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Article

Synthesis and Insecticidal/Fungicidal Activities of Triazone Derivatives Containing Acylhydrazone Moieties

by
Peipei Cui
1 and
Yan Yang
2,*
1
College of Architecture and Arts, Taiyuan University of Technology, Jinzhong 030060, China
2
College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024, China
*
Author to whom correspondence should be addressed.
Molecules 2025, 30(2), 340; https://doi.org/10.3390/molecules30020340
Submission received: 28 November 2024 / Revised: 28 December 2024 / Accepted: 10 January 2025 / Published: 16 January 2025
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Versions Notes

Abstract

:
A series of novel triazone derivatives containing aldehyde hydrazone or ketone hydrazone moieties were designed, synthesized and their biological activities were investigated against Aphis craccivora, Culex pipiens pallens, Helicoverpa armigera, Ostrinia nubilalis, Mythimna separata and 14 Kinds of fungi. Most of the aldehyde hydrazone exhibited excellent insecticidal activities against A. craccivora. In particular, the aphicidal activities of compounds 3t (35%) and 3w (30%) were equivalent to pymetrozine (30%) at 5 mg/kg. The aphicidal activities of derivatives 3p, 3u, 3y, 5g, 5i, 5l, 5q and 5u against C. pipiens pallens were higher than that of pymetrozine. Compound 3u (100%) exhibited good larvicidal activities against C. pipiens pallens at 0.25 mg/kg. Most derivatives exhibited broad-spectrum fungicidal activities against 14 kinds of plant fungi at 50 mg/kg. Thirty-nine compounds exhibited a more than 50% inhibition rate against Physalospora piricola. Compounds 3h, 3t and 3w were expected to be the leading structure for the development of new triazone insecticides agents.

1. Introduction

Owing to their direct feeding, transmission of destructive plant viruses and high reproductive rate [1], aphids (Hemiptera: Aphididae) have become the most destructive pests, causing plant diseases that significantly reduce crop yield and quality [2].
As a pyridine azomethine insecticide, pymetrozine was first developed by Syngenta in 1988 [3] and has become a hot research topic globally due to its high efficiency, satisfied selectivity and environmental friendliness [4,5,6,7,8,9,10,11,12,13,14]. However, only two analogs of this type of insecticides (R-768 and pyrifluquinazon (Figure 1)) have been found so far, and their activities were significantly lower than that of pymetrozine [9,15].
In 2015, Nesterov et al. found that the action targets of pymetrozine insecticide were transient receptor potential (TRP) channels [16], which were non-selective cation channels composed of 28 cation-permeable channels. TRPC (transient receptor potential-canonical) was a subfamily of TRP channels [17], which was inwardly rectifying and was considered as a therapeutic target for mental disorders such as depression, borderline personality disorder and post-traumatic stress disorder [18,19]. The pyridazinone compound GFB-8438 (Figure 2) was a highly selective, potent TRPC5 antagonist, which specifically interacted with the TRPC5-Rac1 pathway in podocytes to attenuate FSGS and diabetic nephropathy [20]. Pymetrozine acted on the same target site as GFB-8438 [16].
Hydrazones moieties are important structural units that exist in many bioactive molecules, with a wide range of biological activities. Metaflumizone is a semicarbazone insecticide developed by BASF (Ludwigshafen, Germany) and Nihon Nohyaku Co., Ltd. (Tokyo, Japan) which provides good-to-excellent control of lepidopterous pests and certain pests in the orders Coleoptera, Hemiptera, Hymenoptera, Diptera, Isoptera and Siphonaptera [21]. Diflufenzopyr containing hydrazone moiety is also used as a commercialized insecticide [22]. Benquinox is a desirable fungicide which protects seeds and seedlings against fungal infections [23]. Furacilin has been used for the treatment of bacterial and protozoal infections for many years [24]. Compounds 3 [25] and 4 [26] exhibit higher antiviral activities than ribavirin. Azimilide and Ftivazide exhibit antiarrhythmic [27] and antituberculosis [28] activities, respectively. GFB-887 [29] compounds 1 and 2 [30] (Figure 2) containing hydrazone moieties were used as TRP antagonists. Based on the bioactivies and targeting TRP channels of GFB-8438, GFB-887, 1 and pymetrozine, the acylhydrazone structure was introduced into pymetrozine to design and synthesize a series of triazone aldehyde and ketone hydrazone derivatives (Figure 3). Their insecticidal activities against bean aphid and lepidopteran pests were repeated three times. In addition, their antiphytopathogenic fungus activities were also investigated.

