401:
276:
984:
979:
989:
30:
592:
1103:
39:
1178:
587:
67:
582:
577:
1050:
58:
1115:
903:
780:
1732:
Faria, Jéssica Venância; Vegi, Percilene
Fazolin; Miguita, Ana Gabriella Carvalho; dos Santos, Maurício Silva; Boechat, Nubia; Bernardino, Alice Maria Rolim (1 November 2017). "Recently reported biological activities of pyrazole compounds".
1383:
Nozari, M., Addison, A., Reeves, G.T, Zeller, M., Jasinski, J.P., Kaur, M., Gilbert, J. G., Hamilton, C. R., Popovitch, J. M., Wolf, L. M., Crist, L. E., Bastida, N., (2018) Journal of heterocyclic
Chemistry 55, 6, 1291-1307.
600:
557:
1311:
1184:
710:
714:
1496:
Outirite, Moha; Lebrini, Mounim; Lagrenée, Michel; Bentiss, Fouad (2008). "New one step synthesis of 3,5-disubstituted pyrazoles under microwave irradiation and classical heating".
793:
1304:
1917:
1469:
450:
706:
1716:
1263:
1353:
Schmidt, Andreas; Dreger, Andrij (2011). "Recent
Advances in the Chemistry of Pyrazoles. Properties, Biological Activities, and Syntheses".
1873:
A. Schmidt; A. Dreger (2011). "Recent
Advances in the Chemistry of Pyrazoles. Part 2. Reactions and N-Heterocyclic Carbenes of Pyrazole".
1829:
Jeschke, Peter (2021). "Current Trends in the Design of
Fluorine-Containing Agrochemicals". In Szabó, Kálmán; Selander, Nicklas (eds.).
1699:
Kabi, Arup K.; Sravani, Sattu; Gujjarappa, Raghuram; et al. (2022). "Overview on
Biological Activities of Pyrazole Derivatives".
1846:
1813:
1498:
1337:
415:
1796:
Walter, Harald (2016). "Fungicidal
Succinate-Dehydrogenase-Inhibiting Carboxamides". In Lamberth, Clemens; Dinges, Jürgen (eds.).
1912:
746:
694:
800:
656:
358:
591:
379:
754:
586:
1247:
844:
534:
1156:. The pyrazole ring is found within a variety of pesticides as fungicides, insecticides and herbicides, including
283:
644:
750:
1907:
1279:
1188:
914:
678:
576:
271:
1535:
983:
1172:. Pyrazole moieties are listed among the highly used ring systems for small molecule drugs by the US FDA
1126:
1606:
1033:
1025:
614:
581:
569:
213:
101:
861:
of the conjugate acid 2.49 at 25 °C). Pyrazoles are also a class of compounds that have the ring C
978:
1652:
1200:
85:
988:
1244:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1157:
1041:
682:
396:
127:
742:
698:
1902:
1852:
1678:
1169:
1029:
738:
666:
648:
173:
161:
662:
686:
1842:
1809:
1758:
1750:
1712:
1670:
1460:
1404:
1333:
1259:
1102:
1086:
1078:
1037:
1005:
1882:
1834:
1801:
1742:
1704:
1660:
1643:
1597:
1544:
1507:
1478:
1442:
1363:
1355:
1251:
1177:
1141:
820:
670:
473:
730:
367:
29:
1619:
894:
702:
302:
233:
137:
1656:
400:
275:
193:
771:
66:
1049:
1896:
1856:
918:
718:
524:
514:
264:
1682:
1565:
762:
726:
38:
1426:
1205:
1165:
1114:
1013:
1001:
902:
674:
1775:
690:
347:
1708:
1399:
1330:
The
Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications
1255:
1187:
is used in the manufacture of six commercial fungicides which are inhibitors of
1130:
836:
640:
57:
1886:
1838:
1805:
1367:
1746:
1446:
874:
501:
224:
1754:
1574:-pyrazole from hydrazones and/or ketones monitored by high resolution ESI-MS"
1482:
636:
1511:
1221:
1211:
1137:
1118:
1090:
1009:
922:
890:
870:
1762:
1674:
1531:-pyrazoles from chalcones and hydrazine under mechanochemical ball milling"
869:
with adjacent nitrogen atoms. Notable drugs containing a pyrazole ring are
722:
624:
1549:
1526:
1161:
1149:
1145:
1070:
1000:
The term pyrazole was given to this class of compounds by German
Chemist
910:
886:
632:
244:
1798:
Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals
253:
1786:
Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J Med Chem 2014, 57, 5845.
