850:
842:
301:
206:
646:
43:
810:
34:
545:(IAA), the naturally occurring auxin, was used at high concentrations, it could stop plant growth. In 1940, he published his finding that IAA killed broadleaf plants within a cereal field. Templeman and the ICI group were searching for compounds with similar or greater selective activity than IAA or
696:
Its toxicity and biodegradation are topics of current research. One formulation is described by its manufacturer as "designed for specific markets that require the safest possible phenoxy product, primarily for use in the
Pacific Northwest". Though not extremely toxic, it has been determined that
774:
of MCPA degradation. It has been estimated that a total of 15000 tons of MCP were produced in 1989 in the EU. MCP is considered very toxic to aquatic organisms. However, the concentration of MCPA and MCP detected in water and soil are lower than the predicted no-effect levels of all environmental
613:
to join the ICI effort. The first publications about this group of herbicides were by other workers who were not the original inventors: the precise sequence of discovery events has been discussed. MCPA was first reported in the open scientific literature by Slade, Templeman and Sexton in 1945.
833:. Recent studies have demonstrated that biological degradation of MCPA is enzymatically catalyzed by an α-ketoglutarate-dependent dioxygenase encoded by the tfdA gene of soil microorganisms. Soil indigenous bacteria that carry the tfdA gene could use MCPA as the sole source of carbon.
765:
Wide usage of MCPA as an herbicide raises concern of environmental risks, so considerable research has been done in recent decades to evaluate the environmental risk of MCPA. MCPA can be moderately toxic to mammal and aquatic organisms, and relatively less toxic to birds. MCP
605:. All four groups were subject to wartime secrecy laws and did not follow the usual procedures of publication and patent disclosure, although ICI did file an application relating to both MCPA and 2,4-D on 7 April 1941 in the UK. In December 1942, following a meeting at the
721:
Agritox, Agroxone, Chiptox, Chwastox, Cornox, Methoxone, Rhonox, Spurge Power, Tigrex, Verdone Extra (UK), Weed-Rhap, Weed'n'Feed, Weed-B-Gone, Zero Bindii & Clover Weeder (Aus), Jolt (Aus), BIN-DIE (Aus), Maatilan MCPA, K-MCPA, Hedonal, Basagran (Finland), and
731:
Since MCPA is extensively used in the USA, the extensively dispersed MCPA and its biological and photochemical metabolites might be deemable as environmentally hazardous. However, current studies show that there is no resistance of MCPA to degrade in soil.
614:
ICI's decision to commercialize MCPA (rather than 2,4-D, for example) was influenced by the fact that ICI had access to 2-methyl-4-chlorophenol and following extensive field trials the material was first made available to UK farmers in 1946, as a 1% dust.
861:, •OH. The hydroxyl radical adds on the ring, followed by radical transfer to the ether carbon. With oxygen present, the addition of the hydroxyl radical leads the cleavage of the ether link, yielding MCP. The other scheme is MCPA oxidation by positive
748:
to leaves and stems. The MCPA residue left in soil typically has a half-life of 24 days. However, the degradation rate depends on environmental conditions, such as temperature and soil moisture. MCPA is rather mobile in soil, and not strongly
1054:
W.G. Templeman; W.A. Sexton (1946). "The
Differential Effect of Synthetic Plant Growth Substances upon Plant Species. I. Seed Germination and Early Growth Responses to α-Naphthylacetic Acid and Compounds of General Formula arylOCHCOO".
790:. In the general pH range of aqueous environments, the MCPA-metal complex has higher solubility than metal ions. MCPA may be environmentally hazardous by affecting the mobility and bio-availability of heavy metals such as
894:
Gimeno, Olga; Plucinski, Pawel; Kolaczkowski, Stan T.; Rivas, Francisco J.; Alvarez, Pedro M. (2003). "Removal of the
Herbicide MCPA by Commercial Activated Carbons: Equilibrium, Kinetics, and Reversibility".
1215:
J. Kobylecka; B. Ptaszynski; R. Rogaczewski; A. Turek (2003). "Phenoxyalkanoic acid complexes. Part I. Complexes of lead(II), cadmium(II) and copper(II) with 4-chloro-2-methylphenoxyacetic acid (MCPA)".
