Title of Invention

A HERBICIDAL COMPOSITION

Abstract Abstract: Synergistic herbicidal compositions comprising herbicides from the group of the hydroxyphenylpyruvate dioxygenase inhibitors s Herbicidai compositions comprising A) at least one compound from the group of the hydroxyphenylpyruvate dioxygenase Inhibitors and B) at (east one compound from the group B-a) herbicides which are selectively active in cereals against monocotyledonous and/or dicotyledonous harmful plants, B-b) herbicides which are selectively active in corn against monocotyledonous and/or dicotyledonous harmful plants, B-c) herbicides which are selectively active in rice against monocotyledonous and/or dicotyledonous harmful plants, B-d) herbicides which are nonselectively active in land which is not under cultivation and/or selectively active in transgenic crops against monocotyledonous and/or dicotyledonous harmful plants are described. The activity of these compositions is superior to that of the herbicides applied on their own.
Full Text



Synergistic herbicidal compositions comprising herbicides from the group of the hydroxyphenylpyruvate dioxygenase inhibitors
The invention is in the field of crop protection compositions which can be used against undesirable vegetation and which comprise, as active compounds, a combination of at least two herbicides.
More specifically, the invention relates to herbicidal compositions which, as active compound, comprise a herbicide from the group of the hydroxyphenylpyruvate dioxygenase inhibitors in combination with at least one further herbicide.
Herbicides from the abovementioned group of the hydroxyphenylpyruvate dioxygenase inhibitors are known from numerous documents. Recently disclosed inhibitors of this type usually carry a substituted benzoyl radical on a likewise substituted radical from the group consisting of cyclohexanedione, pyrazole, isoxazole, isothiazoie and 3-oxoproplonitrile. Thus, WO 97/23135 describes benzoytpyrazoles, EP-A 0 810 227 describes benzoyl isoxazoles and WO 98/29406 describes benzoyl-cyclohexanediones having in each case herbicidal action. Further herbicidal benzoyl derivatives are known from WO 99/06259. This document also indicates the mechanism of action, which is the same as for the benzoyl derivatives described in the present invention.
In practice, however, the use of the benzoyl derivatives known from these publications has frequently been associated with disadvantages. Thus, the herbicidal activity of the known compounds is not always satisfactory, or, in the case of satisfactory herbicidal activity, undesirable damage to the useful plants is observed.
The activity of herbicides depends inter alia on the type of herbicide used, its application rate, the preparation, the harmful plants to be controlled in each case, climatic and soil conditions, etc. A further criterion is the persistency or the rate at which the herbicide is degraded. Changes in the sensitivity of harmful plants to an active compound which may occur on

prolonged use or in specific geographical areas may also have to be taken into account. Such changes manifest themselves by a more or less pronounced loss in activity and can only be compensated under certain conditions by higher herbicide application rates.
Owing to the large number of possible influencing factors, there is virtually no individual active compound which has all the desired properties for different requirements, in particular with respect to the species of harmful plant and the climatic zones. Furthermore, there is the permanent object to achieve the desired effect using more and more reduced herbicide application rates. A lower application rate reduces not only the amount of active compound required for the application, but generally also reduces the amount of formulation auxiliaries required. Both reduce the economical expense and improve the ecological compatibility of the herbicide treatment.
A frequently used method for improving the use profile of a herbicide is the combination o1 the active compound with one or more other active compounds which contribute the desired additional properties. However, the combined use of a plurality of active compounds is frequently associated with phenomena of physical and biological incompatibility, for example insufficient stability of a joint formulation, decomposition of an active compound or antagonism of the active compounds. What is desired are, in contrast, active compound combinations having a favorable activity profile, high stability and, if possible, synergistically enhanced activity, thus permitting the application rate to be reduced, compared with the individual application of the active compounds to be combined.
EP-A 0 768 033, WO 97/23135, ZA 9 510 980 and WO 98/28981 each disclose combinations o1 specific benzoylpyrazoies with other herbicides. US 5,912,207 describes herblcidal preparations comprising metal chelates of specific benzoylcyclohexanediones.
It is an object of the present invention to provide herblcidal compositions having better properties than those of the prior art.

The invention provides herbicidal compositions, comprising an effective amount of
A) at least one compound of formula (I) and its agriculturally customary salts (Component A)

Z Is a five- to ten-membered monocyclic or bicyclic saturated, partially saturated, fully unsaturated or aromatic ring which is attached via carbon or nitrogen and which, In addition to carbon atoms, contains 1, 2, 3 or 4 heteroatoms from the group

consisting of oxygen, sulfur and nitrogen and which is unsubstituted or mono- or polysubstituted by halogen, cyano, nitro, cyano-(C1-C4)-alkyl, CO-R', (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C3-C8)-cycloaIkyl, {C1-C4)-alkoxy, halo-(C1-C4)-alkoxy, {C1-C4)-aIkylthio, halo-(C1-C4)-alkylthio, di-(C1-C4)-alkylamino, by phenyl which is unsubstituted or mono- or polysubstituted by halogen, cyano, nitro, (C1-C4)-alkyl or halo-(C1-C4)-alkyl or by an oxo group;

Z is (C3-C12)-cycloalkyloxy-(C1-C4)-alkyl, aryloxy-{C1-C4)-alkyl,
heteroaryloxy-(C1-C4)-alkyl, heterocyclyl-(C1-C4)-alkyl, halo-(C1-C4)-alkoxy-(C1-C4)-alkyl, aryl-(C1-C4)-alkoxy-(C1-C4)-alkyl, heteroaryl-(C1-C4)-alkoxy-(C1-C4)-alkyl, heterocyclyl-(C1-C4)-alkoxy-(C1-C4)-alkyl, aryl-(C3-C8)-cycloalkylthio-{C1-C4)-alkyi,
heteroaryl-(C3-C8)-cycIoalkylthio-(C1-C4)-alkyl, heterocyclyl-(C3-C8)-
cycloalkylthio-(C1-C4)-aIkyl, {C3-C8)-cycIoalkylsulfinyl-{C1-C4)-alkyl,
(C3-C8)-cycloaIkylsulfonyi-(C1-C4)-alkyl, (C2-CsJ-cycloalkylamino-
(C1-C4)-alkyl, (C3-C8)-cycloalkylsuifony!oxy-(C1-C4)-a!kyl, (Ca-Ca)-
cycloalkyIsulfonylamino-(C1-C4)-alkyl, {C3-C8)-cycloalkylcarbonyl-
(C1 -C4)-alkyl, {C3-C8)-cycloalkylcarbonyloxy-(C1 -C4)-alkyi, (C3-C8)-
cycloa!koxycarbonyl-(C1-C4)-alkyl, (Ca-Cgl-cycloalkyfcarbonylamino-
(C1-C4)-alkyl, (C3-C8)-cycloalkylaminocarbonyl-(C1-C4)-alkyl,
(C4-C12)-cycloaIkyl-{C1 -C4)-alkyl, (C4-C12)-cycloalkylthio-(C1 -C4)-
alkyl, (C4-C12)-cycloa!kylsulfinyl-(C1-C4)-alkyl, (C4-C12)-cyclo-
alkylsulfonyl-(C1-C4)-alkyl, (C4-C12)-cycloaikylamino-(C1-C4)-alkyl,
{C4-C12)-cycloalkyIsulfonyloxy-(C1-C4)-alkyl, (C4-C12)-cycloaIkyl-
suIfonylamino-{C1-C4)-alkyl, (C4-C12)-cycloa!kylcarbonyl-(C1-C4)-
alkyl, (C4-C12)-cycloalkylcarbonyloxy-(C1-C4)-alkyl, (C4-C12)-
cycloalkoxycarbonyl-(C1-C4)-alkyl, (C4-C12)-cycloalky!carbonyl-
amino-(C1-C4)-alkyl, {C4-C12)-cycloaIkyiaminocarbonyl-(C1-C4)-alkyl, arylthio-(C1-C4)-aIkyl, arylsulfinyl-{C1-C4)-alkyi, arylsulfonyl-(C1-C4)-alkyl, arylamino-(C1-C4)-alkyl, ary!sulfonyloxy-(C1-C4)-alkyl, ary!sulfonylamino-(C1-C4)-alkyl, atylcarbonyl-(C1-C4)-alkyl, aryl-carbonyloxy-(C1-C4)-alkyl, aryloxycarbonyl-(C1-C4)-alkyl, aryi-

