203:
128:
443:
479:
35:
760:
738:
486:
Tribenuron has a broad spectrum of activity on commercially important broadleaf weeds and grasses but at the recommended use rate it is safe to important crops such as wheat. When introduced by DuPont, its recommended application rate was 0.015–0.03 pounds per acre (17–34 g/ha). The estimated
428:
were first disclosed in general terms in one of Levitt's patents and subsequently the ester was subject to further patenting and selected for development under the code name DPX L5300. In the final step of its synthesis, 2-methoxycarbonylbenzenesulfonyl isocyanate was
487:
use in US agriculture is mapped by the US Geological
Service and shows that from 1992 to 2018, up to 120,000 pounds (54,000 kg) were applied each year. The compound is used mainly in wheat but also in pasture.
105:
793:
649:
1295:
416:
worked extensively on sulfonylurea herbicides, following the invention of this class of herbicides by George Levitt which had led to the commercialisation of
1010:
Kreiner, Julia M.; Stinchcombe, John R.; Wright, Stephen I. (2018-04-29). "Population
Genomics of Herbicide Resistance: Adaptation via Evolutionary Rescue".
217:
953:
Miller, J.F.; Al-Khatib, Kassim (2004). "Registration of Two
Oilseed Sunflower Genetic Stocks, SURES-1 and SURES-2 Resistant to Tribenuron Herbicide".
758:, Gerald E. Lepone, "Herbicidal ortho-carbomethoxysulfonylureas", issued 1988-04-26, assigned to E. I. du Pont de Nemours and Company
634:
588:
467:
401:
1083:
1981:
1443:
736:, George Levitt, "Agricultural sulfonamides", issued 1983-05-10, assigned to E. I. du Pont de Nemours and Company
2007:
964:
681:
459:
1408:
1012:
543:
664:
369:
160:
181:
1679:
1285:
1021:
831:
695:
343:
1343:
630:
516:
1936:
1280:
1076:
775:
413:
123:
1906:
686:
684:(WSSA) (2014). "Common and Chemical Names of Herbicides Approved by the Weed Science Society of America".
389:
1858:
888:
547:
430:
397:
330:
47:
755:
733:
613:
1303:
901:
835:
463:
820:(1992). "Applications of nuclear analytical techniques in environmental research. Plenary lecture".
2002:
1916:
1881:
1622:
1275:
1069:
198:
71:
1181:
1876:
1333:
1242:
1161:
1049:
988:
715:
1381:
1787:
1767:
1762:
1664:
1252:
1141:
1777:
1453:
1391:
1366:
1156:
1041:
1033:
980:
968:
935:
917:
859:
851:
822:
707:
1838:
1737:
1025:
972:
925:
909:
843:
699:
319:
240:
81:
169:
1593:
1029:
897:
421:
650:"From Pioneering Invention to Sustained Innovation: The Story of Sulfonylurea Herbicides"
202:
127:
905:
839:
592:
571:
1815:
1782:
1729:
1270:
930:
883:
504:
393:
363:
884:"CRISPR technology is revolutionizing the improvement of tomato and other fruit crops"
614:"Weed Science Society of America - Herbicide Site of Action (SOA) Classification List"
1996:
1871:
1866:
1688:
1627:
1536:
1510:
1462:
1313:
1176:
817:
719:
417:
308:
116:
1053:
992:
478:
442:
1976:
1971:
1961:
1823:
1606:
1308:
1217:
1209:
1151:
1146:
1092:
955:
434:
149:
17:
1848:
1843:
1601:
1583:
1563:
1553:
1545:
1470:
1418:
1371:
1206:
1196:
1166:
1131:
34:
703:
1966:
1946:
1926:
1792:
1752:
1654:
1518:
1500:
1485:
1376:
1328:
1323:
1318:
1247:
1227:
1222:
1186:
1116:
913:
520:
277:
1037:
984:
976:
921:
855:
813:
711:
1956:
1931:
1911:
1747:
1669:
1649:
1568:
1495:
1490:
1475:
1356:
1351:
1136:
1096:
535:
455:
1061:
1045:
939:
863:
1921:
1772:
1757:
1742:
1720:
1706:
1659:
1641:
1578:
1573:
1480:
1438:
1423:
1361:
1237:
1191:
1171:
1121:
847:
496:
482:
US Geological Survey estimate of tribenuron methyl use in the USA to 2018
1951:
1941:
1833:
1558:
1262:
1232:
1108:
1104:
531:
298:
136:
1701:
1413:
1126:
362:
Except where otherwise noted, data are given for materials in their
1696:
1400:
477:
425:
104:
94:
433:
with 2-methylamino-4-methoxy-6-methyl-1,3,5-triazine to form the
1828:
1806:
1433:
1428:
539:
1065:
186:
500:
527:
mutants but not the controls, under tribenuron treatment.