1582:
Nielsen, Morten S.; Bælum, Jacob; Jensen, Malene B.; Jacobsen, Carsten S. (2011-05-01). "Mineralization of the herbicide MCPA in urban soils is linked to presence and growth of class III tfdA genes".
1432:
Bala, Tanushree; Prasad, B. L. V.; Sastry, Murali; Kahaly, Mousumi
Upadhyay; Waghmare, Umesh V. (2007-07-19). "Interaction of different metal ions with carboxylic acid group: a quantitative study".
1286:
Prasad, Attaluri R.; Ramalingam, Thallapalli; Rao, Adari B.; Diwan, Prakash V.; Sattur, Pralhad B. (1989). "Synthesis and biological evaluation of 3-aryloxyalkyl-6-aryl-7H-s-triazolothiadiazines".
689:, whose data show consistent use from 1992, with a small recent decline in the ten years to 2017, the latest date for which figures are available. The compound is now used almost exclusively in
989:
Templeman, W. G.; Marmoy, C. J. (November 1940). "The effect upon the growth of plants of watering with solutions of plant-growth substances and of seed dressings containing these materials".
709:
group allows the formation of conjugated complexes with metals (see above). The acid functionality makes MCPA a versatile synthetic intermediate for more complex derivatives.
606:
857:
MCPA also could be photochemically degraded. Two scheme pathways can be proposed for the formation of the main intermediate, MCP. One scheme is MCPA oxidation by
1870:
937:
581:
By the end of 1941 it was clear to the
Templeman group that MCPA was one of the most active compounds tested but other auxin herbicides including
2189:
1344:
Helweg, A. (1987). "Degradation and adsorption of 14C-MCPA in soil—influence of concentration, temperature and moisture content on degradation".
1748:
697:
MCPA can form complexes with metal ions and thereby increase their bioavailability, and there is also work being done to utilize this ability.
1900:
1862:
1809:
1728:
541:
on plant growth looking specifically for a way to kill weeds without harming crops such as wheat and oats. William
Templeman found that when
1153:
597:
in the UK; Franklin D. Jones and associates at the
American Chemical Paint Company; and Ezra Kraus, John W. Mitchell, and associates at the
1948:
350:
2354:
2334:
2329:
2231:
1819:
1708:
1251:
R. Kruszynski; T.J. Bartczak; B. Ptaszynski; A. Turek (2002). "A Novel Lead- bis (4-Chloro-2-Methylphenoxy)- Acetate
Polymeric Complex".
2344:
1933:
1723:
2405:
2304:
874:
123:
602:
593:. Four groups worked independently in the United Kingdom and the United States: the ICI team; Philip S. Nutman and associates at
1525:
Bælum, Jacob; Nicolaisen, Mette H.; Holben, William E.; Strobel, Bjarne W.; Sørensen, Jan; Jacobsen, Carsten S. (2008-03-20).
817:
The MCPA can be degraded biologically in soils by plants and microorganisms. The major metabolite of MCPA degradation is MCP (
1650:
637:
of the plant. Uncontrolled, unsustainable growth ensues, causing stem curl-over, leaf withering, and eventual plant death.
1197:
740:
MCPA herbicide is usually sprayed to the soil surface and plant leaves in its water solution, sometimes with additional
1117:
Slade, R.E.; Templeman, W.G.; Sexton, W.A. (1945). "Differential effects of plant growth substances on plant species".
2548:
2010:
315:
20:
818:
767:
487:
686:
1103:
1975:
1038:
531:
258:
201:
1527:"Direct analysis of tfdA gene expression by indigenous bacteria in phenoxy acid amended agricultural soil"
653:
MCPA is used as an herbicide, generally as its salt or esterified forms. Used thus, it controls broadleaf
2579:
279:
163:
2246:
2020:
1852:
1488:"Photocatalytic transformation of 4-chloro-2-methylphenoxyacetic acid (MCPA) on several kinds of TiO2"
1910:
678:
798:. The acid functionality makes MCPA a versatile synthetic intermediate for more complex derivatives
2503:
1847:
1643:
830:
546:
296:
1090:
Troyer, James (2001). "In the beginning: the multiple discovery of the first hormone herbicides".
