CA2378857A1 - Combinations of herbicides and safeners - Google Patents

Combinations of herbicides and safeners Download PDF

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Publication number
CA2378857A1
CA2378857A1 CA002378857A CA2378857A CA2378857A1 CA 2378857 A1 CA2378857 A1 CA 2378857A1 CA 002378857 A CA002378857 A CA 002378857A CA 2378857 A CA2378857 A CA 2378857A CA 2378857 A1 CA2378857 A1 CA 2378857A1
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alkyl
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formula
substituted
radical
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Hermann Bieringer
Lothar Willms
Frank Ziemer
Erwin Hacker
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Bayer CropScience AG
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention relates to a herbicidally active agent that contains a mixture from A) a herbicidally active amount of one or more compounds of the formula (I), wherein X and Y are the same or different and represent hydrogen, halogen, for example fluorine.
chlorine, bromine or iodide, Z represents -S-CHR1-COOR2, wherein R1 represents hydrogen or C1-C20 alkyl, preferably C1-C6 alkyl, R2 represents C1-C20 alkyl. C3-C8 cycloalkyl or C1-C10-alkoxy-C1-C10-alkyl, preferably C1-C6 alkyl, C4-C6 cycloalkyl or C1-C4-alkoxy-C1-C4 alkyl, or -COOR3, wherein R3 represents C1-C20 alkyl, preferably C1-C6 alkyl. or Y and Z together represent a group -O-CHR4-CO-NR5- that forms a ring with the phenyl ring, wherein R4 represents hydrogen or C1-C20 alkyl, preferably C1-C6 alkyl, and R5 represents C1-C20 alkyl, C2-C20 alkenyl or C2-C20 alkinyl, preferably C1-C6 alkyl, C3-C5 alkenyl or C3-C5 alkinyl; and B) an antidotically effective amount of one or more safeners.

Description

' WO 01108488 PCT/EP00/07054 Combinations of herbicides and safeners Description The invention relates to the technical field of the crop protection products, in particular herbicide/antidote combinations (active substance/safener combinations) which are outstandingly suitable for the use against competing harmful plants in crops of useful plants.
EP-A-273 417 discloses herbicidally active substances which control a broad spectrum of weeds and which, alone or as a mixture with other active substances, can be employed for [lacuna] important weeds, mention being made both of what is called the nonselective use together with nonselective foliar-acting herbicides and of the possibility of selective uses in crops which have been made tolerant to such active substances by recombinant methods.
However, many of these active substances are not fully compatible with ~ (i.e. not sufficiently selective in) some important crop plants such as maize, rice or cereals, so that their use is strictly limited. In certain crops, they can therefore not be employed, or at such low application rates that the desired broad herbicidal efficacy towards harmful plants is not guaranteed.
Specifically, many of the abovementioned herbicides cannot be employed sufficiently selectively against harmful plants in maize, rice, cereals or some other crops.
To overcome these disadvantages, it is known to employ herbicidal active substances in combination with a so-called safener or antidote. A safener for the purpose of the invention is a compound or a mixture of compounds which compensates for, or reduces, the phytotoxic properties of a herbicide towards useful plants without substantially reducing the herbicidal action against harmful plants.
The identification of a safener for a particular class of herbicides remains a difficult task since the exact mechanisms by which a safener reduces the harmful effect of herbicides are unknown. The fact that a compound in combination with a particular herbicide acts as a safener allows no conclusions as to whether such a compound also acts as a safener with - ' 2 other classes of herbicide. Thus, it has emerged that, when using safeners for protecting the useful plants from herbicide damage, the safeners may still have a number of disadvantages in many cases. These are:
~ the safener reduces the action of the herbicides against the harmful plants, ~ the useful-plant-protecting properties are insufficient, ~ in combination with a given herbicide, the spectrum of the useful plants in which the safener/herbicide is to be used is insufficiently wide, ~ a given safener may not be combined with a sufficiently large number of herbicides.
It was an object of the present invention to identify herbicidal compositions in which the selectivity of the abovementioned herbicides with regard to important crop plants is increased. Surprisingly, this object is achieved by the herbicidal compositions of the present invention.
The invention therefore relates to a herbicidally active composition comprising a mixture of (A) a herbicidally active amount of one or more compounds of the formula (I) X
N
(l) ~N
I S Z
N
in which X and Y are identical or different and are hydrogen or halogen such as fluorine, chlorine, bromine or iodine, Z is -S-CHR~-COOR2 in which R~ is hydrogen or C1-C2p-alkyl, preferably C~-C6-alkyl, R2 is C~-C2p-alkyl, C3-Cg-cycloalkyl or C~-Cep-alkoxy-C~-C1p-alkyl, preferably C1-Cg-alkyl, C4-Cg-cycloalkyl or C~-C4-alkoxy-C1-C4-alkyl, or is -COORS where R3 is C~-C2p-alkyl, preferably C~-Cg-alkyl, or Y and Z together form a group -O-CHR4-CO-NR5- which, together with the phenyl ring, forms a ring in which R4 is hydrogen or C~-C2p-alkyl, preferably C~-Cg-alkyl, and R5 is C1-C2p-alkyl, C2-C2p-alkenyl or C2-C2p-alkynyl, preferably C1-C6-alkyl, Cg-C5-alkenyl or C3-C5-alkynyl, and (B) an antidote-effective amount of one or more safeners.
In formula (I), Z is preferably -S-CH(CH3)-COOR2 or -S-CH2-COOR2 where R2 is C~-C6-alkyl or C4-Cg-cycloalkyl.
The compound of the formula (I) is preferably described by the following formula (la) X
Y
(la) O
in which X is hydrogen or halogen, preferably fluorine, Y is halogen, preferably chlorine, and Z is as defined in formula (I) and is preferably -S-CH(CH3)-COOR2 or -S-CH2-COOR2 where R2 is C1-C6-alkyl or C4-Cg-cycloalkyl.
An especially preferred compound of the formula (i) is fluthiacet-methyl ((I-1 ), Pesticide Manual, 11 th Edition, British Crop Protection Council, pp 606-608, entry No. 359).
The safeners (B) are preferably selected from the group consisting of a) compounds of the formulae (II) to (IV), " 4 O ~ ~ (R,s) .
(Rt~~~, ~ n NJ
R'e O T/C~ ~R2o O
R~
R2~~ N
~ R~
(IV) where the symbols and indices having the following meanings:
n' is a natural number from 0 to 5, preferably 0 to 3;
T is a (C~ or C2)-alkanediyl chain which is unsubstituted or substituted by one or two (C1-C4)alkyl radicals or by [(C1-Cg)-alkoxy]carbonyl;
W is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the partially unsaturated or aromatic five-ringed heterocycles having 1 to 3 hetero ring atoms of the type N or O, the ring containing at least one nitrogen atom and not more than one oxygen atom, preferably a radical selected from the group consisting of (W1) to (V114), N . N . N -(CH2)~, ~N w ~N w ~N y N
2-, ~ ~s O-N
R~ R
COORS
(W1 ) (~) ( m' is 0 or 1;
R17, R~ 9 are identical or different halogen, (C~-C4)alkyl, (C~-C4)alkoxy, nitro or (C1-C4)haloalkyl;
R~8, R2~ are identical or different OR24, SR24 or NR24R25 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and up to 3 hetero atoms, preferably from -. . 5 the group consisting of O and S, which is linked to the carbonyl group in (II) or (III) via the nitrogen atom and which is unsubstituted or substituted by radicals selected from the group consisting of (C~-C4)alkyl, (C~-C4)alkoxy or optionally substituted phenyl, preferably a radical of the formula OR24, NHR25 or N(CH3)2, in particular of the fomula OR24;
R24 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having in total 1 to 18 carbon atoms;
R25 is hydrogen, (C~-Cg)alkyl, (C~-Cs)alkoxy or substituted or unsubstituted phenyl;
R26 is hydrogen, (C~-Cg)alkyl, (Ct-Cg)haloalkyl, (Ct-C4)alkoxy-(Ct-C4)alkyl, (Ct-Cg)hydroxyalkyl, (Cg-C~2)cycloalkyl or tri-(Ct -C4)-alkylsilyl;
R2~, R28, R29 are identical or different hydrogen, (Ct-Cg)alkyl, (Ct-Cg}haloalkyl, (C3-C~2)cycloalkyl or substituted or unsubstituted phenyl;
R21 is (C1-C4)alkYl, (C1-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)-haloalkenyl, (Cg-C~)cycloalkyl, preferably dichloromethyl;
R22, R23 is identical or different hydrogen, (Ct-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (Ct-C4)haloalkyl, (C2-C4)haloalkenyl, (Ct-C4)alkylcarbamoyl-(Ct-C4)alkyl, (C2-C4)-alkenylcarbamoyl-(Ct-C4)alkyl, (Ct-C4)alkoxy-(Ct-C4)alkyl, dioxolanyl-(Ct-C4)alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R22 and R23 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring;
b) one or more compounds from the group consisting of:
1,8-naphthalic anhydride, methyl diphenylmethoxyacetate, cyanomethoxyimino(phenyl)acetonitrile (cyometrinil), 1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil), 4'-chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime (fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim), benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191 ), N-(4-methylphenyl)-N'-(1-methyl-1-phenylethyl)urea (dymron), 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-naphthoylsulfamoyl)phenyl]-3,3-dimethylurea, (2,4-dichlorophenoxy}acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), .
1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor) and their salts and esters, preferably (C~-Cg);
c) N-acylsulfonamides of the formula (V) and their salts, 0 0 (R34~m N \ / S_N
o (~) ~R32~n where R3~ is hydrogen, a hydrocarbon radical, a hydrocarbonoxy radical, a hydrocarbonthio radical or a heterocyclyl radical which is preferably bonded via a carbon atom, each of the last-mentioned 4 radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, carboxamide, sulfonamide and radicals of the formula -Za-Ra , each hydrocarbon moiety preferably having 1 to 20 carbon atoms and a carbon-containing radical R3~ inclusive of substituents preferably having 1 to 30 carbon atoms;
R31 is hydrogen or (C~-C4)alkyl, preferably hydrogen, or R3~ and R31 together with the group of the formula -CO-N- are the radical of a 3- to 8-membered saturated or unsaturated ring;
R32 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, CONH2, S02NH2 or a radical of the formula _Zb_Rb;
R33 is hydrogen or (C~-C4)alkyl, preferably H;
R34 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH2, S02NH2 or a radical of the formula -Z~-R~;
Ra is a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and di [(C1-C4)alkyl]amino, or is an alkyl radical in which more than one, preferably 2 or 3, nonadjacent CH2 groups are each replaced by an oxygen atom;
Rb,R° identical or different are a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halo(C1-C4)alkoxy, mono- and di[(C1-C4)alkyl]amino, or are an alkyl radical in which more than one, preferably 2 or 3, nonadjacent CH2 groups are each replaced by an oxygen atom;
Za is a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO-, -S-CO-, -SO-, -S02-, -NR*-, -CO-NR*-, -NR*-CO-, -S02-NR*- or -NR*-S02-, the bond shown on the right of the divalent group in question being the bond to the radical Ra and the R* in the last-mentioned 5 radicals independently of one another being in each case H, (C~-C4)alkyl or halo(C~-C4)alkyl;
Zb,Z~ independently of one another are a direct bond or a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO-, -S-CO-, -SO-, -S02-, -NR*-, -S02-NR*-, -NR*-S02-, -CO-NR*- or -NR*-CO-, the bond shown on the right of the divalent group in question being the bond to the radical Rb or R~, respectively, and the R* in the last-mentioned 5 radicals independently of one another being in each case H, (C1-C4)alkyl or halo(C~-C4)alkyl;
n is an integer from 0 to 4, preferably 0, 1 or 2, in particular 0 or 1, and m is an integer from 0 to 5, preferably 0, 1, 2 or 3, in particular 0, 1 or 2;

