# Patent

## Title
Herbicides

## Abstract

Compounds of formula




wherein the substituents have the meanings given in claim 1, and agronomically tolerable salts, isomers and enantiomers of those compounds, are suitable for use as herbicides.

## Background
This application is a divisional application of U.S. Ser. No. 10/070,767, filed Jun. 25, 2002 now U.S. Pat. No. 6,894,005, the contents of which are incorporated herein by reference.


The present invention relates to novel herbicidally active heterocycles substituted by a phenyl group, to processes for the preparation thereof, to compositions comprising such compounds, and to the use thereof in controlling weeds, especially in crops of useful plants, or in inhibiting plant growth.
3-Hydroxy-4-aryl-5-oxo-pyrazoline derivatives having herbicidal action are described, for example, in EP-A-0 508 126, WO 96/25395 and WO 96/21652.
Novel heterocycles substituted by a phenyl group having herbicidal and growth-inhibiting properties have now been found.
The present invention accordingly relates to compounds of formula I




wherein

    R1 and R3 are each independently of the other ethyl, haloethyl, ethynyl, C1-C2alkoxy, C1-C2haloalkoxy, C1-C2alkylcarbonyl, C1-C2hydroxyalkyl or C1-C2alkoxycarbonyl;
    Q is a group









    R4 and R5 are each independently of the other C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C2-C10-N-alkoxyiminoalkyl, C2-C10alkoxycarbonylalkyl, C1-C10aminoalkyl, C3-C10dialkylaminoalkyl, C2-C10alkylaminoalkyl, C1-C10cyanoalkyl, C4-C10cycloalkylalkyl, C1-C10phenylalkyl, C1-C10heteroarylalkyl, C1-C10phenoxyalkyl, C1-C10heteroaryloxyalkyl, C1-C10alkylideneaminooxyalkyl, C1-C10nitroalkyl, C1-C10trialkylsilylalkyl, C2-C10alkylaminocarbonylalkyl, C2-C10dialkylaminocarbonylalkyl, C2-C10alkylaminocarbonyloxyalkyl, C3-C10dialkylaminocarbonyloxalkyl, C2-C10alkoxycarbonylaminoalkyl, C1-C10-N-alkoxycarbonyl-N-alkylaminoalkyl, C1-C10cycloalkyl, aryl or heteroaryl; or
    R4 and R5, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur and that, in addition, may contain a fused or spiro-bound alkylene or alkenylene chain consisting of from 2 to 6 carbon atoms, which chain may in turn contain one or two hetero atoms selected from oxygen and sulfur, wherein the cyclic group may be substituted by phenyl or benzyl, which in turn may be substituted by halogen, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, hydroxy, C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy, C1-C6haloalkoxy or by nitro;
    R2, R6 and R32 are each independently of the others C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
    R7, R31 and R33 are each independently of the others hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C2-C10alkoxyalkyl;
    R8 is hydrogen, C1-C10alkyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
    R6 and R7 or R2 and R31 or R32 and R33, together with the atom to which they are bonded, form a saturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur; or R6 and R8, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R9, R10, R11 and R12 are each independently of the others C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
    R9 and R11 or R9 and R10, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R13, R14, R34 and R35 are each independently of the others C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
    R13 and R14 or R34 and R35, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R15 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C2-C10alkoxycarbonylalkyl, C1-C10aminoalkyl, C3-C10dialkylaminoalkyl, C2-C10alkylaminoalkyl, C1-C10cyanoalkyl, C4-C10cycloalkylalkyl, C1-C10phenylalkyl, C1-C10heteroarylalkyl, C1-C10phenoxyalkyl, C1-C10heteroaryloxyalkyl, C1-C10nitroalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
    R16 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthiolkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
    R17 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
    R18 is hydrogen, C2-C10alkenyl, C2-C10alkynyl, C1-C10alkyl or C1-C10alkoxyalkyl; or
    R17 and R18, together with the atoms to which they are bonded, form a 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    Y is oxygen, sulfur, C—R19 or N—R36;
    R19 and R36 are each independently of the other C1-C10alkyl, C1-C10haloalkyl, phenyl or heteroaryl; or
    R18 and R19 or R18 and R36, together with the atom to which they are bonded, form a saturated 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    G1, G2, G3, G4, G5, G6, G7, G8, G9 and G10 are each independently of the others hydrogen, —C(X1)—R20, —C(X2)—X3—R21, —C(X4)—N(R22)—R23, —SO2—R24, an alkali metal cation, alkaline earth metal cation, sulfonium cation or ammonium cation, —P(X5)(R25)—R26 or —CH2—X6—R27;
    X1, X2, X3, X4, X5 and X6 are each independently of the others oxygen or sulfur;
    R20, R21, R22 and R23 are each independently of the others hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl, C4-C10alkenyloxyalkyl, C4-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C1-C5alkylsulfoxyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylideneaminooxy-C1-C5alkyl, C1-C5alkylcarbonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminocarbonyl-C1-C5alkyl, C1-C5alkylcarbonylamino-C1-C5alkyl, C1-C5alkylcarbonyl-(C2-C5alkyl)-aminoalkyl, C3-C6trialkylsilyl-C1-C5alkyl, phenyl-C1-C5alkyl, heteroaryl-C1-C5alkyl, phenoxy-C1-C5alkyl, heteroaryloxy-C1-C5alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or heteroaryl or heteroarylamino, or heteroaryl or heteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diheteroarylamino, or diheteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, phenylamino, or phenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diphenylamino, or diphenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or C3-C7cycloalkylamino, di-C3-C7cycloalkylamino or C3-C7cycloalkoxy;
    R24, R25 and R26 are hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl, C4-C10alkenyloxyalkyl, C4-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C1-C5alkylsulfoxyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylideneaminooxy-C1-C5alkyl, C1-C5alkylcarbonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminocarbonyl-C1-C5alkyl, C1-C5alkylcarbonylamino-C1-C5alkyl, C1-C5alkylcarbonyl-(C2-C5alkyl)-aminoalkyl, C3-C6trialkylsilyl-C1-C5alkyl, phenyl-C1-C5alkyl, heteroaryl-C1-C5alkyl, phenoxy-C1-C5alkyl, heteroaryloxy-C1-C5alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or heteroaryl or heteroarylamino, or heteroaryl or heteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diheteroarylamino, or diheteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, phenylamino, or phenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diphenylamino, or diphenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or C3-C7cycloalkylamino, di-C3-C7cycloalkylamino, C3-C7cycloalkoxy, C1-C10alkoxy, C1-C10haloalkoxy, C1-C5alkylamino, C2-C8dialkylamino, benzyloxy or phenoxy, wherein the benzyl and phenyl groups may in turn be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
    R27 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl, C4-C10alkenyloxyalkyl, C4-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C1-C5alkylsulfoxyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylideneaminooxy-C1-C5alkyl, C1-C5alkylcarbonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminocarbonyl-C1-C5alkyl, C1-C5alkylcarbonylamino-C1-C5alkyl, C1-C5alkylcarbonyl-(C2-C5alkyl)-aminoalkyl, C3-C6trialkylsilyl-C1-C5alkyl, phenyl-C1-C5alkyl, heteroaryl-C1-C5alkyl, phenoxy-C1-C5alkyl, heteroaryloxy-C1-C5alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or heteroaryl or heteroarylamino, or heteroaryl or heteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diheteroarylamino, diheteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or phenylamino, phenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diphenylamino, diphenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, C3-C7cycloalkylamino, di-C3-C7cycloalkylamino, C3-C7cycloalkoxy or C1-C10alkylcarbonyl;
    Y2 is oxygen, sulfur, C—R140—R141 or N—R142,
    R55 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
    R137 is hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C1-C10alkoxyalkyl; or
    R55 and R137, together with the atoms to which they are bonded, form a 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R138 and R139 are each independently of the other hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C2-C10alkoxyalkyl; and
    R140 and R141 are each independently of the other hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C1-C10alkoxyalkyl; or
    R55 and C—R140, together with the atoms to which they are bonded, form a saturated or unsaturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R142 is hydrogen, C1-C10alkyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
    R55 and N—R142, together with the atoms to which they are bonded, form a saturated or unsaturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;

and also to agronomically tolerable salts, isomers and enantiomers of those compounds.



The alkyl groups occurring in the substituent definitions may be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl and the isomers of pentyl, hexyl, heptyl, octyl, nonyl and decyl. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl or dichlorofluoromethyl. Alkoxyalkyl is, for example, methoxymethyl, ethoxymethyl, propoxyethyl, isopropoxyethyl, n-butoxymethyl, isobutoxy-n-butyl, sec-butoxymethyl and tert-butoxyisopropyl, preferably methoxymethyl and ethoxymethyl. Alkoxy, alkenyl, alkynyl, alkoxyalkyl, alkylthio, alkylsulfonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminoalkyl, phenylalkyl, nitroalkyl, aminoalkyl and N-alkoxycarbonyl-N-alkylaminoalkyl groups are derived from the mentioned alkyl radicals. The alkenyl and alkynyl groups may be mono- or poly-unsaturated. Alkenyl is to be understood as meaning, for example, vinyl, allyl, methallyl, 1-methylvinyl or but-2-en-1-yl. Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, 2-methylbutyn-2-yl or but-3-yn-2-yl. Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, 2-methylbutyn-2-yl or but-3-yn-2-yl. Haloalkyl groups preferably have a chain length of from 1 to 4 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl or 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl or dichlorofluoromethyl. Suitable haloalkenyl groups include alkenyl groups mono- or poly-substituted by halogen, halogen being fluorine, chlorine, bromine or iodine and especially fluorine or chlorine, for example 2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl, 3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl and 4,4,4-trifluorobut-2-en-1-yl. Of the C2-C6alkenyl groups mono-, di- or tri-substituted by halogen, preference is given to those having a chain length of from 3 to 5 carbon atoms. Alkoxy groups preferably have a chain length of from 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy and the isomers of pentyloxy and hexyloxy; preferably methoxy and ethoxy. Alkylcarbonyl is preferably acetyl or propionyl. Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl; preferably methoxycarbonyl or ethoxycarbonyl. Alkylthio groups preferably have a chain length of from 1 to 4 carbon atoms. Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio or ethylthio. Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl or tert-butylsulfinyl; preferably methylsulfinyl or ethylsulfinyl. Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl; preferably methylsulfonyl or ethylsulfonyl. Alkylamino is, for example, methylamino, ethylamino, n-propylamino, isopropylamino or the butylamine isomers. Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dibutylamino or diisopropylamino. Alkoxyalkyl groups preferably have from 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl. Alkylthioalkyl is, for example, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, butylthiomethyl, butylthioethyl or butylthiobutyl. Phenyl may be in substituted form. The substituents may in that case be in the ortho, meta and/or para position. Preferred substituents positions are the ortho and para positions relative to the point of attachment to the ring.
Aryl is, for example, phenyl or naphthyl. Those groups may also be substituted. When not specified otherwise in the definitions, phenyl, also as part of a substituent such as phenylalkyl, may, for example, be substituted by halogen, nitro, cyano, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfoxy, C1-C4alkylsulfonyl, carboxyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, C1-C4dialkylamino or by C1-C4alkylcarbonylamino.
Heteroaryl groups are usually aromatic heterocycles that contain preferably from 1 to 3 hetero atoms, such as nitrogen, sulfur and oxygen. Examples of suitable heterocycles and heteroaromatic compounds include: pyrrolidine, piperidine, pyran, dioxane, azetidine, oxetane, pyridine, pyrimidine, triazine, thiazole, thiadiazole, imidazole, oxazole, isoxazole and also pyrazine, furan, morpholine, piperazine, pyrazole, benzoxazole, benzthiazole, quinoxaline and quinoline. Those heterocycles and heteroaromatic compounds may be further substituted, for example by halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, nitro, cyano, thioalkyl, alkylamino or by phenyl.
Within the scope of the present invention, 3- to 7-membered cyclic groups are to be understood as meaning ring systems that, in addition to the hetero atoms that may already be present in the ring of the substituent Q, may contain, besides the carbon atoms, one or more hetero atoms, such as nitrogen, oxygen and/or sulfur. They may be saturated or unsaturated. The unsaturated bond may, for example in the group Q2, be formed by the substituents R6 and R7. Preferably, such ring systems contain from 5 to 7 ring atoms. 3- to 7-membered cyclic groups, including the cycloalkyls, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, may also be substituted. Suitable substituents include halogen, hydroxy, nitro, cyano, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkyl, C1-C4haloalkyl, keto, C2-C4alkenyloxyimino, C1-C4alkoxy, C1-C4alkoxyalkoxy, C1-C4alkylthio, or one of the following three groups:




wherein X8 is sulfur or oxygen, R28 is C1-C4alkoxy or the two R28 radicals, together with the —X8—C—X8 bridge to which they are bonded, form a 5- or 6-membered ring that may be substituted by methyl, ethyl, methoxy or by a keto group,

    R29 is C1-C4alkyl, C1-C4haloalkyl, C2-C4alkenyl or C2-C4haloalkenyl,
    R30 and R37 are each independently of the other C1-C4alkyl, phenyl or C2-C4alkenyl, or R30 and R37, together with the nitrogen atom to which they are bonded, form a 5- or 6-membered ring that may contain a hetero atom selected from nitrogen, oxygen and sulfur.


In the substituent definitions, the number of carbon atoms is the total number of carbon atoms in the alkyl, alkenyl and alkynyl groups and the groups derived therefrom, for example haloalkyl or alkenyloxy. C2-C3Alkoxyalkyl accordingly comprises methoxymethyl, methoxyethyl and ethoxymethyl. C3Alkoxycarbonylalkyl comprises methoxycarbonylethyl and ethoxycarbonylmethyl.
Alkali metal, alkaline earth metal or ammonium cations for the substituents G1 to G10 are, for example, the cations of sodium, potassium, magnesium, calcium and ammonium. Preferred sulfonium cations are especially trialkylsulfonium cations in which the alkyl groups preferably each contain from 1 to 4 carbon atoms.
Depending on the nature of the substituents, the compounds of formula I may also be in the form of geometric and/or optical isomers and mixtures of isomers as well as in the form of tautomers and mixtures of tautomers. The present invention relates also to those compounds of formula I. For example, the compounds of formula I wherein Q is Q1 and the group G1 is hydrogen may be present in the following tautomeric equilibria:




When G1 to G10 is other than hydrogen and the cyclic group formed by R4 and R5 together is asymmetrically substituted, fused or spiro-bound, for example the compound of formula I may be present in the form of an isomer of formula Id




The invention likewise includes the salts that the compounds of formula I are able to form preferably with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases. Suitable salt formers are described, for example, in WO 98/41089.
The invention likewise includes the salts that the compounds of formula I are able to form with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.
Of the alkali metal and alkaline earth metal hydroxides as salt formers, attention is drawn to the hydroxides of lithium, sodium, potassium, magnesium or calcium, but especially to those of sodium or potassium.
Examples of amines suitable for ammonium salt formation include both ammonia and also primary, secondary and tertiary C1-C18alkylamines, C1-C4hydroxyalkylamines and C2-C4alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four butylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl-ethylamine, methyl-isopropylamine, methyl-hexylamine, methyl-nonylamine, methyl-pentadecylamine, methyl-octadecylamine, ethyl-butylamine, ethyl-heptylamine, ethyl-octylamine, hexyl-heptylamine, hexyl-octylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- and p-chloroanilines; but especially triethylamine, isopropylamine and diisopropylamine.
Preferred quaternary ammonium bases suitable for the salt formation correspond, for example, to the formula [N(RaRbRcRd)]OH, wherein Ra, Rb, Rc and Rd are each independently of the others C1-C4 alkyl. Other suitable tetraalkylammonium bases having other anions can be obtained, for example, by anion exchange reactions.
Of the compounds of formula I, preference is given to those wherein Q is Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8 or Q9.
Preference is given also to compounds of formula I wherein R4 and R5 are each independently of the other C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C4-C6alkenyloxyalkyl, C4-C6alkynyloxyalkyl, C2-C6alkylthioalkyl, C2-C6alkylsulfoxylalkyl, C2-C6alkylsulfonylalkyl, C2-C6alkylcarbonylalkyl, C3-C6-N-alkoxy-iminoalkyl, C3-C6alkoxycarbonylalkyl, C1-C6aminoalkyl, C2-C6dialkylaminoalkyl, C3-C6alkylaminoalkyl, C1-C6cyanoalkyl, C4-C8cycloalkylalkyl, C7-C8phenylalkyl, C7-C8heteroarylalkyl, C7-C8phenoxyalkyl, C7-C8heteroaryloxyalkyl, C4-C6alkylideneaminooxyalkyl, C1-C6nitroalkyl, C4-C8trialkylsilylalkyl, C4-C6alkylaminocarbonyl, C3-C6dialkylaminocarbonyl, C4-C8alkylaminocarbonyloxyalkyl, C4-C8dialkylaminocarbonyloxalkyl, C4-C8alkoxycarbonylaminoalkyl, C4-C8-N-alkoxycarbonyl-N-alkylaminoalkyl, C3-C8cycloalkyl, aryl or heteroaryl, or

    R4 and R5, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group.


Preference is given also to compounds of formula I wherein

    R2, R6 and R32 are each independently of the others C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C4-C6alkenyloxyalkyl, C4-C6alkynyloxyalkyl, C2-C6alkylthioalkyl, C2-C6alkylsulfoxylalkyl, C2-C6alkylsulfonylalkyl, C3-C6alkylcarbonylalkyl, C3-C8cycloalkyl, aryl or heteroaryl;
    R7, R31 and R33 are hydrogen, C1-C6alkyl or C1-C6alkoxyalkyl;
    R8 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C4-C6alkenyloxyalkyl, C4-C6alkynyloxyalkyl, C1-C6alkylthioalkyl, C1-C6alkylsulfinylalkyl, C1-C6alkylsulfonylalkyl, C3-C8cycloalkyl, aryl or heteroaryl; or
    R6 and R7 or R2 and R31 or R32 and R33, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur, or
    R6 and R8, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R9, R10, R11 and R12 are each independently of the others C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C4-C6alkenyloxyalkyl, C4-C6alkynyloxyalkyl, C2-C6alkylthialkyl, C2-C6alkylsulfinylalkyl, C2-C6alkylsulfonylalkyl, C3-C6alkylcarbonylalkyl, C3-C8cycloalkyl, aryl or heteroaryl; or
    R9 and R11 or R9 and R10, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur, or
    R9 and R10, together with the atom to which they are bonded, form a saturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R13, R14, R34 and R35 are each independently of the others C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C4-C6alkenyloxyalkyl, C4-C6alkynyloxyalkyl, C2-C6alkylthioalkyl, C2-C6alkylsulfoxylalkyl, C2-C6alkylsulfonylalkyl, C3-C6alkylcarbonylalkyl, C3-C8cycloalkyl, aryl or heteroaryl; or
    R13 and R14 or R34 and R35, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur,
    R15 is C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C4-C6alkenyloxyalkyl, C4-C6alkynyloxyalkyl, C2-C6alkylthioalkyl, C2-C6alkylsulfoxylalkyl, C2-C6alkylsulfonylalkyl, C3-C6alkylcarbonylalkyl, C3-C6alkoxycarbonylalkyl, C2-C6aminoalkyl, C4-C6dialkylaminoalkyl, C4-C6alkylaminoalkyl, C2-C6cyanoalkyl, C3-C8cycloalkylalkyl, C7-C8phenylalkyl, C7-C8heteroarylalkyl, C7-C8phenoxyalkyl, C6-C8heteroaryloxyalkyl, C1-C6nitroalkyl, C3-C8cycloalkyl, aryl or heteroaryl;
    R16 is C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C4-C6alkenyloxyalkyl, C4-C6alkynyloxyalkyl, C2-C6alkylthiolkyl, C2-C6alkylsulfinylalkyl, C2-C6alkylsulfonylalkyl, C3-C8cycloalkyl, aryl or heteroaryl;
    R17 is C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C4-C6alkenyloxyalkyl, C4-C6alkynyloxyalkyl, C2-C6alkylthialkyl, C2-C6alkylsulfinylalkyl, C2-C6alkylsulfonylalkyl, C3-C6alkylcarbonylalkyl, C3-C8cycloalkyl, aryl or heteroaryl;
    R18 is hydrogen, C1-C6alkyl or C2-C6alkoxyalkyl; or
    R17 and R18, together with the atoms to which they are bonded, form a 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur,
    R19 and R36 are each independently of the other C1-C6alkyl, C1-C6haloalkyl, phenyl or heteroaryl; or
    R18 and R19 or R18 and R36, together with the atom to which they are bonded, form a saturated 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R20, R21, R22, R23 and R27 are each independently of the others hydrogen, C1-C8alkyl, C1-C8haloalkyl, C1-C8cyanoalkyl, C1-C8nitroalkyl, C1-C8aminoalkyl, C1-C5alkylamino-C1-C2alkyl, C2-C6dialkylamino-C1-C2alkyl, C3-C7cycloalkyl-C1-C2alkyl, C2-C8alkoxyalkyl, C4-C8alkenyloxyalkyl, C4-C8alkynyloxyalkyl, C2-C8alkylthioalkyl, C1-C2alkylsulfoxyl-C1-C2alkyl, C1-C2alkylsulfonyl-C1-C2alkyl, C2-C8alkylideneaminooxy-C1-C2alkyl, C1-C5alkylcarbonyl-C1-C2alkyl, C1-C5alkoxycarbonyl-C1-C2alkyl, C1-C5amino-carbonyl-C1-C2alkyl, C2-C8dialkylaminocarbonyl-C1-C2alkyl, C1-C5alkylcarbonylamino-C1-C2alkyl, C1-C2alkylcarbonyl-N-C1-C3alkyl-C1-C2aminoalkyl, C3-C6-trialkylsilyl-C1-C3alkyl, phenyl-C1-C2alkyl, heteroaryl-C1-C2alkyl, phenoxy-C1-C2alkyl, heteroaryloxy-C1-C2alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl or heteroaryl;
    R24, R25 and R26 are each independently of the others hydrogen, C1-C8alkyl, C1-C8haloalkyl, C1-C8cyanoalkyl, C1-C8nitroalkyl, C1-C8aminoalkyl, C1-C5alkylamino-C1-C2alkyl, C2-C6dialkylamino-C1-C2alkyl, C3-C7cycloalkyl-C1-C2alkyl, C2-C8alkoxyalkyl, C4-C8alkenyloxyalkyl, C4-C8alkynyloxyalkyl, C2-C8alkylthioalkyl, C1-C2alkylsulfoxyl-C1-C2alkyl, C1-C2alkylsulfonyl-C1-C2alkyl, C2-C8alkylideneaminooxy-C1-C2alkyl, C1-C5alkylcarbonyl-C1-C2alkyl, C1-C5alkoxycarbonyl-C1-C2alkyl, C1-C5amino-carbonyl-C1-C2alkyl, C2-C8dialkylamino-carbonyl-C1-C2alkyl, C1-C5alkylcarbonylamino-C1-C2alkyl, C1-C2alkylcarbonyl-N-C1-C3alkyl-C1-C2aminoalkyl, C3-C6trialkylsilyl-C1-C3alkyl, phenyl-C1-C2alkyl, heteroaryl-C1-C2alkyl, phenoxy-C1-C2alkyl, heteroaryloxy-C1-C2alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, heteroaryl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C3alkylamino, C2-C6dialkylamino, or benzyloxy or phenoxy in which the benzyl and phenyl groups may in turn be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro; and
    R27 is C1-C8alkyl, C1-C8haloalkyl, C1-C8cyanoalkyl, C1-C8nitroalkyl, C1-C8aminoalkyl, C1-C5alkylamino-C1-C2alkyl, C2-C6dialkylamino-C1-C2alkyl, C3-C7cycloalkyl-C1-C2alkyl, C2-C8alkoxyalkyl, C4-C8alkenyloxyalkyl, C4-C8alkynyloxyalkyl, C2-C8alkylthioalkyl, C1-C2alkylsulfoxyl-C1-C2alkyl, C1-C2alkylsulfonyl-C1-C2alkyl, C2-C8alkylideneaminooxy-C1-C2alkyl, C1-C5alkylcarbonyl-C1-C2alkyl, C1-C5alkoxycarbonyl-C1-C2alkyl, C1-C5amino-carbonyl-C1-C2alkyl, C2-C8dialkylamino-carbonyl-C1-C2alkyl, C1-C5alkylcarbonylamino-C1-C2alkyl, C1-C2alkylcarbonyl-N-C1-C3alkyl-C1-C2aminoalkyl, C3-C6trialkylsilyl-C1-C3alkyl, phenyl-C1-C2alkyl, heteroaryl-C1-C2alkyl, phenoxy-C1-C2alkyl, heteroaryloxy-C1-C2alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, heteroaryl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C8alkylcarbonyl, C1-C3alkylamino, C2-C6dialkylamino, or benzyloxy or phenoxy in which the benzyl and phenyl groups may in turn be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro.