2584:
2473:
1030:
2574:
2569:
2425:
598:
558:
1021:
Allen, H.P.; et al. (1978). "Chapter 5: Selective herbicides". In
Peacock, F.C. (ed.).
1591:
1538:
1441:
1353:
1225:
877:. With the presence of oxygen, the positive holes h+ oxidation finally yields MCP as well.
849:
783:
542:
267:
55:
954:
Grossmann, K. (2010). "Auxin herbicides: current status of mechanism and mode of action".
629:, which results in uncontrolled growth and eventually death in susceptible plants, mainly
183:
8:
2483:
2448:
1842:
1636:
841:
754:
594:
89:
1621:
1595:
1542:
1445:
1407:
1379:
1357:
1317:
1229:
300:
205:
143:
99:
2443:
1365:
1268:
1134:
1023:
1002:
931:
590:
472:
1237:
829:. Another pathway could be the hydroxylation of the methyl group, yielding cloxyfonac
1958:
1564:
1556:
1507:
1487:
1465:
1457:
1299:
1072:
1034:
971:
610:
554:
534:
507:
466:
1272:
1138:
1599:
1546:
1499:
1449:
1361:
1295:
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1233:
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1099:
1064:
998:
963:
904:
858:
574:
446:
373:
1603:
2160:
1503:
1486:
Zertal, A.; Molnár-Gábor, D.; Malouki, M.A.; Sehili, T.; Boule, P. (2004-05-01).
779:
706:
247:
1264:
2382:
2349:
2296:
1837:
1250:
1214:
866:
481:
1967:
705:
Because it is inexpensive, MCPA is used in various chemical applications. Its
645:
549:
in inhibiting the growth of weeds while not adversely affecting the growth of
19:
This article is about the herbicide. For the toxin found in lychee seeds, see
2563:
2438:
2433:
2255:
2194:
2103:
2077:
2029:
1880:
1743:
1560:
1511:
1461:
1173:
862:
682:
677:
are tolerant at moderate application levels. It is currently classified as a
623:
553:
crops. They synthesized MCPA from the corresponding phenol by exposing it to
435:
194:
770:
is the intermediate in the synthesis of phenoxy herbicides, and is also the
2543:
2538:
2528:
2390:
2173:
1875:
1784:
1776:
1718:
1713:
1671:
1659:
1628:
1568:
1469:
1076:
1068:
975:
586:
1551:
1526:
809:
324:
InChI=1S/C9H9ClO3/c1-6-4-7(10)2-3-8(6)13-5-9(11)12/h2-4H,5H2,1H3,(H,11,12)
2415:
2410:
2168:
2150:
2130:
2120:
2112:
2037:
1985:
1938:
1773:
1763:
1733:
1698:
630:
334:
InChI=1/C9H9ClO3/c1-6-4-7(10)2-3-8(6)13-5-9(11)12/h2-4H,5H2,1H3,(H,11,12)
2533:
2513:
2493:
2453:
2359:
2319:
2221:
2085:
2067:
2052:
1943:
1895:
1890:
1885:
1814:
1794:
1789:
1753:
1683:
771:
750:
741:
669:. It is selective for plants with broad leaves, and this includes most
404:
174:
1453:
908:
2523:
2498:
2478:
2314:
2236:
2216:
2135:
2062:
2057:
2042:
1923:
1918:
1703:
1663:
1130:
670:
42:
967:
609:
the
Rothamsted and ICI workers pooled resources and Nutman moved to
480:
Except where otherwise noted, data are given for materials in their
2488:
2339:
2324:
2309:
2287:
2273:
2226:
2208:
2145:
2140:
2047:
2005:
1990:
1928:
1804:
1758:
1738:
1688:
744:. MCPA in soil can be absorbed by plant roots, and translocated in
634:
222:
649:
US Geological Survey estimate of MCPA use in the USA, 1992 to 2017
122:
2518:
2508:
2400:
2125:
1829:
1799:
1675:
826:
791:
666:
658:
511:
425:
234:
33:
893:
510:
introduced in 1945. It selectively controls broad-leaf weeds in
2268:
1980:
1693:
1485:
787:
745:
674:
633:. It is absorbed through the leaves and is translocated to the
550:
515:
154:
1025:
Jealott's Hill: Fifty years of Agricultural Research 1928-1978
2263:
822:
690:
662:
626:
582:
538:
519:
134:
112:
1524:
775:
compartments, and considered to present low potential risk.
