124:
100:
217:
193:
112:
311:
88:
422:
181:
31:
430:
267:
205:
229:
445:, both in 1989. In 1990, Dow introduced cyhalofop-P butyl for the control of weeds in rice. Fluazifop-P butyl still has significant use in the USA. 200,000 pounds (91,000 kg) were applied in 2018 — almost exclusively in soyabean. The "P" in the name of these materials refers to their use now as single
338:
filed patents on a new class of compound, the aryloxphenoxypropionates, which showed such selectivity and led to the commercialisation of diclofop. Then the
Japanese company Ishihara Sangyo Kaisha (ISK) found improved biological activity in an analogue, chlorazifop, which replaced the aryloxy portion
274:
The use of herbicides in US agriculture is mapped by the US Geological Survey. As of 2019, 2,4-D was the most used of the auxins. 45,000,000 pounds (20,000,000 kg) were sprayed that year, compared to 2,000,000 pounds (910,000 kg) of the next most heavily applied, MCPA. The other auxin now
693:
299:
companies were working to develop new herbicides to be complementary to the auxins. The aim was to find materials which would selectively control grass weeds in broad-leaf crops such as
437:
Salts and esters of this class of herbicide are active owing to their ability to metabolise to the corresponding parent acid. For example, fenoxaprop-P ethyl was introduced by
1325:
251:
for 2,4-D and MCPA respectively: that is, they are converted in plants to these active ingredients. All the auxin herbicides retain activity when applied as
1034:
343:
ring containing the same two chlorine substituents. This area of research became very competitive and within three weeks of one another in 1977 ISK,
138:
were in widespread use in agriculture by the middle of the 1950s. The best known phenoxy herbicides are (4-chloro-2-methylphenoxy)acetic acid (
578:
630:
1113:
192:
568:
414:
in the target plant leads to the parent acid which is responsible for the herbicidal action. It is a coincidence that it is the (2R)
2011:
1473:
929:
613:
147:
672:
749:
123:
99:
753:
651:
216:
1438:
143:
69:(IAA). When sprayed on broad-leaf plants they induce rapid, uncontrolled growth ("growing to death"). Thus when applied to
111:
348:
442:
410:
species, making them ineffective on broad-leaf weeds and other organisms including mammals. When applied as an ester,
595:
1709:
1315:
372:
174:
centre in these molecules and biological activity is found only in the (2R)-isomer (illustrated for dichlorprop).
1373:
567:
Wendeborn, S.; Smits, H. (31 December 2012). "Synthetic Auxins". In Erick M. Carreira; Hisashi
Yamamoto (eds.).
545:
367:
Fusilade while Dow marketed haloxyfop as its methyl ester. All these compounds have an additional oxygen-linked
1966:
1310:
1106:
865:"Graminicide insensitivity correlates with herbicide-binding co-operativity on acetyl-CoA carboxylase isoforms"
355:) group in place of one of the chlorine atoms in the pyridine. Subsequently, ISK and ICI cross-licensed their
418:
which binds to plant ACCase, just as that isomer is responsible for the activity of dichlorprop as an auxin.
912:
463:
1936:
532:
387:
775:"Fluazifop, a grass-selective herbicide which inhibits acetyl-CoA carboxylase in sensitive plant species"
1888:
356:
1333:
471:
284:
2032:
1946:
1911:
1652:
1305:
1099:
391:
180:
1211:
530:
Troyer, James (2001). "In the beginning: the multiple discovery of the first hormone herbicides".
248:
87:
1906:
1363:
1272:
1191:
1077:
845:
549:
438:
383:)COOH group and as a class are called "fops", referring to their common fenoxy-phenoxy feature.
54:
1411:
1817:
1797:
1792:
1694:
1282:
1171:
1807:
1396:
1186:
925:
894:
863:
Price, Lindsey J.; Herbert, Derek; Moss, Stephen R.; Cole, David J.; Harwood, John L. (2003).
804:
609:
574:
512:
475:
151:
66:
1868:
1767:
1067:
917:
884:
876:
835:
794:
786:
721:
601:
541:
504:
70:
824:"Mode of Action of Herbicides Affecting Acetyl-CoA Carboxylase and Fatty Acid Biosynthesis"
1623:
495:
Grossmann, K. (2010). "Auxin herbicides: current status of mechanism and mode of action".