Special preference is given to compounds of formula I wherein

    R1 and R3 are each independently of the other ethyl, haloethyl, ethynyl, C1-C2alkoxy, C1-C2haloalkoxy or C1-C2alkylcarbonyl;
    R4 and R5 are each independently of the other C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C2-C6alkylcarbonylalkyl, C3-C6alkoxycarbonylalkyl, C1-C6aminoalkyl, C2-C6dialkylaminoalkyl, C3-C6alkylaminoalkyl, C1-C6cyanoalkyl, C3-C8cycloalkyl, aryl or heteroaryl; or
    R4 and R5, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R2, R6 and R32 are each independently of the others C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C3-C8cycloalkyl, aryl or heteroaryl;
    R7, R31 and R33 are each independently of the others hydrogen, C1-C6alkyl or C1-C6alkoxyalkyl;
    R8 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C1-C6alkylthioalkyl, C3-C8cycloalkyl, aryl or heteroaryl; or
    R6 and R7 or R2 and R31 or R32 and R33, together with the atom to which they are bonded, form a saturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur; or
    R6 and R8, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R9, R10, R11 and R12 are each independently of the others C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C3-C8cycloalkyl, aryl or heteroaryl; or
    R9 and R10, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur; or
    R9 and R10, together with the atom to which they are bonded, form a saturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R13, R14, R34 and R35 are each independently of the others C1-C6alkyl, C3-C8cycloalkyl, aryl or heteroaryl; or
    R13 and R14 or R34 and R35, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R15 is C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C4-C6alkenyloxyalkyl, C2-C6alkylthioalkyl, C2-C6alkylsulfoxylalkyl, C3-C6alkoxycarbonylalkyl, C3-C8cycloalkyl, aryl or heteroaryl;
    R16 is C1-C6alkyl, C1-C6haloalkyl, C2-C6alkoxyalkyl, C3-C8cycloalkyl, aryl or heteroaryl;
    R17 is C1-C6alkyl, C1-C6haloalkyl, C3-C8cycloalkyl, aryl or heteroaryl;
    R18 is hydrogen, C1-C6alkyl or C2-C6alkoxyalkyl; or
    R17 and R18, together with the atoms to which they are bonded, form a 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R19 and R36 are each independently of the other C1-C6alkyl or C1-C6haloalkyl; or
    R18 and R19 or R18 and R36, together with the atom to which they are bonded, form a saturated 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
    R20, R21, R22 and R23 are each independently of the others hydrogen, C1-C8alkyl, C1-C8haloalkyl, C3-C7cycloalkyl-C1-C2alkyl, C2-C8alkoxyalkyl, phenyl-C1-C2alkyl, heteroaryl-C1-C2alkyl, phenoxy-C1-C2alkyl, heteroaryloxy-C1-C2alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl or heteroaryl;
    R24, R25 and R26 are each independently of the others hydrogen, C1-C8alkyl, C1-C8haloalkyl, C3-C7cycloalkyl-C1-C2alkyl, C2-C8alkoxyalkyl, phenyl-C1-C2alkyl, heteroaryl-C1-C2alkyl, phenoxy-C1-C2alkyl, heteroaryloxy-C1-C2alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, heteroaryl, C1-C6alkoxy, C1-C3alkylamino or C2-C6dialkylamino; and
    R27 is C1-C8alkyl, C1-C8haloalkyl, C3-C7cycloalkyl-C1-C2alkyl, C2-C8alkoxyalkyl, phenyl-C1-C2alkyl, heteroaryl-C1-C2alkyl, phenoxy-C1-C2alkyl, heteroaryloxy-C1-C2alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, heteroaryl, C1-C6alkoxy, C1-C3alkylamino, C2-C6dialkylamino or C1-C8alkylcarbonyl.


The compounds of formula I can be prepared by reacting a compound of formula XXX

Q-H  (XXX)

wherein Q is Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9 or Q10, the substituents of which, with the exception of G1, G2, G3, G4, G5, G6, G7, G8, G9 and G10, have the meanings given above, and G1, G2, G3, G4, G5, G6, G7, G8, G9 and G10 are hydrogen, with a compound of formula XXXI





wherein R1 and R3 are as defined for formula I and Hal is chlorine, bromine or iodine, in the presence of an inert solvent, a base and a palladium catalyst, at temperatures of from 30 to 250° C. The reaction is preferably carried out under an inert gas atmosphere.

Surprisingly, it has been shown that this process is very especially advantageous for the preparation of compounds of formula I wherein R1 and R3 are ethyl. The intermediates of formula XXXI wherein R1 and R3 are ethyl and Hal is chlorine, bromine or iodine (formula XXXIa) used for the preparation of those compounds of formula I are novel and were developed especially for that process. The present invention accordingly also relates to those intermediates.
The compounds of formula XXX are known or can be prepared according to known processes, as described, for example, in J. Chem. Soc. Perkin Trans. 1 (1987), (4), 877-884. The compounds of formula XXXI can be prepared, for example, according to known methods, via the diazonium salts, for example by Sandmeyer reaction starting from the corresponding anilines of formula XXXII




wherein R1 and R3 are as defined for formula I. Such reactions are described, for example, in Vogel's Textbook of Practical Organic Chemistry, 5th Edition, B. S. Furniss, A. J. Hannaford, P. W. G. Smith, A. R. Tatchell; Longman Scientific & Technical 1989, page 923. The compounds of formula XXXII are known; some of them are available commercially or they can be prepared analogously to known methods.

There are suitable for the reaction bases such as trialkali metal phosphates, alkali metal and alkaline earth metal hydrides, alkali metal and alkaline earth metal amides or alkali metal alcoholates, for example tripotassium phosphate, sodium hydride, lithium diisopropylamide (LDA), sodium tert-butanolate or potassium tert-butanolate. Sodium tert-butanolate, potassium tert-butanolate and tripotassium phosphate are especially preferred.
Suitable solvents include, for example, aromatic hydrocarbons, for example xylene or toluene, ethers, such as tetrahydrofuran, dioxane or ethylene glycol dimethyl ether, dimethyl sulfoxide or tertiary amides, such as dimethylformamide, N-methylpyrrolidinone or dimethyl acetamide, and acyclic ureas, such as N,N′-dimethylpropyleneurea.
Palladium catalysts that come into consideration for the C—C coupling reaction of a compound of formula XXX with a compound of formula XXXI are generally palladium(II) or palladium(0) complexes, for example palladium(II) dihalides, palladium(II) acetate, palladium(II) sulfate, bis(triphenylphosphine)palladium(II) dichloride, bis(tricyclopentylphosphine)palladium(II) dichloride, bis(tricyclohexylphosphine)palladium(II) dichloride, bis(dibenzylideneacetone)palladium(0) or tetrakis(triphenylphosphine)palladium(0). The palladium catalyst can also be prepared “in situ” from palladium(II) or palladium(0) compounds by complexing with the desired ligands, by, for example, combining the palladium(II) salt to be complexed, for example palladium(II) dichloride (PdCl2) or palladium(II) acetate (Pd(OAc)2), together with the desired ligand, for example triphenylphosphine (PPh3), tricyclopentylphosphine or tricyclohexylphosphine and the selected solvent, with a compound of formula XXXI, a compound of formula XXX and a base. Also suitable are bidendate ligands, for example 1,1′-bis(diphenylphosphino)ferrocene or 1,2-bis(diphenylphosphino)ethane. By heating the reaction medium, the palladium(II) complex or palladium(0) complex desired for the C—C coupling reaction is thus formed “in situ”, and then initiates the C—C coupling reaction.
The palladium catalysts are used in an amount of from 0.001 to 50 mol %, preferably in an amount of from 0.1 to 15 mol %, based on the compound of formula XXXI.
The reaction temperatures are selected in accordance with the solvent used and, where applicable, in accordance with the pressure. Preferably, the reaction is carried out at atmospheric pressure.
The compounds of formula I wherein Q is Q1 can be prepared analogously to the procedures described in WO 96/21652. Compounds of formula 1 wherein Q is Q2 can be prepared, for example, in accordance with the procedures described in EP-A-0 415 185, EP-A-0 521 334, EP-A-0 355 599 and EP-A-0 442 077. Compounds of formula I wherein Q is Q3, Q4, Q6 or Q7 can be prepared, for example, in accordance with the procedures described in WO 96/35644 and WO 97/02243. Compounds of formula I wherein Q is Q5 can be prepared, for example, analogously to the procedures described in WO 97/14667. Analogous procedures for the preparation of compounds of formula I wherein Q is Q7 are described in WO 97/16436. Compounds of formula I in which Q is Q8 can be prepared analogously to U.S. Pat. No. 5,994,274. Compounds of formula I wherein Q is Q9 can be prepared analogously to JP 11152273 A (priority: 19.11.1997 JP 318614), Compounds of formula I wherein Q is Q10 can be prepared according to J. Org. Chem. (1979), 44(26), 4906-4912 or J. Org. Chem. (1977), 42(7), 1163-1169 or in an analogous manner.
The reactions to form compounds of formula I are advantageously carried out in aprotic, inert organic solvents. Such solvents are hydrocarbons, such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons, such as dichloromethane, trichloromethane, tetrachloromethane or chlorobenzene, ethers, such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles, such as acetonitrile or propionitrile, and amides, such as N,N-dimethylformamide, diethylformamide or N-methylpyrrolidinone. The reaction temperatures are preferably from −20° C. to +120° C. The reactions are generally slightly exothermic and can usually be carried out at room temperature. To shorten the reaction time or also to initiate the reaction, the temperature can, if desired, be increased to the boiling point of the reaction mixture for a brief period. The reaction times can also be shortened by the addition of a few drops of base as reaction catalyst. Suitable bases include especially tertiary amines, such as trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,5-diazabicyclo[5.4.0]undec-7-ene, but it is also possible to use inorganic bases, such as hydrides, for example sodium or calcium hydride, hydroxides, for example sodium or potassium hydroxide, carbonates, for example sodium or potassium carbonate, or hydrogen carbonates, for example potassium or sodium hydrogen carbonate.
The compounds of formula I can be isolated in customary manner by concentration and/or evaporation of the solvent and can be purified by recrystallisation or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.
For the use in accordance with the invention of the compounds of formula I or of compositions comprising them, there are suitable any of the methods of application customary in agriculture, such as pre-emergence application, post-emergence application and seed dressing, and also various methods and techniques, for example the controlled release of active ingredient. In that method, the active ingredient is applied in solution to mineral granule carriers or polymerised granules (urea/formaldehyde) and dried. Where appropriate, it is also possible to apply a coating (coated granules) that allows the active ingredient to be released in metered amounts over a specific period.
The compounds of formula I can be used as herbicides in unmodified form, that is to say as obtained in the synthesis. Preferably, however, they are formulated in customary manner using the adjuvants customarily employed in formulation technology, for example into emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. Such formulations are described, for example, in WO 97/34485 on pages 9 to 13. As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
The formulations, i.e. the compositions, preparations or mixtures comprising the active ingredient of formula I or at least one active ingredient of formula I and generally one or more solid or liquid formulation adjuvants, are prepared in known manner, e.g. by intimately mixing and/or grinding the active ingredients with the formulation adjuvants, e.g. solvents or solid carriers. In addition, it is also possible for surface-active compounds (surfactants) to be used in the preparation of the formulations. Examples of solvents and solid carriers are given, for example, in WO 97/34485 on page 6.
Depending on the nature of the active ingredient of formula I to be formulated, suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants and mixtures of surfactants having good emulsifying, dispersing and welting properties. Examples of suitable anionic, non-ionic and cationic surfactants are listed, for example, on pages 7 and 8 of WO 97/34485. Also suitable for the preparation of the herbicidal compositions according to the invention are the surfactants customarily employed in formulation technology, which are described, inter alia, in “Mc Cutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch”, Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-III, Chemical Publishing Co., New York, 1980-81.
The activity of the herbicidal and plant growth-inhibiting compositions according to the invention comprising a herbicidally effective amount of compound of formula I can be increased by the addition of spray tank adjuvants.
Such adjuvants may be, for example: non-ionic surfactants, mixtures of non-ionic surfactants, mixtures of anionic surfactants with non-ionic surfactants, cationic surfactants, organosilicon surfactants, mineral oil derivatives with and without surfactants, vegetable oil derivatives with and without the addition of surfactant, alkylated derivatives of oils of vegetable or mineral origin with and without surfactants, fish oils and other animal oils of animal nature and alkyl derivatives thereof with and without surfactants, naturally occurring higher fatty acids, preferably having from 8 to 28 carbon atoms, and alkyl ester derivatives thereof, organic acids containing an aromatic ring system and one or more carboxylic acid esters, and alkyl derivatives thereof, and also suspensions of polymers of vinyl acetate or of copolymers of vinyl acetate/acrylic acid esters. Mixtures of individual adjuvants with one another and combined with organic solvents may lead to the activity being further increased.
Suitable non-ionic surfactants include, for example, polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, of saturated or unsaturated fatty acids and alkylphenols, preferably that can contain from 3 to 30 glycol ether groups and from 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and from 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.
Further suitable non-ionic surfactants are the water-soluble polyethylene oxide adducts of polypropylene glycol, ethylenediaminopolypropylene glycol and alkyl polypropylene glycol having preferably from 1 to 10 carbon atoms in the alkyl chain, which adducts contain preferably from 20 to 250 ethylene glycol ether groups and from 10 to 100 propylene glycol ether groups. The said compounds usually contain from 1 to 5 ethylene glycol units per propylene glycol unit.
There may also be mentioned, as further examples of non-ionic surfactants, nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
Fatty acid esters of polyoxyethylenesorbitan, e.g. polyoxyethylenesorbitan trioleate, are also suitable.
Preferred anionic surfactants are especially alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylated phosphoric acids, and ethoxylated derivatives thereof. The alkyl radicals usually contain from 8 to 24 carbon atoms.
Preferred non-ionic surfactants are known by the following trade names:

    polyoxyethylene cocoalkylamine (e.g. AMIET® 105 (Kao Co.)), polyoxyethylene oleylamine (e.g. AMIET® 415 (Kao Co.)), nonylphenol polyethoxyethanols, polyoxyethylene stearylamine (e.g. AMIET® 320 (Kao Co.)), N-polyethoxyethylamines (e.g. GENAMIN® (Hoechst AG)), N,N,N′,N′-tetra(polyethoxypolypropoxyethyl)ethylene-diamine (e.g. TERRONIL® and TETRONIC® (BASF Wyandotte Corp.)), BRIJ® (Atlas Chemicals), ETHYLAN® CD and ETHYLAN® D (Diamond Shamrock), GENAPOL® C, GENAPOL® O, GENAPOL® S and GENAPOL® X080 (Hoechst AG), EMULGEN® 104P, EMULGEN® 109P and EMULGEN® 408 (Kao Co.); DISTY® 125 (Geronazzo), SOPROPHOR® CY 18 (Rhone Poulenc S.A.); NONISOL® (Ciba-Geigy), MRYJ® (ICI); TWEEN® (ICI); EMULSOGEN® (Hoechst AG); AMIDOX® (Stephan Chemical Co.), ETHOMID® (Armak Co.); PLURONIC® (BASF Wyandotte Corp.), SOPROPHOR® 461 P (Rhöne Poulenc S.A.), SOPROPHOR® 496/P (Rhone Poulenc S.A.), ANTAROX FM-63 (Rhone Poulenc S.A.), SLYGARD 309 (Dow Corning), SILWET 408, SILWET L-7607N (Osi-Specialities).


The cationic surfactants are especially quaternary ammonium salts that contain as N-substituent(s) at least one alkyl radical having from 8 to 22 carbon atoms and, as further substituents, optionally halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, for example stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.
The oils used are either of mineral or natural origin. The natural oils can in addition be of animal or vegetable origin. Of the animal oils preference is given especially to derivatives of beef tallow, but fish oils (e.g. sardine oil) and derivatives thereof are also used. Vegetable oils are mostly seed oils of varied origin. Examples of vegetable oils used especially that may be mentioned include coconut oil, rapeseed oil and sunflower oil and derivatives thereof.
In the composition according to the invention, the concentrations of oil additive are generally from 0.01 to 2%, based on the spray mixture. The oil additive can, for example, be added to the spray tank in the desired concentration after the spray mixture has been prepared.
Preferred oil additives in the composition according to the invention comprise an oil of vegetable origin, for example rapeseed oil or sunflower oil, alkyl esters of oils of vegetable origin, for example methyl derivatives, or mineral oils.
Especially preferred oil additives comprise alkyl esters of higher fatty acids (C8-C22), especially the methyl derivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid. Those esters are known as methyl laurate (CAS-111-82-0), methyl palmitate (CAS-112-39-0) and methyl oleate (CAS-112-62-9).
The application and action of the oil additives can be improved by combining them with surface-active substances, such as non-ionic, anionic or cationic surfactants. Examples of suitable anionic, non-ionic and cationic surfactants are listed in WO 97/34485 on pages 7 and 8.
Preferred surface-active substances are anionic surfactants of the dodecylbenzylsulfonate type, especially the calcium salts thereof, and also non-ionic surfactants of the fatty alcohol ethoxylate type. Special preference is given to ethoxylated C12-C22 fatty alcohols having a degree of ethoxylation of from 5 to 40. Examples of commercially available preferred surfactants are the Genapol types (Clariant AG, Muttenz, Switzerland). The concentration of the surface-active substances in relation to the total additive is generally from 1 to 30% by weight.
Examples of oil additives consisting of mixtures of oils or mineral oils or derivatives thereof with surfactants include Edenor ME SU®, Emery 2231® (Henkel subsidiary Cognis GMBH, DE), Turbocharge® (Zeneca Agro, Stoney Creek, Ontario, CA) or, more especially, Actipron® (BP Oil UK Limited, GB).
The addition of an organic solvent to the oil additive/surfactant mixture can, furthermore, bring about a further increase in activity. Suitable solvents include, for example, Solvesso® (ESSO) and Aromatic Solvent® (Exxon Corporation) types.
The concentration of such solvents can be from 10 to 80%, by weight, of the total weight.
Such oil additives, which, for example, are also described in U.S. Pat. No. 4,834,908, are especially preferred for the composition according to the invention. A more especially preferred oil additive is known by the name MERGE®, can be obtained from BASF Corporation and is basically described, for example, in U.S. Pat. No. 4,834,908, col. 5, as Example COC-1. A further oil additive that is preferred in accordance with the invention is SCORE® (Novartis Crop Protection Canada).
Surfactants, oils, especially vegetable oils, derivatives thereof, such as alkylated fatty acids and mixtures thereof, for example with preferably anionic surfactants, such as alkylated phosphoric acids, alkyl sulfates and alkylaryl sulfonates and also higher fatty acids, that are customary in formulation and adjuvant technology and that can also be used in the compositions according to the invention and in spray tank solutions thereof, are described, inter alia, in “Mc Cutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood N.J., 1998, Stache, H., “Tensid-Taschenbuch”, Carl Hanser Verlag, Munich/Vienna, 1990, M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-IV, Chemical Publishing Co., New York, 1981-89, G. Kapusta, “A Compendium of Herbicide Adjuvants”, Southern Illinois Univ., 1998, L. Thomson Harvey, “A Guide to Agricultural Spray Adjuvants Used in the United States”, Thomson Pubns., 1992.
The herbicidal formulations generally contain from 0.1 to 99% by weight, especially from 0.1 to 95% by weight, of herbicide, from 1 to 99.9% by weight, especially from 5 to 99.8% by weight, of a solid or liquid formulation adjuvant, and from 0 to 25% by weight, especially from 0.1 to 25% by weight, of a surfactant. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations. The compositions may also comprise further ingredients, such as stabilisers, for example vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), anti-foams, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers and also fertilisers or other active ingredients.
The active ingredients of formula I are generally used on the plants or the locus thereof at rates of application of from 0.001 to 4 kg/ha, especially from 0.005 to 2 kg/ha. The concentration required to achieve the desired effect can be determined by experiment. It is dependent on the type of action, the development stage of the crop plant and of the weed and on the application (place, time, method) and, in dependence on those parameters, can vary within wide ranges.
The compounds of formula I are distinguished by herbicidal and growth-inhibiting properties that make them suitable for use in crops of useful plants, especially in cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, and for non-selective weed control. Crops are also to be understood as including those that have been rendered tolerant to herbicides or classes of herbicides by conventional breeding or genetic engineering methods. Those include, for example, IMI Maize, Poast Protected Maize (sethoxydim tolerance), Liberty Link Maize, B.t./Liberty Link Maize, IMI/Liberty Link Maize, IMI/Liberty Link/B.t. Maize, Roundup Ready Maize and Roundup Ready/B.t. Maize.
The weeds to be controlled may be either monocotyledonous or dicotyledonous weeds, for example Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica. 
Surprisingly, it has been shown that special safeners, known from U.S. Pat. No. 5,041,157, U.S. Pat. No. 5,541,148, U.S. Pat. No. 5,006,656, EP-A-0 094 349, EP-A-0 551 650, EP-A-0 268 554, EP-A-0 375 061, EP-A-0 174 562, EP-A-492 366, WO 91/7874, WO 94/987, DE-A-19612943, WO 96/29870, WO 98/13361, WO 98/39297, WO 98/27049, EP-A-0 716 073, EP-A-0 613 618, U.S. Pat. No. 5,597,776, EP-A-0 430 004, DE-A-4 331 448, WO 99/16744, WO 00/30447 and WO 00/00020, are suitable for mixing with the herbicidal compositions according to the invention. The present invention accordingly relates also to a selective-herbicidal composition for controlling grasses and weeds in crops of useful plants, especially in crops of maize and cereals, which composition comprises a herbicide of formula I and a safener (antidote) and protects the useful plants, but not the weeds, against the phytotoxic action of the herbicide, and to the use of such a composition in the control of weeds in crops of useful plants.
There is thus proposed, in accordance with the invention, a selective-herbicidal composition that comprises as active ingredient, in addition to customary inert formulation adjuvants, such as carriers, solvents and wetting agents, a mixture of

    a) a herbicidally effective amount of a compound of formula I






wherein R1, R3 and Q are as defined hereinabove, with the proviso that Q is other than Q1; and

    b) a herbicide-antagonistically effective amount either of a compound of formula X






wherein

    R37 is hydrogen, C1-C8alkyl, or C1-C8alkyl substituted by C1-C6alkoxy or by C3-C6alkenyloxy; and X7 is hydrogen or chlorine; or of a compound of formula XI






wherein E is nitrogen or methine;

    R38 is —CCl3, phenyl or phenyl substituted by halogen;
    R39 and R40 are each independently of the other hydrogen or halogen; and
    R41 is C1-C4alkyl; or of a compound of formula XII






wherein R44 and R45 are each independently of the other hydrogen or halogen, and R46, R47 and R48 are each independently of the others C1-C4alkyl, or of a compound of formula XIII





wherein A2 is a group





    R51 and R52 are each independently of the other hydrogen, C1-C8alkyl, C3-C8cycloalkyl, C3-C6alkenyl, C3-C6alkynyl,






or C1-C4alkyl substituted by C1-C4alkoxy or by





or R51 and R52 together form a C4-C6alkylene bridge that may be interrupted by oxygen, sulfur, SO, SO2, NH or by —N(C1-C4alkyl)-;

    R53 is hydrogen or C1-C4alkyl;
    R49 is hydrogen, halogen, cyano, trifluoromethyl, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj, —CONRkRm, —CORn, —SO2NRkRm or —OSO2-C1-C4alkyl;
    R9 is hydrogen, halogen, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj, —CONRkRm, —CORn, —SO2NRkRm, —OSO2-C1-C4alkyl, C1-C6alkoxy, or C1-C6alkoxy substituted by C1-C4alkoxy or by halogen, C3-C6alkenyloxy, or C3-C6alkenyloxy substituted by halogen, or C3-C6alkynyloxy, or R49 and R50 together form a C3-C4alkylene bridge that may be substituted by halogen or by C1-C4alkyl, or together form a C3-C4alkenylene bridge that may be substituted by halogen or by C1-C4alkyl, or together form a C4alkadienylene bridge that may be substituted by halogen or by C1-C4alkyl;
    R50 and Rh are each independently of the other hydrogen, halogen, C1-C4alkyl, trifluoromethyl, C1-C6alkoxy, C1-C6alkylthio or —COORj;
    Rc is hydrogen, halogen, nitro, C1-C4alkyl or methoxy; Rd is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm;
    Re is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy, or Rd and Re together form a C3-C4alkylene bridge;
    Rp is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy; Rq is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm; or Rp and Rq together form a C3-C4alkylene bridge;
    Rr is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy; Rs is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm; or Rr and Rs together form a C3-C4alkylene bridge;
    Rt is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy; Ru is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm; or Rv and Ru together form a C3-C4alkylene bridge;
    Rf and Rv are hydrogen, halogen or C1-C4alkyl;
    Rx and Ry are each independently of the other hydrogen, halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, —COOR54, trifluoromethyl, nitro or cyano;
    Rj, Rk and Rm are each independently of the others hydrogen or C1-C4alkyl; or
    Rk and Rm together form a C4-C6alkylene bridge that may be interrupted by oxygen, NH or by —N(C1-C4alkyl)-;
    Rn is C1-C4alkyl, phenyl, or phenyl substituted by halogen, C1-C4alkyl, methoxy, nitro or by trifluoromethyl;
    R54 is hydrogen, C1-C10alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylthio-C1-C4alkyl, di-C1-C4alkylamino-C1-C4alkyl, halo-C1-C8alkyl, C2-C8alkenyl, halo-C2-C8alkenyl, C3-C8alkynyl, C3-C7cycloalkyl, halo-C3-C7cycloalkyl, C1-C8alkylcarbonyl, allylcarbonyl, C3-C7cycloalkylcarbonyl, benzoyl, which is unsubstituted or substituted on the phenyl ring identically or differently up to three times by halogen, C1-C4alkyl, halo-C1-C4alkyl, halo-C1-C4alkoxy or C1-C4alkoxy; or furoyl, thienyl; or C1-C4alkyl substituted by phenyl, halophenyl, C1-C4alkylphenyl, C1-C4alkoxyphenyl, halo-C1-C4alkylphenyl, halo-C1-C4alkoxyphenyl, C1-C6alkoxycarbonyl, C1-C4alkoxy-C1-C8alkoxycarbonyl, C3-C8alkenyloxycarbonyl, C3-C8alkynyloxycarbonyl, C1-C8alkylthiocarbonyl, C3-C8alkenylthiocarbonyl, C3-C8alkynylthiocarbonyl, carbamoyl, mono-C1-C4alkylaminocarbonyl, di-C1-C4alkylaminocarbonyl; or phenylaminocarbonyl, which is unsubstituted or substituted on the phenyl identically or differently up to three times by halogen, C1-C4alkyl, halo-C1-C4alkyl, halo-C1-C4alkoxy or C1-C4alkoxy or once by cyano or nitro; or dioxolan-2-yl, which is unsubstituted or substituted by one or two C1-C4alkyl radicals, or dioxan-2-yl, which is unsubstituted or substituted by one or two C1-C4alkyl radicals, or C1-C4alkyl substituted by cyano, nitro, carboxyl or by C1-C8alkylthio-C1-C8alkoxycarbonyl;

or of a compound of formula XIV







wherein R56 and R57 are each independently of the other C1-C6alkyl or C2-C6alkenyl; or R56 and R57 together are





