Synthesis and Antifungal Activity of 2-Chloromethyl-1<i>H</i>-benzimidazole Derivatives against Phytopathogenic Fungi in Vitro

Bai, Yu-Bin; Zhang, Anling; Tang, Jiang‐Jiang; Gao, Jin‐Ming

doi:10.1021/jf3053934

Cited by 111 publications

(69 citation statements)

References 19 publications

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“…Generally, electron-withdrawing substituents such as -X (X = F, Cl, Br or I), -CF 3 and -NO 2 , especially -X, remarkably enhanced the activity. On the contrary, electron-donating groups such as -CH 3 , o-OH, and p-OCH 3 result in the decrease of the activity in most cases. In addition, the position of substituents was able to significantly influence the activity also.…”

Section: Discussionmentioning

confidence: 94%

“…On the contrary, the presence of electron-donating groups like -CH 3 (19)(20)(21), o-OH (22), and p-OCH 3 (24) led to a decrease of the activity in most cases (Figure 2). 3 increases activity against all the fungi R = CF 3 increases activity against 6 of 7 the fungi R = OH decreases activity against 6 of 7 the fungi R = NO 2 or Me dereases activity against all the fungi R = F, Cl, CF 3 or NO 2 increases activity against 6 of 7 the fungi R =I increases activity against 5 of 7 the fungi R = Me dereases activity against all the fungi R = F or Cl increases activity against all the fungi R = Br, I or CF 3 increases activity against 6 of 7 the fungi R = NO 2 increases activity against 5 of 7 the fungi R = OH increases activity against 4 of 7 the fungi R = Me or MeO dereases activity against 6 of 7 the fungi…”

Section: Structure-activity Relationshipmentioning

confidence: 99%

“…Therefore, various plant fungicides are extensively used in current agriculture. However, many of the currently used antifungal agents have several shortcomings, such as affecting human health, environmental pollution and development of pathogen resistance [3]. Thus, the worsening problems of phytofungal disease control urgently necessitate the discovery and development of new antifungal agents for plant protection.…”

Section: Introductionmentioning

confidence: 99%

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2-(Substituted phenyl)-3,4-dihydroisoquinolin-2-iums as Novel Antifungal Lead Compounds: Biological Evaluation and Structure-Activity Relationships

et al. 2013

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Abstract:The title compounds are a class of structurally simple analogues of quaternary benzo [c]phenanthridine alkaloids (QBAs). In order to develop novel QBA-like antifungal drugs, in this study, 24 of the title compounds with various substituents on the N-phenyl ring were evaluated for bioactivity against seven phytopathogenic fungi using the mycelial growth rate method and their SAR discussed. Almost all the compounds showed definite activities in vitro against each of the test fungi at 50 μg/mL and a broad antifungal spectrum. In most cases, the mono-halogenated compounds 2-12 exhibited excellent activities superior to the QBAs sanguinarine and chelerythrine. Compound 8 possessed the strongest activities on each of the fungi with EC 50 values of 8.88-19.88 µg/mL and a significant concentration-dependent relationship. The SAR is as follows: the N-phenyl group is a high sensitive structural moiety for the activity and the characteristics and position of substituents intensively influence the activity. Generally, electron-withdrawing substituents remarkably enhance the activity while electron-donating substituents cause a decrease of the activity. In most cases, ortha-and para-halogenated isomers were more active than the corresponding m-halogenated isomers. Thus, the title compounds emerged as promising lead compounds for the development of novel biomimetic antifungal

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Section: Discussionmentioning

confidence: 94%

Section: Structure-activity Relationshipmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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2-(Substituted phenyl)-3,4-dihydroisoquinolin-2-iums as Novel Antifungal Lead Compounds: Biological Evaluation and Structure-Activity Relationships

et al. 2013

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“…The presence of benzimidazole moiety also inflicted positive effects on the overall results as supported by Bai et al 21 . On the other hand there is no specific bioactivity of the compounds with imidazole and 1,2,4-triazole ring in the structure and this may be due to very low lipophilicity (negative log P) of the compounds, because of two highly hydrophilic rings in a single structure.…”

Section: Antifungal Activitymentioning

confidence: 64%

Synthesis and in Silico Analysis of Novel 1,2,4- Triazolylamides as Potential Antifungals

Gumber¹,

Sidhu²,

Sharma³

et al. 2017

Orient. J. Chem

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The lead hybridization concept was used to synthesize the series of 40 novel compounds having a 1,2,4-triazole moiety allied to various bioactive amines via carboxamide linkage. One pot two step reaction protocol was followed using K 2 CO 3 as novel and efficient catalyst. The titled compounds were made through preliminary screening for antifungal potential against various phytopathogenic fungi. Compounds 1a, 5a, 9a, 5b and 9b showed appreciable fungitoxicity against most of the test fungi. The best result was shown by compound 1a against Drechslera oryzae, which was comparable to the standard triazole fungicide, propiconazole. Lipophilicity (log P) was taken as critical factor that amend the bio-efficacy of the test compounds.

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“…Antifungal activities were screened as described by previous researchers 31,32) and evaluated against three pathogenic fungi-B. cinerea, R. solani and C. capsici-in vitro with a mycelial growth test on potato sucrose agar (PSA) medium.…”

Section: In Vitro Antifungal Bioassaymentioning

confidence: 99%

Synthesis and fungicidal activity of phenylhydrazone derivatives containing two carbonic acid ester groups

Wang

Chen

et al. 2017

J. Pestic. Sci.

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Substituted phenylhydrazone moieties and two carbonate groups were merged in one molecule scaffold to obtain 48 novel compounds. 1 H and 13 C NMR, MS, elemental analysis, and X-ray single-crystal diffraction were used to confirm their structures. Bioassay results revealed that some of the compounds have strong antifungal activities against Botrytis cinerea, Rhizoctonia solani, and Colletotrichum capsici (especially Rhizoctonia solani). Compound 5H 1 is the most promising of the tested compounds against R. solani with an EC 50 value of 1.91 mg/L, which is comparable with the positive control fungicide drazoxolon (1.94 mg/L). The structure-activity relationships against R. solani formed three rules: 1) small carbonate groups may improve the antifungal activity of the title compounds; 2) electron-withdrawing groups at the phenyl ring of phenylhydrazone are preferable to their non-substituted counterparts; and 3) halogen at the para position is more beneficial than at the ortho or meta position.

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Synthesis and Antifungal Activity of 2-Chloromethyl-1H-benzimidazole Derivatives against Phytopathogenic Fungi in Vitro

Cited by 111 publications

References 19 publications

2-(Substituted phenyl)-3,4-dihydroisoquinolin-2-iums as Novel Antifungal Lead Compounds: Biological Evaluation and Structure-Activity Relationships

2-(Substituted phenyl)-3,4-dihydroisoquinolin-2-iums as Novel Antifungal Lead Compounds: Biological Evaluation and Structure-Activity Relationships

Synthesis and in Silico Analysis of Novel 1,2,4- Triazolylamides as Potential Antifungals

Synthesis and fungicidal activity of phenylhydrazone derivatives containing two carbonic acid ester groups

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