' 8 d) acylsulfamoylbenzamides of the formula (VI), if appropriate in salt form, O
N _ O O
S-N y (R~?m O I X
(R~~ R3s where X3 is CH or N;
R~ is hydrogen, heterocyclyl or a hydrocarbon radical, the two last mentioned radicals optionally being substituted by one or more, identical or different radicals selected from the group consisting of halogen, cyano, vitro, amino, hydroxyl, carboxyl, CHO, CONH2, S02NH2 and Za-Ra ;
R36 is hydrogen, hydroxyl, (C~-Cg)alkyl, (C2-Cg)alkenyl, (C2-Cg)alkynyl, (C~-Cg)alkoxy, (C2-Cg)alkenyloxy, the five last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, hydroxyl, (C~-C4)alkyl, (Ct-C4)alkoxy and (C~-C4)alkylthio, or R35 and R36 together with the nitrogen atom to which they are attached are a 3- to 8-membered saturated or unsaturated ring;
R3~ is halogen, cyano, vitro, amino, hydroxyl, carboxyl, CHO, CONH2, S02NH2 or Zb-Rb;
R38 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl;
R39 is halogen, cyano, vitro, amino, hydroxyl, carboxyl, phosphoryl, CHO, CONH2, S02NH2 or Z~-R~;
Ra is a (C2-C2p)alkyl radical whose carbon chain is interrupted once or more by oxygen atoms, or is heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals optionally being substituted by one or more, identical or different radicals selected from the group consisting of halogen, cyano, vitro, amino, hydroxyl, mono- and di[(C~-C4)alkyl]amino;
Rb, R~ identical or different are a (C2-C2p)alkyl radical whose carbon chain is interrupted once or more by oxygen atoms, or are heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals optionally being substituted by one or more, identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, (C1-C4)haloalkoxy, mono- and di[(C~-C4)-alkyl]amino;
Za is a divalent unit selected from the group consisting of O, S, CO, CS, C(O)O, C(O)S, SO, S02, NRd, C(O)NRd or S02NRd;
Zb, Z~ identical or different are a direct bond or a divalent unit selected from the group consisting of O, S, CO, CS, C(O)O, C(O)S, SO, S02, NRd, S02NRd or C(O)NRd;
Rd is hydrogen, (C~-C4)alkyl or (C~-C4)haloalkyl;
n is an integer from 0 to 4, and m in the event that X is CH, is an integer from 0 to 5 and, in the event that X is N, an integer from 0 to 4;
e) compounds of the formula (VII), R°°
Q'\.
,.
~E)m (VII) /G
(~2 R''~
where the symbols and indices have the following meanings:
R~ is H, (C1-C4)alkyl, (C~-C4)alkyl substituted by (C1-C4)alkyl-X4 or (C~-C4)haloalkyl-X4; (C~-C4)haloalkyl, N02, CN, -COO-R43, NR2~, S02NR245 or CONR2~;
R4~ is H, halogen, (C~-C4)alkyl, CF3, (C1-C4)alkoxy or (C~-C4)halo-alkoxy;
R42 is H, halogen or (C~-C4)alkyl;
Q1, Q2, E, G are identical or different, -O-, -S-, -CR24~-, -CO-, NR~- or a group of the formula (VIII), ~ C=CH-O-CR2~-(CO)-A (VIII) with the proviso that a) at least one of the groups Q1, Q2, E, G is a carbonyl group, that exactly one of this group is a radical of the formula (VIII) and that the group of the formula (VIII) is adjacent to a carbonyl group, and Vii) two adjacent groups Qt , Q2, E and G cannot simultaneously be oxygen;
Ra is identical or different H or (C1-Cg)alkyl or the two radicals Ra together are (C2-C6)alkylene;
5 A is Rb -Y3- or -NR249;
X4 is -O- or -S(O)p-;
Y3 is -O- or -S-;
Rb is H, (Ct-Cg)alkyl, (C~-Cg)haloalkyl, (C1-C4)alkoxy(C~-Cg)alkyl, (Cg-Cg)alkenyloxy(C~-Cg)alkyl, or phenyl(Ct-Cg)alkyl, the phenyl 10 ring optionally being substituted by halogen, (C1-C4)alkyl, CF3, methoxy or methyl-S(O)p; (C3-C6)alkenyl, (C3-C6)haloalkenyl, phenyl(C3-C6)alkenyl, (C3-C6)alkynyl, phenyl(C3-C6)alkynyl, oxetanyl, furfuryl, tetrahydrofuryl;
R43 is H or (Ct-C4)alkyl;
R44 is identical or different H, (C~-C4)alkyl, (C~-C4)alkylcarbonyl or the two radicals R~ together are (C4-C5)alkylene;
R45, R46 are independently of one another in each case identical or different H, (Ct-C4)alkyl, or the two radicals R~ and/or R46 together are (C4-C5)alkylene, it being possible for one CH2 group to be replaced by O or S or by one or two CH2 groups to be replaced by _NRc_ Rc is H or (Ct-Cg)alkyl;
R4~ is identical or different H, (C~-C8)alkyl or the two radicals R4~
together are (C2-C6)alkylene;
R48 is H, (Ct-Cg)alkyl, substituted or unsubstituted phenyl, or benzyl which is unsubstituted or substituted on the phenyl ring;
R49 is identical or different H, (Ct-Cg)alkyl, phenyl, phenyl(Ct-Cg)alkyl, it being possible for a phenyl ring to be substituted by F, CI, Br, N02, CN, OCH3, (C1-C4)alkyl or CH3S02_; or is (Ct-C4)alkoxy-(Ct-Cg)alkyl, (C3-C6)alkenyl, (Cg-C6)alkynyl, (C3-C6)cycloalkyl or two radicals R49 together are (C4-C5)alkylene, it being possible for one CH2 group to be replaced by O or S or for one or two CH2 groups to be replaced by -NRd-;
Rd is H or (C~-C4)alkyl;
m" is 0 or 1 and p is 0, 1 or 2;
inclusive of the stereoisomers and of the salts conventionally used in agriculture.

Herbicidally effective amount means, for the purposes of the invention, an amount of one or more herbicides which~is suitable for adversely affecting plant growth.
Antidote-effective amount means, for the purposes of the invention, an amount of one or more safeners which is suitable for at least partially counteracting the phytotoxic effect of a herbicide or herbicide mixture on a useful plant.
Unless specifically defined otherwise, the following definitions generally apply to the radicals in formulae (I) to (VIII) and the subsequent formulae.
The radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and/or substituted radicals in the carbon skeleton can each be straight-chain or branched.
Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl and the like, preferably have 1 to 4 carbon atoms and are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl. Alkenyl and alkynyl radicals have the meaning of the unsaturated radicals which are possible and which correspond to the alkyl radicals; alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alkynyl is, for example, propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methylbut-3-in-1-yl. "(C1-C4)-Alkyl" is the abbreviation for alkyl having 1 to 4 carbon atoms; this also applies analogously to other general definitions of radicals whose ranges of the possible number of carbon atoms is given in brackets.
Cycloalkyl is preferably a cyclic alkyl radical having 3 to 8, preferably 3 to 7, especially preferably 3 to 6, carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Cycloalkenyl and cycloalkynyl denote corresponding unsaturated compounds.
Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl or alkynyl which are partially or fully substituted by halogen, preferably fluorine, chlorine andlor bromine, in particular by fluorine or chlorine, for example CFg, CHF2, CH2F, CFgCF2, CH2FCHCI, CCIg, CHCI2, CH2CH2C1. Haloalkoxy is, for example, OCF3, OCHF2, OCH2F, CF3CF20, OCH2CF3 and OCH2CH2C1. This also applies analogously to other halogen-substituted radicals.
A hydrocarbon radical can be an aromatic or an aliphatic hydrocarbon radical, an aliphatic hydrocarbon radical being, generally, a straight-chain or branched saturated or unsaturated hydrocarbon radical, preferably having 1 to 18, especially preferably 1 to 12, carbon atoms, for example alkyl, alkenyl or alkynyl.
An aliphatic hydrocarbon radical preferably means alkyl, alkenyl or alkynyl having up to 12 carbon atoms; this also applies analogously to an aliphatic hydrocarbon radical in a hydrocarbonoxy radical.
Aryl is, generally, a mono-, bi- or polycyclic aromatic system having preferably 6-20 carbon atoms, preferably 6 to 14 carbon atoms, especially preferably 6 to 10 carbon atoms, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl and fluorenyl, especially preferably phenyl.
A heterocyclic ring, heterocyclic radical or heterocyclyl denotes a mono-, bi-or polycyclic ring system which is saturated, unsaturated and/or aromatic and has one or more, preferably 1 to 4, hetero atoms, preferably selected from the group consisting of N, S and O.
Preferred are saturated heterocycles having 3 to 7 ring atoms and one or two hetero atoms selected from the group consisting of N, O and S, the chalcogens not being adjacent. Especially preferred are monocyclic rings having 3 to 7 ring atoms and one hetero atom selected from the group consisting of N, O and S, and also morpholine, dioxolane, piperazine, imidazoline and oxazolidine. Very especially preferred saturated heterocycles are oxirane, pyrrolidone, morpholine and tetrahydrofuran.
Also preferred are partially unsaturated heterocycles having 5 to 7 ring atoms and one or two hetero atoms selected from the group consisting of N, O and S. Especially preferred are partially unsaturated heterocycles having 5 to 6 ring atoms and one hetero atom selected from the group consisting of N, O and S. Very especially preferred partially unsaturated heterocycles are pyrazoline, imidazoline and isoxazoline.

