CHEMISTRY & BIODIVERSITY
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2022
·Vol. 19
·期 9
·e202200580
·
IF 2.745
Zhiping Che,Yibo Liu,Luyao Chen,Puhou Xing,Xiangdong Li,Xiaobo Huang,Shengming Liu,Genqiang Chen,Xiaomin Lin,Yuee Tian
In order to explore novel natural product-based anti-oomycete and nematicidal agents, sixteen unreported 2-sulfonyloxyhinokitiol derivatives were prepared using the principle of active splicing, and structurally confirmed by proton nuclear magnetic resonance ( 1 H-NMR), carbon-13 nuclear magnetic resonance ( 13 C-NMR), high-resolution mass spectrometry (HRMS), and melting point. Moreover, we evaluated the title compounds as anti-oomycete and nematicidal agents against two serious agricultural pests of Phytophthora capsici and Meloidogyne incongnita . Among the sixteen hinokitiol esters tested: (1) Compounds 3a and 3m exhibited the most potent anti-oomycete activity compared to zoxamide against P. capsici , and the median effective concentration (EC 50 ) values of 3a , 3m , and zoxamide were 18.64, 21.11, and 23.15 mg/L, respectively; Further studies showed that the existence of seven membered ring and carbonyl group was the necessary condition for the high anti-oomycete activity of hinokitiol. (2) Compounds 3n and 3p exhibited more promising nematicidal activity than hinokitiol, and the median lethal concentration (LC 50 ) values of 3n , 3p and 1 against M. incongnita were 0.2111, 0.2079, and 0.3933 mg/L, respectively. This result will pave the way for further modification of hinokitiol to develop potential new fungicides and nematicides. Graphical
研究领域:
植物化学
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农药科学
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分子生物学
✓ 已验证
DOI
高影响因子
CHEMISTRY & BIODIVERSITY
·
2021
·Vol. 18
·期 9
·e2100329
·
IF 2.408
Genqiang Chen,Lina Zhu,Jiaxuan He,Song Zhang,Yuanhao Li,Xiaolong Guo,Di Sun,Yuee Tian,Shengming Liu,Xiaobo Huang,Zhiping Che
Endeavor to discover biorational natural products-based fungicides, two series (26) of novel 1-sulfonyloxy/acyloxydihydroeugenol derivatives ( 3a – p and 5a – j ) were prepared and assessed for their fungicidal activity against P. capsici Leonian, in vitro . Results of fungicidal activity revealed that, among all compounds, especially compounds 3a , 5c , and 5e displayed the most potent anti-oomycete activity against P. capsici with EC 50 values of 69.33, 68.81, and 67.77 mg/L, respectively. Overall, the anti-oomycete activities of 1-acyloxydihydroeugenol derivatives ( 5a – j ) were higher than that of 1-sulfonyloxydihydroeugenol derivatives ( 3a – p ). It is proved that the introduction of the acyl group at hydroxy position of dihydroeugenol is more beneficial to improve its anti-oomycete activity than that of the sulfonyl group. These preliminary results will pave the way for further modification of dihydroeugenol in the development of potential new fungicides. Graphical
研究领域:
植物化学
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农药科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
CHEMISTRY & BIODIVERSITY
·
2025
·
IF 2.5
Huilu Sun,Ruxue Wei,Genqiang Chen,Zhiping Che,Xiaobo Huang,Yingwu Chen,Yuee Tian
Eugenol is the main component of clove basil oil extracted from plants such as Syzygium aromaticum and Ocimum gratissimum . To discover biorational natural product-based pesticides, a series of eugenol/dihydroeugenol derivatives containing carbamate moiety were prepared by introducing an active aminooyloxy group at its C1 hydroxy position, and their structures were well characterized by proton nuclear magnetic resonance ( 1 H NMR), carbon-13 NMR ( 13 C NMR), high-resolution mass spectrometry, and melting point. Bioactivities of these target compounds as anti-oomycete and anti-fungal agents against two serious agricultural pests, Phytophthora capsici and Fusarium graminearum were evaluated. Among assessed compounds: (1) Title compounds 1b and 2b showed significant anti-fungal against F. graminearum , with half maximal effective concentration values of 29.13 and 35.04 mg/L, respectively. (2) The title compounds have obvious selectivity, and their anti-fungal activity is significantly better than their anti-oomycete activity. (3) The anti-oomycete and anti-fungal activities of introducing the aminoalkyloyloxy group at the C1 hydroxyl position of eugenol or dihydroeugenol are significantly better than that of introducing the aminoaryloyloxy group. (4) The presence of a double bond is beneficial for increasing anti-fungal activity, and the reduction of a double bond is beneficial for increasing anti-oomycete activity. Graphical
