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Herbicides based on carbamoyltriazolinones
The invention relates to new herbicidal, synergistic active compound combinations
5 composed of known carbamoyltriazolinones on the one hand and of known, herbicidally active compounds on the other hand and which can be used particularly successfully for controlling weeds.
Carbamoyltriazolinones, being broad-range herbicides, are the subject-matter of a
10 series of patent applications (cf. EP-A 294 666, EP-A 370 293, EP-A 391 187, EP-A 398 096, EP-A 399 294, EP-A 415 196, EP-A 477 646). However, the known carbamoyltriazolinones show a series of gaps with regard to their action.
A series of herbicidal active compound combinations based on N-aryl-uracils has
15 also been disclosed already (cf. DE-A-19 635 060, DE-A-19 635 074). Again, however, the properties of these active compound concentrations are not satisfactory in all respects.
Surprisingly, it has now been found that a series of known active compounds from
20 the carbamoyltriazolinone series, used jointly with known herbicidally active compounds from various classes of substances, show pronounced synergistic effects with regard to the action against weeds and can be employed especially advantageously as broad-range combination products for controlling monocotyledonous and dicotyledonous weeds in crops of useful plants such as, for
25 example, in barley, maize, rice, soya beans, sunflowers, wheat and sugar cane, but also for the semi- and nonselective control of monocotyledonous and dicotyledonous weeds.
The invention relates to herbicidal compositions, characterized by an effective 30 content of an active compound combination comprising
(a) a carbamoyltriazolinone of the general formula (1)
RI represents hydrogen, hydroxyl, amino, or in each case optionally
substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylamino, alkenylamino, alkinylamino, alkylideneamino, dialkylamino, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R2 represents in each case optionally substituted alkyl, alkenyl, alkinyl,
alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio,
alkylamino, alkenylamino, alkinylamino, dialkylamino, cycloalkyl,
cycloalkyloxy, cycloalkylalkyl, aryl, aryloxy, arylthio, arylamino or
15 arylalkyl, and
R3 represents in each case optionally substituted alkyl, alkenyl, alkinyl,
cycloalkyl, cycloalkylalkyl, arylalkyl, arylalkenyl or arylalkinyl;
20 ("active compounds of group 1")
(b) one or more compounds from a second group of herbicides containing the
25 active compounds mentioned hereinbelow:
sodium 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitrobenzoate (acitluorfen-
sodium), 1H-1,2,4-triazol-3-amine (amitrole), 2-[2,4-dichloro-5-(2-propinvloxy)-
pheny1]-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]-pyridin-3(2H)-one (azafeni din),
N-(4,6-dimethoxy-pyrimidin-2-y1)-N41-methy1-4-(2-methy1-2H-tetrazol-5-y1)-1H-pyrazol-5-ylsulphonyl]urea (azimsulfuron), N-benzyl-2-(4-fluoro-3-trifluoromethyl-phenoxy)-butanamide (beflubutamid), 4-chloro-2-oxo-3(2H)-benzothiazoleacetic
5 acid (benazolin), N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethyl-benzenamine
methylsulphony1)-urea (bensulfuron), methyl 21244-(3,6-dihydro-3-methy1-2,6- dioxo-4-trifluoromethy1-1(2H)-pyritnidinylphenoxymethyl]-5-ethyl-phenoxy-prop-
anoate (benzfendizone), 3-(2-chloro-4-methylsulfonyl-ben zoy1)-4-phenylthio-
10 bicyclo-[3.2.1]-oct-3-en-2-one (benzobicyclon), ethyl N-benzoyl-N-(3,4-dichloro¬pheny1)-DL-alaninate (benzoylprop-ethyl), [1,1-dimethy1-2-oxo-2-(2-propenyloxy)1- ethyl 2-chloro-5-(3,6-dihydro-3-methy1-2,6-dioxo-4-trifluoromethy1-1(2H)- pyrimidiny1)-benzoate (butafenacil-allyl), 2-(1-ethoximino-propy1)-3-hydroxy-5- [2,4,6-trimethyl-3-(1-oxo-buty1)-phenyl]-2-cyclohexen-1-one (butroxydim), N,N-
