US20200085058A1

US20200085058A1 - Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners

Info

Publication number: US20200085058A1
Application number: US16/690,200
Authority: US
Inventors: Dieter Feucht; Peter Dahmen; Mark Wilhelm Drewes; Rolf Pontzen; Ernst Rudolf F. Gesing; Hans-Georg Schwarz; Klaus-Helmur Mueller
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2001-09-21
Filing date: 2019-11-21
Publication date: 2020-03-19
Also published as: FR17C1034I2; HUP0402116A3; US20050009705A1; NL350078I1; JP2005503421A; EP1429613B1; FR17C1034I1; CA2460922C; US9968091B2; NL350082I2; HU230218B1; US10524475B2; US20130237418A1; PT1429613E; RU2004112214A; RS24504A; HUS000505I2; KR100979997B1; HRP20040359B1; EP1429613A1

Abstract

The invention relates to selective herbicidal compositions that comprise an effective amount of an active compound combination comprising

(a) one or more compounds of the formula (I)

in which Q¹, Q², R¹, R², R³and R⁴are as defined in the disclosure—and salts of the compounds of the formula (I)—
and
(b) at least one of the crop-plant-compatibility-improving compounds listed in the disclosure.

The invention further relates to the use of these compositions for controlling undesirable vegetation and to a process for preparing the compositions according to the invention.

Description

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a Continuation of U.S. application Ser. No. 14/950,588, filed Nov. 24, 2015, which is a Continuation of U.S. application Ser. No. 13/873,656, filed Apr. 30, 2013, now U.S. Pat. No. 9,968,091, issued May 15, 2018, which in turn is a Continuation of U.S. application Ser. No. 10/489,092, filed Sep. 7, 2004, which is a § 371 National Stage Application of PCT/EP2002/010104, filed Sep. 10, 2002, which claims priority to German Application No. 101 46 590.4, filed Sep. 21, 2001, the contents all of which are incorporated herein by reference in their entireties.

BACKGROUND

Field of the Invention

The invention relates to novel selective herbicidal active compound combinations which comprise substituted thien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones and at least one compound which improves crop plant compatibility and which can be used with particularly good results for the selective control of weeds in various crops of useful plants.

Description of Related Art

Substituted thien-3-ylsulphonylamino(thio)carbonyltriazoline(ethi)ones are already known as effective herbicides (cf WO-A-01/05788). However, the activity of these compounds and/or their compatibility with crop plants are not entirely satisfactory under all conditions.

SUMMARY

Surprisingly, it has now been found that certain substituted thien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones, when used together with the crop-plant-compatibility-improving compounds (safeners/antidotes) described below, prevent damage to crop plants extremely well and can be used particularly advantageously as broad-spectrum combination preparations for the selective control of weeds in crops of useful plants, such as, for example, in cereals and maize.
The invention provides selective herbicidal compositions, characterized by an effective amount of an active compound combination comprising

- (a) substituted thien-3-yl sulphonylamino(thio)carbonyltriazolin(ethi)ones of the formula (I)

