Facile synthesis, crystal structure, quantum calculation, and biological evaluations of novel selenenyl sulfide compounds as potential agrochemicals
BACKGROUND In order to design compounds with fresh molecular skeleton to break through the limitation of available agrochemicals, a series of 36 novel selenenyl sulfide compounds were chemically synthesized, and their biological activities were fully evaluated against tobacco mosaic virus (TMV), 14...
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Veröffentlicht in: | Pest management science 2023-05, Vol.79 (5), p.1885-1896 |
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creator | Shang, Ming‐Hao Sun, Xue‐Wen Wang, Hai‐Lian Li, Hao‐Ran Zhang, Jia‐Shuang Wang, Li‐Zhong Yu, Shu‐Jing Zhang, Xiao Xiong, LI‐Xia Li, Yong‐Hong Niu, Cong‐Wei Wang, Jian‐Guo |
description | BACKGROUND
In order to design compounds with fresh molecular skeleton to break through the limitation of available agrochemicals, a series of 36 novel selenenyl sulfide compounds were chemically synthesized, and their biological activities were fully evaluated against tobacco mosaic virus (TMV), 14 plant pathogenic fungi, three insect species and plant acetohydroxyacid synthase (AHAS).
RESULTS
All the target compounds were characterized by proton nuclear magnetic resonance (1H‐NMR), carbon‐13 (13C)‐NMR, selenium‐77 (77Se)‐NMR, and high‐resolution mass spectrometry (HRMS). The crystal structure of 10j indicated that the Se–S bond was successfully constructed. Compounds 10d, 10h, 10s, 10u, 10aa, 10ac, 10ae, 10ag, and 10ai exhibited 40%, 43%, 39%, 41%, 47%, 46%, 47%, 42%, and 39% anti‐TMV activities at 500 mg L−1, better than that of ribavirin. The median effective concentration (EC50) against Sclerotinia sclerotiorum of 10ac was 6.69 mg L−1 and EC50 values against Physalospora piricola and Pyricularia grisea of 10z were 12.25 mg L−1 and 15.27 mg L−1, respectively, superior to the corresponding values of chlorothalonil. Compounds 10c and 10v demonstrated 100% larvicidal activity against Culex pipiens pallens at 5 mg L−1, while 10a displayed 100% insecticidal activity against Mythimna separata at 200 mg L−1. Compounds 10c, 10j, and 10o showed > 60% inhibitions against plant AHAS at 10 μmol L−1. From the quantum calculation, highest occupied molecular orbital (HOMO) was considered as a factor that affects the anti‐TMV activity.
CONCLUSION
The preliminary results suggested that more efforts should be devoted to exploring the selenenyl sulfides for the discovery of new leads of antiviral agent, fungicide, insecticide or AHAS inhibitors as potential agrochemicals for crop protection. © 2023 Society of Chemical Industry.
A series of novel selenenyl sulfide compounds were chemically synthesized and the biological activities were evaluated for the discovery of novel agrochemicals with new chemical skeleton. |
doi_str_mv | 10.1002/ps.7382 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2769997827</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2769997827</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3452-93d7690cbd21f063d480f0ad0d71609806c2c8876b8aa31414ec74ff2cdbc3913</originalsourceid><addsrcrecordid>eNp1kd9qFTEQhxdRbK3iG0jACwXPqfmz3U0uS7EqFBRU8G7JJrNtSjbZZpLKvocPbE5P7YXg1Qwz33yE_JrmJaPHjFL-fsHjXkj-qDlkJ7zbtkrJxw-9_HnQPEO8ppQqpfjT5kB0fb2S8rD5fa6N80BwDfkK0OGGmLRi1p5gTsXkkmBDbooOuczEaG-K19nFsCE6WDK66OOlq3MCt9qXuxWSOJEQb6E6wEOAsNau-MlZICbOSyzBItFIlpghZFev9WWK5grmnQqfN0-mWuDFfT1qfpx_-H72aXvx5ePns9OLrRHtCd8qYftOUTNazibaCdtKOlFtqe1ZR5WkneFGyr4bpdaCtawF07fTxI0djVBMHDVv994lxZsCmIfZoQHvdYBYcOBVr1QveV_R1_-g17GkUF9XKSVE_X3BK_VmT5kUERNMw5LcrNM6MDrsghoWHHZBVfLVva-MM9gH7m8yFXi3B37VeNb_eYav3-50fwD5qp6b</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2793373832</pqid></control><display><type>article</type><title>Facile synthesis, crystal structure, quantum calculation, and biological evaluations of novel selenenyl sulfide compounds as potential agrochemicals</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Shang, Ming‐Hao ; Sun, Xue‐Wen ; Wang, Hai‐Lian ; Li, Hao‐Ran ; Zhang, Jia‐Shuang ; Wang, Li‐Zhong ; Yu, Shu‐Jing ; Zhang, Xiao ; Xiong, LI‐Xia ; Li, Yong‐Hong ; Niu, Cong‐Wei ; Wang, Jian‐Guo</creator><creatorcontrib>Shang, Ming‐Hao ; Sun, Xue‐Wen ; Wang, Hai‐Lian ; Li, Hao‐Ran ; Zhang, Jia‐Shuang ; Wang, Li‐Zhong ; Yu, Shu‐Jing ; Zhang, Xiao ; Xiong, LI‐Xia ; Li, Yong‐Hong ; Niu, Cong‐Wei ; Wang, Jian‐Guo</creatorcontrib><description>BACKGROUND
In order to design compounds with fresh molecular skeleton to break through the limitation of available agrochemicals, a series of 36 novel selenenyl sulfide compounds were chemically synthesized, and their biological activities were fully evaluated against tobacco mosaic virus (TMV), 14 plant pathogenic fungi, three insect species and plant acetohydroxyacid synthase (AHAS).