1 5 di eth y1-3-(2,4,6-trimethyl-phenylsul fony1)- 1 H- 1 ,2,4-tri azole- 1-carboxami de (cafen-strole), 24 1 4(3-chloro-2-propeny1)-ox y-i mino]-propy1]-3-hydroxy-5-(tetrahydro-2H-pyran-4-y1)-2-cyclohexen-l-one (caloxydim, tepraloxydim), N44-chloro-6-methoxy-
ethyl 2-chloro-3-[2-chl oro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindo1-2-y1)-
20 phen y1]-2-propanoate (cinidon-ethyl), 2-[112-(4-chloro-phenoxy)- propoxyaminobuty11-5-(tetrahydro-2H-thiopyran-3-y1)-1,3-cyclohexanedi one (clef¬oxydim), (E,E)-(+)-2-[1-[[(3-chloro-2-propeny1)-oxy]-imino]-propyl]-3-hydroxy-2- cyclohexen-l-one (clethodim), 2-(1-ethoximinobuty1)-3-hydroxy-5-(tetrahydro-2H¬thiopyran-3-y1)-2-cyclohexen- 1 -one (cycloxydim), butyl (R)-2-[4-(4-cyano-2-fluoro-
25 phenoxy)-phenoxy]-propanoate (cyhalofop-butyl), N-(2,6-dichloro-phenyl)-5-ethoxy¬7-fluoro-[ 1,2,41-triazolo-[1,5-c] -pyri midi ne-2-sul phonamide (diclosulam), 2414(3,5- di fluoro-pheny1)-amino-carbonyl-hydrazono]-ethyl j-pyridl ne-3-carboxylic acid (di¬n ufenzopyr), S-(1-methyl-l-phenyl-ethyl) 1-piperidine-carbothioate (di mepiperate), (S)-2-chloro-N-(2,4-dimethy1-3-thieny1)-N-(2-methoxy-1-methyl-ethyl)-acetamide tdimethenamid-P), 2-12-(3-chloro-pheny1)-oxiranylmethy11-2-ethy1-111-indene-
1.3(2H)-dione (epropodan). (R)-ethyl 214-(6-chloro-benzoxazol-2-yl-oxy)-
phenoxy)-propanoate (fenoxaprop-P-ethyl), 4-(2-chloro-pheny1)-N-cyclohexyl-N-ethy1-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide (fentrazamide), N-(2,6-
difluoro-phenyl)-8-fluoro-5-methoxyt 1,2,4]-triazolo-[1,5-c]-pyrimidine-2- sulphonamide (florasulam), butyl (R)-2-[4-(5-trifluoromethyl-pyridin-2-yl-oxy)-
5 phenoxy]-propanoate (fluazifop, -butyl, -P-butyl), i-propyl 5-(4-bromo-1-methy1-5- trifluoromethy1-1H-pyrazol-3-y1)-2-chloro-4-fluoro-benzoate (fluazolate), the sodium salt of 4,5-dihydro-3-methoxy-4-methy1-5-oxo-N-[(2-trifluoromethoxy-pheny1)- sulphonyl]-1-H-1,2,4-triazole-1-carboxamide (flucarbazone-sodium), ethyl [2-chloro¬4-fluoro-5-(5-methy1-6-oxo-4-trifluoromethy1-1(6H)-pyridaziny1)-phenoxyl-acetate
10 (flufenpyr), 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propiny1)-2H-1,4-benzoxazin-6-yl]-
4,5,6,7-tetrahydro-1H-isoindole-1,3-dione (flumioxaztn), 244-chloro-2-fluoro-5-[(1- methy1-2-propiny1)-oxy]-phenyl]-4,5,6,7-tetrahydro-M-isoindole-1,3(2H)-dione
pyrrolidinone (fluorochloridone), the sodium salt of N-(4,6-dimethoxy-pyrimidin-2-
methylsulfony1-2-nitro-benzamide (fomesafen), 2-[[[[(4,6-dimethoxy-2-pyrimidiny1)-
amino]-carbonyl]-amino]-sulphonyl]-4-formylamino-N,N-dimethyl-benzamide (foramsulfuron), (R)-244-(3-chloro-5-trifluoromethyl-pyridin-2-yl-oxy)-phenoxyl-
20 propanoic acid (and its methyl, -2-ethoxy-ethyl and butyl esters) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), the sodium salt of N-(4-methoxy-6-methy1-1,3,5- triazin-2-y1)-N'-(5-iodo-2-methoxycarbonyl-phenylsulphony1)-urea (iodosulfuron-methyl-sodium), (4-chloro-2-methylsulphonyl-pheny1)-(5-cyclopropyl-isoxazol-4-y1)- methanone (isoxachlortole), 2424413,5-dichloro-2-pyridiny1)-oxy]-phenoxy]-1-oxo-
25 propyll-isoxazolidine (isoxapyrifop), (2-ethoxy-l-methyl-2-oxo-ethyl) 5-(2-chloro-4-
trifluoromethyl-phenoxy)-2-nitro-benzoate (1 actofen), 2-(2-benzothiazolyloxy)-N-
meth)l-N-phenyl-acctamide (mcfenacet), methyl 2-I[R(4,6-dimethoxy-2-
pyn mi di ny1)-ami no -carbonyl 1 -ami no]-sul phony1]-44 [( methyl su 1phony1)-ami no]-
met h■11-benzoate ( mesosulfuron), 2-(4 -methylsulphony1-2-nitro-benzoy1)-1,3-
30 cyclohexancdionc (mcsotrionc). 4-amino-3-methyl-6-phenyl-1.2.4-triazin-5(4H)-one
(mctamitron). (.5 )-2-chloro-N-(2-ethy1-6-methyl-pheny1)-N-(2-methoxy-1-methyl-
ethyl)-acetamide (S-metolachlor), S-(2-chloro-benzyl) N,N-diethyl-thiocarbamate
(orbencarb), 4-dipropylamino-3,5-dinitro-benzenesulphonamide (oryzalin), 342,4-
5 2(3H)-one (oxadiazon), 341-(3,5-dichloro-pheny1)-1-i-propyl]-2,3-dihydro-6-methy1-