R58 and

    R59 are each independently of the other hydrogen or C1-C6alkyl; or R56 and R57 together are






    R60 and R61 are each independently of the other C1-C4alkyl, or R60 and R61 together are —(CH2)5—;
    R62 is hydrogen, C1-C4alkyl or






    or R56 and R57 together are






    R63, R64, R65, R66, R67, R68, R69, R70, R71, R72, R73, R74, R75, R76, R77 and R78 are each independently of the others hydrogen or C1-C4alkyl;

or of a compound of formula XV







    wherein R80 is hydrogen or chlorine and R79 is cyano or trifluoromethyl;

or of a compound of formula XVI







    wherein R81 is hydrogen or methyl;

or of a compound of formula XVII







wherein

    R82 is hydrogen, C1-C4alkyl, or C1-C4alkyl substituted by C1-C4alkyl-X2- or by C1-C4haloalkyl-X2-, or is C1-C4haloalkyl, nitro, cyano, —COOR85, —NR86R87, —SO2NR88R89 or —CONR90R91;
    R83 is hydrogen, halogen, C1-C4alkyl, trifluoromethyl, C1-C4alkoxy or C1-C4haloalkoxy;
    R84 is hydrogen, halogen or C1-C4alkyl;
    U, V, W1 and Z4 are each independently of the others oxygen, sulfur, C(R92)R93, carbonyl,
    NR94, or a group






wherein R102 is

    C2-C4alkenyl or C2-C4alkynyl; with the provisos that
    a) at least one of the ring members U, V, W1 or Z4 is carbonyl, and a ring member adjacent to that ring member or to those ring members is the group






that group occurring only once; and

    b) two adjacent ring members U and V, V and W1 and W1 and Z4 cannot simultaneously be oxygen;
    R95 and R96 are each independently of the other hydrogen or C1-C8alkyl; or
    R95 and R96 together form a C2-C6alkylene group;
    A1 is R99—Y1— or —NR97R98;
    X2 is oxygen or —S(O)s;
    Y1 is oxygen or sulfur;
    R99 is hydrogen, C1-C8alkyl, C1-C8haloalkyl, C1-C4alkoxy-C1-C8alkyl, C3-C6alkenyloxy-C1-C8alkyl, or phenyl-C1-C8alkyl in which the phenyl ring may be substituted by halogen, C1-C4alkyl, trifluoromethyl, methoxy or by methyl—S(O)s—, or is C3-C6alkenyl, C3-C6haloalkenyl, phenyl-C3-C6alkenyl, C3-C6alkynyl, phenyl-C3-C6alkynyl, oxetanyl, furyl or tetrahydrofuryl;
    R85 is hydrogen or C1-C4alkyl;
    R86 is hydrogen, C1-C4alkyl or C1-C4alkylcarbonyl;
    R87 is hydrogen or C1-C4alkyl; or
    R86 and R87 together form a C4- or C5-alkylene group;
    R88, R89, R90 and R91 are each independently of the others hydrogen or C1-C4alkyl; or R88 together with R89, or R90 together with R91, are each independently of the other C4- or C5-alkylene in which one carbon atom may have been replaced by oxygen or by sulfur, or one or two carbon atoms may have been replaced by —NR100—;
    R92, R100 and R93 are each independently of the others hydrogen or C1-C8alkyl; or
    R92 and R93 together are C2-C6alkylene;
    R94 is hydrogen or C1-C8alkyl;
    R97 is hydrogen, C1-C8alkyl, phenyl or phenyl-C1-C8alkyl, wherein the phenyl rings may be substituted by fluorine, chlorine, bromine, nitro, cyano, —OCH3, C1-C4alkyl or by CH3SO2—, or is C1-C4alkoxy-C1-C8alkyl, C3-C6alkenyl or C3-C6alkynyl;
    R98 is hydrogen, C1-C8alkyl, C3-C6alkenyl or C3-C6alkynyl; or
    R97 and R98 together are C4- or C5-alkylene in which one carbon atom may have been replaced by oxygen or by sulfur, or one or two carbon atoms may have been replaced by —NR101—;
    R101 is hydrogen or C1-C4alkyl;
    r is 0 or 1; and
    s is 0, 1 or 2,

or of a compound of formula XVIII







    wherein R103 is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl or C3-C6alkynyl; and R104, R105 and R106 are each independently of the others hydrogen, C1-C6alkyl, C3-C6cycloalkyl or C1-C6alkoxy, with the proviso that one of the substituents R104, R105 and R106 is other than hydrogen;

or of a compound of formula XIX







    wherein Z5 is N or CH, n is 0, 1, 2 or 3 when Z5 is N, and n is 0, 1, 2, 3 or 4 when Z5 is CH,
    R107 is halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, nitro, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkoxycarbonyl, phenyl or phenoxy, or phenyl or phenoxy substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
    R108 is hydrogen or C1-C4alkyl, R109 is hydrogen, C1-C4alkyl, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C1-C4alkylthio-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkenyloxy-C1-C4alkyl or C1-C4alkynyloxy-C1-C4alkyl;

or of a compound of formula XX







    wherein Z6 is oxygen or N—R110 and R110 is a group of formula






    wherein R111 and R112 are each independently of the other cyano, hydrogen, C1-C4alkyl, C3-C6cycloalkyl, C2-C6alkenyl, aryl, phenyl or heteroaryl, or phenyl, aryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;

or of a compound of formula XXI







    wherein Z7 is oxygen, sulfur, S═O, SO2 or CH2, R113 and R114 are each independently of the other hydrogen, halogen or C1-C4alkyl, W2 and W3 are each independently of the other CH2COOR115 or COOR0115 or together are a group of formula —(CH2)C(O)—O—C(O)—(CH2), and R115 and R0115 are each independently of the other hydrogen, C1-C4alkyl, C2-C4alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C4haloalkyl, or a metal cation or an ammonium cation;

or of a compound of formula XXII







    wherein R119 and R120 are each independently of the other hydrogen, halogen or C1-C4haloalkyl, R121 is hydrogen, C1-C4alkyl, C3-C4alkenyl, C3-C4alkynyl, C1-C4haloalkyl, C3-C6cycloalkyl, a metal cation or an ammonium cation, Z8 is N, CH, C—F or C—Cl and W4 is a group of formula






    wherein R122 and R123 are each independently of the other hydrogen or C1-C4alkyl and R124 and R125 are each independently of the other hydrogen or C1-C4alkyl;

or of a compound of formula XXIII







    wherein R126 is hydrogen, cyano, halogen, C1-C4alkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4-alkoxycarbonyl, C1-C4alkylthiocarbonyl, —NH—R128, —C(O)NH—R0128, aryl or heteroaryl, or aryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
    R127 is hydrogen, cyano, nitro, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4thioalkyl; and
    R128 and R0128 are each independently of the other C1-C4alkyl, C1-C4haloalkyl, C3-C4alkenyl, C3-C4alkynyl, C3-C4cycloalkyl, aryl or heteroaryl, or aryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, formyl, C1-C4alkylcarbonyl or C1-C4alkylsufonyl;

or of a compound of formula XXIV







    wherein R129 and R130 are each independently of the other hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, mono-C1-C8- or di-C1-C8-alkylamino, C3-C6cycloalkyl, C1-C4thioalkyl, phenyl or heteroaryl, R131 has the meanings of R129 and in addition is OH, NH2, halogen, di-C1-C4aminoalkyl, C1-C4alkylthio, C1-C4alkylsulfonyl or C1-C4alkoxycarbonyl, R132 has the meanings of R129 and in addition is cyano, nitro, carboxyl, C1-C4alkoxycarbonyl, di-C1-C4-aminoalkyl, C1-C4alkylthio, C1-C4alkylsulfonyl, SO2—OH, i-C1-C4aminoalkylsulfonyl or C1-C4-alkoxysulfonyl, R133 has the meanings of R129 and in addition is OH, NH2, halogen, di-C1-C4-aminoalkyl, pyrrolidin-1-yl, piperidin-1-yl, morpholin-1-yl, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkoxycarbonyl, phenoxy, naphthoxy, phenylamino, benzoyloxy or phenylsulfonyloxy;

or of a compound of formula XXV







    wherein R134 is hydrogen, C4alkyl, C1-C4haloalkyl, C2-C4alkenyl, C2-C4alkynyl or C1-C4alkoxy-C1-C4alkyl, R135 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4alkoxy and R136 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4alkoxy, with the proviso that R135 and R136 are not simultaneously hydrogen,

or of formula XXVI







wherein

    R143 is hydrogen, an alkali metal cation, alkaline earth metal cation, sulfonium cation or ammonium cation or ethyl;

or of formula XXVII







    wherein R144 and R145 are each independently of the other hydrogen, C1-C6alkyl, C2-C6-alkenyl, C2-C6alkynyl or C3-C6cycloalkyl;
    R146 is hydrogen, halogen, C1-C4alkyl, C1-C6haloalkyl or C1-C6haloalkoxy;
    R147 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4alkoxycarbonyl or nitro;
    n1 is 0, 1, 2 or 3; and
    m is 1 or 2;

or of formula XXVIII







wherein

    R148 is hydrogen, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylthio, C3-C8cycloalkyl, phenyl, phenyl-C1-C6alkyl or heteroaryl; wherein the said groups may be substituted by halogen, cyano, nitro, amino, hydroxy, carbonyl, carboxyl, formyl, carbonamide or by sulfonamide;
    R149 is hydrogen, C1-C6alkyl or C1-C4haloalkyl;
    each R150 is independently of any other(s) hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, cyano, nitro, formyl or carboxyl;
    R151 is hydrogen, C1-C6alkyl or C1-C4haloalkyl;
    each R152 is independently of any other(s) hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, cyano, nitro, formyl or carboxyl;
    o is 0, 1, or 2, and
    p is 0, 1 or 2;

or of formula XXIX







wherein

    R159 is hydrogen, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, phenyl-C1-6alkylcarbonyl, phenylcarbonyl, C1-6alkylsulfonyl, C1-6alkenylsulfonyl or phenylsulfonyl, wherein the afore-mentioned hydrocarbon groups may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
    R153 is hydrogen, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, C3-8cycloalkyl, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, C1-6alkylsulfonyl, C1-6alkenylsulfonyl or phenylsulfonyl, wherein the afore-mentioned hydrocarbon groups may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
    R154 is hydrogen, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, C3-8cycloalkyl, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, C1-6-alkylsulfonyl, C1-6alkenylsulfonyl or phenylsulfonyl, wherein the afore-mentioned hydrocarbon groups may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
    R155, R156, R157, and R158 are each independently of the others hydrogen, halogen, amino, C1-3alkylamino, C1-6dialkylamino, hydroxy, cyano, nitro, formyl, carboxyl, C1-6alkoxy, C1-6haloalkoxy, C1-6alkylcarbonyl, C1-6alkoxycarboxyl, C1-6alkyl, C1-6haloalkyl, C1-6alkenyl or C1-6alkynyl;
    or R153 and R158, together with the ring atoms to which they are bonded, form a five- or six-membered, partially saturated or unsaturated ring that may contain up to 2 identical or different hetero atoms from the group oxygen, sulfur and nitrogen, it being possible for that ring to be substituted by an oxo radical.


Preferably, the compositions according to the invention comprise a herbicide-antagonistically effective amount of a safener of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV or XXV.
Preferably, the selective-herbicidal composition according to the invention comprises, in herbicide-antagonistically effective amount, either a compound of formula X




    wherein R37 is hydrogen, C1-C8alkyl, or C1-C8alkyl substituted by C1-C6alkoxy or by C3-C6-alkenyloxy; and X6 is hydrogen or chlorine; or a compound of formula XI






wherein

    E is nitrogen or methine; R38 is —CCl3, phenyl, or phenyl substituted by halogen;
    R39 and R40 are each independently of the other hydrogen or halogen; and
    R41 is C1-C4alkyl; or a compound of formula XII






    wherein R44 and R45 are each independently of the other hydrogen or halogen, and R46, R47 and R48 are each independently of the others C1C4alkyl.


The above-mentioned preferences of the compounds of formula I apply also in mixtures of compounds of formula I with the safeners of formulae X to XVIII. Preferred compositions according to the invention comprise a safener selected from the group of formula Xa




Further preferred compounds of formulae X, XI and XII are also listed in Tables 9, 10 and 11.







TABLE 9







Compounds of formula X:









(X)








 









Comp. No.
X6
R37





9.01
Cl
—CH(CH3)—C5H11-n


9.02
Cl
—CH(CH3)—CH2OCH2CH═CH2


9.03
Cl
H


9.04
Cl
C4H9-n









Preferred compounds of formula XI are listed in the following Table 10.







TABLE 10







Compounds of formula XI:









(XI)








 












Comp. No.
R41
R38
R39
R40
E





10.01
CH3
phenyl
2-Cl
H
CH


10.02
CH3
phenyl
2-Cl
4-Cl
CH


10.03
CH3
phenyl
2-F
H
CH


10.04
CH3
2-chlorophenyl
2-F
H
CH


10.05
C2H5
CCl3
2-Cl
4-Cl
N


10.06
CH3
phenyl
2-Cl
4-CF3
N


10.07
CH3
phenyl
2-Cl
4-CF3
N









Preferred compounds of formula XII are listed in the following Table 11.







TABLE 11







Compounds of formula XII:









(XII)








 












Comp. No.
R46
R47
R48
R44
R45





11.01
CH3
CH3
CH3
2-Cl
4-Cl


11.02
CH3
C2H5
CH3
2-Cl
4-Cl


11.03
CH3
C2H5
C2H5
2-Cl
4-Cl









Preferred compounds of formula XIII are listed in the following Table 12 as compounds of formula XIIIa:







TABLE 12







Compounds of formula XIIIa:









(XIIIa)








 









Comp. No.
A2
R51





12.001




H


 


12.002




H


 


12.003




CH3


 


12.004




CH3









Preferred compounds of formula XIV are listed in the following Table 13:







TABLE 13







Compounds of formula XIV:









(XIV)








 










Comp.





No.
R56
R57
R56 + R57





13.001
CH2═CHCH2
CH2═CHCH2
—


 


13.002
—
—






 


13.003
—
—






 


13.004
—
—






 


13.005
—
—






 


13.006
—
—






 


13.007
—
—






 


13.008
—
—













Preferred compounds of formula XV are listed in the following Table 14:







TABLE 14







Compounds of formula XV:









(XV)








 









Comp. No.
R80
R79





14.01
H
CN


14.02
Cl
CF3









Preferred compounds of formula XVI are listed in the following Table 15:







TABLE 15







Compounds of formula XVI:









(XVI)








 








Comp. No.
R51





15.01
H


15.02
CH3









Preferred compounds of formula XVII are listed in the following Table 16 as compounds of formula XVIIa:







TABLE 16







Compounds of formula XVIIa









(XVIIa)








 











Comp.






No.
R82
Z4
V
r





16.001
H




O
1


 


16.002
H




O
1


 


16.003
H




O
1


 


16.004
H




O
1


 


16.005
H




CH2
1


 


16.006
H




CH2
1


 


16.007
H




S
1


 


16.008
H




S
1


 


16.009
H




NCH3
1


 


16.010
H




NCH3
1


 


16.011
H




NCH3
1


 


16.012
H




O
1


 


16.013
H




S
1









Preferred compounds of formula XVII are listed in the following Table 17 as compounds of formula XVIIb:







TABLE 17







Compounds of formula XVIIb









(XVIIb)








 










Comp.





No.
U
R82
Z4





17.001
O
H






 


17.002
O
H






 


17.003
O
5-Cl






 


17.004
CH2
H






 


17.005
CH2
H






 


17.006
CH2
H






 


17.007
NH
5-Cl






 


17.008
NH
5-Cl






 


17.009
NH
H






 


17.010
NH
H






 


17.011
NCH3
H






 


17.012
NCH3
H













Preferred compounds of formula XVII are listed in the following Table 18 as compounds of formula XVIIc:







TABLE 18







Compounds of formula XVIIc









(XVIIc)








 













Comp.








No.
U
V
R
W1
Z4
R82





18.001
O
C═O
1




CH2
H


 


18.002
O
C═O
1




CH2
H


 


18.003
CH2
C═O
1




CH2
H


 


18.004
CH2
C═O
1




CH2
H


 


18.005
CH2
CH2
1




C═O
H


 


18.006
CH2
CH2
1




C═O
H


 


18.007
NCH3
C═O
1




CH2
H









Preferred compounds of formula XVII are listed in the following Table 19 as compounds of formula XVIId:







TABLE 19







Compounds of formula XVIId









(XVIId)








 











Comp.





No.
R82
W1







19.001
6-Cl







 



19.002
6-Cl







 



19.003
H







 



19.004
H







 



19.005
H














Preferred compounds of formula XVIII are listed in the following Table 20:







TABLE 20







Compounds of formula XVIII









(XVIII),








 













Comp. No.
R103
R104
R105
R106







20.01
CH3
H
cyclopropyl
H



20.02
CH3
C2H5
cyclopropyl
H



20.03
CH3
cyclopropyl
C2H5
H



20.04
CH3
CH3
H
H



20.05
CH3
CH3
cyclopropyl
H



20.06
CH3
OCH3
OCH3
H



20.07
CH3
CH3
OCH3
H



20.08
CH3
OCH3
CH3
H



20.09
CH3
CH3
CH3
H



20.10
C2H5
CH3
CH3
H



20.11
C2H5
OCH3
OCH3
H



20.12
H
OCH3
OCH3
H



20.13
H
CH3
CH3
H



20.14
C2H5
H
H
CH3



20.15
H
H
H
CH3



20.16
CH3
H
H
CH3



20.17
CH3
CH3
H
CH3










Of the compounds of formula XXVIII, preference is given to those wherein

    R148 is hydrogen, C1-C6alkyl, C3-C8cycloalkyl or phenyl, wherein the said groups may be substituted by halogen, cyano, nitro, amino, hydroxy, carbonyl, carboxyl, formyl, carbonamide or sulfonamide;
    R149 is hydrogen;
    each R150 is independently of any other(s) hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, cyano, nitro or formyl;
    R151 is hydrogen; and
    each R152 is independently of any other(s) hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, cyano, nitro or formyl.


Especially preferred compounds of formula XXVIII are selected from the group

    2-methoxy-N-[4-(2-methoxybenzoylsulfamoyl)phenyl]-acetamide,
    N-[4-(2-methoxybenzoylsulfamoyl)phenyl]-cyclopropanecarboxamide,
    N-[4-(2-methoxybenzoylsulfamoyl)phenyl]-cyclobutanecarboxamide,
    N-[4-(2-chlorobenzoylsulfamoyl)phenyl]-cyclopropanecarboxamide,
    N-[4-(2-chlorobenzoylsulfamoyl)phenyl]-acetamide,
    N-[4-(2-trifluoromethoxybenzoylsulfamoyl)phenyl]-acetamide,
    N-[4-(2-trifluoromethylbenzoylsulfamoyl)phenyl]-cyclopropanecarboxamide,
    N-[4-(2-trifluoromethoxybenzoylsulfamoyl)phenyl]-cyclopropanecarboxamide,
    N-[4-(2-trifluoromethoxybenzoylsulfamoyl)phenyl]-cyclobutanecarboxamide and
    N-[4-(2-trifluoromethylbenzoylsulfamoyl)phenyl]-acetamide.


Of the compounds of formula XXIX, preference is given to those wherein

    R159 is hydrogen, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, phenyl-C1-6alkylcarbonyl or phenylcarbonyl, wherein the afore-mentioned hydrocarbon radicals may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
    R153 is hydrogen, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, formyl, C1-6alkylcarbonyl or C1-6alkoxycarbonyl, wherein the afore-mentioned hydrocarbon radicals may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
    R154 is hydrogen, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, formyl, C1-6alkylcarbonyl or C1-6alkoxycarbonyl, wherein the afore-mentioned hydrocarbon radicals may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
    R155, R156, R157 and R158 are each independently of the others hydrogen, halogen, cyano, nitro, formyl, carboxyl, C1-6alkoxy, C1-6haloalkoxy, C1-6alkylcarbonyl, C1-6alkoxycarboxyl, C1-6alkyl or C1haloalkyl;
    or R153 and R158, together with the ring atoms to which they are bonded, form a five- or six-membered, partially saturated or unsaturated ring that may contain up to 2 identical or different hetero atoms from the group oxygen, sulfur and nitrogen, it being possible for that ring to be substituted by an oxo radical.


Special preference is given to compounds of formula XXIX wherein

    R159 is hydrogen, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl,
    C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl or phenylcarbonyl;
    R153 is hydrogen, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, formyl, C1-6alkylcarbonyl or C1-6alkoxycarbonyl;
    R154 is hydrogen, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, formyl, C1-6alkylcarbonyl or C1-6alkoxycarbonyl;
    R155, R156, R157, and R158 are each independently of the others hydrogen, halogen, cyano, nitro, formyl, C1-6alkyl, C1-6haloalkyl, C1-6alkoxy or C1-6haloalkoxy;
    or R153 and R158, together with the ring atoms to which they are bonded, form a five- or six-membered, partially saturated or unsaturated ring that may contain up to 2 identical or different hetero atoms from the group oxygen, sulfur and nitrogen, it being possible for that ring to be substituted by an oxo radical.


Very special preference is given to compounds of formula XXIX selected from the group

    4-hydroxy-1-methyl-3-(1H-tetrazole-5-carbonyl)-1H-quinolin-2-one,
    1-ethyl-4-hydroxy-3-(1H-tetrazole-5-carbonyl)-1H-quinolin-2-one,
    6-hydroxy-5-(1H-tetrazole-5-carbonyl)-1,2-dihydro-pyrrolo[3.2.1-.ij.]quinolin4-one,
    3-(1-acetyl-1H-tetrazole-5-carbonyl)-4-hydroxy-1-methyl-1H-quinolin-2-one,
    6-chloro-4-hydroxy-1-methyl-3-(1H-tetrazole-5-carbonyl)-1H-quinolin-2-one,
    6-fluoro-4-hydroxy-1-methyl-3-(1H-tetrazole-5-carbonyl)-1H-quinolin-2-one,
    4-hydroxy-1,6-dimethyl-3-(1H-tetrazole-5-carbonyl)-1H-quinolin-2-one,
    4-hydroxy-6-methoxy-1-methyl-3-(1H-tetrazole-5-carbonyl)-1H-quinolin-2-one,
    4-hydroxy-6-methoxy-1-methyl-3-(1H-tetrazole-5-carbonyl)-1H-quinolin-2-one,
    acetic acid 1-methyl-2-oxo-3-(1H-tetrazole-5-carbonyl)-1,2-dihydro-quinolin4-yl ester and
    2,2-dimethylpropionic acid 1-methyl-2-oxo-3-(1H-tetrazole-5-carbonyl)-1,2-dihydroquinolin-4-yl ester.