neieroarylcarbonyl-{Gi-G4)-alKyl, het6roarylcarbonyloxy-(C1-C4)-
alkyl, heteroaryloxycarbonyl-(C1-C4)-alkyl, heteroarylcarbonylamino-
(C1-C4)-aIkyl, heteroaryIaminocarbonyl-(C1-C4)-a!kyl, heterocyclyl-
thio-(C1-C4)-aIkyI, heterocyclylsulfinyI-(C1-C4)-alkyl, heterocyclyl-
sulfonyl-(C1-C4)-aIkyl, heterocyclylamino-(C1-C4)-alkyl, heterocyclyl-
sulfonyloxy-(C1-C4)-aIkyI, heterocycIyIsulfonylamino-(C1-C4)-alkyl,
heterocyclylcarbonyl-(C1 -C4)-alkyl, heterocyclylcarbonyloxy-(C1 -C4)-
alkyl, heterocycIyIoxycarbonyl-(C1-C4)-alkyl, heterocyclylcarbonyl-
amino-(C1 -C4)-alkyl, heterocyclylaminocarbonyl-(C1 -C4)-alkyl, halo-
(C1 -C4)-alkyIthio-(C1 -C4)-alkyl, haIo-(C1 -C4)-aIkylsulfinyl-(C1 -C4)-
alkyl, halo-(C1 -C4)-alkyIsulfonyl-(C1 -C4)-aIkyI, halo-(C1 -C4)-alkyl-
amino-(C1-C4)-afkyl, halo-(C1-C4)-alkylsuIfonyloxy-(C1-C4)-alkyl,
haIo-(C1-C4)-alkylsulfonylamino-(C1-C4)-alkyl, halo-(C1-C4)-alkyl-
carbonyl-{C1 -C4)-alkyl, halo-(C1 -C4)-alkylcarbonyloxy-{C1 -C4)-alkyl,
halo-(C1 -C4)-alkyloxycarbonyI-(C1 -C4)-alkyl, halo-(C1 -C4)-alkyl-
carbonylamino-(C1-C4)-alkyi, halo-(C1-C4)-alkylaminocarbonyi-
(C1 -C4)-alkyl, aryl-(C1 -C4)-alkylthio-(C1 -C4)-alkyl, aryl-(C1 -C4)-
a(kylsulfinyl-(C1 -C4)-alkyl, aryl-(C1 -C4)-alkylsulfonyl-(C1 -C4)-alkyl,
aryl-(C1-C4)-alkylamino-(C1-C4)-alkyl, aryi-(C1-C4)-alkylsuifonyloxy-
(C1 -C4}-alkyl, aryl-(C1 -C4)-alkylsLilf onytamino-(C1 -C4)-alkyl, aryl-
(C1-C4)-alkyIcarbonyl-(CrC4)-alkyl, aryl-(C1-C4)-aIkylcarbonyloxy-
(CrC4)-aIkyl, aryl-(C1-C4)-alkyloxycarbonyl-(C1-C4)-alkyl, aryl-
{C1-C4)-alkylcarbonylamino-(C1-C4)-alkyl, aryl-(C1-C4)-alkylamino-
carbonyl-(C1-C4)-alkyl, heteroaryl-(C1-C4)-aIkylthio-{C1-C4)-alkyl,
heteroaryl-(C1 -C4)-aIkylsulfinyl-(C1 -C4}-aIkyl, heteroaryl-(C1 -C4)-
alkylsulfonyl-(C1-C4)-alkyl, heteroaryl-(C1-C4)-alkylamino-{C1-C4)-
alkyl, heteroaryl-(C1-C4)-alkylsulfonyloxy-(C1-C4)-alkyl, heteroaryl-
(C1 -C4)-alkyIsulfonylamino-(C1 -C4)-alkyl, heteroaryl-(C1 -C4)-
aIkylcarbonyl-(C1-C4)-alkyl, heteroatyl-(C1-C4)-alkylcarbonyloxy-
(C1-C4)-aIkyl, heteroaryl-(C1-C4)-aIkoxycarbonyl-(C1-C4)-alkyI,
heteroaryI-(C1-C4)-alkylcarbonylamino-(C1-C4)-alkyl, heteroaryl-{C1-
C4)-alkylaminocarbonyl-{C1 -C4)-alkyI, heterocyclyl-(C1 -C4)-alkylthio-
(C1-C4)-alkyl, heterocyclyI-(C1-C4)-a)kylsulfmyl-{C1-C4)-alkyl,
hGterocyclyl-(C1-C4)-alkylsulfonyl-{C1-C4)-alkyl, heterocyc)yl-(C1-C4)-alkytamino-{C1-C4)-alkyl, heterocyclyl-(C1-C4)-alkyisuHonyloxy-(C1 -C4)-alkyl, heterocyclyl-(C1 -C4)-alkyisulfonylamino-(C1 -C4)-alky(, heterocyclyl-(C1-C4)-alkylcarbonyKC1-C4)-aikyl, heterocyclyl-(C1-C4)-alkylcarbonyIoxy-(C1-C4)-alkyl, heteroGyclyl-(C1-C4)-alkoxy-


E together with the two carbon atoms to which it Is attached is a phenyl
ring or a 5- or 6-memberecl heterocycle which may be saturated,
partially saturated, fully unsaturated or aromatic and contains 1, 2 or
3 heteroatoms from the group consisting of oxygen, sulfur and
nitrogen, where the heterocycle contains not more than 2 sulfur or 2
oxygen atoms and the phenyl ring or heterocycle which contains the
group E is unsubstituted or mono- or polysubstituted by (C1-C6)-
alkyl, haIo-{C1-C6)-alkyl. (C1-C6)-aIkoxy, haio-(C1-C6)-alkoxy, (C1-
C6)-alkylthio, halo-(C1-C6)-alkylthio, (C1-C6)-alkylsurtinyl, halo-(C1-
C6)-alkylsulfinyl, (C1-C6)-alkylsuIfonyl, halo-(C1-C6)-alkylsuIfonyi,
aminosulfonyl, (C1-C6)-alkylaminosulfonyl, (C2-C12)-
2fi 27
dialkyiaminosulfonyl, NR R , (C2-C6)-alkoxyaIkyl, (C2-C6)-alkoxycarbonyl, (C2-C6)-alkylcarbonyl, halogen, cyano, nitro or pyridyi;
R is halogen, cyano, nitro, {Y)n-S(0)q-R, {Y)n-CO-R or is (C1-C6)-alkyl, (C2-C6)-alkenyl, {C2-C6)-alkynyl or (C1-C4)-aIkoxy which are substituted by v halogen atoms or k (C1-C4)-alkoxy groups;
R , R , R and R independently of one another are hydrogen or (C1-C6)-alkyl;

