EP3618620A1 - Herbicide safener compositions containing quinazolinedione-6-carbonyl derivatives - Google Patents
Herbicide safener compositions containing quinazolinedione-6-carbonyl derivativesInfo
- Publication number
- EP3618620A1 EP3618620A1 EP18719897.3A EP18719897A EP3618620A1 EP 3618620 A1 EP3618620 A1 EP 3618620A1 EP 18719897 A EP18719897 A EP 18719897A EP 3618620 A1 EP3618620 A1 EP 3618620A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- alkoxy
- cycloalkyl
- halogeno
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 74
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 61
- 239000004009 herbicide Substances 0.000 title claims abstract description 58
- -1 quinazolinedione-6-carbonyl Chemical class 0.000 title claims abstract description 55
- 241000196324 Embryophyta Species 0.000 claims abstract description 75
- 239000001257 hydrogen Substances 0.000 claims abstract description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 62
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims abstract description 12
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims abstract description 11
- OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 claims abstract description 9
- 244000045561 useful plants Species 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000005843 halogen group Chemical group 0.000 claims description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical group 0.000 claims description 35
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
- 240000007594 Oryza sativa Species 0.000 claims description 18
- 235000007164 Oryza sativa Nutrition 0.000 claims description 18
- 235000009566 rice Nutrition 0.000 claims description 18
- 240000008042 Zea mays Species 0.000 claims description 16
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 16
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 16
- 235000005822 corn Nutrition 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
- 235000010469 Glycine max Nutrition 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- MCNOFYBITGAAGM-UHFFFAOYSA-N 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 10
- UKSLKNUCVPZQCQ-UHFFFAOYSA-N Fluxofenim Chemical compound C=1C=C(Cl)C=CC=1C(C(F)(F)F)=NOCC1OCCO1 UKSLKNUCVPZQCQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- HKELWJONQIFBPO-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl HKELWJONQIFBPO-UHFFFAOYSA-N 0.000 claims description 7
- 244000075850 Avena orientalis Species 0.000 claims description 7
- 229920000742 Cotton Polymers 0.000 claims description 7
- 240000005979 Hordeum vulgare Species 0.000 claims description 7
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 7
- 235000021307 Triticum Nutrition 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 235000007319 Avena orientalis Nutrition 0.000 claims description 6
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 6
- 235000007238 Secale cereale Nutrition 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims description 5
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims description 5
- WFVUIONFJOAYPK-KAMYIIQDSA-N Oxabetrinil Chemical compound C=1C=CC=CC=1C(/C#N)=N\OCC1OCCO1 WFVUIONFJOAYPK-KAMYIIQDSA-N 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 4
- LPVPNRSVMLNXGQ-UHFFFAOYSA-N 1-(azepan-1-yl)-2,2-dichloroethanone Chemical compound ClC(Cl)C(=O)N1CCCCCC1 LPVPNRSVMLNXGQ-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims description 4
- 240000000111 Saccharum officinarum Species 0.000 claims description 4
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 4
- JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 3
- QQNIGXQDICUWGT-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-3-azaspiro[4.5]decan-3-yl)ethanone Chemical compound C1N(C(=O)C(Cl)Cl)COC21CCCCC2 QQNIGXQDICUWGT-UHFFFAOYSA-N 0.000 claims description 3
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- XXWNKVBJDWSYBN-UHFFFAOYSA-N diethoxy-phenoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=CC=CC=C1 XXWNKVBJDWSYBN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 2
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 2
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 2
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 2
