Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1999-04-09
2000-12-05
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
544 59, 544114, 544158, 544159, 544166, 544224, 544238, 548178, 548259, 548261, 5483345, 548541, 549 57, 549 77, 549467, 549475, 562470, 562471, C07D29500, C07D23700, C07D40300, C07D33322, C07D 5948
Patent
active
061568910
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to the production of pyridazine herbicides, and more particularly, it relates to carboxylic acids useful as intermediates for the production of pyridazin-3-one derivatives, a process for producing these intermediates, and a process for producing pyridazin-3-one derivatives from these intermediates.
BACKGROUND ART
Pyridazin-3-one derivatives of formula (7): ##STR4## wherein R.sup.2 and R.sup.3 are independently hydrogen or C.sub.1 -C.sub.3 alkyl, and Q is optionally substituted phenyl, have excellent herbicidal activity, including the following examples: ##STR5## The production of pyridazin-3-one derivatives in a favorable manner is preferred for the development of pyridazine herbicides with excellent activity.
DISCLOSURE OF THE INVENTION
The present inventors have intensively studied to find a process for producing pyridazin-3-one derivatives in a favorable manner. As a result, they have found that carboxylic acids of formula (1): ##STR6## wherein R.sup.2, R.sup.3 and Q are as defined above, can be easily converted into pyridazin-3-one derivatives of formula (7) and therefore serve as their important intermediates, thereby completing the present invention.
Thus, the present invention provides compounds of formula (1): ##STR7## wherein R.sup.2, R.sup.3 and Q are as defined above, which compounds are hereinafter referred to as the present compound(s), a process for their production, and a process for producing pyridazin-3-one derivatives of formula (7): ##STR8## wherein R.sup.2, R.sup.3 and Q are as defined above, comprising ring closing the compounds of formula (1).
Examples of the optionally substituted phenyl group represented by Q may include, for example, groups Q-1, Q-2, Q-3, Q-4 and Q-5 of formula (2): ##STR9## wherein X is hydrogen or halogen;
R.sup.5 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, (C.sub.3 -C.sub.6 cycloalkyl) C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, cyano C.sub.1 -C.sub.6 alkyl, C.sub.1-C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy C.sub.1 -C.sub.3 alkoxy C.sub.1 -C.sub.3 alkyl, carboxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, {(C.sub.1 -C.sub.4 alkoxy) C.sub.1 -C.sub.4 alkoxy}carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cycloalkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, --CH.sub.2 CON(R.sup.12)R.sup.13, --CH.sub.2 COON(R.sup.12)R.sup.13, --CH(C.sub.1 -C.sub.4 alkyl)CON(R.sup.12)R.sup.13, --CH(C.sub.1 -C.sub.4 alkyl)COON(R.sup.12)R.sup.13, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl or hydroxy C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, cyano C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, carboxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.3 -C.sub.8 cycloalkoxy)carbonyl C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyloxy C.sub.2 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonylamino C.sub.2 -C.sub.6 alkyl, hydroxy C.sub.2 -C.sub.6 alkyl, optionally substituted benzyl, optionally substituted phenyl or {(C.sub.1 -C.sub.4 alkoxy) C.sub.1 -C.sub.4 alkyl}carbonyl C.sub.1 -C.sub.6 alkyl, or R.sup.12 and R.sup.13 are taken together to form trimethylene, tetramethylene, pentamethylene, ethyleneoxyethylene or ethylenethioethylene; carboxyl, hydroxy C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkoxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyloxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 haloalkyl)carbonyloxy C.sub.1 -C.sub.6 alkyl or (C.sub.1 -C.sub.6 alkoxy)carbonyl; C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy C.sub.1 -C.sub.3 alkoxy C.sub.1 -C.sub.3 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyloxy C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.su
REFERENCES:
Schober B D et al., J. Heterocycl. Chem.(JHTCAD,0022152X), 89, vol. 26, pp. 169-176.
E.M. Rokhlin, Chemical Abstracts, vol. 60, No. 5, Mar. 2, 1964, p. 5436.
R.B. Bradbury, Chemical Abstracts, vol. 51, No. 4, 1956, p. 9642.
Schroeder Ben
Shah Mukund J.
Sumitomo Chemical Company Limited
LandOfFree
Production of pyridazine herbicides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Production of pyridazine herbicides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Production of pyridazine herbicides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-962812