5-pheny1-4H-1,3-oxazin-4-one (oxaziclomefone), 2-chloro-1-(3-ethoxy-4-nitro-
phenoxy)-4-trifluoromethyl-benzene (oxyfluorfen), 2-(2,2-difluoro-ethoxy)-N-(5,8- dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-y1)-6-trifluoromethyl-benzenesulphonamide (penoxsulam), 2-chloro-N-(2-ethoxy-ethyl)-N-(2-methyl-1-
10 phenyl-1-propeny1)-acetamide (pethoxamid), N44-fluoro-pheny1)-6-(3-
trifluoromethyl-phenoxy)-pyridine-2-carboxamide (picolinafen), 1-chloro-N42-
chloro-4-fluoro-5-[(6S,7aR)-6-fluoro-tetrahydro-1,3-dioxo-1H-pyrrolo[1,2-climid-azol-2(3H)-y1]-phenyl]-methanesulphonamide (profluazol), N-(3,4-dichloro-pheny1)- propanamide (propanil), (R)-[2-[[(1-methyl-ethylidene)-amino]-oxy]-ethyl] 2-[4-(6-
15 chloro-2-quinoxalinyloxy)-phenoxy]-propanoate (propaquizafop), 2-chloro-N-(2- ethy1-6-methyl-pheny1)-N-[(1-methyl-ethoxy)-methyl]-acetamide (propisochlor), the sodium salt of methyl 2-[[[(4,5-dihydro-4-methy1-5-oxo-3-propoxy-1H-1,2,4-triazol-1-y1)-carbony1]-amino]-sulfonyl]-benzoate (procarbazone-sodium), 1-(3-chloro¬4,5 ,6,7-tetrahydro-pyrazolo[1,5-a]pyridin-2-y1)-5-(methy1-2-propinylamino)-1H-
20 pyrazole-4-carbonitrile (pyrazogyl), diphenylmethanone O-[2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoyl]-oxime (pyribenzoxim), 6-chloro-3-phenyl-pyridazin-4- ol (pyridatol), 7-[(4,6-dimethoxy-2-pyrimidiny1)-thi o)-3-methy1-1(3H)- i sobenzofuranone (pyriftalide), methyl 2-(4,6-dimethoxy-pyri mi din-2-yl-oxy)- benzoate (pyriminobac-methyl), sodium 2-chloro-6-(4,6-dimethoxy-pyrimidin-2-
25 ylthio)-benzoate (pyrithi obac-sodium), 3,7-di chloro-quinolin-8-carbox ylic acid
(quinchlorac), 244-(6-chloro-2-quinoxalinyloxy)-phenoxy]-propanoic acid (and its ethyl and tetrahydro-2-furanyl-methyl esters) (quizalofop, -ethyl, -P-ethyl, -P-tcfuryl),
2-(1-ethoximinobuty1)-5-(2-ethylthiopropy1)-3-hydrox y-2-cyc lohexen-I -one (sethoxydim), methyl 2-difluoromethy1-5-(4,5-dihydro-thiazol-2-■,.1)-4-(2-methyl-
30 propy1)-6-tri fl uorome thyl - pyri dine-3-ca rbox yl ate (thiazopyr), t 3.6.64 Tic hloro )-
pyridin-2-yl-oxy-acetic acid (triclopyr), the sodium salt of N-[[(4.6-dimethoxy-2-
pyrimidiny1)-amino}-carbony11-3-(2,2,2-trifluoro-ethoxy)-2-pyridinesulphonamide (trifloxysulfuron), N-[4-dimethylamino-6-(2,2,2-trifluoro-ethoxy)-1,3,5-triazin-2-y1]- N'-(2-methoxycarbonyl-phenylsulphony1)-urea (triflusulfuron-methyl), N-(4-
5 sulphonyl)-urea (tritosulfuron), N-[[(4,6-dimethoxy-2-pyrimidiny1)-amino]-
carbony1]-3-(N-methyl-N-methylsulphonyl-aminop-2-pyridinesulphonamide (cf. WO-A-92/10660), methyl 2-[[[[(4,6-dimethoxy-2-pyrimidiny1)-amino]-carbonyl]- aminol-sulphony1]-4-[[(methylsulphony1)-amino]methyll-benzoate (cf. DE-A¬43 35 297), 444,5-dihydro-4-methy1-5-oxo-(3-trifluoromethyl)-1H-1,2,4-triazol-1-
10 y1]-2-[(ethylsulphonyl)amino]-5-fluoro-benzenecarbothioamide (cf. WO-A-
("active compounds of group 2"),
15 and, if appropriate,
(c) a compound which improves crop plant tolerance, from amongst the following
group of compounds:
20 4-dichloroacety1-1-oxa-4-aza-spiro[4.5]-decane (AD-67), 1-dichloroacetyl-
hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-one (dicyclonon, BAS-145138), 4-dichloroacety1-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1- methyl-hexyl 5-chloro-quinoxalin-8-oxy-acetate (cloquintocet-mexyl), a-(cyano-methoximino)-phenylacetonitrile (cyometrinil), 2,2-dichloro-N-(2-oxo-2-(2-
25 propenylamino)-ethyl)-N-(2-propenyl)-acetamide (DKA-24), 2,2-dichloro-N,N-di-2-
propenyl-acetamide (dichlormid), N-(4-methyl-phenyl)-N'-(1-methyl-1-phenyl¬ethyl)-urea (dymron), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), ethyl 142.4- dich loro-pheny1)-5-trichloromethy1-1 H-1.2,4-tri azole-3-carboxylate (fench lorazol¬ethyl), phenylmethyl 2-chloro-4-tnfluoromethyl-thiazole-5-carboxylate (flurazole), 4-
30 chloro-N-(1,3-dioxolan-2-yl-methoxy)-a-tntluoro-acetophenone oxime (fluxofemm).