RESULTS
All the target compounds were characterized by proton nuclear magnetic resonance (1H‐NMR), carbon‐13 (13C)‐NMR, selenium‐77 (77Se)‐NMR, and high‐resolution mass spectrometry (HRMS). The crystal structure of 10j indicated that the Se–S bond was successfully constructed. Compounds 10d, 10h, 10s, 10u, 10aa, 10ac, 10ae, 10ag, and 10ai exhibited 40%, 43%, 39%, 41%, 47%, 46%, 47%, 42%, and 39% anti‐TMV activities at 500 mg L−1, better than that of ribavirin. The median effective concentration (EC50) against Sclerotinia sclerotiorum of 10ac was 6.69 mg L−1 and EC50 values against Physalospora piricola and Pyricularia grisea of 10z were 12.25 mg L−1 and 15.27 mg L−1, respectively, superior to the corresponding values of chlorothalonil. Compounds 10c and 10v demonstrated 100% larvicidal activity against Culex pipiens pallens at 5 mg L−1, while 10a displayed 100% insecticidal activity against Mythimna separata at 200 mg L−1. Compounds 10c, 10j, and 10o showed > 60% inhibitions against plant AHAS at 10 μmol L−1. From the quantum calculation, highest occupied molecular orbital (HOMO) was considered as a factor that affects the anti‐TMV activity.
CONCLUSION
The preliminary results suggested that more efforts should be devoted to exploring the selenenyl sulfides for the discovery of new leads of antiviral agent, fungicide, insecticide or AHAS inhibitors as potential agrochemicals for crop protection. © 2023 Society of Chemical Industry.
A series of novel selenenyl sulfide compounds were chemically synthesized and the biological activities were evaluated for the discovery of novel agrochemicals with new chemical skeleton.</description><identifier>ISSN: 1526-498X</identifier><identifier>EISSN: 1526-4998</identifier><identifier>DOI: 10.1002/ps.7382</identifier><identifier>PMID: 36700288</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>Acetohydroxyacid synthase ; Agrochemicals ; AHAS inhibition ; Animals ; antifungal activity ; antiviral activity ; Antiviral Agents ; Chlorothalonil ; Crystal structure ; Drug Design ; Fungicides ; Fungicides, Industrial - chemistry ; Insecticides ; Insecticides - chemistry ; Insects ; larvicidal activity ; Mass spectrometry ; Mass spectroscopy ; Mathematical analysis ; Molecular orbitals ; Molecular Structure ; Moths ; NMR ; Nuclear magnetic resonance ; Plant protection ; Ribavirin ; selenenyl sulfide ; Selenium ; Structure-Activity Relationship ; Sulfide compounds ; Sulfides ; Sulfides - pharmacology ; Tobacco ; Tobacco Mosaic Virus ; Viruses</subject><ispartof>Pest management science, 2023-05, Vol.79 (5), p.1885-1896</ispartof><rights>2023 Society of Chemical Industry.