U.S. patent application number 10/489092 was filed with the patent office on 2005-01-13 for selective herbicides based on substituted thien-3-yl-sulfonylamino(thio)ca- rbonyltriazolin(thi)ones and safeners.
Invention is credited to Dahmen, Peter, Drewes, Mark Wilhelm, Feucht, Dieter, Gesing, Ernst Rudolf F., Muller, Klaus-Helmut, Pontzen, Rolf, Schwarz, Hans-Georg.
Application Number | 20050009705 10/489092 |
Document ID | / |
Family ID | 7699812 |
Filed Date | 2005-01-13 |
United States Patent
Application |
20050009705 |
Kind Code |
A1 |
Feucht, Dieter ; et
al. |
January 13, 2005 |
Selective herbicides based on substituted
thien-3-yl-sulfonylamino(thio)ca- rbonyltriazolin(thi)ones and
safeners
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) 1 in which
Q.sup.1, Q.sup.2, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are 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.
Inventors: |
Feucht, Dieter; (Monheim,
DE) ; Dahmen, Peter; (Neuss, DE) ; Drewes,
Mark Wilhelm; (Langenfeld, DE) ; Pontzen, Rolf;
(Leichlingen, DE) ; Gesing, Ernst Rudolf F.;
(Erkrath, DE) ; Schwarz, Hans-Georg; (Langenfeld,
DE) ; Muller, Klaus-Helmut; (Dusseldorf, DE) |
Correspondence
Address: |
BAYER CROPSCIENCE LP
Patent Department
100 BAYER ROAD
PITTSBURGH
PA
15205-9741
US
|
Family ID: |
7699812 |
Appl. No.: |
10/489092 |
Filed: |
September 7, 2004 |
PCT Filed: |
September 10, 2002 |
PCT NO: |
PCT/EP02/10104 |
Current U.S.
Class: |
504/277 |
Current CPC
Class: |
A01N 43/653 20130101;
A01N 25/32 20130101; A01N 47/38 20130101; A01N 47/38 20130101; A01N
2300/00 20130101; A01N 47/38 20130101; A01N 25/32 20130101; A01N
2300/00 20130101 |
Class at
Publication: |
504/277 |
International
Class: |
A01N 043/50 |
Foreign Application Data
Date |
Code |
Application Number |
Sep 21, 2001 |
DE |
10146590.4 |
Claims
What is claimed is:
1-9. (canceled)
10. A composition comprising an active compound combination
comprising (a) one or more compounds of formula (I) 63or salts
thereof, in which Q.sup.1 represents O or S, Q.sup.2 represents O
or S, R.sup.1 represents optionally cyano-, halogen-, or
C.sub.1-C.sub.4-alkoxy-substituted alkyl having 1 to 6 carbon
atoms; represents optionally cyano- or halogen-substituted alkenyl
or alkynyl having in each case 2 to 6 carbon atoms; represents
optionally cyano-, halogen-, or C.sub.1-C.sub.4-alkyl-s- ubstituted
cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon
atoms in the cycloalkyl group and, where appropriate, 1 to 4 carbon
atoms in any alkyl moiety; represents optionally nitro-, cyano-,
halogen-, C.sub.1-C.sub.4-alkyl-, or
C.sub.1-C.sub.4-alkoxy-substituted aryl or arylalkyl having in each
case 6 or 10 carbon atoms in the aryl group and, where appropriate,
1 to 4 carbon atoms in any alkyl moiety; or represents optionally
nitro-, cyano-, halogen-, C.sub.1-C.sub.4-alkyl-, or
C.sub.1-C.sub.4-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, where appropriate, 1 to 4
carbon atoms in any alkyl moiety, R.sup.2 represents hydrogen,
cyano, nitro, or halogen; represents optionally cyano-, halogen-,
or C.sub.1-C.sub.4-alkoxy-substituted alkyl, alkoxy,
alkoxycarbonyl, alkylthio, alkylsulphinyl, or alkylsulphonyl having
in each case 1 to 6 carbon atoms in the alkyl group; or represents
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, R.sup.3 represents hydrogen,
hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, or
iodine, represents optionally fluorine-, chlorine-, bromine-,
cyano-, C.sub.1-C.sub.4-alkoxy-, C.sub.1-C.sub.4-alkyl-carbonyl-,
or C.sub.1-C.sub.4-alkoxy-carbonyl-subst- ituted alkyl having 1 to
6 carbon atoms; represents optionally fluorine-, chlorine-, and/or
bromine- substituted alkenyl or alkynyl having in each case 2 to 6
carbon atoms; represents optionally fluorine-, chlorine-, cyano-,
C.sub.1-C.sub.4-alkoxy-, or C.sub.1-C.sub.4-alkoxy-carbonyl-subst-
ituted 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 having in each case 1 to
4 carbon atoms in the alkyl groups; represents optionally methyl-
and/or ethyl-substituted aziridino, pyrrolidino, piperidino, or
morpholino; represents optionally fluorine-, chlorine-, bromine-,
cyano-, and/or C.sub.1-C.sub.4-alkyl-subs- tituted 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, where appropriate, 1 to 4
carbon atoms in any alkyl moiety; or represents optionally
fluorine-, chlorine-, bromine-, cyano-, nitro-,
C.sub.1-C.sub.4-alkyl-, trifluoromethyl-, C.sub.1-C.sub.4-alkoxy-
and/or C.sub.1-C.sub.4-alkoxy-carbonyl-substitute- d aryl,
arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino,
or arylalkylamino having in each case 6 or 10 carbon atoms in the
aryl group and, where appropriate, 1 to 4 carbon atoms in any alkyl
moiety, R.sup.4 represents hydrogen, hydroxyl, amino, or cyano;
represents C.sub.2-C.sub.10-alkylideneamino; represents optionally
fluorine-, chlorine-, bromine-, cyano-, C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-alkyl-carbonyl-, or
C.sub.1-C.sub.4-alkoxy-carbonyl-subst- ituted alkyl having 1 to 6
carbon atoms; represents optionally fluorine-, chlorine-, and/or
bromine-substituted alkenyl or alkynyl having in each case 2 to 6
carbon atoms; represents optionally fluorine-, chlorine-, bromine-,
cyano-, C.sub.1-C.sub.4-alkoxy-, or C.sub.1-C.sub.4-alkoxy-carb-
onyl-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 optionally fluorine-, chlorine-, bromine-, cyano-,
and/or C.sub.1-C.sub.4-alkyl-substituted cycloalkyl,
cycloalkylamino, or cycloalkylalkyl having in each case 3 to 6
carbon atoms in the alkyl group and, where appropriate, 1 to 4
carbon atoms in any alkyl moiety; or represents optionally
fluorine-, chlorine-, bromine-, cyano- nitro-, C.sub.1-C4-alkyl-,
trifluoromethyl-, and/or C.sub.1-C.sub.4-alkoxy-substituted aryl or
arylalkyl having in each case 6 or 10 carbon atoms in the aryl
group and, where appropriate, 1 to 4 carbon atoms in any alkyl
moiety, or R.sup.3 and R.sup.4 together represent optionally
branched alkanediyl having 3 to 6 carbon atoms, and (b) at least
one compound that improves crop plant compatibility selected from
the group consisting of the compounds
4-dichloroacetyl-1-oxa-4-aza-s- piro[4.5]-decane (AD-67, MON-4660),
1-dichloroacetyl-hexahydro-3,3,8a-trim-
ethylpyrrolo[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),
3-(2-chloro-benzyl)-1-(1-methyl-1-phenyl-ethyl)-urea (cumyluron),
.alpha.-(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-carboxylat-
e (fenchlorazole-ethyl--cf. also related compounds in EP-A-174562
and EP-A-346620), phenyl-methyl
2-chloro-4-trifluoromethyl-thiazole-5-carboxy- late (flurazole),