522:, which are growth hormones that naturally exist in plants.
284:
2395:
2373:
2000:
1315:
1104:
10.1614/0043-1745(2001)049[0290:ITBTMD]2.0.CO;2
795:
654:
440:
114 to 118 °C (237 to 244 °F; 387 to 391 K)
213:
1581:
1053:
2295:
1285:
2254:
1406:
UNEP publications, OECD SIDS, 4-chloro-2-methylphenol.
1431:
1418:
Guidelines for drinking-water quality, 2nd ed. Vol.2.
1408:
http://www.inchem.org/documents/sids/sids/1570645.pdf
1151:
1116:
753:
to soil particles, with Kf = 0.94 and 1/n = 0.68 of
1022:
585:were also effective. This work took place during
2561:
1420:Health criteria and other supporting information
717:The following commercial products contain MCPA:
246:
988:
897:Industrial & Engineering Chemistry Research
98:
1644:
1029:. Imperial Chemical Industries Ltd. pp.
926:. Weed management handbook. pp. 157–158.
1658:
936:: CS1 maint: multiple names: authors list (
831:(4-Chloro-2-hydroxymethylphenoxyacetic acid)
1625:in the Pesticide Properties DataBase (PPDB)
1192:
1190:
1154:"Estimated Agricultural Use for MCPA, 2017"
821:. The pathway could be the cleavage of the
1651:
1637:
1422:. World Health Organization, Geneva, 1996.
1316:University of Hertfordshire (2016-10-17).
1057:Proceedings of the Royal Society of London
924:Herbicides: Modes of action and metabolism
299:
204:
182:
1550:
953:
921:
622:MCPA acts by mimicking the action of the
266:
1187:
949:
947:
848:
840:
808:
644:
1288:European Journal of Medicinal Chemistry
603:United States Department of Agriculture
295:
69:2-(4-Chloro-2-methylphenoxy)acetic acid
2562:
1343:
1089:
1016:
1014:
1012:
853:Oxidation of MCPA by positive holes h+
845:Oxidation of MCPA by hydroxyl radicals
760:
726:
518:. The mode of action of MCPA is as an
195:
1632:
1481:
1479:
1402:
1400:
1339:
1337:
1311:
1309:
1020:
944:
577:→ MCPA + base·HCl (hydrochloric acid)
557:and dilute base in a straightforward
327:Key: WHKUVVPPKQRRBV-UHFFFAOYSA-N
162:
142:
60:(4-Chloro-2-methylphenoxy)acetic acid
16:Organic compound used as an herbicide
836:
735:
537:research center into the effects of
1434:The Journal of Physical Chemistry A
1152:US Geological Survey (2020-06-18).
1009:
865:h+. The positive holes h+ polarize
504:2-methyl-4-chlorophenoxyacetic acid
337:Key: WHKUVVPPKQRRBV-UHFFFAOYAG
237:
221:
13:
1492:Applied Catalysis B: Environmental
1476:
1397:
1366:10.1111/j.1365-3180.1987.tb00765.x
1334:
1306:
1003:10.1111/j.1744-7348.1940.tb07517.x
804:
14:
2596:
1614:
1253:Journal of Coordination Chemistry
640:
617:
21:methylene cyclopropyl acetic acid
813:Bio-degradation of MCPA in soils
530:In 1936 investigations began at
391:
385:
41:
32:
1575:
1518:
1425:
1412:
1372:
1279:
1244:
1208:
1166:
922:Reade, J., Cobb, A. H. (2002).
873:-COOH bond is split to produce
700:
484:(at 25 °C , 100 kPa).