1224:, another analogue, the nitrogen atom in position 1 replaced by oxygen.
334:
284:
1703:. Materials Horizons: From Nature to Nanomaterials. pp. 229–306.
1635:"alpha-Amino-beta-(pyrazolyl-N) propionic acid: a new amino-acid from
628:
1665:
1634:
1082:
840:
204:
1464:
1430:
1385:
770:
Except where otherwise noted, data are given for materials in their
620:
322:
1153:
1113:
1094:
816:
184:
160:
150:
1136:
In medicine, derivatives of pyrazole are widely used, including
758:
313:
1525:
Zhang, Ze; Tan, Ya-Jun; Wang, Chun-Shan; Wu, Hao-Hao (2014).
885:
Pyrazoles are synthesized by the reaction of α,β-unsaturated
734:
384:
65:
56:
37:
28:
1004:
in 1883. In a classical method developed by German chemist
529:
186 to 188 °C (367 to 370 °F; 459 to 461 K)
909:
Substituted pyrazoles are prepared by condensation of 1,3-
1185:
3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid
519:
66 to 70 °C (151 to 158 °F; 339 to 343 K)
788:
1431:"Action of ethyl acetoacetate on phenylhydrazine. I"
843:
atoms and two adjacent nitrogen atoms, which are in
1305:"Dissociation constants of organic acids and bases"
1570:-catalyzed synthesis of azines and 3,5-diphenyl-1
1633:Noe, F. F.; Fowden, L.; Richmond, P. T. (1959).
346:
1398:Johnson, William S.; Highet, Robert J. (1963).
136:
1470:Berichte der deutschen chemischen Gesellschaft
1036:at high temperatures (~200 °C) to form a
8:
973:A wide variety of pyrazoles can be made so:
839:characterized by a 5-membered ring of three
1214:, structural analogue of pyrazole with two
987:
982:
977:
424:InChI=1S/C3H4N2/c1-2-4-5-3-1/h1-3H,(H,4,5)
399:
274:
232:
17:
1918:Substances discovered in the 19th century
1664:
1548:
1379:
1377:
434:InChI=1/C3H4N2/c1-2-4-5-3-1/h1-3H,(H,4,5)
366:
1694:
1692:
1234:
1008:in 1898, pyrazole was synthesized from
455:
420:
395:
252:
1615:
1604:
1578:Indian Journal of Chemistry, Section B
1465:"Pyrazol aus Acetylen und Diazomethan"
265:
1564:Lasri, Jamal; Ismail, Ali I. (2018).
1125:In 1959, the first natural pyrazole,
427:Key: WTKZEGDFNFYCGP-UHFFFAOYSA-N
212:
192:
7:
1735:Bioorganic & Medicinal Chemistry
1527:"One-pot synthesis of 3,5-diphenyl-1
1028:to form a class of ligands known as
873:(celebrex) and the anabolic steroid
437:Key: WTKZEGDFNFYCGP-UHFFFAOYAW
337:
321:
1328:Eicher, T.; Hauptmann, S. (2003).
1317:from the original on 12 July 2017.
14:
1595:Fowden; Noe; Ridd; White (1959).
1499:Journal of Heterocyclic Chemistry
1386:https://doi.org/10.1002/jhet.3155
847:. Pyrazole is a weak base, with p
1176:
1101:
1048:
901:
778:
590:
585:
580:
575:
491:
485:
917:-type reactions). For example,
774:(at 25 °C , 100 kPa).
1248:The Royal Society of Chemistry
1121:, a pyrazole-derived analgesic
1032:. Pyrazole itself reacts with
479:
1:
1129:, was isolated from seeds of
1097:is produced as a by-product.
1081:in the presence of elemental
1075:)-1,3-diphenylprop-2-en-1-one
106:1,2-Diazacyclopenta-2,4-diene
925:gives 3,5-dimethylpyrazole:
1833:. Wiley. pp. 363–395.
