Abstract
A new idea for the modification of a carboxylic group in phenoxyacetic herbicides is proposed. Common herbicides, 2,4-dichlorophenoxyacetic acid (2,4-D) and 4-chloro-2-methylphenoxyacetic acid (MCPA), and their chalcogen analogs (arylthio and arylselenyl fragments instead of a phenoxy one) were used as carboxylic components in the tricomponent Passerini reaction. Cyclohexyl isocyanide and 4-isocyano-2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO-NC) were used as isocyanides. Acetone, acetaldehyde and formaldehyde were used as carbonyl components. Passerini adducts 4a–4L were obtained in yields of 32–59%. The structures of the Passerini adducts were determined using spectroscopic methods: MS, HR MS, 1H NMR, 13C NMR, 77Se NMR (if appropriate) and IR spectra (MS, HR MS, IR for the nitroxides 4k and 4L). The herbicidal activity of the Passerini adducts synthesized (4a–4L) was tested against ten weed species (at 2 kg/ha using 2,4-D and MCPA as a control). 100% herbicidal post-emergent activity was reported for 4i, 4j, 4k, 4L [a weed black mustard (Brassica nigra)], for 4k, 4L [weeds pale smartweed (Polygonum lapathifolium) and fathen (Chenopodium album)], as well as for 4k (weeds common poppy (Papaver rhoeas) and gallant soldier (Galinsoga parviflora)). The fungistatic activity of the Passerini adducts synthesized (4a–4L) was tested against six phytopathogenic fungi species (at 200 mg/L and procymidone as a control). The tested compounds showed a weak activity (% of inhibition) against: Alternaria alternata: 4g (47), 4i (26), 4j (26), 4k (50), Botrytis cinerea 4g (38), Fusarium culmorum 4g (44), Phytophthora cactorum 4i (35), 4j (35), 4k (30), Rhizoctonia solani 4g (30), 4i (24), Phytophthora infestans 4g (29), 4i (34), 4j (28), 4k (46).
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References
Andreana PR, Liu CC, Schreiber SL (2004) Stereochemical control of the Passerini reaction. Org Lett 6:4231–4233. https://doi.org/10.1021/ol0482893
Banfi L, Riva R (2005) The Passerini reaction. In: Overman L (ed) Organic reactions, vol 65. Wiley, Hoboken, pp 1–140. https://doi.org/10.1002/0471264180.or065.01
Banfi L, Basso A, Riva R (2010) Synthesis of heterocycles through classical Ugi and Passerini reactions. Top Heterocycl Chem 23:1–39. https://doi.org/10.1007/7081_2009_23
Begum S, Bharathi K, Prasad KV (2016) Mini review on the therapeutic profile of phenoxy acids and their derivatives. Int J Pharm Pharm Sci 8:66–71. https://doi.org/10.22159/ijpps.2016v8i10.5005
Bienaymé H, Hulme C, Oddon G, Schmitt P (2000) Maximizing synthetic efficiency: multi-component transformations lead the way. Chem Eur J 6:3321–3329. https://doi.org/10.1002/1521-3765(20000915)6:18%3c3321::AID-CHEM3321%3e3.0.CO;2-A
Coats JR, Klimavicz, JS, Norris EJ, Bessette SM, Lindsay AD (Kittrich Corp., Iowa State University Research Foundation, Inc.) (2018) Monoterpenoid/phenylpropanoid-containing compounds and methods of their making and use as herbicides. WO2018/39390
de Assis AT, Pinheiro PF, Praça-Fontes MM, Andrade-Vieira LF, Corrêa KB, de Assis AT, da Cruz FA, Júnior VL, Ferreira A, Soares TCB (2018) Toxicity of thymol, carvacrol and their respective phenoxyacetic acids in Lactuca sativa and Sorghum bicolor. Industrial Crops Prod 114:59–67. https://doi.org/10.1016/j.indcrop.2018.01.071