Also preferred is heteraryl, for example mono- or bicyclic aromatic heterocycles having 5 to 6 ring atoms which contain one to four hetero atoms selected from the group consisting of N, O, S, the chalcogens not being adjacent. Especially preferred are monocyclic aromatic heterocycles having 5 to 6 ring atoms and containing a hetero atom selected from the group consisting of N, O and S, and also pyrimidine, pyrazine, pyridazine, oxazole, thiazole, thiadiazole, oxadiazole, pyrazole, triazole and isoxazole.
Very especially preferred are pyrazole, thiazole, triazole and furan.
Substituted radicals such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl such as phenyl and arylalkyl such as benzyl, or substituted heterocyclyl, are a substituted radical derived from the unsubstituted skeleton, the substituents preferably being one or more, preferably 1, 2 or 3, in the case of CI and F also up to the maximum possible number of, substituents selected from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, vitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino such as acylamino, mono- and dialkylamino and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals, also alkyl and haloalkyl, and unsaturated aliphatic substituents corresponding to the abovementioned saturated hydrocarbon-containing substituents, preferably alkenyl, alkynyl, alkenyloxy, alkynyloxy. In the case of radicals with carbon atoms, those having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred. Preferred are, as a rule, substitutents selected from the group consisting of halogen, for example fluorine or chlorine, (C1-C4)alkyl, preferably methyl or ethyl, (Ct-C4)haloalkyl, preferably trifluoromethyl, (Ct-C4)alkoxy, preferably methoxy or ethoxy, (C1-C4)haloalkoxy, vitro and cyano. Especially preferred are the substituents methyl, methoxy and chlorine.
Mono- or disubstituted amino denotes a chemically stable radical selected from the group consisting of the substituted amino radicals which are N-substituted, for example, by one or two identical or different radicals selected from the group consisting of alkyl, alkoxy, acyl and aryl, preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles. Alkyl radicals having 1 to 4 carbon atoms are preferred. Aryl is preferably phenyl. Substituted aryl is preferably substituted phenyl. As far as acyl is concerned, the definition given further below applies, preferably (C1-C4)alkanoyl. This also applies analogously to substituted hydroxylamino or hydrazino.
Optionally substituted phenyl is, preferably, phenyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, in the case of halogen such as CI and F also up to pentasubstituted, by identical or different radicals selected from the group consisting of (Ct-C4)alkyl, (C1-C4)alkoxy, (C~-C4)haloalkyl, (C1-C4)haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophen~rl, 2-, 3- and 4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
An acyl radical denotes the radical of an organic acid preferably having up to 6 carbon atoms, for example the radical of a carboxylic acid and radicals of acids derived therefrom such as of thiocarboxylic acid, optionally N-substituted iminocarboxylic acids, or the radical of carbonic monoesters, optionally N-substituted carbamic acids, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids. Acyl is, for example, formyl, alkylcarbonyl such as (Ct-C4-alkyl)carbonyl, phenylcarbonyl, it being possible for the phenyl ring to be substituted, for example as indicated above for phenyl, or alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl or N-alkyl-1-iminoalkyl.
The formulae (I) to (VIII) also encompass all stereoisomers whose atoms have the same topological linkage, and mixtures of these stereoisomers.
Such compounds contain one or more asymmetric carbon atoms or else double bonds which are not especially mentioned in the formulae. The possible stereoisomers which are defined by their specific spatial form, such as enantiomers, diastereomers, Z- and E-isomers, may be obtained by customary methods from stereoisomer mixtures or else be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.
Herbicides of the formula (I) are disclosed for example in EP-A-273 417, which contains detailed information on preparation methods, starting materials and preferred compounds. This publication is expressly referred to; it is incorporated into the present description by reference.

The compounds of the formula (II) are disclosed, for example, in EP-A-0 333 131 (ZA-89/1960), EP-A-0 269 806 (US-A-4,891,057), EP-A-0 346 620 (AU-A-89/34951 ), EP-A-0 174 562, EP-A-0 346 620 (WO-A-91/08 202), WO-A-91/07 874 or WO-A 95/07 897 (ZA 94/7120) and 5 in the literature cited therein or can be prepared by or analogously to the processes described therein. The compounds of the formula (III) are disclosed in EP-A-0 086 750, EP-A-0 94349 (US-A-4,902,340), EP-A-0 191736 (US-A-4,881,966) and EP-A-0 492 366 and in the literature cited therein or can be prepared by or analogously to the processes 10 described therein. Some compounds are furthermore described in EP-A-0 582 198.
The compounds of the formula (IV) are disclosed in a large number of patent applications, for example US-A-4,021,224 and US-A-4,021,229.
15 Compounds of group B (b) are furthermore known from CN-A-87/102 789, EP-A-365484 and from "The Pesticide Manual", The British Crop Protection Council and the Royal Society of Chemistry, 11 th edition, Farnham 1997.
The compounds of group B (c) are described in WO-A-97/45016, those of group B (d) in German Patent Application 197 42 951.3, and those of group B (e) in WO-A 98/13 361.
The cited publications contain extensive information on preparation processes and starting materials and preferred compounds. These publications are referred to expressly and they are incorporated herein by refe rence.
Preferred herbicide/safener combinations are those which comprise safeners of the formula (II) and/or (III) in which the symbols and indices have the following meanings:
R24 is hydrogen, (C~-C~g)alkyl, (C3-C~2)cycloalkyl, (C2-C8)alkenyl and (C2-C~ g)alkynyl, it being possible for the carbon-containing groups to be substituted by one or more, preferably up to three, radicals R50 is identical or different halogen, hydroxyl, (C~-Cg)alkoxy, (C1-Cg)alkylthio, (C2-C8)alkenylthio, (C2-Cg)alkynylthio, (C2-Cg)-alkenyloxy, (C2-Cg)alkynyloxy, (C3-C~)cycloalkyl, (Cg-C~)cyclo-alkoxy, cyano, mono- and di(C1-C4)alkyl)amino, carboxyl, (C~-Cg)alkoxycarbonyl, (C2-Cg)alkenyloxycarbonyl, (C~-Cg)alkyl-thiocarbonyl, (C2-Cg)alkynyloxycarbonyl, (C~-C8)alkylcarbonyl, (C2-Cg)alkenylcarbonyl, (C2-Cg)alkynylcarbonyl, 1-(hydroxyimino)-{C~-C6)alkyl, 1-[(C1-C4)alkylimino](C~-C4)alkyl, 1-[(C~-C4)alkoxy-imino](C~-Cg)alkyl, (C~-Cg)alkylcarbonylamino, (C2-Cg)alkenyl-carbonylamino, (C2-Cg)alkynylcarbonylamino, aminocarbonyl, (C~-C8)alkylaminocarbonyl, di{C1-Cg)alkylaminocarbonyl, (C2-Cg)-alkenylaminocarbonyl, (C2-Cg)alkynylaminocarbonyl, (C~-Cg)alkoxy-carbonylamino, (C~-C8)alkylaminocarbonylamino, {C1-Cg)alkyl-carbonyloxy, which is unsubstituted or substituted by RSp, (C2-Cg)alkenylcarbonyloxy, (C2-Cg)alkynylcarbonyloxy, (C~-Cg)-alkylsulfonyl, phenyl, phenyl(C~-Cg)alkoxy, phenyl(C1-Cg)alkoxy-carbonyl, phenoxy, phenoxy(C~-Cg)alkoxy, phenoxy(C1-Cg)alkoxy-carbonyl, phenylcarbonyloxy, phenylcarbonylamino, phenyl(C1-Cg)-alkylcarbonylamino, it being possible for the last-mentioned 9 radicals to be unsubstituted or mono- or polysubstituted in the phenyl ring, preferably up to trisubstituted, by radicals R52; SiR'g, -O-SiR'g, R'gSi-(C~-Cg)alkoxy, -CO-O-NR'2, -O-N=CR'2, -N=CR'2, -O-NR'2~ -NR'2~ CH(OR')2~ -O-(CH2)m-CH(OR')2, -CR"'(OR')2~ -O-(CH2)mCR"'(OR")2 or by R"O-CHR"'CHCOR"-(C1-Cg)alkoxy, R51 is identical or different halogen, nitro, (C~-C4)alkoxy and phenyl which is unsubstituted or substituted by one or more, preferably up to three, radicals R5~ ;
R52 is identical or different halogen, (C1-C4)alkyl, (C~-C4)alkoxy, (C~-C4)haloalkyl, (C1-C4)haloalkoxy or nitro;
R' is identical or different hydrogen, (C~-C4)alkyl, phenyl which is unsubstituted or substituted by one or more, preferably up to three, radicals R52, or two radicals R' together form a (C2-Cg)alkanediyl chain;
R" is identical or different (C~-C4)alkyl or two radicals R" together form a (C2-C6)alkanediyl chain;
R"' is hydrogen or (C~-C4)alkyl;
m is 0, 1, 2, 3, 4, 5 or 6.
Especially preferred are herbicide/safener combinations according to the invention comprising safener of the formula (II) and/or (III) where the symbols and indices have the following meanings:
R24 is hydrogen, (C1-Cg)alkyl or (Cg-C7)cycloalkyl, the abovementioned carbon-containing radicals being unsubstituted or mono- or polysubstituted by halogen or mono- or disubstituted, preferably monosubstituted, by radicals R5o , R5o is identical or different hydroxyl, (C~-C4)alkoxy, carboxyl, (C1-C4)alkoxycarbonyl, (C2-Cg)alkenyloxycarbonyl, (C2-Cg)alkynyl oxycarbonyl, 1-(hydroxyimino)(C~-C4)alkyl, 1-[(C1-C4)alkylimino]
(C~-C4)alkyl and 1-[(C~-C4)alkoxyiminoJ(C1-C4)alkyl; -SiR'g, -O-N=CR'2, -N=CR'2, -NR'2, and -O-NR'2, in which R' is identical or different hydrogen, (C1-C4)alkyl or, as a pair, a (C4-C5)alkanediyl chain, R2~, R28, R29 are identical or different hydrogen, (C1-Cg)alkyl, (C~-Cg)haloalkyl, (Cg-C~)cycloalkyl or phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, amino, mono- and di [(C1-C4)alkyl]amino, (C1-C4)alkyl, (C1-C4)haloalkyl, (C~-C4)alkoxy, (C~-C4)haloalkoxy, (C~-C4)alkylthio and (C~-Cq.)alkylsulfonyl;
R26 is hydrogen, (C~-Cg)alkyl, (C~-C8)haloalkyl, (C~-C4)alkoxy)(C1-C4)-alkyl, (C~-Cg)hydroxyalkyl, (Cg-C~)cycloalkyl or tri(C1-C4)alkylsilyl, R1 ~, R~ 9 are identical or different, halogen, methyl, ethyl, methoxy, ethoxy, (C~ or C2)haloalkyl, preferably hydrogen, halogen or (C1 or C2)haloalkyl.
Very especially preferred safeners are those in which the symbols and indices in formula (II) have the following meanings:
R1~ is halogen, nitro or (C1-C4)haloalkyl;
n' is 0, 1, 2 or 3;
R~8 is a radical of the formula OR24, R24 is hydrogen, (C~-Cg)alkyl or (C3-C~)cycloalkyl, the above carbon-containing radicals being unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different halogen radicals or up to disubstituted, preferably monosubstituted by identical or different radicals selected from the group consisting of hydroxyl, (C~-C4)alkoxy, (C~-C4)alkoxycarbonyl, (C2-Cg)alkenyloxy-carbonyl, (C2-Cg)alkynyloxycarbonyl, 1-(hydroxyimino)(C1-C4)alkyl, 1-[(C~-C4)alkylimino](C~-C4)alkyl, 1-[(C~-C4)alkoxyimino](C~-Cq,)-alkyl and radicals of the formulae -SiR'g, -O-N=R'2, -N=CR'2, -NR'2 and -O-NR'2, the radicals R' in the abovementioned formulae being identical or different hydrogen, (C~-C4)alkyl or, in pairs, (C4 or C5)alkanediyl;