1145:
1110:
1083:
1047:
982:
915:
887:
875:4-chloro-2-methylphenylformate
712:
565:2-methyl-4-chlorophenol + ClCH
394:
379:
1:
1604:10.1016/j.soilbio.2011.01.014
1584:Soil Biology and Biochemistry
1386:. University of Hertfordshire
1384:Pesticide Properties DataBase
1238:10.1016/S0040-6031(03)00287-9
880:
1504:10.1016/j.apcatb.2003.11.015
1300:10.1016/0223-5234(89)90116-5
1202:Extrnsion Toxicology Network
7:
1265:10.1080/0095897021000010035
685:: its use is mapped by the
420:White to light brown solid
358:Cl-C1=CC=C(OCC(=O)O)C(C)=C1
10:
2601:
825:linkage, yielding MCP and
525:
18:
2466:
2424:
2383:Photosystem II inhibitors
2381:
2372:
2297:Photosystem II inhibitors
2286:
2245:
2207:
2182:
2159:
2111:
2102:
2076:
2028:
2019:
1966:
1957:
1909:
1861:
1828:
1772:
1670:
991:Annals of Applied Biology
478:
460:
366:
346:
311:
82:
66:
54:
49:
40:
31:
2256:Photosystem I inhibitors
819:4-chloro-2-methylphenol)
768:4-chloro-2-methylphenol)
679:restricted use pesticide
547:1-naphthaleneacetic acid
454:amine salt: 866 g/L
1380:"Ecotoxicology of MCPA"
956:Pest Management Science
607:Ministry of Agriculture
1069:10.1098/rspb.1946.0014
854:
846:
814:
801:-COOH + M → -COOM + H
665:, in cereal crops and
650:
1552:10.1038/ismej.2008.21
852:
844:
812:
755:Freundlich adsorption
648:
599:University of Chicago
559:substitution reaction
687:US Geological Survey
624:plant growth hormone
543:indole-3-acetic acid
75:-tolyloxyacetic acid
56:Preferred IUPAC name
2484:aminocyclopyrachlor
2449:sulfometuron methyl
1596:2011SBiBi..43..984N
1543:2008ISMEJ...2..677B
1446:2007JPCA..111.6183B
1358:1987WeedR..27..287H
1230:2003TcAc..407...25K
761:Environmental risks
727:Degradation in soil
595:Rothamsted Research
506:) is a widely used
447:Solubility in water
412: g·mol
28:
2580:Auxinic herbicides
2444:metsulfuron-methyl
2113:Nitrophenyl ethers
1218:Thermochimica Acta
855:
847:
815:
784:conjugated complex
651:
591:multiple discovery
589:and was a case of
488:Infobox references
26:
2557:
2556:
2462:
2461:
2368:
2367:
2282:
2281:
2203:
2202:
2104:Protox inhibitors
2098:
2097:
2094:
2093:
2021:ACCase inhibitors
1454:10.1021/jp067906x
1440:(28): 6183–6190.
1322:sitem.herts.ac.uk
909:10.1021/ie020424x
872:
837:Photo-degradation
786:with metals as a
782:of MCPA can form
736:Behaviors in soil
555:chloroacetic acid
508:phenoxy herbicide
496:Chemical compound
494:
493:
467:Safety data sheet
452:825 mg/L (23 °C),
280:CompTox Dashboard
124:Interactive image
2592:
2379:
2378:
2293:
2292:
2252:
2251:
2161:Pyrimidinediones
2109:
2108:
2026:
2025:
1964:
1963:
1911:Organophosphorus
1653:
1646:
1639:
1630:
1629:
1608:
1607:
1579:
1573:
1572:
1554:
1531:The ISME Journal
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1515:
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1304:
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1283:
1277:
1276:
1259:(9): 1079–1089.
1248:
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1241:
1212:
1206:
1205:
1194:
1185:
1184:
1182:
1181:
1170:
1164:
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1149:
1143:
1142:
1131:10.1038/155497a0
1114:
1108:
1107:
1087:
1081:
1080:
1063:(872): 300–313.
1051:
1045:
1044:
1028:
1018:
1007:
1006:
986:
980:
979:
962:(2): 2033–2043.
951:
942:
941:
935:
927:
919:
913:
912:
903:(5): 1076–1086.