4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-.alpha.-trifluoro-
-acetophenone oxime (fluxofenim),
3-dichloroacetyl-5-(2-furanyl)-2,2-dimet- hyl-oxazolidine
(furilazole, MON-13900), ethyl-4,5-dihydro-5,5-diphenyl-3--
isoxazolecarboxylate (isoxadifen-ethyl), 1-(ethoxycarbonyl)-ethyl
3,6-dichloro-2-methoxybenzoate (lactidichlor),
(4-chloro-o-tolyloxy)-acet- ic acid (MCPA),
2-(4-chloro-o-tolyloxy)-propionic acid (mecoprop), diethyl
1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate
(mefenpyr-diethyl), 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,
.alpha.-(1,3-dioxolan-2-yl-methoximino)-phenyla- cetonitrile
(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), ethyl diphenylmethoxyacetate, methyl
1-(2-chloro-phenyl)-5-phenyl-1H-pyra- zole-3-carboxylate, ethyl
1-(2,4-dichloro-phenyl)-5-methyl-1H-pyrazole-3-c- arboxylate, ethyl
1-(2,4-dichloro-phenyl)-5-isopropyl-1H-pyrazole-3-carbox- ylate,
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-carboxyl- ate, 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,
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, 4-carboxy-chroman-4-yl-acetic
acid (AC-304415), 4-chloro-phenoxyacetic acid,
3,3'-dimethyl-4-methoxy-benzoph- enone,
1-bromo-4-chloromethylsulphonyl-benzene,
1-[4-(N-2-methoxy-benzoyls- ulphamoyl)-phenyl]-3-methyl-urea (alias
N-(2-methoxy-benzoyl)-4-[(methylam-
ino-carbonyl)-amino]-benzenesulphonamide),
1-[4-(N-2-methoxy-benzoylsulpha- moyl)-phenyl]-3,3-dimethyl-urea,
1-[4-(N-4,5-dimethylbenzoyl-sulphamoyl)-p- henyl]-3-methyl-urea,
1-[4-(N-naphthylsulphamoyl)-phenyl]-3,3-dimethyl-ure- a,
N-(2-methoxy-5-methyl-benzoyl)-4-(cyclopropylamino-carbonyl)-benzenesul-
phonamide, and a compound of formula (IIa) 64where, for each of
formulas (IIa), (IIb), or (IIc), n represents a number between 0
and 5, A.sup.1 represents one of the divalent heterocyclic groups
65A.sup.2 represents optionally C.sub.1-C.sub.4-alkyl- and/or
C.sub.1-C.sub.4-alkoxy-carbonyl-- substituted alkanediyl having 1
or 2 carbon atoms, R.sup.5 represents hydroxyl, mercapto, amino,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylamino, or di-(C.sub.1-C.sub.4-alkyl)-amino,
R.sup.6 represents hydroxyl, mercapto or amino; or optionally
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, or
C.sub.2-C.sub.4-alkenoxy-substituted C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylamino, or di-(C.sub.1-C.sub.4-alkyl)-amino,
R.sup.7 represents optionally fluorine-, chlorine-, and/or
bromine-substituted C.sub.1-C.sub.4-alkyl, R.sup.8 represents
hydrogen; optionally fluorine-, chlorine-, and/or
bromine-substituted C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
or C.sub.2-C.sub.6-alkynyl;
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
dioxolanyl-C.sub.1-C.sub.4-- alkyl, furyl,
furyl-C.sub.1-C.sub.4-alkyl, thienyl, thiazolyl, or piperidinyl; or
optionally fluorine-, chlorine-, and/or bromine-, or
C.sub.1-C.sub.4-alkyl-substituted phenyl, R.sup.9 represents
hydrogen; optionally fluorine-, chlorine-, and/or
bromine-substituted C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
or C.sub.2-C.sub.6-alkynyl;
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
dioxolanyl-C.sub.1-C.sub.4-alkyl, furyl,
furyl-C.sub.1-C.sub.4-alkyl, thienyl, thiazolyl, or piperidinyl, or
optionally fluorine-, chlorine-, and/or bromine-, or
C.sub.1-C.sub.4-alkyl-substituted phenyl; or R.sup.9 together with
R.sup.8 represents C.sub.3-C.sub.6-alkanediyl or
C.sub.2-C.sub.5-oxaalkanediyl, each of which is optionally
substituted by C.sub.1-C.sub.4-alkyl, phenyl, furyl, a fused-on
benzene ring, or by two substituents that together with the C atom
to which they are attached form a 5- or 6-membered carbocycle,
R.sup.10 represents hydrogen, cyano, or halogen; or represents
optionally fluorine, chlorine-, and/or bromine-substituted
C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, or phenyl,
R.sup.11 represents hydrogen; or optionally hydroxyl-, cyano-,
halogen-, or C.sub.1-C.sub.4-alkoxy-substituted
C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, or
tri-(C.sub.1-C.sub.4-alkyl)-silyl, R.sup.12 represents hydrogen,
cyano, or halogen; or represents optionally fluorine-, chlorine-,
and/or bromine-substituted C.sub.1-C.sub.4-alkyl,
C.sub.3-C.sub.6-cycloalkyl, or phenyl, X.sup.1 represents nitro,
cyano, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy, or C.sub.1-C.sub.4-haloalkoxy, X.sup.2
represents hydrogen, cyano, nitro, halogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, or
C.sub.1-C.sub.4-haloalkoxy, X.sup.3 represents hydrogen, cyano,
nitro, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy, or C.sub.1-C.sub.4-haloalkoxy, and a
compound of formula (IId) 66formula (IIe) 67where, for each of
formulas (IId) or (IIe), n represents a number between 0 and 5,
R.sup.13 represents hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.14
represents hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.15 represents
hydrogen; optionally cyano-, halogen-, or
C.sub.1-C.sub.4-alkoxy-substituted C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylamino or di-(C.sub.1-C.sub.4-alkyl)-amino; or
optionally cyano-, halogen-, or C.sub.1-C.sub.4-alkyl-substituted
C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyloxy,
C.sub.3-C.sub.6-cycloalkylthio, or C.sub.3-C.sub.6-cycloalkylamino,
R.sup.16 represents hydrogen; optionally cyano-, hydroxyl-,
halogen-, or C.sub.1-C.sub.4-alkoxy-substituted
C.sub.1-C.sub.6-alkyl; optionally cyano- or halogen-substituted
C.sub.3-C.sub.6-alkenyl or C.sub.3-C.sub.6-alkynyl; or optionally
cyano-, halogen-, or C.sub.1-C.sub.4-alkyl-substituted
C.sub.3-C.sub.6-cycloalkyl, R.sup.17 represents hydrogen;
optionally cyano-, hydroxyl-, halogen-, or
C.sub.1-C.sub.4-alkoxy-substituted C.sub.1-C.sub.6-alkyl;
optionally cyano- or halogen-substituted C.sub.3-C.sub.6-alkenyl or
C.sub.3-C.sub.6-alkynyl; optionally cyano-, halogen-, or
C.sub.1-C.sub.4-alkyl-substituted C.sub.3-C.sub.6-cycloalkyl; or
optionally nitro-, cyano-, halogen-, C.sub.1-C.sub.4-alkyl-,
C.sub.1-C.sub.4-halogenoalkyl-, C.sub.1-C.sub.4-alkoxy-, or
C.sub.1-C.sub.4-halogenoalkoxy-substituted phenyl; or R.sup.17
together with R.sup.16 represents optionally
C.sub.1-C.sub.4-alkyl-substituted C.sub.2-C.sub.6-alkanediyl or
C.sub.2-C.sub.5-oxaalkanediyl, X.sup.4 represents nitro, cyano,
carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalky- l,
C.sub.1-C.sub.4-alkoxy, or C.sub.1-C.sub.4-haloalkoxy, and X.sup.5
represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl,
hydroxyl, amino, halogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-haloalky- l, C.sub.1-C.sub.4-alkoxy, or
C.sub.1-C.sub.4-haloalkoxy.