3-dichloroacety1-5-(2-furany1)-2.2-dirncthyl-oxazolidine (furilazole, MON-139(X)).
ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifen-ethyl), diethyl-1- (2,4-dichloropheny1)-4,5-di hydro-5-methyl-1H-pyrazole-3,5-dic arboxyl ate (mefenpyr-diethyl) 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 1,8- naphthalenedicarboxylic anhydride, a-(1,3-dioxolan-2-yl-methoximino)-
5 phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2- propeny1)-acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R¬28725), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), methyl 1-(2-chlOro¬pheny1)-5-pheny1-1H-pyrazole-3-carboxyl ate and N-(2-methoxy-benzoy1)-4- [ (methyl amino-carbony1)-ami no]-benzene sulphonamide
("active compounds of group 3").
Preferred meanings of the radicals mentioned in the above formula (I) are illustrated hereinbelow.
RI preferably represents hydrogen, hydroxyl, amino, or represents alkyl, alkenyl,
alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylamino, alkenylamino,
alkinylamino, alkylideneamino or dialkylamino, each of which has up to 6
carbon atoms and each of which is optionally substituted by halogen or cyano,
20 or represents cycloalkyl, cycloalkylalkyl, each of which has 3 to 6 carbon atoms in the cycloalkyl groups and, if appropriate, 1 to 4 carbon atoms in the alkyl group and each of which is optionally substituted by halogen, cyano or CI-Ca-alkyl, or represents phenyl or phenyl-C1-C4-alkyl, each of which is optionally substituted by halogen, cyano, CI-Ca-alkyl or C1-C4-alkoxy.
preferably represents alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio. alkenylthio, alkinylthio, alkylamino, alkenylamino, alkinylamino or dialkylamino, each of which has up to 6 carbon atoms and each of which is optionally substituted by halogen, cyano, C,-C4-alkoxy or C1-C4-alkylthio, or
30 represents cycloalkyl. cycloalkyloxy or cycloalkylalkyl, each of which has 3
to 6 carbon atoms in the cycloalkyl groups and, if appropriate, 1 to 4 carbon
atoms in the alkyl group and each of which is optionally substituted by halogen, cyano or CI-Ca-alkyl, or represents phenyl, phenoxy, phenylthio, phenylamino or phenyl-C1-Ca-alkyl, each of which is optionally substituted by halogen, cyano, C1-Ca-alkyl or CI-Ca-alkoxy.
R3 preferably represents alkyl, alkenyl or alkinyl, each of which has up to 10
carbon atoms and each of which is optionally substituted by halogen, cyano,
C1-Ca-alkoxy, C1-Ca-alkylthio, C1-Ca-alkylsulphinyl, C1-Ca-alkylsulphonyl,
C1-Ca-alkylamino or di-(CI-Ca-alkyl)amino, or represents cycloalkyl or
10 cycloalkylalkyl, each of which has 3 to 6 carbon atoms in the cycloalkyl moiety and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by halogen, cyano or CI-Ca-alkyl, or represents phenyl-C1-C6-alkyl, phenyl-C2-C6-alkenyl or phenyl-C2-C6-alkinyl, each of which is optionally substituted by halogen, cyano, C1-Ca-alkyl or C1-Ca-
RI especially preferably represents hydrogen, hydroxyl, amino, or represents
methyl, ethyl, n- or i-propyl, n-, s- or t-butyl, propenyl, butenyl, propinyl or
butinyl, methoxy, ethoxy, n- or i-propoxy, n-, s- or t-butoxy, propenyloxy,
20 butenyloxy, propinyloxy or butinyloxy, methylamino, ethylamino, n- or i-
propylamino, n-, s- or t-butylamino, propenylamino, butenylam- ino, propinylamino or butinylamino, ethylideneamino, propylideneamino, butylideneamino, dimethylamino or diethylamino, each of which is optionally substituted by fluorine, chlorine or cyano, or represents cyclopropyl,
25 cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, or represents phenyl or benzyl, each of which is optionally substituted by fluorine. chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, s- or t-
30 hutvl. methoxy or ethoxy.
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- 10 -
fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, s- or t-
butyl, methoxy or ethoxy.
RI very especially preferably represents hydrogen, amino, or represents methyl,
5 ethyl, n- or i-propyl, propenyl, butenyl, propinyl or butinyl, methoxy, ethoxy,
n- or i-propoxy, propenyloxy or propinyloxy, each of which is optionally substituted by fluorine or chlorine, or represents methylamino, ethylamino, n¬or i-propylamino, propenylamino or propinylamino, dimethylamino or diethylamino, or represents cyclopropyl or cyclopropylmethyl, each of which
10 is optionally substituted by fluorine, chlorine, cyano or methyl.
very especially preferably represents methyl, ethyl, n- or i-propyl, n-, s- or
t-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-
propoxy, n-, s- or t-butoxy, propenyloxy, butenyloxy, propinyloxy,
15 butinyloxy, methylthio, ethylthio, n- or i-propylthio, n-, s- or t-butylthio,
propenylthio, butenylthio, propinylthio, butinylthio, methylamino,
ethylamino, n- or i-propylamino, n-, s- or t-butylamino, propenylamino,
butenylamino, propinylamino, butinylamino, dimethylamino or diethylamino,
each of which is optionally substituted by fluorine, chlorine, cyano, methoxy,
20 ethoxy, methylthio or ethylthio, or represents cyclopropyl, cyclopropyloxy or cyclopropylmethyl, each of which is optionally substituted by fluorine, chlorine, cyano or methyl.