</rights><rights>Copyright © 2023 Society of Chemical Industry</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3452-93d7690cbd21f063d480f0ad0d71609806c2c8876b8aa31414ec74ff2cdbc3913</citedby><cites>FETCH-LOGICAL-c3452-93d7690cbd21f063d480f0ad0d71609806c2c8876b8aa31414ec74ff2cdbc3913</cites><orcidid>0000-0001-7577-1502 ; 0000-0003-4754-1245</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fps.7382$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fps.7382$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36700288$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shang, Ming‐Hao</creatorcontrib><creatorcontrib>Sun, Xue‐Wen</creatorcontrib><creatorcontrib>Wang, Hai‐Lian</creatorcontrib><creatorcontrib>Li, Hao‐Ran</creatorcontrib><creatorcontrib>Zhang, Jia‐Shuang</creatorcontrib><creatorcontrib>Wang, Li‐Zhong</creatorcontrib><creatorcontrib>Yu, Shu‐Jing</creatorcontrib><creatorcontrib>Zhang, Xiao</creatorcontrib><creatorcontrib>Xiong, LI‐Xia</creatorcontrib><creatorcontrib>Li, Yong‐Hong</creatorcontrib><creatorcontrib>Niu, Cong‐Wei</creatorcontrib><creatorcontrib>Wang, Jian‐Guo</creatorcontrib><title>Facile synthesis, crystal structure, quantum calculation, and biological evaluations of novel selenenyl sulfide compounds as potential agrochemicals</title><title>Pest management science</title><addtitle>Pest Manag Sci</addtitle><description>BACKGROUND
In order to design compounds with fresh molecular skeleton to break through the limitation of available agrochemicals, a series of 36 novel selenenyl sulfide compounds were chemically synthesized, and their biological activities were fully evaluated against tobacco mosaic virus (TMV), 14 plant pathogenic fungi, three insect species and plant acetohydroxyacid synthase (AHAS).
RESULTS
All the target compounds were characterized by proton nuclear magnetic resonance (1H‐NMR), carbon‐13 (13C)‐NMR, selenium‐77 (77Se)‐NMR, and high‐resolution mass spectrometry (HRMS). The crystal structure of 10j indicated that the Se–S bond was successfully constructed. Compounds 10d, 10h, 10s, 10u, 10aa, 10ac, 10ae, 10ag, and 10ai exhibited 40%, 43%, 39%, 41%, 47%, 46%, 47%, 42%, and 39% anti‐TMV activities at 500 mg L−1, better than that of ribavirin. The median effective concentration (EC50) against Sclerotinia sclerotiorum of 10ac was 6.69 mg L−1 and EC50 values against Physalospora piricola and Pyricularia grisea of 10z were 12.25 mg L−1 and 15.27 mg L−1, respectively, superior to the corresponding values of chlorothalonil. Compounds 10c and 10v demonstrated 100% larvicidal activity against Culex pipiens pallens at 5 mg L−1, while 10a displayed 100% insecticidal activity against Mythimna separata at 200 mg L−1. Compounds 10c, 10j, and 10o showed > 60% inhibitions against plant AHAS at 10 μmol L−1. From the quantum calculation, highest occupied molecular orbital (HOMO) was considered as a factor that affects the anti‐TMV activity.
CONCLUSION
The preliminary results suggested that more efforts should be devoted to exploring the selenenyl sulfides for the discovery of new leads of antiviral agent, fungicide, insecticide or AHAS inhibitors as potential agrochemicals for crop protection. © 2023 Society of Chemical Industry.