11. A composition according to claim 10 wherein Q.sup.1 represents
O or S, Q.sup.2 represents O or S, R.sup.1 represents optionally
cyano-, fluorine-, chlorine-, methoxy-, or ethoxy-substituted
methyl, ethyl, n- or i-propyl, or n-, i-, s-, or t-butyl;
represents optionally cyano-, fluorine-, or chlorine-substituted
propenyl, butenyl, propynyl, or butynyl; represents optionally
cyano-, fluorine-, chlorine-, methyl-, or ethyl-substituted
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, or
cyclohexylmethyl; represents optionally cyano-, fluorine-,
chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-,
trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,
difluoromethoxy-, or trifluoromethoxy-substitu- ted phenyl,
phenylmethyl, or phenylethyl; or represents optionally cyano-,
fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-,
methoxy-, ethoxy-, or n- or i-propoxy-substituted heterocyclyl or
heterocyclyl-methyl, where each heterocyclyl group is selected from
the group consisting of oxetanyl, thietanyl, furyl,
tetrahydrofuryl, thienyl, and tetrahydrothienyl, R.sup.2 represents
hydrogen, cyano, fluorine, chlorine, or bromine; represents
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 optionally cyano-, fluorine-, or
chlorine-substituted propenyl, butenyl, propynyl, butynyl,
propenyloxy, butenyloxy, propynyloxy, or butynyloxy, R.sup.3
represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine,
chlorine, or bromine; represents optionally fluorine-, chlorine-,
cyano-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-,
n- or i-butyroyl, methoxycarbonyl-, ethoxycarbonyl-, or n- or
i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, or n-,
i-, s-, or t-butyl; represents optionally fluorine-, chlorine-,
and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl,
propynyl, or butynyl; represents optionally fluorine-, chlorine-,
cyano-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-,
ethoxycarbonyl-, or 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, propynylthio, butynylthio,
propenylamino, butenylamino, propynylamino, or butynylamino;
represents dimethylamino, diethylamino, or dipropylamino;
represents 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,
cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,
cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy,
cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio,
cyclopentylmethylthio, cyclohexylmethylthio,
cyclopropylmethylamino, cyclobutylmethylamino,
cyclopentylmethylamino, or cyclohexylmethylamino; or represents
optionally fluorine-, chlorine-, bromine-, methyl-,
trifluoromethyl-, methoxy-, or methoxy-carbonyl-substi- tuted
phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio,
phenylamino, or benzylamino, and R.sup.4 represents hydrogen,
hydroxyl, or amino; represents optionally fluorine-, chlorine-,
cyano-, methoxy-, or ethoxy-substituted methyl, ethyl, n- or
i-propyl, or n-, i-, s-, or t-butyl; represents optionally
fluorine, chlorine, and/or bromine-substituted ethenyl, propenyl,
butenyl, propynyl, or butynyl; represents 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, or n-, i-, s-, or t-butylamino; represents
propenyloxy or butenyloxy; represents dimethylamino or
diethylamino; represents optionally fluorine-, chlorine-, methyl-,
and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,
cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino,
cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,
cyclopentylmethyl, or cyclohexylmethyl; or represents optionally
fluorine-, chlorine-, methyl-, trifluoromethyl-, and/or
methoxy-substituted phenyl or benzyl, or R.sup.3 and R.sup.4
together represent trimethylene (propane-1,3-diyl), tetramethylene
(butane-1,4-diyl), or pentamethylene (pentane-1,5-diyl).
12. A composition according to claim 10 wherein Q.sup.1 represents
O, Q.sup.2 represents O, R.sup.1 represents optionally fluorine-,
chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, or n- or
i-propyl, R.sup.2 represents fluorine, chlorine, or bromine; or
represents optionally fluorine-, chlorine-, methoxy-, or
ethoxy-substituted methyl, ethyl, or n- or i-propyl, R.sup.3
represents hydrogen, chlorine, or bromine; represents optionally
fluorine-, chlorine-, methoxy-, ethoxy-, or n- or
i-propoxy-substituted methyl, ethyl, or n- or i-propyl; represents
optionally fluorine- or chlorine-substituted ethenyl, propenyl,
butenyl, propynyl, or butynyl; represents optionally fluorine-,
chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted
methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or
i-propylthio, methylamino, ethylamino, or n- or i-propylamino;
represents propenyloxy, propynyloxy, propenylthio, propynylthio,
propenylamino, or propynylamino; represents dimethylamino or
diethylamino; represents optionally fluorine-, chlorine-, or
methyl-substituted cyclopropyl, cyclopropyloxy, cyclopropylmethyl,
or cyclopropylmethoxy, and R.sup.4 represents optionally fluorine-,
chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, or n- or
i-propyl; represents optionally fluorine- or chlorine-substituted
ethenyl, propenyl, or propynyl; represents optionally fluorine-,
chlorine-, methoxy-, or ethoxy-substituted methoxy, ethoxy, or n-
or i-propoxy; represents methylamino; or represents
cyclopropyl.
13. A composition according to claim 10 wherein n represents the
numbers 0, 1, 2, 3, or 4, A.sup.2 represents optionally methyl-,
ethyl-, methoxycarbonyl-, or ethoxycarbonyl-substituted methylene
or ethylene, R.sup.5 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, R.sup.6 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, R.sup.7 represents optionally fluorine-, chlorine-,
and/or bromine-substituted methyl, ethyl, or n- or i-propyl,
R.sup.8 represents hydrogen; optionally fluorine- and/or
chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-, or
t-butyl, propenyl, butenyl, propynyl, butynyl, methoxymethyl,
ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl,
furylmethyl, thienyl, thiazolyl, piperidinyl; or optionally
fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, or n-, i-,
s-, or t-butyl-substituted phenyl, R.sup.9 represents hydrogen;
optionally fluorine- and/or chlorine-substituted methyl, ethyl, n-
or i-propyl, n-, i-, s-, or t-butyl, propenyl, butenyl, propynyl,
butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,
dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl,
piperidinyl; or optionally fluorine-, chlorine-, methyl-, ethyl-,
n- or i-propyl-, or n-, i-, s-, or t-butyl-substituted phenyl; or
R.sup.9 together with R.sup.8 represents one of the radicals
--CH.sub.2--O--CH.sub.2-CH.sub.2-- or
--CH.sub.2-CH.sub.2--O--CH.sub.2-CH.sub.2--, which are optionally
substituted by methyl, ethyl, furyl, phenyl, a fused benzene ring,
or by two substituents that together with the C atom to which they
are attached form a 5- or 6-membered carbocycle, R.sup.10
represents hydrogen, cyano, fluorine, chlorine, or bromine; or
represents optionally fluorine-, chlorine-, and/or
bromine-substituted methyl, ethyl, n- or i-propyl, cyclopropyl,
cyclobutyl, cyclopentyl, cyclohexyl, or phenyl, R.sup.11 represents
hydrogen; or optionally hydroxyl-, cyano-, fluorine-, chlorine,
methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n-
or i-propyl, or n-, i-, s-, or t-butyl, R.sup.12 represents
hydrogen, cyano, fluorine, chlorine, or bromine; or represents
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, X.sup.1 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, X.sup.2 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, X.sup.3 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, R.sup.13 represents hydrogen,
methyl, ethyl, or n- or i-propyl, R.sup.14 represents hydrogen,
methyl, ethyl, or n- or i-propyl, R.sup.15 represents hydrogen;
optionally cyano-, fluorine-, chlorine-, methoxy- ethoxy-, or 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 optionally
cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, or n- or
i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,
cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,
cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio,
cyclohexylthio, cyclopropylamino, cyclobutylamino,
cyclopentylamino, or cyclohexylamino, R.sup.16 represents hydrogen;
optionally cyano-, hydroxyl-, fluorine- chlorine-, methoxy-,
ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or
i-propyl, or n-, i-, or s-butyl; optionally cyano-, fluorine-,
chlorine-, or bromine-substituted propenyl, butenyl, propynyl, or
butynyl; or optionally cyano-, fluorine-, chlorine-, bromine-,
methyl- ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl,
cyclopentyl, or cyclohexyl, R.sup.17 represents hydrogen;
optionally cyano-, hydroxyl-, fluorine- chlorine-, methoxy-,
ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or
i-propyl, or n-, i-, or s-butyl; optionally cyano-, fluorine-,
chlorine-, or bromine-substituted propenyl, butenyl, propynyl, or
butynyl; or optionally cyano-, fluorine-, chlorine-, bromine-,
methyl- ethyl-, or 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 R.sup.17 together with
R.sup.16 represents in each case optionally methyl- or
ethyl-substituted butane-1,4-diyl (trimethylene), pentane-1,5-diyl,
1-oxabutane-1,4-diyl, or 3-oxapentane-1,5-diyl, X.sup.4 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, and X.sup.5
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.
