Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1995-09-21
1998-01-06
Datlow, Philip I.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
544 73, 544105, 544135, 544137, 544153, 544164, 546119, 546196, 546198, 546223, 546244, C07D21172, C07D26530, C07D47104, C07D49804
Patent
active
057056390
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
U.S. Pat. No. 4,925,481, U.S. Pat. No. 4,213,773 and U.S. Pat. No. 4,881,967 disclose herbicidal tetrahydrotriazolopyridin-3-ones and methods for preparation, but do not disclose the instant process.
SUMMARY OF THE INVENTION
The invention pertains to a process to prepare compounds of Formula I ##STR2## R.sup.1 is H, halogen, OH, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub. haloallcyl, C.sub.1 -C.sub. alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkylthio, C.sub.2 -C.sub.6 alkenyloxy, C.sub.2 -C.sub.6 alkenylthio, C.sub.2 -C.sub.6 haloalkenyloxy, C.sub.2 -C.sub.6 haloalkenylthio, C.sub.3 -C.sub.6 alkynyloxy, C.sub.3 -C.sub.6 alkynylthio, C.sub.3 -C.sub.6 haloalkynyloxy, C.sub.3 -C.sub.6 haloalkynylthio, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.4 -C.sub.8 alkenyloxycarbonyl, C.sub.3 -C.sub.8 alkylcarbonylalkoxy, C.sub.3 -C.sub.8 alkylcarbonylalkylthio, C.sub.3 -C.sub.8 alkoxycarbonylalkoxy, C.sub.3 -C.sub.8 alkoxycarbonylalkylthio, C.sub.5 -C.sub.8 alkenyloxycarbonylalkoxy, C.sub.5 -C.sub.8 alkenyloxycarbonylalkylthio, phenoxy and phenylthio where the phenyl groups are optionally substituted with halogen; -C.sub.6 alkoxyalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl and ##STR3## R.sup.4 is H, C.sub.1 -C.sub.3 alkyl and halogen; R.sup.5 is H, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, cyclopropyl, vinyl, C.sub.2 alkynyl, CN, C(O)R.sup.6, C(O).sub.2 R.sup.6, C(O)NR.sup.6 R.sup.7, CR.sup.8 R.sup.9 CN, CR.sup.8 R.sup.9 C(O)R.sup.6, CR.sup.8 R.sup.9 C(O).sub.2 R.sup.6, CR.sup.8 R.sup.9 C(O)NR.sup.6 R.sup.7, CHR.sup.8 OH, CHR.sup.8 OC(O)R.sup.6 and OCHR.sup.8 OC(O)NR.sup.6 R.sup.7 ; independently selected from the defined substituents; ##STR4## wherein R.sup.2 is C.sub.1 -C.sub.6 alkyl; with an anhydrous acid to produce compounds of Formula IV ##STR5## wherein X is Cl or Br and R.sup.2 is described above; second, reacting compounds of Formula IV with Formula III hydrazines or salts thereof ##STR6## wherein R.sup.2 is defined above; and third, heating compounds of Formula II in liquid form optionally in the presence of an acid to produce Formula I compounds at 0.degree.-150.degree. C. with or without a solvent ##STR7## wherein Q and Z are defined above.
This invention further pertains to novel Formulae II and IV intermediates ##STR8## wherein Q, R.sup.2, and X are defined above.
In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl", includes straight chain or branched alkyl, such as methyl, ethyl, n-propyl, isopropyl and the different butyl, pentyl, and hexyl isomers. "Alkoxy" used either alone or in compound words such as "haloalkoxy" includes methoxy, ethoxy, n-propoxy, isopropoxy, and the different butoxy, pentoxy, and hexyloxy isomers. "Alkenyl" used either alone or in compound words such as "haloalkenyl" or "alkenylthio" includes straight chain or branched alkenes, such as vinyl, 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl, pentenyl, and hexenyl isomers. "Alkynyl" used either alone or in compound words such as "haloalkynyl" or "alkynylthio" includes straight or branched alkynes, such as 1-propynyl, 3-propynyl, and the different butynyl, pentynyl, and hexynyl isomers. "Alkylthio" includes methylthio, ethylthio, and the different propylthio, butylthio, pentylthio, and hexylthio isomers.
The term "halogen", used either alone or in compound words such as "haloalkyl", means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl can be partially or fully substituted with halogen atoms, which can be the same or different. Examples of haloalkyl include CF.sub.3, CH.sub.2 CH.sub.2 F, CF.sub.2 CF.sub.3, CH.sub.2 CHFCl, and CHBrCH.sub.3. The terms "haloalkenyl" and "haloalkynyl" are defined analogously to the term "haloalkyl".
The total number of carbon atoms in a substituent group is indicated by the "C.sub.i -C.sub.j " prefix where i and j are numbers from 1 to 8.
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Barluenga, J. et al, Synthesis, 831-832 (1984).
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Kwok, R. et al., J. Org. Chem., 32, 738-740 (1967).
Moriconi, E.J. et al., J. Org. Chem., 33(5), 2109-2111 (1968).
Datlow Philip I.
E. I. Du Pont de Nemours and Company
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