Synthesis and Characterization of some Novel 2-(4-(1-substitutedbenzimidazole-2-yl) thiazole-2-ylamino)-4-Arylthiazole Derivatives and Investigation of their Herbicidal Effects on the Seeds of Lepidium sativum L.

Öz

Herbicides used to fight with allopathic plants causing harmful effect in agricultural lands are very important to obtain good agricultural products. To interpret of herbicidal effect a series of original compounds synthesized to investigate phytotoxic effects. For this, firstly, 2-acetylbenzimidazole has been obtained with many steps. After, it has been condensed 2-aminothiazole ring from second position of benzimidazole. After that, the amino group has been transformed to thiourea. After all of these steps, the all needed starting materials have been synthesized to attain the desired target compounds. Finally, the prepared arylacetyl bromide compounds and the starting compounds have been reacted with each other and formed new thiazole rings thus, target compounds have been synthesized. The synthesized 2-(4-(1-Substitutedbenzimidazole-2-yl)thiazole-2-ylamino)-4-arylthiazole derivatives as target compounds are novel compounds and their structures has been elucidated by using elemental analysis; IR, NMR and MS spectral data. The synthesized compounds have been tested on seeds of Lepidium sativum L. (cress) to study of their biological activities. Consequently, it was found that these compounds have phytotoxic effects based on their biological activities.

Anahtar Kelimeler

• Aminothiazole
• Benzimidazole
• Herbicidal effect
• Phytotoxic effect

Proje Numarası

169YL13

Bazı 2- (4-(1-Sübstitüebenzimidazol-2-il) tiyazol-2-ilamino)-4-Ariltiyazol Türevlerinin Sentezlenmesi, Yapılarının Aydınlatılması ve Lepidium sativum L. Tohumları Üzerinde Herbisit Etkilerinin Araştırılması

Öz

Tarımsal alanlarda sorunlara yol açan allelopatik bitkilerle mücadele için kullanılan herbisitler iyi tarım ürünleri elde edebilmesi için oldukça önemlidir. Herbisit etki yorumu yapılabilmesi için, fitotoksik etkileri incelenmek üzere bir dizi özgün bileşik sentezlenmiştir. Bunun için öncelikle 2-asetilbenzimidazol pek çok basamakta elde edilmiştir. Sonrasında ikinci konumundan bir 2-aminotiyazol halkası kapatılmıştır. Bu bileşiğin amino grubu tiyoüreye çevrilmiştir. Tüm bu adımlardan sonra hedeflenen bileşiklere ulaşmak için gerekli başlangıç maddeleri elde edilmiştir. Sonrasında hazırlanan arilasetil bromür bileşikleri yardımıyla yeni bir tiyazol halkası oluşturularak hedeflenen bileşikler sentezlenmiştir. Hedef bileşikler olan 2-(4-(1-Sübstitüebenzimidazol-2-il)tiyazol-2-ilamino)-4-ariltiyazol türevleri tamamen özgün olup, yapıları, elementel analiz, IR, NMR ve MS spektral verileri yardımıyla aydınlatılmıştır. Sentezlenen bileşiklerin, biyolojik aktiviteleri Lepidium sativum L. (tere) tohumları ile test edilmiştir. Bu biyolojik aktiviteler sonucunda bileşiklerin fitotoksik etkileri bulunmuştur.

Anahtar Kelimeler

• Aminotiyazol
• Benzimidazol
• Herbisit etki
• Fitotoksik etki

Destekleyen Kurum

Burdur Mehmet Akif Ersoy Üniversitesi, Bilimsel Araştırma Projeleri Koordinatörlüğü (MAKÜ-BAP)

Proje Numarası

169YL13

Teşekkür

Bu çalışma Mehmet Akif Ersoy Üniversitesi, Bilimsel Araştırma Projeleri Koordinatörlüğü (MAKÜ-BAP) tarafından 169YL13 proje numarası ile desteklenmiştir.

