Relation Between Structure and Herbicidal Activity of Substituted Benzothiadiazoles (2,1,3)

Abstract

Summary. A large number of substituted benzothiadiazoles (2,1,3) was synthesized. In this report, the herbicidal activities of some halo‐ and alkyl‐substituted benzothiadiazoles (2,1,3) are described. It was found experimentally that at least one of the positions 5 and 6 in the molecule must be unsubstituted. Some di‐ and tri‐substituted derivatives had excellent herbicidal activities, in contrast to tetra‐substituted benzothiadiazoles (2,1,3). Relation entre la structure et I'activité herbicide des (2,1,3) benzothiadiazoles substitués

Reactions of Arylthiazylamides with Internal and External Fluoro Electrophiles − Formation of Products with Unusual Structures

“…4i), these compounds also satisfy the primary requirements for materials with nonlinear optical properties as they contain donor (Ar) and acceptor (4-Py F ) fragments connected by an ϪNϭSϭNϪ bridge capable of π-conjugation. Complexes 5e·9 and 8·C 10 F 8 are the first examples of a heterocycle (9) and an essentially nonplanar tweezer-like molecule (Z,Z-8) to feature areneϪpolyfluoroarene π-stacking interactions. Besides typical arylϪpolyfluoroaryl stacking, the crystal packing of 8·C 10 F 8 also reveals an unprecedented supramolecular motif, namely polyfluoroarylϪpolyfluoroaryl π-stacking, thus making this a new type of areneϪpolyfluoroarene complex.…”

“…1a,b). When treated with CsF in boiling CH 3 CN, cyclization to the well-known 2,1,3-benzothiadiazole 2a [8] and its previously unreported 4-fluoro derivative 2b was observed (the 5-F isomer of 2b was prepared some time ago [9] ). Our approach represents a useful extension of the established methods for the preparation of carbocyclic-substituted derivatives of 2a.…”

Chalcogen Bonding “2S–2N Squares” versus Competing Interactions: Exploring the Recognition Properties of Sulfur

“…Compounds 9f, 9h,a nd 10 are new compounds and their synthesis, characterization and crystallographic data are provided in the Supporting Information. Compounds 2a, [127] 2b, [128] 2c, [129] 3b, [130] 4a, [131] 4b, [132] 4c, [133] 4d, [134] 5a, [64] 5b, [60] 5c, [68] 5d, [135] 5e,a nd 7 were obtained commercially.T hese compounds were reported previously (except for 5e and 7), without crystallographic characterization. The crystals were grown or used as received, and reported for the first time in this report (see Supporting Information).…”

Polychloroheteroaromatic Compounds

“…Chlorination in the molten state at 190-200° in the presence of iron filings gives 4,5,7-trichloro-(388; R = H) or 4,5,6,7-tetrachloro-benzo-2,1,3-thiadiazole (388; R = Cl), depending on the conditions [842][843][844][845]. 5"-Chlorobenzo-2,1,3-thiadiazole gives either of these products on chlorination, again depending on the reaction conditions, whilst 4-methylbenzo-2,1,3thiadiazole gives its 5,6,7-trichloro-derivative.…”

“…Polychlorobenzo-2,1,3-thiadiazoles show promising herbicidal activity [107,[845][846][847][848]. Of particular interest in this respect is the 4,5,7-trichloro-derivative (388; R = H) (Phillips Th-052-H); the 5,7 -dichloro-4-methyl derivative also shows strongly herbicidal activity.…”