882:
Wang, Tian; Zhang, Hongyan; Zhu, Hongliang (2019-06-15).
794:"Estimated Agricultural Use for tribenuron methyl, 2018"
225:
CC1=NC(=NC(=N1)OC)N(C)C(=O)NS(=O)(=O)C2=CC=CC=C2C(=O)OC
583:
581:
593:"Global HRAC MOA Classification Working Group Report"
495:
In a clay-water suspension, tribenuron has increased
1899:
1857:
1814:
1805:
1728:
1719:
1687:
1678:
1640:
1615:
1592:
1544:
1535:
1509:
1461:
1452:
1399:
1390:
1342:
1294:
1261:
1205:
1103:
631:"Herbicide Classification Master: March 11, 2020"
625:
623:
607:
605:
470:has placed it in group 2 (legacy HRAC Group B).
148:
80:
1077:
8:
1811:
1725:
1684:
1541:
1458:
1396:
1084:
1070:
1062:
201:
126:
26:
929:
168:
750:
748:
559:
222:
197:
565:
563:
117:
1030:10.1146/annurev-arplant-042817-040038
635:Herbicide Resistance Action Committee
589:Herbicide Resistance Action Committee
468:Herbicide Resistance Action Committee
402:Herbicide Resistance Action Committee
7:
139:
612:Scott Senseman (3 December 2020).
25:
523:and validated by survival of the
538:cultivars have been produced by
441:
258:
252:
33:
965:Crop Science Society of America
776:"DuPont Tribenuron Methyl 50SG"
682:Weed Science Society of America
570:Pesticide Properties Database.
460:acetolactate synthase inhibitor
366:(at 25 °C , 100 kPa).
1013:Annual Review of Plant Biology
657:Chemical Heritage NewsMagazine
574:. University of Hertfordshire.
270:
264:
246:
1:
51:Methyl 2-sulfamoyl]benzoate
2024:
832:Royal Society of Chemistry
704:10.1614/0043-1745-62.4.679
696:Cambridge University Press
412:In the 1970s, chemists at
404:'s classification scheme.
1816:Photosystem II inhibitors
1730:Photosystem II inhibitors
914:10.1038/s41438-019-0159-x
648:Bhardwaj, Gaurab (2007).
360:
293:White to off-white solid
233:
213:
64:
56:
46:
41:
32:
1689:Photosystem I inhibitors
977:10.2135/cropsci2004.1037
515:A tribenuron-resistance
2008:Sulfonylurea herbicides
325:2483 mg/L (20 °C)
792:US Geological Survey.
637:(HRAC). 11 March 2020.
591:(HRAC) (2 June 2020).
