Production of pyridazine herbicides

Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent

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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.

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