2. Results and Discussions

2.1. General Synthesis

The synthetic routes of the target compounds 3a–3w and 5a–5u are given in Scheme 1. Intermediate 1 was synthesized by the method reported in the literature [31]. 4-Amino-6-methyl-4,5-dihydro-2H-[1,2,4]triazin-3-one reacted with benzoyl chloride to give (6-Methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazin-4-yl)-carbamic acid phenyl ester, which reacted with hydrazine hydrate to give intermediate 1. Using p-toluenesulfonic acid as a catalyst, compound 1 reacted with aldehydes 2a–2w to form compounds 3a–3w in 57–88% yields. Compounds 5a–5u were synthesized by the condensation of compound 1 and ketones 4a–4u in 56–97% yields. Alkyl, cycloalkyl, and substituted phenyl were introduced into acylhydrazone derivatives to investigate the effect of different substituents on activity. Experimental operating steps and data of target compounds 3a–3w and 5a–5u are available in the Supplementary Materials.

2.2. Biological Evaluation

2.2.1. Foliar Contact Activity Against Bean Aphid (A. craccivora)

As seen from Table 1, most aldehyde hydrazone compounds exhibited weak insecticidal activities; only compounds 3h (2, 3-dimethoxy, 15%), 3t (4-dimethylamino, 35%) and 3w (2-thiophene, 30%) exhibited the same level of aphicidal activities as pymetrozine (30%) at 5 mg/kg. Compounds 3t and 3w exhibited high insecticidal activities because nitrogen and sulfur atoms may form hydrogen bonding with the TRP channels [16]. The rotation of chemical bonds of acylhydrazone compounds can lead to different conformations [32], also affecting their biological activities.
When R was an alkyl substituent, the size of the substituent had significant effects on the aphicidal activities (3a–3c). For example, the insecticidal activity of compound 3b (85%, t-butyl) was higher than that of compound 3a (30%, n-propyl) at 100 mg/kg. When R was aromatic groups, the activities increased obviously. In order to investigate the effects of the substituent positions, electrical properties and the number of substituents on the phenyl group on the insecticidal activities, different substituents were introduced to the benzene ring (3e–3t). The results indicated that most of these derivatives exhibited more than 30% activity at 10 mg/kg, which was lower than that of pymetrozine (90%). The positions and numbers of electron-donating substituents had important effects on the activities; for example, compounds 3f (3-methoxy, 20%) and 3g (4-methoxy, 45%) exhibited lower activities than 3h (2, 3-dimethoxy, 70%) at 10 mg/kg. The positions and numbers of electron-withdrawing substituents had little effect on the activities; for example, 3l (3-chlorine, 35%) and 3m (4-chlorine, 40%) exhibited activities which were equivalent to 3n (3, 4-dichlorine, 30%) at 10 mg/kg. Meanwhile, it was found that the electron-donating compound 3t (4-dimethylamino, 35%) and electron-withdrawing compound 3w (2-thiophene, 30%) exhibited activities which were equivalent to pymetrozine (30%) at 5 mg/kg.
When R was changed from phenyl to naphthyl, the insecticidal activity of the compound remained unchanged; such as in compound 3d (phenyl, 30%), which exhibited activity equivalent to 3u (naphthyl, 30%) at 10 mg/kg. In addition, while the benzene ring was replaced with other aromatic heterocycles (3v–3w), the insecticidal activities were enhanced. For example, compound 3w (2-thiophene, 30%) exhibited the same level of activity as pymetrozine (30%) at 5 mg/kg.
The aphicidal activities of ketone hydrazone derivatives (5a–5u) are listed in Table 2. From Table 1 and Table 2, it can be seen that most aldehyde hydrazone derivatives exhibited better activities than the ketone hydrazone compounds.

2.2.2. Larvicidal Activities Against Mosquito (C. pipiens pallens), Cotton Bollworm (H. armigera), Oriental Armyworm (M. separata) and Corn Borer (O. nubilalis)

The larvicidal activities of synthesized compounds 3a–3w, 5a–5u and pymetrozine against mosquitoes are shown in Table 3 and Table 4. Most compounds exhibited good larvicidal activities against C. pipiens pallens. In particular, the larvicidal activities of derivatives 3p, 3u, 3y, 5g, 5i, 5l, 5q and 5u were higher than that of pymetrozine, and compound 3u (containing a 6-methoxy on the naphthyl) showed the highest larvicidal activity (40% at 0.1 mg/kg). The positions and numbers of substituents on the phenyl of these derivatives were critical for the activities against mosquitoes. For example, 5h (3-methoxy) only showed 20% correcting mortality at 0.5 mg/kg, whereas 5i (4-methoxy) exhibited 40% correcting mortality at 0.25 mg/kg. Meanwhile, 5j (3,4-diemethoxy) and 5k (3,4,5-triemethoxy) exhibited 50% and 30% correcting mortality at 0.5 mg/kg, respectively.
Compounds 3a–3w and 5a–5u have high stability. According to previous research on compounds with similar structures, compounds 3a–3w and 5a–5u may exhibit lower toxicity to non-target organisms. Compounds with higher nitrogen atom ratios may have relatively higher acute toxicity. Therefore, we predict that compounds 3t, 3p, 3q, 3v and 5u may exhibit relatively higher toxicity. Therefore, compounds 3t and 3w can be further developed as potential insecticides.