A series of novel selenenyl sulfide compounds were chemically synthesized and the biological activities were evaluated for the discovery of novel agrochemicals with new chemical skeleton.</description><subject>Acetohydroxyacid synthase</subject><subject>Agrochemicals</subject><subject>AHAS inhibition</subject><subject>Animals</subject><subject>antifungal activity</subject><subject>antiviral activity</subject><subject>Antiviral Agents</subject><subject>Chlorothalonil</subject><subject>Crystal structure</subject><subject>Drug Design</subject><subject>Fungicides</subject><subject>Fungicides, Industrial - chemistry</subject><subject>Insecticides</subject><subject>Insecticides - chemistry</subject><subject>Insects</subject><subject>larvicidal activity</subject><subject>Mass spectrometry</subject><subject>Mass spectroscopy</subject><subject>Mathematical analysis</subject><subject>Molecular orbitals</subject><subject>Molecular Structure</subject><subject>Moths</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Plant protection</subject><subject>Ribavirin</subject><subject>selenenyl sulfide</subject><subject>Selenium</subject><subject>Structure-Activity Relationship</subject><subject>Sulfide compounds</subject><subject>Sulfides</subject><subject>Sulfides - pharmacology</subject><subject>Tobacco</subject><subject>Tobacco Mosaic Virus</subject><subject>Viruses</subject><issn>1526-498X</issn><issn>1526-4998</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kd9qFTEQhxdRbK3iG0jACwXPqfmz3U0uS7EqFBRU8G7JJrNtSjbZZpLKvocPbE5P7YXg1Qwz33yE_JrmJaPHjFL-fsHjXkj-qDlkJ7zbtkrJxw-9_HnQPEO8ppQqpfjT5kB0fb2S8rD5fa6N80BwDfkK0OGGmLRi1p5gTsXkkmBDbooOuczEaG-K19nFsCE6WDK66OOlq3MCt9qXuxWSOJEQb6E6wEOAsNau-MlZICbOSyzBItFIlpghZFev9WWK5grmnQqfN0-mWuDFfT1qfpx_-H72aXvx5ePns9OLrRHtCd8qYftOUTNazibaCdtKOlFtqe1ZR5WkneFGyr4bpdaCtawF07fTxI0djVBMHDVv994lxZsCmIfZoQHvdYBYcOBVr1QveV_R1_-g17GkUF9XKSVE_X3BK_VmT5kUERNMw5LcrNM6MDrsghoWHHZBVfLVva-MM9gH7m8yFXi3B37VeNb_eYav3-50fwD5qp6b</recordid><startdate>202305</startdate><enddate>202305</enddate><creator>Shang, Ming‐Hao</creator><creator>Sun, Xue‐Wen</creator><creator>Wang, Hai‐Lian</creator><creator>Li, Hao‐Ran</creator><creator>Zhang, Jia‐Shuang</creator><creator>Wang, Li‐Zhong</creator><creator>Yu, Shu‐Jing</creator><creator>Zhang, Xiao</creator><creator>Xiong, LI‐Xia</creator><creator>Li, Yong‐Hong</creator><creator>Niu, Cong‐Wei</creator><creator>Wang, Jian‐Guo</creator><general>John Wiley & Sons, Ltd</general><general>Wiley Subscription Services, Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QR</scope><scope>7SS</scope><scope>7ST</scope><scope>7T7</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>SOI</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7577-1502</orcidid><orcidid>https://orcid.org/0000-0003-4754-1245</orcidid></search><sort><creationdate>202305</creationdate><title>Facile synthesis, crystal structure, quantum calculation, and biological evaluations of novel selenenyl sulfide compounds as potential agrochemicals</title><author>Shang, Ming‐Hao ; Sun, Xue‐Wen ; Wang, Hai‐Lian ; Li, Hao‐Ran ; Zhang, Jia‐Shuang ; Wang, Li‐Zhong ; Yu, Shu‐Jing ; Zhang, Xiao ; Xiong, LI‐Xia ; Li, Yong‐Hong ; Niu, Cong‐Wei ; Wang, Jian‐Guo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3452-93d7690cbd21f063d480f0ad0d71609806c2c8876b8aa31414ec74ff2cdbc3913</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acetohydroxyacid synthase</topic><topic>Agrochemicals</topic><topic>AHAS inhibition</topic><topic>Animals</topic><topic>antifungal activity</topic><topic>antiviral activity</topic><topic>Antiviral Agents</topic><topic>Chlorothalonil</topic><topic>Crystal structure</topic><topic>Drug Design</topic><topic>Fungicides</topic><topic>Fungicides, Industrial - chemistry</topic><topic>Insecticides</topic><topic>Insecticides - chemistry</topic><topic>Insects</topic><topic>larvicidal activity</topic><topic>Mass spectrometry</topic><topic>Mass spectroscopy</topic><topic>Mathematical analysis</topic><topic>Molecular orbitals</topic><topic>Molecular Structure</topic><topic>Moths</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Plant protection</topic><topic>Ribavirin</topic><topic>selenenyl sulfide</topic><topic>Selenium</topic><topic>Structure-Activity Relationship</topic><topic>Sulfide compounds</topic><topic>Sulfides</topic><topic>Sulfides - pharmacology</topic><topic>Tobacco</topic><topic>Tobacco Mosaic