310:
155:
81:(corn), they selectively kill broad-leaf weeds, leaving the crops relatively unaffected.
1012:
990:
968:
946:
1845:
1812:
1759:
1300:
889:
864:
799:
774:
478:
concentrations at the application site, while the wild type responds with an increase.
421:
351:(ICI) all filed patents covering another group of analogues, with a trifluoromethyl (CF
34:
Phenoxyacetic acid, the partial structure which many of these herbicides have in common
605:
2026:
1901:
1896:
1718:
1657:
1566:
1540:
1492:
1343:
1206:
1081:
344:
204:
849:
553:
394:
to that of the auxins. Their selectivity for grasses arises because they target the
45:") are two families of chemicals that have been developed as commercially important
2006:
2001:
1991:
1853:
1636:
1338:
1247:
1239:
1181:
1176:
1122:
415:
296:
280:
154:
of each of these three compounds, with an extra methyl group attached next to the
30:
283:
rather than a phenoxyacetic acid whose use has grown rapidly since 2016 as crops
1878:
1873:
1631:
1613:
1593:
1583:
1575:
1500:
1448:
1401:
1236:
1226:
1196:
1161:
446:
429:
163:
50:
921:
1996:
1976:
1956:
1916:
1822:
1782:
1684:
1548:
1530:
1515:
1406:
1358:
1353:
1348:
1277:
1257:
1252:
1216:
1146:
411:
364:
335:
266:
1986:
1961:
1941:
1777:
1699:
1679:
1598:
1525:
1520:
1505:
1386:
1381:
1166:
1126:
1072:
1055:
360:
279:, where the 2019 figure was 30,000,000 pounds (14,000,000 kg). It is a
228:
135:
46:
17:
1091:
898:
516:
65:
The first group to be discovered act by mimicking the auxin growth hormone
840:
823:
808:
1951:
1802:
1787:
1772:
1750:
1736:
1689:
1671:
1608:
1603:
1510:
1468:
1453:
1391:
1267:
1221:
1201:
1151:
368:
340:
239:
Other members of this group include 4-(2,4-dichlorophenoxy)butyric acid (
167:
159:
914:
Bioactive
Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals
1981:
1971:
1863:
1588:
1292:
1262:
1138:
1134:
880:
729:
Proceeding of the First
International Weed Control Congress , Melbourne
403:
395:
304:
276:
790:
1731:
1443:
1156:
399:
376:
300:
256:
240:
171:
508:
1726:
1054:
Radchenko, M.; Ponomareva, I.; Pozynych, I.; Morderer, Ye. (2021).
1430:
428:
420:
309:
265:
252:
78:
74:
29:
694:"EPA approves Monsanto's less-volatile form of dicamba herbicide"
433:
US Geological Survey estimate of fluazifop use in the USA to 2018
1858:
1836:
1463:
1458:
773:
Walker, K. A.; Ridley, S. M.; Lewis, T.; Harwood, J. L. (1988).
244:
139:
1095:
270:
US Geological Survey estimate of 2,4-D use in the USA to 2019
546:
10.1614/0043-1745(2001)049[0290:ITBTMD]2.0.CO;2
259:
since these are also capable of producing the parent acid
600:. Advances in Agronomy. Vol. 54. pp. 93–94.
1929:
1887:
1844:
1835:
1758:
1749:
1717:
1708:
1670:
1645:
1622:
1574:
1565:
1539:
1491:
1482:
1429:
1420:
1372:
1324:
1291:
1235:
1133:
386:This group of herbicides acts by inhibiting plant
1035:"Estimated Agricultural Use for Fluazifop, 2018"
243:) and 4-(4-chloro-2-methylphenoxy)butyric acid (
673:"Estimated Agricultural Use for Dicamba, 2019"
1107:
1056:"Stress and use of herbicides in field crops"
170:. The addition of the methyl group creates a
8:
631:"Estimated Agricultural Use for 2,4-D, 2019"
287:to be resistant to it have been cultivated.
652:"Estimated Agricultural Use for MCPA, 2018"
1841:
1755:
1714:
1571:
1488:
1426:
1114:
1100:
1092:
1071:
888:
839:
798:
715:
713:
594:Dekker, Jack; Duke, Stephen O. (1995).