2.2.3. Fungicidal Activities

Compounds 3a–3w and 5a–5u were also evaluated for their fungicidal activities, with commercial fungicides carbendazim and chlorothalonil as controls (Table 5). The fungicidal activities test was repeated three times. Most derivatives showed broad-spectrum fungicidal activities against 14 kinds of phytopathogens. Overall, these derivatives showed excellent fungicidal activities against P. piricola. In particular, compound 5l exhibited more than 50% inhibition against six kinds of fungi; compounds 5c, 5f and 5g exhibited more than 50% inhibition against five kinds of fungi and compound 5t exhibited a 90% inhibition rate against P. piricola at 50 mg/kg. The fungicidal activities of these compounds also exhibited a certain selectivity. At 50 mg/kg, 20 compounds exhibited a more than 50% inhibition rate against Fusarium graminearum, which was higher than chlorothalonil. A total of 7 compounds (against Fusarium oxysporum f. sp. cucumeris), 19 compounds (against Cercospora arachidicola Hori), 39 kinds of compounds (against P. piricola) and 13 compounds (against Fusarium moniliforme) showed a more than 50% inhibition rate at the concentration of 50 mg/kg, which was higher than the fungicidal activities of carbendazim.

3. Materials and Methods

Pymetrozine (Chemieliva Pharmaceutical Co., Ltd., Chongqing, China), carbendazim (Bailing Agrochemical Co., Ltd., Jiangyin, China), chlorothalonil (Bailing Agrochemical Co., Ltd., Beijing, China) and other reagents were used as received. All solvents were dried and purified using standard techniques. 1H NMR and 13C NMR spectra were obtained at 400 MHz using a Bruker (Billerica, MA, USA) AV400 spectrometer in CDCl3 or DMSO-d6 solution with tetramethylsilane as the internal standard. Chemical shift values (δ) are given in parts per million. HRMS data were obtained on an FTICR-MS instrument (Ionspec 7.0 T, Agilent, Santa Clara, CA, USA). The melting points were determined using an X-4 binocular microscope melting-point apparatus and are uncorrected.
The biological assays for the foliar contact activity against bean aphid (A. craccivora), the larvicidal activities against mosquito larvae (C. pipiens pallens) and the stomach toxicity against cotton bollworm (H. armigera), oriental armyworm (M. separata) and corn borer (O. nubilalis) of compounds 3a–3w, 5a–5u and pymetrozine were conducted using the reported procedure [33,34,35]. The tests of fungicidal activities were carried out using the reported methods [36]. The testing process can also be found in the Supporting Information. The biological assays were repeated three times. The correcting mortality values were rounded to their nearest integers.

4. Conclusions

In summary, a series of novel triazone compounds containing aldehyde hydrazone or ketone hydrazone moieties were synthesized and evaluated for their insecticidal and fungicidal activities. Compounds 3t and 3w exhibited aphicidal activities comparable to pymetrozine. Compound 3u showed the highest larvicidal activity against C. pipiens pallens (40% at 0.1 mg/kg). In addition, most derivatives exhibited broad-spectrum fungicidal activities against 14 kinds of plant fungi at 50 mg/kg. A total of 20 compounds exhibited a more than 50% inhibition rate against F. graminearum at 50 mg/kg and 39 compounds exhibited a more than 50% inhibition rate against P. piricola. Triazone compounds containing hydrazone moieties could be further explored as candidate insecticides against aphids.

Supplementary Materials

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/molecules30020340/s1, File S1: the general preparation process of 3a–3w and 5a–5w, 1H and 13C NMR data and spectra of 3a–3w and 5a–5w, detailed bioassay procedures for the anti-TMV activities and fungicidal activities.

Author Contributions

Synthesizing compounds and writing the manuscript, P.C.; synthesizing compounds and biological activity testing, Y.Y. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by Fundamental Research Program of Shanxi Province, funding number 20210302123180 and 202303021221016, and the National Natural Science Foundation of China, funding number 22001190 and 21702144.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Data will be made available on request.

