Some Herbicidal Silicon Compounds

Leasure, J. K.; Speier, John L.

doi:10.1021/jm00324a036

Cited by 9 publications

(3 citation statements)

References 1 publication

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“…(Dichloromethyl)trichlorosilane and (dichloromethyl)methyldichlorosilane were obtained from Gelest, Inc. and used without purification. (1,2-Dichloroethyl)trichlorosilane and (2,3-dichloropropyl)trichlorosilane were prepared by the photochlorination of vinyltrichlorosilane and allyltrichlorosilane with chlorine gas, respectively. The reaction products were analyzed by GLC using a packed column (10% SE-30 or SE-54 on 80−100 mesh chromosorb W/AW, 1/8 in.…”

Section: Methodsmentioning

confidence: 99%

One-Step Synthesis of Fluorenyl-Substituted Chlorosilanes: Friedel−Crafts Type Cycloalkylation of Biphenyl with (Dichloroalkyl)silane

et al. 2001

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Friedel−Crafts alkylation reactions of biphenyl with (dichloroalkyl)chlorosilanes [Cl3 - m Me m Si(C n H2 n - 1Cl2), m = 0−2, n = 1−3] at temperatures ranging from 120 to 160 °C in the presence of a Lewis acid catalyst gave cyclized products, fluorenyl-substituted chlorosilanes, in 47−94% yields. In these reactions, the reactivities of (dichloroalkyl)silanes generally increase as the number of methyl groups on the silicon atom and the alkyl chain length increase. However, desilylation of the alkylated products and starting chlorosilanes was observed in the case of (dichloroalkyl)silanes having two or more methyl groups on the silicon. Alkylation with (dichloromethyl)dimethylchlorosilane proceeded at 120 °C but gave fluorene and dimethyldichlorosilane resulting from desilylation of the products. The reactivities of (dichloroalkyl)silanes decrease in the following order: m = 2 > 1 > 0; n = 2 > 1. The catalytic efficiencies of Lewis acids for the cycloalkylation reactions decrease in the following order: AlCl3 > AlBr3 > HfCl4 > ZrCl4 ≫ TiCl4.

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Section: Methodsmentioning

confidence: 99%

One-Step Synthesis of Fluorenyl-Substituted Chlorosilanes: Friedel−Crafts Type Cycloalkylation of Biphenyl with (Dichloroalkyl)silane

et al. 2001

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“…Compounds Affecting Plant Growth-Leasure and his coworkers (175)(176)(177) to be prone to hydrolysis from silicon (e.g., alkoxy), are reported to exhibit strong herbicidal action (177).…”

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confidence: 99%

Organosilicon Entities as Prophylactic and Therapeutic Agents

Garson

Kirchner²

1971

Journal of Pharmaceutical Sciences

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“…Frankel and coworkers (9) have synthesized several silicon containing barbiturates, a silicon containing analogue of chloroamphenicol, and phenethylamine having a trimethylsilyl moiety attached to the aromatic grouping. Leasure and Speier synthesized a group of (haloalkyl) silicon compounds which were found to have strong herbicidal activity and in mme cases to act as defolients (10).…”

mentioning

confidence: 99%

Organosilicon compounds III. Silicon‐substituted thiophene derivatives of mercaptoethylamine as possible radioprotective agents

Thames

Mccleskey

1967

Journal of Heterocyclic Chem

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The preparation of the first organosilicon containing derivatives of mercaptoethylamine as possible radioprotective agents is described. The synthesis of these compounds via the thiazolidine intermediate was chosen due to the known radioprotective action of certain thiazolidines. We have prepared seventeen previously unreported organosilicon derivatives of which eleven contain the thiazolidine moiety and six are derivatives of mercaptoethylamine. The ability of these derivatives to protect against ionizing radiation will be determined.The synthesis and evaluation of silicon-substituted medicinal agents is rapidly developing into an exciting and potentially explosive area of medicinal chemistry. TheThe apparent potential of organosilicon medicinals coupled with the known radioprotective action of 2-aminoethanethiol has prompted us to synthesize silicon substisimilarities, as well as the differences, between organo-carbon and organo-silicon compounds suggests that organosilicon containing medicinals would show unique physiological properties.considers that silicon, although larger than carbon, pos-Si-C bond length is approximately 20% longer than the C-C bond. Furthermore, silicon has a lower electronegativity (en = 1.8) than carbon (en = 2.5), and it is able to utilize its 3d-orbitals for bond formation. This concept appears particularly attractive when one 0 -R e ($i.Rl n -B u L i ___, sesses covalent bonding characteristics ( s p 3 ) and that the -R gThat organosilicons can function as medicinals was confirmed by Fessenden and Coon, who prep'ared organosilicons that exhibited muscle relaxant and tranquilizing properties (2,3).The marked lipid solubility of silicon ethers has been successfully established by Chang and Jain (4), who prepared several testosteroxysilanes and determined the effectivenessof these drugs. Similarly, Brown and Laos (5) have prepared a number of steroidal oxysilanes and have found these to have anabolic and androgenic activity. Ghoby and Neuworth (6) have prepared trimethylsilyl derivatives of salicylic acid while Gertner, Rosen and Zilkha (7) as well as Ruehlmann, Hils and Graubaum (8) have prepared organosilicon derivatives of aminoacids. Frankel and coworkers (9) have synthesized several silicon containing barbiturates, a silicon containing analogue of chloroamphenicol, and phenethylamine having a trimethylsilyl moiety attached to the aromatic grouping. Leasure and Speier synthesized a group of (haloalkyl) silicon compounds which were found to have strong herbicidal activity and in mme cases to act as defolients (10). SCHEME A SCHEME 8 n L J I

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Some Herbicidal Silicon Compounds

Cited by 9 publications

References 1 publication

One-Step Synthesis of Fluorenyl-Substituted Chlorosilanes: Friedel−Crafts Type Cycloalkylation of Biphenyl with (Dichloroalkyl)silane

One-Step Synthesis of Fluorenyl-Substituted Chlorosilanes: Friedel−Crafts Type Cycloalkylation of Biphenyl with (Dichloroalkyl)silane

Organosilicon Entities as Prophylactic and Therapeutic Agents

Organosilicon compounds III. Silicon‐substituted thiophene derivatives of mercaptoethylamine as possible radioprotective agents

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