- in which
- Q¹represents O (oxygen) or S (sulphur),
- Q²represents O (oxygen) or S (sulphur),
- R¹represents optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally cyano- or halogen-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case optionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, represents in each case optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted heterocyclyl or heterocyclylalkyl having in each case up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and/or 1 or 2 oxygen or sulphur atoms in the heterocyclyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,
- R²represents hydrogen, cyano, nitro, halogen, represents in each case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl group, or represents in each case optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkynyl group,
- R³represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, represents optionally fluorine-, chlorine-, bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substituted alkoxy, alkylthio, alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, represents alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino or alkynylamino having in each case 3 to 6 carbon atoms in the alkenyl or alkynyl group, represents dialkylamino haying in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino and/or morpholino, represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C₁-C₄-alkyl-substituted cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-, trifluoromethyl-, C₁-C₄-alkoxy- and/or C₁-C₄-alkoxy-carbonyl-substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino of arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,
- R⁴represents hydrogen, hydroxyl, amino, cyano, represents C₂-C₁₀-alkylideneamino, represents optionally fluorine-, chlorine-, bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, C₁-C₄-alkoxy- or C₁-C₄-alkoxy-carbonyl-substituted alkoxy, alkylamino or alkyl-carbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, represents alkenyloxy having 3 to 6 carbon atoms, represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C₁-C₄-alkyl-substituted cycloalkyl, cycloalkylamino or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano- nitro-, C₁-C₄-alkyl-, trifluoromethyl- and/or C₁-C₄-alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or
- R³and R⁴together represent optionally branched alkanediyl having 3 to 6 carbon atoms,
- and salts of the compounds of the formula (1)—
- (“active compounds of group 1”)
- and
- (b) at least one compound which improves crop plant compatibility, from the group of compounds below:
  4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane (AD-67, MON-4660), 1-dichloro-acetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-one (dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1-methyl-hexyl 5-chloro-quinolin-8-oxy-acetate (cloquintocet-mexyl—cf. also related compounds in EP-A-86750, EP-A-94349, EP-A-191736, EP-A-492366), 3-(2-chloro-benzyl)-1-(1-methyl-1-phenyl-ethyl)-urea (cumyluron), α-(cyanomethoximino)-phenylacetonitrile (cyometrinil), 2,4-dichloro-phenoxyacetic acid (2,4-D), 4-(2,4-dichloro-phenoxy)-butyric acid (2,4-DB), 1-(1-methyl-1-phenyl-ethyl)-3-(4-methyl-phenyl)-urea (daimuron, dymron), 3,6-dichloro-2-methoxy-benzoic acid (dicamba), S-1-methyl-1-phenyl-ethyl piperidine-1-thiocarboxylate (dimepiperate), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide (DKA-24), 2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), ethyl 1-(2,4-dichloro-phenyl)-5-trichloro-methyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl—cf. also related compounds in EP-A-174562 and EP-A-346620), phenyl-methyl 2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-α-trifluoro-acetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine (furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl—cf. also related compounds in WO-A-95/07897), 1-(ethoxycarbonyl)-ethyl-3,6-dichloro-2-methoxybenzoate (lactidichlor), (4-chloro-o-tolyloxy)-acetic acid (MCPA), 2-(4-chloro-o-tolyloxy)-propionic acid (mecoprop), diethyl 1-(2,4-dichloro-phenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl—cf. also related compounds in WO-A-91/07874), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro[4.5]decane 4-carbodithioate (MG-838), 1,8-naphthalic anhydride, α-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), 4-(4-chloro-o-tolyl)-butyric acid, 4-(4-chloro-phenoxy)-butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate (MON-7400, cf. U.S. Pat. No. 4,964,893), ethyl diphenylmethoxyacetate, methyl 1-(2-chloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-(1,1-dimethyl-ethyl)-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate (cf. also related compounds in EP-A-269806 and EP-A-333131), ethyl 5-(2,4-dichloro-benzyl)-2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5-(4-fluoro-phenyl)-5-phenyl-2-isoxazoline-3-carboxylate (cf. also related compounds in WO-A-91/08202), 1,3-dimethyl-but-1-yl 5-chloro-quinolin-8-oxy-acetate, 4-allyloxy-butyl 5-chloro-quinolin-8-oxy-acetate, 1-allyloxy-prop-2-yl 5-chloro-quinolin-8-oxy-acetate, methyl 5-chloro-quinolin-8-oxy-acetate, ethyl 5-chloro-quinolin-8-oxy-acetate, allyl 5-chloro-quinolin-8-oxy-acetate, 2-oxo-prop-1-yl 5-chloro-quinolin-8-oxy-acetate, diethyl 5-chloro-quinolin-8-oxy-malonate, diallyl 5-chloro-quinolin-8-oxy-malonate, diethyl 5-chloro-quinolin-8-oxy-malonate (cf. also related compounds in EP-A-582198), 4-carboxy-chroman-4-yl-acetic acid (AC-304415, cf. EP-A-613618), 4-chloro-phenoxyacetic acid, 3,3′-dimethyl-4-methoxy-benzophenone, 1-bromo-4-chloromethylsulphonyl-benzene, 1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3-methyl-urea (alias N-(2-methoxy-benzoyl)-4-[(methylamino-carbonyl)-amino]-benzenesulphonamide), 1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3,3-dimethyl-urea, 1-[4-(N-4,5-dimethylbenzoylsulphamoyl)-phenyl]-3-methyl-urea, 1-[4-(N-naphthylsulphamoyl)-phenyl]-3,3-dimethyl-urea, N-(2-methoxy-5-methyl-benzoyl)-4-(cyclopropyl-aminocarbonyl)-benzenesulphonamide,
- and/or the following compounds
- of the formula (IIa)

or the formula (IIb)
or the formula (IIc)
where

- n represents a number between 0 and 5,
- A¹represents one of the divalent heterocyclic groupings shown below,

- A²represents optionally C₁-C₄-alkyl- and/or C₁-C₄-alkoxy-carbonyl-substituted alkanediyl having 1 or 2 carbon atoms,
- R⁵represents hydroxyl, mercapto, amino, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or di-(C₁-C₄-alkyl)-amino,
- R⁶represents hydroxyl, mercapto, amino, in each case optionally C₁-C₄-alkyl, C₁-C₄-alkoxy or C₂-C₄-alkenoxy-substituted C₁-C₆-alkoxy, C₂-C₆-alkenoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or di-(C₁-C₄-alkyl)-amino,
- R⁷represents in each case optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₄-alkyl,
- R⁸represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine- and/or bromine- or C₁-C₄-alkyl-substituted phenyl,
- R⁹represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine- and/or bromine- or C₁-C₄-alkyl-substituted phenyl, or together with R⁸represents C₃-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, each of which is optionally substituted by C₁-C₄-alkyl, phenyl, furyl, a fused-on benzene ring or by two substituents which together with the C atom to which they are attached form a 5- or 6-membered carbocycle,
- R¹⁰represents hydrogen, cyano, halogen, or represents in each case optionally fluorine, chlorine- and/or bromine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl,
- R¹¹represents hydrogen, optionally hydroxyl-, cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl or tri-(C₁-C₄-alkyl)-silyl,
- R¹²represents hydrogen, cyano, halogen, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl,
- X¹represents nitro, cyano, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,
- X²represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,
- X³represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,
- where X¹is preferably found at the (2) and (4) positions, X²is preferably found at the (5) position and X³is found at the (2) position.
  and/or the following compounds
  of the formula (IId)

or the formula (IIe)
where

- n again represents a number between 0 and 5,
- R¹³represents hydrogen or C₁-C₄-alkyl,
- R¹⁴represents hydrogen or C₁-C₄-alkyl,
- R¹⁵represents hydrogen, in each case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or di-(C₁-C₄-alkyl)-amino, or in each case optionally cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio or C₃-C₆-cycloalkylamino,
- R¹⁶represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each ease optionally cyano- or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, or optionally cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,
- R¹⁷represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano- or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, or optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substituted phenyl, or together with R¹⁶represents in each case optionally C₁-C₄-alkyl-substituted C₂-C₆-alkanediyl or C₂-C₅-oxaalkanediyl.
- X⁴represents nitro, cyano, carboxyl, carbamoyl, fonnyl, sulphamoyl, hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy. and
- X⁵represents nitro, cyano, carboxyl. carbamoyl. fonnyl, sulphamoyl, hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,
- where X4 is preferably located in position (2) and/or (5) (“active compounds of group 2”).