研究领域:
植物化学
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农药科学
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生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
CHEMISTRY & BIODIVERSITY
·
2022
·Vol. 19
·期 4
·e202101039
·
IF 2.745
Zhiping Che,Yuanhao Li,Xiaolong Guo,Jiaxuan He,Song Zhang,Lina Zhu,Yibo Liu,Ruxue Wei,Yingjun Yang,Xiaobo Huang,Shengming Liu,Genqiang Chen,Yuee Tian
In order to discover highly active fungicides, sixteen novel sulfonate derivatives of Fenjuntong were synthesized by structural modification of 2′-hydroxybutyrophenone, and their anti-oomycete activity against Phytophthora capsici Leonian was determined in this study. Among all tested compounds, compound 3b displayed more significant anti-oomycete activity than the precursor Fenjuntong against P. capsici , and the EC 50 values of 3b and Fenjuntong were 84.50 and 517.25 mg/L, respectively. By comparing the anti-oomycete activity of compounds 3a – p , I-a – p , and II-a – p , the following conclusions were drawn: (1) Hydroxy group is well tolerated, and sulfonylation of hydroxy group enhances its anti-oomycete activity. (2) The proper length of the ketone carbonyl chain is very important for their anti-oomycete activity. (3) The presence of a site methoxy group in the structural skeleton is closely related to the anti-oomycete activity. These important results will pave the way for further modification of Fenjuntong to develop potential new fungicides. Graphical
研究领域:
农药化学
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植物病理学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
PEST MANAGEMENT SCIENCE
·
2022
·Vol. 78
·期 8
·3442-3455
·
IF 4.462
Zhiping Che,Xiaolong Guo,Yuanhao Li,Song Zhang,Lina Zhu,Jiaxuan He,Di Sun,Yihao Guo,Yibo Liu,Ruxue Wei,Xiaobo Huang,Shengming Liu,Genqiang Chen,Yuee Tian
Background Paeonol is extracted and isolated as a rich and sustainable natural bioresource from the root bark of Paeonia suffruticosa , the derivatives of which exhibit numerous biological activities. It is well known that ester compounds play a very important role in pest control, such as organophosphorus, carbamate and pyrethroid pesticides. Results To discover biorational natural product-based pesticides, three series of (60) paeonol ester derivatives ( 7a–t , 8g , p , 9g , p , 10g–j , n–u , 11g , u , 12g , u , 13a–p , 14b , c , and 15b , c ) were prepared by structural modification of paeonol, and their structures were well characterized by proton nuclear magnetic resonance ( 1 H-NMR), carbon-13 nuclear magnetic resonance ( 13 C-NMR), high-resolution mass spectrometry (HRMS), and melting point. Furthermore, we assessed the compounds as insecticidal, nematicidal, and anti-oomycete agents against three serious agricultural pests, Mythimna separata , Heterodera glycines , and Phytophthora capsici . Among all tested compounds: (i) compound 8p showed more significant insecticidal activity than toosendanin, and the final mortality rates of 8p and toosendanin against M. separata (1 mg mL −1 ) were 70.4%, and 51.9%, respectively; (ii) compound 7a exhibited more promising nematicidal activity than paeonol, and the median lethal concentration (LC 50 ) values of 7a and 1 against H. glycines were 15.47 and 50.80 mg L −1 , respectively; (iii) compounds 7n and 13m displayed more significant anti-oomycete activity compared to zoxamide against Phytophthora capsici , and the median effective concentration (EC 50 ) values of 7n , 13m , and zoxamide were 23.72, 24.51, and 26.87 mg L −1 , respectively; and the protective effect of the compounds against Phytophthora capsici in vivo further confirmed the effectiveness of the agents. Conclusion This study suggested that the introduction of a nitro at the C5 or C3 position of paeonol could improve its bioactivity against M. separata , H. glycines , and Phytophthora capsici . © 2022 Society of Chemical Industry.
