Abstract
Simple and accessible pathways for the synthesis of a series of novel 6-(3,5-dimethyl-1H-pyrazol-1-yl)pyridazin-3(2H)-one derivatives including compounds with a combination of a pyrazolyl-pyridazine moiety with pyrimidine, 1,3,5-triazine and 1,3,4-oxadiazole rings in the same molecules were established. The tautomeric structures of 3-oxopyridazine and 5-thioxo-1,3,4-oxadiazole rings and also the position of their alkylation were shown. At preliminary screening the synthesised compounds showed pronounced plant growth stimulant activity. The most active compounds were selected for deeper studies and further field trials.
Keywords
References
1.
http://www.alanwood.net/pesticides/class_pesticides.html. [Accessed 1 February 2017].
2.
Vicentini C.B.
,
Romagnoli C.
,
Andreotti E.
, and
Mares D.
, J. Agric. Food Chem. , 2007 , 55 , 10331 .
3.
Li Y.
,
Zhang H.-Q.
,
Liu J.
,
Yang X.-P.
, and
Liu Z.-J.
, J. Agric. Food Chem. , 2006 , 54 , 3636 .
4.
Chen H.
,
Li Z.
, and
Han Y.
, J. Agric. Food Chem. , 2000 , 48 , 5312 .
5.
Dai H.
,
Li Y.-Q.
,
Du D.
,
Qin X.
,
Zhang X.
,
Yu H.-B.
, and
Fang J.-X.
, J. Agric. Food Chem. , 2008 , 56 , 10805 .
6.
Zou X.J.
,
Jin G.Y.
, and
Zhang Z.X.
, J. Agric. Food Chem. , 2002 , 50 , 1451 .
7.
Wu J.
,
Song B.
,
Chen H.
,
Bhadury P.
, and
Hu D.
, Molecules , 2009 , 14 , 3676 .
8.
Hackler R.E.
,
Arnold W.R.
,
Dow W.C.
,
Johnson G.W.
, and
Kaster S.V.
, J. Agric. Food Chem. , 1990 , 38 , 508 .
9.
Foks H.
,
Wisterowicz K.
,
Miszke A.
,
Broiewicz K.
,
Wisniewska K.
, and
Dabrowska-Szponar M.
, Heterocycles , 2009 , 78 , 961 .
10.
Vicentini C.B.
,
Gucione S.
,
Giurato L.
,
Ciaccio R.
,
Mares D.
, and
Forlani G.
, J. Agric. Food Chem. , 2005 , 53 , 3848 .
11.
Waldrep T.W.
,
Beck J.R.
,
Lynch M.P.
, and
Wright F.L.
, J. Agric. Food Chem. , 1990 , 38 , 541 .
12.
McFadden H.
,
Huppatz J.
,
Couzens M.
,
Kennard C.
, and
Lynch E.
, Pestic. Sci. , 1992 , 36 , 247 .
13.
Ohno R.
,
Watanabe A.
,
Nagaoka M.
,
Ueda T.
,
Sakurai H.
,
Hori M.
, and
Hirai K.
, J. Pestic. Sci. , 2004 , 29 , 96 .
14.
Siddall T.L.
,
Ouse D.G.
,
Benko Z.L.
,
Garvin G.M.
,
Jackson J.L.
,
McQuiston J.M.
,
Ricks M.J.
,
Thibault T.D.
,
Turner J.A.
,
VanHeertum J.C.
, and
Weimer M.R.
, Pest Manage. Sci. , 2002 , 58 , 1175 .
15.
Finkelstein B.
, and
Strock C.
, Pestic. Sci. , 1997 , 50 , 324 .
16.
Xu H.
,
Zou X.-M.
,
Zhu Y.-Q.
,
Liu B.
,
Tao H.-L.
,
Hu X.-H.
,
Song H.-B.
,
Hu F.-Z.
,
Wang Y.
, and
Yang H.-Z.
, Pest Manage. Sci. , 2006 , 62 , 522 .
17.
Xu H.
,
Hu X.-H.
,
Zou X.-M.
,
Liu B.
,
Zhu Y.-Q.
,
Wang Y.
,
Hu F.-Z.
, and
Yang H.-Z.
, J. Agric. Food Chem. , 2008 , 56 , 6567 .
18.
Szilagyi G.
,
Kasztreiner E.
,
Tardos L.