1800:. Wiley. pp. 405–425.
1709:10.1007/978-981-16-8399-2_7
1701:Nanostructured Biomaterials
1332:(2nd ed.). Wiley-VCH.
1256:10.1039/9781849733069-FP001
1069:-pyrazole is produced when
52:
24:
1934:
1887:10.2174/138527211796378497
1839:10.1002/9783527825158.ch11
1806:10.1002/9783527693931.ch31
1414:, vol. 4, p. 351
1368:10.2174/138527211795378263
1208:, fully saturated analogue
1020:Conversion to scorpionates
965:H + 2 H
815:is an organic compound of
1747:10.1016/j.bmc.2017.09.035
1447:10.1002/cber.188301602194
1218:-adjacent nitrogen atoms.
881:Preparation and reactions
768:
556:
551:
466:
446:
411:
120:
112:
100:
84:
79:
51:
23:
1831:Organofluorine Chemistry
1483:10.1002/cber.18980310363
1284:pubchem.ncbi.nlm.nih.gov
657:Precautionary statements
1512:10.1002/jhet.5570450231
1189:succinate dehydrogenase
1400:"3,5-Dimethylpyrazole"
1122:
70:
61:
42:
33:
1913:Simple aromatic rings
1250:. 2014. p. 141.
1117:
1034:potassium borohydride
1026:potassium borohydride
1024:Pyrazoles react with
102:Systematic IUPAC name
69:
60:
41:
32:
1566:"Metal-free and FeCl
1550:10.3987/COM-13-12867
1201:3,5-dimethylpyrazole
86:Preferred IUPAC name
1657:1959Natur.184...69B
1127:1-pyrazolyl-alanine
1110:Occurrence and uses
949: → (CH
509: g·mol
174:Beilstein Reference
20:
1637:Citrullus vulgaris
1461:von Pechmann, Hans
1435:Chemische Berichte
1123:
845:ortho-substitution
801:Infobox references
71:
62:
43:
34:
18:
1881:(16): 2897–2970.
1741:(21): 5891–5903.
1718:978-981-16-8398-5
1614:Missing or empty
1412:Collected Volumes
1405:Organic Syntheses
1265:978-0-85404-182-4
1093:in which case an
1087:sodium persulfate
1079:hydrazine hydrate
1038:tridentate ligand
1006:Hans von Pechmann
941: + N
809:Chemical compound
807:
806:
615:Hazard statements
380:CompTox Dashboard
162:Interactive image
75:
74:
47:
46:
1925:
1890:
1861:
1860:
1826:
1820:
1819:
1793:
1787:
1784:
1778:
1773:
1767:
1766:
1729:
1723:
1722:
1696:
1687:
1686:
1668:
1666:10.1038/184069a0
1630:
1624:
1623:
1617:
1612:
1610:
1602:
1598:Proc. Chem. Soc.
1592:
1586:
1585:
1561:
1555:
1554:
1552:
1522:
1516:
1515:
1493:
1487:
1486:
1477:(3): 2950–2951.
1457:
1451:
1450:
1423:
1417:
1415:
1408:
1395:
1389:
1381:
1372:
1371:
1362:(9): 1423–1463.
1356:Curr. Org. Chem.
1350:
1344:
1343:
1325:
1319:
1318:
1316:
1309:
1301:
1295:
1294:
1292:
1290:
1276:
1270:
1269:
1242:"Front Matter".
1239:
1180:
1142:COX-2 inhibitors
1105:
1089:, or by using a
1077:is reacted with
1052:
991:
986:
981:
913:with hydrazine (
905:
791:
785:
782:
781:
764:
760:
756:
752:
748:
744:
740:
736:
732:
728:
724:
720:
716:
712:
708:
704:
700:
696:
692:
688:
684:
680:
676:
672:
668:
664:
650:
646:
642:
638:
634:
630:
626:
622:
594:
589:
584:
579:
508:
493:
487:
481:
474:Chemical formula
404:
403:
388:
386:
370:
350:
339:
325:
303:Gmelin Reference
286:
278:
267:
256:
236:
216:
196:
164:
140:
53:
25:
21:
1933:
1932:
1928:
1927:
1926:
1924:
1923:
1922:
1893:
1892:
1875:Curr. Org. Chem
1872:
1870:
1868:Further reading
1865:
1864:
1849:
1828:
1827:
1823:
1816:
1795:
1794:
1790:
1785:
1781:
1774:
1770:
1731:
1730:
1726:
1719:
1698:
1697:
1690:
1651:(4688): 69–70.