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

In the definitions, the hydrocarbon chains, such as in alkyl or alkanediyl, are in each case straight-chain or branched—including in combination with hetero atoms, such as in alkoxy.
Preferred meanings of the groups listed above in connection with the formula (I) are defined below.

- Q¹preferably represents O (oxygen) or S (sulphur).
- Q²preferably represents O (oxygen) or S (sulphur).
- R¹preferably represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or tbutyl, represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propynyl or butynyl, represents in each case optionally cyano-, fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoro-methoxy- or trifluoromethoxy-substituted phenyl, phenylmethyl or phenyl-ethyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted heterocyclyl or heterocyclylmethyl, where the heterocyclyl group is in each case selected from the group consisting of oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl.
- R²represents hydrogen, cyano, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, or represents in each case optionally cyano-, fluorine- or chlorine-substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy.
- R³represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i, s- or t-butyl, represents in each case optionally fluorine-, chlorine- and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, acetylamino or propionylamino, represents propenyloxy, butenyloxy, ethynyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynythio, butynylthio, propenylamino, butenylamino, propynylamino or butynylamino, represents dimethylamino, diethylamino or dipropylamino, represents in each case optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cydobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluorine-, chlorine-, bromine-, methyl-, trifluoromethyl-, methoxy- or methoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino.
- R⁴preferably represents hydrogen, hydroxyl, amino, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine, chlorine, and/or bromine-substituted ethenyl, propenyl, butenyl, propynyl or butynyl, represents in each case optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, represents propenyloxy or butenyloxy, represents dimethylamino or diethylamino, represents in each case optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each case optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl.
- R³and R⁴together preferably represent trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl) or pentamethylene (pentane-1,5-diyl).
- Q¹particularly preferably represents O (oxygen).
- Q²particularly preferably represents O (oxygen).
- R¹particularly preferably represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl.
- R²particularly preferably represents fluorine, chlorine, bromine or represents in each case optionally fluorine-, chlorine-, methoxy- or, ethoxy-substituted methyl, ethyl, n- or i-propyl.
- R³particularly preferably represents hydrogen, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, represents in each case optionally fluorine- or chlorine-substituted ethenyl, propenyl, butenyl, propynyl or butynyl, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, represents propenyloxy, propynyloxy, propenylthio, propynylthio, propenylamino or propynylamino, represents dimethylamino or diethylamino, represents in each case optionally fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclopropyloxy, cyclopropylmethyl or cyclopropylmethoxy.
- R⁴particularly preferably represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, represents in each case optionally fluorine- or chlorine-substituted ethenyl, propenyl or propynyl, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, represents methylamino, or represents cyclopropyl.

Most preferably, R¹and R²represent methyl, ethyl, n- or i-propyl.
Preferred active compound components of group 1 are in particular also the sodium, potassium, magnesium, calcium, ammonium, C₁-C₄-alkylammonium-, di-(C₁-C₄-alkyl)ammonium-, tri-(C₁-C₄-alkyl)ammonium, tetra(C₁-C₄-alky)ammonium, tri-(C₁-C₄-alkyl)sulphonium-, C₅- or C₆-cycloalkylammonium and di-(C₁-C₂-alkyl)-benzylammonium salts of compounds of the formula (I) in which Q¹, Q², R¹, R², R³and R⁴have the meanings given above as being preferred.
Examples of compounds of the formula (I) which are very particularly preferred as active compound components according to the invention are listed in Table 1 below.

TABLE 1

Examples of compounds of the formula (I)

Ex.							Melting
No.	Q¹	Q²	R¹	R²	R³	R⁴	point (° C.)

I-1	O	O	CH₃	CH₃	OC₂H₅	CH₃	163
I-2	O	O	CH₃	CH₃	OCH₃	CH₃	201
I-3	O	O	CH₃	CH₃	OC₃H₇-n	CH₃	156
I-4	O	O	CH₃	CH₃	OC₃H₇-i	CH₃	150

I-5	O	O	CH₃	CH₃	OCH₃		218

I-6	O	O	CH₃	CH₃	OC₂H₅		170

I-7	O	O	CH₃	CH₃	OC₃H₇-n		156

I-8	O	O	CH₃	CH₃	OC₃H₇-i		188

I-9	O	O	CH₃	CH₃			200

I-10	O	O	CH₃	CH₃	CH₃	CH₃	178
I-11	O	O	CH₃	CH₃	CH₂H₅	CH₃	161
I-12	O	O	CH₃	CH₃	SCH₃	CH₃	183
I-13	O	O	CH₂H₅	CH₃	OCH₃	CH₃	176

I-14	O	O	CH₃	CH₃	CH₂OCH₃		185

I-15	O	O	CH₂H₅	CH₃	OC₂H₅	CH₃	172

I-16	O	O	CH₂H₅	CH₃	OCH₃		173

I-17	O	O	CH₃	CH₃	C₂H₅	OC₂H₅	183

I-18	O	O	CH₃	CH₃	C₂H₅		175

Very particular emphasis as active compound components according to the invention is also given to the sodium salts of the compounds from Table 1.
Preferred meanings of the groups listed above in connection with the compounds improving crop plant compatibility (“herbicide safeners”) of the formulae (IIa), (IIb), (IIc), (IId) and (IIe) are defined below.