R2~, R28, R29 are identical or different hydrogen, (C1-Cg)alkyl, (C~-Cg)haloalkyl, (C3-C~)cycloalkyl or phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting- of halogen, (C~-C4)alkyl, (C1-C4)alkoxy, nitro, (C~-C4)haloalkyl and (C1-C4)haloalkoxy, and R26 is hydrogen, (C1-Cg)alkyl, (C1-Cg)haloalkyl, (C~-C4)alkoxy-(C~-C4)-alkyl, (C1-C6)hydroxyalkyl, (C3-C7)cycloalkyl or tri(C1-C4)alkylsilyl.
Very especially preferred safeners are also those of the formula (III) in which the symbols and indices have the following meanings:
R~9 is halogen or (C~-C4)haloalkyl;
n' is 0, 1, 2 or 3, where (R19)n' is preferably 5-CI ;
R2~ is a radical of the formula OR24;
T is CH2 or CH(COO-(C,-C3-alkyl)) and R24 is hydrogen, (C~-Cg)alkyl, (C1-Cg)haloalkyl or (C~-C4)alkoxy-(C1-C4)alkyl, preferably (C~-Cg)alkyl.
Particularly preferred are the safeners of the formula (II) in which the symbols and indices have the following meanings:
W is (W 1 );
R17 is halogen or (C1-C2)haloalkyl;
n' is 0, 1, 2 or 3, (R~ ~)n~ preferably being 2,4-CI2;
R18 is a radical of the formula OR24; , R24 is hydrogen, (C~-Cg)alkyl, (C~-C4)haloalkyl, (C1-C4)hydroxyalkyl, (C3-C7)cycloalkyl, (C~-C4)alkoxy(C1-C4)alkyl or tri(C1-C2)alkylsilyl, preferably (C1-C4)alkyl;
R2~ is hydrogen, (C1-Cg)alkyl, (C1-C4)haloalkyl or (Cg-C7)cycloalkyl, preferably hydrogen or (C1-C4)alkyl, and R26 is hydrogen, (C~-Cg)alkyl, (C1-C4)haloalkyl, (C~-C4)hydroxyalkyl, (Cg-C7)cycloalkyl, (C1-C4)alkoxy(C1-C4)alkyl or tri(C1-C2)alkylsilyl, preferably hydrogen or (C~-C4)alkyl.
Also particularly preferred are herbicidal compositions comprising a safener of the formula (II) where the symbols and indices have the following meanings:
W is (W2);
R~7 is halogen or (C~-C2)haloalkyl;
n' is 0, 1, 2 or 3, (R1~)n~ preferably being 2,4-C12;

R~ 8 is a radical of the formula OR24;
R24 is hydrogen, (C~-Ca)alkyl, (C~-C4)haloalkyl, (C1-C4)hydroxyalkyl, (Cg-C~)cycloalkyl, (C1-C4)alkoxy)-C1-C4-alkyl or tri(Ct-C2)alkylsilyl, preferably (C1-C4)alkyl, and R2~ is hydrogen, (C1-Cg)alkyl, (C~-C4)haloalkyl, (C3-C~)cycloalkyl or phenyl, preferably hydrogen or (C1-C4)alkyl.
Also particularly preferred are safeners of the formula (II) where the symbols and indices have the following meanings:
W is (V113);
R17 is halogen or (C1-C2)haloalkyl;
n' is 0, 1, 2 or 3, (R1~)n~ preferably being 2,4-CI2;
R~$ is a radical of the formula OR24;
R24 is hydrogen, (C~-Cg)alkyl, (C1-C4)haloalkyl, (C~-C4)hydroxyalkyl, (C3-C~)cycloalkyl, (C~-C4)alkoxy(C~-C4)alkyl or tri(C1-C2)alkylsilyl, preferably (Ct-C4)alkyl, and R28 is (C1-Cg)alkyl or (C1-C4)haloalkyl, preferably C1-haloalkyl.
Also particularly preferred are safeners of the formula (II) where the symbols and indices have the following meanings:
W is (1N4);
R~~ is halogen, nitro, (C~-C4)alkyl, (C1-C2)haloalkyl, preferably CF3 or (C~-C4)alkoxy;
n' is 0, 1, 2 or 3;
m' is0orl;
R~8 is a radical of the formula OR24 ;
R24 is hydrogen, (C~-C4)alkyl, carboxy(C~-C4)alkyl, (Ct-C4)alkoxy carbonyl(C~-C4)alkyl, preferably (C~-C4)alkoxy-CO-CH2-, (C~-C4)alkoxy-CO-C(CHg)H-, HO-CO-CH2- or HO-CO-C(CH3)H-, and R29 is hydrogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (Cg-C~)cycloalkyl or phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C~-C4)alkyl, (C~-C4)haloalkyl, nitro, cyano and (Ct-C4)alkoxy.
The following groups of compounds are particularly suitable as safeners for the herbicidal active substances of the formula (I):

