425:
20:
378:
482:
369:
Dithiocarbamates are described by invoking resonance structures that emphasize the pi-donor properties of the amine group. This bonding arrangement is indicated by a short C–N distance and the coplanarity of the
620:
A. D. Ainley; W. H. Davies; H. Gudgeon; J. C. Harland; W. A. Sexton (1944). "The
Constitution of the So-Called Carbothialdines and the Preparation of Some Homologous Compounds".
524:
406:
358:
474:
to EBDCs for the longer residual period. Both captan and EBDCs were the primary treatments for SBFS in that country until the early 1990s when the US
739:
772:
Gleason, Mark L.; Zhang, Rong; Batzer, Jean C.; Sun, Guangyu (2019-08-25). "Stealth
Pathogens: The Sooty Blotch and Flyspeck Fungal Complex".
846:
723:
691:
605:
478:
banned EBDCs within 77 days to harvest. This effectively made summer use impossible, reduced EBDC use overall, and radically increased SBFS.
485:
541:
574:
774:
475:
259:
101:
397:
ligands. Another consequence of the C–N multiple bonding is that rotation about that bond is subject to a high barrier.
873:
868:
783:
385:
Because of the pi-donation from nitrogen, dithiocarbamates are more basic than structurally related anions such as
878:
489:
467:
743:
463:
595:
715:
670:
Coucouvanis, Dimitri (1979). "The chemistry of the dithioacid and 1,1-dithiolate complexes, 1968–1977".
194:
Dithiocarbamate salts are pale colored solids that are soluble in water and polar organic solvents.
811:
59:
842:
803:
795:
719:
687:
601:
570:
537:
386:
307:
36:
643:
John R. Grunwell (1970). "Reaction of
Grignard Reagents with Tetramethylthiuram Disulfide ".
834:
829:
Theo Mang; Jürgen Braun; Wilfried Dresel; Jürgen Omeis (2011). "Lubricants, 2. Components".
787:
707:
679:
652:
625:
562:
529:
331:
125:
121:
44:
791:
229:
23:
General chemical structure of dithiocarbamate esters. R and R" is any group (typically
862:
815:
459:
418:
105:
78:
458:), have been used extensively as fungicides in agriculture since the 1940s. In the
424:
533:
591:
683:
414:
19:
838:
799:
566:
357:
Dithiocarbamates react with transition metal salts to give a wide variety of
439:
410:
394:
66:
807:
377:
629:
502:
455:
390:
24:
656:
522:
Engels, Hans-Wilhelm; et al. "Rubber, 4. Chemicals and
Additives".
48:
28:
481:
471:
409:
are useful in industry. Zinc dithiocarbamates are used to modify the
74:
70:
480:
466:
in the late 1950s and early 1960s and were quickly put to work on
451:
443:
432:
Some dithiocarbamates, specifically ethylene bisdithiocarbamates (
423:
376:
117:
18:
104:. Dithiocarbamates and their derivatives are widely used in the
597:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
557:
Rüdiger
Schubart (2000). "Dithiocarbamic Acid and Derivatives".
447:
228:
In the presence of diimides or pyridine, these acids convert to
600:(6th ed.), New York: Wiley-Interscience, p. 1297,
492:, serving as an antioxidant and protecting metal surfaces.
742:. The American Phytopathological Society. Archived from
262:
can be prepared by methylation of the dithiocarbamate:
84:
Dithiocarbamate also refers to the dithiocarbamate ion
381:
Main resonance structures of a dithiocarbamate anion.
202:
A primary amine and carbon disulfide react to give a
767:
765:
763:
761:
77:
atoms (when only 1 oxygen is replaced the result is
421:. They are used as ligands for chelating metals.
428:Structure of the dimethyldithiocarbamate of zinc.
258:Dithiocarbamates are readily S-alkylated. Thus,
559:Ullmann's Encyclopedia of Industrial Chemistry
525:Ullmann's Encyclopedia of Industrial Chemistry
831:Ullmanns Encyclopedia of Industrial Chemistry
8:
490:additive in some extreme pressure gear oils
454:) or a combination of manganese and zinc (
407:transition metal dithiocarbamate complexes
359:transition metal dithiocarbamate complexes
374:core as well as the atoms attached to N.
306:Oxidation of dithiocarbamates gives the
246:
242:
238:
220:
216:
212:
155:
142:
138:
134:
87:
53:
514:
334:to give esters of dithiocarbamic acid:
393:. Consequently, they tend to bind as
7:
486:Methylenebis(dibutyldithiocarbamate)
792:10.1146/annurev-phyto-082718-100237
674:. Progress in Inorganic Chemistry.
100:and its salts. A common example is
14:
438:), in the form of complexes with
775:Annual Review of Phytopathology
740:"A Short History of Fungicides"
476:Environmental Protection Agency
128:to form dithiocarbamate salts:
16:Chemical group (>N–C(=S)–S–)
417:with sulfur, a process called
330:Thiuram disulfides react with
260:methyl dimethyldithiocarbamate
1:
534:10.1002/14356007.a23_365.pub2
470:. Many growers switched from
102:sodium diethyldithiocarbamate
895:
712:Chemistry of the Elements
710:; Earnshaw, Alan (1997).