The invention relates also to a method for the selective control of weeds in crops of useful plants, which comprises treating the useful plants, the seeds or cuttings thereof or the area of cultivation thereof simultaneously or separately with a herbicidally effective amount of a herbicide of formula I and a herbicide-antagonistically effective amount of a safener of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX, preferably of formula X, XI, XII, XIII, XIV, XV, XVI, XVII or XVIII.
Suitable cultivated plants that can be protected against the harmful effect of the above-mentioned herbicides by the safeners of formula X, XI, XII, XIII, XIV, XV, XVI, XVII or XVIII are especially cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, more especially maize and cereals. Crops are also to be understood as including those that have been rendered tolerant to herbicides or classes of herbicides by conventional breeding or genetic engineering methods.
The weeds to be controlled may be either monocotyledonous or dicotyledonous weeds, for example the monocotyledonous weeds Avena, Agrostis, Phalaris, Lolium, Bromus, Alopecurus, Setaria, Digitara, Brachiaria, Echinochloa, Panicum, Sorghum hal./bic., Rottboellia, Cyperus, Brachiaria, Echinochloa, Scirpus, Monochoria, Sagittaria and Stellaria and the dicotyledenous weeds Sinapis, Chenopodium, Galium, Viola, Veronica, Matricaria, Papaver, Solanum, Abutilon, Sida, Xanthium, Amaranthus, Ipomoea and Chrysanthemum. 
Areas of cultivation are areas of land on which the cultivated plants are already growing or in which the seeds of those cultivated plants have already been sown, as well as the areas of land on which it is intended to grow those cultivated plants.
A safener of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX may, depending on the intended purpose, be used to pretreat the seed material of the cultivated plant (dressing the seed or the cuttings) or may be incorporated into the soil before or after sowing. It can, however, also be applied alone or together with the herbicide after the emergence of the plants. The treatment of the plants or seed with the safener can therefore, in principle, be effected independently of the time at which the herbicide is applied. The treatment of the plants can, however, also be carried out by applying the herbicide and safener simultaneously (for example in the form of a tank mixture). The rate of application of the safener in relation to the herbicide depends largely on the method of application. In the case of field treatment, which is effected either using a tank mixture comprising a combination of safener and herbicide or by the separate application of safener and herbicide, the ratio of herbicide to safener is generally from 100:1 to 1:10, preferably from 20:1 to 1:1. In the case of field treatment, from 0.001 to 1.0 kg of safener/ha, preferably from 0.001 to 0.25 kg of safener/ha, is generally applied.
The rate of application of herbicide is generally from 0.001 to 2 kg/ha, but is preferably from 0.005 to 0.5 kg/ha.
The compositions according to the invention are suitable for any of the methods of application customary in agriculture, for example pre-emergence application, post-emergence application and seed dressing.
In the case of seed dressing, from 0.001 to 10 g of safener/kg of seed, preferably from 0.05 to 2 g of safener/kg of seed, is generally applied. When the safener is applied in liquid form shortly before sowing, with swelling of the seed, it is advantageous to use safener solutions that comprise the active ingredient in a concentration of from 1 to 10 000 ppm, preferably from 100 to 1000 ppm.
For application, the safeners of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX, or combinations of those safeners with the herbicides of formula I, are advantageously processed, together with the adjuvants customary in formulation technology, into formulations, for example into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
Such formulations are described, for example, in WO 97/34485, on pages 9 to 13. The formulations are prepared in known manner, e.g. by intimately mixing and/or grinding the active ingredients with liquid or solid formulation adjuvants, for example solvents or solid carriers. Furthermore, in addition surface-active compounds (surfactants) can be used in the preparation of the formulations. Solvents and solid carriers suitable for that purpose are mentioned, for example, in WO 97/34485, on page 6.
Depending on the nature of the active ingredient of formula I to be formulated, there come into consideration as surface-active compounds non-ionic, cationic and/or anionic surfactants and mixtures of surfactants having good emulsifiying, dispersing and wetting properties. Examples of suitable anionic, non-ionic and cationic surfactants are listed, for example, in WO 97/34485 on pages 7 and 8. Also suitable for the preparation of the herbicidal compositions according to the invention are the surfactants customarily employed in formulation technology, which are described, inter alia, in “Mc Cutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch”, Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-III, Chemical Publishing Co., New York, 1980-81.
The herbicidal formulations generally contain from 0.1 to 99% by weight, especially from 0.1 to 95% by weight, of active ingredient mixture comprising the compound of formula I and the compounds of formulae X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX, from 1 to 99.9% by weight of a solid or liquid formulation adjuvant and from 0 to 25% by weight, especially from 0.1 to 25% by weight, of a surfactant. Whereas commercial products will usually preferably be formulated as concentrates, the end user will normally employ dilute formulations.
The compositions may also comprise further additives, such as stabilisers, vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), anti-foams, e.g. silicone oil, preservatives, viscosity regulators, binders, tackifiers and also fertilisers or other active ingredients. There are various suitable methods and techniques for using safeners of formulae X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX or compositions comprising them to protect cultivated plants against the harmful effects of herbicides of formula I; the following are examples:
i) Seed Dressing
a) Dressing the seeds with a wettable powder formulation of an active ingredient of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX, by shaking in a vessel until the formulation is uniformly distributed on the seed surface (dry dressing). Approximately from 1 to 500 g of active ingredient of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX (from 4 g to 2 kg of wettable powder) are used per 100 kg of seed.
b) Dressing the seeds with an emulsifiable concentrate of an active ingredient of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX in accordance with method a) (wet dressing).
c) Dressing by immersing the seeds in a liquid formulation containing from 100 to 1000 ppm of active ingredient of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX for from 1 to 72 hours and, if desired, subsequently drying the seeds (immersion dressing).
Dressing the seeds or treating the germinated seedlings are naturally the preferred methods of application, because treatment with the active ingredient is directed wholly at the target crop. From 1 to 1000 g of antidote, preferably from 5 to 250 g of antidote, is generally used per 100 kg of seed, although depending on the method employed, which also allows the addition of other active ingredients or micronutrients, amounts that exceed or fall short of the specified concentration limits may be employed (repeat dressing).
ii) Application in the Form of a Tank Mixture
A liquid formulation of a mixture of antidote and herbicide (ratio of the one to the other from 10:1 to 1:100) is used, the rate of application of herbicide being from 0.005 to 5.0 kg per hectare. Such tank mixtures are applied before or after sowing.
iii) Application to the Seed Furrow
The active ingredient of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX is introduced into the open, sown seed furrow in the form of an emulsifiable concentrate, wettable powder or granules. After the seed furrow has been covered, the herbicide is applied pre-emergence in the normal manner.
iv) Controlled Active Ingredient Release
The active ingredient of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX is applied in solution to mineral granule carriers or polymerised granules (urea/formaldehyde) and dried. Where appropriate, it is also possible to apply a coating (coated granules) that allows the active ingredient to be released in metered amounts over a specific period.
The activity of herbicidal and plant growth-inhibiting compositions according to the invention comprising a herbicidally effective amount of compound of formula I and a herbicide-antagonistically effective amount of compound of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX can be increased by the addition of spray tank adjuvants.
Such adjuvants may be, for example: non-ionic surfactants, mixtures of non-ionic surfactants, mixtures of anionic surfactants with non-ionic surfactants, cationic surfactants, organosilicon surfactants, mineral oil derivatives with and without surfactants, vegetable oil derivatives with and without the addition of surfactant, alkylated derivatives of oils of vegetable or mineral origin with and without surfactants, fish oils and other animal oils of animal nature and alkyl derivatives thereof with and without surfactants, naturally occurring higher fatty acids, preferably having from 8 to 28 carbon atoms, and alkyl ester derivatives thereof, organic acids containing an aromatic ring system and one or more carboxylic acid esters, and alkyl derivatives thereof, and also suspensions of polymers of vinyl acetate or copolymers of vinyl acetate/acrylic acid esters. Mixtures of individual adjuvants with one another and combined with organic solvents may lead to the activity being further increased.
Suitable non-ionic surfactants include, for example, polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, of saturated or unsaturated fatty acids and alkylphenols, preferably that can contain from 3 to 30 glycol ether groups and from 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and from 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.
Further suitable non-ionic surfactants are the water-soluble polyethylene oxide adducts of polypropylene glycol, ethylenediaminopolypropylene glycol and alkyl polypropylene glycol having preferably from 1 to 10 carbon atoms in the alkyl chain, which adducts contain preferably from 20 to 250 ethylene glycol ether groups and from 10 to 100 propylene glycol ether groups. The said compounds usually contain from 1 to 5 ethylene glycol units per propylene glycol unit.
There may also be mentioned, as further examples of non-ionic surfactants, nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxy ethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
Fatty acid esters of polyoxyethylenesorbitan, e.g. polyoxyethylenesorbitan trioleate, are also suitable.
Preferred anionic surfactants are especially alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylated phosphoric acids, and ethoxylated derivatives thereof. The alkyl radicals usually contain from 8 to 24 carbon atoms.
Preferred non-ionic surfactants are known by the following trade names:

    polyoxyethylene cocoalkylamine (e.g. AMIET® 105 (Kao Co.)), polyoxyethylene oleylamine (e.g. AMIET® 415 (Kao Co.)), nonylphenol polyethoxyethanols, polyoxyethylene stearylamine (e.g. AMIET® 320 (Kao Co.)), N-polyethoxyethylamines (e.g. GENAMIN® (Hoechst AG)), N,N,N′,N′-tetra(polyethoxypolypropoxyethyl)ethylene-diamine (e.g. TERRONIL® and TETRONIC®(BASF Wyandotte Corp.)), BRIJ® (Atlas Chemicals), ETHYLAN® CD and ETHYLAN® D (Diamond Shamrock), GENAPOL® C, GENAPOL® O, GENAPOL® S and GENAPOL® X080 (Hoechst AG), EMULGEN® 104P, EMULGEN® 109P and EMULGEN® 408 (Kao Co.); DISTY® 125 (Geronazzo), SOPROPHOR® CY 18 (Rhone Poulenc S.A.); NONISOL® (Ciba-Geigy), MRYJ® (ICI); TWEEN® (ICI); EMULSOGEN® (Hoechst AG); AMIDOX® (Stephan Chemical Co.), ETHOMID® (Armak Co.); PLURONIC® (BASF Wyandotte Corp.), SOPROPHOR® 461 P (Rhöne Poulenc S.A.), SOPROPHOR® 496/P (Rhone Poulenc S.A.), ANTAROX FM-63 (Rhone Poulenc S.A.), SLYGARD 309 (Dow Corning), SILWET 408, SILWET L-7607N (Osi-Specialities).


The cationic surfactants are especially quaternary ammonium salts that contain as N-substituent(s) at least one alkyl radical having from 8 to 22 carbon atoms and, as further substituents, optionally halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, for example stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.
The oils used are either of mineral or natural origin. The natural oils can in addition be of animal or vegetable origin. Of the animal oils preference is given especially to derivatives of beef tallow, but fish oils (e.g. sardine oil) and derivatives thereof are also used. Vegetable oils are mostly seed oils of varied origin. Examples of vegetable oils used especially that may be mentioned include coconut oil, rapeseed oil and sunflower oil and derivatives thereof.
In the composition according to the invention, the concentrations of oil additive are generally from 0.01 to 2% based on the spray mixture. The oil additive can, for example, be added to the spray tank in the desired concentration after the spray mixture has been prepared.
Preferred oil additives in the composition according to the invention comprise an oil of vegetable origin, for example rapeseed oil or sunflower oil, alkyl esters of oils of vegetable origin, for example methyl derivatives, or mineral oils.
Especially preferred oil additives comprise alkyl esters of higher fatty acids (C8-C22), especially methyl derivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid. Those esters are known as methyl laurate (CAS-111-82-0), methyl palmitate (CAS-112-39-0) and methyl oleate (CAS-112-62-9).
The application and action of the oil additives can be improved by combining them with surface-active substances, such as non-ionic, anionic or cationic surfactants. Examples of suitable anionic, non-ionic and cationic surfactants are listed in WO 97/34485 on pages 7 and 8.
Preferred surface-active substances are anionic surfactants of the dodecylbenzylsulfonate type, especially the calcium salts thereof, and also non-ionic surfactants of the fatty alcohol ethoxylate type. Special preference is given to ethoxylated C12-C22 fatty alcohols having a degree of ethoxylation of from 5 to 40. Examples of commercially available preferred surfactants are the Genapol types (Clariant AG, Muttenz, Switzerland).
The concentration of the surface-active substances in relation to the total additive is generally from 1 to 30% by weight.
Examples of oil additives that consist of mixtures of oils or mineral oils, or derivatives thereof, with surfactants include Edenor ME SU®, Emery 2231® (Henkel subsidiary Cognis GMBH, DE), Turbocharge® (Zeneca Agro, Stoney Creek, Ontario, CA) or, more especially, Actipron® (BP Oil UK Limited, GB).
The addition of an organic solvent to the oil additive/surfactant mixture can also bring about further increase in activity. Suitable solvents include, for example, Solvesso® (ESSO) and Aromatic Solvent® (Exxon Corporation) types.
The concentration of such solvents can be from 10 to 80%, by weight, of the total weight.
Such oil additives, which, for example, are also described in U.S. Pat. No. 4,834,908, are especially preferred for the composition according to the invention. A more especially preferred oil additive is known by the name MERGE®, can be obtained from BASF Corporation and is basically described, for example, in U.S. Pat. No. 4,834,908, col. 5, as Example COC-1. A further oil additive that is preferred in accordance with the invention is SCORE® (Novartis Crop Protection Canada).
Surfactants, oils, especially vegetable oils, derivatives thereof, such as alkylated fatty acids and mixtures thereof, for example with preferably anionic surfactants, such as alkylated phosphoric acids, alkyl sulfates and alkylaryl sulfonates and also higher fatty acids, that are customary in formulation and adjuvant technology and that can also be used in the compositions according to the invention and in spray tank solutions thereof, are described, inter alia, in “McCutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood N.J., 1998, Stache, H., “Tensid-Taschenbuch”, Carl Hanser Verlag, Munich/Vienna, 1990, M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-IV, Chemical Publishing Co., New York, 1981-89, G. Kapusta, “A Compendium of Herbicide Adjuvants”, Southern Illinois Univ., 1998, L. Thomson Harvey, “A Guide to Agricultural Spray Adjuvants Used in the United States”, Thomson Pubns., 1992.
Preferred formulations have especially the following compositions (%=percent by weight)













Emulsifiable



concentrates:


active ingredient mixture:
from 1 to 90%, preferably from 5 to 20%


surface-active agent:
from 1 to 30%, preferably from 10 to 20%


liquid carrier:
from 5 to 94%, preferably from 70 to 85%


Dusts:


active ingredient mixture:
from 0.1 to 10%, preferably from 0.1 to 5%


solid carrier:
from 99.9 to 90%, preferably from 99.9 to 99%


Suspension concentrates:


active ingredient mixture:
from 5 to 75%, preferably from 10 to 50%


water:
from 94 to 24%, preferably from 88 to 30%


surface-active agent:
from 1 to 40%, preferably from 2 to 30%


Wettable powders:


active ingredient mixture:
from 0.5 to 90%, preferably from 1 to 80%


surface-active agent:
from 0.5 to 20%, preferably from 1 to 15%


solid carrier:
from 5 to 95%, preferably from 15 to 90%


Granules:


active ingredient mixture:
from 0.1 to 30%, preferably from 0.1 to 15%


solid carrier:
from 99.5 to 70%, preferably from 97 to 85%









The Examples that follow illustrate the invention further. They do not limit the invention.
Formulation Examples for Mixtures of Herbicides of Formula I and Safener of Formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX (%=Percent by Weight)














F1. Emulsifiable concentrates
a)
b)
c)
d)







active ingredient mixture
5%
10% 
25%
50%


calcium dodecylbenzenesulfonate
6%
8%
 6%
 8%


castor oil polyglycol ether
4%
—
 4%
 4%


(36 mol of ethylene oxide)


octylphenol polyglycol ether
—
4%
—
 2%


(7-8 mol of ethylene oxide)


cyclohexanone
—
—
10%
20%


aromatic C9-C12 hydrocarbon mixture
85% 
78% 
55%
16%









Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
















a)
b)
c)
d)




















F2. Solutions






active ingredient mixture
 5%
10%
50%
90%


1-methoxy-3-(3-methoxy-
—
20%
20%
—


propoxy)-propane


polyethylene glycol (mol. wt. 400)
20%
10%
—
—


N-methyl-2-pyrrolidone
—
—
30%
10%


aromatic C9-C12 hydrocarbon mixture
75%
60%
—
—







The solutions are suitable for application in the form of micro-drops.











F3. Wettable powders






active ingredient mixture
 5%
25%
50%
80%


sodium lignosulfonate
 4%
—
 3%
—


sodium lauryl sulfate
 2%
 3%
—
 4%


sodium diisobutylnaphthalenesulfonate
—
 6%
 5%
 6%


octylphenol polyglycol ether
—
 1%
 2%
—


(7-8 mol of ethylene oxide)


highly dispersed silicic acid
 1%
 3%
 5%
10%


kaolin
88%
62%
35%
—









The active ingredient is mixed thoroughly with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of any desired concentration.
















F4. Coated granules
a)
b)
c)









active ingredient mixture
 0.1%
 5%
15%



highly dispersed silicic acid
 0.9%
 2%
 2%



inorganic carrier material
99.0%
93%
83%



(  0.1-1 mm)



for example CaCO3 or SiO2










The active ingredient is dissolved in methylene chloride, the solution is sprayed onto the carrier, and the solvent is subsequently evaporated off in vacuo.
















F5. Coated granules
a)
b)
c)









active ingredient mixture
 0.1%
 5%
15%



polyethylene glycol (mol. wt. 200)
 1.0%
 2%
 3%



highly dispersed silicic acid
 0.9%
 1%
 2%



inorganic carrier material
98.0%
92%
80%



(  0.1-1 mm)



for example CaCO3 or SiO2










The finely ground active ingredient is uniformly applied, in a mixer, to the carrier material moistened with polyethylene glycol, yielding non-dusty coated granules.

















F6. Extruder granules
a)
b)
c)
d)









active ingredient mixture
 0.1%
 3%
 5%
15%



sodium lignosulfonate
 1.5%
 2%
 3%
 4%



carboxymethylcellulose
 1.4%
 2%
 2%
 2%



kaolin
97.0%
93%
90%
79%










The active ingredient is mixed with the adjuvants, and the mixture is ground, moistened with water, extruded and then dried in a stream of air.
















F7. Dusts
a)
b)
c)









active ingredient mixture
 0.1%
 1%
 5%



talcum
39.9%
49%
35%



kaolin
60.0%
50%
60%










Ready-to-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture in a suitable mill.














F8. Suspension concentrates
a)
b)
c)
d)







active ingredient mixture
  3%
 10%
 25%
 50%


ethylene glycol
  5%
  5%
  5%
  5%


nonylphenol polyglycol ether
—
  1%
  2%
—


(15 mol of ethylene oxide)


sodium lignosulfonate
  3%
  3%
  4%
  5%


carboxymethylcellulose
  1%
  1%
  1%
  1%


37% aqueous formaldehyde solution
0.2%
0.2%
0.2%
0.2%


silicone oil emulsion
0.8%
0.8%
0.8%
0.8%


water
 87%
 79%
 62%
 38%









The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.
It is often more practical to formulate the active ingredient of formula I and the mixing partner of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX separately and then, shortly before application, to bring them together in the applicator in the desired mixing ratio in the form of a “tank mixture” in water.
The ability of the safeners of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX to protect cultivated plants against the phytotoxic action of herbicides of formula I is illustrated in the following Examples.


BIOLOGICAL EXAMPLE 1
Safening Action
Under greenhouse conditions, the test plants are grown in plastics pots to the 4-leaf stage. At that stage, on the one hand the herbicide alone, and on the other hand mixtures of the herbicide with the test substances to be tested as safeners, are applied to the test plants. The test substances are applied in the form of an aqueous suspension prepared from a 25% wettable powder (Example F3, b)), using 500 liters of water/ha. 2 to 3 weeks after application, the phytotoxic action of the herbicide on the cultivated plants, for example maize and cereals, is evaluated using a percentage scale. 100% indicates that the test plant has died, and 0% indicates no phytotoxic action.
The results obtained in this test demonstrate that the damage caused to the cultivated plant by the herbicide of formula I can be appreciably reduced by the compounds of formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV, XXV, XXVI, XXVII, XXVIII or XXIX. Examples of those results are given in the following Table B5:







TABLE B5







Post-emergence action of a mixture according to the invention of


herbicide and safener:










Comp.
Comp. No. 1.01 (60 g/ha) + Comp.


Test plant
No. 1.01 (60 g/ha)
No. 11.03 (15 g/ha)












Barley
20
0


Agrostis
70
70


Alopecurus
70
80


Lolium
70
70









It can be seen from Table 5 that compound No. 1.01 exhibits a phytotoxic effect of 20% on barley, which is not tolerable. The weeds Agrostis, Alopecurus und Lolium are satisfactorily controlled.
In contrast, the mixture according to the invention, consisting of herbicide No. 1.01 and safener No. 11.03, has no phytotoxic effect on the cultivated plant. At the same time, the herbicidal effect on the weeds is not only identical but surprisingly, in the case of Alopecurus, even increased (80% compared with the 70% achieved with the application of herbicide No. 1.01 on its own).
The same results are obtained when the mixtures are formulated in accordance with Examples F1, F2 and F4 to F8.
The compound of formula I can advantageously be mixed with a number of other known herbicides. As a result, for example, the spectrum of weeds is substantially broadened and in many cases an increase in selectivity with respect to the useful plants is achieved. In particular, mixtures of the compound of formula I with at least one of the following herbicides are important:

    herbicides from the class of the phenoxy-phenoxypropionic acids, for example diclofop-methyl, fluazifop-P-butyl, quizalafop-P-ethyl, propaquizafop, clodinafop-P-propargyl, cyhalfop-butyl, fenoxaprop-P-ethyl, haloxyfop-methyl or haloxyfop-etoethyl;
    herbicides from the class of the hydroxylamines, for example sethoxidim, alloxydim, clethodim, cycloxydim, tepralkoxydim, tralkoxydim or butroxidim;
    herbicides from the class of the sulfonylureas, for example amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, cinosulfuron, chlorsulfuron, chlorimuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, fluazasulfuron, flupyrsulfuron, imazosulfuron, iodosulfuron (CAS RN 144550-36-7 and 185119-76-0), metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, pyrazosulfuron-ethyl, sulfosulfuron, rimsulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triflusulfuron-methyl, prosulfuron, flucarbazone or tritosulfuron (CAS RN 142469-14-5);
    herbicides from the class of the imidazolinones, such as imazethapyr, imazamethabenz, imazamethapyr, imazaquin, imazamox or imazapyr;
    herbicides from the class of the pyrimidines, such as pyrithiobac-sodium, pyriminobac, bispyribac-sodium;
    herbicides from the class of the triazines, for example atrazine, simazine, simethryne, terbutryne, terbuthylazine;
    herbicides from the class of the ureas, such as isoproturon, chlortoluron, diuron, dymron, fluometuron, linuron or methabenzthiazuron;
    herbicides from the class of the phosphonic acid derivatives, for example glyphosate, glufosinate, sulfosate or phosphinothricin;
    herbicides from the class of the PPO, for example nitrofen, bifenox, acifluorfen, lactofen, oxyfluorfen, ethoxyfen, fluoroglycofen, fomesafen, halosafen, azafenidin (CAS RN.-68049-83-2), benzfendizone (CAS RN 158755-954), butafenacil (known from U.S. Pat. No. 5,183,492, CAS RN 158755-95-4), carfentrazone-ethyl, cinidon-ethyl (CAS RN 142891-20-1), flumichlorac-pentyl, flumioxazin, fluthiacet-methyl, oxadiargyl, oxadiazon, pentoxazone, sulfentrazone, fluazolate (CAS RN 174514-07-9) or pyraflufen-ethyl;
    herbicides from the class of the chloroacetanilides, for example alachlor, acetochlor, butachlor, dimethachlor, dimethenamid, S-dimethenamid, metazachlor, metolachlor, S-metolachlor, pretilachlor, propachlor, propisochlor, thenylchlor or pethoamid (CASRN 106700-29-2)
    herbicides from the class of the phenoxyacetic acids, for example 2,4-D, fluroxypyr, MCPA, MCPP, MCPB, trichlorpyr or mecropop-P;
    herbicides from the class of the triazinones, for example hexazinone, metamitron or metribuzin;
    herbicides from the class of the dinitroanilines, for example oryzalin, pendimethalin or trifluralin;
    herbicides from the class of the azinones, for example chloridazon or norflurazon;
    herbicides from the class of the carbamates, for example chlorpropham, desmedipham, phenmedipham or propham;
    herbicides from the class of the oxyacetamides, for example mefenacet or fluthiacet;
    herbicides from the class of the thiolcarbamates, for example butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb or triallate;
    herbicides from the class of the azoloureas, for example fentrazamide (CAS RN158237-07-1) or cafenstrole;
    herbicides from the class of the benzoic acids, for example dicamba or picloram;
    herbicides from the class of the anilides, for example diflufenican, or propanil;
    herbicides from the class of the nitriles, for example bromoxynil, dichlobenil or ioxynil;
    herbicides from the class of the triones, for example sulcotrione, mesotrione (known from U.S. Pat. No. 5,006,158), isoxaflutole or isoxachlortole;
    herbicides from the class of the sulfonamides, for example flucarbazone (CAS RN 181274-17-9), procarbazone (CAS RN 145026-81-9), chlorasulam, diclosulam (CAS RN 145701-21-9), florasulam, flumetsulam or metosulam;
    and also amitrole, benfuresate, bentazone, cinmethylin, clomazone, chlopyralid, difenzoquat, dithiopyr, ethofumesate, flurochloridone, indanofan, isoxaben, oxaziclomefone, pyridate, pyridafol (CAS RN. 40020-01-7), quinchlorac, quinmerac, tridiphane or flamprop.