14. A composition according to claim 10 wherein the
crop-plant-compatibility-improving compound is one or more
compounds selected from the group consisting of the active
compounds AD-67, cloquintocet-mexyl, dichlormid,
fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, MON-7400,
flurazole, furilazole, fenchlorim, cumyluron, dymron, a compound of
formula (IId) 68in which R.sup.13 and R.sup.14 each represent
hydrogen, R.sup.15 represents methoxymethyl, (X.sup.4).sub.n
represents 2-methoxy, and (X.sup.5).sub.n represents hydrogen, and
a compound of formula (IIe) 69in which R.sup.13 and R.sup.16 each
represent hydrogen, R.sup.17 represents cyclopropyl,
(X.sup.4).sub.n represents the group 2-methoxy or the two groups
2-methoxy and 5-methyl, and (X.sup.5).sub.n represents
hydrogen.
15. A composition according to claim 10 comprising an active
compound combination comprising (a) a compound of formula (I) 70or
a salt thereof, in which Q.sup.1 and Q.sup.2 each represent oxygen,
R.sup.1, R.sup.2, and R.sup.4 each represent methyl, and R.sup.3
represents methoxy, and (b) a crop-plant-compatibility-improving
compound of formula (IIe) 71in which R.sup.13 and R.sup.16 each
represent hydrogen, R.sup.17 represents cyclopropyl,
(X.sup.4).sub.n represents 2-methoxy, and (X.sup.5).sub.n
represents hydrogen.
16. A method for controlling undesirable plants comprising allowing
an effective amount of a composition according to claim 10 to act
on undesirable plants and/or their habitat.
17. A process for preparing a herbicidal composition comprising
mixing a composition according to claim 10 with one or more
surfactants and/or extenders.
Description
[0001] The invention relates to novel selective herbicidal active
compound combinations which comprise substituted
thien-3-ylsulphonylamino(thio)car- bonyltriazolin(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.
[0002] Substituted
thien-3-ylsulphonylamino(thio)carbonyltriazoline(ethi)o- nes 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.
[0003] 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.
[0004] The invention provides selective herbicidal compositions,
characterized by an effective amount of an active compound
combination comprising
[0005] (a) substituted
thien-3-ylsulphonylamino(thio)carbonyltriazolin(eth- i)ones of the
formula (I) 2
[0006] in which
[0007] Q.sup.1 represents O (oxygen) or S (sulphur),
[0008] Q.sup.2 represents O (oxygen) or S (sulphur),
[0009] R.sup.1 represents optionally cyano-, halogen- or
C.sub.1-C.sub.4-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 C.sub.1-C.sub.4-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-,
C.sub.1-C.sub.4-alkyl- or C.sub.1-C.sub.4-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-,
C.sub.1-C.sub.4-alkyl- or C.sub.1-C.sub.4-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,
[0010] R.sup.2 represents hydrogen, cyano, nitro, halogen,
represents in each case optionally cyano-, halogen- or
C.sub.1-C.sub.4-alkoxy-substitut- ed 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,
[0011] R.sup.3 represents hydrogen, hydroxyl, mercapto, amino,
cyano, fluorine, chlorine, bromine, iodine, represents optionally
fluorine-, chlorine-, bromine-, cyano-, C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-alkyl-carbonyl- or
C.sub.1-C.sub.4-alkoxy-carbonyl-substi- tuted 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-, C.sub.1-C.sub.4-alkoxy- or
C.sub.1-C.sub.4-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 having 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 C.sub.1-C.sub.4-alkyl-subst-
ituted 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-, C.sub.1-C.sub.4-alkyl-, trifluoromethyl-,
C.sub.1-C.sub.4-alkoxy- and/or C.sub.1-C.sub.4-alkoxy-c-
arbonyl-substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio,
arylalkylthio, arylamino or 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,
[0012] R.sup.4 represents hydrogen, hydroxyl, amino, cyano,
represents C.sub.2-C.sub.10-alkylidene-amino, represents optionally
fluorine-, chlorine-, bromine-, cyano-, C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-alkyl-carbonyl- or
C.sub.1-C.sub.4-alkoxy-carbonyl-substi- tuted 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-, C.sub.1-C.sub.4-alkoxy- or
C.sub.1-C.sub.4-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
C.sub.1-C.sub.4-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-, C.sub.1-C.sub.4-alkyl-, trifluoromethyl-
and/or C.sub.1-C.sub.4-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
[0013] R.sup.3 and R.sup.4 together represent optionally branched
alkanediyl having 3 to 6 carbon atoms,
[0014] and salts of the compounds of the formula (I)
[0015] ("active compounds of group 1")
[0016] and
[0017] (b) at least one compound which improves crop plant
compatibility, from the group of compounds below:
[0018] 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),
.alpha.-(cyanomethoximino)-phenylacetonitr- ile (cyometrinil),
2,4-dichloro-phenoxyacetic acid (2,4-D),
4-(2,4-dichloro-phenoxy)-butyric acid (2,4-DB),
1-(1-methyl-1-phenyl-ethy- l)-3-(4-methyl-phenyl)-urea (daimuron,
dymron), 3,6-dichloro-2-methoxy-ben- zoic acid (dicamba),
S-1-methyl-1-phenyl-ethyl piperidine-1-thiocarboxylat- e
(dimepiperate),
2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-pr-
openyl)-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-carboxylat-
e (fenchlorazole-ethyl--cf. also related compounds in EP-A-174562
and EP-A-346620), phenyl-methyl
2-chloro-4-trifluoromethyl-thiazole-5-carboxy- late (flurazole),
4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-.alpha.-trifluoro-
-acetophenone oxime (fluxofenim),
3-dichloroacetyl-5-(2-furanyl)-2,2-dimet- hyl-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-dicarboxylat-
e (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-azas- piro[4.5]decane 4-carbodithioate (MG-838),
1,8-naphthalic anhydride,
.alpha.-(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-acet- ate, 2-oxo-prop-1-yl