研究领域:
植物化学
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农药科学
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分子生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
·
2021
·
IF 1.571
Gen-Qiang Chen,Di Sun,Jin-Ming Yang,Song Zhang,Yue-E Tian,Zhi-Ping Che,Sheng-Ming Liu,Jia Jiang,Xiao-Min Lin
Two series of sulfonate derivatives of carvacrol and thymol were synthesized and screened in vitro for their anti-oomycete activity against Phytophthora capsici, respectively. Among all of 32 derivatives, five compounds 3a, 4a, 4k, 3n, and 4n exhibited more potent anti-oomycete activity against P. capsici with EC50 values of 66.66, 62.94, 68.65, 61.24, and 52.91 mg/L, respectively. This suggested that introduction of different substitutions at the hydroxyl position of 1/2 could have remarkable effect on anti-oomycete activity. Overall, when R1 = isopropyl and R2 = methyl, the anti-oomycete activities of the compounds were higher than that of the corresponding compounds of R1 = methyl and R2 = isopropyl.
研究领域:
植物化学
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农药科学
·
微生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2025
·
IF 6.2
Yibo Liu,Yuee Tian,Hong Peng,Fulong Zhang,Xiaobo Huang,Genqiang Chen,Lin Zhou,Zhiping Che
Paeonol is the main active ingredient in the Chinese medicinal herb peony root bark. To discover biorational natural product-based fungicides, 25 paeonol derivatives (5a–y) containing a pyrazole ring were designed and synthesized by ingeniously introducing a pyrazole five-membered heterocyclic ring, and their structures were well characterized by 1H NMR, 13C NMR, high-resolution mass spectrometer (HRMS), and m.p. The stereochemical configurations of six target compounds, 5c, 5f, 5g, 5o, 5s, and 5v, were unambiguously subjected to single-crystal X-ray diffraction. Furthermore, we evaluated the bioactivities of these target compounds as anti-oomycete and antifungal agents against two serious agricultural diseases, Phytophthora capsici and Fusarium graminearum. Among all tested compounds, (1) nine compounds 5b–d, 5f, 5g, 5r, 5s, 5u, 5w displayed promising anti-oomycete against P. capsici, with EC50 values ranging from 22.1 to 34.5 mg/L, and the protective effect of the target compounds against P. capsici in vivo further confirmed the above results. (2) Six compounds 5g, 5k, 5m, 5t, 5w, 5x displayed promising antifungal against F. graminearum, with EC50 values ranging from 38.2 to 86.0 mg/L. Moreover, some interesting results of structure–activity relationships were also observed. The results of this study pave the way for further design, synthesis, and development of paeonol derivatives as potential botanical anti-oomycete and antifungal agents in crop protection.