a) compounds of the dichlorophenylpyrazoiine-3-carboxylic acid type {i.e. of the formula (II), where W = (1N1) and (R~7)n~ = 2,4-CI2), preferably compounds such as ethyl 1-{2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (II-1, 5 mefenpyr-diethyl), and related compounds as they are described in W O-A 91 /07874;
b) dichlorophenylpyrazolecarboxylic acid derivatives (i.e. of the formula (II), where W = (UV2) and (R~7)n~ = 2,4-CI2), preferably compounds such as ethyl 1-{2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate 10 (I I-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (II-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (II-4), ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (II-5) and related compounds as they are described in EP-A-0 333 131 and EP-A-0 269 806.
15 c) Compounds of the triazolecarboxylic acid type (i.e. of the formula (II), where W = (W3) and (R~~)n~ = 2,4-CI2), preferably compounds such as fenchlorazol-ethyl, i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1 H)-1,2,4-triazole-3-carboxylate (II-6), and related compounds (see EP-A-0 174 562 and EP-A-0 346 620);
20 d) compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid type or the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (where W - (W4)), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (II-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (II-8) and related compounds as they are described in WO-A-91/08202, or of the ethyl 5,5-diphenyl-2-isoxazolinecarboxylate type (II-9, isoxadifen-ethyl), the n-propyl 5,5-diphenyl-2-isoxazolinecarboxylate type (II-10) or the ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate type (I I-11 ), as they are described in WO-A-95/07897.
e) Compounds of the 8-quinolinoxyacetic acid type, for example those of the formula (III), where (R~ 9)n~ = 5-CI, R2~ = OR24 and T = CH2, preferably the compounds 1-methylhexyl (5-chloro-8-quinolinoxy)acetate (III-1, cloquintocet-mexyl), 1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (III-2), 4-allyloxy-butyl (5-chloro-8-quinolinoxy)acetate (III-3), 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (III-4), ethyl (5-chloro-8-quinolinoxy)acetate (III-5), methyl (5-chloro-8-quinolinoxy)acetate (III-6), ' 21 allyl (5-chloro-8-quinolinoxy)acetate (III-7), 2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate (III-8), 2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (III-9) and related compounds as they are described in EP-A-0 860 750, EP-A-0 094 349 and EP-A-0 191 736 or EP-A-0 492 366.
f) Compounds of the (5-chloro-8-quinolinoxy)malonic acid type, i.e. of the formula (III), where (R~9)~~ = 5-CI, R2~= OR24, T = -CH(COO-allryl)-, preferably the compounds diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate and related compounds as they are described in EP-A-0 582 198.
g) compounds of the dichloroacetamide type, i.e. of the formula (IV), preferably:
N,N-diallyl-2,2-dichloroacetamide (dichlormid, disclosed in US-A 4,137,070), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (IV-1, benoxacor, disclosed in EP 0 149 974), N1,N2-diallyl-N2-dichloroacetylglycinamide (DKA-24, disclosed in HU 2143821 ), 4-dichloroacetyl-1-oxa-4-aza-spiro[4,5]decane (AD-67), 2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 3-dichloroacetyl-2,2,5-trimethyloxazolidine, 3-dichloroacetyl-2,2-dimethyl-5-phenyloxazolidine, 3-dichloroacetyl-2,2-dimethyl-5-(2-thienyl)oxazolidine, 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON 13900), 1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidine-6(2H)-one (dicyclonon, BAS 145138), h) compounds of group B(b), preferably 1,8-naphthalic anhydride, methyl diphenylmethoxyacetate, cyanomethoxyimino(phenyl)acetonitrile (cyometrinil), 1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil), 4'-chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime (fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorirn), benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole), 2-dichloromethyl-2-methyl-1,3-dioxolan (MG-191 ), N-(4-methylphenyl)-N'-(1-methyl-1-phenylethyl)urea (dymron), 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-naphthoylsulfamoyl)phenyl]-3,3-dimethylurea, (2,4-dichlorophenoxy)acetic acid (h -1,2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (h -2, mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (h -3, MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor) and their salts and esters, preferably (C~-Cg).
Furthermore preferred as safeners are compounds of the formula (V) or their salts, where R3~ is hydrogen, (C~-Cg)alkyl, (C3-Cg)cycloalkyl, furanyl or thienyl, it being possible for each of the last-mentioned 4 radicals to be unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C1-C4)alkoxy, halo(C~-Cg)-alkoxy and (C1-C4)alkylthio and, in the case of cyclic radicals, also (C~-C4)alkyl and (C1-Cq,)haloalkyl, R31 is hydrogen, R32 is halogen, halo(C~-C4)alkyl, halo(C~-C4)alkoxy, (C1-C4)alkyl, (C~-C4)alkoxy, (C~-C4)alkylsulfonyl, (C~-C4)alkoxycarbonyl or (C~-C4)alkylcarbonyl, preferably halogen, (C~-C4)haloalkyl, such as trifluoromethyl, (C~-C4)alkoxy, halo(C1-C4)alkoxy, (C1-C4)alkoxycarbonyl or (C~ -C4)alkylsulfonyl, R33 is hydrogen, R34 is halogen, (C1-C4)alkyl, halo(C1-C4)alkyl, halo(C~-C4)alkoxy, (Cg-Cg)cycloalkyl, phenyl, (C~-C4)alkoxy, cyano, (C1-C4)alkylthio, (C~-C4)alkylsulfinyl, (C~-C4)alkylsulfonyl, (C~-C4)alkoxycarbonyl or (C~ -C4)alkylcarbonyl, preferably halogen, (C~-C4)alkyl, (C~-C4)haloalkyl, such as trifluoromethyl, halo(Ct-C4)alkoxy, (Ct-C4)alkoxy or (C1-C4)-alkylthio, n is 0, 1 or 2 and m is 1 or 2.
Furthermore preferred are safeners of the formula (VI), in which X3 is CH;
R35 is hydrogen, (Ct-Cg)alkyl, (C3-Cg)cycloalkyl, (C2-Cg)alkenyl, (C5-C6)cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl having up to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it being possible for the six last mentioned radicals to be optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, (C~-Cg)alkoxy, (C1-Cg)haloalkoxy, (C~-C2)alkylsulfinyl, (C~-C2)alkylsulfonyl, (Cg-Cg)cycloalkyl, (C~-C4)alkoxycarbonyl, (C~-C4)alkylcarbonyl and phenyl and, in the case of cyclic radicals, also (Ct-C4)alkyl and (C~-C4)haloalkyl;
R36 is hydrogen, (C~-Cg)alkyl, (C2-Cg)alkenyl, (C2-Cg)alkynyl, it being possible for the three last-mentioned radicals optionally to be substituted by one or more, identical or different substituents selected from the group consisting of halogen, hydroxyl, (C1-Cq.)alkyl, (C1-C4)alkoxy and (C~-C4)alkylthio;
R37 is halogen, (C~-C4)haloalkyl, (C~-C4)haloalkoxy, nitro, (C~-C4)alkyl, (C1-C4)alkoxy, (C~-C4)alkylsulfonyl, (C~-C4)alkoxycarbonyl or (C~-Cq.)alkylcarbonyl;
R38 is hydrogen;
R39 is halogen, nitro, (Ct-C4)alkyl, (C1-C4)haloalkyl, (Ct-C4)haloalkoxy, (C3-Cg)cycloalkyl, phenyl, (Ct-C4)alkoxy, cyano, (Ct-C4)alkylthio, (Ct-C4)alkylsulfinyl, (Ct-C4)alkylsulfonyl, (C~-C4)alkoxycarbonyl or (C~-C4)alkylcarbonyl;
n is 0, 1 or 2 and m is 1 or 2.
Especially preferred amongst the safeners of the formula (VII) are the sub-groups which follow:
- compounds in which R48 and R49 = H, (C~-Cg)alkyl, phenyl, phenyl(C1-Cg)alkyl, (C~-C4)alkoxy-(C1-Cg)alkyl, (C3-Cg)alkenyl or (C3-Cg)alkynyl, it being possible for phenyl rings to be substituted by F, C1, Br, N02, CN, OCH3, (C~-C4)alkyl or CH3-S02-;
- compounds in which Ra = b , - compounds in which A = R -Y;
- compounds in which E = O;
- compounds in which Q1 = CR247;
- compounds in which R4~ = H;
compounds in which m" = 1 and E = O or S;
- compounds in which m" = 0;
- compounds in which R4~ to R~ are H, m" =1, E = O , 4t = CR247 and A = Rb-Y, in particular those where R4~ = H, Rb = CH3 and Y=O;
- compounds in which Q~ = CR24~ and m" equals 0, in particular those in which R~ and R4~ = H and A = Rb-Y where Rb is preferably methyl and Y is preferably O.
Examples of preferred combinations of herbicidal active substances (A) and safeners (B) are: (I - 1 ) + (I I - 1 ), (I - 1 ) + (I I - 9), (I -1 ) +
(II I - 1 ), (I - 1 ) +(IV-1),(I-1)+(h-1),(I-1)+(h-2)and(I-1)+(h-3).
The safeners (antidotes) of the formulae (II) - (VII) and the compounds of group B (b), for example safeners of the preferred groups a) to h), reduce or prevent phytotoxic effects which may occur when using the herbicidal active substances of the formula (I) in crops of useful plants without substantially affecting the efficacy of these herbicidal active substances against harmful plants. This allows the field of application of conventional crop protection products to be widened quite considerably and to be extended to, for example, crops such as wheat, barley, maize, rice and other crops in which use of the herbicides was hitherto impossible, or only limited, that is to say at low rates and with a restricted spectrum.
The herbicidal active substances and the mentioned safeners can be applied together (as a readymix or by the tank mix method) or in succession in any desired sequence. The weight ratio of safener:herbicidal active substance may vary within wide limits and is preferably in the range of from 1:100 to 100:1, in particular 1:10 to 10:1. The optimum amounts of herbicidal active substance and safener which are used in each case depend on the type of the herbicidal active substance used or on the safener used and on the species of the crop stand to be treated and can be determined in each individual case by simple routine preliminary experiments.
The main fields of application for the combinations according to the 5 invention are, in particular, maize and cereal crops (for example, wheat, rye, barley, oats), rice, sorghum, cotton and soybeans, preferably cereals, rice and maize.
Depending on their properties, the safeners present in the herbicidal 10 composition according to the invention can be used for pretreating the seed of a crop plant (seed dressing), or be incorporated into the seed furrows prior to sowing or applied together with the herbicide before or after plant emergence. The pre-emergence treatment includes not only treatment of the area under cultivation prior to sowing and treatment of the areas under 15 cultivation where the seeds have been planted but the plants have not yet emerged. The joint application together with the herbicide is preferred. To this end, tank mixes or readymixes may be employed.
The application rates of safener required may vary within wide limits 20 depending on indication and herbicidal active substance used and are generally in the range of from 0.001 to 5 kg, preferably 0.005 to 0.5 kg, of active substance per hectare.
The present invention furthermore relates to a method which comprises 25 applying a herbicidally active amount of the herbicidally active composition according to the invention to the harmful plants, crop plants, plant seeds or the area on which the plants grow. In this context, the antidote-effective amount of one or more safeners, preferably of one or more, in particular one, compound of the formula (II), (III), (IV), (V), (VI), (VII) andlor of group B (b) can be applied to the plants, plant seeds or the area on which the plants grow before, after or together with the herbicidally active substances) of the formula (I).
The herbicide/safener combination according to the invention may also be employed for controlling harmful plants in crops of genetically engineered plants which are either known or still to be developed. As a rule, the transgenic plants are distinguished by particular, advantageous properties, for example by resistance to certain crop protection agents, resistance to plant diseases or pathogens causing plant diseases such as particular insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the harvested material in terms of quantity, quality, storing properties, composition and specific constituents. Thus, there are known transgenic plants with an increased starch content or with an altered starch quality, or those where the harvested material has a different fatty acid composition.
The use of the combinations according to the invention in economically important transgenic crops of useful plants and ornamentals, for example cereals (for example wheat, barley, rye, oats), sorghum and millet, rice, cassava and maize, or else crops of sugar beet, cotton, soya, oilseed rape, potatoes, tomatoes, peas and other vegetables.
When the combinations according to the invention are applied in transgenic crops, effects on harmful plants to be observed in other crops are frequently accompanied by effects which are specific for application in the transgenic crop in question, for example an altered or specifically widened weed spectrum which can be controlled, altered application rates which may be used, preferably good compatibility with the herbicides to which the transgenic crop is resistant, and altered growth and yield of the transgenic crop plants.
The invention therefore also relates to the use of the herbicidally active composition according to the invention for controlling harmful plants in transgenic crop plants or crop plants which display tolerance as a result of selection-based breeding.
The safeners, preferably of the formulae (II) - (VII) and/or of group B (b), and the abovementioned herbicidal active substances of the formula (I) can be formulated, together or seperately in various ways, depending on the biological and/or chemico-physical parameters specified. Examples of possible formulations which are suitable are:
Wettable powders (WP), emulsifiable concentrates (EC), water-soluble powders (SP), water-soluble concentrates (SL), concentrated emulsions (BW) such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, capsule suspensions (CS), oil- or water-based dispersions (SC), suspoemulsions, suspension concentrates, dusts (DP), oil-miscible solutions (0L), seed-treatment products, granules (GR) in the form of microgranules, spray granules, coated granules and adsorption granules, granules for soil application or broadcasting, water-soluble granules (SG), water-dispersible granules (WG), ULV formulations, microcapsules and waxes.
These individual formulation types are known in principle and described, for example, in: Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4'" Edition 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker N.Y., 1973; K.
Martens, "Spray Drying Handbook", 3rd Edition 1979, G. Goodwin Ltd.
London.
The formulation auxiliaries which may be required, such as inert materials, surfactants, solvents and other additives are also known and described, for example, in: Watkins, "Handbook of 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.; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; 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. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4~' Edition 1986.
Based on these formulations, it is also possible to prepare combinations with other agrochemical active substances, for example with substances which act as crop protection agents, such as insecticides, acaricides, herbicides, fungicides, or safeners, fertilizers and/or growth regulators, for example in the form of a readymix or tank mix.
Wettable powders are preparations which are uniformly dispersible in water and which, besides the active substance, also comprise ionic and/or nonionic surfactants {wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfon-ate, or else sodium oleoylmethyltaurinate, in addition to a diluent or inert substance. To prepare the wettable powders, the active substances, for example the herbicidally active substances and/or the safeners, are ground finely, for example in customary apparatus such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.
Emulsifiable concentrates are prepared, for example, by dissolving the active substance, for example the herbicidally active substance andlor the safener, in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling hydrocarbons such as aromatics, saturated or unsaturated aliphatic hydrocarbons or alicyclic hydrocarbons, or mixtures of the organic solvents with the addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of substances which can be used as emulsifiers are: calcium (C6-Cps)-alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, (C2-C~a)-alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.
Dusts are generally obtained by grinding the active substance, for example the herbicidal active substance andlor the safener, with finely distributed solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspension concentrates can be water- or oil-based. They can be prepared, for example, by wet grinding using commercially available bead mills with or without an addition of surfactants, for example those which have already been mentioned above in the case of the other formulation types.
Emulsions, for example oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents in the presence or absence of surfactants which have already been mentioned above, for example, in the case of the other formulation types.
Granules can be prepared either by spraying the active substance, for example the herbicidal active substance and/or the safener, onto adsorptive, granulated inert material or by applying active substance concentrates to the surface of carriers such as sand, kaolinites or granulated inert material with the aid of binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active substances can also be granulated in the manner which is conventional for the preparation of fertilizer granules, if desired as a mixture with fertilizers.
As a rule, water-dispersible granules are prepared by the customary processes such as spray drying, fluidized bed granulation, disk granulation, mixing with high-speed mixers, and extrusion without solid inert material.
For the preparation of disk, fluidized-bed, extruder and spray granules see, for example, processes in "Spray-Drying Handbook" 3rd Ed. 1979, G.
Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 et seq.; "ferry's Chemical Engineer's Handbook", 5~' Ed., McGraw-Hill, New York 1973, p. 8-57.
For further details on the formulation of crop protection products see, for example, G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S.A. Evans, "Weed Control Handbook", 5~" Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
As a rule, the agrochemical formulations comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active substances, for example safener active substances (B), preferably of the formula (II) - (VII) and/or of group B (b), or herbicidal active substances of the formula (I), or of the herbicide/safener active substance mixture according to the invention comprising compounds of the formula (I) and safener active substances (B), preferably compounds of the formula (II) - (VII) and/or of group B (b), and 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid additive and 0 to 25% by weight, in particular 0.1 to 25%, by weight, of a surfactant.
In wettable powders, the active substance concentration is, for example, approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation components. In the case of emulsifiable concentrates, the concentration of active substance is approximately 1 to 80% by weight. Formulations in the form of dusts comprise 1 to 20% by weight of active substance, sprayable solutions comprise approximately 0.2 to 20% by weight of active substance. In the case of granules, such as water-dispersible granules, the active substance content depends partly on whether the active compound is in liquid or solid form. The active substance content of the water-dispersible granules is, for example, between 10 and 90% by weight.

