Peroxidizing Phytotoxicities of 1, 2-Dialkyl-1, 2, 4-triazolidines and 3, 4-Dialkyl-1, 3, 4-thiadiazolidines

Abstract

General features of peroxidizing compounds are protoporphyrinogen-IX oxidase (Protox) inhibition, light-induced ethane formation, decreased chlorophyll content, growth inhibition of Scenedesmus acutus and root-growth inhibition of Echinochloa utilis. The first two parameters can be conveniently measured in a peroxidizing assay. The two parameters of peroxidizing phytotoxicities were measured with two series of compounds, i.e. 4-(4-bromophenyl)-1, 2-dialkyl (or polymethylene)-1, 2, 4-triazolidines and 5-(4-bromophenylimino)-3, 4-dialkyl (or polymethylene)-1, 3, 4-thiadiazolidines.The order of peroxidizing activity among the 4-(4-bromophenyl)-1, 2-dialkyl (or polymethylene)-5-thioxo-1, 2, 4-thiazolidin-3-ones was as follows: 1, 2-tetramethylene analogue > 1, 2-trimethylene analogue > 1, 2-pentamethylene analogue> 1, 2-dimethyl analogue> 1, 2-dimethyl analogue> 1, 2-dipropyl analogue > 4-(4-bromophenyl)-5-thioxo-1, 2, 4-triazolidin-3-one.The similar activity order was obtained also in the series of other 4-(4-bromophenyl)-1, 2-dialkyl (or polymethylene)-1, 2, 4-triazolidine-3, 5-diones (or dithiones) and 5-(4-bromophenylimino)-3, 4-dialkyl (or polymethylene)-l, 3, 4-thiadiazolidin-2-ones (or thiones). Furthermore, a structure-activity study revealed that the Protox inhibition by 4-(4-bromophenyl)-1, 2-dialkyl (or polymethylene)-5-thioxo-1, 2, 4-triazolidin-3-ones correlated well with the molecular size of compound.

3D-QSARs of Herbicidal 2-N-Phenylisoindolin-1-one Analogues as a New Class of Potent Inhibitors of Protox

“…[2][3][4][5][6] Especially, the study for the change of heterocyclic group is actively working. 7 The common ones of eight types in hererocyclic group are cyclopentane, tetrahydrophthalimide and bicyclic five-membered heterocyclic analogues.…”

Synthesis and Herbicidal Activity of 2-(7-Fluoro-3-oxo- 3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)isoindoline-1,3-diones

“…Thousands of active compounds exhibiting this mode of action have been synthesized (1)(2)(3)(4)(5). On the basis of their chemical structures, these compounds can be classified as diphenyl ethers (6,7), benzoxazinones (8), phenyl imides (9)(10)(11)(12), triazolinones (13), tetrazolinones (14), oxadiazolones (15), thiadiazolidines (16), isothiazolones (17), and arylpyrroles (18). 2-(7-Fluoro-3-oxo-3,4-dihydro-2H-benzo-[b] [1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-2H-isoindoline-1,3-diones are a class of phenylimide protoxinhibiting herbicides (19,20).…”