R3 very especially preferably represents methyl, ethyl, n- or i-propyl, n-, s- or
25 t-butyl, propenyl, butenyl, pentenyl, hexenyl, propinyl, butinyl, pentinyl or hexinyl, each of which is optionally substituted by fluorine, cyano, methoxy, ethoxy, n- or i-propoxy, methylthio, eth)Ithio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, or represents cyclopropyl, cyclohutyl, cyclopentyl, cyclohcxyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl. cyclohcxylmethyl,
cyclohexylethyl or cyclohexylpropyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, or represents benzyl, phenylethyl, phenylpropyl, phenylbutyl, phenylethenyl, phenylpropenyl, phenylbutenyl, phenylethinyl, phenylpropinyl or
5 phenylbutinyl, each of which is optionally substituted by fluorine, chlorine,
bromine, cyano, methyl, ethyl, n- or i-propyl, n-, s- or t-butyl, methoxy or
Examples which may be mentioned individually of the.compounds of the formula (I) 10 to be used as components according to the invention in mixtures are:
4-amino-5-methy1-2-(1,1-dimethyl-ethyl-aminocarbony1)-2,4-dihydro-3H-1,2,4-tri-azol-3-one, 4-amino-5-ethy1-2-(1,1-dimethyl-ethyl-aminocarbony1)-2,4-dihydro-3H¬1,2,4-tri azol-3-one, 4-amino-5-n-propy1-2-(1,1-dimethyl-ethyl-aminocarbony1)-2,4-
15 dihydro-3H-1,2,4-triazol-3-one, 4-amino-5-i-propy1-2-(1,1-dimethyl-ethyl-
ethoxy-2-(1,1-dimethyl-ethyl-aminocarbony1)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4- amino-5-methy1-2-(2-fluoro-1,1-dimethyl-ethyl-aminocarbony1)-2,4-di hydro-3H-
20 1,2,4-triazol-3-one, 4-amino-5-ethy1-2-(2-fluoro-1,1-dimethyl-ethyl-aminocarbony1)-
ethyl-ami nocarbony1)-2,4-dihydro-3H-1,2,4-tri azol -3-one, 4-amino-5-i-propy1-2-(2- fluoro-1,1-dimethyl-ethyl-aminocarbony1)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4- amino-5-methox y-2-(2-fluoro-1,1-di methyl-ethyl -aminocarbony1)-2,4-dihydro-3H-
25 1,2,4-triazol-3-one, 4-amino-5-ethoxy-2-(2-fluoro-1,1-dimethyl-ethyl-amino-
carbony1)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4-amino-5-methy1-2-(2-chloro-1,1- di methyl-ethyl-aminocarbony1)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4-amino-5-ethy1- 2-(2-chloro-1,1-dimethyl-ethyl-aminocarbony1)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4-ami no-5-n-propy1-2-(2-chloro-1,1-dimethyl -ethyl -aminocarbony1)-2,4-di hydro-3H-
30 1.2.4-mazol-3-one, 4-amino-5-i-propy1-2-(2-chloro-1,1-dimethyl-ethyl-amino-
- 12 -
ethoxy-2-(2-chloro-1,1-dimethyl-ethyl-aminocrbony1)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4-amino-5-i-propy1-2-i-propyl-aminocarbony1-2,4-dihydro-3H-1,2,4-triazol-3- one, 4-amino-5-dimethylamino-2-(1,1-dimethyl-ethyl-aminocarbony1)-2,4-dihydro-
5 3H-1,2,4-triazol-3-one, 4-amino-5-dimethylamino-2-(2-fluoro-1,1-dimethy1-ethyl-
aminocarbony1)-2,4-dihydro-3H-1,2,4-triazol-3-one, 4-amino-5-dimethylamino-2-(2- chloro-1,1-dimethyl-ethyl-aminocarbony1)-2,4-dihydro-3H-1,2,4-triazol-3-one and 4- methy1-5-methoxy-2-(1,1-dimethyl-ethyl-aminocarbonyI)-2,4-dihydro-3H-1,2,4-
The compound 4-amino-5-(1-methyl-ethyl)-2-(1,1-dimethyl-ethyl-aminocarbony1)- 2,4-dihydro-3H-1,2,4-triazol-3-one — in accordance with Chem. Abstracts also to be termed 4-amino-N-(1,1-dimethyl-ethyl)-4,5-dihydro-3-(1-methyl-ethyl)-5-oxo-IH¬1,2,4-triazole-1-carboxamide (CAS-Reg. No.: 129909-90-6, Compound (I-1) of the
15 use examples, proposed common name: "amicarbazone") — is particularly
emphasized as component of the formula (I) in the mixture.
The compounds of the formula (I) are described in the abovementioned patent applications or patent specifications.