487:
275:used in comparable amounts to 2,4-D is
176:
83:
1483:
158:, were subsequently commercialised as
722:"Designing more efficient herbicides"
363:as its butyl ester in 1981 under the
7:
750:"Aryloxyphenoxypropionic herbicides"
1033:US Geological Survey (2021-10-12).
671:US Geological Survey (2021-10-12).
650:US Geological Survey (2021-10-12).
629:US Geological Survey (2021-10-12).
53:. They share the part structure of
822:Lichtenthaler, Hartmut K. (1990).
470:s mechanism of fenoxaprop-P-ethyl
25:
1060:Agricultural Science and Practice
461:, 1999, 2009, and 2013 find that
390:(ACCase), a completely different
148:2,4,5-trichlorophenoxyacetic acid
828:Zeitschrift für Naturforschung C
227:
215:
203:
191:
179:
122:
110:
98:
86:
1011:Pesticide Properties Database.
989:Pesticide Properties Database.
967:Pesticide Properties Database.
945:Pesticide Properties Database.
597:Herbicide-Resistant Field Crops
144:2,4-dichlorophenoxyacetic acid
1:
1015:. University of Hertfordshire
993:. University of Hertfordshire
971:. University of Hertfordshire
949:. University of Hertfordshire
606:10.1016/S0065-2113(08)60898-6
349:Imperial Chemical Industries
443:Nissan Chemical Corporation
2049:
922:10.1002/9783527693931.ch24
692:Gray, Bryce (2016-11-09).
441:and quizalofop-P ethyl by
314:Cyhalofop: X=CH, R=CN, R=F
134:Introduced in 1946, these
1846:Photosystem II inhibitors
1760:Photosystem II inhibitors
1719:Photosystem I inhibitors
318:Chlorazifop: X=N, R=R=Cl
1073:10.15407/agrisp8.03.050
698:St. Louis Post-Dispatch
570:Comprehensive Chirality
497:Pest Management Science
464:Alopecurus myocuroides
434:
426:
388:acetyl-CoA carboxylase
331:
316:Diclofop: X=CH, R=R=Cl
271:
35:
841:10.1515/znc-1990-0538
432:
424:
357:intellectual property
313:
269:
33:
969:"Quizalofop-P-ethyl"
947:"Fenoxaprop-P-ethyl"
916:. pp. 325–337.
402:present only in the
379:ring with its OCH(CH
326:Haloxyfop: X=N, R=CF
320:Fluazifop: X=N, R=CF
285:genetically modified
1947:aminocyclopyrachlor
1912:sulfometuron methyl
1013:"Fluazifop-P-butyl"
869:Biochemical Journal
779:Biochemical Journal
392:mechanism of action
359:and first marketed
339:of diclofop with a
1907:metsulfuron-methyl
1576:Nitrophenyl ethers
881:10.1042/bj20030665
720:Evans, D. (1992).
439:Bayer Crop Science
435:
427:
425:Fenoxaprop-P-ethyl
332:
272:
55:phenoxyacetic acid
39:Phenoxy herbicides
36:
27:Class of herbicide
2020:
2019:
1925:
1924:
1831:
1830:
1745:
1744:
1666:
1665:
1567:Protox inhibitors
1561:
1560:
1557:
1556:
1484:ACCase inhibitors
991:"Cyhalofop-butyl"
791:10.1042/bj2540307
580:978-0-08-095168-3
476:hydrogen peroxide
291:ACCase inhibitors
67:indoleacetic acid
49:, widely used in
16:(Redirected from
2040:
1842:
1756:
1715:
1624:Pyrimidinediones
1572:
1489:
1427:
1374:Organophosphorus
1116:
1109:
1102:
1093:
1086:
1085:
1075:
1051:
1045:
1044:
1042:
1041:
1030:
1024:
1023:
1021:
1020:
1008:
1002:
1001:
999:
998:
986:
980:
979:
977:
976:
964:
958:
957:
955:
954:
942:
936:
935:
909:
903:
902:
892:
860:
854:
853:
843:
819:
813:
812:
802:
770:
764:
763:
761:
760:
746:
740:
739:
737:
736:
731:. pp. 37–38
726:
717:
708:
707:
705:
704:
689:
683:
682:
680:
679:
668:
662:
661:
659:
658:
647:
641:
640:
638:
637:
626:
620:
619:
591:
585:
584:
564:
558:
557:
527:
521:
520:
503:(2): 2033–2043.
