Patent EA-000753-B1 (EA)
Title: Pyrazol-4-yl-benzoyl derivatives and their use as herbicides
Inventor: OTTEN MARTINA
IPC: A01N43/56
Filed: 1996-08-29
Abstract: l. Pyrazol-4-yl-benzoyl derivatives of Formula I   where the substituents have the following meanings: L, M represent hydrogen, C1-C6alkyl, C2-C6akenyl, C2-C6alkynyl, C1-C4alkoxy, wherein these groups can be optionally substituted by one to five halogen atoms or C1-C4 alkoxy group; halogen, cyano, nitro, a group -(A)m-S(0)nR<1> or a group -(A)m-CO-R<2>; Y represents a group comprising C=O. C=N-R<3>, CR<7>-NR<5>R<6>, CR<7>-OR<8>, CR<10>R<11>, CR<7>-SR<8>; heteroatom selected from the group comprising oxygen, sulfur and nitrogen; X represents a chain (-CR<12>C<13>-). (-CR<12>R<13>-CR<21>R<22>), (-CR<12>=CR<13>-) , (-CR<12>R<13>-CR<12>=CR<13>-); NR<23>; a bond between X and Y may be saturated or unsaturated; A represents oxygen or NR<14>; m is zero or one; n is zero, one or two; R<1> represents C1-C4alkyl, C1-C4haloalkyl or NR<14>; R<3> represents hydrogen, NR<9>R<4>, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkinyl; optionally substituted phenyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; optionally substituted benzyloxy, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<4>  represents hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl. C2-C6alkinyl, C=O-NRl<4>;optionally substituted phenyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<9> represents hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl. C2-C6alkynyl, C=O-NRl<4>; optionally substituted phenyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<5>, R<6> independently represent hydrogen, C1-C6alkyl, C2-C6alkenyl, C1-C4haloalkyl, C2-C6haloalkenyl, C1-C6alkoxy, C1-C6haloalkoxy; optionally substituted phenyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<7> represents hydrogen, C1-C6alkyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy; optionally substituted phenyl, wherein the substituents can be selected from the group comprising from one to three halogens, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, nitro; R<7> and R<21> or R<7> and R<23> or R<7> and R<12> can form a bond; R<8> represents hydrogen, C1-C6alkyl, C1-C4halogenalkyl, optionally substituted phenyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; optionally substituted benzyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<10>, R<11> independently represent hydrogen, C1-C6alkyl; optionally substituted phenyl, wherein the substituents can be selected from the group comprising from one to three halogens, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, nitro; R<10> and R<12> or R<10> and R<21> or R<10> and R<23> can form a bond; R<10> and R<11> can form together1,4-dioxobutane-1,4-diyl, 1,3-dioxapentane-1,5diyl or 2,4-dioxapentane-1,5-diyl chain, substituted by hydrogen or C1-C4alkyl; R<12>, R<13> independently represent hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy; optionally substituted phenyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<14> represents C1-C6alkyl; R<21> represents hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy; optionally substituted phenyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<22> represents hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy; optionally substituted phenyl, wherein the substituents can be selected from the group comprising C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano, nitro; R<23> represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C1-C6alkoxy; optionally substituted by C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4haloalkyl, halogen, cyano group, nitro group phenyl or benzyl; Q represents pyrazole ring, linked in the 4-position of the formula II   where R<15>represents C1-C4alkyl, R<16> is hydrogen, C1-C4alkyl or C1-C4haloalkyl and R<17> is hydrogen, C1-C4alkylsulfonyl, phenylsulfonyl or alkylphenylsulfonyl, wherein if Y represents C=O, X is not NR<23> or an agriculturally useful salt thereof   2. A pyrazol-4-yl-benzoyl derivative of the formula   where L represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4 halogenalkyl, C1-C4halogenalkoxy, C1-C4halogenalkylthio, C1-C4alkylsulfonyl, halogen, nitro or cyano and M represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4 halogenalkyl, C1-C4halogenalkoxy, C1-C4halogenalkylthio, C1-C4alkylsulfonyl, halogen, nitro or cyano and Q, X, n and Y have the meanings given in claim 1, wherein if Y represents C=O, X is not NR<23>. 3. A pyrazol-4-yl-benzoyl derivative of the formula Ib   where L represents C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, cyano or nitro and M represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, cyano or nitro and Q, X, n and Y have the meanings given in claim 1, wherein if Y represents C=O, X is not NR<23>. 4. A pyrazol-4-yl-benzoyl derivative of the formula I as claimed in claim 1 where the radicals L and M represent hydrogen, methyl, methoxy, chlorine, cyano, nitro and trifluoromethyl. 5. A pyrazol-4-yl-benzoyl derivative of the formula Ic   where L represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, cyano or nitro and M represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, cyano or nitro and Q, n Y and R<22>, R<21>, R<12> and R<13>  have the meanings given in claim 1. 6. A pyrazol-4-yl-benzoyl derivative of the formula Id   where L represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, cyano or nitro and M represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, cyano or nitro and Q, n Y and R<12> and R<13>  have the meanings given in claim 1. 7. A pyrazol-4-yl-benzoyl derivative of the formula Ie   where L represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, cyano or nitro and M represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, halogen, cyano or nitro and Q, n Y and R<12> and R<13>  have the meanings given in claim 1. 8. Pyrazol-4-yl-benzoyl derivative of formula I as claimed in claim 1, wherein n is one or two, and Y represents CR<7>-OR<8>, where R<7> and R<8> 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, wherein pyrazols of the formula IIa   acylate with an acid chloride of the formula IIIa or an acid of the formula IIIb   where R<15>, R<16>, L. M, X, n and Y have meanings given in claim 1, and subjecting the acylation product to a rearrangement reaction in the presence of a catalyst to obtain the compound I. 10. A herbicidal composition, comprising at least one pyrazol-4-yl-benzoyl 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-yl-benzoyl derivative of the formula I as claimed in claim 1 to act on the plants or their environment.