4
R is hydrogen, or is {C-i-C6)-alkyl, (C3-C6)'Cycloa!kyl, tetrahydropyran-3-yl, tetrahydropyran-4-yl or tetrahydrothiopyran-3-yI which are optionally substituted by one or more radicals from the group consisting of halogen, (C1-C6J-alkylthio and (CrCeJ-alkoxy;
R is hydrogen, (C1-C6)-alkyl or CO2R , or
4 6
R and R together form a bond or a three- to six-membered
carbocyclic ring;
R is hydrogen, (C1-C6)-aIkyl, halo-(C1-C6)-alkyl, (Ca-C6J-cycloaikyl or halo-(C3-C6)-cycloa!kyt;
R is hydrogen, (C2-C6)-aIkoxycarbonyl, halo-(C2-C6)-
28
alkoxycarbonyl, S(0)qR , CO2H or cyano;
R is (C1-C4)-alkyl, halo-(C1-C4)-alkyl or NRR';

R andR independently of one another are (CTC6)-alkyI, (C2-C6)-alkenyl, (C2-C6)-alkynyi, haio-(C1-C6)'a(kyl, aryl or aryl-(C1-C6)-alkyI which are optionally substituted by one or more radicals from the group consisting of halogen, cyano, nitro, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy and halo-(C1-C6}-alkoxy;
R and R independently of one another are hydrogen or R , or R and R together form a (C2-C5)-a!ketiyl chain;
20
R is (C1-C4)-alkyl, (C2-C8)-alkenyl, (C2-C6)-alkynyl, halo-(C1-C6)-alkyl, halo-(C2-C6)-alkenyl, halo-(C2-C6)-alkynyl, {C1-C6J-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, halo-(C1-C6)-alkoxy, halo-(C2-C6)-alkynyloxy or halo-(C2-C6)-alkenyIoxy;
R is hydrogen, (C1-C4}-alkyl, halo-{C1-C4)-alkyl, l}, 0-z\ S-Z or NR'ZR is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl or (C2-C4)-alkyny!, or
R , R together with the carbon atom to which they are attached form a carbonyl group or an O-CH2CH2-O group which is optionally substituted by one or two (C1-C3)-alkyl radicals, or R is hydrogen
22 1
and R is Z ;
R and R'* independently of one another are (C1-C6)-alkyl, halo-(C1-Cs)-alkyl, (C3-C5)-cycloalkyl, (Ca-C6l-alkenyl. halo-(C2-C6)-alkenyl, (C2-C6}-alkynyl, haIo-(C2-C6)-alkynyl or Z ;
R isZ
R is hydrogen or (CrC6)-alkyl;
R is hydrogen, (C1-C6)-aIkyl or (C1-C6)-alkoxy, or
RandR together form (CH2)2, {CH2)3, (CH2)4, (CH2)5, or (CH2)20(CH2)2;

28
R is (C1-C4)-alkyI, halo-(C1-C4)-alkyl or NR26 V27
30
R is (C1-C6)-alkyl or (C1-C6)-aIkoxy;
b is 1 or 2;
k is 0,1, 2 or 3;
I is 0,1 or 2;
m isOorl;
n isOorl;
p is 1,2 or 3;
V isO, 1, 2, 3, 4 or 5;
q isO, 1or2;
w IsO, 1,2 or 3,
and
B) at least one compound (Component B) from one of the groups
B-a) herbicides which are selectively active in cereals against
monocotyledonous and/or dicotyledonous harmful plants,
B -b) herbicides which are selectively active in corn against
monocotyledonous and/or dicotyledonous harmful plants,
B-c) herbicides which are selectively active in rice against
monocotyledonous and/or dicotyledonous harmful plants.

B-d) herbicides which are nonselectively active in land which is not under cultivation and/or selectively active in transgenic crops against monocotyledonous and/or dicotyledonous harmful plants,
where these compositions comprise the compounds of the formula (I) or their salts (Component A) and the compounds of groups B-a) to B-d) (Component B) in a ratio by weight of from 1:2000 to 2000:1.
In formula (I) and in ail subsequent formulae, carbon-containing radical chains such as alkyl, alkoxy, haloaikyi, haloalkoxy, alkylamino and aikylthio and the corresponding radicals which are unsaturated and/or substituted in the carbon skeleton, such as aikenyl and alkynyl, can in each case be straight-chain or branched. Unless specifically indicated othenvise, the lower carbon skeletons, for example having 1 to 6 C atoms or, in the case of unsaturated groups, having 2 to 4 C atoms, are preferred for these radicals. Alkyl radicals, also in the composed meanings, such as alkoxy, haloaikyi, etc., are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethyIbutyI, heptyls, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; aikenyl and aikynyl radicals have the meaning of the possible unsaturated radicals which correspond to the alkyl radicals; aikenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl; aikynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl. The multiple bond can be in any position of the unsaturated radical.
Unless indicated otherwise, cycloalkyi is a carbocyclic saturated ring system having three to nine C atoms, for example cyclopropyl, cyclopentyl or cyclohexyl. Analogously, cycloalkenyl is a monocyclic aikenyl group having three to nine carbon ring members, for example cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where the double bond can be in any position.
In the case of a disubstituted amino group, such as dialkylamino, these two substituents can be identical or different.
Halogen is fluorine, chlorine, bromine or iodine. Haloaikyi, -aikenyl and -aikynyl is alkyl, aikenyl and aikynyl, respectively, which is partially or fully substituted by halogen- preferably by fluorine, chlorine and/or bromine, in

particular by fluorine or chlorine, for example CF3, CHF2, CH2F, CF3CF2, CH2FCHCI, CCI3, CHCI2. CH2CH2CI; haloalkoxy is, for example, OCF3. OCHF2, OCH2F, CF3CF2O, OCH2CF3 and OCH2CH2CI; this applies correspondingly to haloalkenyl and other halogen-substituted radicals.
The term "heterocyclyl" is to be understood as meaning the radicals of three- to nine-membered saturated, partially or fully unsaturated heterocycles which contain one to three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur. If chemically possible, these radicals can be attached at any position of the heterocycle. Heterocycly! is preferably axiridinyl, oxiranyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothienyl, pyrrolidinyl, isoxazolidinyl, isoxazolinyi, thiazolinyl, thiazolidinyl, pyrazolidinyl, morpholinyl, piperidinyl, dioxolanyl, dioxanyl, piperazinyl, oxepanyl, azepanyl.
Heteroaryl is the radical of a heteroaromatlc compound which, in addition to carbon ring members, contains one to five heteroatoms from the group consisting of nitrogen, oxygen and sulfur. Heteroaryl is preferably furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothlazolyl, 1,2,3-tria2olyl, 1,2,4-triazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadia20lyl, 1,3,4-oxadia2olyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadia2olyl, 1,3,4-thiadiazolyI, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazlnyl, 1,2,4-triazinyl, 1,3,5-triazinyl.
Aryl is an aromatic mono- or polycyclic hydrocarbon radical, for example phenyl, naphthyl, biphenyl and phenanthryl.
The term "partially or fully halogenated" is meant to express that some or all of the hydrogen atoms In the groups characterized In this manner can be replaced by identical or different halogen atoms as mentioned above.
If a group or a radical is polysubstiluted, this is to be understood as meaning that when the different substituents are combined, the general principles of the construction of chemical compounds have to be followed, i.e. that no compounds are formed which are known to the person skilled in the art to be chemically unstable or not possible. This also applies accordingly to the attachment of individual radicals.