Besides this the abovementioned formulations of active substances may comprise, if appropriate, the adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and pH and viscosity 10 regulators which are customary in each case.
Components which can be used in combination with the mixtures according to the invention in mixed formulations or in tank mixes are, for example, known active substances as they are described, for example, in Weed 15 Research 26, 441-445 (1986), or "The Pesticide Manual", 10'" edition, The British Crop Protection Council, 1994, and the literature cited therein.
Examples of active substances which may be mentioned as herbicides which are known from the literature and which can be combined with the mixtures according to the invention are the following (note: either the 20 common names in accordance with the International Organization for Standardization (ISO) or the chemical names, if appropriate together with a customary code number, of the compounds are given):
acetochlor; acifluorfen; aclonifen; AKH 7088, i.e. [[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]-25 acetic acid and its methyl ester; alachlor; alloxydim; ametryn;
amidosulfuron; amitrol; AMS, i.e. ammonium sulfamate; anilofos; asulam;
atrazine; azafenidine (DPX-R6447), azimsulfurone (DPX-A8947);
aziprotryn; barban; BAS 516 H, i.e. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; benazolin; benfluralin; benfuresate; bensulfuron-methyl; bensulide;
30 bentazone; benzofluor; benzoylprop-ethyl; benzthiazuron; bialaphos;
bifenox; bispyribac-sodium (KIH-2023), bromacil; bromobutide;
bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor;
butamifos; butenachlor; buthidazole; butralin; butroxydim (ICI-0500), butylate; cafenstrole (CH-900); carbetamide; cafentrazone; CDAA, i.e.
2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chloroallyl diethyldithio-carbamate; chlomethoxyfen; chloramben; chloransulam-methyl (XDE-565), chlorazifop-butyl, chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron ethyl; chlornitrofen; chlorotoluron;
chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid;

_ - 31 cinidon-ethyl, cinmethylin; cinosulfuron; clethodim; clodinafop and its ester derivatives (e.g. clodinafop-propargyl); clomazone; clomeprop;
cloproxydim; clopyralid; cumyluron (JC 940); cyanazine; cycloate;
cyclosulfamuron (AC 014); cycloxydim; cycluron; cyhalofop and its ester derivatives (e.g. butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; , 2,4-DB; dalapon; desmedipham; desmetryn; di-allate; dicamba; dichlobenil;
dichlorprop; diclofop and its esters such as diclofop-methyl; diclosulam (XDE-564), diethatyl; difenoxuron; difenzoquat; diflufenican; diflufenzopyr-sodium (SAN-835H), dimefuron; dimethachlor; dimethametryn;
dimethenamid (SAN-582H); dimethazone, 5-(4,6-dimethylpyrimidin-2-yl-carbamoylsulfamoyl)-1-(2-pyridyl)-pyrazole-4-carboxylate (NC-330);
triaziflam (IDH-1105), clomazon; dimethipin; dimetrasulfuron, dinitramine;
dinoseb; dinoterb; diphenamid; dipropetryn; diquat; dithiopyr; diuron;
DNOC; eglinazine-ethyl; EL 177, i.e. 5-cyano-1-(1,1-dimethylethyl)-N-methyl-1 H-pyrazole-4-carboxamide; endothal; epoprodan (MK-243), EPTC;
esprocarb; ethalfluralin; ethametsulfuron-methyl; ethidimuron; ethiozin;
ethofumesate; F5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-1 H-tetrazol-1-yl]phenyl]ethanesulfonamide; ethoxyfen and its esters (e.g. ethyl ester, HN-252); ethoxysulfuron (disclosed in EP 342569) etobenzanid (HW 52); 3-(4-ethoxy-6-ethyl-1,3,5-triazin-2-yl)-1-(2,3-dihydro-1,1-dioxo-2-methylbenzo[b]thiophene-7-sulfonyl)urea (EP-A 079 683); 3-(4-ethyl-6-methoxy-1,3,5-triazin-2-yl)-1-(2,3-dihydro-1,1-dioxo-2-methylbenzo[b]thiophene-7-sulfonyl)urea (EP-A 079 683); fenoprop;
fenoxan, fenoxaprop and fenoxaprop-P and their esters, e.g. fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim; fenuron; flamprop-methyl;
flazasulfuron; flufonacet (BAY-FOE-5043), fluazifop and fluazifop-P, florasulam (DE-570) and their esters, e.g. fluazifop-butyl and fluazifop-P-butyl; fluchloralin; flumetsulam; flumeturon; flumiclorac and their esters (e.g. pentyl ester, S-23031 ); flumioxazin (S-482); flumipropyn; flupoxam (KNW-739); fluorodifen; fluoroglycofen-ethyl; flupropacil (URIC-4243);
flupyrsulfuron-methyl sodium (DPX-KE459), fluridone; flurochloridone;
fluroxypyr; flurtamone; fluthiacet-methyl (KIH-9201 ), fomesafen; fosamine;
furyloxyfen; glufosinate; glyphosate; halosafen; halosulfuron and its esters (e.g. methyl ester, NC-319); haloxyfop and its esters; haloxyfop-P (= R-haloxyfop) and its esters; hexazinone; imazamethabenz-methyl; imazamox (AC-299263), imazapyr; imazaquin and salts such as the ammonium salt;
imazethamethapyr; imazethapyr; imazosulfuron; iodosulfuron (methyl-4-iodo-2-[3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureidosulfonyl]-benzoate, sodium salt, WO 92113845); ioxynil; isocarbamid; isopropalin; isoproturon;