492:
469:
231:
219:
207:
198:(2R)-Dichlorprop
195:
183:
126:
114:
102:
90:
71:monocotyledonous
21:
2048:
2047:
2043:
2042:
2041:
2039:
2038:
2037:
2023:
2022:
2021:
2016:
1921:
1883:
1827:
1741:
1704:
1662:
1641:
1618:
1553:
1535:
1478:
1416:
1368:
1334:flurochloridone
1320:
1306:copper arsenate
1287:
1231:
1129:
1120:
1090:
1089:
1053:
1052:
1048:
1039:
1037:
1032:
1031:
1027:
1018:
1016:
1010:
1009:
1005:
996:
994:
988:
987:
983:
974:
972:
966:
965:
961:
952:
950:
944:
943:
939:
932:
911:
910:
906:
862:
861:
857:
821:
820:
816:
772:
771:
767:
758:
756:
748:
747:
743:
734:
732:
724:
719:
718:
711:
702:
700:
691:
690:
686:
677:
675:
670:
669:
665:
656:
654:
649:
648:
644:
635:
633:
628:
627:
623:
616:
593:
592:
588:
581:
566:
565:
561:
529:
528:
524:
509:10.1002/ps.1860
494:
493:
489:
484:
467:
455:
382:
354:
329:
325:
323:
319:
317:
315:
293:
247:) which act as
235:
232:
223:
220:
211:
208:
199:
196:
187:
184:
156:carboxylic acid
130:
127:
118:
115:
106:
103:
94:
91:
63:
28:
23:
22:
15:
12:
11:
5:
2046:
2044:
2036:
2035:
2025:
2024:
2018:
2017:
2015:
2014:
2009:
2004:
1999:
1994:
1989:
1984:
1979:
1974:
1969:
1964:
1959:
1954:
1949:
1944:
1939:
1933:
1931:
1927:
1926:
1923:
1922:
1920:
1919:
1914:
1909:
1904:
1899:
1893:
1891:
1889:ALS inhibitors
1885:
1884:
1882:
1881:
1876:
1871:
1866:
1861:
1856:
1850:
1848:
1839:
1833:
1832:
1829:
1828:
1826:
1825:
1820:
1815:
1813:terbuthylazine
1810:
1805:
1800:
1795:
1790:
1785:
1780:
1775:
1770:
1764:
1762:
1753:
1747:
1746:
1743:
1742:
1740:
1739:
1734:
1729:
1723:
1721:
1712:
1706:
1705:
1703:
1702:
1697:
1692:
1687:
1682:
1676:
1674:
1668:
1667:
1664:
1663:
1661:
1660:
1655:
1649:
1647:
1643:
1642:
1640:
1639:
1634:
1628:
1626:
1620:
1619:
1617:
1616:
1611:
1606:
1601:
1596:
1591:
1586:
1580:
1578:
1569:
1563:
1562:
1559:
1558:
1555:
1554:
1552:
1551:
1545:
1543:
1541:DIM herbicides
1537:
1536:
1534:
1533:
1528:
1523:
1518:
1513:
1508:
1503:
1497:
1495:
1493:FOP herbicides
1486:
1480:
1479:
1477:
1476:
1471:
1466:
1461:
1456:
1451:
1446:
1441:
1435:
1433:
1424:
1418:
1417:
1415:
1414:
1409:
1404:
1399:
1394:
1389:
1384:
1378:
1376:
1370:
1369:
1367:
1366:
1361:
1356:
1351:
1346:
1341:
1336:
1330:
1328:
1326:HPPD inhbitors
1322:
1321:
1319:
1318:
1313:
1308:
1303:
1301:cacodylic acid
1297:
1295:
1289:
1288:
1286:
1285:
1280:
1275:
1270:
1265:
1260:
1255:
1250:
1244:
1242:
1233:
1232:
1230:
1229:
1224:
1219:
1214:
1209:
1204:
1199:
1194:
1189:
1184:
1179:
1174:
1169:
1164:
1159:
1154:
1149:
1143:
1141:
1131:
1130:
1121:
1119:
1118:
1111:
1104:
1096:
1088:
1087:
1046:
1025:
1003:
981:
959:
937:
930:
904:
875:(2): 415–423.