- n preferably represents the numbers 0, 1, 2, 3 or 4.
- A²preferably represents in each case optionally methyl-, ethyl-, methoxycarbonyl- or ethoxycarbonyl-substituted methylene or ethylene.
- R⁵preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
- R⁶preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, or s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
- R⁷preferably represents in each case optionally fluorine-, chlorine- and/or bromine-substituted methyl, ethyl, n- or i-propyl.
- R⁸preferably represents hydrogen, in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl.
- R⁹preferably represents hydrogen, in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl, or together with R⁸represents one of the radicals —CH₂—O—CH₂—CH₂— and —CH₂—CH₂—O—CH₂—CH₂—, which are optionally substituted by methyl, ethyl, furyl, phenyl, a fused-on benzene ring or by two substituents which together with the C atom to which they are attached form a 5- or 6-membered carbocycle.
- R¹⁰preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.
- R¹¹preferably represents hydrogen, optionally hydroxyl-, cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
- R¹²preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.
- X¹preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
- X²preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
- X³preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
- R¹³preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
- R¹⁴preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
- R¹⁵preferably represents hydrogen, in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino.
- R¹⁶preferably represents hydrogen, in each case optionally cyano-, hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propynyl or butynyl, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
- R¹⁷preferably represents hydrogen, represents in each case optionally cyano-, hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted propertyl, butenyl, propynyl or butynyl, in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, or together with R¹⁶represents in each case optionally methyl- or ethyl-substituted butane-1,4-diyl (trimethylene), pentane-1,5-diyl, 1-oxa-butane-1,4-diyl or 3-oxa-pentane-1,5-diyl.
- X⁴preferably represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
- X⁵preferably represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.

Examples of compounds of the formula (IIa) which are very particularly preferred as herbicide safeners according to the invention are listed in Table 2 below.

TABLE 2

Examples of compounds of the formula (IIa)

	(IIa)

Exam-
ple	(positions)
No.	(X¹)_n	A¹	R⁵

IIa-1	(2) Cl, (4) Cl		OCH₃

IIa-2	(2) Cl, (4) Cl		OCH₃

IIa-3	(2) Cl, (4) Cl		OC₂H₅

IIa-4	(2) Cl, (4) Cl		OC₂H₅

IIa-5	(2) Cl		OCH₃

IIa-6	(2) Cl, (4) Cl		OCH₃

IIa-7	(2) F		OCH₃

IIa-8	(2) F		OCH₃

IIa-9	(2) Cl, (4) Cl		OC₂H₅

IIa-10	(2) Cl, (4) CF₃		OCH₃

IIa-11	(2) Cl		OCH₃

IIa-12	—		OC₂H₅

IIa-13	(2) Cl, (4) Cl		OC₂H₅

IIa-14	(2) Cl, (4) Cl		OC₂H₅

IIa-15	(2) Cl, (4) Cl		OC₂H₅

IIa-16	(2) Cl, (4) Cl		OC₂H₅

IIa-17	(2) Cl, (4) Cl		OC₂H₅

Examples of compounds of the formula (IIb) which are very particularly preferred as herbicide safeners according to the invention are listed in Table 3 below.

TABLE 3

Examples of compounds of the formula (IIb)

Ex-
am-	(posi-	(posi-
ple	tion)	tion)
No.	X²	X³	A²	R⁶

IIb-1	(5) Cl	—	CH₂	OH
IIb-2	(5) Cl	—	CH₂	OCH₃
IIb-3	(5) Cl	—	CH₂	OC₂H₅
IIb-4	(5) Cl	—	CH₂	OC₃H₇-n
IIb-5	(5) Cl	—	CH₂	OC₃H₇-i
IIb-6	(5) Cl	—	CH₂	OC₄H₉-n
IIb-7	(5) Cl	—	CH₂	OCH(CH₃)C₅H₁₁-n
IIb-8	(5) Cl	(2) F	CH₂	OH
IIb-9	(5) Cl	(2) Cl	CH₂	OH
IIb-10	(5) Cl	—	CH₂	OCH₂CH═CH₂
IIb-11	(5) Cl	—	CH₂	OC₄H₉-i

IIb-12	(5) Cl	—	CH₂

IIb-13	(5) Cl	—		OCH₂CH═CH₂

IIb-14	(5) Cl	—		OC₂H₅

Examples of the compounds (IIc) which are very particularly preferred as herbicide safeners according to the invention are listed in Table 4 below.

TABLE 4

Examples of compounds of the formula (IIc)

Example
No.	R⁷	N(R⁸, R⁹)

IIc-1	CHCl₂	N(CH₂CH═CH₂)₂

IIc-2	CHCl₂

IIc-3	CHCl₂

IIc-4	CHCl₂

IIc-5	CHCl₂

IIc-6	CHCl₂

IIc-7	CHCl₂

Examples of the compounds of the formula (IId) which are very particularly preferred as herbicide safeners according to the invention are listed in Table 5 below.

TABLE 5

Examples of compounds of the formula (IId)

Example				(positions)	(positions)
No.	R¹³	R¹⁴	R¹⁵	(X⁴)_n	(X⁵)_n

IId-1	H	H	CH₃	(2) OCH₃	—
IId-2	H	H	C₂H₅	(2) OCH₃	—
IId-3	H	H	C₃H₇-n	(2) OCH₃	—
IId-4	H	H	C₃H₇-i	(2) OCH₃	—

IId-5	H	H		(2) OCH₃	—

IId-6	H	H	CH₃	(2) OCH₃	—
				(5) CH₃
IId-7	H	H	C₂H₅	(2) OCH₃	—
				(5) CH₃
IId-8	H	H	C₃H₇-n	(2) OCH₃	—
				(5) CH₃
IId-9	H	H	C₃H₇-i	(2) OCH₃	—
				(5) CH₃

IId-10	H	H		(2) OCH₃ (5) CH₃	—

IId-11	H	H	OCH₃	(2) OCH₃	—
				(5) CH₃
IId-12	H	H	OC₂H₅	(2) OCH₃	—
				(5) CH₃
IId-13	H	H	OC₃H₇-i	(2) OCH₃	—
				(5) CH₃
IId-14	H	H	SCH₃	(2) OCH₃	—
				(5) CH₃
IId-15	H	H	SC₂H₅	(2) OCH₃	—
				(5) CH₃
IId-16	H	H	SC₃H₇-i	(2) OCH₃	—
				(5) CH₃
IId-17	H	H	NHCH₃	(2) OCH₃	—
				(5) CH₃
IId-18	H	H	NHC₂H₅	(2) OCH₃	—
				(5) CH₃
IId-19	H	H	NHC₃H₇-i	(2) OCH₃	—
				(5) CH₃