Conflicts of Interest

The authors declare no conflicts of interest.

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Molecules 30 00340 g001
Figure 1. Pymetrozine, R-768 and pyrifluquinazon.
Figure 1. Pymetrozine, R-768 and pyrifluquinazon.
Molecules 30 00340 g001
Molecules 30 00340 g002
Figure 2. Selected TRP antagonists, pesticides and drugs containing hydrazones moieties. The hydrazone structure is marked with different colors. For compounds with proprietary names, proprietary names are used. For compounds without proprietary names, numbers are used.
Figure 2. Selected TRP antagonists, pesticides and drugs containing hydrazones moieties. The hydrazone structure is marked with different colors. For compounds with proprietary names, proprietary names are used. For compounds without proprietary names, numbers are used.
Molecules 30 00340 g002
Molecules 30 00340 g003
Figure 3. Design of target compounds. The hydrazone structure is marked with different colors. For compounds with proprietary names, proprietary names are used. For compounds without proprietary names, numbers are used.
Figure 3. Design of target compounds. The hydrazone structure is marked with different colors. For compounds with proprietary names, proprietary names are used. For compounds without proprietary names, numbers are used.
Molecules 30 00340 g003
Molecules 30 00340 sch001
Scheme 1. Synthetic Route for 3a–3w and 5a–5u.
Scheme 1. Synthetic Route for 3a–3w and 5a–5u.
Molecules 30 00340 sch001
Table 1. Foliar contact activities against A. craccivora of compounds 3a–3w and pymetrozine.
Table 1. Foliar contact activities against A. craccivora of compounds 3a–3w and pymetrozine.
CompoundMolecules 30 00340 i001
R1		Correcting Mortality (%) at Concentration (mg/kg)
600100105
3aMolecules 30 00340 i00270 ± 230 ± 0-a-a
3bMolecules 30 00340 i003100 ± 085 ± 230 ± 0-a
3cMolecules 30 00340 i004100 ± 070 ± 1-a-a
3dMolecules 30 00340 i005100 ± 095 ± 230 ± 0-a
3eMolecules 30 00340 i006100 ± 090 ± 030 ± 0-a
3fMolecules 30 00340 i007100 ± 070 ± 020 ± 0-a
3gMolecules 30 00340 i008100 ± 095 ± 245 ± 2-a
3hMolecules 30 00340 i009100 ± 0100 ± 070 ± 015 ± 1
3iMolecules 30 00340 i01095 ± 190 ± 050 ± 0-a
3jMolecules 30 00340 i011100 ± 0100 ± 040 ± 0-a
3kMolecules 30 00340 i012100 ± 095 ±230 ± 0-a
3lMolecules 30 00340 i013100 ± 095 ± 235-a
3mMolecules 30 00340 i014100 ± 0100 ± 040 ± 0-a
3nMolecules 30 00340 i015100 ± 090 ± 030 ± 0-a
3oMolecules 30 00340 i016100 ± 095 ± 035 ± 0-a
3pMolecules 30 00340 i01785 ± 240 ± 0-a-a
3qMolecules 30 00340 i018100 ± 090 ± 035 ± 1-a
3rMolecules 30 00340 i019100 ± 080 ± 020 ± 0-a
3sMolecules 30 00340 i020100 ± 090 ± 025 ± 2-a
