Patent EA-001515-B1 (EA)
Title: Pyrazole-4-yl-hetaroyl derivatives as herbicides
Inventor: OTTEN MARTIN
IPC: C07D411/06
Filed: 1997-02-20
Abstract: 1. A pyrazol-4-yl-hetaroyl derivatives of the formula I   where the substituents have the following meanings: L and M are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4 alkoxy; halogen, cyano, nitro; X is oxygen or sulfur which can be substituted by one or two oxygens; n is zero, one, two; R<1> is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4 alkoxy; halogen; phenyl which may be mono- or polysubstituted by the following groups: C1-C4 alkyl, hydrogen, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, nitro, cyano, C1-C4 alkyloxycarbonyl; R<2> is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4 alkoxy; halogen; phenyl which may be mono- or polysubstituted by the following groups: C1-C4 alkyl, hydrogen, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, nitro, cyano, C1-C4 alkyloxycarbonyl; R<2> and R<3> may form a linkage; R<3> is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4 alkoxy; halo; phenyl which may be mono- or polysubstituted by the following groups: C1-C4 alkyl, hydrogen, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, nitro, cyano, C1-C4 alkyloxycarbonyl; R<3> and R<2> may form a linkage; R<4> is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C1-C4 alkoxy; halogen; phenyl which may be mono- or polysubstituted by the following groups: C1-C4 alkyl, hydrogen, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, nitro, cyano, C1-C4 alkyloxycarbonyl; Q is a pyrazole ring, linked in the 4-position, of the formula II   where R<5> is C1-C4 alkyl, R<6> is hydrogen, C1-C4 alkyl or C1-C4 haloalkyl and R<7> is hydrogen, C1-C4 alkylsulfonyl, phenylsulfonyl or alkylphenylsulfonyl, or an agriculturally useful salts thereof. 2. The pyrazol-4-ylhetaroyl derivatives of the formula Ia according claim 1   where L is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano or nitro and M is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano or nitro and Q, X, R<1> to R<4> and n have the meanings given in claim 1. 3. The pyrazol-4-ylhetaroyl derivatives of the formula Ib according to claim 1   where L is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano or nitro and M is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano or nitro and Q, X, R<1> to R<4> and n have the meanings given in claim 1. 4. The pyrazol-4-ylhetaroyl derivatives of the formula I as claimed in claim 1 where the radicals L and M are hydrogen, methyl, methoxy, chlorine, cyano, nitro and trifluoromethyl. 5. The pyrazol-4-ylhetaroyl derivatives of the formula Ic as claimed in claim 1   where L is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano or nitro and M is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano or nitro and Q, R<1> to R<4> and n have the meanings given in claim 1. 6. The pyrazol-4-ylhetaroyl derivatives of the formula Id as claimed in claim 1   where L is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano or nitro and M is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano or nitro and Q, R<1>, R<4> and n have the meanings given in claim 1. 7. The pyrazol-4-ylhetaroyl derivatives of the formula Id2 as claimed in claim 1   where L is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano or nitro and M is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano or nitro and m is zero, one or two and Q, R<1>, R<4> and n have the meanings given in claim 1. 8. The pyrazol-4-ylhetaroyl derivatives of the formula Ie as claimed in claim 1   where L is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano or nitro and M is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano or nitro and m is zero, one or two and Q, R<1> to R<4> and n have the meanings given in claim 1. 9. A process for the preparation of a compound of the formula I as claimed in claim 1, characterised in that the corresponding parent materials of the formula IIa   are acylated with an acid chloranhydride of the formula IIIa or an acid of the formula IIIb     where L, M, X, R<1> to R<4>, R<5>, R<6> and n have the meanings given in claim 1 and the acylation product is rearranged in the presence of a catalyst. 10. A herbicidal composition, comprising at least one pyrazol-4-ylhetaroyl derivative of the formula I as claimed in claim 1 and customary inert additives. 11. A method for controlling undesirable vegetation, which comprises allowing a herbicidally active amount of a pyrazol-4-ylhetaroyl derivative of the formula I as claimed in claim 1 to act on the plants or their environment.