isouron; isoxaben; isoxapyrifop; karbutilate; lactofen; lenacil; linuron;
MCPA; MCPB; mecoprop; mefenacet; mefluidid; metamitron; metazachlor;
methabenzthiazuron; metham; methazole; methoxyphenone;
methyldymron; metobenzuron, methyl-2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-methanesulfonamidomethylbenzoate (WO 95/10507);
methobenzuron; metobromuron; metolachlor; S-metolachlor, metosulam (XRD 511 ); metoxuron; metribuzin; metsulfuron-methyl; MH; molinate;
monalide; monocarbamide dihydrogensulfate; monolinuron; monuron;
MT 128, i.e. 6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinamine; MT 5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide; N,N-dimethyl-2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-formylaminobenzamide (WO 95/01344); naproanilide;
napropamide; naptalam; NC 310, i.e. 4-(2,4-dichlorobenzoyi)-1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitralin; nitrofen;
nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630);
oxadiazon; oxaziclomefone (MY-100), oxyfluorfen; oxasulfuron (CGA-277476), paraquat; pebulate; pendimethalin; pentoxazone (KPP-314), perfluidone; phenisopham; phenmedipham; picloram; piperophos;' piributicarb; pirifenop-butyl; pretilachlor; primisulfuron-methyl; procyazine;
prodiamine; profluralin; proglinazine-ethyl; prometon; prometryn;
propachlor; propanil; propaquizafop and its esters; propazine; propham;
propisochlor; propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor; , pyraflufen-ethyl (ET-751 ), pyrazon; pyrazosulfuron-ethyl; pyrazoxyfen; pyribenzoxim, pyridate; pyriminobac-methyl (KIH-6127), pyrithiobac (KIH-2031); pyroxofop and its esters (e.g. propargyl ester);
quinclorac; quinmerac; quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives e.g. quizalofop-ethyl; quizalofop-P-tefuryl and -ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, i.e. 2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4,5,6,7-tetrahydro-2H-indazole;
secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, i.e. 2-[[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthalenyl]oxy]-propanoic acid and its methyl ester; sulfentrazon (FMC-97285, F-6285); sulfazuron;
sulfometuron-methyl; sulfosate (ICI-A0224); sulfosulfuron (MON-37500), TCA; tebutam (GCP-5544); tebuthiuron; tepraloxidim (BAS-620H), terbacil;
terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutryn; TFH 450, i.e.
N,N-diethyl-3-[(2-ethyl-6-methylphenyl)sulfonyl]-1 H-1,2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiazafluron; thiazopyr (Mon-13200);
thidiazimin (SN-124085); thifensulfuron-methyl; thiobencarb; tiocarbazil;
tralkoxydim; tri-allate; triasulfuron, triazofenamide; tribenuron-methyl;

triclopyr; tridiphane; trietazine; trifluralin; triflusulfuron and esters (e.g.
methyl ester, DPX-66037); trimeturon; tsitodef; vemolate; WL 110547, i.e.
5-phenoxy-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole; UBH-509; D-489; LS
82-556; KPP-300; KPP-421, MT-146, NC-324; KH-218; DPX-N8189;
DOWCO-535; DK-8910; V-53482; PP-600; MBH-001.
For use, the formulations which are in commercially available form are, if desired, diluted in the 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 broadcasting and sprayable solutions are usually not diluted any further with other inert substances prior to use.
The necessary application rate of the herbicides of the formula (I) varies with the external conditions such as, inter alia, temperature, humidity and the nature of the herbicide used. It may be varied within wide limits, for example between 0.001 and 10.0 kg/ha or more of herbicide; it is preferably between 0.005 and 5 kg/ha.
The examples which follow are intended to illustrate the invention:
A. Formulation Examples a) A dust is obtained by mixing 10 parts by weight of a herbicidally active substance of the formula (I) or of a compound of the formula (II) - (VII) and/or from amongst group B (b) or of an active substance mixture of a herbicidal active substance of the formula (I) and a safener of the formula (II) - (VII) andlor from amongst group B (b) and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill.
b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a herbicidal active substance of the formula (I) or of a compound of the formula (II)-(VII) and/or from amongst group B (b) or of an active substance mixture of a herbicidal active substance of the formula (I) and a safener of the formula (II)-(VII) andlor from amongst group B(b), 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetter and dispersant and grinding the mixture in a pinned-disk mill.
c) A concentrate which is readily dispersible or suspendable in water is obtained by mixing 20 parts by weight of a herbicidal active substance of the formula (I) or of a compound of the formula (II) -(VII) and/or from amongst group B(b) or of an active substance mixture of a herbicidal active substance of the formula (I) and a safener of the formula (II) - (VII) and/or from amongst group B(b), 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, approx. 255 to above 277°C) and grinding the mixture in a ball mil to a fineness of below 5 microns.
d) An emulsifiable concentrate is obtained from 15 parts by weight of a herbicidal active substance of the formula (I) or of a compound of the formula (11) - (VII) and/or from amongst group B(b) or of an active substance mixture of a herbicidal active substance of the formula (I) and a safener of the formula (II) - (VII) and/or from amongst group B(b), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
e) Water-dispersible granules are obtained by mixing 75 parts by weight of a herbicidal active substance of the formula (I) or of a compound of the formula (II) - (VII) and/or from amongst group B(b) or of an active substance mixture of a herbicidal active substance of the formula (I) and a safener of the formula (II) - (VII) and/or from amongst group B(b), 10 " of calcium lignosulfonate 5 " of sodium lauryl sulfate, 3 " of polyvinyl alcohol and 7 " of kaolin, grinding the mixture on a pinned-disk mill and granulating the powder in a fluidized bed by spraying on water as the granulation liquid.

_ 35 f) Water-dispersible granules are also obtained by homogenizing and precomminuting, on a colloid mill, 25 parts) by weight of a herbicidal active substance of the formula (I) or of a compound of the formula (II) (VII) and/or from amongst group B(b) or of an active substance mixture of a herbicidal active substance of the formula (I) and a safener of the formula (II) - (VII) and/or from amongst group B(b) 5 " of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate 2 " of sodium oleoylmethyltaurinate, 1 " of polyvinyl alcohol, 17 " of calcium carbonate and 50 " of water, subsequently grinding the mixture on a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a single-substance nozzle.
Biological Examples 1. Scoring the damage The damage to the plants is assessed visually in comparison with control plants using a scale of 0 to 100%:
0% - no noticeable effect in comparison with the untreated plant, 100% - treated plant dies.
2. Post-emergence herbicide action Seeds of monocotyledonous and dicotyledonous weed plants and of crop plants are placed in sandy loam soil in plastic pots, covered with soil and grown in the greenhouse under good growth conditions.
Three weeks after sowing, the test plants are treated in the 3-4 - leaf stage.
The individual active substances according to the invention which are formulated as emulsion concentrates are sprayed, individually or as mixtures, onto the green parts of the plants in various dosages at a water application rate of 300 Uha (converted) and, after the test plants have been left in the greenhouse for three weeks under ideal growth conditions, the effect of the products is scored visually by comparison with untreated controls. The results are summarized in Table 1 below.
Table 1:
Active Dose WheatMaize AMARE VERPE VIOTR PHBPU XANOR
sub- g a.s./ha stances (I-1) 75 30 40 100 100 100 100 100 (I - 75+37.5 10 35 100 100 100 100 100 1 ) +

( I 19+9.5 5 20 100 100 100 100 98 I -1 ) (I - 75+75 25 25 - - - - -1 ) +

(II 19+19 15 10 100 100 100 100 95 - 9) Abbreviations: g a.s./ha g of active substance per hectare AMARE = Amarantus retroflexus VERPE = Veronica persica VIOTR = Viola Tricolor PHBPU = Pharbitis purpurea XANOR = Xanthium Orientate The terms (I-1 ), (II-1 ) and (II-9) are explained in the description.
As can be seen from the examples, the herbicide-safener combinations according to the invention are capable of controlling a broad spectrum of weeds in a sustained manner, while damage to crop plants as in comparison with the use of the individual herbicides without safener is substantially reduced.

Claims (9)