- HIGVQLLGNCHWAA-UHFFFAOYSA-N 1-(2-methoxyphenyl)ethanone;n-propan-2-yl-4-sulfamoylbenzamide Chemical compound COC1=CC=CC=C1C(C)=O.CC(C)NC(=O)C1=CC=C(S(N)(=O)=O)C=C1 HIGVQLLGNCHWAA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- GMBRUAIJEFRHFQ-UHFFFAOYSA-N Fenchlorazole-ethyl Chemical group N1=C(C(=O)OCC)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl GMBRUAIJEFRHFQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- MCNOFYBITGAAGM-MRVPVSSYSA-N (R)-furilazole Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)O[C@H]1C1=CC=CO1 MCNOFYBITGAAGM-MRVPVSSYSA-N 0.000 claims 1
- PYKLUAIDKVVEOS-RAXLEYEMSA-N (e)-n-(cyanomethoxy)benzenecarboximidoyl cyanide Chemical compound N#CCO\N=C(\C#N)C1=CC=CC=C1 PYKLUAIDKVVEOS-RAXLEYEMSA-N 0.000 claims 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 1
- 241000219146 Gossypium Species 0.000 claims 1
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 1
- 241000209056 Secale Species 0.000 claims 1
- 240000006394 Sorghum bicolor Species 0.000 claims 1
- 244000098338 Triticum aestivum Species 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000006525 methoxy ethyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])OC([H])([H])[H] 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 17
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 150000001787 chalcogens Chemical group 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
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- 238000009472 formulation Methods 0.000 description 20
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 5
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- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
Definitions
- Herbicidal safener compositions containing quinazolinedione-6-carbonyl derivatives containing quinazolinedione-6-carbonyl derivatives
- the present invention relates to agrochemically active herbicidal safener composition process for their preparation and their use for controlling harmful plants.
- the object of the present invention is therefore to provide herbicidal compositions in which the selectivity of the abovementioned herbicides is increased in relation to important crop plants. This object is achieved by the herbicide-safener compositions according to the invention described below containing herbicides and safeners.
- the present invention provides herbicidal safener compositions comprising (A) one or more herbicidally active compounds of the formula (I) or salts thereof,
- phenyl rings of the eight abovementioned radicals each carry s substituents R 6 , is hydrogen, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) alkynyl , (C 2 -C 6) -haloalkynyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) - halocycloalkyl, (Ci-C6) alkyl-0-
- Q 5 Q 6 Q 7 Q 8 Y is O, CO or CR s6 R s7 ,
- R sl is hydroxy or SR 7 ,
- R s2 and R s5 each independently of one another denote hydrogen or (C 1 -C 4 ) -alkyl, or R s2 and R s5 together form an ethylene or vinylene group,
- R s3 , R s4 , R s6 and R s7 are each independently hydrogen or (Ci-C i) -alkyl
- R pl is hydrogen, (C 1 -C 6 ) -alkylsulfonyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 6 ) -alkylsulfonyl, or in each case by m identical or different radicals from the group consisting of halogen, C4) -alkyl and (C 1 -C 4 ) -alkoxy-substituted phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl- (C 1 -C 6) -alkyl or benzyl,
- R p2 is (C 1 -C 4 ) -alkyl
- R p3 is hydrogen, (C 1 -C 4 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 4 ) -alkyl (C 3 -C 8 ) -cycloalkyl, (C 3 -C 6 ) - halocycloalkyl,
- R nl represents (Ci-C 4) -alkyl, (C 3 -C 8) cycloalkyl, (Ci-C 4) -alkyl- (C 3 -C 8) cycloalkyl, (C 3 -C 6) - halocycloalkyl,
- R n2 is hydrogen, C0 2 (C 1 -C 6 ) -alkyl or S (0) n (C 1 -C 6 ) -alkyl,
- W 1 denotes (C 1 -C 10) -alkylene, (C 2 -C 6 ) -alkenylene or (C 2 -C 6 ) -alkynylene,
- W 2 denotes (C 1 -C 10) -alkylene
- R 6a is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl,
- R 7 is (Ci-C i) -alkyl or by p radicals from the group halogen, nitro, cyano, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy and (Ci -C4) -haloalkoxy-substituted phenyl, n is 0, 1 or 2, P is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5, t is 0, 1, 2, 3 or 4, v is 2, 3, 4, 5, 6 or 7, as well
- herbicidal safener compositions of the invention may be additional additional additional
- Components for example, crop protection agents of other types and / or additives customary in crop protection and / or formulation auxiliaries, or used together with these.
