Substituted 1-(diazinyl)pyrazol-4-ylacetic acids, processes for their preparation and their use as herbicides and plant growth regulators

A compound of the formula (I) or a salt thereof

• wherein Het is a six-membered heteroaromatic radical having two heteroatoms as ring atoms, where the heteroatoms in the ring are nitrogen atoms and at least one nitrogen atom in the ring is located in the 1,3-position to the ring carbon atom which is attached to the pyrazole radical;
• wherein R1 is hydrogen or a hydrolyzable radical;
• wherein:
• R2 and R3 are as follows:
• R2 is hydrogen, halogen, or (C1-C6)-alkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkoxy, (C1-C4)-alkylthio, and (C1 -C4)-haloalkoxy;
• and
• R3 is hydrogen, halogen, or (C1-C6)-alkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkoxy, (C1-C4)-alkylthio, and (C1-C4)-haloalkoxy;
• or
• R2 and R3 together with the carbon atom to which they are attached are a carbocyclic saturated or partially unsaturated ring having 3 to 6 carbon atoms which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and (C1-C4)-alkyl;
• and
• wherein R4 is:
• hydrogen, halogen, or cyano;
• or
• (C1-C6)-alkyl, (C2-C6)-alkenyl, or (C2-C6)-alkynyl, where each of the three last-mentioned radicals independently is unsubstituted or substituted by one or more radicals selected from the group consisting of:
• halogen, cyano, hydroxyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4)-alkylthio and optionally halogen-, cyano-, (C1-C4)-alkyl-, and (C1-C4)-haloalkyl-substituted (C3-C9)-cycloalkyl;
• or
• (C3-C9)-cycloalkyl, (C5-C9)-cycloalkenyl, or (C5-C9)-cycloalkynyl, where each of the 3 last-mentioned radicals independently is unsubstituted or substituted by one or more radicals selected from the group consisting of:
• halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, and (C1-C4)-alkylthio;
• or
• phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, carboxy, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4)-alkylthio, (C1-C4)-alkanoyl, (C1-C4)-haloalkanoyl, [(C1-C4)-alkoxy]carbonyl, and [(C1-C4)-haloalkoxy]carbonyl;
• or
• (C1-C6)-alkanoyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4)-alkylthio, and optionally (C1-C4)-alkyl- or (C1-C4)-haloalkyl-substituted (C3-C6)-cycloalkyl;
• or
• [(C1-C4)-alkoxy]carbonyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4)-alkylthio, and optionally (C1-C4)-alkyl- or (C1-C4)-haloalkyl-substituted (C3-C6)-cycloalkyl;
• or
• [(C3-C9)-cycloalkoxy]carbonyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, and (C1-C4)-alkylthio;
• wherein R5 is:
• an aryl radical which is unsubstituted or substituted and, including substituents, has 6 to 30 carbon atoms;
• or
• a heteroaromatic radical having 1 to 4 ring heteroatoms selected from the group consisting of N, O, and S, which is unsubstituted or substituted and, including substituents, has 1 to 30 carbon atoms;
• and
• wherein (R6)n are n substituents R6, where R6, in the case that n=1, or each of the substituents R6 independently of the others, in the case that n is greater than 1, is:
• a radical halogen, hydroxyl, amino, nitro, carboxy, cyano, carbamoyl, (C1-C6)-alkyl, (C1-C6) haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-akylthio-(C1-C4)-alkyl, mono- or di-[(C1-C4)-alkyl]aminoalkyl, hydroxy-(C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C6)-alkylthio, (C1-C6)-haloalkylthio, [(C1-C6)-alkoxy]carbonyl, [(C1-C6)-haloalkoxy]carbonyl, (C1-C6)-alkanoyl, (C1-C6)-haloalkanoyl, mono- or di-[(C1-C4)-alkyl]aminocarbonyl, mono- or di-[(C1-C6)-acyl]amino, mono- or di-[(C1-C4)-alkyl]amino, N—[(C1-C6)-acyl]-N—[(C1-C6)-alkyl]amino, (C1-C6)-alkylsulfinyl, (C1-C6)-haloalkylsulfinyl, (C1-C6)-alkylsulfonyl, or (C1-C6)-haloalkylsulfonyl;
• or
• (C3-C9)-cycloalkyl or (C5-C9)-cycloalkenyl, where each of the two last-mentioned radicals independently is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, and (C1-C4)-haloalkyl;
• and
• wherein n is 0, 1, 2 or 3.