1632:
1631:
1627:
1613:
1603:
1594:
1593:
1589:
1569:
1563:
1562:
1558:
1524:
1523:
1519:
1495:
1494:
1490:
1459:
1458:
1454:
1425:
1424:
1420:
1410:
1397:
1396:
1392:
1382:
1375:
1352:
1351:
1347:
1340:
1327:
1326:
1322:
1314:
1307:
1303:
1302:
1298:
1288:
1286:
1278:
1277:
1273:
1266:
1241:
1240:
1236:
1231:
1197:
1112:
1063:
1022:
998:
968:
964:
960:
956:
952:
948:
944:
940:
936:
932:
895:dehydrogenation
893:and subsequent
883:
868:
864:
860:
853:
834:
830:
826:
819:group with the
810:
803:
798:
797:
796: ?)
787:
783:
779:
775:
659:
617:
603:
572:
543:
506:
496:
490:
484:
476:
462:
459:
454:
453:
442:
439:
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429:
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425:
419:
418:
407:
389:
382:
373:
353:
340:
328:
305:
296:
259:
239:
219:
199:
176:
167:
154:
143:
130:
116:
108:
107:
96:
95:
12:
11:
5:
1931:
1929:
1921:
1920:
1915:
1910:
1908:Aromatic bases
1905:
1895:
1894:
1869:
1866:
1863:
1862:
1847:
1821:
1814:
1788:
1779:
1768:
1724:
1717:
1688:
1639:(water melon)"
1625:
1587:
1567:
1556:
1543:(1): 103–112.
1517:
1506:(2): 503–505.
1488:
1452:
1418:
1390:
1373:
1345:
1338:
1320:
1296:
1271:
1264:
1233:
1232:
1230:
1227:
1226:
1225:
1219:
1209:
1203:
1196:
1193:
1182:
1181:
1111:
1108:
1107:
1106:
1065:3,5-Diphenyl-1
1062:
1057:3,5-Diphenyl-1
1055:
1054:
1053:
1021:
1018:
997:
994:
993:
992:
971:
970:
966:
962:
958:
954:
950:
946:
942:
938:
934:
930:
907:
906:
882:
879:
866:
862:
858:
851:
832:
828:
824:
808:
805:
804:
799:
777:
776:
772:standard state
769:
766:
765:
715:P305+P354+P338
711:P305+P351+P338
660:
655:
652:
651:
618:
613:
610:
609:
604:
599:
596:
595:
573:
568:
565:
564:
554:
553:
549:
548:
545:
541:
531:
530:
527:
521:
520:
517:
511:
510:
504:
498:
497:
494:
488:
482:
477:
472:
469:
468:
464:
463:
461:
460:
457:
449:
448:
447:
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443:
441:
440:
436:
433:
432:
430:
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414:
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412:
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392:
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378:
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371:
363:
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355:
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343:
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318:
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165:
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155:
148:
145:
144:
142:
141:
133:
131:
126:
123:
122:
118:
117:
114:
110:
109:
105:
104:
98:
97:
89:
88:
82:
81:
77:
76:
73:
72:
63:
49:
48:
45:
44:
35:
13:
10:
9:
6:
4:
3:
2:
1930:
1919:
1916:
1914:
1911:
1909:
1906:
1904:
1901:
1900:
1898:
1891:
1888:
1884:
1880:
1876:
1867:
1858:
1854:
1850:
1848:9783527347117
1844:
1840:
1836:
1832:
1825:
1822:
1817:
1815:9783527339471
1811:
1807:
1803:
1799:
1792:
1789:
1783:
1780:
1777:
1772:
1769:
1764:
1760:
1756:
1752:
1748:
1744:
1740:
1736:
1728:
1725:
1720:
1714:
1710:
1706:
1702:
1695:
1693:
1689:
1684:
1680:
1676:
1672:
1667:
1662:
1658:
1654:
1650:
1646:
1645:
1640:
1638:
1629:
1626:
1621:
1608:
1600:
1599:
1591:
1588:
1584:(3): 362–373.