5-chloro-quinolin-8-oxy-acetate, diethyl
5-chloro-quinolin-8-oxy-malonate, diallyl
5-chloro-quinolin-8-oxy-malonat- e, 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-benzop- henone,
1-bromo-4-chloromethylsulphonyl-benzene, 1-[4-(N-2-methoxybenzoyls-
ulphamoyl)-phenyl]-3-methyl-urea (alias
N-(2-methoxy-benzoyl)-4-[(methylam-
ino-carbonyl)-amino]-benzenesulphonamide),
1-[4-(N-2-methoxybenzoylsulpham- oyl)-phenyl]-3,3-dimethyl-urea,
1-[4-(N-4,5-dimethylbenzoylsulphamoyl)-phe- nyl]-3-methyl-urea,
1-[4-(N-naphthylsulphamoyl)-phenyl]-3,3-dimethyl-urea,
N-(2-methoxy-5-methyl-benzoyl)-4-(cyclopropyl-aminocarbonyl)-benzenesulph-
onamide,
[0019] and/or the following compounds
[0020] of the formula (IIa) 3
[0021] or the formula (IIb) 4
[0022] or the formula (IIc) 5
[0023] where
[0024] n represents a number between 0 and 5,
[0025] A.sup.1 represents one of the divalent heterocyclic
groupings shown below, 6
[0026] A.sup.2 represents optionally C.sub.1-C.sub.4-alkyl- and/or
C.sub.1-C.sub.4-alkoxy-carbonyl-substituted alkanediyl having 1 or
2 carbon atoms,
[0027] R.sup.5 represents hydroxyl, mercapto, amino,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylamino or di-(C.sub.1-C.sub.4-alkyl)-amino,
[0028] R.sup.6 represents hydroxyl, mercapto, amino, in each case
optionally C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy or
C.sub.2-C.sub.4-alkenoxy-substituted C.sub.1-C.sub.6-alkoxy,
C.sub.2-C.sub.6-alkenoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylamino or di-(C.sub.1-C.sub.4-alkyl)-amino,
[0029] R.sup.7 represents in each case optionally fluorine-,
chlorine- and/or bromine-substituted C.sub.1-C.sub.4-alkyl,
[0030] R.sup.8 represents hydrogen, in each case optionally
fluorine-, chlorine- and/or bromine-substituted
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
dioxolanyl-C.sub.1-C.sub.4-- alkyl, furyl,
furyl-C.sub.1-C.sub.4-alkyl, thienyl, thiazolyl, piperidinyl, or
optionally fluorine-, chlorine- and/or bromine- or
C.sub.1-C.sub.4-alkyl-substituted phenyl,
[0031] R.sup.9 represents hydrogen, in each case optionally
fluorine-, chlorine- and/or bromine-substituted
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or
C.sub.2-C.sub.6-alkynyl,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl,
dioxolanyl-C.sub.1-C.sub.4-- alkyl, furyl,
furyl-C.sub.1-C.sub.4-alkyl, thienyl, thiazolyl, piperidinyl, or
optionally fluorine-, chlorine- and/or bromine- or
C.sub.1-C.sub.4-alkyl-substituted phenyl, or together with R.sup.8
represents C.sub.3-C.sub.6-alkanediyl or
C.sub.2-C.sub.5-oxaalkanediyl, each of which is optionally
substituted by C.sub.1-C.sub.4-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,
[0032] R.sup.10 represents hydrogen, cyano, halogen, or represents
in each case optionally fluorine, chlorine- and/or
bromine-substituted C.sub.1-C.sub.4-alkyl,
C.sub.3-C.sub.6-cycloalkyl or phenyl,
[0033] R.sup.11 represents hydrogen, optionally hydroxyl-, cyano-,
halogen- or C.sub.1-C.sub.4-alkoxy-substituted
C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl or
tri-(C.sub.1-C.sub.4-alkyl)-silyl,
[0034] R.sup.12 represents hydrogen, cyano, halogen, or represents
in each case optionally fluorine-, chlorine- and/or
bromine-substituted C.sub.1-C.sub.4-alkyl,
C.sub.3-C.sub.6-cycloalkyl or phenyl,
[0035] X.sup.1 represents nitro, cyano, halogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy,
[0036] X.sup.2 represents hydrogen, cyano, nitro, halogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy,
[0037] X.sup.3 represents hydrogen, cyano, nitro, halogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy,
[0038] where X.sup.1 is preferably found at the (2) and (4)
positions, X.sup.2 is preferably found at the (5) position and
X.sup.3 is found at the (2) position,
[0039] and/or the following compounds
[0040] of the formula (IId) 7
[0041] or the formula (IIe) 8
[0042] where
[0043] n again represents a number between 0 and 5,
[0044] R.sup.13 represents hydrogen or C.sub.1-C.sub.4-alkyl,
[0045] R.sup.14 represents hydrogen or C.sub.1-C.sub.4-alkyl,
[0046] R.sup.15 represents hydrogen, in each case optionally
cyano-, halogen- or C.sub.1-C.sub.4-alkoxy-substituted
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylamino or
di-(C.sub.1-C.sub.4-alkyl)-amino, or in each case optionally
cyano-, halogen- or C.sub.1-C.sub.4-alkyl-substitute- d
C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyloxy,
C.sub.3-C.sub.6-cycloalkylthio or
C.sub.3-C.sub.6-cycloalkylamino,
[0047] R.sup.16 represents hydrogen, optionally cyano-, hydroxyl-,
halogen- or C.sub.1-C.sub.4-alkoxy-substituted
C.sub.1-C.sub.6-alkyl, in each case optionally cyano- or
halogen-substituted C.sub.3-C.sub.6-alkenyl or
C.sub.3-C.sub.6-alkynyl, or optionally cyano-, halogen- or
C.sub.1-C.sub.4-alkyl-substituted C.sub.3-C.sub.6-cycloalkyl,
[0048] R.sup.17 represents hydrogen, optionally cyano-, hydroxyl-,
halogen- or C.sub.1-C.sub.4-alkoxy-substituted
C.sub.1-C.sub.6-alkyl, in each case optionally cyano- or
halogen-substituted C.sub.3-C.sub.6-alkenyl or
C.sub.3-C.sub.6-alkynyl, optionally cyano-, halogen- or
C.sub.1-C.sub.4-alkyl-substituted C.sub.3-C.sub.6-cycloalkyl, or
optionally nitro-, cyano-, halogen-, C.sub.1-C.sub.4-alkyl-,
C.sub.1-C.sub.4-halogenoalkyl-, C.sub.1-C.sub.4-alkoxy- or
C.sub.1-C.sub.4-halogenoalkoxy-substituted phenyl, or together with
R.sup.16 represents in each case optionally
C.sub.1-C.sub.4-alkyl-substit- uted C.sub.2-C.sub.6-alkanediyl or
C.sub.2-C.sub.5-oxaalkanediyl.
[0049] X.sup.4 represents nitro, cyano, carboxyl, carbamoyl,
formyl, sulphamoyl, hydroxyl, amino, halogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy, and
[0050] X.sup.5 represents nitro, cyano, carboxyl, carbamoyl,
formyl, sulphamoyl, hydroxyl, amino, halogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl,
C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy,
[0051] where X.sup.4 is preferably located in position (2) and/or
(5)
[0052] ("active compounds of group 2").
[0053] 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.