Unless specificed otherwise, the above-mentioned mixing partners of the compound of formula I are known from The Pesticide Manual, Eleventh Edition, 1997, BCPC. The mixing partners of the compound of formula I can, if desired, also be in the form of esters or salts, as mentioned, for example, in The Pesticide Manual, Eleventh Edition, 1997, BCPC.
The following Examples illustrate the invention further without implying any limitation.
PREPARATION EXAMPLES
Example P1
Preparation of




To a solution of 20 g of 2-(2,6-dibromo-4-methyl-phenyl)-malonic acid dimethyl ester (52.6 mmol) in 400 ml of toluene (degassed 3 times, vacuum/argon) there are added first 36.7 g (0.116 mol) of tributylvinylstannane and then 2 g of tetrakis(triphenylphosphine)-palladium. The reaction mixture is then stirred for 9 hours at a temperature of from 90 to 95° C. After filtration over Hyflo and concentration using a rotary evaporator, and after purification by chromatography, 15.3 g of (8) are obtained in the form of a yellow oil, which is used in the next reaction without being further purified.
Example P2




15.2 g of compound (8) obtained according to Example P1 are hydrogenated with hydrogen over a palladium catalyst (carbon as carrier, 7 g of 5% Pd/C) in 160 ml of tetrahydrofuran at a temperature of from 20 to 25° C. When the hydrogenation is complete, the product is filtered over Hyflo and the filtrate obtained is concentrated using a rotary evaporator. 13.7 g of (9) are obtained in the form of yellow crystals having a melting point of from 47 to 49° C.
Example P3




71.8 g (0.71 mol) of triethylamine are added to a suspension of 40 g (0.15 mol) of (4) in 1000 ml of xylene and the mixture is degassed (4 times, vacuum/argon). The yellow suspension is then heated to a temperature of 60° C. and stirred for 3 hours. 42.5 g (0.15 mol) of (5) are subsequently added and the mixture is heated to a bath temperature of 150° C. in order continuously to distill off excess triethylamine and the resulting ethanol. After 3 hours, the reaction mixture is cooled to a temperature of 40° C. and introduced into 500 ml of an ice/water mixture. The reaction mixture is rendered alkaline using 100 ml of aqueous 1N sodium hydroxide solution, and the aqueous phase (containing the product) is washed twice with ethyl acetate. After then washing the organic phase twice with aqueous 1N sodium hydroxide solution, the aqueous phases are combined, the remaining xylene is distilled off and the combined aqueous phases are adjusted to pH 2-3 using 4N HCl with cooling. The precipitated product obtained is poured onto a suction filter, and the filtration residue is washed with water and briefly with hexane, and then dried in vacuo at a temperature of 60° C. over P2O5. 34.6 g of (6) are obtained in the form of a slightly beige solid having a melting point of from 242 to 244° C. (decomposition).
Example P4




A catalytic amount of 4-dimethylaminopyridine is added to a solution, cooled to a temperature of 0° C., of 3 g (10.4 mmol) of (6) and 1.6 g (15.8 mmol) of triethylamine in 100 ml of tetrahydrofuran. 1.57 g (13.0 mmol) of pivaloyl chloride is then added dropwise. After stirring for 30 minutes at a temperature of 0° C., the cooling is removed and the stirring is continued for a further 60 minutes. The reaction mixture is then introduced into saturated aqueous sodium chloride solution and the organic phase is separated off. The organic phase is dried over magnesium sulfate, filtered off and concentrated by evaporation. After purification by chromatography and recrystallisation from diethyl ether, 2.94 g of (7) having a melting point of from 135 to 136° C. are obtained.
Example P5
Preparation of 2-(2,6-diethyl-4-methyl-phenyl)-tetrahydro-pyrazolo[1,2-a]pyridazine-1,3-dione
1.39 g of tetrahydro-pyrazolo[1,2-a]pyridazine-1,3-dione and 2.68 g of sodium tertiary butanolate are dissolved at 20° in 20 ml of dimethylformamide, and 3.21 g of 2,6-diethyl-4-methyl-iodobenzene and 0.82 g of Pd(TPP)2Cl2 are added. Stirring is then carried out for 2.5 hours at 125°. After cooling to room temperature, 200 ml of ethyl acetate and 200 ml of ether are added and the reaction mixture is poured onto a suction filter. 100 ml of water and 100 ml of methylene chloride are added to the filtration residue, and acidification is carried out using hydrochloric acid. The organic phase is separated off, dried and concentrated by evaporation.
The residue (1.9 g) is chromatographed on silica gel (ethyl acetate/hexane 3:1). 2-(2,6-Diethyl-4-methyl-phenyl)-tetrahydro-pyrazolo[1,2-a]pyridazine-1,3-dione is obtained in the form of beige crystals having a melting point of from 174 to 175°.
Example P6
Preparation of 2-(2,6-diethyl-4-methyl-phenyl)-tetrahydro-pyrazolo [1,2-a]pyridazine-1,3-dione
1.39 g of tetrahydro-pyrazolo[1,2-a]pyridazine-1,3-dione and 2.68 g of sodium tertiary butanolate are dissolved at 20° in 20 ml of dimethylformamide, and 2.66 g of 2,6-diethyl-4-methyl-bromobenzene as well as 0.82 g of Pd(TPP)2Cl2 are added. Stirring is then carried out for 2.5 hours at 125°. After cooling to room temperature, 200 ml of ethyl acetate and 200 ml of ether are added, and the reaction mixture is poured onto a suction filter. 100 ml of water and 100 ml of methylene chloride are added to the filtration residue and acidification is carried out using hydrochloric acid. The organic phase is separated off, dried and concentrated by evaporation. The residue (1.4 g) is chromatographed on silica gel (ethyl acetate/hexane 3:1).
2-(2,6-Diethyl-4-methyl-phenyl)-tetrahydro-pyrazolo[1,2-a]pyridazine-1,3-dione is obtained in the form of beige crystals having a melting point of from 174 to 175°.
In the following Tables, the melting points are quoted in ° C. Me denotes the methyl group. Where a formula is given for the substituents G1 to G10 and R4 and R5 (independently of each other), the left-hand side of that formula is the linking point to the oxygen atom of the heterocycle Q1 to Q10. In the case of the substituent meaning of R4 and R5 together, the right-hand side of the molecule is the linking point to the heterocycle Q1. The remaining terminal valencies are methyl groups.
In the following Tables, “LC/MS: M+” expresses in daltons the positively charged molecular ion that has been ascertained from the mass spectrum in the analysis of the product by coupled HPLC (High Performance Liquid Chromatography) and MS (Mass Spectrometry) devices.







TABLE 1







Compounds of formula Ia:









(Ia)








 












No.
R1
R3
R4/R5
G1
Physical data





1.1
ethyl
ethyl
—(CH2)4—
—H
m.p. 209-211


 


1.2
ethyl
ethyl
—(CH2)4—




m.p. 125-127


 


1.3
ethyl
ethyl








m.p. 195


 


1.4
ethyl
ethyl








m.p. 180


 


1.5
ethyl
ethyl




—H
wax


 


1.6
ethyl
ethyl








solid


 


1.1
ethyl
ethyl








crystalline


 


1.2
ethyl
ethyl




—H
crystalline


 


1.3
ethyl
ethyl




—H
solid


 


1.4
ethyl
ethyl




—H
solid


 


1.5
ethyl
ethyl




—H
solid


 


1.6
ethyl
ethyl








m.p. 153-155


 


1.7
ethyl
ethyl








oil


 


1.8
ethyl
ethyl








oil


 













1.9
ethyl
ethyl












solid


 












1.10
ethyl
ethyl




—H
solid


 


1.11
ethyl
ethyl




—H
viscous


 


1.12
ethyl
ethyl




—H
viscous


 


1.13
ethyl
ethyl




—H
viscous


 


1.14
ethyl
ethyl




—H
viscous


 


1.15
ethyl
ethyl




—H
viscous


 


1.16
ethyl
ethyl








viscous


 


1.17
ethyl
ethyl




—H
viscous


 


1.18
ethyl
ethyl




—H
solid


 


1.19
ethyl
ethyl




—H
solid


 


1.20
ethyl
ethyl








solid


 


1.21
ethyl
ethyl








oil


 


1.22
ethyl
ethyl








viscous


 


1.23
ethyl
ethyl




—H
viscous


 


1.24
ethyl
ethyl




—H
viscous


 


1.25
ethyl
ethyl








viscous


 


1.26
ethyl
ethyl




—H
viscous


 


1.27
ethyl
ethyl




—H
solid


 


1.28
ethyl
ethyl








solid


 


1.29
ethyl
ethyl




—H
crystalline


 


1.30
ethyl
ethyl




—H
wax


 


1.31
ethyl
ethyl








viscous


 


1.32
ethyl
ethyl








viscous


 


1.33
ethyl
ethyl




—H
solid


 


1.34
ethyl
ethyl








wax


 


1.35
ethyl
ethyl




—H
amorphous


 


1.36
ethyl
ethyl




—H
wax


 


1.37
ethyl
ethyl








oil


 


1.38
ethyl
ethyl




—H
crystalline


 


1.39
ethyl
ethyl




—H
solid


 


1.40
ethyl
ethyl








solid


 


1.41
ethyl
ethyl




—H
m.p. 283


 


1.42
ethyl
ethyl




—H
m.p. 227


 


1.43
ethyl
ethyl








m.p. 122-124


 


1.44
ethyl
ethyl




—H
m.p. 148-151


 


1.45
ethyl
ethynyl




—H
m.p. 163-166


 


1.46
ethyl
ethynyl








m.p. 114-116


 


1.47
ethyl
ethyl




—H
solid


 


1.48
ethyl
ethyl
—(CH2)4—






 


1.49
ethyl
ethyl
—(CH2)4—






 


1.50
ethyl
ethyl
—(CH2)4—






 


1.51
ethyl
ethyl
—(CH2)4—






 


1.52
ethyl
ethyl
—(CH2)4—






 


1.53
ethyl
ethyl
—(CH2)4—






 


1.54
ethyl
ethyl
—(CH2)4—






 


1.55
ethyl
ethyl
—(CH2)4—






 


1.56
ethyl
ethyl
—(CH2)4—






 


1.57
ethyl
ethyl
—(CH2)4—






 


1.58
ethyl
ethyl
—(CH2)4—






 


1.59
ethyl
ethyl
—(CH2)4—
—CH2—OMe


 


1.60
ethyl
ethyl
—(CH2)4—
—CH2—SMe


 


1.61
ethyl
ethyl
—(CH2)4—






 


1.62
ethyl
ethyl
—(CH2)4—






 


1.63
ethyl
ethyl
—(CH2)4—






 


1.64
ethyl
ethyl
—(CH2)4—






 


1.65
ethyl
ethyl
—(CH2)4—






 


1.66
MeO—
ethyl
—(CH2)4—




m.p. 143-144° C.


 


1.67
ethyl-
ethynyl
—(CH2)4—






 


1.68
—OCHF2
ethyl
—(CH2)4—






 


1.69
—CHO
ethyl
—(CH2)4—






 


1.70




ethyl
—(CH2)4—






 


1.71




ethyl
—(CH2)4—






 


1.72
MeO—
MeO—
—(CH2)4






 


1.73
MeO—
ethyl
—(CH2)4—
—H
m.p. 159-161° C.


 


1.74
ethyl-
ethynyl
—(CH2)4—
—H


 


1.75
—OCHF2
ethyl
—(CH2)4—
—H


 


1.76
—CHO
ethyl
—(CH2)4—
—H


 


1.77




ethyl
—(CH2)4—
—H


 


1.78




ethyl
—(CH2)4—
—H


 


1.79
MeO—
MeO—
—(CH2)4—
—H


 


1.80
MeO—
ethyl
—(CH2)4—
—CO2C2H5
m.p. 112-113° C.


 


1.81
ethyl
ethyl




—H
m.p. 283° C.(decomposition)


 


1.82
ethyl
ethyl




—H
m.p. 140° C.


 


1.83
MeO—
ethyl




—H
solid


 


1.84
MeO—
ethyl








wax


 


1.85
MeO—
ethyl




—H
m.p. 177-180° C.


 


1.86
MeO—
ethyl




—H
m.p. 208-210° C.


 


1.87
MeO—
ethyl








m.p. 102-104° C.


 


1.88
ethyl
ethyl




—H
m.p. 193-194° C.


 





(trans)


 


1.89
ethyl
ethyl








m.p. 163-165° C.


 





(trans)


 


1.90
ethyl
ethyl








solid


 





(trans)


 


1.91
ethyl
ethyl




—H
wax


 


1.92
ethyl
ethyl








wax


 


1.93
ethyl
ethyl




—H
wax


 


1.94
ethyl
ethyl








wax


 


1.95
ethyl
ethyl








viscous


 


1.96
ethyl
ethyl




—H
m.p. 200-202° C.


 


1.97
ethyl
ethyl




—H
m.p. 210-220° C.(decomposition)


 


1.98
ethyl
ethyl




—H
solid


 


1.99
ethyl
ethynyl




—H
wax


 


1.100
ethyl
ethynyl








wax


 


1.101
ethyl
ethyl








viscous


 


1.102
ethyl
ethyl




—H
wax


 


1.103
OCH3
ethyl








wax


 


1.104
ethyl
ethyl








wax


 


1.105
ethyl
ethyl








wax


 


1.106
ethyl
ethyl








wax


 


1.107
ethyl
ethyl








wax


 


1.108
ethyl
ethyl








wax


 


1.109
ethyl
ethyl








wax


 


1.110
ethyl
ethyl








wax


 


1.111
ethynyl
ethyl








wax


 


1.112
ethynyl
ethyl








wax


 


1.113
ethynyl
ethyl








wax


 


1.114
ethynyl
ethyl








wax


 


1.115
ethynyl
ethyl








wax


 


1.116
ethyl
ethyl




—H
wax


 


1.117
ethyl
ethyl




—H
wax


 


1.118
ethyl
ethynyl




—H
wax


 


1.119
ethyl
ethynyl




—H
wax


 


1.120
OCH3
ethyl




—H
m.p. 130-136° C.


 


1.121
OCH3
ethyl




—H
m.p. 198-200° C.


 


1.122
ethyl
ethyl








wax


 


1.123
ethyl
OCH3








wax


 


1.124
ethynyl
ethyl








wax


 


1.125
ethynyl
ethyl








wax


 


1.126
ethynyl
ethyl








wax


 


1.127
ethyl
ethyl




—H


 


1.128
ethyl
ethyl










 


1.129
OCH3
ethyl








wax(LC/MS: M+ = 552)


 


1.130
OCH3
ethyl








wax(LC/MS: M+ = 590)


 


1.131
OCH3
ethyl








wax(LC/MS: M+ = 535)


 


1.132
OCH3
ethyl








wax(LC/MS: M+ = 546)


 


1.133
OCH3
ethyl








wax(LC/MS: M+ = 584)


 


1.134
OCH3
ethyl








wax(LC/MS: M+ = 550)


 


1.135
OCH3
ethyl








wax(LC/MS: M+ = 482)


 


1.136
OCH3
ethyl








wax(LC/MS: M+ = 550)


 


1.137
OCH3
ethyl








wax(LC/MS: M+ = 568)


 


1.138
OCH3
ethyl








wax(LC/MS: M+ = 574)


 


1.139
OCH3
ethyl








wax(LC/MS: M+ = 580)


 


1.140
OCH3
ethyl








wax(LC/MS: M+ = 552)


 


1.141
OCH3
ethyl








wax(LC/MS: M+ = 550)


 


1.142
OCH3
ethyl








wax(LC/MS: M+ = 561)


 


1.143
OCH3
ethyl








wax(LC/MS: M+ = 520)


 


1.144
OCH3
ethyl




—S(O)2CH3
wax(LC/MS: M+ = 454)


 


1.145
OCH3
ethyl








wax(LC/MS: M+ = 516)


 


1.146
OCH3
ethyl








wax(LC/MS: M+ = 584)


 


1.147
OCH3
ethyl








wax(LC/MS: M+ = 468)


 


1.148
OCH3
ethyl








wax(LC/MS: M+ = 496)


 


1.149
OCH3
ethyl








wax(LC/MS: M+ = 552)


 


1.150
OCH3
ethyl








wax(LC/MS: M+ = 541)


 


1.151
ethyl
ethyl








wax(LC/MS: M+ = 582)


 


1.152
ethyl
ethyl








wax(LC/MS: M+ = 620)


 


1.153
ethyl
ethyl








wax(LC/MS: M+ = 565)


 


1.154
ethyl
ethyl








wax(LC/MS: M+ = 576)


 


1.155
ethyl
ethyl








wax(LC/MS: M+ = 614)


 


1.156
ethyl
ethyl








wax(LC/MS: M+ = 580)


 


1.157
ethyl
ethyl








wax(LC/MS: M+ = 512)


 


1.158
ethyl
ethyl








wax(LC/MS: M+ = 580)


 


1.159
ethyl
ethyl








wax(LC/MS: M+ = 642)


 


1.160
ethyl
ethyl








wax(LC/MS: M+ = 598)


 


1.161
ethyl
ethyl








wax(LC/MS: M+ = 604)


 


1.162
ethyl
ethyl








wax(LC/MS: M+ = 546)


 


1.163
ethyl
ethyl








wax(LC/MS: M+ = 582)


 


1.164
ethyl
ethyl








wax(LC/MS: M+ = 580)


 


1.165
ethyl
ethyl








wax(LC/MS: M+ = 591)


 


1.166
ethyl
ethyl








wax(LC/MS: M+ = 550)


 


1.167
ethyl
ethyl




—S(O)2CH3
wax(LC/MS: M+ = 484)


 


1.168
ethyl
ethyl








wax(LC/MS: M+ = 546)


 


1.169
ethyl
ethyl








wax(LC/MS: M+ = 614)


 


1.170
ethyl
ethyl








wax(LC/MS: M+ = 512)


 


1.171
ethyl
ethyl








wax(LC/MS: M+ = 498)


 


1.172
ethyl
ethyl








wax(LC/MS: M+ = 526)


 


1.173
ethyl
ethyl








wax(LC/MS: M+ = 582)


 


1.174
ethyl
ethyl








wax(LC/MS: M+ = 571)


 


1.175
ethyl
ethyl








wax(LC/MS: M+ = 550)


 


1.176
ethyl
ethyl








wax(LC/MS: M+ = 588)


 


1.177
ethyl
ethyl








wax(LC/MS: M+ = 533)


 


1.178
ethyl
ethyl








wax(LC/MS: M+ = 544)


 


1.179
ethyl
ethyl








wax(LC/MS: M+ = 582)


 


1.180
ethyl
ethyl








wax(LC/MS: M+ = 548)


 


1.181
ethyl
ethyl








wax(LC/MS: M+ = 480)


 


1.182
ethyl
ethyl








wax(LC/MS: M+ = 548)


 


1.183
ethyl
ethyl








wax(LC/MS: M+ = 566)


 


1.184
ethyl
ethyl








wax(LC/MS: M+ = 572)


 


1.185
ethyl
ethyl








wax(LC/MS: M+ = 514)


 


1.186
ethyl
ethyl








wax(LC/MS: M+ = 550)


 


1.187
ethyl
ethyl








wax(LC/MS: M+ = 548)


 


1.188
ethyl
ethyl








wax(LC/MS: M+ = 559)


 


1.189
ethyl
ethyl








wax(LC/MS: M+ = 518)


 


1.190
ethyl
ethyl




—S(O)2CH3
wax(LC/MS: M+ = 452)


 


1.191
ethyl
ethyl








wax(LC/MS: M+ = 514)


 


1.192
ethyl
ethyl








wax(LC/MS: M+ = 582)


 


1.193
ethyl
ethyl








wax(LC/MS: M+ = 480)


 


1.194
ethyl
ethyl








wax(LC/MS: M+ = 466)


 


1.195
ethyl
ethyl








wax(LC/MS: M+ = 494)


 


1.196
ethyl
ethyl








wax(LC/MS: M+ = 550)


 


1.197
ethyl
ethyl








wax(LC/MS: M+ = 539)


 


1.198
ethyl
ethyl








wax(LC/MS: M+ = 572)


 


1.199
OCH3
OCH3
—(CH2)4—
—H
m.p. 180-193° C.


 


1.200
ethyl
ethyl




—CO2C2H5
m.p. 153-154° C.
















TABLE 2







Compounds of formula Ia:









(Ia)








 













No.
R1
R3
R4
R5
G1
Physical data





2.01
ethyl
ethyl
methyl




—H
wax


 


2.02
ethyl
ethyl
methyl




—H
solid


 


2.03
ethyl
ethyl
methyl




—H
solid


 


2.04
ethyl
ethyl
methyl








wax


 


2.05
ethyl
ethyl
methyl








wax


 


2.06
ethyl
ethyl








—H
m.p. 171-172


 


2.07
ethyl
ethyl












wax


 


2.08
ethyl
ethyl








—H
amorphous


 


2.09
ethyl
ethyl












amorphous


 


2.10
ethyl
ethyl








—H


 


2.11
ethyl
ethyl
methyl
methyl






 


2.12
ethyl
ethyl
methyl
methyl
—SO2CH3


 


2.13
ethyl
MeO—
methyl
methyl






 


2.14
ethyl
ethynyl
methyl
methyl






 


2.15
ethyl
ethyl
methyl
-phenyl






 


2.16
ethyl
ethyl
methyl
-3-pyridyl






 


2.17
ethyl
ethyl
methyl
-2-thienyl






 


2.18
ethyl
ethyl
methyl
-allyl






 


2.19
ethyl
ethyl
methyl
-crotyl






 


2.20
ethyl
ethyl
methyl
-4-chloro-phenyl






 


2.21
MeO—
MeO—
methyl
allyl
—H


2.22
ethynyl
ethyl
phenyl-
phenyl
—H


 


2.23
ethynyl
ethyl
phenyl




—H


 


2.24
ethyl
ethyl




methyl-
—H


 


2.25
ethyl
ethyl




methyl-
—H


 


2.26
ethyl
ethyl
phenyl




—H


 


2.27
ethyl
ethyl




methyl-
—H


 


2.28
ethyl
ethyl
-benzyl
methyl-
—H


 


2.29
ethyl
ethyl




methyl-
—H


 


2.30
ethyl
ethyl




methyl-
—H


 


2.31
ethyl
ethyl




methyl-
—H


 


2.32
ethyl
ethyl
—(CH2)2OH
allyl
—H
m.p. 180-185° C.








(decomp.)
















TABLE 3







Compounds of formula Ib:









(Ib)






























Physical


No.
R1
R3
R6
R7
R8
G2
data





3.01
ethyl
ethyl
—Me
—Me
—Me
—H
m.p. 249-254° C.


3.02
ethyl
ethyl
—Me
—H
—Me
—H













3.03
ethyl
ethyl
—CH2—CH2—O—CH2—CH2—
—Me
—H



3.04
ethynyl
ethyl
—CH2—CH2—
—allyl
—H


 


3.05
ethyl
ethyl
—CH2—C(Cl)2—
—Me






 


3.06
ethyl
ethyl
—(CH2)2—
—Me
—H


3.07
ethyl
ethyl
—(CH2)2—CH(CH3)—(CH2)2—
—Me
—H


3.08
ethyl
ethyl
—(CH2)2—C(CH3)2—(CH2)2—
—Me
—H


3.09
ethynyl
ethyl
—(CH2)4—
—Me
—H


3.10
MeO—
ethyl
—(CH2)2—
—H
—H


 


3.11
MeO—
ethyl
—(CH2)2—
—methyl






 


3.12
—C(O)CH3
ethyl
—(CH2)2—
methyl
—H


 


3.13
—OCHF2
ethyl
—(CH2)2—
methyl






 


3.14
ethyl
ethyl
—(CH2)3—
methyl






 


3.15
ethyl
ethyl
—(CH2)5—
—H
—H
m.p. 222-224° C.


 


3.16
ethyl
ethyl
—(CH2)5—
—H




m.p. 147-149° C.


 














3.17
ethyl
ethyl
methyl
methyl
—H
—H
m.p. 244-246° C.


 


3.18
ethyl
ethyl
methyl
methyl
—H




m.p. 164-166° C.


 













3.19
ethyl
ethyl
—(CH2)5—
—n-C4H9
—H
m.p. 170-175° C.


 


3.20
ethyl
ethyl
—(CH2)5—
—n-C4H9




m.p. 99-101° C.


 


3.21
ethyl
ethyl
—(CH2)5—
C3H6OMe
—H
solid


 














3.22
ethyl
ethyl
methyl
methyl
methyl




m.p. 94-101° C.


 













3.23
ethyl
ethyl
—(CH2)5—
methyl
—H
m.p. 252-262° C.


 


3.24
ethyl
ethyl
—(CH2)5—
methyl




m.p. 127-128° C.


 












3.25
ethyl
ethyl




—H
crystalline


 


3.26
ethyl
ethyl








wax


 


3.27
ethyl
ethyl




—H
crystalline


 


3.28
ethyl
ethyl








crystalline


 


3.29
ethyl
ethyl




—H
solid


 


3.30
ethyl
ethyl




—H
solid


 


3.31
ethyl
ethyl










 


3.32
ethyl
ethyl




—H
amorphous
























Physical


No.
R1
R3
R7
R6
R8
G2
data
















3.33
ethyl
ethyl
methyl
—(CH2)4—






 


3.34
ethyl
ethyl
methyl
—(CH2)3—






 


3.35
ethyl
ethyl
—H




—H


 


3.36
ethyl
ethyl
—H










 


3.37
ethyl
ethyl
—H










 


3.38
ethyl
ethyl
—H




—H


 


3.39
ethyl
ethyl
—H










 


3.40
ethyl
ethyl
—H




—H


 


3.41
ethyl
ethyl
—H










 


3.42
ethyl
ethyl
—H




—H


 


3.43
ethyl
ethyl
—H










 


3.44
ethyl
ethyl
—H




—H


 


3.45
ethyl
ethyl
—H
























TABLE 4







Compounds of formula Ic:


 









(Ic)








 



















Physical


No.
R1
R3
R2
R31
G3
Data





4.01
ethyl
ethyl
methyl
methyl
—H
m.p.








224-226° C.


 


4.02
ethyl
ethyl
methyl
methyl




m.p.102-104° C.


 


4.03
ethyl
ethyl
methyl
ethyl
—H


4.04
ethyl
ethynyl
methyl
methyl
—H


 


4.05
ethyl
ethynyl
methyl
methyl






 


4.06
ethyl
methoxy
methyl
methyl
—H












4.07
ethyl
ethyl
—(CH2)2—
—H



 


4.08
ethyl
ethyl
—(CH2)2—CH(CH3)—(CH2)2—






 


4.09
ethyl
ethyl
—(CH2)2—C(CH3)2—(CH2)2—






 


4.10
ethyl
ethyl
—(CH2)4—
—H


 


4.11
ethyl
ethyl
—CH2—CH2—O—CH2—CH2—






 













4.12
ethyl
ethyl
methyl
isopropyl
—H



4.13
ethyl
ethyl
methyl
ethyl
—H


 


4.14
ethyl
ethyl
methyl
n-butyl






 


4.15
ethyl
ethyl
methyl
H






 


4.16
ethyl
ethyl
—H
—H
—H
m.p.