研究领域:
植物化学
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农药科学
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药物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING
·
2024
·Vol. 27
·期 19
·2816-2823
·
IF 1.6
Fei Hai,Ruxue Wei,Yan Li,Ruiguang Wang,Yuee Tian,Shengming Liu,Genqiang Chen,Zhiping Che
Background Developing high-efficiency and low-risk small-molecule green fungicide is the key to effective control of the plant pathogenic oomycetes. Indole is an important raw material for drug synthesis. Due to its unique structural skeleton, indole, and its derivatives have exhibited a wide range of biological activities. However, a study on the synthesis of novel indole derivatives as fungicidal agents against Phytophthora capsici has not yet been reported. Methods The important intermediates 2a-c and 3a-c were synthesized in high yields by Vilsmeier-Haack and Knoevenagel reactions with indole as the lead compound. Furthermore, different substituted benzenesulfonyl groups were introduced into the NH position of the indole ring, and twelve indole derivatives (I-a-l) were prepared. Their structures were well characterized by 1H NMR, HRMS, and melting point. Results The results showed that 2-[(N-(4-nitrobenzenesulfonyl)-indole-3)-methylene]-diethyl malonate (I-d) and 2-[(N-(4-nitrobenzenesulfonyl)-5-cyanoindole-3)-methylene]-diethyl malonate (I-l) showed more anti-oomycete activity against P. capsici than the commercialized fungicide zoxamide, with corresponding EC50 values of 26.53, 23.48 and 28.16 mg/L, respectively, and the protective effect of the compounds against P. capsici in vivo further confirmed the above results. Conclusion The preliminary structure-activity relationship showed that the formyl group modification at the C-3 position of the indole ring was acceptable, and the different anti-oomycete activities of R1 and R2 were significantly different, with R1 being 5-CN > H > 6-Me, and R2 being 4-NO2 > 3-NO2, H > 4-Me.
研究领域:
植物病理学
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有机化学
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药物化学
✓ 已验证
DOI
PubMed
高影响因子
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
·
2021
·
IF 1.571
Yue-E Tian,Di Sun,Xiao-Xiao Han,Jin-Ming Yang,Song Zhang,Nan-Nan Feng,Li-Na Zhu,Zhong-Yuan Xu,Zhi-Ping Che,Sheng-Ming Liu,Xiao-Min Lin,Jia Jiang,Gen-Qiang Chen
Three series of sulfonate derivatives of paeonol were synthesized and screened in vitro for their anti-oomycete activity against P. capsici, respectively. Among all the compounds, 4m displayed the best promising and pronounced anti-oomycete activity against P. capsici than zoxamide, with the EC50 values of 24.51 and 26.87 mg/L, respectively. The results show that acetyl and 4-OCH3 are two necessary groups. The existence of these two sites is closely related to the anti-oomycete activity. Relatively speaking, hydroxyl group is well tolerated, and the results showed that after modification of hydroxyl group with sulfonyl, the anti-oomycete activity was significantly increased.
研究领域:
植物化学
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农药科学
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药物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING
·
2022
·Vol. 25
·期 9
·1545-1551
·
IF 1.714
Chen Genqiang,Zhu Lina,He Jiaxuan,Zhang Song,Li Yuanhao,Guo Xiaolong,Sun Di,Tian Yuee,Liu Shengming,Huang Xiaobo,Che Zhiping
Background: Developing the high-efficiency and low-risk small-molecule greenfungicide is the key to effective control of the plant pathogenic oomycetes. Essential oils play a very important role in novel fungicide discovery for their unique sources and potential target sites. Eugenol,
a kind of plant essential oil, was mainly isolated from the unopened and dried flower buds of Syzygium aromaticum of the Myrtaceae family. Due to its unique structural skeleton, eugenol and its derivatives have exhibited a wide range of biological activities. However, a study on the synthesis
of novel 1-sulfonyloxy/acyloxyeugenol derivatives as fungicidal agents against Phytophthora capsici has not yet been reported. Methods: Twenty-six novel 1-sulfonyloxy/acyloxyeugenol derivatives (3a-p and 5a-j) were prepared and their structures were well characterized by 1H
NMR, HRMS, and m.p. Their fungicidal activity was evaluated against P. capsici by using the mycelial growth rate method. Results: To find novel natural-product-based fungicidal agents to control the plant pathogenic oomycetes, we herein designed and synthesized two series of novel 1-sulfonyloxy/acyloxyeugenol
derivatives (3a-p and 5a-j) as fungicidal agents against P. capsici Leonian, in vitro. Results of fungicidal activity revealed that, among all compounds, especially compounds 3a, 3f, and 3n displayed the most potent anti-oomycete activity against P. capsici with EC50 values of 79.05, 75.05,
and 70.80, respectively. Conclusion: The results revealed that the anti-oomycete activity of eugenol with the sulfonyloxy group was higher than that with the acyloxy group. It is suggested that the fungicidal activity of eugenol can be improved by introducing the sulfonyloxy group. This
will pave the way for further design, structural modification, and development of eugenol derivatives as fungicidal agents.