[0054] Preferred meanings of the groups listed above in connection
with the formula (I) are defined below.
[0055] Q.sup.1 preferably represents O (oxygen) or S (sulphur).
[0056] Q.sup.2 preferably represents O (oxygen) or S (sulphur).
[0057] R.sup.1 preferably represents in each case optionally
cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted
methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 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-,
difluoromethoxy- or trifluoromethoxy-substituted phenyl,
phenylmethyl or phenylethyl, 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.
[0058] R.sup.2 represents 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.
[0059] R.sup.3 represents 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, propynylthio,
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, cyclobutylmethyl,
cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy,
cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,
cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio,
cyclobexylmethylthio, 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.
[0060] R.sup.4 preferably 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.
[0061] R.sup.3 and R.sup.4 together preferably represent
trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl)
or pentamethylene (pentane-1,5-diyl).
[0062] Q.sup.1 particularly preferably represents O (oxygen).
[0063] Q.sup.2 particularly preferably represents O (oxygen).
[0064] R.sup.1 particularly preferably represents in each case
optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted
methyl, ethyl, n- or i-propyl.
[0065] R.sup.2 particularly preferably represents fluorine,
chlorine, bromine or represents in each case optionally fluorine-,
chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or
i-propyl.
[0066] R.sup.3 particularly 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.
[0067] R.sup.4 particularly 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.
[0068] Most preferably, R.sup.1 and R.sup.2 represent methyl,
ethyl, n- or i-propyl.
[0069] Preferred active compound components of group 1 are in
particular also the sodium, potassium, magnesium, calcium,
ammonium, C.sub.1-C.sub.4-alkylammonium-,
di-(C.sub.1-C.sub.4-alkyl)ammonium-,
tri-(C.sub.1-C.sub.4-alkyl)ammonium,
tetra-(C.sub.1-C.sub.4-alkyl)ammoniu- m,
tri-(C.sub.1-C.sub.4-alkyl)sulphonium-, C.sub.5- or
C.sub.6-cycloalkylammonium and
di-(C.sub.1-C.sub.2-alkyl)-benzylammonium salts of compounds of the
formula (I) in which Q.sup.1, Q.sup.2, R.sup.1, R.sup.2, R.sup.3
and R.sup.4 have the meanings given above as being preferred.
[0070] 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.
1TABLE 1 (I) 9 Examples of compounds of the formula (I) Melting Ex.
No. Q.sup.1 Q.sup.2 R.sup.1 R.sup.2 R.sup.3 R.sup.4 point (.degree.
C.) I-1 O O CH.sub.3 CH.sub.3 OC.sub.2H.sub.5 CH.sub.3 163 I-2 O O
CH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 201 I-3 O O CH.sub.3 CH.sub.3
OC.sub.3H.sub.7-n CH.sub.3 156 I-4 O O CH.sub.3 CH.sub.3
OC.sub.3H.sub.7-i CH.sub.3 150 I-5 O O CH.sub.3 CH.sub.3 OCH.sub.3
10 218 I-6 O O CH.sub.3 CH.sub.3 OC.sub.2H.sub.5 11 170 I-7 O O
CH.sub.3 CH.sub.3 OC.sub.3H.sub.7-n 12 156 I-8 O O CH.sub.3
CH.sub.3 OC.sub.3H.sub.3-i 13 188 I-9 O O CH.sub.3 CH.sub.3 14 15
200 I-10 O O CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 178 I-11 O O
CH.sub.3 CH.sub.3 C.sub.2H.sub.5 CH.sub.3 161 I-12 O O CH.sub.3
CH.sub.3 SCH.sub.3 CH.sub.3 183 I-13 O O C.sub.2H.sub.5 CH.sub.3
OCH.sub.3 CH.sub.3 176 I-14 O O CH.sub.3 CH.sub.3 CH.sub.2OCH.sub.3
16 185 I-15 O O C.sub.2H.sub.5 CH.sub.3 OC.sub.2H.sub.5 CH.sub.3
172 I-16 O O C.sub.2H.sub.5 CH.sub.3 OCH.sub.3 17 173 I-17 O O
CH.sub.3 CH.sub.3 C.sub.2H.sub.5 OC.sub.2H.sub.5 183 I-18 O O
CH.sub.3 CH.sub.3 C.sub.2H.sub.5 18 175
[0071] Very particular emphasis as active compound components
according to the invention is also given to the sodium salts of the
compounds from Table 1.
[0072] Preferred meanings of the groups listed above in connection
with the compounds improving crop plant compatibility ("herbicide
safeners") of the formulae (Ia), (IIb), (IIc), (IId) and (IIe) are
defined below.
[0073] n preferably represents the numbers 0, 1, 2, 3 or 4.
[0074] A.sup.2 preferably represents in each case optionally
methyl-, ethyl-, methoxycarbonyl- or ethoxycarbonyl-substituted
methylene or ethylene.
[0075] R.sup.5 preferably 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.
[0076] R.sup.6 preferably 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.
[0077] R.sup.7 preferably represents in each case optionally
fluorine-, chlorine- and/or bromine-substituted methyl, ethyl, n-
or i-propyl.
[0078] R.sup.8 preferably 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.
[0079] R.sup.9 preferably 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-, 30 i-, s- or t-butyl-substituted phenyl, or
together with R.sup.8 represents one of the radicals
--CH.sub.2--O--CH.sub.2-CH.sub.2-- and
--CH.sub.2-CH.sub.2--O--CH.sub.2-CH.sub.2--, 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.
[0080] R.sup.10 preferably 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.
[0081] R.sup.11 preferably 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.
[0082] R.sup.12 preferably 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.
[0083] X.sup.1 preferably 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.
[0084] X.sup.2 preferably 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.
[0085] X.sup.3 preferably 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.
[0086] R.sup.13 preferably represents hydrogen, methyl, ethyl, n-
or i-propyl.
[0087] R.sup.14 preferably represents hydrogen, methyl, ethyl, n-
or i-propyl.
[0088] R.sup.15 preferably 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.
[0089] R.sup.16 preferably 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.
[0090] R.sup.17 preferably 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 propenyl, 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 R.sup.16
represents 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.
[0091] X.sup.4 preferably 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.
[0092] X.sup.5 preferably 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.
[0093] 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.
[0094] Table 2: Examples of the compounds of the formula (IIa)
2 (IIa) 19 Example No. (positions) (X.sup.1).sub.n A.sup.1 R.sup.5
IIa-1 (2) Cl, (4) Cl 20 OCH.sub.3 IIa-2 (2) Cl, (4) Cl 21 OCH.sub.3
IIa-3 (2) Cl, (4) Cl 22 OC.sub.2H.sub.5 IIa-4 (2) Cl, (4) Cl 23
OC.sub.2H.sub.5 IIa-5 (2) Cl 24 OCH.sub.3 IIa-6 (2) Cl, (4) Cl 25
OCH.sub.3 IIa-7 (2) F 26 OCH.sub.3 IIa-8 (2) F 27 OCH.sub.3 IIa-9
(2) Cl, (4) Cl 28 OC.sub.2H.sub.5 IIa-10 (2) Cl, (4) CF.sub.3 29
OCH.sub.3 IIa-11 (2) Cl 30 OCH.sub.3 IIa-12 -- 31 OC.sub.2H.sub.5
IIa-13 (2) Cl, (4) Cl 32 OC.sub.2H.sub.5 IIa-14 (2) Cl, (4) Cl 33
OC.sub.2H.sub.5 IIa-15 (2) Cl, (4) Cl 34 OC.sub.2H.sub.5 IIa-16 (2)
Cl, (4) Cl 35 OC.sub.2H.sub.5 IIa-17 (2) Cl, (4) Cl 36
OC.sub.2H.sub.5
[0095] 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.