176-178° C.


 


4.17
ethyl
ethyl
—H
—H




m.p.80-82° C.


 


4.18
OCH3
ethyl
—H
—H
—H
m.p.








169-171° C.


 


4.19
OCH3
ethyl
—H
—H




oil
















TABLE 5







Compounds of formula Id:


 









(Id)








 



















Physical


No.
R1
R3
R32
R33
G4
data





5.01
ethyl
ethyl
methyl
methyl
—H
m.p.








181-183° C.


 


5.02
ethyl
ethyl
methyl
methyl




oil


 


5.03
ethyl
ethyl
methyl
ethyl
—H


5.04
ethyl
ethynyl
methyl
methyl
—H


 


5.05
ethyl
ethynyl
methyl
methyl






 


5.06
ethyl
methoxy
methyl
methyl
—H












5.07
ethyl
ethyl
—(CH2)2—
—H



 


5.08
ethyl
ethyl
—(CH2)2—CH(CH3)—(CH2)2—






 


5.09
ethyl
ethyl
—(CH2)2—C(CH3)2—(CH2)2—






 


5.10
ethyl
ethyl
—(CH2)4—






 


5.11
ethyl
ethyl
—CH2—CH2—O—CH2—CH2—






 













5.12
ethyl
ethyl
methyl
isopropyl
—H



5.13
ethyl
ethyl
methyl
ethyl
—H


 


5.14
ethyl
ethyl
methyl
n-butyl






 


5.15
ethyl
ethyl
methyl
H






 


5.16
ethyl
ethyl
methyl
H
—H
oil
















TABLE 6







Compounds of formula Ie:


 









(Ie)








 























Physical


No.
R1
R3
R9
R10
R11
R12
data





6.01
ethyl
ethyl
methyl
—H
methyl
—H






 


6.02
ethyl
ethyl
methyl
methyl
—H
—H






 














6.03
ethyl
ethyl
—(CH2)2—
—H
—H
—H



6.04
ethyl
ethyl
—(CH2)4—
methyl
—H
—H


 


6.05
ethyl
ethyl
—(CH2)2—O—(CH2)2—
—H
—H






 














6.06
ethyl
ethyl
—H
methyl
—(CH2)4—






 














6.07
ethyl
ethyl
—H
—O—
—H






 


6.08
ethyl
ethyl
—H
—CH2—
—H






 


6.09
ethyl
ethynyl
—H
—(CH2)3—
—H






 


6.10
ethyl
MeO—
—H
—(CH2)4—
—H






 


6.11
ethyl
ethynyl
—H
—(CH2)4—
—H




















TABLE 7







Compounds of formula If:


 









(If)








 



















Phys.


No.
R1
R2
R13
R14
G6
data





7.01
ethyl
ethyl
methyl
methyl
—H



7.02
ethyl
ethyl
methyl
—H
—H


7.03
ethyl
ethyl
—H
methyl
—H


7.04
ethyl
ethyl
ethyl
methyl
—H












7.05
ethyl
ethyl
—(CH2)4—
—H



7.06
ethyl
MeO—
—(CH2)4—
—H


 


7.07
ethyl
ethynyl
—(CH2)4—






 


7.08
ethyl
ethynyl
—(CH2)3—
—H
















TABLE 8







Compounds of formula Ig:









(Ig)








 



















Phys.


No.
R1
R2
R34
R35
G7
data





8.01
ethyl
ethyl
methyl
methyl
—H



8.02
ethyl
ethyl
methyl
—H
—H


8.03
ethyl
ethyl
—H
methyl
—H


8.04
ethyl
ethyl
ethyl
methyl
—H


 












8.05
ethyl
ethyl
—(CH2)4—






 


8.06
ethyl
ethyl
—(CH2)3—






 













8.07
ethyl
ethynyl
methyl
methyl






 


8.08
ethyl
methoxy
methyl
methyl




















TABLE 9







Compounds of formula Ih:


 









(Ih)








 












No.
R1
R3
R15
G8
Physical data





9.01
ethyl
ethyl
methyl
—H



9.02
ethyl
methoxy
phenyl
—H


9.03
ethyl
ethynyl
-4-chloro-
—H





phenyl


 


9.04
ethyl
ethyl
ethyl






 


9.05
ethyl
ethyl
—OMe






 


9.06
ethyl
ethyl
—CF3






 


9.07
ethyl
ethyl
isopropyl






 


9.08
ethyl
ethyl
n-butyl






 


9.09
ethyl
ethyl
cyclopropyl






 


9.10
ethyl
ethyl
phenyl
—H
m.p.







208-209° C.


 


9.11
ethyl
ethyl
phenyl




m.p.147-149° C.


 


9.12
ethyl
ethyl
-4-tert-butyl-
—H
m.p.





phenyl

222-224° C.


 


9.13
ethyl
ethyl
-4-tert-butylphenyl




amorphous


 


9.14
ethyl
ethyl
-4-tolyl
—H


 


9.15
ethyl
ethyl
-4-tolyl






 


9.16
ethyl
ethyl
-3-chloro-4-
—H
m.p.





fluorophenyl

186-188° C.


 


9.17
ethyl
ethyl
-3-chloro-4-fluorophenyl




m.p.109-110° C.
















TABLE 10







Compounds of formula Ik:


 









(Ik)








 























Phys.


No.
R1
R3
R16
Y
R17
R18
G9
data





10.01
ethyl
ethyl
methyl
O
methyl
—H






 


10.02
ethyl
ethyl
methyl
O
methyl
methyl






 


10.03
ethyl
ethyl
methyl
N—CH3
methyl
methyl






 














10.04
ethyl
ethyl
methyl




—H






 















10.05
ethyl
ethyl
methyl
—CH2—
methyl
methyl






 


10.06
ethyl
ethyl
methyl
—CH2—
methyl
—H






 














10.07
ethyl
ethyl
ethyl
—CH2—
—(CH2)2—






 















10.08
ethyl
ethynyl
methyl
—CH2—
—H
methyl






 


10.09
ethyl
MeO—
methyl
—CH2—
methyl
methyl






 


10.10
ethyl
ethyl
methyl
O
methyl
—H
—H


10.11
ethyl
ethyl
methyl
O
methyl
methyl
—H


10.12
ethyl
ethyl
methyl
N—CH3
methyl
methyl
—H


 














10.13
ethyl
ethyl
methyl




—H
—H


 















10.14
ethyl
ethyl
methyl
—CH2—
methyl
methyl
—H



10.15
ethyl
ethyl
methyl
—CH2—
methyl
—H
—H














10.16
ethyl
ethyl
ethyl
—CH2—
—(CH2)2—
—H
















10.17
ethyl
ethynyl
methyl
—CH2—
—H
methyl
—H



10.18
ethyl
MeO—
methyl
—CH2—
methyl
methyl
—H









In the following Table 21, Me is methyl, Et is ethyl, Pr is propyl and Bu is butyl:







TABLE 21







Compounds of formula Im:


 









(Im)








 
















Comp.








Phys.


No.
R1
R3
R55
R137
R138
R139
G10
Y2
data



















21.1
Et
Et
H
H
H
H
H
O



21.2
Et
ethynyl
H
H
H
H
H
O


21.3
Et
Et
Me
Me
Me
Me
H
O


21.4
Et
OMe
Me
Me
Me
Me
H
O


21.5
Et
Et
Me
H
H
H
H
O


21.6
ethynyl
Et
Me
H
H
H
H
O


21.7
Et
Et
H
H
Me
Me
H
O


21.8
OMe
Et
H
H
Me
Me
H
O


21.9
Et
Et
Me
H
Me
Me
H
O


21.10
Et
ethynyl
Me
H
Me
Me
H
O


21.11
Et
Et
H
Me
H
Me
H
O


21.12
Et
OMe
H
Me
H
Me
H
O


21.13
Et
Et
Me
Et
H
H
H
O


21.14
ethynyl
Et
Me
Et
H
H
H
O


21.15
Et
Et
H
Et
H
Et
H
O


21.16
OMe
Et
H
Et
H
Et
H
O















21.17
Et
Et
H
H
—(CH2)4—
H
O



21.18
Et
ethynyl
H
H
—(CH2)4—
H
O
















21.19
Et
Et
H
H
H
H
COCMe3
O



21.20
Et
ethynyl
H
H
H
H
SO2Me
O


21.21
Et
Et
Me
Me
Me
Me
COCMe3
O


21.22
Et
OMe
Me
Me
Me
Me
SO2-n-Pr
O


21.23
Et
Et
Me
H
H
H
COCMe3
O


21.24
ethynyl
Et
Me
H
H
H
SO2-n-Bu
O


21.25
Et
Et
H
H
Me
Me
COCMe3
O


21.26
OMe
Et
H
H
Me
Me
SO2C8H17
O


21.27
Et
Et
Me
H
Me
Me
COCMe3
O


21.28
Et
ethynyl
Me
H
Me
Me
SO2Ph
O


21.29
Et
Et
H
Me
H
Me
COCMe3
O


21.30
Et
OMe
H
Me
H
Me
SO2Me
O


21.31
Et
Et
Me
Et
H
H
COCMe3
O


21.32
ethynyl
Et
Me
Et
H
H
COCMe3
O


21.33
Et
Et
H
Et
H
Et
COCMe3
O


21.34
OMe
Et
H
Et
H
Et
COCMe3
O















21.35
Et
Et
H
H
—(CH2)4—
COCMe3
O



21.36
Et
ethynyl
H
H
—(CH2)4—
COCMe3
O
















21.37
Et
Et
H
H
H
H
H
S



21.38
Et
ethynyl
H
H
H
H
H
S


21.39
Et
Et
Me
Me
Me
Me
H
S


21.40
Et
OMe
Me
Me
Me
Me
H
S


21.41
Et
Et
Me
H
H
H
H
S


21.42
ethynyl
Et
Me
H
H
H
H
S


21.43
Et
Et
H
H
Me
Me
H
S


21.44
OMe
Et
H
H
Me
Me
H
S


21.45
Et
Et
Me
H
Me
Me
H
S


21.46
Et
ethynyl
Me
H
Me
Me
H
S


21.47
Et
Et
H
Me
H
Me
H
S


21.48
Et
OMe
H
Me
H
Me
H
S


21.49
Et
Et
Me
Et
H
H
H
S


21.50
ethynyl
Et
Me
Et
H
H
H
S


21.51
Et
Et
H
Et
H
Et
H
S


21.52
OMe
Et
H
Et
H
Et
H
S















21.53
Et
Et
H
H
—(CH2)4—
H
S



21.54
Et
ethynyl
H
H
—(CH2)4—
H
S
















21.55
Et
Et
H
H
H
H
COCMe3
S



21.56
Et
ethynyl
H
H
H
H
SO2Me
S


21.57
Et
Et
Me
Me
Me
Me
COCMe3
S


21.58
Et
OMe
Me
Me
Me
Me
SO2-n-Pr
S


21.59
Et
Et
Me
H
H
H
COCMe3
S


21.60
ethynyl
Et
Me
H
H
H
SO2-n-Bu
S


21.61
Et
Et
H
H
Me
Me
COCMe3
S


21.62
OMe
Et
H
H
Me
Me
SO2C8H17
S


21.63
Et
Et
Me
H
Me
Me
COCMe3
S


21.64
Et
ethynyl
Me
H
Me
Me
SO2Ph
S


21.65
Et
Et
H
Me
H
Me
COCMe3
S


21.66
Et
OMe
H
Me
H
Me
SO2Me
S


21.67
Et
Et
Me
Et
H
H
COCMe3
S


21.68
ethynyl
Et
Me
Et
H
H
COCMe3
S


21.69
Et
Et
H
Et
H
Et
COCMe3
S


21.70
OMe
Et
H
Et
H
Et
COCMe3
S















21.71
Et
Et
H
H
—(CH2)4—
COCMe3
S



21.72
Et
ethynyl
H
H
—(CH2)4—
COCMe3
S
















21.73
Et
Et
H
H
H
H
H
NCH(CH3)2



21.74
Et
Et
H
H
H
H
H
NCH3


21.75
Et
Et
H
H
H
H
H
NCH2Ph


21.76
Et
ethynyl
H
H
H
H
H
NCH3


21.77
Et
Et
Me
Me
Me
Me
H
NCH(CH3)2


21.78
Et
OMe
Me
Me
Me
Me
H
NCH3


21.79
Et
Et
Me
H
H
H
H
NCH(CH3)2


21.80
ethynyl
Et
Me
H
H
H
H
NCH3


21.81
Et
Et
H
H
Me
Me
H
NCH3


21.82
OMe
Et
H
H
Me
Me
H
NCH(CH3)2


21.83
Et
Et
Me
H
Me
Me
H
NCH2Ph


21.84
Et
ethynyl
Me
H
Me
Me
H
NCH3


21.85
Et
Et
H
Me
H
Me
H
NCH2Ph


21.86
Et
OMe
H
Me
H
Me
H
NCH3


21.87
Et
Et
Me
Et
H
H
H
NCH(CH3)2


21.88
ethynyl
Et
Me
Et
H
H
H
NCH3


21.89
Et
Et
H
Et
H
Et
H
NCH2Ph


21.90
OMe
Et
H
Et
H
Et
H
NCH(CH3)2















21.91
Et
Et
H
H
—(CH2)4—
H
NCH(CH3)2



21.92
Et
ethynyl
H
H
—(CH2)4—
H
NCH3
















21.93
OMe
Et
Et
Me
H
H
H
NCH3



21.94
Et
Et
H
H
H
H
COCMe3
NCH(CH3)2


21.95
Et
Et
H
H
H
H
SO2Me
NCH3


21.96
Et
Et
H
H
H
H
COCMe3
NCH2Ph


21.97
Et
ethynyl
H
H
H
H
SO2-n-Pr
NCH3


21.98
Et
Et
Me
Me
Me
Me
COCMe3
NCH(CH3)2


21.99
Et
OMe
Me
Me
Me
Me
SO2-n-Bu
NCH3


21.100
Et
Et
Me
H
H
H
COCMe3
NCH(CH3)2


21.101
ethynyl
Et
Me
H
H
H
SO2C8H17
NCH3


21.102
Et
Et
H
H
Me
Me
COCMe3
NCH3


21.103
OMe
Et
H
H
Me
Me
SO2Ph
NCH(CH3)2


21.104
Et
Et
Me
H
Me
Me
COCMe3
NCH2Ph


21.105
Et
ethynyl
Me
H
Me
Me
SO2Me
NCH3


21.106
Et
Et
H
Me
H
Me
COCMe3
NCH2Ph


21.107
Et
OMe
H
Me
H
Me
COCMe3
NCH3


21.108
Et
Et
Me
Et
H
H
COCMe3
NCH(CH3)2


21.109
ethynyl
Et
Me
Et
H
H
COCMe3
NCH3


21.110
Et
Et
H
Et
H
Et
COCMe3
NCH2Ph


21.111
OMe
Et
H
Et
H
Et
COCMe3
NCH(CH3)2















21.112
Et
Et
H
H
—(CH2)4—
COCMe3
NCH(CH3)2



21.113
Et
ethynyl
H
H
—(CH2)4—
SO2C8H17
NCH3
















21.114
OMe
Et
Et
Me
H
H
SO2-n-Bu
NCH3
















21.115
Et
Et
H
—(CH2)2—
H
H
CH2



21.116
Et
ethynyl
H
—(CH2)2—
H
H
CH2















21.117
Et
Et
—(CH2)2—
H
H
H
CH2



21.118
Et
OMe
—(CH2)2—
H
H
H
CH2
















21.119
Et
Et
H
Me
Me
H
H
CH2



21.120
ethynyl
Et
H
Me
Me
H
H
CH2


21.121
Et
Et
Et
H
H
H
H
CH2


21.122
OMe
Et
Et
H
H
H
H
CH2


21.123
Et
Et
H
H
Me
Me
H
CH2


21.124
Et
ethynyl
H
H
Me
Me
H
CH2


21.125
Et
Et
H
OMe
H
H
H
CH2


21.126
Et
OMe
H
OMe
H
H
H
CH2















21.127
Et
Et
H
—(CH2)3—
H
H
CH2



21.128
ethynyl
Et
H
—(CH2)3—
H
H
CH2
















21.129
Et
Et
Me
H
Me
Me
H
CH2



21.130
OMe
Et
Me
H
Me
Me
H
CH2


21.131
Et
Et
Me
OMe
H
H
H
CH2


21.132
Et
ethynyl
Me
OMe
H
H
H
CH2


21.133
Et
Et
H
SMe
H
H
H
CH2


21.134
Et
OMe
H
SMe
H
H
H
CH2


21.135
Et
Et
Me
Me
Me
Me
H
CH2


21.136
ethynyl
Et
Me
Me
Me
Me
H
CH2


21.137
Et
Et
OH
Me
Me
Me
H
CH2


21.138
OMe
Et
OH
Me
Me
Me
H
CH2


21.139
Et
Et
Me
SMe
H
H
H
CH2


21.140
Et
ethynyl
Me
SMe
H
H
H
CH2


21.141
Et
Et
Et
Et
H
Me
H
CH2


21.142
Et
ethynyl
Et
Et
H
Me
H
CH2


21.143
Et
Et
Me
Me
H
CH2OMe
H
CH2


21.144
Et
OMe
Me
Me
H
CH2OMe
H
CH2


21.145
Et
ethynyl
Me
SMe
H
OMe
H
CH2


21.146
Et
Et
Me
SMe
H
OMe
H
CH2


21.147
Et
OMe
Me
SMe
H
OMe
H
CH2















21.148
Et
Et
H
—(CH2)2—
H
COCMe3
CH2



21.149
Et
ethynyl
H
—(CH2)2—
H
COCMe3
CH2















21.150
Et
Et
—(CH2)2—
H
H
SO2-n-Pr
CH2



21.151
Et
OMe
—(CH2)2—
H
H
COCMe3
CH2
















21.152
Et
Et
H
Me
Me
H
COCMe3
CH2



21.153
ethynyl
Et
H
Me
Me
H
SO2Me
CH2


21.154
Et
Et
Et
H
H
H
COCMe3
CH2


21.155
OMe
Et
Et
H
H
H
SO2-n-Pr
CH2


21.156
Et
Et
H
H
Me
Me
COCMe3
CH2


21.157
Et
ethynyl
H
H
Me
Me
SO2-n-Bu
CH2


21.158
Et
Et
H
OMe
H
H
COCMe3
CH2


21.159
Et
OMe
H
OMe
H
H
SO2C8H17
CH2















21.160
Et
Et
H
—(CH2)3—
H
COCMe3
CH2



21.161
ethynyl
Et
H
—(CH2)3—
H
COCMe3
CH2
















21.162
Et
Et
Me
H
Me
Me
SO2-n-Pr
CH2



21.163
OMe
Et
Me
H
Me
Me
COCMe3
CH2


21.164
Et
Et
Me
OMe
H
H
COCMe3
CH2


21.165
Et
ethynyl
Me
OMe
H
H
SO2Me
CH2


21.166
Et
Et
H
SMe
H
H
COCMe3
CH2


21.167
Et
OMe
H
SMe
H
H
SO2-n-Pr
CH2


21.168
Et
Et
Me
Me
Me
Me
COCMe3
CH2


21.169
ethynyl
Et
Me
Me
Me
Me
SO2-n-Bu
CH2


21.170
Et
Et
OH
Me
Me
Me
COCMe3
CH2


21.171
OMe
Et
OH
Me
Me
Me
SO2C8H17
CH2


21.172
Et
Et
Me
SMe
H
H
COCMe3
CH2


21.173
Et
ethynyl
Me
SMe
H
H
COCMe3
CH2


21.174
Et
Et
Et
Et
H
Me
COCMe3
CH2


21.175
Et
ethynyl
Et
Et
H
Me
SO2C8H17
CH2


21.176
Et
Et
Me
Me
H
CH2OMe
SO2-n-Pr
CH2


21.177
Et
OMe
Me
Me
H
CH2OMe
COCMe3
CH2


21.178
Et
ethynyl
Me
SMe
H
OMe
COCMe3
CH2


21.179
Et
Et
Me
SMe
H
OMe
SO2C8H17
CH2


21.180
Et
OMe
Me
SMe
H
OMe
COCMe3
CH2















21.181
Et
Et
H
—(CH2)2—
H
H
CHCH3



21.182
Et
ethynyl
H
—(CH2)2—
H
H
CHCH3















21.183
Et
Et
—(CH2)2—
H
H
H
CHCH3



21.184
Et
OMe
—(CH2)2—
H
H
H
CHCH3
















21.185
Et
Et
H
Me
Me
H
H
CHCH3



21.186
ethynyl
Et
H
Me
Me
H
H
CHCH3


21.187
Et
Et
Et
H
H
H
H
CHCH3


21.188
OMe
Et
Et
H
H
H
H
CHCH3


21.189
Et
Et
H
H
Me
Me
H
CHCH3


21.190
Et
ethynyl
H
H
Me
Me
H
CHCH3















21.191
Et
Et
H
—(CH2)2—
H
COCMe3
CHCH3



21.192
Et
ethynyl
H
—(CH2)2—
H
COCMe3
CHCH3















21.193
Et
Et
—(CH2)2—
H
H
SO2-n-Pr
CHCH3



21.194
Et
OMe
—(CH2)2—
H
H
COCMe3
CHCH3
















21.195
Et
Et
H
Me
Me
H
COCMe3
CHCH3



21.196
ethynyl
Et
H
Me
Me
H
SO2Me
CHCH3


21.197
Et
Et
Et
H
H
H
COCMe3
CHCH3


21.198
OMe
Et
Et
H
H
H
SO2-n-Pr
CHCH3


21.199
Et
Et
H
H
Me
Me
COCMe3
CHCH3


21.200
Et
ethynyl
H
H
Me
Me
SO2-n-Bu
CHCH3















21.201
Et
Et
H
—(CH2)2—
H
H
C(CH3)2



21.202
Et
ethynyl
H
—(CH2)2—
H
H
C(CH3)2















21.203
Et
Et
—(CH2)2—
H
H
H
C(CH3)2



21.204
Et
OMe
—(CH2)2—
H
H
H
C(CH3)2
















21.205
Et
Et
H
Me
Me
H
H
C(CH3)2



21.206
ethynyl
Et
H
Me
Me
H
H
C(CH3)2


21.207
Et
Et
Et
H
H
H
H
C(CH3)2


21.208
OMe
Et
Et
H
H
H
H
C(CH3)2















21.209
Et
Et
H
—(CH2)2—
H
COCMe3
C(CH3)2



21.210
Et
ethynyl
H
—(CH2)2—
H
COCMe3
C(CH3)2















21.211
Et
Et
—(CH2)2—
H
H
SO2-n-Pr
C(CH3)2



21.212
Et
OMe
—(CH2)2—
H
H
COCMe3
C(CH3)2
















21.213
Et
Et
H
Me
Me
H
COCMe3
C(CH3)2



21.214
ethynyl
Et
H
Me
Me
H
SO2Me
C(CH3)2


21.215
Et
Et
Et
H
H
H
COCMe3
C(CH3)2


21.216
OMe
Et
Et
H
H
H
SO2-n-Pr
C(CH3)2


21.217
Et
Et
Me
Me
Me
Me
H
CHCO2Me


21.218
Et
Et
H
H
H
H
H
CHCO2Me


21.219
Et
Et
Me
Me
Me
Me
COCMe3
CHCO2Me


21.220
Et
Et
H
H
H
H
COCMe3
CHCO2Me















21.221
Et
OMe
—(CH2)2—
H
H
H
CHCO2Me



21.222
Et
OMe
—(CH2)2—
H
H
COCMe3
CHCO2Me









BIOLOGICAL EXAMPLES
Comparison Test:
The following compounds were tested for their herbicidal action:
Compound No. 1.02




according to the present invention, and compound A





Example B1
Herbicidal Action Prior to Emergencies of the Plants (Pre-Emergence Action)
Monocotyledonous and dicotyledonous weeds are sown in plastics pots in standard soil. Immediately after sowing, the test substances are applied in the form of an aqueous suspension (prepared from a 25% wettable powder (Example F3, b)) or in the form of an emulsion (prepared from a 25% emulsifiable concentrate (Example F1, c)) (500 liters of water/ha). The rate of application is 500 g of active substance/ha. The test plants are then grown in the greenhouse under optimum conditions. The evaluation is carried out 3 weeks after application, using a scale of nine ratings (1=total damage, 9=no action). Ratings of from 1 to 4 (especially from 1 to 3) indicate good to very good herbicidal action.
Test plants: Alopecurus (Alo), Avena (Ave), Lolium (Lol), Setaria (Set), Panicum (Pan), Sorghum (Sor), Digitaria (Dig), Echinochloa (Ech) and Brachiaria (Bra).







TABLE B1







Pre-emergence action:


Pre-emergence action at 500 g of active ingredient/ha
















Comp. No.
Alo
Ave
Lol
Set
Pan
Sor
Dig
Ech
Bra





compound A
2
4
1
2
1
4
4
5
3


1.02
1
1
1
1
1
1
4
1
1









Example B2
Herbicidal Action After Emergence of the Plants (Post-emergence Action)
Monocotyledonous and dicotyledonous weeds are grown in standard soil in plastics pots under greenhouse conditions. The test substances are applied to the test plants at the 3- to 6-leaf stage. The test substances are applied at a rate of application of 500 g of active substance per hectare in the form of an aqueous suspension (prepared from a 25% wettable powder (Example F3, b)) or in the form of an emulsion (prepared from a 25% emulsifiable concentrate (Example F1, c)) (500 liters of water/ha). The evaluation is carried out 3 weeks after application, using a scale of nine ratings (1=total damage, 9=no action). Ratings of from 1 to 4 (especially from 1 to 3) indicate good to very good herbicidal action.
Test plants: Alopecurus (Alo), Avena (Ave), Lolium (Lol), Setaria (Set), Panicum (Pan), Sorghum (Sor), Digitaria (Dig), Echinocloa (Ech) and Brachiaria (Bra).







