Novel sulfonamides against

Thirty-four novel compounds were synthesized using chesulfamide (N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by 1H NMR, 13C NMR, MS and elemental analysis. Additionally, the structure of (1...
Ausführliche Beschreibung

Gespeichert in:

Autor*in:	Cai, Nan [verfasserIn] He, Lu [verfasserIn] Wang, Kai [verfasserIn] Feng, Zhihui [verfasserIn] Cui, Zining [verfasserIn] Ji, Mingshan [verfasserIn] Qi, Zhiqiu [verfasserIn] Qin, Peiwen [verfasserIn] Li, Xinghai [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2019

Schlagwörter:	Cycloalkylsulfonamides Reductive amination Fungicidal activity SAR Cross resistance

Übergeordnetes Werk:	Enthalten in: Bioorganic & medicinal chemistry letters - Amsterdam [u.a.] : Elsevier Science, 1991, 30
Übergeordnetes Werk:	volume:30

DOI / URN:	10.1016/j.bmcl.2019.126859

Katalog-ID:	ELV003488306

Internformat


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520			\|a Thirty-four novel compounds were synthesized using chesulfamide (N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by 1H NMR, 13C NMR, MS and elemental analysis. Additionally, the structure of (1S,2R)-2-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide (IV-9) was confirmed by X-ray single crystal diffraction. The mycelium inhibition tests, spore germination inhibition tests, tomato pot tests and field trials were performed against strains of B. cinerea. Bioassay results showed that most of target compounds had good fungicidal activity against B. cinerea, in particular, IV-9 exhibited similar or superior effects to procymidone, boscalid and pyrisoxazole in all in vitro and in vivo tests. Moreover, there was no positive cross-resistance found between the compound IV-9 and eight commercial fungicides (azoxystrobin, boscalid, chlorothalonil, diethofencarb, fludioxonil, procymidone, pyrimethanil and pyrisoxazole) in the cross-resistance validation test performed by an innovative method.
650		4	\|a Cycloalkylsulfonamides
650		4	\|a Reductive amination
650		4	\|a Fungicidal activity
650		4	\|a SAR
650		4	\|a Cross resistance
700	1		\|a He, Lu \|e verfasserin \|4 aut
700	1		\|a Wang, Kai \|e verfasserin \|4 aut
700	1		\|a Feng, Zhihui \|e verfasserin \|4 aut
700	1		\|a Cui, Zining \|e verfasserin \|4 aut
700	1		\|a Ji, Mingshan \|e verfasserin \|4 aut
700	1		\|a Qi, Zhiqiu \|e verfasserin \|4 aut