研究领域:
植物化学
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农药科学
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分子生物学
✓ 已验证
DOI
PubMed
高影响因子
NATURAL PRODUCT RESEARCH
·
2024
·
IF 1.9
Xiaofang Zhang,Xiaolong Guo,Wanying Yin,Ruiguang Wang,Yuee Tian,Huilu Sun,Shaobin Xu,Shaoyan Shuang,Xiaobo Huang,Genqiang Chen,Zhiping Che
To discover biorational natural product-based pesticides, a series of paeonol ester derivatives containing a Schiff base (6a-j, 7i,j, 8i,j, and 9i,j) were prepared, and their structures were well characterised by 1H NMR and HRMS. Furthermore, bioactivities of these compounds as anti-oomycete and anti-fungal agents against two serious agricultural diseases, Phytophthora capsici and Fusarium graminearum we assessed. Amongst evaluated compounds, 1) Compounds 6a and 6e displayed good anti-oomycete against P. capsici, with EC50 values of 116.50 and 88.86 mg/L, respectively. 2) Compounds 6e and 7i exhibited prominent anti-fungal against F. graminearum, with EC50 values of 66.73 and 29.33 mg/L, respectively. 3) This study suggested that the introduction of nitro at the C5 position of paeonol could improve its bioactivity against P. capsici and F. graminearum. The results of this study pave the way for further design and development of paeonol derivatives as plant anti-oomycetes and anti-fungal agents in crop protection.
研究领域:
植物化学
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农药学
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植物病理学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
INDUSTRIAL CROPS AND PRODUCTS
·
2024
·
IF 5.6
Yuee Tian,Wanying Yin,Ruiguang Wang,Huilu Sun,Shaobin Xu,Xiaobo Huang,Genqiang Chen,Zhiping Che
Quinine is the main alkaloids in the bark of Cinchona and its homologous plants of Rubiaceae. To discover biorational natural product-based pesticides, a series of 9 R -acyloxyquinine derivatives containing 1,3,4-oxadiazole moieties were prepared by ingeniously introducing an active ester group and a 1,3,4-oxadiazole five membered heterocyclic ring at its C-9 position, and their structures were well characterized by 1 H NMR, 13 C NMR, HRMS, and m.p. The stereochemical configuration of target compound 6 t was unambiguously subjected to single-crystal X-ray diffraction. Furthermore, bioactivities of these compounds as anti-oomycete and anti-fungal agents against two serious agricultural diseases, Phytophthora capsici and Fusarium graminearum we assessed. Among all tested compounds, 1) Compounds 6c and 6d displayed promising anti-oomycete against P. capsici , with EC 50 values of 38.42 and 35.49 mg/L, respectively. 2) Compound 6i exhibited promising anti-fungal against F. graminearum , with an EC 50 value of 29.92 mg/L. Moreover, some interesting results of structure-activity relationships were also observed. The results of this study pave the way for further design, structural modification, and development of quinine derivatives as plant anti-oomycetes and anti-fungal agents in crop protection.
研究领域:
植物化学
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农药科学
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药物化学
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）