- the herbicides (A) and safeners (B) can be applied in a known manner, for example jointly (for example as a co-formulation or as a tank mixture) or also as a splitting, e.g. on the plants, plant parts, plant seeds or the area on which the plants grow. It is possible, e.g. the application of the individual active substances or the herbicide-safener composition in several portions (sequence application), z. B. for applications in
- Preferred herbicidal safener compositions according to the invention which contain as herbicides (A) those compounds of the general formula (I) and salts thereof, in which X denotes halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) - Haloalkyl, (C 2 -C 6 ) -alkenyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl, OR 1 , S (O) n R 2 , SO 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR'COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 or (C 1 -C 6 ) -alkyl-OR 1 Z means O,
- W is hydrogen, F, Cl, MeO, methyl or ethyl
- R 1 represents (C 1 -C 10) -alkyl, (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, halogeno (C 1 -C 10) -alkyl, halogeno (C 2 -C 10) -alkenyl, halogen - (C2-Cio) alkynyl, (C3-Cio) cycloalkyl, halo (C3-Cio) cycloalkyl, (C1-C4) - alkyl- (C 3 -C 7) cycloalkyl, (C3-C 7 ) -cycloalkyl- (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) - alkyl (C 3 -C 7) cycloalkyl, (Ci-C 6) alkylthio (Ci-C
- R 1 is phenyl which carries s substituent R 6 ,
- R 2 is (C 1 -C 4 ) -alkyl
- Q is a radical Q 5 , Q 6 , Q 7 or Q 8 ,
- R 6a is hydrogen or (C 1 -C 6 ) -alkyl
- Y is O, CO or CR s6 R s7 ,
- R sl is hydroxy
- R s2 and R s5 each independently represent hydrogen or methyl, or
- R s2 and R s5 together form an ethylene or vinylene group
- R s3 , R s4 , R s6 and R s7 are each independently hydrogen or methyl, R p1 is hydrogen, R p2 is (C 1 -C 4 ) -alkyl,
- R p3 is hydrogen, (Ci-C i) -alkyl or cyclopropyl, R nl is cyclopropyl,
- R n2 is hydrogen, n is 0, 1 or 2, p is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, 4 or 5.
- the compounds of the formula (I) present in the herbicidal safener compositions according to the invention and the safeners described below may each form salts. Salt formation can be effected by the action of a base on those compounds of the formula (I) or safeners which have a bear acidic hydrogen atom, for example, in the case that R 1 contains a COOH group or a sulfonamide group NHSO2.
- Suitable bases are, for example, organic amines, such as tri-alkylamines, morpholine, piperidine or pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular NaOH, KOH, Na 2 C03, K 2 CO 3, NaHCO 3, and KHCO 3.
- salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts , for example with cations of the formula [NRR'R "R"'] + , where R to R'"in each case represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl
- Alkylsulfoxoniumsalze such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -Trialkylsulfoxoniumsalze.
- the compounds of the formula (I) and the safeners described below can be obtained by addition of a suitable inorganic or organic acid, e.g. Mineral acids such as HCl, HBr, H2SO4, H3PO4 or HNO3, or organic acids, e.g.
- a suitable inorganic or organic acid e.g. Mineral acids such as HCl, HBr, H2SO4, H3PO4 or HNO3, or organic acids, e.g.
- carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid, to a basic group such.
- Amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino each form a salt.
- These salts then contain the conjugate base of the acid as an anion.
- radicals with carbon atoms those having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are generally preferred.
- R s6 s7 group is a CR R s6 s7 group
- R sl is hydroxy
- R s2, R s3, s4 R, R s5 and W represents hydrogen and R: is methyl, and Z is oxygen.
- Methyl, W and R pl are hydrogen, and Z is oxygen.
- the application rate of the herbicides (A) can be compared with the external conditions such as temperature,
- the application rates are generally lower, z. In the range of 0.1 g to 800 g a.i./ha, preferably 1 g to 500 g a.i./ha, more preferably 10 g to 400 g a.i./ha.
- the herbicides (A) are useful for controlling harmful plants, e.g. suitable in crops, for example in economically important crops e.g. monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats), rice, corn, millet, or dicotyledonous crops such as sugar beet, oilseed rape, cotton, sunflower and legumes, e.g. of the genera Glycine (eg Glycine max.
- monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats), rice, corn, millet, or dicotyledonous crops such as sugar beet, oilseed rape, cotton, sunflower and legumes, e.g. of the genera Glycine (eg Glycine max.
- Glycine max as non-transgenic Glycine max (eg conventional varieties such as STS varieties) or transgenic Glycine max (eg RR soy or LL soy) and their crosses), Phaseolus, Pisum , Vicia and Arachis, or vegetable crops from various botanical groups such as potato, leek, cabbage, carrot, tomato, onion, and permanent and plantation crops such as pome and stone fruit, soft fruit, wine, Hevea, bananas, sugar cane, coffee, tea, citrus , Nut plantations, lawn,
- herbicidal safener compositions (A) + (B) are also preferred, the use in cereals (eg wheat, barley, rye, oats), rice, corn, millet, sugar beet, sugar cane is particularly preferred , Sunflower, rapeseed and cotton.
- the herbicidal safener compositions (A) + (B) are also useful in tolerant and non-tolerant mutant cultures and tolerant and intolerant transgenic cultures, preferably from corn, rice, corn, oilseed rape and soy, e.g. those which are resistant to imidazolinone herbicides, atrazine, glufosinate or glyphosate.
- the safeners referred to as component (B) are compounds which are suitable for reducing phytotoxic effects of crop protection active ingredients such as herbicides on crop plants.
- herbicides (A) are combined with the following safener compounds:
- dichlorophenylpyrazolecarboxylic acid Sl b
- compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylate (S 1 -2)
- Sl e compounds of the type of 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid, or of 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
- S2 a compounds of the 8-quinolinoxyacetic acid type (S2 a ), preferably
- R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),
- R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3),
- Benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
- PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide
- TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
- Diaclonone (dicyclonone) (synonym: “BAS145138” or “LAB145138”) (RS) -l-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo [1,2-fl] pyrimidin-6-one from BASF (S3- 9)
- RA 1 denotes (C 1 -C 6) -alkyl or (C 3 -C 6) -cycloalkyl, where these radicals are substituted by VA substituents from the group consisting of halogen, (C 1 -C 6) -alkoxy, (C 1 -C 6) -haloalkoxy and (C 1 -C 6) -cycloalkyl.
- C4) -alkylthio and in the case of cyclic radicals are also substituted by (Ci-C4) -alkyl and (Ci-C4) -haloalkyl;
- RA 2 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, CF 3;
- mA 1 or 2;
- VA 0, 1, 2 or 3.
- Verbindun conditions the type of 4- benzoylsulfamoyl) benzamide of the formula (S4 b) and their salts as i -A-99 are / 16744 describes
- RB 1 , RB 2 independently of one another denote hydrogen, (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl,
- RB 3 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl or (C 1 -C 4 ) -alkoxy and ms is 1 or 2, for example those in which
- RB 1 cyclopropyl
- R B 2 hydrogen
- (RB 3 ) 2-OMe (S4-1, "Cyprosulfamide”)
- RB 1 cyclopropyl
- R B 2 hydrogen
- (RB 3 ) 5-Cl-2-OMe (S4-2)
- RB 1 isopropyl
- R B 2 hydrogen
- (RB 3 ) 5-Cl-2-OMe is (S4-4) and
- RB 1 isopropyl
- R B 2 hydrogen
- (RB 3 ) 2-OMe (S4-5).
- Rc 1 , Rc 2 independently of one another denote hydrogen, (Ci-Cg) -alkyl, (C3-Cg) -cycloalkyl, (C3-)
- R c 3 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or CF 3 ;
- Verbindun gene of the type of N-phenylsulfonylterephthalamide of the following formula (S4 d ) ande salts thereof, for example, are known from CN 101838227,
- R D 4 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or CF 3;
- R D 5 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl or (C 5 -C 6 ) cycloalkenyl.
- Carboxylic acid derivatives (S5) e.g.
- S6 active compounds from the class of 1,2-dihydroquinoxaline-2-ones (S6), e.g.
