Synthesis, Crystal Structure, and Herbicidal Activities of 2‐Cyanoacrylates Containing 1,3,4‐Thiadiazole Moieties

Wang, Tingting; Miao, Wenke; Wu, Shanshan; Bing, Guifang; Zhang, Xin; Qin, Zhenfang; Yu, Haibo; Qin, Xiao; Fang, Jianxin

doi:10.1002/cjoc.201190196

Cited by 29 publications

(15 citation statements)

References 16 publications

(12 reference statements)

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“…1,3,4-噻二唑类化合物由于具有杀菌 [11,12] 、杀虫 [13] 、除草 [14,15] 和调节植物生长 [16～18] 等广泛的生物活性而倍受青睐, 而且硫醚类化合物也是一类具有抗菌活性的化合物 [11,19] . …”

Section: 吡唑并[34-d]嘧啶类衍生物是一类具有良好生物活性的含氮稠环化合物因吡唑并[34-d]嘧啶的结构与嘌呤环类unclassified

Synthesis and Biological Activity of Pyrazolo[3,4-d]pyrimidine Derivatives Containing 1,3,4-Thiadiazole

Xia¹,

Shao²,

Duan³

et al. 2012

Chin. J. Org. Chem.

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School of Chemical and Environmental Engineering, Hubei University for Nationalities, Enshi 445000)Abstract Twelve novel pyrazolo [3,4-d]pyrimidine derivatives containing a 1,3,4-thiadiazole group were synthesized through cyclization of 5-amino-4-cyano-1-phenylpyrazole with formic acid, followed by chloridization and S N Ar reaction. The structures of all these title compounds were confirmed by IR, 1 H NMR, MS techniques and elemental analysis. The preliminary bioassay showed that most of the title compounds exhibit relatively good fungicidal activities against Rhizoctonia cerealis at the concentration of 50 mg/L, especially the inhibitory rates of compounds 5b, 5d and 5j reach above 90%.

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Section: 吡唑并[34-d]嘧啶类衍生物是一类具有良好生物活性的含氮稠环化合物因吡唑并[34-d]嘧啶的结构与嘌呤环类unclassified

Synthesis and Biological Activity of Pyrazolo[3,4-d]pyrimidine Derivatives Containing 1,3,4-Thiadiazole

Xia¹,

Shao²,

Duan³

et al. 2012

Chin. J. Org. Chem.

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“…Triazole compounds have been extensively studied in the field of medicine and pesticides, and exhibit a variety of biological activities. In addition to a strong internal fungicidal activity, triazole compounds also have a regulatory role in the growth of plant [ 12 ], herbicidal [ 13 ], insecticidal [ 14 ] and antifungal [ 15 , 16 ]. Because of these multiple effect of the triazole structure, the research of these compounds have been in the ascendant so far.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis and Bioactivity of Novel Triazole Derivatives

Zhao

Chen

et al. 2018

Molecules

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Triazole pesticides are organic nitrogen-containing heterocyclic compounds, which contain 1,2,3-triazole ring. In order to develop potential glucosamine-6-phosphate synthase (GlmS) inhibitor fungicides, forty compounds of triazole derivatives were synthesized in an efficient way, thirty nine of them were new compounds. The structures of all the compounds were confirmed by high resolution mass spectrometer (HRMS), 1H-NMR and 13C-NMR. The fungicidal activities results based on means of mycelium growth rate method indicated that some of the compounds exhibited good fungicidal activities against P. CapasiciLeonian, Sclerotinia sclerotiorum (Lib.) de Bary, Pyricularia oryzae Cav. and Fusarium oxysporum Schl. F.sp. vasinfectum (Atk.) Snyd. & Hans. at the concentration of 50 µg/mL, especially the inhibitory rates of compounds 1-d and 1-f were over 80%. At the same time, the preliminary studies based on the Elson-Morgan method indicated that the compounds exhibited some inhibitory activity toward glucosamine-6-phosphate synthase (GlmS). These compounds will be further studied as potential antifungal lead compounds. The structure-activity relationships (SAR) were discussed in terms of the effects of the substituents on both the benzene and the sugar ring.

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“…In our previous work, the cyanoacrylate structure modified by replacing phenyl with 4,5-dihydro-1,3,4-thiadiazol-5-one showed relatively lower herbicidal activities than the parental compound. 17 This is possibly due to the relatively high polarity and the decrease in the overall molecular lipophilicity. 10 and its activity were reported in Ref.…”

Section: Crystal Structure Analysismentioning

confidence: 99%

Synthesis, crystal structure, and herbicidal activity of novel 1,2,3-thiadiazole substituted 2-cyanoacrylates

Jian-Xin¹,

Wang²,

Bing³

et al. 2010

Arkivoc

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A series of novel 2-cyanoacrylates containing the 1,2,3-thiadiazole ring moiety were synthesized and characterized by 1 H NMR, 13C NMR, elemental analysis and, in one case, by X-ray crystallography. Most of these cyanoacrylates exhibited good herbicidal activities. In particular, (Z)-methoxyethyl-and (Z)-ethoxyethyl-2-cyano-3-isopropyl-3-(4-methyl-1,2,3-thiadiazol-5-yl)methylaminoacrylate 9h and 9g showed 100% herbicidal activities against rape and amaranth pigweed at a dose of 1.5 kg/ha. 2-Cyanoacrylates containing the thiadiazole ring are a new variation of this class of compound which still retain herbicidal activities.

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Synthesis, Crystal Structure, and Herbicidal Activities of 2‐Cyanoacrylates Containing 1,3,4‐Thiadiazole Moieties

Cited by 29 publications

References 16 publications

Synthesis and Biological Activity of Pyrazolo[3,4-d]pyrimidine Derivatives Containing 1,3,4-Thiadiazole

Synthesis and Biological Activity of Pyrazolo[3,4-d]pyrimidine Derivatives Containing 1,3,4-Thiadiazole

Efficient Synthesis and Bioactivity of Novel Triazole Derivatives

Synthesis, crystal structure, and herbicidal activity of novel 1,2,3-thiadiazole substituted 2-cyanoacrylates

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