1016-59-7Relevant articles and documents
An improved synthetic method of phenazine-1-carboxylic acid
Zhan,Zhu,Huang,Liu,Zhu
, p. 3355 - 3360 (2015)
An improved synthetic method of a natural fungicide, phenazine-1-carboxylic acid, was reported. In brief, the process constitutes of (a) one-pot synthesis of 1-methyphenazine (IV) from pyrocatechol and 3-methyl-2-aminoaniline, (b) Wohl-Ziegler bromination of IV, (c) hydrolyzation of 1-bromomethylphenazine (III) in aqueous solution of Na2CO3/N,N-dimethylformamide (1.1:1, v/v), (d) oxidation of 1-phenazinemethanol (II) by O2 under the catalyzation of N-bromosuccinimide. This method provided an effective synthesis of phenazine-1-carboxylic acid in the overall yield of 66 %.
Reactivity and substituent effects in the cyclization of N-aryl-2-nitrosoanilines to phenazines
Wróbel, Zbigniew,Plichta, Karolina,Kwast, Andrzej
, p. 3147 - 3152 (2017)
Reactivity of variously substituted N-aryl-2-nitrosoanilines in the reaction of cyclization leading to phenazine derivatives, carried out in the presence of N,O-bis(trimethylsilyl)acetamide (BSA), was estimated on the base of the observed reaction times. A strong opposite effect of substituents located at position para to the nitroso group and those located para to the amino group in the side ring was observed. Mechanistic explanation, based on the electronic properties of the substituents and their mesomeric effects, was presented. The usefulness of the obtained data for the designed syntheses of phenazines was exposed.
Synthesis and bioactivities of Phenazine-1-carboxylic acid derivatives based on the modification of PCA carboxyl group
Xiong, Zhipeng,Niu, Junfan,Liu, Hao,Xu, Zhihong,Li, Junkai,Wu, Qinglai
, p. 2010 - 2013 (2017)
Phenazine-1-carboxylic acid (PCA) as a natural product widely exists in microbial metabolites of Pseudomonads and Streptomycetes and has been registered for the fungicide against rice sheath blight in China. To find higher fungicidal activities compounds and study the effects on fungicidal activities after changing the carboxyl group of PCA, we synthesized a series of PCA derivatives by modifying the carboxyl group of PCA and their structures were confirmed by 1H NMR and HRMS. Most compounds exhibited significant fungicidal activities in vitro. In particular, compound 6 exhibited inhibition effect against Rhizoctonia solani with EC50 values of 4.35?mg/L and compound 3b exhibited effect against Fusarium graminearum with EC50 values of 8.30?mg/L, compared to the positive control PCA with its EC50 values of 7.88?mg/L (Rhizoctonia solani) and 127.28?mg/L (Fusarium graminearum), respectively. The results indicated that the carboxyl group of PCA could be modified to be amide group, acylhydrazine group, ester group, methyl, hydroxymethyl, chloromethyl and ether group etc. And appropriate modifications on carboxyl group of PCA were useful to extend the fungicidal scope.
Phenazine-1-carboxylic acid carboxyl derivative and sterilization composition with derivative
-
Paragraph 0049; 0050; 0051; 0052, (2017/07/18)
The invention discloses a phenazine-1-carboxylic acid carboxyl derivative and a sterilization composition with the derivative. The general formula of the phenazine-1-carboxylic acid carboxyl derivative is as shown in the specification, wherein R refers to one or more saturation and unsaturation hydrocarbyl, alcoxyl methylene, methyl containing halogen, cyanoethyl, esteryl, acetal, hydroxymethyl, carboxylic acid methyl ester, acylamino, hydrazide, amine methyl and methyl hydrazone or ketone. The composition has broad-spectrum insect killing and sterilizing activities and can be used for preventing diseases caused by a plurality of harmful bacteria such as oomycetes, bssidiomycetes, ascomycetes and deuteromycetes on various crops.