891:
870:
859:hydroxyl radical
411:
396:
393:
387:
381:
374:Chemical formula
304:
303:
288:
286:
270:
250:
239:
225:
208:
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186:
166:
146:
126:
102:
45:
36:
29:
25:
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2458:
2420:
2364:
2278:
2241:
2199:
2178:
2155:
2090:
2072:
2015:
1953:
1905:
1871:flurochloridone
1857:
1843:copper arsenate
1824:
1768:
1666:
1657:
1617:
1612:
1611:
1580:
1576:
1523:
1519:
1484:
1477:
1430:
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1417:
1413:
1405:
1398:
1389:
1387:
1378:
1377:
1373:
1342:
1335:
1326:
1324:
1314:
1307:
1284:
1280:
1249:
1245:
1213:
1209:
1196:
1195:
1188:
1179:
1177:
1172:
1171:
1167:
1158:
1156:
1150:
1146:
1115:
1111:
1088:
1084:
1052:
1048:
1041:
1019:
1010:
987:
983:
968:10.1002/ps.1860
952:
945:
929:
928:
920:
916:
892:
888:
883:
839:
807:
805:Bio-degradation
763:
738:
729:
715:
707:carboxylic acid
703:
643:
620:
572:
568:
528:
497:
490:
485:
455:
453:
449:
430:1.18-1.21 g/cm
409:
399:
390:
384:
376:
362:
359:
354:
353:
342:
339:
338:
335:
329:
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129:
116:
105:
92:
78:
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62:
61:
24:
17:
12:
11:
5:
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2555:
2554:
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2575:Acetic acids
2570:Chloroarenes
2544:pyribenzoxim
2539:prosulfocarb
2529:metam sodium
2391:chlortoluron
2174:saflufenacil
1995:
1876:isoxaflutole
1785:aminopyralid
1749:pretilachlor
1719:dimethenamid
1714:diflufenican
1660:Pest control
1620:
1587:
1583:
1577:
1534:
1530:
1520:
1498:(2): 83–89.
1495:
1491:
1437:
1433:
1427:
1419:
1414:
1388:. Retrieved
1383:
1374:
1349:
1345:
1325:. Retrieved
1321:
1291:
1287:
1281:
1256:
1252:
1246:
1221:
1217:
1210:
1201:
1178:. Retrieved
1168:
1157:. Retrieved
1147:
1122:
1118:
1112:
1095:
1092:Weed Science
1091:
1085:
1060:
1056:
1049:
1024:
994:
990:
984:
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923:
917:
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889:
856:
827:acetate acid
816:
800:
777:
764:
739:
730:
716:
704:
701:Chemical use
695:
657:, including
652:
631:dicotyledons
621:
587:World War II
580:
529:
516:cereal crops
503:
499:
498:
164:ChEMBL394657
83:Identifiers
72:
67:Other names
2416:tebuthiuron
2411:monolinuron
2169:butafenacil
2151:oxyfluorfen
2131:fluorodifen
2121:acifluorfen
2038:chlorazifop
1986:dichlorprop
1939:glufosinate
1901:sulcotrione
1810:pyrithiobac
1764:trifluralin
1734:metolachlor
1729:metazachlor
1699:benfluralin
1125:: 497–498.
713:Brand names
417:Appearance
367:Properties
202:100.002.146
144:CHEBI:50099
2564:Categories
2534:metribuzin
2514:indaziflam
2494:bromoxynil
2454:tribenuron
2360:metamitron
2320:hexazinone
2247:Quaternary
2222:fluroxypyr
2086:sethoxydim
2068:quizalofop
2053:fenoxaprop
1949:piperophos
1944:glyphosate
1896:sethoxydim
1891:nitisinone
1886:mesotrione
1830:Arsenicals
1815:quinclorac
1795:clopyralid
1790:chloramben
1754:propachlor
1684:acetochlor
1664:herbicides
1390:2016-10-17
1327:2016-11-21
1204:. Cornell.
