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Search for the shortest intermetallic Tl—Tl contacts: Synthesis and characterization of Thallium(I) coordination polymers with several mono- and bis-cyanoximes

Five new Tl(I) coordination compounds based on aryl monocyanoximes, such as phenylcyanoxime – HPhCO, 1, 2-fluorophenylcyanoxime – H(2F-PhCO, 2, 3-fluorophenylcyanoxime – H(3F-PhCO), 3, of TlL composition, and aryl biscyanoximes, such as 1,3-cyanoxime (benzene) – H2(1,3-BCO, 4 and 1,4-cyanoxime (benzene) – H2(1,4-BCO), 5 of Tl2L stoichiometry were synthesized and characterized using spectroscopic methods, thermal stability studies, and X-ray analysis. All obtained complexes represent coordination polymers of different complexity, ranging in dimensionality from 1D in Tl(2F-PhCO) to 3D in Tl2(1,3-BCO). The most interesting feature of all synthesized complexes is the formation of Tl2O2 rhombs: non planar and non-centrosymmetric in Tl(PhCO), and planar and centrosymmetric in the other three compounds. These rhombi are interconnected, forming zigzag and ladder-type polymers in which very short thallophilic Tl—Tl distances were observed. Thus, in the structure of Tl2(1,3-BCO) the closest distance between metal centers was found to be 3.670 ?. This is the second shortest on-record intermetallic contact in non-organometallic and non-cluster, but Werner type complexes, and is close to that in metallic thallium: 3.456 ?. In all five new coordination polymers the central atom has a stereo-active 6 s2 lone pair that significantly distorts the shape of the coordination polyhedron of Tl(I). The first time, Tl–O vibrations in Tl2O2 rhombs were observed in Raman spectra of the obtained complexes. Thermal analysis studies evidenced stability of all complexes, but Tl(PhCO), to ～200 °C. The Tl2(1,3-BCO) compound demonstrates properties of the high energy compound, and violently exothermically decomposes at ～255 °C with the release of a significant amount of kinetic energy. The final product of anaerobic decomposition of all studied Tl-cyanoximates is metallic thallium sponge.

Oxime ethers, the preparation thereof, compositions containing them and use thereof

The invention relates to oxime ethers of the formula I STR1 wherein n is 1 or 2, each of R1 and R2 is hydrogen or C1 -C4 alkyl each of R3 and R4 is hydrogen, halogen, C1 -C4 alkyl, C1 -C4 haloalkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 haloalkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, C1 -C4 haloalkylsulfinyl, C1 -C4 haloalkylsulfonyl or nitro; each of R5 and R6 independently of the other is hydrogen, C1 -C4 alkyl, C1 -C4 haloalkyl, phenyl or phenyl which is substituted by halogen, C1 -C4 alkyl, C1 -C4 haloalkyl, C1 -C4 alkoxy, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 alkylsulfinyl, C1 -C4 alkylsulfonyl, carboxyl, carbamoyl, C 1 -C4 alkylcarbamoyl, nitro or cyano, or R5 and R6 together are also a 2- to 6-membered alkylene or alkenylene chain which may be substituted by C1 -C4 alkyl radicals; X is hydrogen, cyano, nitro, chlorine, C1 -C4 alkyl, C1 -C4 haloalkyl, C3 -C6 cycloalkyl, carboxyl, carbamoyl, C1 -C4 alkylcarbonyl, C1 -C4 alkoxycarbonyl or C1 -C4 alkylcarbamoyl. The oxime ethers of the formula I are able to act as antidotes or safeners to protect cultivated plants from the phytotoxic effects of herbicides. Such cultivated plants are preferably sorghum, cereals, maize and rice.