700	1		\|a Qin, Peiwen \|e verfasserin \|4 aut
700	1		\|a Li, Xinghai \|e verfasserin \|4 aut
773	0	8	\|i Enthalten in \|t Bioorganic & medicinal chemistry letters \|d Amsterdam [u.a.] : Elsevier Science, 1991 \|g 30 \|h Online-Ressource \|w (DE-627)306717522 \|w (DE-600)1501505-1 \|w (DE-576)110916573 \|x 1464-3405 \|7 nnns
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912			\|a GBV_ILN_22
912			\|a GBV_ILN_23
912			\|a GBV_ILN_24
912			\|a GBV_ILN_31
912			\|a GBV_ILN_32
912			\|a GBV_ILN_40
912			\|a GBV_ILN_60
912			\|a GBV_ILN_62
912			\|a GBV_ILN_63
912			\|a GBV_ILN_65
912			\|a GBV_ILN_69
912			\|a GBV_ILN_70
912			\|a GBV_ILN_73
912			\|a GBV_ILN_74
912			\|a GBV_ILN_90
912			\|a GBV_ILN_95
912			\|a GBV_ILN_100
912			\|a GBV_ILN_101
912			\|a GBV_ILN_105
912			\|a GBV_ILN_110
912			\|a GBV_ILN_150
912			\|a GBV_ILN_151
912			\|a GBV_ILN_224
912			\|a GBV_ILN_370
912			\|a GBV_ILN_602
912			\|a GBV_ILN_702
912			\|a GBV_ILN_2003
912			\|a GBV_ILN_2004
912			\|a GBV_ILN_2005
912			\|a GBV_ILN_2011
912			\|a GBV_ILN_2014
912			\|a GBV_ILN_2015
912			\|a GBV_ILN_2020
912			\|a GBV_ILN_2021
912			\|a GBV_ILN_2025
912			\|a GBV_ILN_2027
912			\|a GBV_ILN_2034
912			\|a GBV_ILN_2038
912			\|a GBV_ILN_2044
912			\|a GBV_ILN_2048
912			\|a GBV_ILN_2049
912			\|a GBV_ILN_2050
912			\|a GBV_ILN_2056
912			\|a GBV_ILN_2059
912			\|a GBV_ILN_2061
912			\|a GBV_ILN_2064
912			\|a GBV_ILN_2065
912			\|a GBV_ILN_2068
912			\|a GBV_ILN_2111
912			\|a GBV_ILN_2112
912			\|a GBV_ILN_2113
912			\|a GBV_ILN_2118
912			\|a GBV_ILN_2122
912			\|a GBV_ILN_2129
912			\|a GBV_ILN_2143
912			\|a GBV_ILN_2147
912			\|a GBV_ILN_2148
912			\|a GBV_ILN_2152
912			\|a GBV_ILN_2153
912			\|a GBV_ILN_2190
912			\|a GBV_ILN_2336
912			\|a GBV_ILN_2507
912			\|a GBV_ILN_2522
912			\|a GBV_ILN_4035
912			\|a GBV_ILN_4037
912			\|a GBV_ILN_4112
912			\|a GBV_ILN_4125
912			\|a GBV_ILN_4126
912			\|a GBV_ILN_4242
912			\|a GBV_ILN_4251
912			\|a GBV_ILN_4305
912			\|a GBV_ILN_4313
912			\|a GBV_ILN_4323
912			\|a GBV_ILN_4324
912			\|a GBV_ILN_4326
912			\|a GBV_ILN_4333
912			\|a GBV_ILN_4334
912			\|a GBV_ILN_4335
912			\|a GBV_ILN_4338
912			\|a GBV_ILN_4393
936	b	k	\|a 35.70 \|j Biochemie: Allgemeines
936	b	k	\|a 44.33 \|j Physiologische Chemie
936	b	k	\|a 44.42 \|j Pharmazeutische Chemie
951			\|a AR
952			\|d 30