Kaynakça

1. Arjmand, F., Mohani, B., Ahmad, S. (2005). Synthesis Antibacterial, Antifungal Activity and Interaction of CT-DNA with a New Benzimidazole Derived Cu(II) Complex. European Journal of Medicinal Chemistry 40: 1103-1110.
2. Atabay, N.M., Dulger, B., Gucin, F. (2003). Synthesis and Investigation of Antimicrobial Activity of Some Bisbenzimidazole-derived Chelating Agents. European Journal of Medicinal Chemistry 38: 875-881.
3. Bhadoria, P.B.S. (2011). Allelopathy: a Natural Way Towards Weed Management. American Journal of Experimental Agriculture 1: 7-20.
4. El-Shorbagi, A.N., Hozien, Z.A., Sarhan, A.A.O. (2000). Investigation of Alkylating, Antineoplastic and Anti-HIV Potentials of the Chalcones, 2-(3-Arylpropenoyl)benzimidazole and Their Corresponding N-Methyl Derivatives. Bolletino Chimico Farmaceutico 139: 228-234.
5. Gupta, R., Sharma, D., Singh, S. (2010). Eco-Friendly Synthesis and Insecticidal Activity of Some Fluorinated 2-(N-Arylamino)-4-arylthiazoles. Phosphorus, Sulfur, and Silicon and the Related Elements 185: 1321-1331.
6. Hansch, C., Maloney, P.P., Fujita, T., Muir, R.M. (1962). Correlation of Biological Activity of Phenoxyacetic Acids with Hammett Substituent Constants and Partition Coefficients. Nature 194: 178-180.
7. Hansch, C., Muir, R.M., Fujita, T., Maloney, P.P., Geiger, F., Streich, M. (1963). The Correlation of Biological Activity of Plant Growth Regulators and Chloromycetin Derivatşves with Hammett Constants and Partition Coefficients. Journal of the American Chemical Society 85: 2817-2824.
8. Hansch, C., Fujita, T. 1964. p-- Analysis, a Method fort he Correlation of Biological Activity and Chemical Structure. Journal of the American Chemical Society 86: 1616-1626.

9. Hansch, C. (1969). Quantitative Approach to Biochemical Structure-Activity Relationships. Account of Chemical Research 2: 232-239.
10. Harley, K.L.S., Forno, I.W. (1992). Biological Control of Weeds: A Handbook for Practitioners and Students. Inkata Press, Australia.
11. Kayağil, İ., Baltacı, C. (2016). Bazı Tetrasübstitüe-imidazo[1,2-a]pirazin Bileşiklerinin Tere (Lepidium sativum L.) Tohumları Üzerindeki Herbisit Etkilerinin Araştırılması. Mehmet Akif Ersoy Üniversitesi Fen Bilimleri Enstitüsü Dergisi 7: 157-160.
12. Kiely, T., Donaldson, D., Grube, A. (2004). Pesticides Industry Sales and Usage. Office of Prevention, Pesticides and Toxic Substances, US Environment Protection Agency 16: 20-39.
13. Kim, J.S., Sun, Q., Yu, C., Liu, A., Liu, L.F., Lavoie, E.J. (1998). Quantative Structure-Activity Relationships on 5-Substituted Terbenzimidazoles as Topoisomerase in Poisons and Antitumor Agents. Bioroganic and Medicinal Chemistry 6: 163-172.
14. Matthews, C.J., Broughton, V., Bernardinelli, G., Melich, X., Brand, G., Wills, A.C., Williams, A.F. (2003). Molecular Bricklaying the Protonated Benzimidazole Moiety as a Synthon for Crystal Engineering. New Journal Chemistry 27: 354-358.
15. Özden, S., Atabey, D., Yıldız, S., Göker, H. (2005). Synthesis and Potent Antimicrobial Activity of Some Novel Methyl or Ethyl 1H-Benzimidazole-5-carboxylates Derivatives Carrying Amide or Amidinie Groups. Bioorganic and Medicinal Chemistry 13: 1587-1597.
16. Pandya, D.D., Joshi, V.V., Rajpara, K.M., Vaghani, H.V., Satodiya, H.M. (2012). Synthesis, Characterization and Antimicrobial Screening of Hybrid Molecules Containing Benzimidazole Pyrazole and Pyridine Nucleus. Medicinal Chemistry Research 21: 141-144.
17. Uluğ, E., Kadıoğlu, İ., Üremiş, İ. (1993). Türkiye’nin Yabancı Otları ve Bazı Özellikleri. Zirai Mücadele Araştırma Enstitüsü Müdürlüğü Basımı, Ankara.
18. Zhu, D., Chen, J., Xiao, H., Liu, M., Ding, J., Wu, H. (2009). Efficient and Expeditious Synthesis of di- and tri-Substituted Thiazoles in PEG Under Catalyst-Free Conditions. Collage of Chemistry and Materials Engineering. Synthetic Communications 39: 2895-2906.