684:10.1002/9780470166277.ch5
468:sooty blotch and flyspeck
65:. It is the analog of a
839:10.1002/14356007.o15_o04
567:10.1002/14356007.a09_001
561:. Weinheim: Wiley-VCH.
528:. Weinheim: Wiley-VCH.
245:→ RN=C=S + S=C(NHR')
493:
429:
382:
163:Ammonia reacts with CS
73:atoms are replaced by
32:
716:Butterworth-Heinemann
708:Greenwood, Norman N.
484:
427:
380:
365:Structure and bonding
31:), and R' is organyl.
22:
630:10.1039/JR9440000147
657:10.1021/jo00830a052
590:Smith, Michael B.;
204:dithiocarbamic acid
198:Dithiocarbamic acid
494:
464:registered for use
430:
387:dithiocarboxylates
383:
33:
874:Functional groups
869:CYP3A4 inhibitors
848:978-3-527-30673-2
725:978-0-08-037941-8
693:978-0-470-16627-7
672:Prog. Inorg. Chem
607:978-0-471-72091-1
462:they began to be
332:Grignard reagents
308:thiuram disulfide
47:with the general
37:organic chemistry
886:
879:Dithiocarbamates
853:
852:
826:
820:
819:
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756:
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746:on 16 April 2016
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714:(2nd ed.).
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651:(5): 1500–1501.
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633:
617:
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519:
437:
436:
341:+ R'MgX → R
249:
224:
159:
153:
152:
149:
126:sodium hydroxide
122:carbon disulfide
99:
98:
97:
94:
64:
57:
45:functional group
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230:isothiocyanates
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147:
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141:+ NaOH → R
140:
136:
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116:Many secondary
114:
95:
92:
91:
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85:
62:
55:
51:
41:dithiocarbamate
17:
12:
11:
5:
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821:
784:Annual Reviews
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543:978-3527306732
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345:NC(S)SR' + R
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69:in which both
63:>N−C(=S)−S−
15:
13:
10:
9:
6:
4:
3:
2:
891:
880:
877:
875:
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866:
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850:
844:
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836:
833:. Wiley-VCH.
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622:J. Chem. Soc.
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576:3-527-30673-0
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469:
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460:United States
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419:vulcanization
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241:H + C(=NR')
235:
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131:
130:
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106:vulcanization
103:
82:
80:
79:thiocarbamate
76:
72:
68:
61:
50:
46:
42:
38:
30:
26:
21:
830:
824:
779:
773:
748:. Retrieved
744:the original
734:
711:
702:
675:
671:
665:
648:
645:J. Org. Chem
644:
638:
621:
615:
596:
592:March, Jerry
585:
558:
552:
523:
517:
431:
411:crosslinking
404:
401:Applications
384:
368:
356:
329:
305:
257:
227:
203:
201:
193:
162:
115:
83:
40:
34:
786:: 135–164.
678:: 301–469.
624:: 147–152.
415:polyolefins
413:of certain
219:→ R(H)NCS
167:similarly:
120:react with
108:of rubber.
56:N−C(=S)−S−R
863:Categories
509:References
278:Na + (CH
816:172137916
800:0066-4286
440:manganese
395:bidentate
391:xanthates
254:Reactions
137:NH + CS
112:Formation
67:carbamate
60:structure
808:31150591
594:(2007),
503:Xanthate
497:See also
456:mancozeb
405:Several
298:NC(S)SCH
25:hydrogen
290:→ (CH
237:R(H)NCS
154:Na + H
49:formula
29:organyl
845:
814:
806:
798:
750:10 May
722:
690:
604:
573:
540:
488:is an
472:captan
118:amines
75:sulfur
71:oxygen
812:S2CID
782:(1).
452:zineb
444:maneb
435:EBDCs
326:+ 2e
302:+ Na
215:+ CS
179:→ H
175:+ CS
43:is a
843:ISBN
804:PMID
796:ISSN
752:2016
720:ISBN
688:ISBN
602:ISBN
571:ISBN
538:ISBN
448:zinc
389:and
171:2 NH
124:and
90:N−CS
58:and
39:, a
835:doi
788:doi
680:doi
653:doi
626:doi
563:doi
530:doi
446:),
370:NCS
353:MgX
349:NCS
322:→
318:NCS
314:2 R
274:NCS
266:(CH
232::
211:RNH
183:NCS
145:NCS
81:).
35:In
27:or
865::
841:.
810:.
802:.
794:.
780:57
778:.
760:^
718:.
686:.
676:26
649:35
647:.
569:.
536:.
361:.
310::
286:SO
282:O)
206::
187:NH
851:.
837::
818:.
790::
754:.
728:.
696:.
682::
659:.
655::
632:.
628::
579:.
565::
546:.
532::
450:(
442:(
372:2
351:2
347:2
343:2
339:2
324:2
320:2
316:2
300:3
296:2
294:)
292:3
288:2
284:2
280:3
276:2
272:2
270:)
268:3
247:2
243:2
239:2
223:H
221:2
217:2
213:2
189:4
185:2
181:2
177:2
173:3
165:2
158:O
156:2
151:2
148:−
143:2
139:2
135:2
133:R
96:2
93:−
88:2
86:R
54:2
52:R
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