,
Kosa E.
,
Jaszlits L.
,
Cseh G.
,
Kovacs I.
,
Szabo N.
,
Tolnay P.
,
Elek S.
,
Elekes I.
, and
Polgari I.
, US patent: 4224325 A, 23 September 1980.
19.
Szilagyi G.
,
Kasztreiner E.
,
Tardos L.
,
Kosa E.
,
Jaszlits L.
,
Cseh A.
,
Divald
,
Tolnay P.
,
Elek S.
,
Elekes I.
, and
Polgari I.
, US patent: 4251658 A, 17 February 1981.
20.
Yassin F.
, J. Microbiol. Antimicrob. , 2010 , 2 , 93 .
21.
Ather A.
,
Chaudhry F.
,
Khan M.
,
Bueno E.
,
Khan M.
,
Aslam N.
,
Khan K.
,
Athar M.
,
Munawar M.
,
Ashraf M.
, and
Ejaz S.
, Asian J. Chem. , 2013 , 25 , 7743 .
22.
Jorda R.
,
Havlek L.
,
McNae I.W.
,
Walkinshaw D.M.
,
Voller J.
,
Sturc A.
,
Navratilova J.
,
Kuzma M.
,
Mistrík M.
,
Bartek J.
,
Strnad M.
, and
Krystof V.
, J. Med. Chem. , 2011 , 54 , 2980 .
23.
Tung Y.-S.
,
Coumar M.S.
,
Wu Y.-S.
,
Shiao H.-Y.
,
Chang J.-Y.
,
Liou J.-P.
,
Shukla P.
,
Chang C.-W.
,
Chang C.-Y.
,
Kuo C.-C.
,
Yeh T.-K.
,
Lin C.-Y.
,
Wu J.-S.
,
Wu S.-Y.
,
Liao C.-C.
, and
Hsieh H.-P.
, J. Med. Chem. , 2011 , 54 , 3076 .
24.
Shakya N.
,
Srivastav N. C.
,
Desroches N.
,
Agrawal B.
,
Kunimoto D.Y.
, and
Kumar R.
, J. Med. Chem. , 2010 , 53 , 4130 .
25.
Dorigo P.
,
Fraccarollo D.
,
Santostasi G.
,
Maragno I.
,
Floreani M.
,
Borea P.A.
,
Mosti L.
,
Sansebastiano L.
,
Fossa P.
,
Orsini F.
,
Benetollo F.
, and
Bombieri G.
, J. Med. Chem. , 1996 , 39 , 3671 .
26.
San-Felix A.
,
Velazquez S.
,
Perez-Perez M.J.
,
Balzarini J.
,
De Clercq E.
, and
Camarasa M.J.
, J. Med. Chem. , 1994 , 37 , 453 .
27.
Rauckman B.
,
Tidwell M.
,
Johnson J.
, and
Roth B.
, J. Med. Chem. , 1989 , 32 , 1927 .
28.
Srivastav N.
,
Shakya N.
,
Mak M.
,
Agrawal B.
,
Tyrrell D.
, and
Kumar R.
, J. Med. Chem. , 2010 , 53 , 7156 .
29.
Yaziji V.
,
Rodríguez D.
,
Gutiérrez-de-Terán H.
,
Coelho A.
,
Caamaño O.
,
García-Mera X.
,
Brea J.
,
Loza M.I.
,
Cadavid M.I.
, and
Sotelo E.
, J. Med. Chem. , 2011 , 54 , 457 .
30.
Stanetty P.
,
Hattinger G.
,
Schnürch M.
, and
Mihovilovic M.
, J. Org. Chem. , 2005 , 70 , 5215 .
31.
Gomktsyan T.
,
Shainova R.
,
Karapetyan A.
,
Yengoyan A.
, ChemXpress , 2016 , 9 , 183 .
32.
Hambardzumyan E.
,
Vorskanyan A.
,
Grigoryan A.
,
Yengoyan A.
, J. Chem., Biol. Phys. Sci., Section A , 2016 , 6 , 434 .
33.
Yengoyan A.
,
Mamyan S.
,
Gomktsyan T.
,
Hambardzumyan E.
,
Vorskanyan A.
,
Dovlatyan V.
,
Eliazyan K.
, and
Pivazyan V.
, Chem. Heterocycl. Comp. , 2005 , 41 , 1059 .