3tMolecules 30 00340 i021100 ± 0100 ± 095 ± 035 ± 2
3uMolecules 30 00340 i022100 ± 090 ± 030 ± 0-a
3vMolecules 30 00340 i023100 ± 095 ± 045 ± 0-a
3wMolecules 30 00340 i024100 ± 0100 ± 085 ± 230 ± 0
pymetrozineMolecules 30 00340 i025100 ± 0100 ± 090 ± 030 ± 0
a-not tested.
Table 2. Foliar contact activities against A. craccivora of compounds 5a–5u and pymetrozine.
Table 2. Foliar contact activities against A. craccivora of compounds 5a–5u and pymetrozine.
CompoundMolecules 30 00340 i026
R2		Correcting Mortality (%) at Concentration (mg/kg)
600100105
5aMolecules 30 00340 i02790 ± 030 ± 0-a-a
5bMolecules 30 00340 i028100 ± 035 ± 2-a-a
5cMolecules 30 00340 i029100 ± 040 ± 0-a-a
5dMolecules 30 00340 i03095 ± 270 ± 015 ± 1-a
5eMolecules 30 00340 i03180 ± 045 ± 2-a-a
5fMolecules 30 00340 i03280 ± 030 ± 0-a-a
5gMolecules 30 00340 i03395 ± 260 ± 010 ± 0-a
5hMolecules 30 00340 i034100 ± 050 ± 0-a-a
5iMolecules 30 00340 i035100 ± 065 ± 110 ± 0-a
5jMolecules 30 00340 i036100 ± 080 ± 035 ± 2-a
5kMolecules 30 00340 i037100 ± 095 ± 265 ± 2-a
5lMolecules 30 00340 i03895 ± 280 ± 010 ± 0-a
5mMolecules 30 00340 i039100 ± 070 ± 010 ± 0-a
5nMolecules 30 00340 i04090 ± 030 ± 0-a-a
5oMolecules 30 00340 i041100 ± 075 ± 215 ± 1-a
5pMolecules 30 00340 i04295 ± 185 ± 025 ± 1-a
5qMolecules 30 00340 i043100 ± 095 ± 045 ± 0-a
5rMolecules 30 00340 i044100 ± 080 ± 025 ± 0-a
5sMolecules 30 00340 i045100 ± 095 ± 035 ± 0-a
5tMolecules 30 00340 i046100 ± 085 ± 035 ± 1-a
5uMolecules 30 00340 i047100 ± 090 ± 035 ± 1-a
pymetrozineMolecules 30 00340 i048100 ± 0100 ± 090 ± 030 ± 0
a—not tested.
Table 3. Insecticidal activities of compounds 3a–3w, 5a–5u and pymetrozine against C. pipiens pallens.
Table 3. Insecticidal activities of compounds 3a–3w, 5a–5u and pymetrozine against C. pipiens pallens.
CompoundCorrecting Mortality (%) at Concentration (mg/kg)
105210.50.250.1
3a30 ± 0-a-a-a-a-a-a
3b100 ± 00-a-a-a-a-a
3c100 ± 0100 ± 0100 ± 040 ± 0-a-a-a
3d40 ± 0-a-a-a-a-a-a
3e100 ± 0100 ± 050 ± 0-a-a-a-a
3f100 ± 0100 ± 060 ± 0-a-a-a-a
3g100 ± 0100 ± 040 ± 0-a-a-a-a
3h100 ± 0100 ± 0100 ± 020 ± 0-a-a-a
3i100 ± 040 ± 0-a-a-a-a-a
3j100 ± 0100 ± 0100 ± 0100 ± 060 ± 0-a-a
3k100 ± 020 ± 0----a-a
3l100 ± 0100 ± 0100 ± 0100 ± 060 ± 0-a-a
3m100 ± 0100 ± 0100 ± 0100 ± 040 ± 0-a-a
3n100 ± 0100 ± 070 ± 0-a-a-a-a
3o80 ± 0-a-a-a-a-a-a
3p100 ± 0100 ± 0100 ± 0100 ± 0100 ± 040 ± 0-a
3q100 ± 0100 ± 020 ± 0-a-a-a-a
3r100 ± 0100 ± 0100 ± 0100 ± 060 ± 0-a-a
3s100 ± 0100 ± 010 ± 0-a-a-a-a
3t30 ± 0-a-a-a-a-a-a
3u100 ± 0100 ± 0100 ± 0100 ± 0100 ± 0100 ± 040 ± 0
3v100 ± 0100 ± 0100 ± 0100 ± 0100 ± 020 ± 0-a
3w100 ± 0100 ± 0100 ± 0100 ± 020 ± 0-a-a