Indexfelder

author_variant	n c nc l h lh k w kw z f zf z c zc m j mj z q zq p q pq x l xl
matchkey_str	article:14643405:2019----::oesloaiea
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publishDate	2019
allfields	10.1016/j.bmcl.2019.126859 doi (DE-627)ELV003488306 (ELSEVIER)S0960-894X(19)30833-9 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Cai, Nan verfasserin aut Novel sulfonamides against 2019 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Thirty-four novel compounds were synthesized using chesulfamide (N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by 1H NMR, 13C NMR, MS and elemental analysis. Additionally, the structure of (1S,2R)-2-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide (IV-9) was confirmed by X-ray single crystal diffraction. The mycelium inhibition tests, spore germination inhibition tests, tomato pot tests and field trials were performed against strains of B. cinerea. Bioassay results showed that most of target compounds had good fungicidal activity against B. cinerea, in particular, IV-9 exhibited similar or superior effects to procymidone, boscalid and pyrisoxazole in all in vitro and in vivo tests. Moreover, there was no positive cross-resistance found between the compound IV-9 and eight commercial fungicides (azoxystrobin, boscalid, chlorothalonil, diethofencarb, fludioxonil, procymidone, pyrimethanil and pyrisoxazole) in the cross-resistance validation test performed by an innovative method. Cycloalkylsulfonamides Reductive amination Fungicidal activity SAR Cross resistance He, Lu verfasserin aut Wang, Kai verfasserin aut Feng, Zhihui verfasserin aut Cui, Zining verfasserin aut Ji, Mingshan verfasserin aut Qi, Zhiqiu verfasserin aut Qin, Peiwen verfasserin aut Li, Xinghai verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 30 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:30 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 30
spelling	10.1016/j.bmcl.2019.126859 doi (DE-627)ELV003488306 (ELSEVIER)S0960-894X(19)30833-9 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Cai, Nan verfasserin aut Novel sulfonamides against 2019 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Thirty-four novel compounds were synthesized using chesulfamide (N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by 1H NMR, 13C NMR, MS and elemental analysis. Additionally, the structure of (1S,2R)-2-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide (IV-9) was confirmed by X-ray single crystal diffraction. The mycelium inhibition tests, spore germination inhibition tests, tomato pot tests and field trials were performed against strains of B. cinerea. Bioassay results showed that most of target compounds had good fungicidal activity against B. cinerea, in particular, IV-9 exhibited similar or superior effects to procymidone, boscalid and pyrisoxazole in all in vitro and in vivo tests. Moreover, there was no positive cross-resistance found between the compound IV-9 and eight commercial fungicides (azoxystrobin, boscalid, chlorothalonil, diethofencarb, fludioxonil, procymidone, pyrimethanil and pyrisoxazole) in the cross-resistance validation test performed by an innovative method. Cycloalkylsulfonamides Reductive amination Fungicidal activity SAR Cross resistance He, Lu verfasserin aut Wang, Kai verfasserin aut Feng, Zhihui verfasserin aut Cui, Zining verfasserin aut Ji, Mingshan verfasserin aut Qi, Zhiqiu verfasserin aut Qin, Peiwen verfasserin aut Li, Xinghai verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 30 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:30 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 30
allfields_unstemmed	10.1016/j.bmcl.2019.126859 doi (DE-627)ELV003488306 (ELSEVIER)S0960-894X(19)30833-9 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Cai, Nan verfasserin aut Novel sulfonamides against 2019 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Thirty-four novel compounds were synthesized using chesulfamide (N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by 1H NMR, 13C NMR, MS and elemental analysis. Additionally, the structure of (1S,2R)-2-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide (IV-9) was confirmed by X-ray single crystal diffraction. The mycelium inhibition tests, spore germination inhibition tests, tomato pot tests and field trials were performed against strains of B. cinerea. Bioassay results showed that most of target compounds had good fungicidal activity against B. cinerea, in particular, IV-9 exhibited similar or superior effects to procymidone, boscalid and pyrisoxazole in all in vitro and in vivo tests. Moreover, there was no positive cross-resistance found between the compound IV-9 and eight commercial fungicides (azoxystrobin, boscalid, chlorothalonil, diethofencarb, fludioxonil, procymidone, pyrimethanil and pyrisoxazole) in the cross-resistance validation test performed by an innovative method. Cycloalkylsulfonamides Reductive amination Fungicidal activity SAR Cross resistance He, Lu verfasserin aut Wang, Kai verfasserin aut Feng, Zhihui verfasserin aut Cui, Zining verfasserin aut Ji, Mingshan verfasserin aut Qi, Zhiqiu verfasserin aut Qin, Peiwen verfasserin aut Li, Xinghai verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 30 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:30 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 30