Claims:
1. A herbicidally active composition comprising a mixture of (A) a herbicidally active amount of one or more compounds of the formula (I) in which X and Y are identical or different and are hydrogen or halogen such as fluorine, chlorine, bromine or iodine, Z is -S-CHR1-COOR2 in which R1 is hydrogen or C1-C20-alkyl, preferably C1-C6-alkyl, R2 is C1-C20-alkyl, C3-C8-cycloalkyl or C1-C10-alkoxy-C1-C10-alkyl, preferably C1-C6-alkyl, C4-C6-cycloalkyl or C1-C4-alkoxy-C1-C4-alkyl, or is -COOR3 where R3 is C1-C20-alkyl, preferably C1-C6-alkyl, or Y and Z together form a group -O-CHR4-CO-NR5- which, together with the phenyl ring, forms a ring in which R4 is hydrogen or C1-C20-alkyl, preferably C1-C6-alkyl, and R5 is C1-C20-alkyl, C2-C20-alkenyl or C2-C20-alkynyl, preferably C1-C6-alkyl, C3-C5-alkenyl or C3-C5-alkynyl, and (B) an antidote-effective amount of one or more safeners.
2. A herbicidally active composition as claimed in claim 1, wherein the compound of the formula (I) has the formula (Ia) in which X is hydrogen or halogen, preferably fluorine, Y is halogen, preferably chlorine, and Z is as defined in formula (I) and is preferably -S-CH(CH3)-COOR2 or -S-CH2-COOR2 where R2 is C1-C6-alkyl or C4-C6-cycloalkyl.
3. A herbicidally active composition as claimed in claim 1 or 2, where the safener(s) (B) is selected from the group consisting of:
a) compounds of the formulae (II) to (IV), where the symbols and indices have the following meanings:
n' is a natural number from 0 to 5, preferably 0 to 3;
T is a (C1 or C2)-alkanediyl chain which is unsubstituted or substituted by one or two (C1-C4)alkyl radicals or by [(C1-C3)-alkoxy]carbonyl;
W is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the partially unsaturated or aromatic five-ringed heterocycles having 1 to 3 hetero ring atoms of the type N or O, the ring containing at least one nitrogen atom and not more than one oxygen atom preferably a radical selected from the group consisting of (W1) to (W4), m' is 0 or 1;
R17, R19 are identical or different halogen, (C1-C4)alkyl, (C1-C4)alkoxy, nitro or (C1-C4)haloalkyl;
R18, R20 are identical or different OR24, SR24 or NR24R25 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and up to 3 hetero atoms, preferably from the group consisting of O and S, which is linked to the carbonyl group in (II) or (III) via the nitrogen atom and which is unsubstituted or substituted by radicals from the group consisting of (C1-C4)alkyl, (C1-C4)alkoxy or optionally substituted phenyl, preferably a radical of the formula OR24, NHR25 or N(CH3)2, in particular of the formula OR24;
R24 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical preferably having in total 1 to 18 carbon atoms;
R25 is hydrogen, (C1-C6)alkyl, (C1-C6)alkoxy or substituted or unsubstituted phenyl;
R26 is hydrogen, (C1-C8)alkyl, (C1-C6)haloalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C6)hydroxyalkyl, (C3-C12)cycloalkyl or tri-(C1-C4)-alkylsilyl;
R27, R28, R29 are identical or different hydrogen, (C1-C8)alkyl, (C1-C8)haloalkyl, (C3-C12)cycloalkyl or substituted or unsubstituted phenyl;
R21 is (C1-C4)alkyl, (C1-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4) haloalkenyl, (C3-C7)cycloalkyl, preferably dichloromethyl;
R22, R23 is identical or different hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C1-C4)haloalkyl, (C2-C4)haloalkenyl, (C1-C4)alkylcarbamoyl-(C1-C4)alkyl, (C2-C4)alkenylcarbamoyl-(C1-C4)alkyl, (C1-C4)alkoxy-(C1-C4)alkyl, dioxolanyl-(C1-C4)alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R22 and R23 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring;
b) one or more compounds from the group consisting of:
1,8-naphthalic anhydride, methyl diphenylmethoxyacetate, cyanomethoxyimino(phenyl)acetonitrile (cyometrinil), 1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil), 4'-chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime (fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim), benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), N-(4-methylphenyl)-N'-(1-methyl-1-phenylethyl)urea (dymron), 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-naphthoylsulfamoyl)phenyl]-3,3-dimethylurea, (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor) and their salts and esters, preferably (C1-C8);
c) N-acylsulfonamides of the formula (V) and their salts, where R30 is hydrogen, a hydrocarbon radical, a hydrocarbonoxy radical, a hydrocarbonthio radical or a heterocyclyl radical which is preferably bonded via a carbon atom, each of the last-mentioned 4 radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, carboxamide, sulfonamide and radicals of the formula -Z a-R a, each hydrocarbon moiety preferably having 1 to 20 carbon atoms and a carbon-containing radical R30 inclusive of substituents preferably having 1 to 30 carbon atoms;
R31 is hydrogen or (C1-C4)alkyl, preferably hydrogen, or R30 and R31 together with the group of the formula -CO-N- are the radical of a 3- to 8-membered saturated or unsaturated ring;
R32 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, CONH2, SO2NH2 or a radical of the formula -Z b-R b;
R33 is hydrogen or (C1-C4)alkyl, preferably hydrogen;
R34 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH2, SO2NH2 or a radical of the formula -Z c-R c, R a is a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and di-[(C1-C4)alkyl]amino, or is an alkyl radical in which more than one, preferably 2 or 3, nonadjacent CH2 groups are each replaced by an oxygen atom;
R b, R c identical or different are a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halo(C1-C4)alkoxy, mono- and di[(C1-C4)alkyl]amino, or are an alkyl radical in which more than one, preferably 2 or 3, nonadjacent CH2 groups are each replaced by an oxygen atom;
Z a is a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO-, -S-CO-, -SO-, -SO2-, -NR*-, -CO-NR*-, -NR*-CO-, -SO2-NR*- or -NR*-SO2-, the bond shown on the right of the divalent group in question being the bond to the radical R a and the R* in the last-mentioned 5 radicals independently of one another being in each case H, (C1-C4)alkyl or halo(C1-C4)alkyl;
Z b,Z c independently of one another are a direct bond or a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO-, -S-CO-, -SO-, -SO2-, -NR*-, -SO2-NR*-, -NR*-SO2-, -CO-NR*- or -NR*-CO-, the bond shown on the right of the divalent group in question being the bond to the radical R b or R c, respectively, and the R* in the last-mentioned 5 radicals independently of one another being in each case H, (C1-C4)alkyl or halo(C1-C4)alkyl;
n is an integer from 0 to 4, preferably 0, 1 or 2, in particular 0 or 1, and m is an integer from 0 to 5, preferably 0, 1, 2 or 3, in particular 0, 1 or 2;
d) acylsulfamoylbenzamides of the formula (VI), if appropriate in salt form, where X3 is CH or N;
R35 is hydrogen, heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals optionally being substituted by one or more, identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH2, SO2NH2 and Z a-R a;

R36 is hydrogen, hydroxyl, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C2-C6)alkenyloxy, the five last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, hydroxyl, (C1-C4)alkyl, (C1-C4)alkoxy and (C1-C4)alkylthio, or R35 and R36 together with the nitrogen atom to which they are attached are a 3- to 8-membered saturated or unsaturated ring;
R37 is halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH2, SO2NH2 or Z b-R b;
R38 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl;

R39 is halogen, cyano, nitro, amino, hydroxyl, carboxyl, phosphoryl, CHO, CONH2, SO2NH2 or Z c -R c;
R a is a (C2-C20)alkyl radical whose carbon chain is interrupted once or more by oxygen atoms, or is heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals optionally being substituted by one or more, identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and di[(C1-C4)alkyl]amino;
R b, R c identical or different are a (C2-C20)alkyl radical whose carbon chain is interrupted once or more by oxygen atoms, or are heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, (C1-C4)haloalkoxy, mono- and di[(C1-C4)-alkyl]amino;
Z a is a divalent unit selected from the group consisting of O, S, CO, CS, C(O)O, C(O)S, SO, SO2, NR d, C(O)NR d or SO2NR d;
Z b, Z c identical or different are a direct bond or a divalent unit selected from the group consisting of O, S, CO, CS, C(O)O, C(O)S, SO, SO2, NR d, SO2NR d or C(O)NR d;
R d is hydrogen, (C1-C4)alkyl or (C1-C4)haloalkyl;
N is an integer from 0 to 4, and m, in the event that X is CH, is an integer from 0 to 5 and, in the event that X is N, an integer from 0 to 4;
e) compounds of the formula (VII), where the symbols and indices have the following meanings:
R40 is H, (C1-C4)alkyl, (C1-C4)alkyl substituted by (C1-C4)alkyl-X4 or (C1-C4)haloalkyl-X4, (C1-C4)haloalkyl, NO2, CN, -COO-R43, NR244, SO2NR2 45 or CONR2 46;

R41 is H, halogen, (C1-C4)alkyl, CF3, (C1-C4)alkoxy or (C1-C4)halo-alkoxy;
R42 is H, halogen or (C1-C4)alkyl;
Q1, Q2, E, G are identical or different, -O-, -S-, -CR247-, -CO-, NR48- or a group of the formula (VIII), with the proviso that a) at least one of the groups Q1, Q2, E, G is a carbonyl group, that exactly one of this group is a radical of the formula (VIII) and that the group of the formula (VIII) is adjacent to a carbonyl group, and two adjacent groups Q1, Q2, E and G cannot simultaneously be oxygen;
R a is identical or different H or (C1-C6)alkyl or the two radicals R a together are (C2-C6)alkylene;
A is R b -Y3- or -NR2 49;
X4 is -O- or -S(O)p-;
Y3 is -O- or -S-;
R b is H, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C4)alkoxy(C1-C8)alkyl, (C3-C6)alkenyloxy(C1-C8)alkyl, or phenyl(C1-C8)alkyl, the phenyl ring optionally being substituted by halogen, (C1-C4)alkyl, CF3, methoxy or methyl-S(O)p; (C3-C6)alkenyl, (C3-C6)haloalkenyl, phenyl(C3-C6)alkenyl, (C3-C6)alkynyl, phenyl(C3-C6)alkynyl, oxetanyl, furfuryl, tetrahydrofuryl;
R43 is H or (C1-C4)alkyl;
R44 is identical or different H, (C1-C4)alkyl, (C1-C4)alkylcarbonyl or the two radicals R44 together are (C4-C5)alkylene;
R45, R46 are independently of one another in each case identical or different H, (C1-C4)alkyl, or the two radicals R45 and/or R46 together are (C4-C5)alkylene, it being possible for one CH2 group to be replaced by O or S or for one or two CH2 groups to be replaced by -NR c-;
R c is H or (C1-C8)alkyl;
R47 is identical or different H, (C1-C8)alkyl or the two radicals R47 together are (C2-C6)alkylene;

R48 is H, (C1-C8)alkyl, substituted or unsubstituted phenyl, or benzyl which is unsubstituted or substituted on the phenyl ring;
R49 is identical or different H, (C1-C8)alkyl, phenyl, phenyl(C1-C8)alkyl, it being possible for a phenyl ring to be substituted by F, Cl, Br, NO2, CN, OCH3, (C1-C4)alkyl or CH3SO2-; or is (C1-C4)alkoxy-(C1-C8)alkyl, (C3-C6)alkenyl, (C3-C6)alkynyl, (C3-C6)cycloalkyl or two radicals R49 together are (C4-C5)alkylene, it being possible for one CH2 group to be replaced by O or S or for one or two CH2 groups to be replaced by -NR d-;
R d is H or (C1-C4)alkyl;
m" is 0 or 1 and p is 0, 1 or 2;
inclusive of the stereoisomers and of the salts conventionally used in agriculture.
4. A herbicidally active composition as claimed in one or more of claims 1 to 3, in which the weight ratio herbicide:safener is 1:100 to 100:1.
5. A herbicidally active composition as claimed in one or more of claims 1 to 4, additionally comprising one or more further agrochemical active substances.
6. A method of controlling harmful plants in plant crops, which comprises applying a herbicidally effective amount of a herbicidally active composition as claimed in one or more of claims 1 to 5 to the harmful plants, the crop plants, the seeds of the plants or the area on which the plants grow.
7. The method as claimed in claim 6, wherein the crop plants are selected from the group consisting of maize, wheat, rye, barley, oats, rice, sorghum, cotton and soya.
8. The method as claimed in claim 6 or 7, wherein the crop plants are transgenic or display tolerance as a result of selection-based breeding.
9. The use of a herbicidally active composition as claimed in one or more of claims 1 to 5 for controlling harmful plants in plant crops.
CA002378857A 1999-08-03 2000-07-22 Combinations of herbicides and safeners Abandoned CA2378857A1 (en)

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