1180:2020-09-01
1159:2020-09-01
1040:0901747017
881:References
772:metabolite
742:surfactant
405:Molar mass
268:D888C394VO
175:ChemSpider
111:3D model (
90:CAS Number
2524:methazole
2499:clomazone
2479:aclonifen
2355:terbutryn
2335:propazine
2330:prometryn
2315:cyanazine
2288:Triazines
2264:cyperquat
2237:triclopyr
2232:thiazopyr
2217:dithiopyr
2209:Pyridines
2136:fomesafen
2063:haloxyfop
2058:fluazifop
2043:cyhalofop
1924:bialaphos
1919:bensulide
1820:quinmerac
1709:diethatyl
1704:butachlor
1561:1751-7362
1512:0926-3373
1462:1089-5639
1174:"Chiptox"
932:cite book
671:deciduous
635:meristems
71:4-Chloro-
2489:Bentazon
2345:simetryn
2340:simazine
2325:prometon
2310:atrazine
2274:paraquat
2227:imazapyr
2146:nitrofen
2141:lactofen
2048:diclofop
2006:mecoprop
1991:fenoprop
1934:fosamine
1929:ethephon
1805:picloram
1774:Aromatic
1759:propanil
1739:oryzalin
1724:flamprop
1689:alachlor
1676:anilines
1672:Anilides
1569:18356824
1470:17585841
1273:98738343
1176:. Nufarm
1139:46259091
1077:20994892
976:19823992
751:adsorbed
601:and the
461:Hazards
2519:juglone
2509:dinoseb
2406:monuron
2401:linuron
2305:ametryn
2126:bifenox
2011:2,4,5-T
1959:Phenoxy
1800:dicamba
1592:Bibcode
1539:Bibcode
1442:Bibcode
1354:Bibcode
1226:Bibcode
792:cadmium
722:others.
681:in the
675:Clovers
673:trees.
667:pasture
659:thistle
526:History
512:pasture
426:Density
235:PubChem
100:94-74-6
2467:Others
2269:diquat
1981:2,4-DB
1968:Auxins
1694:asulam
1567:
1559:
1510:
1468:
1460:
1318:"MCPA"
1271:
1198:"MCPA"
1137:
1119:Nature
1075:
1037:
974:
788:ligand
746:phloem
551:cereal
539:auxins
469:(SDS)
410:200.62
351:SMILES
223:C18528
155:ChEMBL
50:Names
2549:Ziram
2374:Ureas
1976:2,4-D
1777:acids
1269:S2CID
1135:S2CID
1033:–41.
823:ether
691:wheat
655:weeds
627:auxin
583:2,4-D
520:auxin
316:InChI
135:ChEBI
113:JSmol
27:MCPA
2504:DCBN
2474:3-AT
2396:DCMU
2001:MCPB
1996:MCPA
1853:MSMA
1848:DSMA
1622:MCPA
1565:PMID
1557:ISSN
1508:ISSN
1466:PMID
1458:ISSN
1073:PMID
1035:ISBN
972:PMID
938:link
869:, CH
796:lead
794:and
778:The
663:dock
661:and
575:base
573:H +
532:ICIs
514:and
500:MCPA
259:UNII
248:7204
214:KEGG
184:6935
77:MCPA
1600:doi
1547:doi
1500:doi
1450:doi
1438:111
1362:doi
1296:doi
1261:doi
1234:doi
1222:407
1127:doi
1123:155
1100:doi
1065:doi
1061:133
999:doi
964:doi
905:doi
561::
285:EPA
238:CID
2566::
1662::
1598:.
1588:43
1586:.
1563:.
1555:.
1545:.
1533:.
1529:.
1506:.
1496:49
1494:.
1490:.
1478:^
1464:.
1456:.
1448:.
1436:.
1399:^
1382:.
1360:.
1350:27
1348:.
1336:^
1320:.
1308:^
1292:25
1290:.
1267:.
1257:55
1255:.
1232:.
1220:.
1200:.
1189:^
1133:.
1121:.
1096:49
1094:.
1071:.
1059:.
1031:35
1011:^
995:27
993:.
970:.
960:66
958:.
946:^
934:}}
930:{{
901:42
899:.
757:.
693:.
569:CO
392:Cl
1674:/
1652:e
1645:t
1638:v
1606:.
1602::
1594::
1571:.
1549::
1541::
1535:2
1514:.
1502::
1472:.
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