Ding G, Guo D, Zhang W, Han P, Punyapitak D, Guo M, Zhang Z, Wang B, Li J, Cao Y (2019) Preparation of novel auxinic herbicide derivatives with high-activity and low-volatility by me-too method. Arab J Chem 12:4707–4718. https://doi.org/10.1016/j.arabjc.2016.09.001
Dömling A (2002) Recent advances in isocyanide-based multicomponent chemistry. Curr Opin Chem Biol 6:306–313. https://doi.org/10.1016/S1367-5931(02)00328-9
Dömling A (2005) The discovery of new isocyanide-based multicomponent reactions. In: Zhu J, Bienaymé H (eds) Multicomponent Reactions. Wiley, New York, pp 76–94. https://doi.org/10.1002/3527605118.ch3
Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106:17–89. https://doi.org/10.1021/cr0505728
Dömling A, AlQahtani AD (2014) General introduction to MCRs: past, present, and future. In: Zhu J, Wang Q, Wang M-X (eds) Multicomponent reactions in organic synthesis. Wiley, New York, pp 1–12. https://doi.org/10.1002/9783527678174.ch01
Dömling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39:3168–3210. https://doi.org/10.1002/1521-3773(20000915)39:18%3c3168::AID-ANIE3168%3e3.0.CO;2-U
Dömling A, Wang K, Wang W (2012) Chemistry and biology of multicomponent reactions. Chem Rev 112:3083–3135. https://doi.org/10.1021/cr100233r
He HW, Yuan JL, Peng H, Chen T, Shen P, Wan SQ, Li Y, Tan HL, He YH, He JB, Li Y (2011) Studies of O, O-dimethyl alpha-(2,4-dichlorophenoxyacetoxy)ethylphosphonate (HW02) as a new herbicide. 1. Synthesis and herbicidal activity of HW02 and analogues as novel inhibitors of pyruvate dehydrogenase complex. J Agric Food Chem 59(9):4801–4813. https://doi.org/10.1021/jf104247w
Hulme C, Gore V (2003) Multi-component reactions: emerging chemistry in drug discovery, from Xylocain to Crixivan. Curr Med Chem 10:51–80. https://doi.org/10.2174/0929867033368600
Huras B, Zakrzewski J, Kiełczewska A, Krawczyk M (2017) Herbicidal and fungistatic properties of fluorine analogs of phenoxyacetic herbicides. J Fluor Chem 202:76–81. https://doi.org/10.1016/j.jfluchem.2017.08.013
Jenner G (2002) Effect of high pressure on sterically congested Passerini reactions. Tetrahedron Lett 43:1235–1238. https://doi.org/10.1016/S0040-4039(01)02397-8
Kazemizadeh AR, Ramazani A (2012) Synthetic applications of Passerini reaction. Curr Org Chem 16:418–450. https://doi.org/10.2174/138527212799499868
Lamberth C (2020) Multicomponent reactions in crop protection chemistry. Bioorg Med Chem. https://doi.org/10.1016/j.bmc.2020.115471
Manos-Turvey A, Bulloch EMM, Rutledge PJ, Baker EN, Lott JS, Payne RJ (2010) Inhibition studies of mycobacterium tuberculosis salicylate synthase (MbtI). ChemMedChem 5:1067–1079. https://doi.org/10.1002/cmdc.201000137
Orru RVA, de Greef M (2003) Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds. Synthesis. https://doi.org/10.1055/s-2003-40507
Ort O, Doeller U, Willy Reissel W, Lindell SD, Hough TL, Simpson DJ, Jimmy P, Chung JP (1997) alpha-Hydroxyarylacetamides: a new class of fungicidally active compounds. Pestic Sci 50:331–333
Peng H, Deng X, Gao L, Tan X, He H (2014) Synthesis and herbicidal activities of 2-methylpropan-2-aminium O-methyl 1-(substituted phenoxyacetoxy)alkylphosphonates. Chem Res Chinese Univ 30(1):82–86. https://doi.org/10.1007/s40242-014-3203-2
Riva R, Banfi L, Basso A (2012) The Passerini reaction. In: Müller TJJ (ed), Science of synthesis multicomponent reaction, vol 1. Thieme, Stuttgart, pp 327–414