Depending on the steric and/or electronic conditions, an oxo group may also be present in the tautomeric enol form.
(f a group or a radical is polysubstituted by other radicals, these other radicals can be identical or different.
If a group or a radical is mono- or polysubstituted without the number and the type of substituents being given in detail, this is to be understood as meaning that this group or this radical is substituted by one or more identical or different radicals selected from the group consisting of halogen, hydroxyl, cyano, nitro, formyl, carboxyl, amino, Ihio, (C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkyl, halo-(C1-C6)-alkoxy, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C2-C6)-alkenyloxy, (C2-C6)-a)kyny)oxy, (C3-C6)-cycioaIkyI, {C3-C6)-cyc!oalkoxy, (C1-C6)-alkyIthio, haio-{C1-C6)-alkylthio.
Depending on the type and the attachment of the substituents, the compounds of the formula I can be present as stereoisomers. If, for example, one or more alkenyl groups are present, diastereomers may exist. If, for example, one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers may exist. From the mixtures produced in the preparation, stereoisomers can be obtained by customary separation methods, for example by chromatographic separation procedures. Stereoisomers can also be prepared selectively by using stereoselective reactions and employing optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers and mixtures thereof which are embraced by the fomiula I but not defined specifically.
Of more interest are herbicidal compositions w/hich comprise as Component A) a compound of the formula (I) in which Q is one of the radicals Q, Q , Q or Q'.
Of particular interest are herbicidal compositions which comprise as Component A) a compound 0I the formula (I) in which Q is one of the radicals Q, Q or Q, preferably Q or Q.
Of particular interest are likewise herbicidal compositions which comprise as Component A) a compound of the formula (1), in which X is a radical X .

From the group B-a), the herbicides amidosuHuron, benlazone, bromoxynil, carfentrazone-ethyl, chlortoluron, clodinafop, cloransuiam-methyl, didofop-methyl, fenoxaprop-P-ethyl, florasulam, flufenacet, fluoroglycofen-ethyl, flupyrsulfuron-methyl-sodium, iodosulfuron. isoproturon, metsulfuron, pendimethalin, pyraflufen-ethyi, sulfosulfuron, thifensulfuron, tralkoxydim, tribenuron, the herbicide 2-amino-4-(1-fluoro-1-methylethyl)-6-(3-phenyl-1-cycIobutyl-1-propylamino)-1,3,5-tria2ine known from WO 97/08156 and the herbicide N-[(4,6-dimethoxy-pyrimldin-2-yl)-aminocarbonyl]-2-methoxy-carbonyl-5-methylsulfonylaminomethylbenzenesulfonamid known from WO 95/10507 are particularly suitable for controlling monocotyledonous and/or dicotyledonous harmful plants in cereals.
Very particularly suitable are bromoxynil, clodinafop, fenoxaprop-P-ethyl, iodosulfuron, pyratlufen-ethyl, tralkoxydim, 2-amino-4-{1 -fluoro-1 -methylethyl)-6-(3-phenyl-1 -cyciobutyl-1 -propylamino)-1,3,5-lha2ine and sulfonyl ureas of the formula (11).
From the group B-b), the herbicides acetochlor, alachlor, atrazine, bromoxynil, carfentrazone-ethyl, dicamba, diflufenzopyr, dimethenamid, flufenacet, flumetsulam, fluthiacet-methyl, halosulfuron, imazamox, imazapyr, imazaquin, imazethapyr, iodosulfuron, metolachlor, metosulam, metribuzin, nicosulfuron, pethoxamid, pendimethalin, primisulfuron, prosulfuron, pyridate, rimsulfuron, thenylchlor, thifensulfuron-methyl, tritosulfuron and N-[(4,6-dim8thoxypyrimidin-2-yl)-aminocarbonyl]-2-dimethyIaminocarbonyl-5-formylben2enesulfonamide are particularly suitable for controlling monocotyledonous and/or dicotyledonous harmful plants in corn.
Very particularly suitable are bromoxynil, dicamba, diflufenzopyr, iodosulfuron, nicosulfuron, rimsulfuron and N-[(4,6-dimethoxypyrimidin-2-y!)-aminocarbonyll-2-dimethylamlnocarbonyl-5-formylbenzenesulfon-
amide.
From the group B-c) the herbicides anilofos, azimsulfuron, benfuresate, bensulfuron, bentazone, benthiocarb, bromobutide, bispyribac-sodium, butachlor, cinosulfuron, clomazone, cyclosulfamuron, ethoxysulfuron, esprocarb, imazosulfuron, KPP-314, pyribenzoxim, mefenacet, molinate, oxaziclomefone, OK9701, oxadiargyl, pretilachlor, propanil, pyrazosulfuron, quinciorac, thenylchlor, triclopyr and the herbicide 1-(3-chloro-4,5,6,7-tetrahydropyrazolo-t1,5-a]-pyrid-2-yl)-5-(methylpropargyIamino)-4-

pyrazolylcarbonitrile known from EP-A 0 863 705 are particularly suitable for controlling monocotyledonous and/or dicotyledonous harmful plants in rice.
Very particularly suitable are benfuresate, bensulfuron, ethoxysulfuron, molinate, oxaziclomefone and 1-(3-chloro-4,5,6,7-tetrahydropyra2oIo-[1,5-al-pyrid-2-yl)-5-(methylprQpargylamino)-4-pyrazolylcarbonitrile.
From the group B-d), the herbicides glufosinate, glyphosale, imazamox, imazapyr, imazaquin, imazethapyr and sujfosate are particularly suitable for controlling monocotyledonous and/or dicotyledonous harmful plants on land which is not under cultivation and/or selectively in transgenic crops. Very particularly suitable are glufosinate and glyphosate.
The active compounds mentioned above by their common names are known, for example, from "The Pesticide Manual", 11th edition, 1997, British Crop Protection Council, and/or are shown in the table brelow.



In the combinations according to the invention, application rates in the range from 1 to 2000 g, preferably from 10 to 500 g, of active ingredient per hectare (ai/ha) of the Component A) and from 1 to 2000 g, preferably from 1 to 500 g of the Component B) are generally required.
The weight ratios of the Components A) to B) to be used can be varied within wide ranges. The ratio is preferably in the range from 1:50 to 500:1, in particular in the range from 1:20 to 50'.1. Optimum weight ratios may depend on the particular field of application, on the weed spectrum and the active compound combination used and can be determined in preliminary experiments.
The compositions according to the invention can be employed for the selective control of annual and perennial monocotyledonous and dicotyledonous harmful plants in crops of cereals (for example barley, oats, rye, wheat), corn and rice and in crops of transgenic useful plants or crops of useful plants selected by classical means which are resistant to active compounds A) and B). Likewise, they can be employed for controlling undesirable harmful plants in plantation crops such as oil palm, coconut palm, Indian-rubber tree, citrus, pineapples, cotton, coffee, coca and the like, and also in fruit production and viticulture.

The compositions according to the Invention act against a broad spectrum of weeds. They are suitable, for example, for controlling annual and perennial harmful plants such as, for example, from the species abutilon, alopecurus, avena, chenopodium, cynoden, cyperus, digitaria, echinochloa, elymus, galium, Ipomoea, lamium, matricaria, scirpus, setaria, sorghum, veronica, viola and xanthium.
The herbicidal compositions according to the invention are also distinguished by the fact that the effective dosages of the Components A) and B) used in the combinations are reduced with respect to an individual dosage, so that it is possible to reduce the required active compound application rates.
The invention also provides a method for controlling undesirable vegetation, which method comprises applying one or more herbicides A) together with one or more herbicides B) to the harmful plants, parts thereof or to the area under cultivation.
When herbicides of Type A) and B) are applied jointly, superadditive (= synergistic) effects are observed. The activity in the combinations is more pronounced than the expected sum of the activities of the individual herbicides employed and the activity of the particular individual herbicide A) and B). The synergistic effects permit the application rate to be reduced, a broader spectrum of broad-leaved weeds and weed grasses to be controlled, more rapid onset of the herbicidal action, a more prolonged action, better control of the harmful plants by only one application, or few applications, and widening of the period of time within which the product can be used. These properties are required in weed control practice to keep agricultural crops free from undesirable competing plants and thus to ensure and/or to increase quality and quantity of the yields. These novel combinations markedly surpass the prior art with respect to the described properties.
The active compound combinations according to the invention can either be present as mixed formulations of the Components A) and B), if appropriate together with other customary formulation auxiliaries, which mixed formulations are then applied in the usual manner in the form of a dilution with water, or else they can be prepared in the form of so-called

