27050-96-0

Usage

Physical properties

Red-colored solid

Uses

Bactericide and fungicide in agriculture for protecting plants from bacterial and fungal diseases, primarily used in fruit and vegetable production

Mode of action

Inhibits the growth of microorganisms

Mammalian toxicity

Low toxicity

Approval

Approved for use in some countries

Controversy

Potential environmental impact and development of resistance in harmful microorganisms

Research

Ongoing efforts to develop alternative, more sustainable methods for disease control in agriculture.

Upstream product

• 18711-38-1 1-methyl-5-nitropyrrole-2-carboxaldehyde 

Downstream Products

• 1017279-91-2 C₁₇H₁₈ClN₃O₃ 
• 1017279-00-3 (E)-(4-{methyl[(1-methyl-5-nitro-2-pyrrolyl)methyl]-amino}methyl)cinnamic acid trifluoroacetate 
• 1017278-98-6 tert-butyl (E)-(4-{methyl[(1-methyl-5-nitro-2-pyrrolyl)methyl]amino}methyl)cinnamate 
• 1357580-61-0 (E)-N-(4-(3-(5-amino-1-methyl-1H-benzo[e]indol-3(2H)-yl)-3-oxoprop-1-enyl)benzyl)-N,N-dimethyl-1-(1-methyl-5-nitro-1H-pyrrol-2-yl)methanaminium bromide hydrobromide 
• 1017279-16-1 N-4-((E)-3-{5-[bis(tert-butoxycarbonyl)]-amino-1-methyl-1,2-dihydro-3H-benzo[e]indol-3-yl}-3-oxo-1-propenyl)benzyl-N,N-dimethyl-N-[(1-methyl-5-nitro-2-pyrrolyl)methyl]ammonium bromide 
• 1017279-08-1 (E)-N-(4-(3-(5-amino-1-(hydroxymethyl)-1H-benzo[e]indol-3(2H)-yl)-3-oxoprop-1-enyl)benzyl)-N,N-dimethyl-1-(1-methyl-5-nitro-1H-pyrrol-2-yl)methanaminium bromide hydrobromide 
• 1017279-07-0 N-4-((E)-3-{5-[bis(tert-butoxycarbonyl)]amino-1-[(tert-butoxycarbonyl)oxy]methyl-1,2-dihydro-3H-benzo[e]indol-3-yl}-3-oxo-1-propenyl)benzyl-N,N-dimethyl-N-[(1-methyl-5-nitro-2-pyrrolyl)methyl]ammonium bromide 
• 1357580-60-9 (E)-N-(4-(3-(1-(chloromethyl)-5-hydroxy-1H-benzo[e]indol-3(2H)-yl)-3-oxoprop-1-enyl)benzyl)-N,N-dimethyl-1-(1-methyl-5-nitro-1H-pyrrol-2-yl)methanaminium bromide hydrobromide 
• 1017278-92-0 5-[bis(tert-butoxycarbonyl)]amino-1-(chloromethyl)-3-{(E)-3-[4-({methyl[(1-methyl-5-nitro-2-pyrrolyl)methyl]amino}methyl)phenyl]-2-propenoyl}-1,2-dihydro-3H-benzo[e]indole 
• 1017278-85-1 (E)-N-(4-(3-(5-amino-1-(chloromethyl)-1H-benzo[e]indol-3(2H)-yl)-3-oxoprop-1-enyl)benzyl)-N,N-dimethyl-1-(1-methyl-5-nitro-1H-pyrrol-2-yl)methanaminium bromide hydrobromide 
• 1017278-84-0 N-4-((E)-3-{5-[bis(tert-butoxycarbonyl)]amino-1-(chloromethyl)-1,2-dihydro-3H-benzo[e]indol-3-yl}-3-oxo-1-propenyl)benzyl-N,N-dimethyl-N-[(1-methyl-5-nitro-2-pyrrolyl)methyl]ammonium bromide 

Relevant academic research and scientific papers

Synthesis and evaluation of nitroheterocyclic phosphoramidates as hypoxia-selective alkylating agents

A series of novel nitroheterocyclic phosphoramidates has been prepared, and the cytotoxicity of these compounds has been evaluated in clonogenic assays against B16, wild-type and cyclophosphamide-resistant MCF-7, and HT-29 cells under aerobic conditions and HT-29 cells under hypoxic conditions. All compounds were comparable in toxicity to wild-type and resistant MCF-7 cells and were also selectively toxic to HT-29 cells under hypoxic conditions (selectivity ratios 1.7 to > 20). Analogues lacking the nitro group were not cytotoxic. Electron-withdrawing substituents increased cytotoxicity under aerobic conditions and thereby decreased hypoxic selectivity. In contrast, an electron-donating substituent markedly decreased both aerobic and hypoxic cytotoxicity but enhanced hypoxic selectivity. Chemical reduction of the nitro group resulted in rapid expulsion of the cytotoxic phosphoramide mustard. The most potent of these compounds show significant cytotoxicity under both aerobic and hypoxic conditions.

Hypoxia-selective antitumor agents. 16. Nitroarylmethyl quaternary salts as bioreductive prodrugs of the alkylating agent mechlorethamine

Nitrobenzyl quaternary salts of nitrogen mustards have been previously reported as hypoxia-selective cytotoxins. In this paper we describe the synthesis and evaluation of a series of heterocyclic analogues, including pyrrole, imidazole, thiophene, and pyrazole examples, chosen to cover a range of one-electron reduction potentials (from -277 to -511 mV) and substitution patterns. All quaternary salt compounds were less toxic in vitro than mechlorethamine, and all were more toxic under hypoxic than aerobic conditions, although the differentials were highly variable within the series. The most promising analogue, imidazole 2, demonstrated DNA crosslinking selectively in hypoxic RIF-1 cells, and was active in vivo in combination with radiation or cisplatin. However, 2 also produced unpredictable toxicity in vivo, suggestive of nonspecific nitrogen mustard release, and this has restricted further development of these compounds as hypoxia-selective cytotoxins.

Radiation-activated cytotoxin therapy of neoplastic disease

A method of treating neoplastic disease wherein a patient in need of such treatment is administered an effective amount of a radiation-activated cytotoxin prodrug (RACP) which has low toxicity, which is reducible by reducing agents generated by the radiol