- Synthesis and fungicidal activity of 1,3,4-oxadiazol-2-yl thioether derivatives containing a phenazine-1-carboxylic acid scaffold
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To find new higher fungicidal activities lead compounds and develop new eco-friendly agrochemicals, natural product phenazine-1-carboxylic acid (PCA) as scaffold, a series of 1,3,4-oxadiazol-2-yl thioether derivatives was synthesized and bio-assayed. The results reveal that most target compounds possessed moderate to good fungicidal activities against R. solani, S. sclerotioru and P. oryzac Cavgra. Compounds 6n and 6o exhibit more than 90% bioactivity against S. sclerotioru. The EC50 value of compounds 6n and 6o are 11.16 and 30.47 μM respectively, in particular, compound 6n show equal activity against S. sclerotioru to PCA (10.49 μM). This result provides a valuable lead compound for further studies.
- Xingliang, Lu,Xiang, Zhu,Min, Zhang,Qinglai, Wu,Xudong, Zhou,Junkai, Li
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- Insights on the susceptibility of plant pathogenic fungi to phenazine-1-carboxylic acid and its chemical derivatives
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Pseudomonas chlororaphis subsp. aureofaciens strain M71 produced two phenazine compounds as main secondary metabolites. These metabolites were identified as phenazine-1-carboxylic acid (PCA) and 2-hydroxyphenazine (2-OH P). In this study, the spectrum of the activity of PCA and 2-OH P was evaluated against a group of crop and forestal plant pathogenic fungi by an agar plate bioassay. PCA was active against most of the tested plant pathogens, while 2-OH P slightly inhibited a few fungal species. Furthermore, four semisynthesised derivatives of PCA (phenazine-1-carboxymethyl, phenazine-1-carboxamide, phenazine-1-hydroxymethyl and phenazine-1-acetoxymethyl) were assayed for their antifungal activity against 11 phytopathogenic species. Results showed that the carboxyl group is a structural feature important for the antifungal activity of PCA. Since the activity of phenazine-1-carboxymethyl and phenazine-1- carboxamide, the two more lipophilic and reversible PCA derivatives remained substantially unaltered compared with PCA.
- Puopolo, Gerardo,Masi, Marco,Raio, Aida,Andolfi, Anna,Zoina, Astolfo,Cimmino, Alessio,Evidente, Antonio
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- An umpolung strategy for rapid access to thermally activated delayed fluorescence (TADF) materials based on phenazine
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Herein, Ag(I)-promoted regioselective intramolecular radical nucleophilic addition/rearrangement of 2-aryl diazaboroles has been accomplished for the first time to construct phenazine structures. This protocol is an umpolung strategy based on the classical electrophilic mechanism, and therefore, a reversed regioselectivity was observed, which provides an opportunity to prepare sterically hindered phenazines. The resulting thermally activated delayed fluorescence (TADF) materials based on phenazine exhibit emission bands from green to red with high quantum yields and moderate fluorescence lifetimes as solid films.
- Cheng, Hu,Guo, Qiang,Lan, Jingbo,Ran, Chunhao,Wu, Di,Zhang, Huaxing
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supporting information
p. 1581 - 1584
(2022/02/10)
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- Synthesis and bioactivities of diamide derivatives containing a phenazine-1-carboxamide scaffold
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Taking natural product phenazine-1-carboxamide (PCN) as a lead compound, a series of novel phenazine-1-carboxylic acid diamide derivatives were designed and synthesised. Their structures were confirmed by 1H-NMR and HRMS. The bioassays showed that some of the target compounds exhibited promising in vitro fungicidal activities, and exhibited excellent and selective herbicidal activities. Particularly, compounds c, h, o and s displayed root length inhibition activities against barnyard grass with the rate of more than 80%. Compound c exhibited the best activity among all the target compounds against barnyard grass stalk length with the IC50 value of 0.158?mmol/L, and compound o exhibited the best and wide spectrum inhibition against barnyard grass root length and rape in both root length and stalk length herbicidal activities with its IC50 values of 0.067, 0.048 and 0.059?mmol/L respectively. The analysis of preliminary Structure-Activity Relationships provides the theoretical basis for further design of phenazine-1-carboxylic acid.