tank mixes by joint dilution with water of the components which are formulated separately, or partly separately.
The Components A) and B) can be formulated in various ways, depending on the prevailing biological and/or physicochemical parameters. Suitable general possibilities for formulations are, for exampte: wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions (EW) such as oil-in-water and water-in-oll emulsions, sprayabie solutions or emulsions, oil- or water-based dispersions, suspoemulsions, dusts (DP), seed dressing products, granules for soil application or for broadcasting or water-dispersible granules (WG), ULV formulations, microcapsules or waxes.
The individual types of formulation are known in principle and are described, for example, in: Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Vol. 7, C. Hauser Verlag Munich, 4th Ed. 1986; van Valkenburg, "Pesticides Formulations", Marcel Dekker N.Y., 1973; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd, London. The formulation auxiliaries required, such as inert materials, surfactants, solvents and other additives, are also known and are described, for example, in: Watkins, "Handbook o1 Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y.; Marsden, "Solvents Guide", 2nd Ed., Interscienoe, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem, Publ, Co. Inc., N.Y, 1964; Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Vol. 7, C. Hauser Verlag Munich, 4th Ed. 1986.
Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances, such as other herbicides, fungicides or insecticides, and also safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or tank mix.

Wettable powders are preparations which are uniformly dispersible in water and which, besides the active compound, also comprise ionic or nonionic surfactants (wetting agents, dispersants), for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesuifonates or alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene-sulfonate or else sodium oleoylmethyltaunnate, in addition to a diluent or an inert substance.
Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons, with the addition of one or more ionic or nonionic surfactants (emulsifiers). Examples of emulsifiers which can be used are: calcium alkyiarylsulfonates, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan fatty acid esters, potyoxyethylene sorbltan fatty acid esters or polyoxyethylene sorbitol esters.
Dusts are obtained by grinding the active compound with finely divided solid materials, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Granules can be prepared either by spraying the active compound onto absorptive, granulated inert material, or by applying active compound concentrates to the surface of carriers, such as sand, kaolinite or granulated inert material, with the aid of binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active compounds can also be granulated in the manner customary for the preparation of fertilizer granules, if desired as a mixture with fertilizers. Water-dispersible granules are, In general, prepared by processes such as

spray-drying, fluidized-bed granulation, disk granulation, mixing using high¬speed mixers, and extrusion without solid inert material.
The agrochemical preparations generally comprise from 0.1 to 99 percent
by weight, in particular from 0.2 to 95% by weight, of active compounds of
ypes A) and B), the following concentrations being customary, depending
)n the type of formulation: In wettable powders, the active compound
:oncentration is, for example, approximately 10 to 95% by weight, the
emainder to 100% by weight being composed of customary formulation
components. In the case of emulsifiable concentrates, the active compound
concentration can be, for example, from 5 to 80% by weight. Formulations
in the form of dusts in most cases comprise from 5 to 20% by weight of
active compound, sprayable solutions approximately 0.2 to 25% by weight
of active compound. In the case of granules, such as disperslble granules,
the active compound content depends partly on whether the active
compound is in liquid or solid form and on which granulation auxiliaries and
fillers are used. In general, the content in the water-dispersible granules
amounts to between 10 and 90% by weight. In addition, the active
compound formulations mentioned comprise, if appropriate, the tackifiers,
wetting agents, dispersants, emulsiflers, preservatives, antifreeze agents,
solvents, fillers, colorants, carriers, antifoams, evaporation inhibitors and
pH or viscosity regulators which are customary in each case.
For use, the formulations, which are in commercially available form, are, if appropriate, diluted in a customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusts, soil granules, granules for spreading and sprayable solutions, are conventionally not diluted any further with other inert substances prior to use.
The active compounds can be applied to the plants, parts of the plants, seeds of the plants or the area under cultivation (tilled soil), preferably to the green plants and parts of the plants and, if desired, additionally to the tilled soil.

A possible use is the joint application of the active compounds in the form of tank mixes, where the concentrated formulations of the individual active substances, in the form of their optimal formulations, are mixed jointly with water in the tank, and the spray mixture obtained is applied.
A joint herbicidal formulation of the combination according to the invention of the components A) and B) has the advantage that it can be applied more easily because the amounts of the components have already been adjusted with respect to one another to the correct ratio. Moreover, the auxiliaries of the formulation can be selected to suit each other in the best possible way, while a tank mix of various formulations may result in undesirable combinations of auxiliaries.
A. Formulation examples
a) A dust (WP) is obtained by mixing 10 parts by weight of an active compound/active compound mixture and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill.
b) A wettable powder (WG) which is readily dispersible in water is obtained by mixing 25 parts by weight of an active compound/active compound mixture, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurlnate as wetting agent and dispersant, and grinding the mixture In a pinned-disk mill.
c) A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of an active compound/active compound mixture with 6 parts by weight of alkylphenol polyglycol ether {Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example approximately 255 to 277°C) and grinding the mixture in a ball mill to a fineness o1 below 5 microns.

d) An emulsifiable concentrate (EC) is obtained from 15 parts by weight of an active compound/active compound mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
e) Water-dlspersible granules are obtained by mixing
75 parts by weight of an active compound/active compound mixture, 10 parts by weight of calcium lignosulfonate,
5 parts by weight of sodium lauryl sulfate,
3 parts by weight of polyvinyl alcohol and
7 parts by weight of kaolin
grinding the mixture in a pinned-disk mill and granulating the powder
in a fluidized bed by spraying on water as granulation liquid.
f) Water-dispersible granules are also obtained by homogenizing and
precomminuting, in a colloid mill,
25 parts by weight of an active compound/active compound mixture, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-
disulfonate,
2 parts by weight of sodium oleoyimethyltaurinate,
1 part by weight of polyvinyl alcohol,
17 parts by weight of calcium carbonate and
50 parts by weight of water,
subsequently grinding the mixture in a bead mill and atomizing and drying the resulting suspension In a spray tower by means of a single-substance nozzle.
B. Biological Examples
Outdoors, crop plants were grown on plots of a size of from 5 to 10 m on various soils and under various climatic conditions, and the natural presence of harmful plants and/or their seeds In the soil was utilized for the experiments. The treatment with the compositions according to the invention or the herbicides A) and B) applied individually was carried out after emergence of the harmful and the crop plants, in general at the 2- to

4-leaf stage. The active compounds or active compound combinations, formulated as WG, WP or EC, was carried out by the post-emergence method. After 2 to 8 weeks, visual evaluation was carried out in comparison with an untreated comparative group. It was found that the compositions according to the invention have synergistic herbicidai action against economically important mono- and dicotyledonous harmful plants, i.e. that most of the compositions according to the invention have higher, some considerably higher, herbicidai activity than the sum of the activities of the individual herbicides. In addition, the herbicidai activities of the compositions according to the invention exceed the expected values according to Colby. In contrast, the treatment caused insignificant, if any, damage to the crop plants.
If the obsen/ed activity values of the mixtures already exceed the formal sum of the values for the trials with individual applications, they also exceed the expected value according to Colby which is calculated using the following formula (of. S. R. Colby; in Weeds 15 (1967) pp. 20 to 22):














Claims:
1. A herbicidal composition, comprising an effective amount cf A) at least one compound of formula (1) and its agriculturally customary salts (Component A)

