Synthesis and herbicidal activity of novel pyrazolo[3,4-d]pyrimidin-4-one derivatives containing aryloxyphenoxypropionate moieties

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 8, 2007, Pages 2203-2209

  Liu, Hui ^a   Wang, Hong Qing ^b   Liu, Zhao Jie ^a  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

^b UNIVERSITY OF SOUTH CHINA   (China)

Author keywords

Aza Wittig reaction; Herbicide; Pyrazolo 3,4 d pyrimidin 4 one; Synthesis

Indexed keywords

ISOCYANIC ACID DERIVATIVE; PHENOL DERIVATIVE; PHOSPHORANE DERIVATIVE; PROPIONIC ACID DERIVATIVE; PYRIMIDINE DERIVATIVE;

ANNULATION REACTION; ARTICLE; BIOASSAY; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; GRASS; HERBICIDAL ACTIVITY; HORNER REACTION; INFRARED RADIATION; MALE; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; ECHINOCHLOA; HERBICIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLANT COMPONENTS; PROPIONATES; PYRAZOLES; PYRIMIDINES;

ECHINOCHLOA CRUS-GALLI;

EID: 33947602611     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.01.083     Document Type: Article

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49. 5S: C, 63.62; H, 4.58; N, 10.60. Found: C, 63.49; H, 4.67; N, 10.42.
50. 5S: C, 57.93; H, 4.12; N, 9.95. Found: C, 60.00; H, 4.01; N, 10.12.
51. 5S: C, 64.19; H, 4.83; N, 10.33. Found: C, 64.35; H, 5.01; N, 10.22.
52. 5S: C, 61.53; H, 4.24; N, 10.25. Found: C, 61.24; H, 4.36; N, 10.38.
53. 5S: C, 64.19; H, 4.83; N, 10.33. Found: C, 64.35; H, 4.67; N, 10.54.
54. 5S: C, 60.36; H, 4.37; N, 9.71. Found: C, 60.57; H, 4.20; N, 9.69.
55. 5S: C, 64.73; H, 5.07; N, 10.0. Found: C, 64.87; H, 4.82; N, 10.04.
56. 5S: C, 64.19; H, 4.83; N, 10.33. Found: C, 64.32; H, 4.64; N, 10.37.
57. 5S: C, 68.34; H, 5.10; N, 8.85. Found: C, 68.32; H, 4.94; N, 8.77.
58. 5S: C, 67.94; H, 4.89; N, 9.06. Found: C, 68.02; H, 4.94; N, 8.98.
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61. 5S: C, 65.25; H, 5.30; N, 9.82. Found: C, 65.46; H, 5.41; N, 10.01.
62. 3 and 20 mL water. A great deal white solid was precipitated with stirring, after filtering, pure compounds 7 were obtained after recrystallization with ethanol.
63. 7S: C, 59.99; H, 4.32; N, 9.99. Found: C, 59.89; H, 4.45; N, 10.12.
64. 7S: C, 56.52; H, 3.90; N, 9.42. Found: C, 56.50; H, 4.01; N, 9.32.
65. 7S: C, 60.62; H, 4.56; N, 9.75. Found: C, 60.52; H, 4.77; N, 9.89.
66. 7S: C, 58.13; H, 4.01; N, 9.68. Found: C, 58.24; H, 4.11; N, 9.79.
67. 7S: C, 60.62; H, 4.56; N, 9.75. Found: C, 60.53; H, 4.67; N, 9.54.
68. 7S: C, 57.19; H, 4.14; N, 9.20. Found: C, 57.31; H, 4.20; N, 9.09.
69. 7S: C, 61.21; H, 4.79; N, 9.52. Found: C, 61.33; H, 4.82; N, 9.76.
70. 7S: C, 60.62; H, 4.56; N, 9.75. Found: C, 60.53; H, 4.48; N, 9.87.
71. 7S: C, 65.05; H, 4.85; N, 8.43. Found: C, 65.14; H, 4.92; N, 8.57.
72. 7S: C, 64.60; H, 4.65; N, 8.61. Found: C, 64.75; H, 4.81; N, 8.68.
73. 7S: C, 61.21; H, 4.79; N, 9.52. Found: C, 61.18; H, 4.83; N, 9.44.
74. 5S: C, 57.83; H, 4.37; N, 8.99. Found: C, 57.91; H, 4.43; N, 8.97.
75. 7S: C, 61.78; H, 5.02; N, 9.30. Found: C, 61.85; H, 5.14; N, 9.29.
76. Single crystal X-ray diffraction data for 6h at 292 K on a Bruker Smart Apex Area CCD equipped with Mo Ka radiation (λ = 0.71073 Ǻ). Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC-606703. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or email: deposit@ccdc.cam.ac.uk).
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79. Herbicidal testing of the newly synthesized compounds 6 and 7 was carried out in a plant growth room. Temperature 23 ± 1 °C, RH 60 ± 5%, light intensity 10 Klux, and photoperiod 8 h/day. Twenty seeds of each one of weed species including rape and barnyard grass were chosen for testing. Seedlings were grown in the test plate of 9 cm diameter containing two pieces of filter paper and 9 mL solution of the tested compound (100 and 10 mg/L, respectively). Distilled water was used as comparison compound. The herbicidal activity was assessed as the inhibition rate in comparison with the distilled water. The herbicidal rating score based on visual observation. Range from 0% to 100%, 0% means no effect, 100% means complete killing.
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