IId-20	H	H		(2) OCH₃ (5) CH₃	—

IId-21	H	H	NHCH₃	(2) OCH₃	—
IId-22	H	H	NHC₃H₇-i	(2) OCH₃	—
IId-23	H	H	N(CH₃)₂	(2) OCH₃	—
IId-24	H	H	N(CH₃)₂	(3) CH₃	—
				(4) CH₃
IId-25	H	H	CH₂OCH₃	(2) OCH₃	—
IId-26	H	H	CH₂OCH₃	(2) OCH₃	—
				(5) CH₃

Examples of the compounds of the formula (IIe) which are very particularly preferred as herbicide safeners according to the invention are listed in Table 6 below.

TABLE 6

Examples of compounds of the formula (IIe)

Example				(positions)	(positions)
No.	R¹³	R¹⁶	R¹⁷	(X⁴)_n	(X⁵)_n

IIe-1	H	H	CH₃	(2) OCH₃	—
IIe-2	H	H	C₂H₅	(2) OCH₃	—
IIe-3	H	H	C₃H₇-n	(2) OCH₃	—
IIe-4	H	H	C₃H₇-i	(2) OCH₃	—

IIe-5	H	H		(2) OCH₃	—

IIe-6	H	CH₃	CH₃	(2) OCH₃	—
IIe-7	H	H	CH₃	(2) OCH₃	—
				(5) CH₃
IIe-8	H	H	C₂H₅	(2) OCH₃	—
				(5) CH₃
IIe-9	H	H	C₃H₇-n	(2) OCH₃	—
				(5) CH₃
IIe-10	H	H	C₃H₇-i	(2) OCH₃	—
				(5) CH₃

IIe-11	H	H		(2) OCH₃ (5) CH₃	—

IIe-12	H	CH₃	CH₃	(2) OCH₃	—
				(5) CH₃
IIe-13	H	H	CH₂CH═CH₂	(2) OCH₃	—
IIe-14	H	H	CH₂CH═CH₂	(2) OCH₃	—
				(5) CH₃

IIe-15	H	H		(2) OCH₃	—

IIe-16	H	H		(2) OCH₃ (5) CH₃	—

IIe-17	H	H		(2) OCH₃	—

IIe-18	H	H		(2) OCH₃ (5) CH₃	—

IIe-19	H	H		(2) OCH₃	—

IIe-20	H	H		(2) OCH₃ (5) CH₃	—

The compounds of the general formula (IIa) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. WO-A-91/07874, WO-A-95/07897).
The compounds of the general formula (IIb) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. EP-A-191736).
The compounds of the general formula (IIe) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. DE-A-22180974, DE-A-2350547).
The compounds of the general formula (IId) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. DE-A-196215221/U.S. Pat. No. 6,235,680/WO 97/45016).
The compounds of the general formula (IIe) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. WO-A-99/66795/U.S. Pat. No. 6,251,827).
Examples of the selectively herbicidal combinations according to the invention of in each case one active compound of the formula (I) and in each case one of the safeners defined above are listed in Table 7 below.

