Dicarboximides

Their development and commercial success was favoured by the coincidence of resistance to benzimidazole fungicides. 

The range of activity of the dicarboximides includes the control of many major ascomycete, deuteromycete and basidiomycete pathogens in a wide range of crops. The activity spectrum varies slightly between compounds. 

The dicarboximides inhibit spore germination and cause increased branching, swelling and lysis of germ tubes and hyphal tips. Effects on cell division have been reported but no major inhibition of nucleic acid metabolism, respiration, protein or lipid synthesis has been observed. 

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INFORMATIONRETRIEVAL]poll4) cis-N-[l,l,2,2- Petrachloroethyl)thio]cyclohexene-1,2- dicarboximide[2425-06-1]... 

Direct conversion of an Fmoc group to a Cbz group KF, TEA, DMF, A-benzyloxycarbonyloxy-5-norbomene-2,3-dicarboximide, 7-12 h, 83-99% yield. ... 

Thus amides are found to be only very weakly basic in water [pKa for ethanamide(acetamide) is =0-5], and if two C=0 groups are present the resultant imides, far from being basic, are often sufficiently acidic to form alkali metal salts, e.g. benzene-1,2-dicarboximide (phthalimide, 8) ... 

Synthesis of block copolymers of norbornene derivatives, with different side groups, has been reported via ROMP [101]. Initially, exo-N-bulyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboximide was polymerized in acetone at room temperature with a ruthenium initiator (Scheme 40). The conversion of the reaction was quantitative. Subsequent addition of norbornene derivative carrying a ruthenium complex led to the formation of block copolymers in 85% yield. Due to the presence of ruthenium SEC experiments could not be performed. Therefore, it was not possible to determine the molecular weight... 

As a result of their low redox potentials [173], bis(phthalocyaninato) lanthanide complexes are often inadvertently reduced or oxidized, and they are also very sensitive to acids and bases. In order to solve these problems, Veciana et al. achieved certain success on designing a series of novel compounds with characteristics that would give them improved redox stability. Electroactive ligands based on phthalo-cyaninato tetra dicarboximide [175] or perfluorinated phthalocyanine [176] were used to assemble the double-decker lanthanide complexes, with the effect of stabilizing the negative charge of the anionic state of the compounds, which resulted in a strong shift of 0.7 V of their first oxidation potentials. 

Pyrrole is one of the most prominent heterocycles, having been known for more than 150 years, and it is the structural skeleton of several natural products, synthetic pharmaceuticals, and electrically conducting materials. A simple access to the pyrrole ring system involves the conversion of cyclic anhydrides into five-membered imides. Mortoni and coworkers have described the conversion of 2-methylquinoline-3,4-dicarboxylic acid anhydride to a quinoline-3,4-dicarboximide library by treatment of the anhydride with a diverse set of primary amines under microwave conditions (Scheme 6.180) [341]. The authors studied a range of different conditions, including dry media protocols (see Section 4.1) whereby the starting materials were adsorbed onto an inorganic support and then irradiated with microwaves. For the transforma-... 

Cyclohexanecarboxylic acid chloride, c351 Cyclohexaneethanol, c378 Cyclohexaneethyl acetate, c379 Cyclohexanemethanol, c384 Cyclohexanone cyanohydrin, hi 12 czis -4-Cyclohexene-l,2-dicarboximide, t82... 

Riviere, J.L., J. Bach, and G. Grolleau. 1983. Effect of pyrethroid insecticides and N-(3,5-dichlorophenyl) dicarboximide fungicides on microsomal drug-metabolizing enzymes in the Japanese quail (Cotumix cotumix). Bull. Environ. Contam. Toxicol. 31 479-485. 

Scheme 12. Perylene-3,4,9,10-tetracarboxdiimide 42 and perylen-3,4-dicarboximide 43 are typical representatives for...

Scheme 15. Coronene-tetracarboximide 51 and -dicarboximide 52 with alkyl substituents form liquid crystalline phases.