503:and even more so with
483:
462:. For the purposes of
390:sulfonylurea herbicide
889:Horticulture Research
756:US patent 4740234
734:US patent 4383113
548:conventional breeding
519:has been achieved in
481:
398:acetolactate synthase
396:is the inhibition of
848:10.1039/an9921700243
464:herbicide resistance
1917:aminocyclopyrachlor
1882:sulfometuron methyl
906:2019HorR....6...77W
840:1992Ana...117..243S
663:(1). Archived from
572:"Tribenuron-methyl"
320:Solubility in water
285: g·mol
29:
1877:metsulfuron-methyl
1546:Nitrophenyl ethers
484:
420:. Tribenuron (the
370:Infobox references
28:Tribenuron methyl
27:
1990:
1989:
1895:
1894:
1801:
1800:
1715:
1714:
1636:
1635:
1537:Protox inhibitors
1531:
1530:
1527:
1526:
1454:ACCase inhibitors
454:Tribenuron is an
424:) and its methyl
400:, group 2 of the
386:tribenuron-methyl
378:Chemical compound
376:
375:
182:CompTox Dashboard
106:Interactive image
18:Tribenuron-methyl
16:(Redirected from
2015:
1812:
1726:
1685:
1594:Pyrimidinediones
1542:
1459:
1397:
1344:Organophosphorus
1086:
1079:
1072:
1063:
1057:
997:
996:
950:
944:
943:
933:
879:
873:
871:
867:
810:
804:
803:
801:
800:
789:
783:
782:
780:
771:
765:
764:
763:
759:
752:
743:
742:
741:
737:
730:
724:
723:
698:(CUP): 679–687.
678:
672:
671:
669:
654:
645:
639:
638:
627:
618:
617:
609:
600:
599:
597:
585:
576:
575:
567:
499:with decreasing
491:Physicochemistry
466:management, the
458:that acts as an
445:
284:
272:
266:
260:
254:
248:
241:Chemical formula
206:
205:
190:
188:
172:
152:
141:
130:
119:
108:
84:
37:
30:
21:
2023:
2022:
2018:
2017:
2016:
2014:
2013:
2012:
1993:
1992:
1991:
1986:
1891:
1853:
1797:
1711:
1674:
1632:
1611:
1588:
1523:
1505:
1448:
1386:
1338:
1304:flurochloridone
1290:
1276:copper arsenate
1257:
1201:
1099:
1090:
1009:
1006:
1004:Further reading
1001:
1000:
952:
951:
947:
898:Nature Research
881:
880:
876:
869:
818:Steinnes, Eiliv
812:
811:
807:
798:
796:
791:
790:
786:
778:
774:DuPont (2004).
773:
772:
768:
761:
754:
753:
746:
739:
732:
731:
727:
680:
679:
675:
667:
652:
647:
646:
642:
629:
628:
621:
611:
610:
603:
595:
587:
586:
579:
569:
568:
561:
556:
513:
511:Resistant crops
493:
476:
452:
422:carboxylic acid
410:
384:in the form of
379:
372:
367:
352:
322:
282:
269:
263:
257:
251:
243:
229:
226:
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209:
191:
184:
175:
155:
142:
111:
98:
87:
74:
60:
52:
23:
22:
15:
12:
11:
5:
2021:
2019:
2011:
2010:
2005:
1995:
1994:
1988:
1987:
1985:
1984:
1979:
1974:
1969:
1964:
1959:
1954:
1949:
1944:
1939:
1934:
1929:
1924:
1919:
1914:
1909:
1903:
1901:
1897:
1896:
1893:
1892:
1890:
1889:
1884:
1879:
1874:
1869:
1863:
1861:
1859:ALS inhibitors
1855:
1854:
1852:
1851:
1846:
1841:
1836:
1831:
1826:
1820:
1818:
1809:
1803:
1802:
1799:
1798:
1796:
1795:
1790:
1785:
1783:terbuthylazine
1780:
1775:
1770:
1765:
1760:
1755:
1750:
1745:
1740:
1734:
1732:
1723:
1717:
1716:
1713:
1712:
1710:
1709:
1704:
1699:
1693:
1691:
1682:
1676:
1675:
1673:
1672:
1667:
1662:
1657:
1652:
1646:
1644:
1638:
1637:
1634:
1633:
1631:
1630:
1625:
1619:
1617:
1613:
1612:
1610:
1609:
1604:
1598:
1596:
1590:
1589:
1587:
1586:
1581:
1576:
1571:
1566:
1561:
1556:
1550:
1548:
1539:
1533:
1532:
1529:
1528:
1525:
1524:
1522:
1521:
1515:
1513:
1511:DIM herbicides
1507:
1506:
1504:
1503:
1498:
1493:
1488:
1483:
1478:
1473:
1467:
1465:
1463:FOP herbicides
1456:
1450:
1449:
1447:
1446:
1441:
1436:
1431:
1426:
1421:
1416:
1411:
1405:
1403:
1394:
1388:
1387:
1385:
1384:
1379:
1374:
1369:
1364:
1359:
1354:
1348:
1346:
1340:
1339:
1337:
1336:
1331:
1326:
1321:
1316:
1311:
1306:
1300:
1298:
1296:HPPD inhbitors
1292:
1291:
1289:
1288:
1283:
1278:
1273:
1271:cacodylic acid
1267:
1265:
1259:
1258:
1256:
1255:
1250:
1245:
1240:
1235:
1230:
1225:
1220:
1214:
1212:
1203:
1202:
1200:
1199:
1194:
1189:
1184:
1179:
1174:
1169:
1164:
1159:
1154:
1149:
1144:
1139:
1134:
1129:
1124:
1119:
1113:
1111:
1101:
1100:
1091:
1089:
1088:
1081:
1074:
1066:
1060:
1059:
1022:Annual Reviews
1005:
1002:
999:
998:
971:): 1037–1038.
945:
874:
834:(RSC): 243–9.
805:
784:
766:
744:
725:
673:
670:on 2006-11-18.
640:
619:
601:
577:
558:
557:
555:
552:
517:transformation
512:
509:
505:suspended load
492:
489:
475:
472:
451:
450:Mode of action
448:
447:
446:
409:
406:
394:mode of action
377:
374:
373:
368:
364:standard state
361:
358:
357:
354:
350:
340:
339:
336:
327:
326:
323:
318:
315:
314:
311:
305:
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301:
295:
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261:
255:
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194:
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154:
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145:
143:
135:
132:
131:
121:
113:
112:
110:
109:
101:
99:
92:
89:
88:
86:
85:
77:
75:
70:
67:
66:
62:
61:
58:
54:
53:
50:
44:
43:
39:
38:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2020:
2009:
2006:
2004:
2001:
2000:
1998:
1983:
1980:
1978:
1975:
1973:
1970:
1968:
1965:
1963:
1960:
1958:
1955:
1953:
1950:
1948:
1945:
1943:
1940:
1938:
1935:
1933:
1930:
1928:
1925:
1923:
1920:
1918:
1915:
1913:
1910:
1908:
1905:
1904:
1902:
1898:
1888:
1885:
1883:
1880:
1878:
1875:
1873:
1872:flazasulfuron
1870:
1868:
1867:chlorsulfuron
1865:
1864:
1862:
1860:
1856:
1850:
1847:
1845:
1842:
1840:
1837:
1835:
1832:
1830:
1827:
1825:
1822:
1821:
1819:
1817:
1813:
1810:
1808:
1804:
1794:
1791:
1789:
1786:
1784:
1781:
1779:
1776:
1774:
1771:
1769:
1766:
1764:
1761:
1759:
1756:
1754:
1751:
1749:
1746:
1744:
1741:
1739:
1736:
1735:
1733:
1731:
1727:
1724:
1722:
1718:
1708:
1705:
1703:
1700:
1698:
1695:
1694:
1692:
1690:
1686:
1683:
1681:
1677:
1671:
1668:
1666:
1663:
1661:
1658:
1656:
1653:
1651:
1648:
1647:
1645:
1643:
1639:
1629:
1628:sulfentrazone
1626:
1624:
1623:carfentrazone
1621:
1620:
1618:
1616:Triazolinones
1614:
1608:
1605:
1603:
1600:
1599:
1597:
1595:
1591:
1585:
1582:
1580:
1577:
1575:
1572:
1570:
1567:
1565:
1562:
1560:
1557:
1555:
1552:
1551:
1549:
1547:
1543:
1540:
1538:
1534:
1520:
1517:
1516:
1514:
1512:
1508:
1502:
1499:
1497:
1494:
1492:
1489:
1487:
1484:
1482:
1479:
1477:
1474:
1472:
1469:
1468:
1466:
1464:
1460:
1457:
1455:
1451:
1445:
1442:
1440:
1437:
1435:
1432:
1430:
1427:
1425:
1422:
1420:
1417:
1415:
1412:
1410:
1407:
1406:
1404:
1402:
1398:
1395:
1393:
1389:
1383:
1380:
1378:
1375:
1373:
1370:
1368:
1365:
1363:
1360:
1358:
1355:
1353:
1350:
1349:
1347:
1345:
1341:
1335:
1332:
1330:
1327:
1325:
1322:
1320:
1317:
1315:
1314:leptospermone
1312:
1310:
1307:
1305:
1302:
1301:
1299:
1297:
1293:
1287:
1284:
1282:
1279:
1277:
1274:
1272:
1269:
1268:
1266:
1264:
1260:
1254:
1251:
1249:
1246:
1244:
1241:
1239:
1236:
1234:
1231:
1229:
1226:
1224:
1221:
1219:
1216:
1215:
1213:
1211:
1208:
1204:
1198:
1195:
1193:
1190:
1188:
1185:
1183:
1180:
1178:
1177:pendimethalin
1175:
1173:
1170:
1168:
1165:
1163:
1160:
1158:
1155:
1153:
1150:
1148:
1145:
1143:
1140:
1138:
1135:
1133:
1130:
1128:
1125:
1123:
1120:
1118:
1115:
1114:
1112:
1110:
1106:
1102:
1098:
1094:
1087:
1082:
1080:
1075:
1073:
1068:
1067:
1064:
1058:Supplemental.
1055:
1051:
1047:
1043:
1039:
1035:
1031:
1027:
1023:
1019:
1015:
1014:
1008:
1007:
1003:
994:
990:
986:
982:
978:
974:
970:
966:
962:
958:
957:
949:
946:
941:
937:
932:
927:
923:
919:
915:
911:
907:
903:
899:
895:
891:
890:
885:
878:
875:
865:
861:
857:
853:
849:
845:
841:
837:
833:
829:
825:
824:
819:
815:
809:
806:
795:
788:
785:
777:
770:
767:
757:
751:
749:
745:
735:
729:
726:
721:
717:
713:
709:
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19:
1977:pyribenzoxim
1972:prosulfocarb
1962:metam sodium
1886:
1824:chlortoluron
1607:saflufenacil
1309:isoxaflutole
1218:aminopyralid
1182:pretilachlor
1152:dimethenamid
1147:diflufenican
1093:Pest control
1017:
1011:
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956:Crop Science
954:
948:
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474:Applications
453:
435:sulfonylurea
411:
385:
381:
380:
347:
332:
65:Identifiers
57:Other names
1849:tebuthiuron
1844:monolinuron
1602:butafenacil
1584:oxyfluorfen
1564:fluorodifen
1554:acifluorfen
1471:chlorazifop
1419:dichlorprop
1372:glufosinate
1334:sulcotrione
1243:pyrithiobac
1197:trifluralin
1167:metolachlor
1162:metazachlor
1132:benfluralin
1024:: 611–635.