5a100 ± 0100 ± 040 ± 0-a-a-a-a
5b100 ± 0100 ± 0100 ± 0100 ± 020 ± 0-a-a
5c50 ± 0-a-a-a-a-a-a
5d30 ± 0-a-a-a-a-a-a
5e30 ± 0-a-a-a-a-a-a
5f60 ± 0-a-a-a-a-a-a
5g100 ± 0100 ± 0100 ± 0100 ± 0100 ± 020 ± 0-a
5h100 ± 0100 ± 0100 ± 080 ± 020 ± 0-a-a
5i100 ± 0100 ± 0100 ± 0100 ± 0100 ± 040 ± 0-a
5j100 ± 0100 ± 0100 ± 0100 ± 050 ± 0-a-a
5k100 ± 0100 ± 0100 ± 0100 ± 030 ± 0-a-a
5l100 ± 0100 ± 0100 ± 0100 ± 0100 ± 040 ± 0-a
5m100 ± 0100 ± 0100 ± 0100 ± 020 ± 0-a-a
5n100 ± 0100 ± 0100 ± 0100 ± 060 ± 0-a-a
5o100 ± 0100 ± 0100 ± 0100 ± 0100 ± 040 ± 0-a
5p100 ± 0100 ± 0100 ± 060 ± 0-a-a-a
5q100 ± 0100 ± 0100 ± 080 ± 020 ± 0-a-a
5r80 ± 040 ± 0-a-a-a-a-a
5s90 ± 030± 0-a-a-a-a-a
5t70 ± 0-a-a-a-a-a-a
5u100 ± 0100 ± 0100 ± 0100 ± 020 ± 0-a-a
pymetrozine100 ± 040 ± 0-a-a-a-a-a
a—not tested.
Table 4. Insecticidal activities of compounds 3a–3w, 5a–5u and pymetrozine against H. armigera, O. nubilalis and M. separata at 600 mg/kg.
Table 4. Insecticidal activities of compounds 3a–3w, 5a–5u and pymetrozine against H. armigera, O. nubilalis and M. separata at 600 mg/kg.
CompoundCorrecting Mortality (%) at Concentration 600 mg/kg
mg/kg)
H. armigeraO. ubilalisM. eparata
3a15 ± 015 ± 010 ± 0
3b005 ± 0
3c25 ± 015 ± 020 ± 0
3d15 ± 010 ± 020 ± 0
3e5 ± 020 ± 020 ± 0
3f15 ± 05 ± 015 ± 0
3g000
3h20 ± 015 ± 025 ± 0
3i005 ± 0
3j25 ± 015 ± 025 ± 0
3k10 ± 05 ± 020 ± 0
3l55 ± 045 ± 070 ± 0
3m15 ± 010 ± 020 ± 0
3n55 ± 045 ± 065 ± 0
3o005 ± 0
3p100 ± 0/100 a ± 0/
20b ± 0		100 ± 0/100 a ± 0/30 b ± 0100 ± 0/100 a ± 0/20 b ± 0
3q25 ± 020 ± 035 ± 0
3r35 ± 025 ± 045 ± 0
3s10 ± 020 ± 020 ± 0
3t100 ± 0/100 a ± 0/30 b ± 0100 ± 0/100 a ± 0/20 b ± 0100 ± 0/100 a ± 0/60 b ± 0
3u15 ± 010 ± 015 ± 0
3v15 ± 010 ± 025 ± 0
3w35 ± 025 ± 040 ± 0
5a15 ± 010 ± 025 ± 0
5b55 ± 050 ± 080 ± 0
5c20 ± 010 ± 020 ± 0
5d000
5e15 ± 010 ± 020 ± 0
5f50 ± 045 ± 065 ± 0
5g20 ± 015 ± 025 ± 0
5h35 ± 020 ± 025 ± 0
5i55 ± 050 ± 065 ± 0
5j25 ± 030 ± 010 ± 0
5k10 ± 025 ± 015 ± 0
5l50 ± 040 ± 060 ± 0
5m005 ± 0
5n20 ± 015 ± 030 ± 0
5o55 ± 045 ± 065 ± 0
5p20 ± 025 ± 025 ± 0
5q30 ± 015 ± 015 ± 0
5r005 ± 0
5s30 ± 025 ± 015 ± 0
5t20 ± 015 ± 020 ± 0
5u20 ± 010 ± 020 ± 0
pymetrozine20 ± 040 ± 050 ± 0
a Mortality at 200 mg/L, b Mortality at 100 mg/L.
Table 5. In vitro fungicidal activities of compounds 3a–3w, 5a–5u, carbendazim and chlorothalonil against 14 kinds of fungi.
Table 5. In vitro fungicidal activities of compounds 3a–3w, 5a–5u, carbendazim and chlorothalonil against 14 kinds of fungi.
CompoundFungicidal Activities (%) a at 50 mg/kg
AS bFG bPI bPC bSS bBC bRS bFC bCH bPP bRC bBM bWA bFM b
3a33 ± 113 ± 14 ± 114 ± 111 ± 112 ± 128 ± 18 ± 3021 ± 118 ± 142 ± 227 ± 211 ± 1