In accordance with their chemical structure, the active compounds of group 2 can be assigned to the following classes of active compounds:
Amides (for example, picolinafen, propanil), arylheterocycles (for example,
25 azafenidin, benzfendizone, butafenacil-allyl, cinidon-ethyl, fluazolate, flumioxazin, oxadiazon, oxadiargyl, profluazol, pyraflufen-ethyl, pyridatol, 444,5-dihydro-4- methyl-5-oxo-(3-trifluoromethyl)-1H-1,2,4-triazol-1-y1]-2-Rethylsulphonyl)amino1- 5-fluoro-benzenecarbothioamide), aryloxyphenoxypropionates (for example
cyhalofop-butyl, fenoxaprop-P-ethyl, fluazifop-P-but I. ha lox yfop-P-methyl,
30 quizalofop-P-ethyl), carboxylic acid derivatives (for c ample tyriclopyr).
chloroacetamides (for example dimethenamid-P, S-metolachlor. propisochlor).
- 13 -
cyclohexanediones (for example butroxydim, clefoxydim, cycloxydim, sethoxydim), dinitroanilines (for example benfluralin, oryzalin), diphenylethers (for example acifluorfen-sodium, fomesafen, lactofen, oxyfluorfen), isoxazoles (for example. isoxachlortole), oxyacetamides (for example mefenacet), pyridines (for example
5 thiazopyr), pyrimidinyl (thio)benzoates (for example pyribenzoxim, pyriminobac¬methyl, pyrithiobac-sodium), sulphonyl ureas (for example azimsulfuron, bensulfuron, chlorimuron-ethyl, flupyrsulfuron-methyl-sodium, foramsulfuron, iodosulfuron-methyl-sodium, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron), tetrazolinones (for example fentrazamide), thiocarbamates (for example
10 dimepiperate), triazinones (for example metamitron), triazoles (for example amitrole), triazolinones (for example flucarbazone-sodium, procarbazone-sodium) triazolopyrimidines (for example diclosulam, florasulam), triketones (for example mesotrione).
15 The following may be emphasized in particular as components for mixtures amongst
active compounds of group 2:
azafenidin, butafenacil-allyl, dimethenamid-P, fenoxaprop-P-ethyl, mesotrione, S-metolachlor.
The compositions according to the invention preferably comprise one or two active compounds of group 1, one to three active compounds of group 2 and, if appropriate, one active compound of group 3.
25 In particular, the compositions according to the invention comprise one active
compound of group 1. one or two active compounds of group 2 and, if appropriate, one active compound of group 3.
Examples of the active compound combinations according to the invention which 30 may be mentioned are
- 14 -
Amicarbazone + butafenacil-allyl, amicarbazone + mesotrione, amicarbazone + fenoxaprop-P-ethyl + mefenpyr-diethyl, amicarbazone + flucarbazone-sodium, amicarbazone + flucarbazone-sodium + mefenpyr-diethyl, amicarbazone + procarbazone-sodium, amicarbazone + procarbazone-sodium + mefenpyr-diethyl,
5 amicarbazone + dimethenamid-P, amicarbazone + S-metolachlor, amicarbazone + S-
metolachlor + benoxacor.
Surprisingly, it has now been found that the above-defined active compound
combinations of the carbamoyltriazolinones of the formula (I) and the
10 abovementioned active compounds of group 2 exhibit a particularly high herbicidal activity combined with essentially good crop plant tolerance and can be used for the selective control of monocotyledonous and dicotyledonous weeds in a variety of crops, in particular in maize, but additionally also in cotton, sunflowers, soya beans, potatoes, sugar cane, wheat, barley and rice, and that they can also be used for the
15 semi- and nonselective control of monocotyledonous and dicotyledonous weeds.
Surprisingly, the herbicidal activity of the active compound combinations according to the invention of compounds of the abovementioned groups 1 and 2 considerably exceeds the total of the action of the individual active compounds.
Thus, a synergistic effect is present which could not have been predicted, not just a complementation of action. The new active compound combinations are well tolerated in a variety of crops, also effecting good control of weeds which are usually difficult to control. Thus, the new active compound combinations are a valuable
25 enrichment of the herbicides.
The synergistic effect of the active compound combinations according to the
invention is particularly highly pronounced in certain concentration ratios. However,
the w eight ratios of the active compounds in the active compound combinations may
3() be vaned within substantial ranges. In general. 0.01 to 1000 parts by weight.
preferably 0.02 to 500 parts by weight. especially preferably 0.05 to 100 parts by
weight, of active compound of group 2 are used per part by weight of active compound of the formula (I).
The following may be particularly emphasized as components in mixtures from 5 amongst active compounds of group 3:
1-Methyl-hexyl 5-chloro-quinoxalin-8-oxy-acetate (cloquintocet-mexyl), ethyl 4,5-
dihydro-5,5-dipheny1-3-isoxazolecarboxylate (isoxadifen-ethyl) and diethyl 142,4-
10 diethyl) for improving the tolerance in cereals, and 4-dichloroacetyl-1-oxa-4-aza¬spiro[4.5]-decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2- a]-pyrimidin-6(2H)-one (BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H¬1,4-benzoxazine (benoxacor), 2,2-dichloro-N,N-di -2-propen yl-acetami de (dichlormid), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl)-oxazolodine (furilazole,
15 MON-13900), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148) for improving
the tolerance in maize.