allfieldsGer	10.1016/j.bmcl.2019.126859 doi (DE-627)ELV003488306 (ELSEVIER)S0960-894X(19)30833-9 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Cai, Nan verfasserin aut Novel sulfonamides against 2019 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Thirty-four novel compounds were synthesized using chesulfamide (N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by 1H NMR, 13C NMR, MS and elemental analysis. Additionally, the structure of (1S,2R)-2-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide (IV-9) was confirmed by X-ray single crystal diffraction. The mycelium inhibition tests, spore germination inhibition tests, tomato pot tests and field trials were performed against strains of B. cinerea. Bioassay results showed that most of target compounds had good fungicidal activity against B. cinerea, in particular, IV-9 exhibited similar or superior effects to procymidone, boscalid and pyrisoxazole in all in vitro and in vivo tests. Moreover, there was no positive cross-resistance found between the compound IV-9 and eight commercial fungicides (azoxystrobin, boscalid, chlorothalonil, diethofencarb, fludioxonil, procymidone, pyrimethanil and pyrisoxazole) in the cross-resistance validation test performed by an innovative method. Cycloalkylsulfonamides Reductive amination Fungicidal activity SAR Cross resistance He, Lu verfasserin aut Wang, Kai verfasserin aut Feng, Zhihui verfasserin aut Cui, Zining verfasserin aut Ji, Mingshan verfasserin aut Qi, Zhiqiu verfasserin aut Qin, Peiwen verfasserin aut Li, Xinghai verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 30 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:30 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 30
allfieldsSound	10.1016/j.bmcl.2019.126859 doi (DE-627)ELV003488306 (ELSEVIER)S0960-894X(19)30833-9 DE-627 ger DE-627 rda eng 540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Cai, Nan verfasserin aut Novel sulfonamides against 2019 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Thirty-four novel compounds were synthesized using chesulfamide (N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by 1H NMR, 13C NMR, MS and elemental analysis. Additionally, the structure of (1S,2R)-2-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide (IV-9) was confirmed by X-ray single crystal diffraction. The mycelium inhibition tests, spore germination inhibition tests, tomato pot tests and field trials were performed against strains of B. cinerea. Bioassay results showed that most of target compounds had good fungicidal activity against B. cinerea, in particular, IV-9 exhibited similar or superior effects to procymidone, boscalid and pyrisoxazole in all in vitro and in vivo tests. Moreover, there was no positive cross-resistance found between the compound IV-9 and eight commercial fungicides (azoxystrobin, boscalid, chlorothalonil, diethofencarb, fludioxonil, procymidone, pyrimethanil and pyrisoxazole) in the cross-resistance validation test performed by an innovative method. Cycloalkylsulfonamides Reductive amination Fungicidal activity SAR Cross resistance He, Lu verfasserin aut Wang, Kai verfasserin aut Feng, Zhihui verfasserin aut Cui, Zining verfasserin aut Ji, Mingshan verfasserin aut Qi, Zhiqiu verfasserin aut Qin, Peiwen verfasserin aut Li, Xinghai verfasserin aut Enthalten in Bioorganic & medicinal chemistry letters Amsterdam [u.a.] : Elsevier Science, 1991 30 Online-Ressource (DE-627)306717522 (DE-600)1501505-1 (DE-576)110916573 1464-3405 nnns volume:30 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-PHARM SSG-OLC-PHA SSG-OPC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.70 Biochemie: Allgemeines 44.33 Physiologische Chemie 44.42 Pharmazeutische Chemie AR 30
language	English
source	Enthalten in Bioorganic & medicinal chemistry letters 30 volume:30
sourceStr	Enthalten in Bioorganic & medicinal chemistry letters 30 volume:30
format_phy_str_mv	Article
bklname	Biochemie: Allgemeines Physiologische Chemie Pharmazeutische Chemie
institution	findex.gbv.de
topic_facet	Cycloalkylsulfonamides Reductive amination Fungicidal activity SAR Cross resistance
dewey-raw	540
isfreeaccess_bool	false
container_title	Bioorganic & medicinal chemistry letters
authorswithroles_txt_mv	Cai, Nan @@aut@@ He, Lu @@aut@@ Wang, Kai @@aut@@ Feng, Zhihui @@aut@@ Cui, Zining @@aut@@ Ji, Mingshan @@aut@@ Qi, Zhiqiu @@aut@@ Qin, Peiwen @@aut@@ Li, Xinghai @@aut@@
publishDateDaySort_date	2019-01-01T00:00:00Z
hierarchy_top_id	306717522
dewey-sort	3540
id	ELV003488306
language_de	englisch
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author	Cai, Nan
spellingShingle	Cai, Nan ddc 540 ssgn 15,3 fid PHARM bkl 35.70 bkl 44.33 bkl 44.42 misc Cycloalkylsulfonamides misc Reductive amination misc Fungicidal activity misc SAR misc Cross resistance Novel sulfonamides against