2 is a live- to ten-membered monocyclic or cicyclic saturated, partially saturated, fully unsaturated or aromatic ring which is


attached via carbon or nitrogen and which, in addition to carbon atoms, contains 1, 2, 3 or 4 heteroatoms from the group consisting of oxygen, sulfur and nitrogen and which is unsubstituted or mono- or polysubstituted by halogen, cyano. nitro, cyano-(CTC4)'alkyl, CO-R"', (C1-C4)-alkyI, halo-(C1-C4)-alkyl, {C3-C8)-cycloalkyl, (C1-C4)-alkoxy, halo-(C1-C4)-aikoxy. (C1-C4)-alkyIthio, haJo-(C1-C4)-a!kyIthio, di-(C1-C4)-aIkylamino, "by phenyl which is unsubstituted or mono- or polysubstituted by halogen, cyano, nitro, (CTC4)-alkyI or ha!o-(C1-C4)-alkyl or by an oxo group;
is {C3-Ci2)-cycloaIkyloxy-(C1-C4)-alkyi, ary!oxy-{C1-C4)-alkyI,
heteroaryIoxy-(C-i-C4)-aikyl, heterocyc[yl-(C1-C4)-alkyl, ha!o-
(C1-C4Valkoxy-(C-i-C4)-alky!, aryl-{C1-C4)-alkoxy-(C1-C4)-aikyl,
heteroaryl-(C1-C4)-aikoxy-(C1-C4)-alJ alkoxy-(C1-C4)-alkyi, aryi-(C3-C8)'Cycioaikylthio-{C1-C4}-a!kyl,
heteroary]-{C3-C8)-cycIoaikylthio-{C1-C4}-alkyi, helerocyciyl-
(C3-C8)-cycloaikylthio-(C1-C4)-alkyI, {C3-C8)-cycloaIkylsu!finy!-
(C1-C4)-alky!, (C3-C3)-cyc!oalkyIsuIfonyl-(CvC4)-a!kyl, (Cs-Cs)-
cycloaIkyiamino-(C1-C4)-alkyi, (C3-C8)-cycIoaiky)sulfonyloxy-
(C1-C4)-alkyl, (C3-C8)-cycloa!kylsuIfonyIamino-(C1-C4)-alkyi,
(C3-Ca)-cyc[oaIkylcarbonyi-{C1-C4)-alkyi, {Cs-Cs}-
cycloalkylcarbonyloxy-(C-i-C4)-alkyl, (Cs-Cs)-
cycloalkoxycarbonyl-(C1-C4)-alkyl, (Cs-Cg)-
cycloalkylcarbonylamino-(CrC4)-al*y5i (Cs-Cg)-
cycloalkylaminocarbonyl-(C1-C4)-alkyl, (C4-Ci2)-cyc!oa)kyl-(C1-
C4)-aikyl, (C4-Ci2}-cycioaIkyIthio-(CrC4Va'kyI, (C4-C12)-
cycloalkyIsuIfinyl-{C1-C4)-alkyI, {C4-Ci2)-cycloa!kyisu!fonyl-(C1-
C4)-alkyl, (C4-Ci2)-cycloalkylamino-(C-!-C4)-alky!, (C4-C12;-
cycioaiKy!su!ionyloxy-(C1-C4)-5lkyI, (C4-Ci2)-cyc!oaikylsulfonyi-
amfno-(C-i-C4)-alky], {C4-Ci2)-cycioGlkylccrbonyi-(C1-C4)-alkyl,
(C4-Ci2)-cycioaJky!carbony!oxy-(CrC4)-£lf alkoxycarbonyi-{C1-C4)-a!kyL {C4-Ci2)-cyc!os!kyi-
carbony!amino-(C-,-C4)-a!.kyl, (C-Cral'V-'-'sikviarninocarbonyl-
(C1-C4}-aikyi, sry!thio-{CvC4)-alky!, Grylsu!finvl-(C-;-C4)-alkyi,
arytsulfonyl-{C1-C4)-aiky;, sryl3mino-(C1-C4)-a)kyi,
ary]sulfonyloxy-(C-;-CrO-alAyi, arylsL,'lfonylamino-(C1-C4)-a!ky),


arylcarbonyl-{C1-C4)-alky!, aryIcarbonyloxy-{C1-C4>alky!,
aryioxycarbonyl-{C1-C4)-alky), arylcarbonyiafnino-(C]-C4)-aikyl,
aryiaminocarbonyI-(CTC4)-alky), heteroaryllhio-(C1-C4)-afkyl.
heteroarylsulfinyl-(C1-C4)-aiky), heteroarylsulfonyl(C1-C4)-alkyl,
heteroarylamino-(C1-C4)-allkyl, heteroarylsuifonyloxy-(CrC4)-
alkyl. hGteroaryisulfonylamino-(C1-C4)-alkyl,
heteroary!carbonyi-(C1-C4)-alky!, heteroarylcarbonyioxy-(C1-
C4)-a!kyl, heteroary!oxvcarbDnyl-(CTC4)-aikyS,
heteroarylcarbonylai-nino-(C1-C4)-a!ky!, heteroaryl-
amInocarbonyl-(Ci'C4)-a!! helerocyc)yIsu!finyl-(C1-C4)-aIkyl, heterocyclylsulfony!-(CvC4)-
alkyl, heterocyclyIamino-(C1-C4)-a[kyl, heterocyclylsulfonyloxy-
(C1-C4)-alkyl, heterocyclylsu)fonylamino-(C1-C4)-alkyi,
heterocyc!y[carbonyl-(C1-C4}-alkyI, heterocyclylcarbonyloxy-
(C1-C4)-alkyl, heterocyclyIoxycarbony!-(C1-C4)-alkyI,
heterocyclylcarbonylamino-(C1-C4)-aIkyl, heterocyciy)-
aminocarbonyI-(C1-C4)-aIkyl, halo-(C1-C4)-alkyithio-{C1-C4)-
alkyl, halo-(C1-C4)-alkyIsuinny]-{C,-C4)-a]kyl, halo-{CrC4)-
alkylsulfony!-(CrC4)-alkyl, halo-(C1-C4)-aIkylamino-(CrC4)-
aikyl, halo-{C1-C4)-alky)su)fonyloxy-(C1-C4)-aIkyi, halo-{CrC4)-
alkylsulfonylamino-(CTC4)-alky!, halo-(C1-C4)-a'kyicarbonyi-
(C1-C4}-alkyl, haIo-(C1-C4)-ri:kylc3rbonyloxy-(C1-C4)-a(kyl, haio-
{C1-C4)-alkyloxycarbonyl-(C-;-C4)-a!kyl, ha!o-{C1-C4)-aiky!-
carbonylamino-{C1-C4)-alkyl, ha[o-{C1-C4)-aikylaminocarbony!-
(Ci'C4)-alkyI, aryl-{C1-C4)-a!kyIthio-(CrC4}-aIky[, aryl-{C1-C4)-
aIkylsulfInyl-(C1-C4)-aIkyl, aryl-(CrC4)-aikyIsulfonyl-{C1-C4)-
aikyl, aryI-{C1-C4)-a!kyiam]no-(C1-C4)-a)kyl. ary}-{C1-C4)-
alkytsu!fonyloxy-(CTCj)-5ikyl, aryl-(C1-C4)-alkyisul!onylamino-
(C1-C4)'alkyl, aryi-{C1-C4)-aikylCErbonyl-(CvC4)-a!kyk aryi-iC1-
C4)-alkylcarbonyloxy-(CrC4)-alkv!, ary!-(C!-C4r
alky!oxycarbonyl-(CTC4)-sl'. aIky!carbonyIam!nc-(CvC4)-B!ky!, aryl-(C.-.-C4)-alky!amino-
carbony!-{CvC4)-aikyL helercary;-(0-Ca)-aIky;thio-(CrC4}-
alky!, heteroarv!-(C-!'C4)-a;; (CvC4)-alkylsulfony!M;CvC4i-a!ky!, hsteroary!-(C1-C4)-
aIkyIamino-(C1-C4}-a!y.y:, iiGi3rGr:ryi-(C|-C4)-£:!kylsL;ifonyloxy-
(C1-C4}-aIkyl, hetercary]-(CTC4)-a!kyl3Uifonylammo-(CrC4)-


