Efficient Synthesis and Bioactivity of Novel Triazole Derivatives

Abstract

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.

Research progress of triazole derivatives in the discovery of agricultural chemicals

“…de Bary, Pyricularia oryzae Cav. and Fusarium oxysporum have an inhibition rate of over 80%, In addition, they have certain inhibitory activity against glucosamine 6-phosphate synthase (GlmS) [66], and they can be used as antifungal lead compounds to further optimize the molecular structure. At a concentration of 50 mg/L, compounds 12-15 showed good antifungal activity on sunflower sclerotinia rot, with inhibition rates exceeding 80% [67].…”

1,2,4-Oxadiazole as a potential scaffold in agrochemistry: a review

“…3 Using diverse innovative skeletons and significant moieties is a strategic approach for acquiring bioactive molecules, thereby enhancing efficiency or obtaining novel modes of action towards their respective targets. The investigation of various heterocyclic compounds containing pyridine, 4,5 oxazole, 6 triazole, 7 pyrazole, 8 etc . has become a trending topic in both the chemistry and pharmaceutical fields.…”

High Efficiency Synthesis of the Tetrasccharide Repeating Unit in Azospirillum brasilense Strains Sp246 Based on Silica Gel Supported Perchloric Acid (HClO4-SiO2)

“…calcd for C 49 H 42 Cl 3 NO 14 : C 60.35,H 4.34,N 1.44;found C 60.23,H 4.22,N 1.31. 3.2.7 2,3,4,6 13), 产率 91%.…”

“…78.5～ 79.2 ℃; 1 H NMR (CDCl 3 , 400 MHz) δ: 0.44～0.59 (m, 6H, CH 2 ×3), 0.78 (t, J＝7.9 Hz, 9H, CH 3 ×3), 1.33 (d,J＝6.1 Hz,3H,3.75 (s,3H,OCH 3 ),3.90～3.94 (m,1H),4.07 (t,J＝9.3 Hz,1H),4.17～4.21 (m,1H),4.36 (dd,J＝9.2,3.4 Hz,1H),4.46 (dd,J＝12.1,4.7 Hz,1H),4.82 (dd,J＝12.1,3.3 Hz,1H),5.30 (s,1H),5.35 (d,J＝ 7.8 Hz,1H,5.40 (d,J＝1.8 Hz,1H,5.56 (dd,J＝9.8,7.8 Hz,1H),5.73 (t,J＝9.6 Hz,1H), 5.91 (t, J＝9.6 Hz, 1H), 6.59～7.07 (m, 4H), 7.14～8.09 (m, 25H, ArH); 13 C NMR (101 MHz, CDCl 3 ) δ: 5.01, 6.85, 18.1, 55.8, 62.9, 67.9, 70.1, 70.6, 72.1, 72.8, 73.3, 73.7, 77.4, 96.8, 100.5, 114.7, 118.2, 128.3, 128.4, 128.5, 128.56, 128.9, 128.9, 129.2, 129.6, 129.7, 129.8, 129.8, 129.9, 129.9, 130.0, 130.2, 133.2, 133.2, 133.3, 133.3, 133.6, 150.5, 155.3, 165.3, 165.6, 166.0, 166.2, 166.3 Si: C 67.53,H 5.86;found C 67.34,H 5.66. 3.3.11 2,3,4,…”