It must be considered as surprising that, from amongst a multiplicity of known safeners
or antidotes capable of antagonizing the harmful effect of a herbicide on the crop
20 plants, it is precisely the abovementioned compounds of group 3 which are capable of virtually completely making up for the harmful effect, on the crop plants, of active compounds of the formula (I) and their salts, if appropriate also in combination with one or more of the abovementioned active compounds of group 2, without adversely affecting the herbicidal efficacy towards the weeds.
The advantageous effect of the crop plant tolerance of the active compound combinations according to the invention is also particularly highly pronounced. However, the weight ratios of the active compounds in the active compound combinations may be varied within substantial ranges. In general. 0.001 to 1000 parts
30 by weight, preferably 0.01 to 100 parts by weight. especiall■ preferably 0.1 to 10
- 16 -
parts by weight, of active compound of group 3 are used per part by weight of active compoUnd of the formula (I) or mixtures thereof with active compounds of group 2.
All plants and plant parts can be treated in accordance with the invention. Plants are to
5 be understood as meaning in the present context plants and plant populations such as desired and undesired wild plants or crop plants (inclusive of naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional plant breeding and optimization methods or by biotechnological and recombinant methods or by combinations of these methods, inclusive of the transgenic plants and inclusive of
10 the plant varieties protectable or not protectable by plant breeders' rights. Plant parts are to be understood as meaning all aerial and subterranean plant parts and organs of the plants such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, flowers, fruiting bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include vegetative and generative propagation material, for
15 example cuttings, tubers, rhizomes, offsets and seeds.
The treatment according to the invention of the plant and plant parts with the active
compounds is carried out directly or by allowing the compounds to act on the
surroundings, environment or storage space by the customary treatment methods, for
20 example by immersion, spraying, evaporation, fogging, scattering, painting on and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
Amongst the plants obtained by biotechnological and recombinant methods, or by 25 combining these methods, plants which are emphasized are those which tolerate so-
called 4-HPPD, EPSP and/or PPO inhibitors, such as, for example. Acuron plants.
The active compounds according to the invention can be used, for example. in the following plants:
- 17 -
Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodiurn, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium,
5 Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
10 Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita,
Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus,
15 Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.
However, the use of the active compound combinations according to the invention is in 25 no way restricted to these genera, but also extends in the same manner to other plants.
The active compound combinations to be used in accordance with the invention can
be employed not only in conventional cultivation methods (suitably placed row
crops) in plantation crops (for example grapevines, fruit, citrus) and in industrial
3() plants and railtracks. on paths and squares. but also for stubble treatment and in the
minimum tillage method. They arc furthermore suitable as dessicants (haulm killing
in, for example, potatoes) or as defoliants (for example in cotton). They are furthermore suitable for use on non-crop areas. Other fields of application are nurseries, forests, grassland and the production of ornamentals.
5 The active compound combinations can be converted into the customary
formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric materials.
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.
In the case of the use of water as an extender, organic solvents can, for example, also be used as cosolvents. The following are essentially suitable as liquid solvents: aromatics such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or
20 methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols such as bufanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylforrnamide and dimethyl sulphoxide, or else water.
Solid carriers which are suitable are:
for example ammonium salts and ground natural minerals such as kaolins, clays, talc,
chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground
synthetic materials such as highly-dispersed silica, alumina and silicates; suitable
30 solid catalysts for granules are: for example crushed and fractionated natural rocks
such as calcite, marble, pumice, sepiolite and dolomite, or else 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 nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates; suitable dispersants are: for example lignin sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers .in the
10 form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
15 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.
20 The formulations generally comprise between 0.1 and 95 per cent by weight of active
compounds, preferably between 0.5 and 90%.
The active compound combinations according to the invention are generally applied
in the form of ready mixes. However, the active compounds contained in the active
25 compound combinations may also be applied in the form of individual formulations
which arc mixed upon use, that is. in the form of tank mixes.
The new active compound combinations, as such or in their formulations, may
furthermore also be used as a mixture with other known herbicides, again with ready
30 mixes or tank mixes being possible. A mixture with other known active compounds
such as fungicides. insecticides. acaricides. nematicides. bird repellents. growth
- 20 -
substances, plant nutrients and soil conditioners is also possible. It may furthermore be advantageous for specific applications, in particular for the post-emergence method, to incorporate into the formulations plant-tolerated mineral or vegetable oils (for example the commercial product "Oleo DuPont 11E") or ammonium salts such
5 as, for example, ammonium sulphate or ammonium thiocyanate, as further additives.
The new active compound combinations can be used as such, in the form of their
formulations or the use forms which can be prepared from these formulations by
further dilution, such as ready-to-use solutions, suspensions, emulsions, powders,
10 pastes and granules. Application is effected in the customary manner, for example by
pouring, spraying, atomizing, dusting or broadcasting.
The active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say pre- and post-emergence. They may 15 also be incorporated into the soil prior to sowing.
The good herbicidal action of the new active compound combinations can be seen
from the examples which follow. While the individual active compounds show
weaknesses with regard to their herbicidal action, the combinations all show a
20 herbicidal action which exceeds a simple sum of actions.
A synergistic effect in herbicides is always present when the herbicidal action of the active compound combination exceeds the action of the active compounds when applied individually.