alkyl, heteroaryl-(C1-C4)-aIkylcarbonyI-{C1-C4)-alkyI, heteroaryl-
(C1-C4)-aikylcarbonyfoxy-(C1-C4)-alkyI, heteroaryl-(C1-C4)-
aIkoxycarbonyl-(C1-C4)-alkyi, heteroaryi-{CvC4)-
a(kylcarbcnyIamino-(CTC4)-rJky!, heteroaryl-C1-C)-
alky[aminocarbonyl-(CTC4)-afkyl, heterocyciyl-(CvC4)-
aikyIthio-(C1-C4)-aIky), heterocyclyj-(CvC4)-alkyIsu!fmy[~{C-5-
C4}-alkyl, heterocyclyl-(CvC4)-alkylsuIfonyI-{C1-C4)-aIky[,
heterocyclyl-(C1-C4)-3lkyIamino-(C1-C4)-aIkyl, heterocyclyl-(C1-
C4)-aIkyisuIfony)oxy-(C1-C4)-alkv!, heterocyclyi-(C1-Cd)-
alkyisu!fonylamrno-(C1-C4)-5ikyl, heterocyciy!-{CvC4)-
aIkyIcarbonyI'(C-i-C4)-aIkyl, heterocycly!-(C1-C4)-
aIkylcarbonyIoxy-(C1-C4}-alkyl, hsterocyc!y!-(C1-C4)-a!koxy-
carbonyl-(C1-C4)-a!ky!, heterocycly!-(CvC4)-alkyicarbony!-
amino-(C1-C4)-a!kyl, heterocycIyU(CvC4)-alkylcarbonvlamino-(C1-C4)-alkyl, heterocyclyl-(CvC4)-clkylaminocarbony!'(C-i-C4)-

E together with the two carbon atoms to which it is attached is a phenyl ring or s 5- or 6-membered heteroycls which may bs salurated, partisliy saturated, fully ursaturated or aromatic and contains 1. 2 or 3 heteroatoms from the group consisting of oxygen, sulfur and nitrogen, where the hoterocycls contains not more than 2 sulfur or 2 oxygen atoms and the phenyl ring or


heterocycle which contains the group E is unsubstituted or
mono- or polysubstituted by (C1-C6)alkyl, haIo-(C1-C5)-aIkyl,
(C1-C6)-alkoxy, halo-{CTC6)-a!koxy, (C1-C6)-alkylth!o, halo-(C1-
C6)-alkylthio, (C1-C6)-alkylsulflnyl, halo-(CrC6)-alkyl3ulfinyl,
(C1-C6)-alkylsulfanyl, halo-(C1-C5)-alkylsulfonyl, aminosulfonyl,
(C1-C6)-aIkylaminosulfonyl, (C2-C12)-dialky!aminosulfonyi,
NRR', (C2-C6)-alkoxyalkyl, (C2-C6)-alkoxycarbonyl, (C2-C5)-alkylcarbonyl, halogen, cyano, nitro or; pyridyl
R is halogen, cyano, nitro, (Y)n-S(Q}q-R , (Y)n-CO-R or is (Cv C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-aikynyi or (C1-C4)-alkoxy which are substituted by v halogen atoms or k {C1-C4)-alkoxy groups;
2 3 5 7
R , R , R and R tndepcndently of one another are hydrogen or {C1-C6)-alkyI;
4 R is hydrogen, or is (C1-C6)alkyl, (C2-C6)cyclonlkyl,
tetrahydropyran-3-yl, tctrahydropyran-4-yI or
tetrahydrothiopyran-3-yl which are substituted by k radicals
from the group consisting of halogen, (C1-C6)-alkylthio and (C-]-
CeValkoxy,
R is hydrogen, (C1-C6)-alkyl or CO2R , or
4 6
R and R together form a bond or a three- to six-membered
carbocyclic ring;
R is hydrogen, (C1-CeJ-alkyl, hEiio-(C-|-C6)-alky!, (C3-C6}-cycloaIkyl
or halo-(C3-CB)-cycloa!kyl;
12
R is hydrogen, (C2-C5)-2!koxycarbcnyl, ha!o-(C2"C6)-
aikoxycarbony!, S(0)c , CO2H or cyano; R"" is (C-i-C4)-a!ky!, ha!o-(C-;-C/Vr,iky! cr !?,R';
R and R independently of one another ars (C-]-Cg)-alky!, (C2-C6)-alkenyl, (C2-Cs)-aIkyny!, ha!o-{CTC6)-a!kyl, aryl or aryl-(C1-C6)-
A:'.iENDED SHEET

alkyl which are substituted by k radicals from the group consisting of halogen, cyano, nitre, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy and halo-(C1-C6)-alkoxy;

R and R independentiy of one another are hydrogen or R , or
18 19
R and R together form a (C2-C5)-alkenyl chain;
20
R is (C1-C4)-alkyl, (C2-C8)-alkeny!, (C2-C6)-alkynyl, halo-{C1-C6)-
alkyl, halo-(C2-C5)-alkenyl, ha!o-(C2-C5)-alkynyl, (C1-C5)-a!koxy, (C2-C6)-aIkenyloxy, {C2-C6)-alkynvloxy, halo-(C1-C6)-alkoxy, halo-(C2-C6)-alkynyloxy or halo-(C2-C5)-aikenyloxy; R21 is hydrogen, (C1-C4)-alky[, halo-(CvC4)-a!kyl, z\ 0-z\ S-Z or

R is hydrogen, (C1-C4)-aIkyI, {C2-C4)-alkenyI or {C2-C4)-olkynyl, or
21 22
R , R together with the carbon atom to which they are attached
form a carbonyl group or an O-CH2CH2-O group which is
21 substituted by q (C1-C3)-alkyi radicals, or R is hydrogen and
„22 . _1 R isZ ;
23 24
R and R independently of one another are (C1-CeJ-aikyI, ha!o-(C1-
C6)-alkyI, (C3-C6)-cycloalky!, (C2-C5)-alkenyJ, ha!o-(C2-C6)-
alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl orZ ;
R isZ ;
R is hydrogen or (C-!-C6)-alky!:
27 R is hydrogen, (C1-C6>alkyi or (Ci"C5)-aIkoxy, cr
RandR' together form (CH2)2, (CH2)3, (CH2)4> (Crl2)5, or
{CH2)20(CH2)2;
R is (CrC4)-alkyl, halo-(C1-C4)-?.lkyi or NR'R*';
R is (CrC5}-alkyi or (C1-Cg)-alkcxy;


b is 1 or 2;
k is 0,1, 2 or 3;
I is 0,1 or 2;
m is 0 or 1;
n is 0 or 1;
p is 1,2 or 3; q is 0,1 or 2;
V is 0,1, 2, 3, 4 or 5;
w is 0,1, 2or3,
and
B) at least one compound (Component B) from one of the groups B-a) herbicides which are selectively active in cereals against
monocotyledonous and/or dicotyledonous harmful plants, B-b) herbicides which are selectively active in corn against
monocotyledonous and/or dicotyledonous harmful plants, B-c) herbicides which are selectively active in rice against
monocotyledonous and/or dicotyledonous harmful plants, B-d) herbicides which are nonseleclively active in land which is not
under cultivation and/or selectively active in transgenic crops
against monocotyledonous and/or dicotyledonous harmful
plants,
With the exception of combinations of compounds of the formula {!), in which
R1 is (C1-C5)-alkyl, (C2-C6)-alkanyl, (C2-C6)-alkynyl or (C1-C4)-a!koxy which are substituted by v halogen atoms or k (C1-C4)-alkoxy groups,