TABLE 7

Examples of combinations according to the invention

	Active compound of the formula (I)	Safener

	I-1	AD-67
	I-1	cloquintocet-mexyl
	I-1	dichlormid
	I-1	fenchlorazole-ethyl
	I-1	isoxadifen-ethyl
	I-1	mefenpyr-diethyl
	I-1	MON-7400
	I-1	flurazole
	I-1	furilazole
	I-1	fenclorim
	I-1	cumyluron
	I-1	daimuron/dymron
	I-1	dimepiperate
	I-1	IId-25
	I-1	IIe-11
	I-2	AD-67
	I-2	cloquintocet-mexyl
	I-2	dichlormid
	I-2	fenchlorazole-ethyl
	I-2	isoxadifen-ethyl
	I-2	mefenpyr-diethyl
	I-2	MON-7400
	I-2	flurazole
	I-2	furilazole
	I-2	fenclorim
	I-2	cumyluron
	I-2	daimuron/dymron
	I-2	dimepiperate
	I-2	IId-25
	I-2	IIe-11
	I-3	AD-67
	I-3	cloquintocet-mexyl
	I-3	dichlormid
	I-3	fenchlorazole-ethyl
	I-3	isoxadifen-ethyl
	I-3	mefenpyr-diethyl
	I-3	MON-7400
	I-3	flurazole
	I-3	furilazole
	I-3	fenclorim
	I-3	cumyluron
	I-3	daimuron/dymron
	I-3	dimepiperate
	I-3	IId-25
	I-3	IIe-11
	I-4	AD-67
	I-4	cloquintocet-mexyl
	I-4	dichlormid
	I-4	fenchlorazole-ethyl
	I-4	isoxadifen-ethyl
	I-4	mefenpyr-diethyl
	I-4	MON-7400
	I-4	flurazole
	I-4	furilazole
	I-4	fenclorim
	I-4	cumyluron
	I-4	daimuron/dymron
	I-4	dimepiperate
	I-4	IId-25
	I-4	IIe-11
	I-5	AD-67
	I-5	cloquintocet-mexyl
	I-5	dichlormid
	I-5	fenchlorazole-ethyl
	I-5	isoxadifen-ethyl
	I-5	mefenpyr-diethyl
	I-5	MON-7400
	I-5	flurazole
	I-5	furilazole
	I-5	fenclorim
	I-5	cumyluron
	I-5	daimuron/dymron
	I-5	dimepiperate
	I-5	IId-25
	I-5	IIe-11
	I-6	AD-67
	I-6	cloquintocet-mexyl
	I-6	dichlormid
	I-6	fenchlorazole-ethyl
	I-6	isoxadifen-ethyl
	I-6	mefenpyr-diethyl
	I-6	MON-7400
	I-6	flurazole
	I-6	furilazole
	I-6	fenclorim
	I-6	cumyluron
	I-6	daimuron/dymron
	I-6	dimepiperate
	I-6	IId-25
	I-6	IIe-11
	I-7	AD-67
	I-7	cloquintocet-mexyl
	I-7	dichlormid
	I-7	fenchlorazole-ethyl
	I-7	isoxadifen-ethyl
	I-7	mefenpyr-diethyl
	I-7	MON-7400
	I-7	flurazole
	I-7	furilazole
	I-7	fenclorim
	I-7	cumyluron
	I-7	daimuron/dymron
	I-7	dimepiperate
	I-7	IId-25
	I-7	IIe-11
	I-8	AD-67
	I-8	cloquintocet-mexyl
	I-8	dichlormid
	I-8	fenchlorazole-ethyl
	I-8	isoxadifen-ethyl
	I-8	mefenpyr-diethyl
	I-8	MON-7400
	I-8	flurazole
	I-8	furilazole
	I-8	fenclorim
	I-8	cumyluron
	I-8	daimuron/dymron
	I-8	dimepiperate
	I-8	IId-25
	I-8	IIe-11
	I-9	AD-67
	I-9	cloquintocet-mexyl
	I-9	dichlormid
	I-9	fenchlorazole-ethyl
	I-9	isoxadifen-ethyl
	I-9	mefenpyr-diethyl
	I-9	MON-7400
	I-9	flurazole
	I-9	furilazole
	I-9	fenclorim
	I-9	cumyluron
	I-9	daimuron/dymron
	I-9	dimepiperate
	I-9	IId-25
	I-9	IIe-11
	I-10	AD-67
	I-10	Cloquintocet-mexyl
	I-10	dichlormid
	I-10	fenchlorazole-ethyl
	I-10	isoxadifen-ethyl
	I-10	mefenpyr-diethyl
	I-10	MON-7400
	I-10	flurazole
	I-10	furilazole
	I-10	fenclorim
	I-10	cumyluron
	I-10	daimuron/dymron
	I-10	dimepiperate
	I-10	IId-25
	I-10	IIe-11
	I-11	AD-67
	I-11	cloquintocet-mexyl
	I-11	dichlormid
	I-11	fenchlorazole-ethyl
	I-11	isoxadifen-ethyl
	I-11	mefenpyr-diethyl
	I-11	MON-7400
	I-11	flurazole
	I-11	furilazole
	I-11	fenclorim
	I-11	cumyluron
	I-11	daimuron/dymron
	I-11	dimepiperate
	I-11	IId-25
	I-11	IIe-11
	I-12	AD-67
	I-12	cloquintocet-mexyl
	I-12	dichlormid
	I-12	fenchlorazole-ethyl
	I-12	isoxadifen-ethyl
	I-12	mefenpyr-diethyl
	I-12	MON-7400
	I-12	flurazole
	I-12	furilazole
	I-12	fenclorim
	I-12	cumyluron
	I-12	daimuron/dymron
	I-12	dimepiperate
	I-12	IId-25
	I-12	IIe-11
	I-13	mefenpyr-diethyl
	I-2, sodium salt	IId-25
	I-15	mefenpyr-diethyl
	I-16	mefenpyr-diethyl
	I-17	mefenpyr-diethyl
	I-14	mefenpyr-diethyl
	I-18	mefenpyr-diethyl

Surprisingly, it has now been found that the above-defined active compound combinations of substituted thien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones of the general formula (I) and/or their salts and safeners (antidotes) of group (2) listed above, whilst being tolerated very well by crop plants, have particularly high herbicidal activity and can be used in various crops, in particular in cereal (especially wheat) and maize, but also in soya beans, potatoes and rice, for the selective control of weeds.
Here, it has to be considered to be surprising that, from a large number of known safeners or antidotes which are capable of antagonizing the damaging effect of a herbicide on the crop plants, that are in particular the abovementioned compounds of group (2) which neutralize the damaging effect of substituted thien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones on the crop plants virtually completely without negatively affecting the herbicidal activity with respect to the weeds.
Emphasis is given here to the particularly advantageous effect of the particularly and most preferred combination partners from group (2), in particular in respect of sparing cereal plants, such as, for example, wheat, barley and rye, but also maize and rice, as crop plants.
The active compound combinations according to the invention can be used, for example, in connection with the following plants:
Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindemia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cuburbita, Helianthus.
Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.
However, the use of the active compound combinations according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants. According to the invention, crop plants are all plants and plant varieties including transgenic plants and plant varieties, where on transgenic plants and plant varieties it is also possible for synergistic effects to occur.
The advantageous effect of the crop plant compatibility of the active compound combinations according to the invention is particularly highly pronounced at certain concentration ratios. However, the weight ratios of the active compounds in the active compound concentrations can be varied within relatively wide ranges. In general, 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, and particularly preferably 0.1 to 50 parts by weight and most preferably 1 to 25 parts by weight of one of the compounds which improve crop plant compatibility mentioned under group 2 above (antidotes/safeners) are present per part by weight of active compound of the formula (I) or its salts.
The active compounds or active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powder, dusting agents, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers.
If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.
Suitable solid carriers are:
for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, ground synthetic minerals, such as finely divided silica, alumina and silicates, suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-formers are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other possible additives are mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs: such as alizarin dyestuffs, azo dyestuffs and metal pbthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise from 0.1 to 95 per cent by weight of active compounds including the safeners, preferably between 0.5 and 90%.
The active compound combinations according to the invention are generally used in the form of finished formulations. However, the active compounds contained in the active compound combinations can also be mixed in individual formulations when used, i.e. in the form of tank mixes.
The novel active compound combinations, as such or in their formulations, can furthermore be used as a mixture with other known herbicides, finished formulations or tank mixes again being possible. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, growth factors, plant nutrients and agents which improve soil structure, is also possible. For certain intended uses, in particular in the post-emergence method, it may furthermore be advantageous to include, as further additives in the formulations, mineral or vegetable oils which are tolerated by plants (for example the commercial preparation “Rako Binol”), or ammonium salts such as, for example, ammonium sulphate or ammonium thiocyanate.
The novel active compound combinations can be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by washing, spraying, atomizing, dusting or scattering.
The amounts of the active compound combinations according to the invention applied can be varied within a certain range; they depend, inter alia, on the weather and on soil factors. In general, the application rates are between 0.001 and 5 kg per ha, preferably between 0.001 and 1 kg per ha, particularly preferably between 0.003 and 0.5 kg per ha.
The active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say by the pre-emergence and post-emergence method.