TABLE B2







Post-emergence action:


Post-emergence action at 250 g of active ingredient/ha
















Comp. No.
Alo
Ave
Lol
Set
Pan
Sor
Dig
Ech
Bra





compound A
3
3
2
2
1
3
2
1
2


1.02
1
1
1
1
1
1
2
1
1









By comparing the herbicidal activity of compound A with compound no. 1.02 of the present invention, it can be seen that, in the case of all weeds tested, compound no. 1.02 surprisingly exhibits an appreciably improved herbicidal action, although the only difference between that compound and compound A is that two ethyl groups have been replaced by methyl groups.
Example B3
Herbicidal Action Prior to the Emergence of the Plants (Pre-emergence Action) of Compounds of the Present Invention
Monocotyledonous and dicotyledonous weeds are sown in standard soil in plastics pots. Immediately after sowing, the test substances are applied in the form of an aqueous suspension (prepared from a 25% wettable powder (Example F3, b)) or in the form of an emulsion (prepared from a 25% emulsifiable concentrate (Example F1, c)) (500 liters of water/ha). The rate of application is 500 g of active substance/ha. The test plants are then grown in the greenhouse under optimum conditions. The evaluation is carried out 3 weeks after application, sing a scale of nine ratings (1=total damage, 9=no action). Ratings of from 1 to 4 (especially from 1 to 3) indicate good to very good herbicidal action.
Test plants: Avena (Ave), Lolium (Lol), Setaria (Set).







TABLE B3







Pre-emergence action: MERGE ® is used as oil additive in a


concentration of 0.7% by weight of the spray mixture









Test plant:












Comp. No.
Ave
Lol
Set







1.01
1
1
1



1.02
1
1
1



1.31
1
1
2



1.35
1
1
1










The same results are obtained when the compounds of formula I are formulated in accordance with Examples F2 and F4 to F8.
Example B4
Herbicidal Action After the Emergence of the Plants (Post-emergence Action) of Compounds of the Present Invention (for Description See Example B2)
Test plants: Avena (Ave), Lolium (Lol), Setaria (Set). The results are given in the following Table B4:







TABLE B4







Post-emergence action: MERGE ® is


used as oil additive in a concentration of


0.7% by weight of the spray mixture.









Test plant:












Comp. No.
Ave
Lol
Set
















1.01
1
1
1



1.02
1
1
1



1.04
1
1
1



1.05
1
3
1



1.07
1
1
1



1.08
1
1
1



1.10
1
1
1



1.11
1
1
1



1.14
1
2
2



1.15
1
2
1



1.17
1
1
2



1.19
1
1
1



1.21
1
1
1



1.23
1
1
1



1.26
1
2
1



1.27
1
1
2



1.30
1
1
1



1.31
1
1
1



1.35
1
1
1



1.37
1
1
1



1.39
1
1
1



1.40
1
1
2



1.43
1
2
2










The same results are obtained when the compounds of formula I are formulated in accordance with Examples F2 and F4 to F8.

## Claims

1. A selective-herbicidal composition comprising a mixture of
a) a herbicidally effective amount of a compound of formula I





wherein
R1 and R3 are each independently of the other ethyl, haloethyl, ethynyl, C1-C2alkoxy, C1-C2haloalkoxy, C1-C2alkylcarbonyl, C1-C2hydroxyalkyl or C1-C2alkoxycarbonyl;
Q is a group







R4 and R5 are each independently of the other C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C2-C10—N-alkoxyiminoalkyl, C2-C10alkoxycarbonylalkyl, C1-C10aminoalkyl, C3-C10dialkylaminoalkyl, C2-C10alkylaminoalkyl, C1-C10cyanoalkyl, C4-C10cycloalkylalkyl, C1-C10phenylalkyl, C1-C10heteroarylalkyl, C1-C10phenoxyalkyl, C1-C10heteroaryloxyalkyl, C1-C10alkylideneaminooxyalkyl, C1-C10nitroalkyl, C1-C10trialkylsilylalkyl, C2-C10alkylaminocarbonylalkyl, C2-C10dialkylaminocarbonylalkyl, C2-C10alkylaminocarbonyloxyalkyl, C3-C10dialkylaminocarbonyloxalkyl, C2-C10alkoxycarbonylaminoalkyl, C1-C10—N-alkoxycarbonyl-N-alkylaminoalkyl, C1-C10cycloalkyl, aryl or heteroaryl; or
R4 and R5, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur and that, in addition, may contain a fused or spiro-bound alkylene or alkenylene chain consisting of from 2 to 6 carbon atoms, which chain may in turn contain one or two hetero atoms selected from oxygen and sulfur, wherein the cyclic group may be substituted by phenyl or benzyl, which in turn may be substituted by halogen, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, hydroxy, C1-C6alkoxy C1-C6alkoxy-C1-C6alkoxy, C1-C6haloalkoxy or by nitro;
R2, R6 and R32 are each independently of the others C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R7, R31 and R33 are each independently of the others hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C2-C10alkoxyalkyl;
R8 is hydrogen, C1-C10alkyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10-alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
R6 and R7 or R2 and R31 or R32 and R33, together with the atom to which they are bonded, form a saturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur; or R6 and R8, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R9, R10, R11 and R12 are each independently of the others C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
R9 and R11 or R9 and R10, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R13, R14, R34 and R35 are each independently of the others C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
R13 and R14 or R34 and R35, together with the atoms to which they are bonded, from a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R15 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C2-C10alkoxycarbonylalkyl, C1-C10aminoalkyl, C3-C10dialkylaminoalkyl, C2-C10alkylaminoalkyl, C1-C10cyanoalkyl, C4-C10cycloalkylalkyl, C1-C10phenylalkyl, C1-C10heteroarylalkyl, C1-C10phenoxyalkyl, C1-C10heteroaryloxyalkyl, C1-C10nitroalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R16 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthiolkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R17 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R18 is hydrogen, C2-C10alkenyl, C2-C10alkynyl, C1-C10alkyl or C1-C10alkoxyalkyl; or
R17 and R18, together with the atoms to which they are bonded, form a 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
Y is oxygen, sulfur, C—R19 or N—R36;
R19 and R36 are each independently of the other C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, phenyl or heteroaryl; or
R18 and R19 or R18 and R36, together with the atom to which they are bonded, form a saturated 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
G1, G2, G3, G4, G5, G6, G7, G8, G9 and G10 are each independently of the others hydrogen, —C(X1)—R20, —C(X2)—X3—R21, —C(X4)—N(R22)—R23, —SO2—R24, an alkali metal cation, alkaline earth metal cation, sulfonium cation or ammonium cation, —P(X5)(R25)—R26 or —CH2—X6—R27;
X1, X2, X3, X4, X5 and X6 are each independently of the others oxygen or sulfur;
R20, R21, R22 and R23 are each independently of the others hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl, C1-C5alkyl, C2-C10alkoxyalkyl, C4-C10alkenyloxyalkyl, C4-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C1-C5alkylsulfoxyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylideneaminooxy-C1-C5alkyl, C1-C5alkylcarbonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminocarbonyl-C1-C5alkyl, C1-C5alkylcarbonylamino-C1-C5alkyl, C1-C5alkylcarbonyl-(C2-C5alkyl)-aminoalkyl, C3-C6trialkylsilyl-C1-C5alkyl, phenyl-C1-C5alkyl, heteroaryl-C1-C5alkyl, phenoxy-C1-C5alkyl, heteroaryloxy-C1-C5alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or heteroaryl or heteroarylamino, or heteroaryl or heteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diheteroarylamino, or diheteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, phenylamino, or phenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diphenylamino, or diphenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or C3-C7cycloalkylamino, di-C3-C7cycloalkylamino or C3-C7cycloalkoxy;
R24, R25 and R26 are hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl, C4-C10alkenyloxyalkyl, C4-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C1-C5alkylsulfoxyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylideneaminooxy-C1-C5alkyl, C1-C5alkylcarbonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminocarbonyl-C1-C5alkyl, C1-C5alkylcarbonylamino-C1-C5alkyl, C1-C5alkylcarbonyl-(C2-C5alkyl)-aminoalkyl, C3-C6trialkylsilyl-C1-C5alkyl, phenyl-C1-C5alkyl, heteroaryl-C1-C5alkyl, phenoxy-C1-C5alkyl, heteroaryloxy-C1-C5alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or heteroaryl or heteroarylamino, or heteroaryl or heteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diheteroarylamino, or diheteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3haloalkoxy, halogen, cyano or by nitro, phenylamino, or phenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diphenylamino, or diphenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or C3-C7cycloalkylamino, di-C3-C7cycloalkylamino, C3-C7cycloalkoxy, C1-C10alkoxy, C1-C10haloalkoxy, C1-C5alkylamino, C2-C8dialkylamino, benzyloxy or phenoxy, wherein the benzyl and phenyl groups may in turn be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
R27 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl, C4-C10alkenyloxyalkyl, C4-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C1-C5alkylsulfoxyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylideneaminooxy-C1-C5alkyl, C1-C5alkylcarbonyl-C1-C5-alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminocarbonyl-C1-C5alkyl, C1-C5alkylcarbonylamino-C1-C5alkyl, C1-C5alkylcarbonyl-(C2-C5alkyl)-aminoalkyl, C3-C6trialkylsilyl-C1-C5alkyl, phenyl-C1-C5alkyl, heteroaryl-C1-C5alkyl, phenoxy-C1-C5alkyl, heteroaryloxy-C1-C5alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or heteroaryl or heteroarylamino, or heteroaryl or heteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diheteroarylamino, diheteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or phenylamino, phenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, halogen, cyano or by nitro, diphenylamino, diphenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, C3-C7cycloalkylamino, di-C3-C7cycloalkylamino, C3-C7cycloalkoxy or C1-C10alkylcarbonyl;
Y2 is oxygen, sulfur, C—R140—R141 or N—R142,
R55 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R137 is hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C1-C10alkoxyalkyl; or
R55 and R137, together with the atoms to which they are bonded, form a 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R138 and R139 are each independently of the other hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C2-C10alkoxyalkyl; and
R140 and R141 are each independently of the other hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C1-C10alkoxyalkyl; or
R55 and C—R140, together with the atoms to which they are bonded, form a saturated or unsaturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R142 is hydrogen, C1-C10alkyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
R55 and N—R142, together with the atoms to which they are bonded, form a saturated or unsaturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
or an agronomically tolerable salt, isomer or enantiomer of such a compound; and
b) a herbicide-antagonistically effective amount either of a compound of formula X





wherein
R37 is hydrogen, C1-C8alkyl, or C1-8alkyl substituted by C1-C6alkoxy or by C3-C6alkenyloxy; and X7 is hydrogen or chlorine; or of a compound of formula XI





wherein
E is nitrogen or methine;
R38 is —CCl3, phenyl or phenyl substituted by halogen;
R39 and R40 are each independently of the other hydrogen or halogen; and
R41 is C1-C4alkyl; or of a compound of formula XII





wherein R44 and R45 are each independently of the other hydrogen or halogen, and
R46, R47 and R48 are each independently of the others C1-C4alkyl, or of a compound of formula XIII




R51 and R52 are each independently of the other hydrogen, C1-C8alkyl, C3-C8cycloalkyl, C3-C6alkenyl, C3-C6alkynyl,





or C1-C4alkyl substituted by C1-C4alkoxy or by




or R51 and R52 together form a C4-C6alkylene bridge that may be interrupted by oxygen, sulfur, SO, SO2, NH or by —N(C1-C4alkyl)-;
R53 is hydrogen or C1-C4alkyl;
R49 is hydrogen, halogen, cyano, trifluoromethyl, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj, —CONRkRm, —CORn, —SO2NRkRm or —OSO2—C1-C4alkyl;
R9 is hydrogen, halogen, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj, —CONRkRm, —CORn, —SO2NRkRm, —OSO2—C1-C4alkyl, C1-C6alkoxy, or C1-C6alkoxy substituted by C1-C4alkoxy or by halogen, C3-C6alkenyloxy, or C3-C6alkenyloxy substituted by halogen, or C3-C6alkynyloxy, or R49 and R50 together form a C3-C4alkylene bridge that may be substituted by halogen or by C1-C4alkyl, or together form a C3-C4alkenylene bridge that may be substituted by halogen or by C1-C4alkyl, or together form a C4alkadienylene bridge that may be substituted by halogen or by C1-C4alkyl;
R50 and Rh are each independently of the other hydrogen, halogen, C1-C4alkyl, trifluoromethyl, C1-C6alkoxy, C1-C6alkylthio or —COORj;
Rc is hydrogen, halogen, nitro, C1-C4alkyl or methoxy; Rd is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm;
Re is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy, or Rd and Re together form a C3-C4alkylene bridge;
Rp is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy; Rq is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm; or Rp and Rq together form a C3-C4alkylene bridge;
Rr is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy; Rs is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm; or Rr and Rs together form a C3-C4alkylene bridge;
Rt is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy; Ru is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm; or Rv and Ru together form a C3-C4alkylene bridge;
Rf and Rv are hydrogen, halogen or C1-C4alkyl;
Rx and Ry are each independently of the other hydrogen, halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, —COOR54, trifluoromethyl, nitro or cyano;
Rj, Rk and Rm are each independently of the others hydrogen or C1-C4alkyl; or
Rk and Rm together form a C4-C6alkylene bridge that may be interrupted by oxygen, NH or by —N(C1-C4alkyl)-;
Rn is C1-C4alkyl, phenyl, or phenyl substituted by halogen, C1-C4alkyl, methoxy, nitro or by trifluoromethyl;
R54 is hydrogen, C1-C10alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylthio-C1-C4alkyl, di-C1-C4alkylamino-C1-C4alkyl, halo-C1-C8alkyl, C2-C8alkenyl, halo-C2-C8alkenyl, C3-C8alkynyl, C3-C7cycloalkyl, halo-C3-C7cycloalkyl, C1-C8alkylcarbonyl, allylcarbonyl, C3-C7cycloalkylcarbonyl, benzoyl, which is unsubstituted or substituted on the phenyl ring identically or differently up to three times by halogen, C1-C4alkyl, halo-C1-C4alkyl, halo-C1-C4alkoxy or C1-C4alkoxy; or furoyl, thienyl; or C1-C4alkyl substituted by phenyl, halophenyl, C1-C4alkylphenyl, C1-C4alkoxyphenyl, halo-C1-C4alkylphenyl, halo-C1-C4alkoxyphenyl, C1-C6alkoxycarbonyl, C1-C4alkoxy-C1-C8alkoxycarbonyl, C3-C8alkenyloxycarbonyl, C3-C8alkynyloxycarbonyl, C1-C8alkylthiocarbonyl, C3-C8alkenylthiocarbonyl, C3-C8alkynylthiocarbonyl, carbamoyl, mono-C1-C4alkylaminocarbonyl, di-C1-C4alkylaminocarbonyl; or phenylaminocarbonyl, which is unsubstituted or substituted on the phenyl identically or differently up to three times by halogen, C1-C4alkyl, halo-C1-C4alkyl, halo-C1-C4alkoxy or C1-C4alkoxy or once by cyano or nitro; or dioxolan-2-yl, which is unsubstituted or substituted by one or two C1-C4alkyl radicals, or dioxan-2-yl, which is unsubstituted or substituted by one or two C1-C4alkyl radicals, or C1-C4alkyl, which is substituted by cyano, nitro, carboxyl or by C1-C8alkylthio-C1-C8alkoxycarbonyl;

or of a compound of formula XIV




wherein R56 and R57 are each independently of the other C1-C6alkyl or C2-C6alkenyl; or R56 and R57 together are




R58 and R59 are each independently of the other hydrogen or C1-C6alkyl; or R56 and R57 together are



R60 and R61 are each independently of the other C1-C4alkyl, or R60 and R61 together are —(CH2)5—;
R62 is hydrogen, C1-C4alkyl or





or R56 and R57 together are



R63, R64, R65, R66, R67, R68, R69, R70, R71, R72, R73, R74, R75, R76, R77 and R78 are each independently of the others hydrogen or C1-C4alkyl;

or of a compound of formula XV



wherein R80 is hydrogen or chlorine and R79 is cyano or trifluoromethyl;

or of a compound of formula XVI



wherein R81 is hydrogen or methyl;

or of a compound of formula XVI



wherein R81 is hydrogen or methyl;

or of a compound of formula XVII




wherein
R82 is hydrogen, C1-C4alkyl, or C1-C4alkyl substituted by C1-C4alkyl-X2— or by C1-C4haloalkyl-X2—, or is C1-C4haloalkyl, nitro, cyano, —COOR85, —NR86R87, —SO2NR88R89 or —CONR90R91;
R83 is hydrogen, halogen, C1-C4alkyl, trifluoromethyl, C1-C4alkoxy or C1-C4haloalkoxy;
R84 is hydrogen, halogen or C1-C4alkyl;
U, V, W1 and Z4 are each independently of the others oxygen, sulfur, C(R92)R93, carbonyl, NR94, or a group





wherein R102 is C2-C4alkenyl or C2-C4alkynyl; with the provisos that
a) at least one of the ring members U, V, W1 or Z4 is carbonyl, and a ring member adjacent to that ring member or to those ring members is the group





that group appearing only once; and
b) two adjacent ring members U and V, V and W1 and W1 and Z4 cannot simultaneously be oxygen;
R95 and R96 are each independently of the other hydrogen or C1-C8alkyl; or
R95 and R96 together form a C2-C6alkylene group;
A1 is R99—Y1— or —NR97R98;
X2 is oxygen or —S(O)s;
Y1 is oxygen or sulfur;
R99 is hydrogen, C1-C8alkyl, C1-C8haloalkyl, C1-C4alkoxy-C1-C8alkyl, C3-C6alkenyloxy-C1-C8alkyl, or phenyl-C1-C8alkyl in which the phenyl ring may be substituted by halogen, C1-C4alkyl, trifluoromethyl, methoxy or by methyl-S(O)s—, or is C3-C6alkenyl, C3-C6haloalkenyl, phenyl-C3-C6-alkenyl, C3-C6alkynyl, phenyl-C3-C6alkynyl, oxetanyl, furyl or tetrahydrofuryl;
R85 is hydrogen or C1-C4alkyl;
R86 is hydrogen, C1-C4alkyl or C1-C4alkylcarbonyl;
R87 is hydrogen or C1-C4alkyl; or
R86 and R87 together form a C4- or C5-alkylene group;
R88, R89, R90 and R91 are each independently of the others hydrogen or C1-C4alkyl; or R88 together with R89, or R90 together with R91, are each independently of the other C4- or C5-alkylene in which one carbon atom may have been replaced by oxygen or by sulfur, or one or two carbon atoms may have been replaced by —NR100—;
R92, R100 and R93 are each independently of the others hydrogen or C1-C8alkyl; or
R92 and R93 together are C2-C6alkylene;
R94 is hydrogen or C1-C8alkyl;
R97 is hydrogen, C1-C8alkyl, phenyl or phenyl-C1-C8alkyl, wherein the phenyl rings may be substituted by fluorine, chlorine, bromine, nitro, cyano, —OCH3, C1-C4alkyl or by CH3SO2—, or is C1-C4alkoxy-C1-C8alkyl, C3-C6alkenyl or C3-C6alkynyl;
R98 is hydrogen, C1-C8alkyl, C3-C6alkenyl or C3-C6alkynyl; or
R97 and R98 together are C4- or C5-alkylene in which one carbon atom may have been replaced by oxygen or by sulfur, or one or two carbon atoms may have been replaced by —NR101—;
R101 is hydrogen or C1-C4alkyl;
r is 0 or 1; and
s is 0, 1 or 2,

or of a compound of formula XVIII



wherein R103 is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl or C3-C6alkynyl; and R104, R105 and R106 are each independently of the others hydrogen, C1-C6alkyl, C3-C6cycloalkyl or C1-C6alkoxy, with the proviso that one of the substituents R104, R105 and R106 is other than hydrogen;

or of a compound of formula XIX



wherein Z5 is N or CH, n is 0, 1, 2 or 3 when Z5 is N, and n is 0, 1, 2, 3 or 4 when Z5 is CH, R107 is halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, nitro, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkoxycarbonyl, phenyl or phenoxy, or phenyl or phenoxy substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
R108 is hydrogen or C1-C4alkyl, R109 is hydrogen, C1-C4alkyl, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C1-C4alkylthio-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-4alkenyloxy-C1-C4alkyl or C1-C4-alkynyloxy-C1-C4alkyl;

or of a compound of formula XX



wherein Z6 is oxygen or N—R110 and R110 is a group of formula




wherein R111 and R112 are each independently of the other cyano, hydrogen, C1-C4alkyl, C3-C6-cycloalkyl, C2-C6alkenyl, aryl, phenyl or heteroaryl, or phenyl, aryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;

or of a compound of formula XXI



wherein Z7 is oxygen, sulfur, S═O, SO2 or CH2, R113 and R114 are each independently of the other hydrogen, halogen or C1-C4alkyl, W2 and W3 are each independently of the other CH2COOR115 or COOR0115 or together are a group of formula —(CH2)C(O)—O—C(O)—(CH2)—, and R115 and R0115 are each independently of the other hydrogen, C1-C4alkyl, C2-C4alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C4haloalkyl, or a metal cation or an ammonium cation;

or of a compound of formula XXII



wherein R119 and R120 are each independently of the other hydrogen, halogen or C1-C4haloalkyl, R121 is hydrogen, C1-C4alkyl, C3-C4alkenyl, C3-C4alkynyl, C1-C4haloalkyl, C3-C6cycloalkyl, a metal cation or an ammonium cation, Z8 is N, CH, C—F or C—Cl and W4 is a group of formula




wherein R122 and R123 are each independently of the other hydrogen or C1-C4alkyl and R124 and R125 are each independently of the other hydrogen or C1-C4alkyl;

or of a compound of formula XXIII



wherein R126 is hydrogen, cyano, halogen, C1-C4alkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxycarbonyl, C1-C4alkylthiocarbonyl, —NH—R128, —C(O)NH—R0128, aryl or heteroaryl, or aryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
R127 is hydrogen, cyano, nitro, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4thioalkyl; and
R128 and R0128 are each independently of the other C1-C4alkyl, C1-C4haloalkyl, C3-C4alkenyl, C3-C4alkynyl, C3-C4cycloalkyl, aryl or heteroaryl, or aryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, formyl, C1-C4alkylcarbonyl or C1-C4alkylsufonyl;

or of a compound of formula XXIV



wherein R129 and R130 are each independently of the other hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, mono-C1-C8- or di-C1-C8-alkylamino, C3-C6cycloalkyl, C1-C4thioalkyl, phenyl or heteroaryl, R131 has the meanings of R129 and in addition is OH, NH2, halogen, di-C1-C4aminoalkyl, C1-C4alkylthio, C1-C4alkylsulfonyl or C1-C4alkoxycarbonyl, R132 has the meanings of R129 and in addition is cyano, nitro, carboxyl, C1-C4alkoxycarbonyl, di-C1-C4aminoalkyl, C1-C4alkylthio, C1-C4alkylsulfonyl, SO2—OH, i-C1-C4aminoalkylsulfonyl or C1-C4alkoxysulfonyl, R133 has the meanings of R129 and in addition is OH, NH2, halogen, di-C1-C4aminoalkyl, pyrrolidin-1-yl, piperidin-1-yl, morpholin-1-yl, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkoxycarbonyl, phenoxy, naphthoxy, phenylamino, benzoyloxy or phenylsulfonyloxy;

or of a compound of formula XXV



wherein R134 is hydrogen, C4alkyl, C1-C4haloalkyl, C2-C4alkenyl, C2-C4alkynyl or C1-C4alkoxy-C1-C4alkyl, R135 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4alkoxy and R136 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4alkoxy, with the proviso that R135 and R136 are not simultaneously hydrogen,

or of formula XXVI




wherein
R143 is hydrogen, an alkali metal cation, alkaline earth metal cation, sulfonium cation or ammonium cation or ethyl;

or of formula XXVII



wherein R144 and R145 are each independently of the other hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl or C3-C6cycloalkyl;
R146 is hydrogen, halogen, C1-C4alkyl, C1-C6haloalkyl or C1-C6haloalkoxy;
R147 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4alkoxycarbonyl or nitro;
n1 is 0, 1, 2 or 3; and
m is 1 or 2;

or of formula XXVIII




wherein
R148 is hydrogen, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylthio, C3-C8cycloalkyl, phenyl, phenyl-C1-C6alkyl or heteroaryl; wherein the said groups may be substituted by halogen, cyano, nitro, amino, hydroxy, carbonyl, carboxyl, formyl, carbonamide or by sulfonamide;
R149 is hydrogen, C1-C6alkyl or C1-C4haloalkyl;
each R150 is independently of any other(s) hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, cyano, nitro, formyl or carboxyl;
R151 is hydrogen, C1-C6alkyl or C1-C4haloalkyl;
each R152 is independently of any other(s) hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, cyano, nitro, formyl or carboxyl;
o is 0, 1, or 2, and
p is 0, 1 or 2;

or of formula XXIX




wherein
R159 is hydrogen, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, phenyl-C1-6alkylcarbonyl, phenylcarbonyl, C1-6alkylsulfonyl, C1-6alkenylsulfonyl or phenylsulfonyl, wherein the afore-mentioned hydrocarbon groups may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
R153 is hydrogen, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, C3-8cycloalkyl, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, C1-6alkylsulfonyl, C1-6alkenylsulfonyl or phenylsulfonyl, wherein the afore-mentioned hydrocarbon groups may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
R154 is hydrogen, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, C3-8cycloalkyl, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, C1-6alkylsulfonyl, C1-6alkenylsulfonyl or phenylsulfonyl, wherein the afore-mentioned hydrocarbon groups may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
R155, R156, R157, and R158 are each independently of the others hydrogen, halogen, amino, C1-3alkylamino, C1-6dialkylamino, hydroxy, cyano, nitro, formyl, carboxyl, C1-6alkoxy, C1-6haloalkoxy, C1-6alkylcarbonyl, C1-6alkoxycarboxyl, C1-6alkyl, C1-6haloalkyl, C1-6alkenyl or C1-6alkynyl;
or R153 and R158, together with the ring atoms to which they are bonded, form a five- or six-membered, partially saturated or unsaturated ring that may contain up to 2 identical or different hetero atoms from the group oxygen, sulfur and nitrogen, it being possible for that ring to be substituted by an oxo radical.