Sheikholeslami-Farahani F, Shahvelayati AS (2013) Synthesis of unsaturated acyloxybenzothiazoleamides via the Passerini three-component reaction. Comb Chem High Throughput Screen 16:726–730. https://doi.org/10.2174/13862073113169990041
Sun GX, Sun ZH, Yang MY, Liu XH, Ma Y, Wei YY (2013) Design, synthesis, biological activities and 3D-QSAR of new N,N0-diacylhydrazines containing 2,4-dichlorophenoxy moieties. Molecules 18(12):14876–14891. https://doi.org/10.3390/molecules181214876
Tiwari TN, Chansouria JPN, Dubey NK (2003) Antimycotic potency of some essential oils in the treatment of induced dermatomycosis of an experimental animal. Pharm Biol 41:351–356. https://doi.org/10.1076/phbi.41.5.351.15935
Ugi I, Werner B, Dömling A (2003) The chemistry of isocyanides, their multicomponent reactions and their libraries. Molecules 8:53–66. https://doi.org/10.3390/80100053
Wang Z (2010) Passerini Reaction 479. In: Wang Z (ed) Comprehensive Organic Name Reactions and Reagents. Wiley, New York, pp 2121–2125. https://doi.org/10.1002/9780470638859.conrr479
Wang W, He HW, Zuo N, He HF, Peng H, Tan XS (2012) Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy) alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one. J Agric Food Chem 60(31):7581–7587. https://doi.org/10.1021/jf301829m
Wang T, Wang W, Peng H, He H (2015) Synthesis and biological activity of 1-(substituted phenoxyacetoxy)-1-(pyridin-2-yl or thien-2-yl)methylphosphonates. J Heterocyc Chem 52(1):173–179. https://doi.org/10.1002/jhet.1944
Weber WP, Gokel GW, Ugi IK (1972) Phase transfer catalysis in the Hofmann carbylamine reaction. Angew Chem Int Ed 11:530–531, Angew. Chem. 84, 587. https://doi.org/10.1002/anie.197205301
Yu S-J, Zhu C, Bian Q, Cui C, Du X-J, Li Z-M, Zhao W-G (2014) Novel ultrasound-promoted parallel synthesis of trifluoroatrolactamide library via a one-pot Passerini/hydrolysis reaction sequence and their fungicidal activities. ACS Comb Sci 16:17–23. https://doi.org/10.1021/co400111r
Zakrzewski J, Hupko J (2003) Efficient synthesis of 4-isocyano-2,2,6,6-tetramethylpiperidine-1-oxyl. Org Prep Proced Int 35:387–390. https://doi.org/10.1080/00304940309355845
Zakrzewski J, Krawczyk M (2008) Reactions of nitroxides, part 7: synthesis of novel nitroxide selenoureas. Heteroat Chem 19:549–556. https://doi.org/10.1002/hc.20454
Zakrzewski J, Krawczyk M (2014) Reactions of nitroxides XIV. Analogs of phenoxy carboxylic herbicides based on the piperidine scaffold; unexpected fungicidal activity of the 2-[(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)oxy]butanoic acid. Heterocycl Commun 20:89–91. https://doi.org/10.1515/hc-2013-0169
Zakrzewski J, Huras B, Kiełczewska A, Krawczyk M (2018) Selenium analogs of phenoxypropionic and phenoxyacetic herbicides. Zeit Naturforsch B 73(12):1005–1013. https://doi.org/10.1515/znb-2018-0128
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This work was supported by the Polish Ministry of Science and Higher Education, 4180/E-142/S/2019.
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Żelechowski, K., Zakrzewski, J., Huras, B. et al. Synthesis and herbicidal and fungistatic evaluation of Passerini adducts bearing phenoxyacetic moieties. Chem. Pap. 75, 3047–3059 (2021). https://doi.org/10.1007/s11696-021-01528-8
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DOI: https://doi.org/10.1007/s11696-021-01528-8