855:
834:(5): 521–528.
814:
785:(1): 307–310.
765:
741:
709:
684:
663:
642:
621:
614:
586:
579:
559:
540:(2): 290–297.
522:
486:
485:
483:
480:
454:
451:
380:
352:
327:
321:
295:In the 1970s,
292:
289:
237:
236:
233:
226:
224:
221:
214:
212:
209:
202:
200:
197:
190:
188:
185:
178:
132:
131:
128:
121:
119:
116:
109:
107:
104:
97:
95:
92:
85:
73:crops such as
62:
59:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2045:
2034:
2031:
2030:
2028:
2013:
2010:
2008:
2005:
2003:
2000:
1998:
1995:
1993:
1990:
1988:
1985:
1983:
1980:
1978:
1975:
1973:
1970:
1968:
1965:
1963:
1960:
1958:
1955:
1953:
1950:
1948:
1945:
1943:
1940:
1938:
1935:
1934:
1932:
1928:
1918:
1915:
1913:
1910:
1908:
1905:
1903:
1902:flazasulfuron
1900:
1898:
1897:chlorsulfuron
1895:
1894:
1892:
1890:
1886:
1880:
1877:
1875:
1872:
1870:
1867:
1865:
1862:
1860:
1857:
1855:
1852:
1851:
1849:
1847:
1843:
1840:
1838:
1834:
1824:
1821:
1819:
1816:
1814:
1811:
1809:
1806:
1804:
1801:
1799:
1796:
1794:
1791:
1789:
1786:
1784:
1781:
1779:
1776:
1774:
1771:
1769:
1766:
1765:
1763:
1761:
1757:
1754:
1752:
1748:
1738:
1735:
1733:
1730:
1728:
1725:
1724:
1722:
1720:
1716:
1713:
1711:
1707:
1701:
1698:
1696:
1693:
1691:
1688:
1686:
1683:
1681:
1678:
1677:
1675:
1673:
1669:
1659:
1658:sulfentrazone
1656:
1654:
1653:carfentrazone
1651:
1650:
1648:
1646:Triazolinones
1644:
1638:
1635:
1633:
1630:
1629:
1627:
1625:
1621:
1615:
1612:
1610:
1607:
1605:
1602:
1600:
1597:
1595:
1592:
1590:
1587:
1585:
1582:
1581:
1579:
1577:
1573:
1570:
1568:
1564:
1550:
1547:
1546:
1544:
1542:
1538:
1532:
1529:
1527:
1524:
1522:
1519:
1517:
1514:
1512:
1509:
1507:
1504:
1502:
1499:
1498:
1496:
1494:
1490:
1487:
1485:
1481:
1475:
1472:
1470:
1467:
1465:
1462:
1460:
1457:
1455:
1452:
1450:
1447:
1445:
1442:
1440:
1437:
1436:
1434:
1432:
1428:
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373:para position
371:group in the
370:
366:
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350:
346:
345:Dow Chemicals
342:
337:
312:
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249:propesticides
246:
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68:
60:
58:
56:
52:
48:
44:
40:
32:
19:
2007:pyribenzoxim
2002:prosulfocarb
1992:metam sodium
1854:chlortoluron
1637:saflufenacil
1421:
1339:isoxaflutole
1248:aminopyralid
1212:pretilachlor
1182:dimethenamid
1177:diflufenican
1123:Pest control
1066:(3): 50–70.
1063:
1059:
1049:
1038:. Retrieved
1028:
1017:. Retrieved
1006:
995:. Retrieved
984:
973:. Retrieved
962:
951:. Retrieved
940:
913:
907:
872:
868:
858:
831:
827:
817:
782:
778:
768:
757:. Retrieved
744:
733:. Retrieved
728:
701:. Retrieved
697:
687:
676:. Retrieved
666:
655:. Retrieved
645:
634:. Retrieved
624:
596:
589:
569:
562:
537:
533:Weed Science
531:
525:
500:
496:
490:
462:
458:
456:
436:
416:stereoisomer
407:
385:
333:
297:agrochemical
294:
281:benzoic acid
273:
260:
238:
146:(2,4-D) and
133:
64:
42:
38:
37:
18:Phenoxy acid
1879:tebuthiuron
1874:monolinuron
1632:butafenacil
1614:oxyfluorfen
1594:fluorodifen
1584:acifluorfen
1501:chlorazifop
1449:dichlorprop
1402:glufosinate
1364:sulcotrione
1273:pyrithiobac
1227:trifluralin
1197:metolachlor
1192:metazachlor
1162:benfluralin
447:enantiomers
164:dichlorprop
150:(2,4,5-T).