3TABLE 3 (IIb) 37 Examples of compounds of the formula (IIb)
Example No. (position) X.sup.2 (position) X.sup.3 A.sup.2 R.sup.6
IIb-1 (5) Cl -- CH.sub.2 OH IIb-2 (5) Cl -- CH.sub.2 OCH.sub.2
IIb-3 (5) Cl -- CH.sub.2 OC.sub.2H.sub.5 IIb-4 (5) Cl -- CH.sub.2
OC.sub.3H.sub.7-n IIb-5 (5) Cl -- CH.sub.2 OC.sub.3H.sub.7-i IIb-6
(5) Cl -- CH.sub.2 OC.sub.4H.sub.9-n IIb-7 (5) Cl -- CH.sub.2
OCH(CH.sub.3)C.sub.5H.sub.11-n IIb-8 (5) Cl (2) F CH.sub.2 OH IIb-9
(5) Cl (2) Cl CH.sub.2 OH IIb-10 (5) Cl -- CH.sub.2
OCH.sub.2CH.dbd.CH.sub.2 IIb-11 (5) Cl -- CH.sub.2
OC.sub.4H.sub.9-i IIb-12 (5) Cl -- CH.sub.2 38 IIb-13 (5) Cl -- 39
OCH.sub.2CH.dbd.CH.sub.2 IIb-14 (5) Cl -- 40 OC.sub.2H.sub.5
[0096] Examples of the compounds (IIc) which are very particularly
preferred as herbicide safeners according to the invention are
listed in Table 4 below.
4TABLE 4 (IIc) 41 Examples of the compounds of the formula (IIc)
Example No. R.sup.7 N(R.sup.8R.sup.9) IIc-1 CHCl.sub.2
N(CH.sub.2CH.dbd.CH.sub.2).sub.2 IIc-2 CHCl.sub.2 42 IIc-3
CHCl.sub.2 43 IIc-4 CHCl.sub.2 44 IIc-5 CHCl.sub.2 45 IIc-6
CHCl.sub.2 46 IIc-7 CHCl.sub.2 47
[0097] 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.
5TABLE 5 (IId) 48 Examples of the compounds of the formula (IId)
Example (positions) (positions) No. R.sup.13 R.sup.14 R.sup.15
(X.sup.4).sub.n (X.sup.5).sub.n IId-1 H H CH.sub.3 (2) OCH.sub.3 --
IId-2 H H C.sub.2H.sub.5 (2) OCH.sub.3 -- IId-3 H H
C.sub.3H.sub.7-n (2) OCH.sub.3 -- IId-4 H H C.sub.3H.sub.7-i (2)
OCH.sub.3 -- IId-5 H H 49 (2) OCH.sub.3 -- IId-6 H H CH.sub.3 (2)
OCH.sub.3 (5) CH.sub.3 -- IId-7 H H C.sub.2H.sub.5 (2) OCH.sub.3
(5) CH.sub.3 -- IId-8 H H C.sub.3H.sub.7-n (2) OCH.sub.3 (5)
CH.sub.3 -- IId-9 H H C.sub.3H.sub.7-i (2) OCH.sub.3 (5) CH.sub.3
-- IId-10 H H 50 (2) OCH.sub.3 (5) CH.sub.3 -- IId-11 H H OCH.sub.3
(2) OCH.sub.3 (5) CH.sub.3 -- IId-12 H H OC.sub.2H.sub.5 (2)
OCH.sub.3 (5) CH.sub.3 -- lId-13 H H OC.sub.3H.sub.7-i (2)
OCH.sub.3 (5) CH.sub.3 -- IId-14 H H SCH.sub.3 (2) OCH.sub.3 (5)
CH.sub.3 -- IId-15 H H SC.sub.2H.sub.5 (2) OCH.sub.3 (5) CH.sub.3
-- IId-16 H H SC.sub.3H.sub.7-i (2) OCH.sub.3 (5) CH.sub.3 --
Ild-17 H H NHCH.sub.3 (2) OCH.sub.3 (5) CH.sub.3 -- lId-18 H H
NHC.sub.2H.sub.5 (2) OCH.sub.3 (5) CH.sub.3 -- IId-19 H H
NHC.sub.3H.sub.7-i (2) OCH.sub.3 (5) CH.sub.3 -- IId-20 H H 51 (2)
OCH.sub.3 (5) CH.sub.3 -- IId-21 H H NHCH.sub.3 (2) OCH.sub.3 --
IId-22 H H NHC.sub.3H.sub.7-i (2) OCH.sub.3 -- IId-23 H H
N(CH.sub.3).sub.2 (2) OCH.sub.3 -- IId-24 H H N(CH.sub.3).sub.2 (2)
OCH.sub.3 (5) CH.sub.3 -- IId-25 H H CH.sub.2OCH.sub.3 (2)
OCH.sub.3 -- IId-26 H H CH.sub.2OCH.sub.3 (2) OCH.sub.3 (5)
CH.sub.3 --
[0098] 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.
6TABLE 6 (IIe) 52 Examples of the compounds of the formula (IIe)
Example (positions) (positions) No. R.sup.13 R.sup.16 R.sup.17
(X.sup.4).sub.n (X.sup.5).sub.n IIe-1 H H CH.sub.3 (2) OCH.sub.3 --
IIe-2 H H C.sub.2H.sub.5 (2) OCH.sub.3 -- IIe-3 H H
C.sub.3H.sub.7-n (2) OCH.sub.3 -- IIe-4 H H C.sub.3H.sub.7-i (2)
OCH.sub.3 -- IIe-5 H H 53 (2) OCH.sub.3 -- IIe-6 H CH.sub.3
CH.sub.3 (2) OCH.sub.3 -- IIe-7 H H CH.sub.3 (2) OCH.sub.3 -- (5)
CH.sub.3 IIe-8 H H C.sub.2H.sub.5 (2) OCH.sub.3 -- (5) CH.sub.3
IIe-9 H H C.sub.3H.sub.7-n (2) OCH.sub.3 -- (5) CH.sub.3 IIe-10 H H
C.sub.3H.sub.7-i (2) OCH.sub.3 -- (5) CH.sub.3 IIe-11 H H 54 (2)
OCH.sub.3 (5) CH.sub.3 -- IIe-12 H CH.sub.3 CH.sub.3 (2) OCH.sub.3
-- (5) CH.sub.3 IIe-13 H H CH.sub.2CH.dbd.CH.sub.2 (2) OCH.sub.3 --
IIe-14 H H CH.sub.2CH.dbd.CH.sub.2 (2) OCH.sub.3 -- (5) CH.sub.3
IIe-15 H H 55 (2) OCH.sub.3 -- IIe-16 H H 56 (2) OCH.sub.3 (5)
CH.sub.3 -- Ile-17 H H 57 (2) OCH.sub.3 -- IIe-18 H H 58 (2)
OCH.sub.3 (5) CH.sub.3 -- IIe-19 H H 59 (2) OCH.sub.3 -- IIe-20 H H
60 (2) OCH.sub.3 (5) CH.sub.3 --
[0099] 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).
[0100] 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).
[0101] The compounds of the general formula (IIc) 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).
[0102] 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-19621522/U.S. Pat. No.
6,235,680/WO 97/45016).
[0103] 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).
[0104] 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.
7TABLE 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
[0105] Surprisingly, it has now been found that the above-defined
active compound combinations of substituted
thien-3-ylsulphonylamino(thio)carbon- yltriazolin(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.