2. A composition according to claim 1 comprising a herbicide-antagonistically effective amount of a safener of the formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV or XXV.

3. A method of selectively controlling weeds and grasses in crops of useful plants that comprises treating the useful plants, the seeds or the cuttings thereof or the area of cultivation thereof with a) a herbicidally effective amount of a herbicide of formula I




wherein
R1 and R3 are each independently of the other ethyl, haloethyl, ethynyl C1-C2alkoxy, C1-C2haloalkoxy, C1-C2alkylcarbonyl, C1-C2hydroxyalkyl or C1-C2alkoxycarbonyl;
Q is a group







R4 and R5 are each independently of the other C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C2-C10—N-alkoxyiminoalkyl, C2-C10alkoxycarbonylalkyl, C1-C10aminoalkyl, C3-C10dialkylaminoalkyl, C2-C10alkylaminoalkyl, C1-C10cyanoalkyl, C4-C10cycloalkylalkyl, C1-C10phenylalkyl, C1-C10heteroarylalkyl, C1-C10phenoxyalkyl, C1-C10heteroaryloxyalkyl, C1-C10alkylideneaminooxyalkyl, C1-C10nitroalkyl, C1-C10trialkylsilylalkyl, C2-C10alkylaminocarbonylalkyl, C2-C10dialkylaminocarbonylalkyl, C2-C10alkylaminocarbonyloxyalkyl, C3-C10dialkylaminocarbonyloxalkyl, C2-C10alkoxycarbonylaminoalkyl, C1-C10-N-alkoxycarbonyl-N-alklaminoalkyl, C1-C10cycloalkyl, aryl or heteroaryl; or
R4 and R5, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur and that, in addition, may contain a fused or spiro-bound alkylene or alkenylene chain consisting of from 2 to 6 carbon atoms, which chain may in turn contain one or two hetero atoms selected from oxygen and sulfur, wherein the cyclic group may be substituted by phenyl or benzyl, which in turn may be substituted by halogen, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, hydroxy, C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy, C1-C6haloalkoxy or by nitro;
R2, R6 and R32 are each independently of the others C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalky, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R7, R31 and R33 are each independently of the others hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C2-C10alkoxyalkyl;
R8 is hydrogen, C1-C10alkyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10-alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
R6 and R7 or R8 and R31 or R32 and R33, together with the atom to which they are bonded, form a saturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur; or R6 and R8, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R9, R10, R11 and R12 are each independently of the others C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
R9 and R11 or R8 and R10, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R13, R14, R34 and R35 are each independently of the others C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
R13 and R14 or R34 and R35, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R15 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C2-C10alkoxycarbonylalkyl, C1-C10aminoalkyl, C3-C10dialkylaminoalkyl, C2-C10alkylaminoalkyl, C1-C10cyanoalkyl, C4-C10cycloalkylalkyl, C1-C10phenylalkyl, C1-C10heteroarylalkyl, C1-C10phenoxyalkyl, C1-C10heteroaryloxyalkyl, C1-C10nitroalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R16 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R17 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R18 is hydrogen, C2-C10alkenyl, C2-C10alkynyl, C1-C10alkyl or C1-C10alkoxyalkyl; or
R17 and R18, together with the atoms to which they are bonded, form a 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
Y is oxygen, sulfur, C—R19 or N—R36;
R19 and R36 are each independently of the other C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, phenyl or heteroaryl; or
R18 and R19 or R18 and R36, together with the atom to which the are bonded, form a saturated 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
G1, G2, G3, G4, G5, G6, G7, G8, G9 and G10 are each independently of the others hydrogen, —C(X1)—R20, —C(X2)—X3—R21, —C(X4)—N(R22)—R23, —SO2—R24, an alkali metal cation, alkaline earth metal cation, sulfonium cation or ammonium cation, —P(X5)(R25)—R26 or —CH2—X6—R27;
X1, X2, X3, X4, X5 and X6 are each independently of the others oxygen or sulfur;
R20, R21, R22 and R23 are each independently of the others hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl, C4-C10alkenyloxyalkyl, C4-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C1-C5alkylsulfoxyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylideneaminooxy-C1-C5alkyl, C1-C5alkylcarbonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminocarbonyl-C1-C5alkyl, C1-C5alkylcarbonylamino-C1-C5alkyl, C1-C5alkylcarbonyl-(C2-C5alkyl)-aminoalkyl, C3-C6trialkylsilyl-C1-C5alkyl, phenyl-C1-C5alkyl, heteroaryl-C1-C5alkyl, phenoxy-C1-C5alkyl, heteroaryloxy-C1-C5alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or heteroaryl or heteroarylamino, or heteroaryl or heteroarylamino substituted by C1-C3alkyl, C1C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diheteroarylamino, or diheteroaryiamino substituted by C1-C3alky, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, phenylamino, or phenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diphenylamino, or diphenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano, or by nitro, or C3-C7cycloalkylamino, di-C3-C7cycloalkylamino or C3-C7cycloalkoxy;
R24, R25 and R26 are hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl, C4-C10alkenyloxyalkyl, C4-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C1-C5alkylsulfoxyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylideneaminooxy-C1-C5alkyl, C1-C5alkylcarbonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminocarbonyl-C1-C5alkyl, C1-C5alkylcarbonylamino-C1-C5alkyl, C1-C5alkylcarbonyl-(C2-C5alkyl)-aminoalkyl, C3-C6trialkylsilyl-C1-C5alkyl, phenyl-C1-C5alkyl, heteroaryl-C1-C5alkyl, phenoxy-C1-C5alkyl, heteroaryloxy-C1-C5alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or heteroaryl or heteroarylamino, or heteroaryl or heteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diheteroaiylamino, or diheteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, phenylamino, or phenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diphenylamino,or diphenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or C3-C7cycloalkylamino, di-C3-C7cycloalklamino, C3-C7cloalkoxy, C1-C10alkoxy, C1-C10haloalkoxy, C1-C5alkylamino, C2-C8dialkylamino, benzyloxy or phenoxy, wherein the benzyl and phenyl groups may in turn be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
R27 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl, C4-C10alkenyloxalkyl, C4-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C1-C5alkylsulfoxyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylideneaminooxy-C1-C5alkyl, C1-C5alkylcarbonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminocarbonyl-C1-C5alkyl, C1-C5alkylcarbonylamino-C1-C5alkyl, C1-C5alkylcarbonyl-(C2-C5alkyl)-aminoalkyl, C3-C6trialkylsilyl-C1-C5alkyl, phenyl-C1-C5alkyl, heteroaryl-C1-C5alkyl, phenoxy-C1-C5alkyl, heteroarloxy-C1-C5alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or heteroaryl or heteroarylamino, or heteroaryl or heteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diheteroarylamino, diheteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or phenylamino, phenylamino substituted by C1-C3alkyl, C1-C3haloalkoxy, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diphenylamino, diphenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, C3-C7cycloalkylamino, di-C3-C7cycloalkylamino, C3-C7cycloalkoxy or C1-C10alkylcarbonyl;
Y2 is oxygen, sulfur, C—R140—R141 or N—R142,
R55 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10-alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10-alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R137 is hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C1-C10alkoxyalkyl; or
R55 and R137, together with the atoms to which they are bonded, form a 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R138 and R139 are each independently of the other hydrogen C1-C10alkyl, C2-C10alkenyl, C2-C10-alkynyl or C2-C10alkoxyalkyl; and
R140 and R141 are each independently of the other hydrogen, C1-C10alkyl, C2-C10alkenyl, C1-C10alkynyl or C1-C10alkoxyalkyl; or
R55 and C—R140, together with the atoms to which they are bonded, form a saturated or unsaturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R142 is hydrogen, C1-C10alkyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
R55 and N—R142, together with the atoms to which they are bonded, form a saturated or unsaturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;

or an agronomically tolerable salt, isomer or enantiomer of such a compound; and
b) a herbicide-antagonistically effective amount either of a compound of formula X





wherein
R37 is hydrogen C1-C8alkyl, or C1-C8alkyl substituted by C1-C6alkoxy or by C3-C6alkenyloxy; and X7 is hydrogen or chlorine; or of a compound of formula XI





wherein
E is nitrogen or methine;
R38 is —CCl3, phenyl or phenyl substituted by halogen;
R39 and R40 are each independently of the other hydrogen or halogen; and
R41 is C1-C4alkyl; or of a compound of formula XII




wherein R44 and R45 are each independently of the other hydrogen or halogen, and R46, R47 and R48 are each independently of the others C1-C4alkyl, or of a compound of formula XIII




R51 and R52 are each independently of the other hydrogen, C1-C8alkyl, C3-C8cycloalkyl, C3-C6alkenyl, C3-C6alkynyl,





or C1-C4alkyl substituted by C1-C4alkoxy or by




or R51 and R52 together form a C4-C6alkylene bridge that may be interrupted by oxygen, sulfur, SO, SO2, NH or by —N(C1-C4alkyl)-;
R53 is hydrogen or C1-C4alkyl;
R49 is hydrogen, halogen, cyano, trifluoromethyl, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj, —CONRkRm, —CORn, —SO2NRkRm or —OSO2—C1-C4alkyl;
Rg is hydrogen, halogen, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj, —CONRkRm, —CORn, —SO2NRkRm, —OSO2—C1-C4alkyl, C1-C6alkoxy, or C1-C6alkoxy substituted by C1-C4alkoxy or by halogen, C3-C6alkenyloxy, or C3-C6alkenyloxy substituted by halogen, or C3-C6alkynyloxy, or R49 and R50 together form a C3-C4alkylene bridge that may be substituted b halogen or b C1-C4alkyl, or together form a C3-C4alkenylene bridge that may be substituted by halogen or by C1-C4alkyl, or together form a C4alkadienylene bridge that may be substituted by halogen or by C1-C4alkyl;
R50 and Rh are each independently of the other hydrogen, halogen, C1-C4alkyl, trifluoromethyl, C1-C6alkoxy, C1-C6alkylthio or —COORj;
Rg is hydrogen, halogen, nitro, C1-C4alkyl or methoxy; Rd is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm;
Re is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy, or Rd and Re together form a C3-C4alkylene bridge;
Rp is hydrogen, halogen, C1-C4alkyl, —COORj; trifluoromethyl or methoxy; Rq is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm; or Rp and Rq together form a C3-C4alkylene bridge;
Rp is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy; Rq is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm; or Rr and Rs together form a C3-C4alkylene bridge;
Rt is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy; Ru is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm; or Rv and Ru together form a C3-C4alkylene bridge;
Rf are Rv are hydrogen, halogen or C1-C4alkyl;
Rx and Ry are each independently of the other hydrogen, halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, —COOR54, trifluoromethyl, nitro or cyano;
Rj, and Rk and Rm are each independently of the others hydrogen or C1-C4alkyl; or
Rk and Rm together form a C4-C6alkylene bridge that may be interrupted by oxygen, NH or by —N(C1-C4alkyl)-;
Rn is C1-C4alkyl, phenyl, or phenyl substituted by halogen, C1-C4alkyl, methoxy, nitro or by trifluoromethyl;
R54 is hydrogen, C1-C10alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylthio-C1-C4alkyl, di-C1-C4alkylamino-C1-C4alkyl, halo-C1-C8alkyl, C2-C8alkenyl, halo-C2-C8alkenyl, C3-C8alkynyl, C3-C7cycloalkyl, halo-C3-C7cycloalkyl, C1-C8alkylcarbonyl, allylcarbonyl, C3-C7cycloalkylcarbonyl, benzoyl, which is unsubstituted or substituted on the phenyl ring identically or differently up to three times by halogen, C1-C4alkyl, halo-C1-C4alkyl, halo-C1-C4alkoxy or C1-C4alkoxy; or furoyl, thienyl; or C1-C4alkyl substituted by phenyl, halophenyl, C1-C4alkylphenyl, C1-C4alkoxyphenyl, halo-C1-C4alkylphenyl, halo-C1-C4alkoxyphenyl, C1-C6alkoxycarbonyl, C1-C4alkoxy-C1-C8alkoxycarbonyl, C3-C8alkenyloxycarbonyl, C3-C8alkynyloxycarbonyl, C1-C8alkylthiocarbonyl, C3-C8alkenylthiocarbonyl, C3-C8alkynylthiocarbonyl, carbamoyl, mono-C1-C4alkylaminocarbonyl, di-C1-C4alkylaminocarbonyl; or phenylaminocarbonyl, which is unsubstituted or substituted on the phenyl identically or differently up to three times by halogen, C1-C4alkyl, halo-C1-C4alkyl, halo-C1-C4alkoxy or C1-C4alkoxy or once by cyano or nitro; or dioxolan-2-yl, which is unsubstituted or substituted by one or two C1-C4alkyl radicals, or dioxan-2-yl, which is unsubstituted or substituted by one or two C1-C4alkyl radicals, or C1-C4alkyl, which is substituted by cyano, nitro, carboxyl or by C1-C8alkylthio-C1-C8alkoxycarbonyl;

or of a compound of formula XIV




wherein R56 and R57 are each independently of the other C1-C6alkyl or C2-C6alkenyl; or R56 and R57 together are




R58 and R59 are each independently of the other hydrogen or C1-C6alkyl; or R56 and R57 together are



R60 and R61 are each independently of the other C1-C4alkyl, or R60 and R61 together are —(CH2)5—;
R62 is hydrogen, C1-C4alkyl or





or R56 and R57 together are



R63, R64, R65, R66, R67, R68, R69, R70, R71, R72, R73, R74, R75, R76, R77 and R78 are each independently of the others hydrogen or C1-C4alkyl;

or of a compound of formula XV



wherein R80 is hydrogen or chlorine and R79 is cyano or trifluoromethyl;

or of a compound of formula XVI



wherein R81 is hydrogen or methyl;

or of a compound of formula XVI



wherein R81 is hydrogen or methyl;

or of a compound of formula XVII




wherein
R82 is hydrogen, C1-C4alkyl, or C1-C4alkyl substituted by C1-C4alkyl-X2— or by C1-C4haloalkyl-X2—, or is C1-C4haloalkyl, nitro, cyano, —COOR85, —NR86R87, —SO2NR88R89 or —CONR90R91;
R83 is hydrogen, halogen, C1-C4alkyl, trifluoromethyl, C1-C4alkoxy or C1-C4haloalkoxy;
R84 is hydrogen, halogen or C1-C4alkyl;
U, V, W1 and Z4 are each independently of the others oxygen, sulfur, C(R92)R93, carbonyl, NR94, or a group





wherein R102 is C2-C4alkenyl or C2-C4alkynyl; with the provisos that
a) at least one of the ring members U, V, W1 or Z4 is carbonyl, and a ring member adjacent to that ring member or to those ring members is the group





that group appearing only once; and
b) two adjacent ring members U and V, V and W1 and W1 and Z4 cannot simultaneously be oxygen;
R95 and R96 are each independently of the other hydrogen or C1-C8alkyl; or
R95 and R96 together form a C2-C6alkylene group;
A1 is R99—Y1— or —NR97R98;
X2 is oxygen or —S(O)s;
Y1 is oxygen or sulfur;
R99 is hydrogen, C1-C8alkyl, C1-C8haloalkyl, C1-C4alkoxy-C1-C8alkyl, C3-C6alkenyloxy-C1-C8alkyl, or phenyl-C1-C8alkyl in which the phenyl ring may be substituted by halogen, C1-C4alkyl, trifluoromethyl, methoxy or by methyl-S(O)s—, or is C3-C6alkenyl, C3-C6haloalkenyl, phenyl-C3-C6-alkenyl, C3-C6alkynyl, phenyl-C3-C6alkynyl, oxetanyl, furyl or tetrahydrofuryl;
R85 is hydrogen or C1-C4alkyl;
R86 is hydrogen, C1-C4alkyl or C1-C4alkylcarbonyl;
R87 is hydrogen or C1-C4alkyl; or
R86 and R87 together form a C4- or C5-alkylene group;
R88, R89, R90 and R91 are each independently of the others hydrogen or C1-C4alkyl; or R88 together with R89, or R90 together with R91, are each independently of the other C4- or C5-alkylene in which one carbon atom may have been replaced by oxygen or by sulfur, or one or two carbon atoms may have been replaced by —NR100—;
R92, R100 and R93 are each independently of the others hydrogen or C1-C8alkyl; or
R92 and R93 together are C2-C6alkylene;
R94 is hydrogen or C1-C8alkyl;
R97 is hydrogen, C1-C8alkyl, phenyl or phenyl-C1-C8alkyl, wherein the phenyl rings may be substituted by fluorine, chlorine, bromine, nitro, cyano, —OCH3, C1-C4alkyl or by CH3SO2—, or is C1-C4alkoxy-C1-C8alkyl, C3-C6alkenyl or C3-C6alkynyl;
R98 is hydrogen, C1-C8alkyl, C3-C6alkenyl or C3-C6alkynyl; or
R97 and R98 together are C4- or C5-alkylene in which one carbon atom may have been replaced by oxygen or by sulfur, or one or two carbon atoms may have been replaced by —NR101—;
R101 is hydrogen or C1-C4alkyl;
r is 0 or 1; and
s is 0, 1 or 2,

or of a compound of formula XVIII



wherein R103 is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl or C3-C6alkynyl; and R104, R105 and R106 are each independently of the others hydrogen, C1-C6alkyl, C3-C6cycloalkyl or C1-C6alkoxy, with the proviso that one of the substituents R104, R105 and R106 is other than hydrogen;

or of a compound of formula XIX



wherein Z5 is N or CH, n is 0, 1, 2 or 3 when Z5 is N, and n is 0, 1, 2, 3 or 4 when Z5 is CH, R107 is halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, nitro, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkoxycarbonyl, phenyl or phenoxy, or phenyl or phenoxy substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
R108 is hydrogen or C1-C4alkyl, R109 is hydrogen, C1-C4alkyl, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C1-C4alkylthio-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkenyloxy-C1-C4alkyl or C1-C4-alkynyloxy-C1-C4alkyl;

or of a compound of formula XX



wherein Z6 is oxygen or N—R110 and R110 is a group of formula




wherein R111 and R112 are each independently of the other cyano, hydrogen, C1-C4alkyl, C3-C6-cycloalkyl, C2-C6alkenyl, aryl, phenyl or heteroaryl, or phenyl, aryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;

or of a compound of formula XXI



wherein Z7 is oxygen, sulfur, S═O, SO2 or CH2, R113 and R114 are each independently of the other hydrogen, halogen or C1-C4alkyl, W2 and W3 are each independently of the other CH2COOR115 or COOR0115 or together are a group of formula —(CH2)C(O)—O—C(O)—(CH2)—, and R115 and R0115 are each independently of the other hydrogen, C1-C4alkyl, C2-C4alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C4haloalkyl, or a metal cation or an ammonium cation;

or of a compound of formula XXII



wherein R119 and R120 are each independently of the other hydrogen, halogen or C1-C4haloalkyl, R121 is hydrogen, C1-C4alkyl, C3-C4alkenyl, C3-C4alkynyl, C1-C4haloalkyl, C3-C6cycloalkyl, a metal cation or an ammonium cation, Z8 is N, CH, C—F or C—Cl and W4 is a group of formula





wherein R122 and R123 are each independently of the other hydrogen or C1-C4alkyl and R124 and R125 are each independently of the other hydrogen or C1-C4alkyl;
or of a compound of formula XXIII



wherein R126 is hydrogen, cyano, halogen, C1-C4alkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxycarbonyl, C1-C4alkylthiocarbonyl, —NH—R128, —C(O)NH—R0128, aryl or heteroaryl, or aryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
R127 is hydrogen, cyano, nitro, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4thioalkyl; and
R128 and R0128 are each independently of the other C1-C4alkyl, C1-C4haloalkyl, C3-C4alkenyl, C3-C4alkynyl, C3-C4cycloalkyl, aryl or heteroaryl, or aryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, formyl, C1-C4alkylcarbonyl or C1-C4alkylsufonyl;

or of a compound of formula XXIV



wherein R129 and R130 are each independently of the other hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, mono-C1-C8- or di-C1-C8-alkylamino, C3-C6cycloalkyl, C1-C4thioalkyl, phenyl or heteroaryl, R131 has the meanings of R129 and in addition is OH, NH2, halogen, di-C1-C4aminoalkyl, C1-C4alkylthio, C1-C4alkylsulfonyl or C1-C4alkoxycarbonyl, R132 has the meanings of R129 and in addition is cyano, nitro, carboxyl, C1-C4alkoxycarbonyl, di-C1-C4aminoalkyl, C1-C4alkylthio, C1-C4alkylsulfonyl, SO2—OH, i-C1-C4aminoalkylsulfonyl or C1-C4alkoxysulfonyl, R133 has the meanings of R129 and in addition is OH, NH2, halogen, di-C1-C4aminoalkyl, pyrrolidin-1-yl, piperidin-1-yl, morpholin-1-yl, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkoxycarbonyl, phenoxy, naphthoxy, phenylamino, benzoyloxy or phenylsulfonyloxy;

or of a compound of formula XXV



wherein R134 is hydrogen, C4alkyl, C1-C4haloalkyl, C2-C4alkenyl, C2-C4alkynyl or C1-C4alkoxy-C1-C4alkyl, R135 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4alkoxy and R136 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4alkoxy, with the proviso that R135 and R136 are not simultaneously hydrogen,

or of formula XXVI




wherein
R143 is hydrogen, an alkali metal cation, alkaline earth metal cation, sulfonium cation or ammonium cation or ethyl;

or of formula XXVII



wherein R144 and R145 are each independently of the other hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl or C3-C6cycloalkyl;
R146 is hydrogen, halogen, C1-C4alkyl, C1-C6haloalkyl or C1-C6haloalkoxy;
R147 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4alkoxycarbonyl or nitro;
n1 is 0, 1, 2 or 3; and
m is 1 or 2;

or of formula XXVIII




wherein
R148 is hydrogen, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylthio, C3-C8cycloalkyl, phenyl, phenyl-C1-C6alkyl or heteroaryl; wherein the said groups may be substituted by halogen, cyano, nitro, amino, hydroxy, carbonyl, carboxyl, formyl, carbonamide or by sulfonamide;
R149 is hydrogen, C1-C6alkyl or C1-C4haloalkyl;
each R150 is independently of any other(s) hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, cyano, nitro, formyl or carboxyl;
R151 is hydrogen, C1-C6alkyl or C1-C4haloalkyl;
each R152 is independently of any other(s) hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, cyano, nitro, formyl or carboxyl;
o is 0, 1, or 2, and
p is 0, 1 or 2;

or of formula XXIX




wherein
R159 is hydrogen, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, phenyl-C1-6alkylcarbonyl, phenylcarbonyl, C1-6alkylsulfonyl, C1-6alkenylsulfonyl or phenylsulfonyl, wherein the afore-mentioned hydrocarbon groups may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
R153 is hydrogen, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, C3-8cycloalkyl, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, C1-6alkylsulfonyl, C1-6alkenylsulfonyl or phenylsulfonyl, wherein the afore-mentioned hydrocarbon groups may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
R154 is hydrogen, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, C3-8cycloalkyl, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, C1-6alkylsulfonyl, C1-6alkenylsulfonyl or phenylsulfonyl, wherein the afore-mentioned hydrocarbon groups may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
R155, R156, R157, and R158 are each independently of the others hydrogen, halogen, amino, C1-3alkylamino, C1-6dialkylamino, hydroxy, cyano, nitro, formyl, carboxyl, C1-6alkoxy, C1-6haloalkoxy, C1-6alkylcarbonyl, C1-6alkoxycarboxyl, C1-6alkyl, C1-6haloalkyl, C1-6alkenyl or C1-6alkynyl;
or R153 and R158, together with the ring atoms to which they are bonded, form a five- or six-membered, partially saturated or unsaturated ring that may contain up to 2 identical or different hetero atoms from the group oxygen, sulfur and nitrogen, it being possible for that ring to be substituted by an oxo radical.

4. A method according to claim 3 comprising treating the useful plants, the seeds or cuttings thereof or the area of cultivation thereof with a herbicide-antagonistically effective amount of a safener of the formula X, XI, XII, XIII, XIV, XV, XVI, XVII, XVIII, XIX, XX, XXI, XXII, XXIII, XXIV or XXV.

5. A composition according to claim 1 that comprises spray tank adjuvants.