USE EXAMPLES

The active compound or safener components are in each case dissolved in a few ml (generally 2-3 ml) of solvent (generally acetone or N,N-dimethyl-formamide), and the solutions are combined and then—if appropriate after addition of an emulsifier—diluted with water to the desired concentration. In general, an aqueous spray liquor was prepared using 0.1% of the additive Renex-36.

Example A

Post-Emergence Test

The test plants are grown under controlled conditions (temperature, light, atmospheric humidity) in a greenhouse. The test plants are sprayed when they have reached a height of 5-15 cm. The concentration of the spray liquor is chosen such that the particular amounts of active compound desired are applied in 500 l of water/ha.
After spraying, the pots with the test plants are kept in a greenhouse chamber under controlled conditions (temperature, light, atmospheric humidity) until the test has ended. About three weeks after the application, the degree of damage to the crop plants is rated in % damage in comparison to the development of the untreated control.
The figures denote:

- 0%=no damage (like untreated control)
- 100%=total destruction/damage

Active compounds, application rates, test plants and results are shown in the tables below, the terms being used in the tables being as defined below:

maize=maize cv. “Pioneer”
a.i.=active ingredient=active compound/safener

TABLE A1

Post-emergence test/greenhouse

Active compound	Application rate	Damage maize
(+safener)	(g of a.i./ha)	(in %)

I-2	10	35
I-2 + AD-67	10 + 100	7
I-2 + cloquintocet-mexyl	10 + 100	1.5
I-2 + dichlormid	10 + 100	13.5
I-2 + fenchlorazole-ethyl	10 + 100	12
I-2 + isoxadifen-ethyl	10 + 100	4
I-2 + furilazole	10 + 100	2.5
I-2 + flurazole	10 + 100	4.5
I-2 + IIe-11	10 + 100	2
I-2 + MON-7400	10 + 100	1.5

Example A-2

Post-Emergence Test

Here, an aqueous spray liquor comprising 0.5% of the additive Renex-36 was prepared.

TABLE A-2-1

Post-emergence test/greenhouse

		Damage
		winter
	Application rate	barley
Active compound (+safener)	(g of a.i./ha)	(in %)

I-2, sodium salt	4	60
	2	50
I-2, sodium salt + Comp. No. IId-	4 + 100	50
25	2 + 100	25
	4 + 30	50
	2 + 30	35

TABLE A-2-2

Post-emergence test/greenhouse

		Damage
		winter
	Application rate	barley
Safener	(g of a.i./ha)	(in %)

Comp. No. IId-25	100	0
	30	0

Example A-3

Post-Emergence Test

The compound I-2 was used as 10 WP. In each case, Marlipal® was added in an amount of 500 ml/ha.
Evaluation was carried out as early as 7 days after the application.

Maize 1=maize of the cultivar “Prinz”
Maize 2=maize of the cultivar “Pioneer”
Maize 3=maize of the cultivar “LIXIS”

TABLE A-3-1

Post-emergence test/greenhouse

		Damage
	Application rate	Maize 1
Active compound (+safener)	(g of a.i./ha)	(in %)

I-2	15	20
	8	10
I-2 + Comp. No. IId-25	15 + 100	5
	8 + 100	0

TABLE A-3-2

Post-emergence test/greenhouse

		Damage
	Application rate	maize 2
Active compound (+safener)	(g of a.i./ha)	(in %)

I-2	15	20
	8	10
I-2 + Comp. No. IId-25	15 + 100	5
	8 + 100	5

TABLE A-3-3

Post-emergence test/greenhouse

		Damage
	Application rate	Maize 3
Active compound (+safener)	(g of a.i./ha)	(in %)

I-2	15	40
	8	20
I-2 + Comp. No. IId-25	15 + 100	20
	8 + 100	10
	15 + 50	10
	8 + 50	10

Example A-4

Post-Emergence Test

Mefenpyr-diethyl was used as 100 EC.
The compounds of Ex. Nos. I-2 and I-13 were used as 10 WP.

TABLE A-4-1

Post-emergence test/greenhouse

		Damage
	Application rate	winter
Safener	(g of a.i./ha)	wheat (in %)

	mefenpyr-diethyl	50	0

TABLE A-4-2

Post-emergence test/greenhouse

		Damage
	Application rate	winter
Active compound (+safener)	(g of a.i./ha)	wheat (in %)

I-2	30	60
	15	40
I-2 + mefenpyr-diethyl	30 + 50	10
	15 + 50	5

TABLE A-4-3

Post-emergence test/greenhouse

I-13	125	30
	60	20
I-13 + mefenpyr-diethyl	125 + 50	10
	60 + 50	5

TABLE A-4-4

Post-emergence test/greenhouse

		Damage
	Application rate	winter
Safener	(g of a.i./ha)	barley (in %)

	Mefenpyr-diethyl	50	0

TABLE A-4-5

Post-emergence test/greenhouse

		Damage
	Application rate	winter
Active compound (+safener)	(g of a.i./ha)	barley (in %)

I-2	30	80
	15	70
	8	50
I-2 + mefenpyr-diethyl	30 + 50	70
	15 + 50	40
	8 + 50	30

TABLE A-4-6

Post-emergence test/greenhouse

I-13	125	80
	60	70
	30	50
I-13 + mefenpyr-diethyl	125 + 50	60
	60 + 50	50
	30 + 50	30

Example A-5

Post-Emergence Test

Mefenpyr-diethyl was used as 100 EC and the compound of Ex. No. I-2 was used as 10 WP.