With the herbicides (Component B) acetochlor, alachlor, atrazlne, bentazone, bromoxynil, butachlor, dicamba, dimethenamid, imazethapyr, metoiachlor, metribuzin, nicosulfuron, pendimethalin, pyridate, rimsulfuron and thenylchlor,
and
where this composition comprises the compounds of the formula (I) or their salts (Component A) and the compounds of groups B-a) to B-d) {Component B) in a ratio by weight of from 1:2000 to 2000:1.
2. A herbicidal composition as claimed in claim 1, which comprises as Component A) a compound of the formula 1 in which X is a radical X .
3. A herbicidal composition as claimed in claim 1 or 2, which comprises as Component B) at least one herbicide from the group B-a), consisting of amidosulfuron, bentazone, bromoxynil, carfentrazone-ethyl, chlortoluron, clodinafop, cloransulam-melhyl, diclofop-methyl, fenoxaprop-P-ethyl, tlorasulam, fiufenacet, fluoroglycofen-ethyi, flupyrsulfuron-melhyl-sodium, iodosulfuron, isoproturon, metsulfuron, pendimethalin, pyraflufen-ethyl, sulfosuifuron, thifensulfuron, tralkoxydim, tribenuron, 2-amino-4-(1-fiuoro-1-methylethyl)-6-(3-phenyi-1-cyclobutyl'1-propylamino)-1,3,5-lrJazine and N-l(4,B-dimethoxypyrimidin-2-y))-aminocarbonyl]-2-methoxycarbonyl-5-methylsuIfonylaminomethylbenzenesulfonamide.
4. A herbicidal composition as claimed in claim 3, which comprises bromoxynil, clodinafop, fenoxsprop-P-ethyl, iodosulfuron, pyrailulen-ethyt, trall 5. A herbicidal composition as claimed in claim 1 or 2, which comprises as Component B) at least one herbicide from the group B-b), consisting of acetochlor, alachlor, atrazine, bromoxynil, carfentrazone-ethyl, dicamba, diflufenzopyr, dimethenamid,


flufenacet, flumetsulam, fluthiacet-methyl, haiosulfuron, imazamox, imazapyr, imazaquin, imazethapyr, iodosuifuron, metolachior, metosulam, metribuzin, nicosuifuron, pethoxamide, pendimethalin, primisulfuron, prosulfuron, pyridate, rimsulfuron, thenylchlor, thifensulfuron-methyi, tritosulfuron and N-[(4,6-dimethoxypyrimidin-2-yl)-arriinocarbonyl]-2-dimethylaminocarbonyl-5-formyibenzenesulfonamide.
6. A herbicidal composition as claimed in claim 5, which comprises bromoxynil, dicamba, diflufenzopyr, iodosuifuron, nicosuifuron, rimsulfuron or N-[(4,6-dimethoxypyrimidin-2-yI)-aminocarbonyI]-2-dimethy]aminocarfaonyJ-5-formylbenzenesulfonamide.
7. A herbicidal composition as claimed in claim 1 or 2, which comprises as Component B) at least one herbicide from the group B-c), consisting of anilofos, azimsulfuron, benfuresate, bensulfuron, bentazone, benthiocarb, bromobutide, bispyribac-sodium, butachlor, cinosulfuron, clomazone, cyciosulfamuron, ethoxysulfuron, esprocarb, imazosuifuron, KPP-314, pyribenzoxim, mefenacet, molinate, oxaziclomefone, OK9701, oxadiargyl, pretiiachlor, propanij, pyrazosulfuron, quinclorac, thenylchlor, Iriclopyr and 1-(3-chloro-4,5,6,7-tetrahydropyrazo[o-[1,5-a]-pyrid-2-yl)-5-(methyipropargylamino)-4-pyrazolylcarbonitriIe.
8. A herbicidal composition as claimed in claim 7, which comprises benfuresate, bensulfuron, ethoxysulfuron, molinate,
oxaziclomefone or 1-(3-chloro-4,5,6,7-tetrahydropyra20lo-[1,5-a]-pyrid-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile.
9. A herbicidal composition as claimed in claim 1 or 2, which comprises as Component B) at least one herbicide from the group B-d), consisting of glufosinate, glyphosate, imazamox, imazapyr, imazaquin, imazethapyr and sulfosate.
10. A herbicidal composition as claimed in claim 9, which comprises giufosinate or glyphosate.


11. A herbicidal composition as claimed in any of claims 1 to 10, wherein the ratio by weight A:B of the combined herbicides A) and B) is in the range from 1:20 to 50:1,
12. A herbictdal composition as claimed in any of claims 1 to 11, which comprises 0.1-99% by weight of herbicides A) and B) and 99 to 0.1% by weight of formulation auxiliaries which are customary in crop protection.
13. A method for controlling undesirable vegetation, which comprises applying one or more herbicides A) with one or more herbicides B) to the harmful plants, to parts thereof or to the area under cultivation, where the combination of the herbicides A) and B) is defined as in any of claims 1 to 12.
14. The use of a combination of herbicides A) and B) as herbicidal composition for controlling undesirable vegetation, where the combination of the herbicides A) and B) is defined as In any of claims 1 to 12.
AMENDED SHEET


15. A herbicidal composition substantially as hereinbefore described.
16. A method for controlling undesirable vegetation substantially as
hereinbefore described.


Documents:

in-pct-2002-0582-che abstract-duplicate.pdf

in-pct-2002-0582-che abstract.pdf

in-pct-2002-0582-che claims-duplicate.pdf

in-pct-2002-0582-che claims.pdf

in-pct-2002-0582-che correspondence-others.pdf

in-pct-2002-0582-che correspondence-po.pdf

in-pct-2002-0582-che description(complete)-duplicate.pdf

in-pct-2002-0582-che description(complete).pdf

in-pct-2002-0582-che form-1.pdf

in-pct-2002-0582-che form-13.pdf

in-pct-2002-0582-che form-26.pdf

in-pct-2002-0582-che form-3.pdf

in-pct-2002-0582-che form-5.pdf

in-pct-2002-0582-che form-6.pdf

in-pct-2002-0582-che petition.pdf


Patent Number 225828
Indian Patent Application Number IN/PCT/2002/582/CHE
PG Journal Number 02/2009
Publication Date 09-Jan-2009
Grant Date 01-Dec-2008
Date of Filing 19-Apr-2002
Name of Patentee BAYER CROPSCIENCE AG
Applicant Address ALFRED-NOBEL-STRASSE 50, 40789 MONHEIM
Inventors:
# Inventor's Name Inventor's Address
1 HACKER ERWIN MARGARETHENSTRASSE 16, 65239 HOCHHEIM,
2 BIERINGER, HERMANN EICHENWEG 26, 65817 EPPSTEIN
3 VAN ALMSICK, ANDREAS ROSSKOPFWEG 9, 61440 OBERURSEL,
4 WILLMS, LOTHAR KONIGSTEINER STRASSE 50, 65719 HOFHEIM,
PCT International Classification Number A01N 61/00
PCT International Application Number PCT/EP00/10369
PCT International Filing date 2000-10-20
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 DE 199 50 943.3 1999-10-22 Germany