: Selection of fentrazamide
Author(s) -
GOTO TOSHIO,
ITO SEISHI,
YANAGI AKIHIKO,
WATANABE YUKIYOSHI,
YASUI KAZUOMI
Publication year - 2002
Publication title -
weed biology and management
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.351
H-Index - 36
eISSN - 1445-6664
pISSN - 1444-6162
DOI - 10.1046/j.1445-6664.2002.00042.x
Subject(s) - echinochloa , nitrogen atom , selectivity , alkyl , nitrogen , biology , echinochloa crus galli , oryza sativa , carboxamide , agronomy , medicinal chemistry , chemistry , organic chemistry , gene , weed , biochemistry , catalysis
1‐Phenyl‐5(4 H )‐4‐dialkylcarbamoyltetrazolinones represent a new class of herbicides that are active against barnyardgrass ( Echinochloa spp.) in paddy fields. To select the most favorable compound as a paddy herbicide, herbicidal activity and selectivity of the carbamoyltetrazolinone compounds to transplanted rice were determined in greenhouse tests. Higher herbicidal activities were associated with the compounds having a 2‐Cl‐ or 2‐Cl‐6‐Me‐substituted or an unsubstituted phenyl ring, and a combination of C 2–3 linear alkyl group and a C 4 branched‐chain alkyl or a C 5–6 cycloalkyl group on the nitrogen atom in the carbamoyl structure. In addition, the compounds carrying a total of seven to nine carbon atoms in the substituents on the carbamoyl nitrogen exhibited a good selectivity between barnyardgrass and transplanted rice plants. From the results of soil thick‐layer chromatography, the good crop compatibility of carbamoyltetrazolinones was correlated to the mobility of the compounds in paddy soil. The investigation resulted in the selection of an excellent compound, 4‐(2‐chlorophenyl)‐ N ‐cyclohexyl‐ N ‐ethyl‐4,5‐dihydro‐5‐oxo‐1 H ‐tetrazole‐1‐carboxamide (common name: fentrazamide), as a rice paddy herbicide for controlling barnyardgrass.