[0106] 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)carbonyltri- azolin(ethi)ones on the
crop plants virtually completely without negatively affecting the
herbicidal activity with respect to the weeds.
[0107] 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.
[0108] The active compound combinations according to the invention
can be used, for example, in connection with the following
plants:
[0109] 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, Lindernia, Lamium, Veronica, Abutilon,
Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,
Ranunculus, Taraxacum.
[0110] Dicotyledonous crops of the genera: Gossypium, Glycine,
Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia,
Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis,
Cuburbita, Helianthus.
[0111] 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.
[0112] Monocotyledonous crops of the genera: Oryza, Zea, Triticum,
Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas,
Asparagus, Allium.
[0113] 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.
[0114] 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.
[0115] The active compounds or active compound combinations can be
converted into the customary formulations, such as solutions,
emulsions, wettable powders, suspensions, powders, dusting agents,
pastes, soluble powders, granules, suspoemulsion concentrates,
natural and synthetic materials impregnated with active compound,
and very fine capsules in polymeric substances.
[0116] 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.
[0117] 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.
[0118] Suitable solid carriers are:
[0119] 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.
[0120] 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.
[0121] 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 phthalocyanine dyestuffs, and trace nutrients such as salts
of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
[0122] 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%.
[0123] 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.
[0124] 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.
[0125] 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.
[0126] 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.
[0127] 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
[0128] 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
[0129] Post-Emergence Test
[0130] 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.
[0131] 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.
[0132] The figures denote:
[0133] 0%=no damage (like untreated control)
[0134] 100%=total destruction/damage
[0135] 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:
[0136] maize=maize cv. "Pioneer"
[0137] a.i.=active ingredient=active compound/safener
8TABLE 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
[0138] Post-Emergence Test
[0139] Here, an aqueous spray liquor comprising 0.5% of the
additive Renex-36 was prepared.
[0140] Ex. No. I-2, sodium salt= 61
[0141] Ex.-No. IId-25= 62
9TABLE A-2-1 Post-emergence test/greenhouse Damage winter Active
compound Application rate barley (+ safener) (g of a.i./ha) (in %)
I-2, sodium salt 4 60 2 50 I-2, sodium salt + 4 + 100 50 Comp. No.
IId-25 2 + 100 25 .sup. 4 + 30 50 .sup. 2 + 30 35
[0142]
10TABLE 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
[0143] Post-Emergence Test
[0144] The compound I-2 was used as 10 WP. In each case,
Marlipal.RTM. was added in an amount of 500 ml/ha.
[0145] Evaluation was carried out as early as 7 days after the
application.
[0146] Maize 1=maize of the cultivar "Prinz"
[0147] Maize 2=maize of the cultivar "Pioneer"
[0148] Maize 3=maize of the cultivar "LIXIS"
11TABLE 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
[0149]
12TABLE 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
[0150]
13TABLE A-3-3 Post-emergence test/greenhouse Application rate
Damage Active compound (+ safener) (g of a.i./ha) Maize 3 (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
[0151] Post-Emergence Test
[0152] Mefenpyr-diethyl was used as 100 EC.
[0153] The compounds of Ex. Nos. I-2 and I-13 were used as 10
WP.
14TABLE A-4-1 Post-emergence test/greenhouse Application rate
Damage winter Safener (g of a.i./ha) wheat (in %) mefenpyr-diethyl
50 0
[0154]
15TABLE A-4-2 Post-emergence test/greenhouse Application rate
Damage 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
[0155]
16TABLE A-4-3 Post-emergence test/greenhouse Damage winter
Application rate wheat Active compound (+ safener) (g of a.i./ha)
(in %) I-13 125 30 60 20 I-13 + mefenpyr-diethyl 125 + 50 10 60 +
50 5
[0156]
17TABLE A-4-4 Post-emergence test/greenhouse Damage winter
Application rate wheat Safener (g of a.i./ha) (in %)
mefenpyr-diethyl 50 0
[0157]
18TABLE A-4-5 Post-emergence test/greenhouse Damage winter
Application rate barley Active compound (+ safener) (g of a.i./ha)
(in %) I-2 30 80 15 70 8 50 I-2 + mefenpyr-diethyl 30 + 50 70 15 +
50 40 8 + 50 30
[0158]
19TABLE A-4-6 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) barley (in
%) I-13 125 80 60 70 30 50 I-13 + mefenpyr-diethyl 125 + 50 60 60 +
50 50 30 + 50 30
Example A-5
[0159] Post-Emergence Test
[0160] Mefenpyr-diethyl was used as 100 EC and the compound of Ex.
No. I-2 was used as 10 WP.
20TABLE A-5-1 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) wheat (in
%) I-2 30 60 mefenpyr-diethyl 50 0 I-2 + mefenpyr-diethyl 30 + 50
5
[0161]
21TABLE A-5-2 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) wheat (in
%) I-13 125 50 mefenpyr-diethyl 50 0 I-13 + mefenpyr-diethyl 125 +
50 10
[0162]
22TABLE A-5-3 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) wheat (in
%) I-15 60 80 mefenpyr-diethyl 50 0 I-15 + mefenpyr-diethyl 60 + 50
40
[0163]
23TABLE A-5-4 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) wheat (in
%) I-16 60 25 mefenpyr-diethyl 50 0 I-16 + mefenpyr-diethyl 60 + 50
15
[0164]
24TABLE A-5-5 Post-emergence test/greenhouse Application rate
Damage winter Safener (g of a.i./ha) wheat (in %) mefenpyr-diethyl
50 0
[0165]
25TABLE A-5-6 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) wheat (in
%) I-2 30 40 15 30 8 20 I-2 + mefenpyr-diethyl 30 + 50 20 15 + 50
10 8 + 50 10
[0166]
26TABLE A-5-7 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) wheat (in
%) I-17 30 70 15 50 8 40 I-17 + mefenpyr-diethyl 30 + 50 40 15 + 50
30 8 + 50 20
[0167]
27TABLE A-5-8 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) wheat (in
%) I-14 1 40 0.5 20 I-14 + mefenpyr-diethyl 1 + 50 30 0.5 + 50
10
[0168]
28TABLE A-5-9 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) wheat (in
%) I-18 2 50 1 30 I-18 + mefenpyr-diethyl 2 + 50 20 1 + 50 10
[0169]
29TABLE A-5-10 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) wheat (in
%) I-15 30 70 15 40 8 30 I-15 + mefenpyr-diethyl 30 + 50 10 15 + 50
0 8 + 50 0
[0170]
30TABLE A-5-11 Post-emergence test/greenhouse Application rate
Damage winter Safener (g of a.i./ha) barley (in %) mefenpyr-diethyl
50 0
[0171]
31TABLE A-5-12 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ 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
[0172]
32TABLE A-5-13 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) barley (in
%) I-17 30 80 15 70 8 70 I-17 + mefenpyr-diethyl 30 + 50 70 15 + 50
60 8 + 50 20
[0173]
33TABLE A-5-14 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) barley (in
%) I-14 0.5 30 0.25 10 I-14 + mefenpyr-diethyl 0.5 + 50 20 0.25 +
50 0
[0174]
34TABLE A-5-15 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) barley (in
%) I-18 2 60 1 20 0.5 10 I-18 + mefenpyr-diethyl 2 + 50 20 1 + 50
10 0.5 + 50 0
[0175]
35TABLE A-5-19 Post-emergence test/greenhouse Application rate
Damage winter Active compound (+ safener) (g of a.i./ha) barley (in
%) I-15 30 80 15 70 8 60 I-15 + mefenpyr-diethyl 30 + 50 30 15 + 50
20 8 + 50 10
* * * * *