Abstract
A new kind of anthranilic diamides containing 5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine were designed and synthesised. Their structures were identified by means of elemental analysis, IR, 1H NMR and MS spectra. As the key intermediate, ethyl 5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate (
Keywords
References
1.
Tohnishi
M.
,
Nakao
H.
,
Kohno
E.
,
Nishida
T.
,
Furuya
T.
,
Shimizu
T.
,
Seo
A.
,
Sakata
K.
,
Fujioka
S.
, and
Kanno
H.
, EP 919 542 , 1999 .
2.
Konze
J.
,
Andersch
W.
,
Stübler
D.
, and
Fischer
R.
, WO 2 004 034 786 , 2004 .
3.
Lahm
G.P.
,
Myers
B.J.
,
Selby
T.P.
, and
Stevenson
T.M.
, WO 2 001 070 671 , 2001 .
4.
Nauen
R.
, Pest Manag. Sci. , 2006 , 62 , 690 .
5.
Gewehr
M.
,
Puhl
M.
,
Dickhaut
J.
,
Bastiaans
H.M.M.
,
Anspaugh
D.D.
,
Kuhn
D.G.
,
Oloumi-Sadeghi
H.
, and
Armes
N.
, WO 2 007 082 841 , 2007 .
6.
Muehlebach
M.
,
Jeanguenat
A.
, and
Hall
R.G.
, WO 2 007 080 131 , 2007 .
7.
Lahm
G.P.
,
Stevenson
T.M.
,
Selby
T.P.
,
Freudenberger
J.H.
,
Cordova
D.
,
Flexner
L.
,
Bellin
C.A.
,
Dubas
C.M.
,
Smith
B.K.
,
Hughes
K.A.
,
Hollingshaus
J.G.
,
Clark
C.E.
, and
Benner
E.A.
, Bioorg. Med. Chem. Lett. , 2007 , 17 , 6274 .
8.
Theisswn
R.J.
, US 4 340 417 , 1982 .
9.
Kuhnt
T.D.
,
Haug
M.
,
Jelich
K.
,
Stenzel
K.
,
Dehne
H.-W.
,
Haensler
G.
,
Wachendorff-Neumann
U.
,
Erdelen
C.
,
Kugler
M.
, and
Schrage
H.
, DE 4 428 380 , 1996 .
10.
Kleschick
W.A.
,
Costales
M.J.
,
Dunbar
J.E.
,
Meikle
R.W.
,
Monte
W.T.
,
Pearson
N.R.
,
Snider
S.W.
, and
Vinogradoff
A.P.
, Pestic. Sci. , 1990 , 29 , 341 .
11.
Reiter
J.
,
Bercz
G.
,
Zsila
G.
,
Petocz
L.
,
Gigler
G.
,
Fekete
M.
,
Szecsey
M.
,
Szirt
E.
, and
Rohacs
L.
, EP 500 136 , 1992 .
12.
Cavallaro
C.L.
,
Harikrishnan
L.S.
,
Chi
F.
,
Dodd
D.
, and
Purandare
A.
, J. Comb. Chem. , 2008 , 10 , 28 .
13.
Zhang
N.
,
Ayral-Kaloustian
S.
,
Nguyen
T.
,
Afragola
J.
,
Hernandez
R.
,
Lucas
J.
,
Gibbons
J.
, and
Beyer
C.
, J. Med. Chem. , 2007 , 50 , 319 .
14.
Zhao
X-L.
,
Zhao
Y-F.
,
Guo
S-C.
,
Song
H-S.
,
Wang
D.
, and
Gong
P.
, Molecules , 2007 , 12 , 1136 .
15.
Shapiro
R.
,
Taylor
E.G.
, and
Zimmerman
W.T.
, WO 2 006 062 978 , 2006 .
16.
Lahm
G.P.
,
Selby
T.P.
,
Freudenberger
J.H.
,
Stevenson
T.M.
,
Myers
B.J.
,
Seburyamo
G.
,
Smith
B.K.
,
Flexner
L.
,
Clark
C.E.
, and
Cordova
D.
, Bioorg. Med. Chem. Lett. , 2005 , 15 , 4898 .
17.
Davis
R.F.
,
Shapiro
R.
, and
Taylor
E.D.
, WO 2 008 010 897 , 2008 .
18.
Long
D.Q.
,
Wang
Y.G.
,
Li
D.J.
, and
Wang
F.J.
, Chin. J. Org. Chem. , 2005 , 25 , 1498 .
19.
Cipens
G.E.
, and
Grinsteins
V.
, Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija , 1965 , 204 .
20.
Chernyshev
V.M.
,
Chernysheva
A.V.
, and
Taranushich
V.A.
, Russ. J. Appl. Chem. , 2006 , 79 , 783 .
21.
Tseng
C.P.
, US 4 838 925 , 1989 .
22.
Okabe
T.
,
Bhooshan
B.
,
Novinson
T.
,
Hillyard
I.W.
,
Garner
G.E.
, and
Robins
R.K.
, J. Heterocycl. Chem. , 1983 , 20 , 735 .
23.
Xu
G.
, and
Wang
Y.G.
, Org. Lett. , 2004 , 6 , 985 .
24.
Sagar
R.
, and
Park
S.B.
, J. Org. Chem. , 2008 , 73 , 3270 .