51:agriculture
2033:Herbicides
1997:metribuzin
1977:indaziflam
1957:bromoxynil
1917:tribenuron
1823:metamitron
1783:hexazinone
1710:Quaternary
1685:fluroxypyr
1549:sethoxydim
1531:quizalofop
1516:fenoxaprop
1412:piperophos
1407:glyphosate
1359:sethoxydim
1354:nitisinone
1349:mesotrione
1293:Arsenicals
1278:quinclorac
1258:clopyralid
1253:chloramben
1217:propachlor
1147:acetochlor
1127:herbicides
1040:2021-12-27
1019:2021-03-02
997:2022-10-06
975:2021-03-02
953:2021-03-02
759:2022-10-06
735:2021-02-27
703:2021-12-27
678:2021-12-27
657:2021-12-27
636:2021-12-27
573:. Newnes.
482:References
472:resistance
453:Resistance
412:metabolism
365:brand name
336:Hoechst AG
136:herbicides
47:herbicides
1987:methazole
1962:clomazone
1942:aclonifen
1818:terbutryn
1798:propazine
1793:prometryn
1778:cyanazine
1751:Triazines
1727:cyperquat
1700:triclopyr
1695:thiazopyr
1680:dithiopyr
1672:Pyridines
1599:fomesafen
1526:haloxyfop
1521:fluazifop
1506:cyhalofop
1387:bialaphos
1382:bensulide
1283:quinmerac
1172:diethatyl
1167:butachlor
1082:246978319
361:fluazifop
334:In 1973,
152:Analogues
43:phenoxies
2027:Category
1952:Bentazon
1808:simetryn
1803:simazine
1788:prometon
1773:atrazine
1737:paraquat
1690:imazapyr
1609:nitrofen
1604:lactofen
1511:diclofop
1469:mecoprop
1454:fenoprop
1397:fosamine
1392:ethephon
1268:picloram
1237:Aromatic
1222:propanil
1202:oryzalin
1187:flamprop
1152:alachlor
1139:anilines
1135:Anilides
899:12859251
850:27124700
554:85637273
517:19823992
474:reduces
457:Cummins
404:plastids
369:aromatic
341:pyridine
210:Fenoprop
186:Mecoprop
168:fenoprop
160:mecoprop
1982:juglone
1972:dinoseb
1869:monuron
1864:linuron
1768:ametryn
1589:bifenox
1474:2,4,5-T
1422:Phenoxy
1263:dicamba
890:1223688
809:2902848
800:1135074
398:of the
396:isoform
375:of the
330:, R=Cl
305:soybean
277:dicamba
261:in situ
129:2,4,5-T
1930:Others
1732:diquat
1444:2,4-DB
1431:Auxins
1157:asulam
1080:
928:
897:
887:
848:
807:
797:
612:
577:
552:
515:
459:et al.
400:enzyme
377:phenyl
301:cotton
257:esters
241:2,4-DB
222:2,4-DB
172:chiral
61:Auxins
2012:Ziram
1837:Ureas
1439:2,4-D
1240:acids
1078:S2CID
846:S2CID
725:(PDF)
550:S2CID
468:'
408:these
324:, R=H
253:salts
117:2,4-D
79:maize
75:wheat
41:(or "
1967:DCBN
1937:3-AT
1859:DCMU
1464:MCPB
1459:MCPA
1316:MSMA
1311:DSMA
926:ISBN
895:PMID
805:PMID
754:BCPC
610:ISBN
575:ISBN
513:PMID
347:and
303:and
255:and
245:MCPB
234:MCPB
166:and
140:MCPA
105:MCPA
1068:doi
918:doi
885:PMC
877:doi
873:375
836:doi
795:PMC
787:doi
783:254
602:doi
542:doi
505:doi
406:of
142:),
93:IAA
77:or
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