823:The Analyst
814:Salbu, Brit
290:Appearance
234:Properties
124:100.100.313
82:101200-48-0
2003:Herbicides
1997:Categories
1967:metribuzin
1947:indaziflam
1927:bromoxynil
1887:tribenuron
1793:metamitron
1753:hexazinone
1680:Quaternary
1655:fluroxypyr
1519:sethoxydim
1501:quizalofop
1486:fenoxaprop
1382:piperophos
1377:glyphosate
1329:sethoxydim
1324:nitisinone
1319:mesotrione
1263:Arsenicals
1248:quinclorac
1228:clopyralid
1223:chloramben
1187:propachlor
1117:acetochlor
1097:herbicides
799:2023-01-13
554:References
521:watermelon
437:product.
382:Tribenuron
303:1.46 g/cm
278:Molar mass
170:D0493A985P
93:3D model (
72:CAS Number
48:IUPAC name
1957:methazole
1932:clomazone
1912:aclonifen
1788:terbutryn
1768:propazine
1763:prometryn
1748:cyanazine
1721:Triazines
1697:cyperquat
1670:triclopyr
1665:thiazopyr
1650:dithiopyr
1642:Pyridines
1569:fomesafen
1496:haloxyfop
1491:fluazifop
1476:cyhalofop
1357:bialaphos
1352:bensulide
1253:quinmerac
1142:diethatyl
1137:butachlor
1038:1543-5008
985:0011-183X
922:2052-7276
856:0003-2654
720:198130304
712:0043-1745
536:sunflower
456:herbicide
431:condensed
408:Chemistry
59:DPX L5300
1922:Bentazon
1778:simetryn
1773:simazine
1758:prometon
1743:atrazine
1707:paraquat
1660:imazapyr
1579:nitrofen
1574:lactofen
1481:diclofop
1439:mecoprop
1424:fenoprop
1367:fosamine
1362:ethephon
1238:picloram
1207:Aromatic
1192:propanil
1172:oryzalin
1157:flamprop
1122:alachlor
1109:anilines
1105:Anilides
1054:25489201
1046:29140727
993:85001003
940:31240102
497:sorption
1952:juglone
1942:dinoseb
1839:monuron
1834:linuron
1738:ametryn
1559:bifenox
1444:2,4,5-T
1392:Phenoxy
1233:dicamba
931:6570646
902:Bibcode
864:1580364
836:Bibcode
532:oilseed
344:Acidity
299:Density
137:PubChem
1900:Others
1702:diquat
1414:2,4-DB
1401:Auxins
1127:asulam
1052:
1044:
1036:
991:
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414:DuPont
392:. Its
283:395.39
218:SMILES
150:153909
42:Names
1982:Ziram
1807:Ureas
1409:2,4-D
1210:acids
1050:S2CID
1020:(1).
989:S2CID
969:Wiley
963:(3).
896:(1).
830:(3).
779:(PDF)
716:S2CID
694:(4).
668:(PDF)
653:(PDF)
596:(PDF)
534:type
426:ester
388:is a
356:4.65
338:0.38
95:JSmol
1937:DCBN
1907:3-AT
1829:DCMU
1434:MCPB
1429:MCPA
1286:MSMA
1281:DSMA
1042:PMID
1034:ISSN
981:ISSN
936:PMID
918:ISSN
872:248.
860:PMID
852:ISSN
708:ISSN
540:USDA
530:Two
331:log
313:142
161:UNII
1026:doi
973:doi
926:PMC
910:doi
844:doi
828:117
700:doi
546:by
544:ARS
525:als
187:EPA
140:CID
1999::
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1018:69
1016:.
987:.
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622:^
604:^
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507:.
501:pH
353:)
346:(p
256:17
250:15
1107:/
1085:e
1078:t
1071:v
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542:-
351:a
348:K
333:P
271:S
268:6
265:O
262:5
259:N
253:H
247:C
189:)
185:(
97:)
20:)
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