3b6 ± 111 ± 211 ± 123 ± 113 ± 17 ± 317 ± 247 ± 242 ± 386 ± 379 ± 135 ± 147 ± 158 ± 1
3c9 ± 238 ± 114 ± 227 ± 237 ± 118 ± 122 ± 255 ± 160 ± 185 ± 185 ± 155 ± 239 ± 153 ± 1
3d31 ± 326 ± 119 ± 137 ± 325 ± 15 ± 136 ± 112 ± 1037 ± 238 ± 225 ± 127 ± 319 ± 1
3e21 ± 126 ± 112 ± 120 ± 211 ± 111 ± 18 ± 26 ± 125 ± 172 ± 158 ± 125 ± 120 ± 221 ± 1
3f12 ± 176 ± 19 ± 210 ± 125 ± 35 ± 143 ± 235 ± 150± 165 ± 268 ± 135 ± 152 ± 238 ± 1
3g31 ± 230 ± 19 ± 110 ± 120 ± 210 ± 233 ± 145 ± 156 ± 173 ± 379 ± 165 ± 139 ± 120 ± 1
3h6 ± 138 ± 114 ± 134 ± 237 ± 336 ± 257 ± 242 ± 244 ± 160 ± 271 ± 130 ± 232 ± 136 ± 1
3i12 ± 138 ± 24 ± 224 ± 125 ± 313 ± 145 ± 232 ± 142 ± 365 ± 142 ± 140 ± 144 ± 248 ± 1
3j12 ±269 ± 114 ± 110 ± 113 ± 213 ± 126 ± 135 ± 139 ± 157 ± 156 ± 247 ± 141 ± 238 ± 1
3k6 ± 157 ± 214 ± 141 ± 115 ± 12 ± 233 ± 132 ± 257 ± 170 ± 149 ± 147 ± 133 ± 132 ± 1
3l12 ± 230 ± 24 ± 16 ± 329 ± 123 ± 240 ± 145 ± 148 ± 177 ± 172 ± 242 ± 125 ± 150 ± 1
3m12 ± 273 ± 114 ± 113 ± 215 ± 15 ± 114 ± 132 ± 246 ± 154 ± 160 ± 142 ± 144 ± 138 ± 2
3n18 ± 111 ± 19 ± 237 ± 220 ± 218 ± 145 ± 232 ± 244 ± 152 ± 149 ± 147 ± 225 ± 146 ± 2
3o25 ± 161 ± 119 ± 117 ± 120 ± 27 ± 324 ± 245 ± 150 ± 172 ± 162 ± 240 ± 130 ± 245 ± 1
3p18 ± 150 ± 114 ± 144 ± 115 ± 118 ± 119 ± 127 ± 150 ± 160 ± 256 ± 147 ± 241 ± 341 ± 3
3q12 ± 250 ± 114 ± 137 ± 134 ± 110 ± 210 ± 230 ± 156 ± 173 ± 374 ± 142 ± 239 ± 146 ± 2
3r6 ± 134 ± 123 ± 234 ± 117 ± 113 ± 122 ± 222 ± 132 ± 165 ± 250 ± 112 ± 2016 ± 1
3s6 ± 225 ± 216 ± 235 ± 117 ± 325 ± 226 ± 232 ± 235 ± 256 ± 158 ± 142 ± 131 ± 115 ± 1
3t12 ± 151 ± 14 ± 110 ± 127 ± 231 ± 254 ± 135 ± 150 ± 178 ± 262 ± 147 ± 252 ± 241 ± 3
3u12 ± 134 ± 24 ± 117 ± 124 ± 15 ± 140 ± 135 ± 144 ± 172 ± 172 ± 335 ± 139 ± 133 ± 1
3v17 ± 211 ± 111.811 ± 111 ± 27 ± 215 ± 147 ± 257 ± 183 ± 278 ± 160 ± 155 ± 258 ± 1
3w5 ± 117 ± 28 ± 311 ± 116 ± 17 ± 213 ± 147 ± 250 ± 178 ± 278 ± 140 ± 127 ± 241 ± 3
5a18 ± 361 ± 123 ± 141 ± 110 ± 15 ± 122 ± 347 ± 148 ± 278 ± 271 ± 232 ± 235 ± 240 ± 1
5b18 ± 111 ± 24 ± 217 ± 115 ± 210 ± 249 ± 160 ± 160 ±280 ± 182 ± 257 ± 242 ± 246 ± 2
5c18 ± 173 ± 114 ± 110 ± 125 ± 313 ± 124 ± 260 ± 156 ± 282 ± 184 ± 150 ± 142 ± 253 ± 1
5d25 ± 276 ± 214 ± 131 ± 124 ± 110 ± 142 ± 145 ± 244 ± 185 ± 186 ± 157 ± 150 ± 156 ± 1
5e12 ± 173 ± 34 ± 227 ± 234 ± 126 ± 145 ± 145 ± 144 ± 172 ± 182 ± 252 ± 135 ± 156 ± 1
5f25 ± 173 ± 233 ± 131 ± 129 ± 131 ± 222 ± 251 ± 156 ± 165 ± 267 ± 355 ± 139 ± 156 ± 1
5g18 ± 257 ± 214 ± 110 ± 115 ± 110 ± 149 ± 152 ± 252 ± 170 ± 271 ± 160 ± 142 ± 263 ± 1
5h18 ± 126 ± 39 ± 117 ± 116 ± 116 ± 116 ± 142 ± 149 ± 154 ± 159 ± 142 ± 134 ± 137 ± 1
5i18 ± 153 ± 19 ± 231 ± 137 ± 313 ± 110 ± 147 ± 252 ± 186 ± 280 ± 157 ± 257 ± 156 ± 2