Along the same lines, it is exdting to monitor chemical transformations of single molecules. The perylene dicarboximide derivative 55 has a high pradical potential as a thermotropic dye for writ-... 

When the trouble is black thread, planters use paints, coal-tar washes, asphalt, and other treatments with varying degrees of success. New tests have shown that Fylomac 90, applied in a 0.25% solution, effects a cure in eight successive applications. In one of the most recent studies on this, Carpenter (8) tested 22 fungicides on Phytophthora panel trouble in Costa Rica. His work was under ideal conditions for the disease and with a well tested invariably successful, artificial method of inoculation. He found only one fungicide sufficiently good for his purpose—Ortho-cide 50 [captan, n-(trichloromethylthio)-4-cyclohexene-l,2-dicarboximide], wettable, mixed with Filmfast sticker. 

D. Lee, M. C. Choi, C. S. Ha, Polynorbornene dicarboximide/amine functionalized graphene hybrids for potential oxygen barrier films., Journal of Polymer Science Part a-Polymer Chemistry, vol. 50, pp. 1611-1621, 2012. 

Cyclohexene. 1 -Octene, Pentachlorophenol Cyclohexene, see Cyclohexanol, Methylene chloride 4 Cyclohexene-1,2-dicarboximide, see Captan Cyclohexene oxide, see Tetrachloroethylene... 

Chemical/Physical. Captan undergoes hydrolysis under neutral or alkaline conditions yielding 4-cyclohexene-l,2-dicarboximide, carbon dioxide, hydrogen chloride and sulfur (Wolfe et al., 1976a). The estimated hydrolysis half-life of captan in a phosphate buffer solution at pH 7.07 and 28-29 °C is 2.96 h. Between the pH range 2 to 6, the estimated hydrolysis half-life is 10.70 h (Wolfe et al, 1976a). Worthing and Hance (1991) reported hydrolysis half-lives of 8.3-32.4 h and <2 min at pH values 7 and 10, respectively. 

Electro-optical modulators are other examples whose efficiency is enhanced in the presence of ion-radicals. These devices are based on the sandwich-type electrode structures containing organic layers as the electron/hole-injecting layers at the interface between the electrode and the emitter layer. The presence of ion-radicals lowers the barrier height for the electron or hole injection. Anion-radicals (e.g., anion-radicals from 4,7-diphenyl-l,10-phenanthroline—Kido and Matsumoto 1998 from tetra (arylethynyl) cyclooctatetraenes—Lu et al. 2000 from bis (1-octylamino) perylene-3,4 9,10-bis (dicarboximide)s— Ahrens et al. 2006) or cation-radicals (e.g., cation-radicals from a-sexithienyl—Kurata et al. 1998 l,l-diphenyl-2-[phenyl-4-A/,A- /i(4 -methylphenyl)] ethylene— Umeda et al. 1990, 2000), all of them are electron or hole carriers. 

N-BND A-benzyloxycarbonyloxy-5-norbornene-endo-2,3-dicarboximide N-IBND A-butoxycarbonyloxy-5-norbornene-endo-2,3-dicarboximide... 

In addition to utilizing natural ODNs in block copolymers, ODN mimics have also been studied using polymers with the capability of forming hydrogen bonds. Bazzi and colleagues (Bazzi and Sleiman 2002 Bazzi et al. 2003) have reported diblock and triblock amphiphilic polymers with diamidopyridine (DAP) and dicarboximide moieties as molecular recognition units and studied their micelle formation properties (Chart 2.4). 

Chart 2.4 Structures of diblock and triblock ampbipbiUc pol3fmers with diatnidopyridine (DAP) and dicarboximide moieties. 

Figure 4.8 Synthesis of dicarboximide functional hydrogen bonding block copolymers via ROMP (Dalphond et al. 2002).

Dalphond J, Bazzi H, Kahrim K, Sleiman H. Synthesis and self-assembly of polymers containing dicarboximide groups by living ring-opening metathesis polymerization. Macromol Chem Phys 2002 203 1988-1994. 

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