- Zhu, Xiang,Zhang, Min,Yu, Linhua,Xu, Zhihong,Yang, Dan,Du, Xiaoying,Wu, Qinglai,Li, Junkai
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supporting information
p. 2453 - 2460
(2018/03/29)
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- Phenazine-1-carboxylic acid bisamide compounds and application thereof
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The invention provides phenazine-1-carboxylic acid bishydrazide compounds and an application thereof, and belongs to the technical field of preparation of pesticide compounds; the general formula of the compounds has the following structure defined in the specification, wherein R is saturated C2-C6 straight-chain or branched-chain alkyl, unsaturated C2-C6 alkyl, halogen substituted C2-C6 hydrocarbonyl, C3-C8 cycloalkyl, and substituted phenyl containing one or more saturated or unsaturated hydrocarbonyl, alkoxy, halogen, fluorine-containing methyl, nitryl, cyano group, ester group, ketone group and formyl group, substituted pyridyl, substituted furyl, substituted pyrimidyl, substituted pyrazolyl, substituted thiazolyl, substituted thienyl, substituted imidazolyl or substituted triazolyl. The phenazine-1-dihydrazine carboxylic acid compounds have novel structure, can be used for prevention and treatment of diseases on crops and weeds and have market application prospects.
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Paragraph 0034; 0038; 0039; 0040
(2018/03/28)
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- 2-substituted sulfenyl-5-(1-phenazinyl)-1,3,4-oxadiazole compound and application thereof
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The invention provides a 2-substituted sulfenyl-5-(1-phenazinyl)-1,3,4-oxadiazole compound and application thereof. A general formula has a structure shown in the specification, wherein R is a substituted phenyl (containing one or a plurality of saturated or unsaturated alkyls, alkoxyls, halogens, fluorine-containing methyls, nitryls, cyano-groups, ester groups, ketone groups and aldehyde groups), a substituted pyridyl, a substituted furan group, a substituted pyrazolyl, a substituted thiazolyl, a substituted thienyl and a substituted Marleen group; n is any one number from 0 to 10. The 2-substituted sulfenyl-5-(1-phenazinyl)-1,3,4-oxadiazole compound with the novel structure can be used for preventing and treating crop diseases.
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Paragraph 0033; 0034; 0035
(2017/12/27)
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- Phenazine-1-carboxylic acid carboxyl derivative and sterilization composition with derivative
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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.
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Paragraph 0043; 0044; 0045
(2017/07/18)
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- Phenazine-1-formylpiperazine compound and applications thereof
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The present invention belongs to the chemical field of chemistry, and particularly relates to a phenazine-1-formylpiperazine compound and applications thereof, wherein the general formula of the compound has the following structure defined in the specific
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Paragraph 0033; 0037; 0038; 0039
(2017/10/09)
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- Synthesis and bioactivities of Phenazine-1-carboxylic acid derivatives based on the modification of PCA carboxyl group
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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.
- Xiong, Zhipeng,Niu, Junfan,Liu, Hao,Xu, Zhihong,Li, Junkai,Wu, Qinglai
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supporting information
p. 2010 - 2013
(2017/04/07)
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- Derivatives of 1-phenazincarboxylic acid
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The important biological properties of some compounds having phenazinic rings decided upon the synthesis of new substances by condensing 1-phenazincarboxylic acid hydrazide with aromatic aldehydes. The new compounds have been characterized by IR , NMR spectra.
- Nicolae, Anca,Drǎghici, Constantin,Maior, Ovidiu,Ianculescu, Gabriela
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p. 131 - 136
(2007/10/03)
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- 2,3,9-Trihydroxyphenazin-1-carbonsaeure - ein unter Berylliumeinwirkung gebildetes neues Phenazinderivat aus Pseudomonas fluorescens
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In addition to phenazine, phenazine-1-carboxylic acid, phenazine-1,6-dicarboxylic acid and 2,9-dihydroxyphenazine-1-carboxylic acid a new compound, viz. 2,3,9-trihydroxyphenazine-1-carboxylic acid could be isolated from the culture medium of Pseudomonas fluorescens grown under iron deficiency with beryllium added to the culture medium.Its structure elucidation is described.
- Taraz, K.,Schaffner, E. M.,Budzikiewicz, H.,Korth, H.,Pulverer, G.
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p. 552 - 556
(2007/10/02)
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- PHENAZINES FROM Streptomyces cinnamonensis
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Phenazine-1-carboxylic acid (Ia) and 6-(3-methyl-2-butenyl)phenazine-1-carboxylic acid (IIa) were isolated from the mycelium of the strain Streptomyces cinnamonensis ATCC 15 413.Identification and structure elucidation were performed by spectroscopic methods.Both compounds weakly inhibit the growth of gram-positive bacteria.
- Tax, Jiri,Sedmera, Petr,Vokoun, Jindrich,Urban, Jiri,Karnetova, Jaroslava,et al
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p. 527 - 532
(2007/10/02)
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