Carbamoyl oximes

Miles, C.J., Trehy, M.L., and Yost, R.A. Degradation of A-methylcarbamate and carbamoyl oxime pesticides in chlorinated water. Bull. Environ. Contam. Toxicol, 41(6) 838-843, 1988. 

Carbamoyl oximes, car-bamothioc acids, dithiocar-bamates and phenyl urea types Vegetation HPLC with post-column photolysis for the generation of fluorophores [64]... 

Miles and Moye [171] have shown that several classes of nitrogen containing pesticides responded to a high performance liquid chromatography post-column reaction detector that employed ultraviolet photolysis with optional reaction with o-phthalicdicarboxaldehyde-2-mercaptoethanol followed by fluorescence detection. It was applied to the determination of jV-methylcarbamates, carbamoyl oximes, carbamethoic acids, dithiocarbamates and phenyl ureas, phenyl amides and phenyl carbamates in groundwater. See also Table 4.3. 

Oxime amides (Carbamoyl oximes or oxyimino amides) are compounds with the function... 

BIQ660 CAS 63942-43-8 HR 3 N,N -BIS(2-CYANO-2-METHYLPROPION-ALDEHYDEO-(N-METHYL-CARBAMOYL)OXIME)SULFIDE... 

MLX820 CAS 62382-23-4 HR 3 2-METHYL-2-(METHYLTHIO)PROPAN-OL-o-((N-METHYL-N-MORPHOLINO-SULFENYL)CARBAMOYL)OXIME... 

SYNS 2-METHYI 2-(METHYLTHIO)PROPANOL-o-((METHYL(4-MORPHOLINYLTHIO)AMINO)CARBON-YL)OXIitE 2-METHYL-2-(METHYLTHIO)PROPION-ALDEHTOE-o-(N-METHYL-N-(4-MORPHOUNOSUI FENYL)CARBAMOYL)OXIME PROPANOL, 2-METHYL-2-(METHYLTHIO)-, o-((METHYL(4-MORPHOLINYLTHIO)AMINO)CARBONYL)OXIME... 

METHYL-2-METHYLTHI0-PR0PI0NALDEHYD-0-(N-METHYL-CARBAMOYL)-OXIM (GERi L N) see CBM500... 

Carbamoyl oximes, formed by the reaction of aldehyde and ketone oximes with isocyanates, have been known since the end of the last century (Goldschmidt, 1889). The pioneer work in the field of their use as insecticides is due to the research group of the Union Carbide Corp., Payne and co-workers (Payne and Weiden, 1962 Weiden et. al., 1965 Payne et al., 1966). 

A few years after the synthesis of aldicarb, several research groups prepared, independent of each other, analogues of aldicarb which have only one carbon atom instead of two between the sulfur atom and the oxime-nitrogen (Anonym, 1966a 1966b Anders, 1967). Finally, 1-methylmercaptoacetaldehyde-O-methyl-carbamoyl oxime (methomyl, 46) was put onto the market as the result of work by the research group of the Du Pont Co. 

Carbamoylformimidic acid. SeeOxamide N-Carbamoylhydroxylamine Carbamoyl oxime. 

Bristol-Myers Squibb has recently disclosed two different series of carbamate-based FAAH inhibitors. The first of these is a series of 4,5-diaryl-imidazoles in which 30 compounds are specifically claimed, an example being compound (57). This compound is reported to have an IC50 value of < 10 nM. In addition, (57) was also active in vivo in rodent models of chemo-induced, thermal and neuropathic pain [72]. The second series of compounds is based on oxime carbamoyl FAAH inhibitors such as (58). Compound (58) is reported to have an IC50 value of < 10 nM and activity in rodent models of inflammatory pain, thermal pain and inflammatory oedema [73]. 

Photosensitized decomposition of oxime oxalyl amides proceeded via carbamoyl radicals which underwent A-exo cyclizations forming four-membered /3-lactams as main products. Irradiation of solution of oxime derivative 22 and 4-methoxyacetophenone (MAP) in toluene at 100 °C with a 400 W UV lamp led to azetidinone 23 in 3 1 ratio of diastereoisomers (equation 10) . ... 

The rearrangement of the oximes obtained from 2-acyl-1,3-selenazoles 326 provides an efficient synthesis of 2-carbamoyl-1,3-selenazoles 327 ° (equation 120). 

The kinetics of reaction of O-(A-ary I carbamoyl) be n zop h cn o n c oximes in NaOMe-MeOH to give benzophenone oxime sodium salt and the corresponding methyl N-arylcarbamates have been studied.6 The Hamnett constants pobs = 0.68 and pkl = —1.32 have been estimated for the E cBR process for which 2 governs conversion of the intermediate ArNrC02N=CPh2 to ArN=C=0 and Ph2C=NO. ... 

J). Reversible phosphorylation of AChE by I may be controlled efficiently by specific reactivators (oximes) in contrast to carbamoyl-AChE conjugate. 

Oxime group position. .. 2,3,4 Carbamoyl group position. .. 3,4... 

Attempts were also made to access penicillin derivatives by this route. Several thiazolidine-containing oxime oxalate amides were prepared and photol-ysed under the same conditions, but without success [84]. It is known that and other conventional cyclisations onto oxime ether acceptors (> C = NOR) are faster than onto alkene acceptors [85]. In the hope that cyclisation onto an oxime ether acceptor would also be more efficient, oxime oxalate amide 80 containing both a thiazolidine ring and oxime ether acceptor was prepared. The photosensitised reaction of 80 did yield the desired carbamoyl radical 81, as shown by EPR spectroscopy. However, the presence of the thiazolidine ring evidently inhibited 4-exo cyclisation because no significant amount of cyclisation to radical 82 took place and none of the penicillin derivative was isolated. 

---