1583:
1579:
1575:
1573:
1560:
1557:
1551:
1546:
1542:
1538:
1537:
1532:
1530:
1521:
1518:
1513:
1509:
1505:
1501:
1500:
1492:
1489:
1484:
1480:
1476:
1473:(in German).
1472:
1471:
1466:
1462:
1456:
1453:
1448:
1444:
1441:: 2597–2599.
1440:
1436:
1432:
1428:
1422:
1419:
1413:
1407:
1406:
1401:
1394:
1391:
1387:
1380:
1378:
1374:
1369:
1365:
1361:
1358:
1357:
1349:
1346:
1341:
1339:3-527-30720-6
1335:
1331:
1324:
1321:
1313:
1306:
1300:
1297:
1285:
1281:
1275:
1272:
1267:
1261:
1257:
1253:
1249:
1246:. Cambridge:
1245:
1238:
1235:
1228:
1223:
1220:
1217:
1213:
1210:
1207:
1204:
1202:
1199:
1198:
1194:
1192:
1190:
1186:
1179:
1175:
1174:
1173:
1171:
1167:
1163:
1159:
1158:fenpyroximate
1155:
1151:
1147:
1143:
1139:
1134:
1132:
1128:
1120:
1116:
1109:
1104:
1100:
1099:
1098:
1096:
1092:
1088:
1084:
1080:
1076:
1074:
1068:
1060:
1056:
1051:
1047:
1046:
1045:
1043:
1039:
1035:
1031:
1027:
1019:
1017:
1015:
1011:
1007:
1003:
995:
990:
985:
980:
976:
975:
974:
928:
927:
926:
924:
920:
919:acetylacetone
916:
912:
904:
900:
899:
898:
896:
892:
888:
880:
878:
876:
872:
857:
850:
846:
842:
838:
822:
818:
814:
802:
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1206:Pyrazolidine
1183:
1166:tebufenpyrad
1140:and similar
1135:
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1014:diazomethane
1002:Ludwig Knorr
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121:Identifiers
113:Other names
91:
15:
1289:17 February
1170:tolfenpyrad
1131:watermelons
1030:scorpionate
837:heterocycle
835:H. It is a
601:Signal word
467:Properties
272:100.005.471
214:ChEMBL15967
194:CHEBI:17241
115:1,2-Diazole
1897:Categories
1280:"Pyrazole"
1229:References
875:stanozolol
570:Pictograms
502:Molar mass
368:3QD5KJZ7ZJ
225:ChemSpider
149:3D model (
128:CAS Number
1903:Pyrazoles
1857:234149806
1755:0968-0896
1427:Knorr, L.
1222:isoxazole
1212:imidazole
1138:celecoxib
1119:Celecoxib
1091:hydrazone
1061:-pyrazole
1042:Tp ligand
1040:known as
1010:acetylene
923:hydrazine
911:diketones
891:hydrazine
887:aldehydes
871:celecoxib
755:P403+P233
751:P362+P364
747:P361+P364
743:P337+P317
739:P332+P317
707:P304+P340
703:P302+P352
699:P301+P317
679:P264+P265
561:labelling
293:206-017-1
285:EC Number
94:-Pyrazole
19:Pyrazole
1763:28988624
1683:37499048
1675:13804343
1463:(1898).
1429:(1883).
1312:Archived
1195:See also
1162:fipronil
1150:betazole
1146:zaleplon
813:Pyrazole
552:Hazards
535:Basicity
245:DrugBank
138:288-13-1
1653:Bibcode
996:History
854:11.5 (p
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254:DB02757
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607:Danger
507:68.079
458:c1cnc1
451:SMILES
323:C00481
205:ChEMBL
80:Names
1853:S2CID
1679:S2CID
1315:(PDF)
1308:(PDF)
1154:CDPPB
1095:azine
915:Knorr
889:with
817:azole
547:11.5
416:InChI
308:1360
185:ChEBI
151:JSmol
1843:ISBN
1810:ISBN
1759:PMID
1751:ISSN
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