The expected action for a given combination of two herbicides can be calculated as follows (cf. COLBY. S.R.: "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, Pages 20-22, 1967):
- 21 -
X = % damage by herbicide A (active compound of the formula I) at an
5 application rate of p kg/ha
Y= % damage by herbicide B (active compound of the formula II) at an
application rate of q kg/ha
E= the expected damage of herbicides A + B at an application rate of p +
E= X + Y - (X * Y/100).
20 If the actual damage exceeds the calculated value, the combination has a
superadditive effect, that is to say a synergistic effect.
It can be seen from the use examples hereinbelow that the found herbicidal action of
the active compound combinations according to the invention exceeds the calculated
25 value, that is to say that the new active compound combinations have a synergistic
Customary formulations of the respective active compounds were used. Butafenacil
was employed as Inspire ® 100 EC, azafenidin as an 80 WG formulation and the
5 compound of the formula (I-1) as a 70 WG formulation. The active compounds were
used to prepare an aqueous spray mixture with 0.1% of Renex-36 as additive.
Seeds of the test plants are sown in standard soil. After 24 hours, the test compound
or the combination of test compounds, is sprayed onto the soil surface in such a
manner as to apply the amount of active compound per unit area desired in each case.
15 The concentration of the spray mixture is chosen so that the desired amounts of
active compound desired are applied in 5001 of water per ha.
After the spray application, the plant containers are placed in the greenhouse under constant light and temperature conditions.
After approximately 3 weeks, the degree of damage of the crop plants is scored in % damage in comparison with the development of the untreated control.
The figures denote:
0% = no damage (as untreated control) 100% = Total destruction/damage
Active compounds, application rates, test plants and results can be seen from the 30 tables which follow, the terms used in the tables hating the folkming meanings:
- 23 -
a.i. = active ingredient
g ai/ha Alopecurus observed Alupecurus calculated*
Compound 125 0
Butafenacil 2 0
0.5 0 •
Compound 125 + 2 70 0
(I-1) + 125 + 0.5 60 - 0
g ai/ha Digitaria observed Digitaria calculated*
Compound (I-1) 125 40
Butafenacil 1 20
Compound (I-1)+ Butafenacil 125 + 1 90 52
MKH 3586 + Butafenacil 125 + 0.5 90 52
10 * Data calculated using Coltlys formula
Le A 34 119-Foreign Countries
- 24 -
g ai/ha Setaria observed Setaria calculated*
Compound 125 0
Butafenacil 2 0
Compound 125 + 2 80 0
(I-1) + 125 + 0.5 70 0
g ai/ha Abutilon observed Abutilon calculated*
Compound (I-1) 60 50
Butafenacil 2 30
(1-1) + Butafenacil 60 + 2 95 65
10 * Data calculated using Colby's formula
Le A 34 119-Foreign Countries
g Willa Cassia observed Cassia calculated*
Compound (I-1) 60 30
Butafenacil 0.5 0
MICH 3586 + Butafenacil 60 + 0.5 100 30
Application rate g ai/ha Datura observed Datura calculated*
Compound (I-1) 60 50
Butafenacil 2 30
Compound (I-1) + Butafenacil 60 + 2 100 65
* Data calculated using Colby's formula
Le A 34 119-Foreign Countries
- 26 -
Application rate g aiiha Galium observed Galium calculated*
Compound (I-1) 125 80
Butafenacil 1 0
Compound (I-1) + Butafenacil 125 + 1 100 80
Application rate g ai/ha Ipomea observed Ipomea calculated*
Compound (I-1) 125 50
Butafenacil 0.5 0
Compound (I-1) + Butafenacil 125 + 0.5 98 50
* Data calculated using Colby's formula
Le A 34 119-Foreign Countries
- 27 -
Application rate g ai/ha Solanum observed Solanum calculated*
Compound 60 90
Butafenacil 2 0
0,5 0 •
Compound 60 + 2 100 - 90
(I-1) 60 + 1 100 90
+ Butafenacil 60 + 0,5 98 .. 90
Application rate g aitha Xanthium observed Xanthium calculated*
Compound (I-1) 125 90
Butafenacil 2 0
+ Butafenacil 125 + 2 100 90
* Data calculated using Colby's formula
Le A 34 119-Foeign Countries
- 28 -
1. A composition characterising an active compound combination comprising 4-amino-5-(1-methyl-ethyl)-2-(1,1-dimethyl-ethyl-aminocarbony1)-2-4- dihydro -3H-1,2,4, -triazol-3-one, and
[1,1-dimethy1-2-oxo-2-(2-propenyloxy)[-ethyl 2-chloro-5-(3,6-dihydro-3- methy1-2,6-dioxo-4-trifluoromethy1-1(2H)-pyrimidiny1)-benzoate (butafenacil-ally]).
2. A composition according to Claim 1, further comprising an active
10 compound of group 3.
3. Use of a composition according to Claim 1 for controlling undesired plants.
4. A process for the preparation of a composition according to Claim 1,
15 characterised in that the active compounds are mixed with customary
extenders and/or surfactants.
Herbicides hued on carbamo Itriazolinones
The invention rciaLes to new herbicidal, synergistic active compound combinations which nm composed of known carbarnoyitriazolinones on lh one hand and known, hnrhicidally active compounds on the other hand and which can be used particularly sucocssfuliy for controlling weeds.
indexation.Ist QCOK tags.Ist
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