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topic_title	540 610 DE-600 15,3 ssgn PHARM DE-84 fid 35.70 bkl 44.33 bkl 44.42 bkl Novel sulfonamides against Cycloalkylsulfonamides Reductive amination Fungicidal activity SAR Cross resistance
topic	ddc 540 ssgn 15,3 fid PHARM bkl 35.70 bkl 44.33 bkl 44.42 misc Cycloalkylsulfonamides misc Reductive amination misc Fungicidal activity misc SAR misc Cross resistance
topic_unstemmed	ddc 540 ssgn 15,3 fid PHARM bkl 35.70 bkl 44.33 bkl 44.42 misc Cycloalkylsulfonamides misc Reductive amination misc Fungicidal activity misc SAR misc Cross resistance
topic_browse	ddc 540 ssgn 15,3 fid PHARM bkl 35.70 bkl 44.33 bkl 44.42 misc Cycloalkylsulfonamides misc Reductive amination misc Fungicidal activity misc SAR misc Cross resistance
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title	Novel sulfonamides against
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title_full	Novel sulfonamides against
author_sort	Cai, Nan
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author_browse	Cai, Nan He, Lu Wang, Kai Feng, Zhihui Cui, Zining Ji, Mingshan Qi, Zhiqiu Qin, Peiwen Li, Xinghai
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author-letter	Cai, Nan
doi_str_mv	10.1016/j.bmcl.2019.126859
dewey-full	540 610
author2-role	verfasserin
title_sort	novel sulfonamides against
title_auth	Novel sulfonamides against
abstract	Thirty-four novel compounds were synthesized using chesulfamide (N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by 1H NMR, 13C NMR, MS and elemental analysis. Additionally, the structure of (1S,2R)-2-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide (IV-9) was confirmed by X-ray single crystal diffraction. The mycelium inhibition tests, spore germination inhibition tests, tomato pot tests and field trials were performed against strains of B. cinerea. Bioassay results showed that most of target compounds had good fungicidal activity against B. cinerea, in particular, IV-9 exhibited similar or superior effects to procymidone, boscalid and pyrisoxazole in all in vitro and in vivo tests. Moreover, there was no positive cross-resistance found between the compound IV-9 and eight commercial fungicides (azoxystrobin, boscalid, chlorothalonil, diethofencarb, fludioxonil, procymidone, pyrimethanil and pyrisoxazole) in the cross-resistance validation test performed by an innovative method.
abstractGer	Thirty-four novel compounds were synthesized using chesulfamide (N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by 1H NMR, 13C NMR, MS and elemental analysis. Additionally, the structure of (1S,2R)-2-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide (IV-9) was confirmed by X-ray single crystal diffraction. The mycelium inhibition tests, spore germination inhibition tests, tomato pot tests and field trials were performed against strains of B. cinerea. Bioassay results showed that most of target compounds had good fungicidal activity against B. cinerea, in particular, IV-9 exhibited similar or superior effects to procymidone, boscalid and pyrisoxazole in all in vitro and in vivo tests. Moreover, there was no positive cross-resistance found between the compound IV-9 and eight commercial fungicides (azoxystrobin, boscalid, chlorothalonil, diethofencarb, fludioxonil, procymidone, pyrimethanil and pyrisoxazole) in the cross-resistance validation test performed by an innovative method.
abstract_unstemmed	Thirty-four novel compounds were synthesized using chesulfamide (N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by 1H NMR, 13C NMR, MS and elemental analysis. Additionally, the structure of (1S,2R)-2-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide (IV-9) was confirmed by X-ray single crystal diffraction. The mycelium inhibition tests, spore germination inhibition tests, tomato pot tests and field trials were performed against strains of B. cinerea. Bioassay results showed that most of target compounds had good fungicidal activity against B. cinerea, in particular, IV-9 exhibited similar or superior effects to procymidone, boscalid and pyrisoxazole in all in vitro and in vivo tests. Moreover, there was no positive cross-resistance found between the compound IV-9 and eight commercial fungicides (azoxystrobin, boscalid, chlorothalonil, diethofencarb, fludioxonil, procymidone, pyrimethanil and pyrisoxazole) in the cross-resistance validation test performed by an innovative method.
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title_short	Novel sulfonamides against
remote_bool	true
author2	He, Lu Wang, Kai Feng, Zhihui Cui, Zining Ji, Mingshan Qi, Zhiqiu Qin, Peiwen Li, Xinghai
author2Str	He, Lu Wang, Kai Feng, Zhihui Cui, Zining Ji, Mingshan Qi, Zhiqiu Qin, Peiwen Li, Xinghai
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doi_str	10.1016/j.bmcl.2019.126859
up_date	2024-07-06T19:47:32.329Z
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score	7.399024

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