TABLE A-5-1

Post-emergence test/greenhouse

I-2	30	60
mefenpyr-diethyl	50	0
I-2 + mefenpyr-diethyl	30 + 50	5

TABLE A-5-2

Post-emergence test/greenhouse

Active compound	Application rate	Damage winter
(+ safener)	(g of a.i./ha)	wheat (in %)

I-13	125	50
mefenpyr-diethyl	50	0
I-13 + mefenpyr-diethyl	125 + 50	10

TABLE A-5-3

Post-emergence test/greenhouse

I-15	60	80
mefenpyr-diethyl	50	0
I-15 + mefenpyr-diethyl	60 + 50	40

TABLE A-5-4

Post-emergence test/greenhouse

I-16	60	25
mefenpyr-diethyl	50	0
I-16 + mefenpyr-diethyl	60 + 50	15

TABLE A-5-5

Post-emergence test/greenhouse

	Application rate	Damage winter
Safener	(g of a.i./ha)	wheat (in %)

	mefenpyr-diethyl	50	0

TABLE A-5-6

Post-emergence test/greenhouse

I-2	30	40
	15	30
	8	20
I-2 + mefenpyr-diethyl	30 + 50	20
	15 + 50	10
	8 + 50	10

TABLE A-5-7

Post-emergence test/greenhouse

I-17	30	70
	15	50
	8	40
I-17 + mefenpyr-diethyl	30 + 50	40
	15 + 50	30
	8 + 50	20

TABLE A-5-8

Post-emergence test/greenhouse

I-14	1	40
	0.5	20
I-14 + mefenpyr-diethyl	1 + 50	30
	0.5 + 50	10

TABLE A-5-9

Post-emergence test/greenhouse

I-18	2	50
	1	30
I-18 + mefenpyr-diethyl	2 + 50	20
	1 + 50	10

TABLE A-5-10

Post-emergence test/greenhouse

I-15	30	70
	15	40
	8	30
I-15 + mefenpyr-diethyl	30 + 50	10
	15 + 50	0
	8 + 50	0

TABLE A-5-11

Post-emergence test/greenhouse

	Application rate	Damage winter
Safener	(g of a.i./ha)	barley (in %)

	mefenpyr-diethyl	50	0

TABLE A-5-12

Post-emergence test/greenhouse

Active compound	Application rate	Damage winter
(+ safener)	(g of a.i./ha)	barley (in %)

I-2	30	80
	15	70
	8	60
I-2 + mefenpyr-diethyl	30 + 50	50
	15 + 50	20
	8 + 50	10

TABLE A-5-13

Post-emergence test/greenhouse

I-17	30	80
	15	70
	8	70
I-17 + mefenpyr-diethyl	30 + 50	70
	15 + 50	60
	8 + 50	20

TABLE A-5-14

Post-emergence test/greenhouse

I-14	0.5	30
	0.25	10
I-14 + mefenpyr-diethyl	0.5 + 50	20
	0.25 + 50	0

TABLE A-5-15

Post-emergence test/greenhouse

I-18	2	60
	1	20
	0.5	10
I-18 + mefenpyr-diethyl	2 + 50	20
	1 + 50	10
	0.5 + 50	0

TABLE A-5-19

Post-emergence test/greenhouse

I-15	30	80
	15	70
	8	60
I-15 + mefenpyr-diethyl	30 + 50	30
	15 + 50	20
	8 + 50	10

Claims

1. A composition comprising an active compound combination comprising

(a) a compound of formula (I)

or a salt thereof

and

(b) the crop-plant-compatibility-improving compound isoxadifen-ethyl, wherein the ratio of isoxadifen-ethyl per part by weight of said compound of formula I or a salt thereof is from 0.1 to 50.

2. The composition of claim 1, wherein the ratio of isoxadifen-ethyl per part by weight of said compound of formula I or a salt thereof is from 1 to 25.

3. The composition of claim 1, further comprising one or more of extenders, solid carriers, emulsifiers, foam-formers, dispersants, tackifiers, colorants, mineral oil, or vegetable oil.

4. The composition of claim 1, further comprising another herbicide, fungicide, insecticide, acaricide, nematicide, bird repellent, growth factor, and/or plant nutrient and agent.

5. The composition of claim 1, wherein component (a) and component (b) are the only two actives present in the composition.

6. The composition of claim 1, wherein component (a) is the only herbicide present in the composition.

7. A method for controlling undesirable plants comprising allowing an effective amount of the composition according to claim 1 to act on undesirable plants and/or their habitat.

8. A process for preparing a herbicidal composition comprising mixing the composition according to claim 1 with one or more surfactants and/or extenders.

9. The method according to claim 7, wherein the undesired plants are controlled in areas of growing maize.

10. The method according to claim 9, wherein 0.001 to 5 kg per ha of the composition are applied.

11. The method according to claim 9, wherein 0.001 to 1 kg per ha of the composition are applied.

12. The method according to claim 9, wherein 0.003 to 0.5 kg per ha of the composition are applied.

13. The method according to claim 9, wherein the composition is applied pre-emergence.

14. The method according to claim 9, wherein the composition is applied post-emergence.