5j12 ± 144 ± 211 ± 111 ± 223 ± 224 ± 131 ± 147 ± 245 ± 249 ± 154 ± 239 ± 138 ± 227 ± 2
5k17 ± 252 ± 115 ± 310 ± 217 ± 16 ± 124 ± 350 ± 153 ± 142 ± 152 ± 147 ± 139 ± 123 ± 1
5l50 ± 161 ± 223 ± 317 ± 124 ± 15 ± 128 ± 157 ± 252 ± 175 ± 159 ± 140 ± 135 ± 253 ± 1
5m31 ± 161 ± 233 ± 137 ± 115 ± 110 ± 215 ± 345 ± 136 ± 182 ± 164 ± 147 ± 239 ± 170 ± 1
5n10 ± 123 ± 114 ± 214 ± 130 ± 130 ± 221 ± 247 ± 241 ± 251 ± 152 ± 138 ± 125 ± 124 ± 1
5o18 ± 223 ± 14 ± 375 ± 117 ± 113 ± 110 ± 242 ± 236 ± 168 ± 259 ± 142 ± 214 ± 126 ± 1
5p9 ± 218 ± 37 ± 324 ± 218 ± 215 ± 131 ± 126 ± 229 ± 346 ± 245 ± 240 ± 116 ± 118 ± 2
5q15 ± 224 ± 29 ± 116 ± 317 ± 211 ± 217 ± 336 ± 334 ± 252 ± 257 ± 237 ± 329 ± 113 ± 1
5r25 ± 153 ± 123 ± 310 ± 115 ± 218 ± 110 ± 227 ± 144 ± 168 ± 370 ± 242 ± 125 ± 146 ± 2
5s17 ± 142 ± 213 ± 18 ± 214 ± 29 ± 314 ± 231 ± 142 ± 250 ± 356 ± 242 ± 224 ± 345 ± 1
5t12 ± 173 ± 123 ± 26 ± 112 ± 118 ± 128 ± 147 ± 256 ± 190 ± 191 ± 135 ± 139 ± 166 ± 2
5u6 ± 130 ± 114 ± 224 ± 124 ± 15 ± 110 ± 137 ± 252 ± 165 ± 267 ± 360 ± 150 ± 130 ± 1
Carbendazim c<50100100<50100<50100<50<50<50100100100<50
Chlorothalonil c73 ± 1<5086 ± 1100<5010010010073 ± 110010091 ± 191 ± 1100
a Average of three replicates. All results are expressed as the mean ± SD. b Abbreviations: AS—Alternaria solani; FG—Fusarium graminearum; PI—Phytophthora infestans; PC—Phytophthora capsici; SS—Sclerotinia sclerotiorum; BC—Botrytis cinerea; RS—Rhizoctonia solani.; FC—Fusarium oxysporum f. sp. cucumeris; CH—Cercospora arachidicola Hori; PP—Physalospora piricola; RC—Rhizoctonia cerealis; BM—Bipolaris maydis; WA—watermelon anthracnose; FM—Fusarium moniliforme. c commercial agricultural fungicides were used for comparison of antifungal activities.
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Cui, P.; Yang, Y. Synthesis and Insecticidal/Fungicidal Activities of Triazone Derivatives Containing Acylhydrazone Moieties. Molecules 2025, 30, 340. https://doi.org/10.3390/molecules30020340

AMA Style

Cui P, Yang Y. Synthesis and Insecticidal/Fungicidal Activities of Triazone Derivatives Containing Acylhydrazone Moieties. Molecules. 2025; 30(2):340. https://doi.org/10.3390/molecules30020340

Chicago/Turabian Style

Cui, Peipei, and Yan Yang. 2025. "Synthesis and Insecticidal/Fungicidal Activities of Triazone Derivatives Containing Acylhydrazone Moieties" Molecules 30, no. 2: 340. https://doi.org/10.3390/molecules30020340

APA Style

Cui, P., & Yang, Y. (2025). Synthesis and Insecticidal/Fungicidal Activities of Triazone Derivatives Containing Acylhydrazone Moieties. Molecules, 30(2), 340. https://doi.org/10.3390/molecules30020340

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