Virus</topic><topic>Viruses</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shang, Ming‐Hao</creatorcontrib><creatorcontrib>Sun, Xue‐Wen</creatorcontrib><creatorcontrib>Wang, Hai‐Lian</creatorcontrib><creatorcontrib>Li, Hao‐Ran</creatorcontrib><creatorcontrib>Zhang, Jia‐Shuang</creatorcontrib><creatorcontrib>Wang, Li‐Zhong</creatorcontrib><creatorcontrib>Yu, Shu‐Jing</creatorcontrib><creatorcontrib>Zhang, Xiao</creatorcontrib><creatorcontrib>Xiong, LI‐Xia</creatorcontrib><creatorcontrib>Li, Yong‐Hong</creatorcontrib><creatorcontrib>Niu, Cong‐Wei</creatorcontrib><creatorcontrib>Wang, Jian‐Guo</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Chemoreception Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Environment Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Environment Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Pest management science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shang, Ming‐Hao</au><au>Sun, Xue‐Wen</au><au>Wang, Hai‐Lian</au><au>Li, Hao‐Ran</au><au>Zhang, Jia‐Shuang</au><au>Wang, Li‐Zhong</au><au>Yu, Shu‐Jing</au><au>Zhang, Xiao</au><au>Xiong, LI‐Xia</au><au>Li, Yong‐Hong</au><au>Niu, Cong‐Wei</au><au>Wang, Jian‐Guo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Facile synthesis, crystal structure, quantum calculation, and biological evaluations of novel selenenyl sulfide compounds as potential agrochemicals</atitle><jtitle>Pest management science</jtitle><addtitle>Pest Manag Sci</addtitle><date>2023-05</date><risdate>2023</risdate><volume>79</volume><issue>5</issue><spage>1885</spage><epage>1896</epage><pages>1885-1896</pages><issn>1526-498X</issn><eissn>1526-4998</eissn><abstract>BACKGROUND
In order to design compounds with fresh molecular skeleton to break through the limitation of available agrochemicals, a series of 36 novel selenenyl sulfide compounds were chemically synthesized, and their biological activities were fully evaluated against tobacco mosaic virus (TMV), 14 plant pathogenic fungi, three insect species and plant acetohydroxyacid synthase (AHAS).
RESULTS
All the target compounds were characterized by proton nuclear magnetic resonance (1H‐NMR), carbon‐13 (13C)‐NMR, selenium‐77 (77Se)‐NMR, and high‐resolution mass spectrometry (HRMS). The crystal structure of 10j indicated that the Se–S bond was successfully constructed. Compounds 10d, 10h, 10s, 10u, 10aa, 10ac, 10ae, 10ag, and 10ai exhibited 40%, 43%, 39%, 41%, 47%, 46%, 47%, 42%, and 39% anti‐TMV activities at 500 mg L−1, better than that of ribavirin. The median effective concentration (EC50) against Sclerotinia sclerotiorum of 10ac was 6.69 mg L−1 and EC50 values against Physalospora piricola and Pyricularia grisea of 10z were 12.25 mg L−1 and 15.27 mg L−1, respectively, superior to the corresponding values of chlorothalonil. Compounds 10c and 10v demonstrated 100% larvicidal activity against Culex pipiens pallens at 5 mg L−1, while 10a displayed 100% insecticidal activity against Mythimna separata at 200 mg L−1. Compounds 10c, 10j, and 10o showed > 60% inhibitions against plant AHAS at 10 μmol L−1. From the quantum calculation, highest occupied molecular orbital (HOMO) was considered as a factor that affects the anti‐TMV activity.
CONCLUSION
The preliminary results suggested that more efforts should be devoted to exploring the selenenyl sulfides for the discovery of new leads of antiviral agent, fungicide, insecticide or AHAS inhibitors as potential agrochemicals for crop protection. © 2023 Society of Chemical Industry.
A series of novel selenenyl sulfide compounds were chemically synthesized and the biological activities were evaluated for the discovery of novel agrochemicals with new chemical skeleton.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><pmid>36700288</pmid><doi>10.1002/ps.7382</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0001-7577-1502</orcidid><orcidid>https://orcid.org/0000-0003-4754-1245</orcidid></addata></record> |
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subjects | Acetohydroxyacid synthase Agrochemicals AHAS inhibition Animals antifungal activity antiviral activity Antiviral Agents Chlorothalonil Crystal structure Drug Design Fungicides Fungicides, Industrial - chemistry Insecticides Insecticides - chemistry Insects larvicidal activity Mass spectrometry Mass spectroscopy Mathematical analysis Molecular orbitals Molecular Structure Moths NMR Nuclear magnetic resonance Plant protection Ribavirin selenenyl sulfide Selenium Structure-Activity Relationship Sulfide compounds Sulfides Sulfides - pharmacology Tobacco Tobacco Mosaic Virus Viruses |
title | Facile synthesis, crystal structure, quantum calculation, and biological evaluations of novel selenenyl sulfide compounds as potential agrochemicals |
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