- S7 compounds from the class of diphenylmethoxyacetic acid derivatives (S7), e.g.
- RD 1 represents halogen, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, R D 2 represents hydrogen or (Ci- C 4 ) alkyl
- R D 3 is hydrogen, (Ci-Cg) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more , preferably up to three identical or different radicals from the group consisting of halogen and alkoxy substituted; or their salts
- n D means 0, 1 or 2.
- RE 1 is halogen, (C 1 -C 4 ) -alkyl, methoxy, nitro, cyano, CF 3 , OCF 3
- YE, ZE independently of one another denote O or S,
- n E 0, 1, 2, 3 or 4,
- R E 2 is (Ci-Ci 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 3 -C 6 ) -cycloalkyl, aryl, benzyl or
- R E 3 is hydrogen or (Ci-C6) alkyl.
- Oxabetrinil ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl l -1), which is known as a seed dressing safener for millet against damage by metolachlor,
- Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl 1 -3), which is known as a seed dressing safener for millet against damage by metolachlor.
- Isothiochromanone (S 12) class agents such as Methyl [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS reference No. 205121 -04-6) (S12-1) and related compounds of WO-A -1998 / 13361.
- Naphthalene anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides.
- MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn,
- active substances which, in addition to a herbicidal activity against harmful plants, also have safener action on crops such as rice, such as, for example, rice.
- CSB (1-Bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Registry No. 54091-06-4), which is known as a safener against damage of some herbicides in rice.
- RH 1 is a (C 1 -C 6) -haloalkyl radical
- RH 2 is hydrogen or halogen
- RH 3 , RH 4 independently of one another are hydrogen, (C 1 -C 16) -alkyl, (C 2 -C 6) -alkenyl or
- each of the last-mentioned 3 unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C i) alkoxy, (Ci-C i) -haloalkoxy, (Ci-C4) alkylthio, (C1 -C4) -alkylamino, di [(C 1 -C 4 ) -alkyl] -amino, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6 ) ) Cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted,
- each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, ( Ci-C4) - haloalkoxy, (Ci-C 4) alkylthio, (Ci-C 4) alkylamin
- RH 3 and RH 4 together with the directly attached N atom form a four- to eight-membered one
- heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and which may be unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, nitro, C 4 ) alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy and (C 1 -C 4 ) -alkylthio.
- herbicidal safener compositions of herbicides (A) and safeners (B) are shown in the following overview:
- herbicidal safener compositions of the herbicides (A) with the following safeners are preferred: mefenpyr-diethyl, fenchlorazole, isoxadifen-ethyl, cloquintocetmexyl, dichloromide, 3-dichloroacetyl-2,2,5-trimethyl-1 , 3-oxazolidine, benoxacor, 3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane, 1-dichloroacetyl-azepane, furilazole, ((R) -3-dichloro-acetyl-5- (2-furyl ) -2,2-dimethyloxazolidine), cyprosulfamide, N-isopropyl-4-sulfamoylbenzamide 1 - (2-methoxyphenyl) ethanone, 1- [4- (N-2-methoxybenzo
- compositions of the herbicides (A) with the safeners daimurone, benoxacor, furilazole, fluxofenim, fenchlorazole (ethyl ester), mefenpyr-diethyl, cloquintocet-mexyl, isoxadifen-ethyl, cyprosulfamides, flurazoles, oxabetrinil, dichloromide and dietholates.
- herbicidal safener compositions of the herbicides (A) with the following safeners: mefenpyr-diethyl, isoxadifen-ethyl, cyprosulfamide, fenchlorazole-ethyl ester, benoxacor, cloquintocet-mexyl, fluxofenim and furilazole.
- R 1 represents 2-methylphenyl, 2-methoxyphenyl or 2-trifluoromethylphenyl, R 2 is methyl,
- X is methyl
- Y is CR s6 R s7 ,
- R sl is hydroxy
- R s2 is hydrogen
- R s3 is hydrogen
- R s4 is hydrogen
- R s5 is hydrogen
- R s6 is hydrogen or methyl
- R s7 is hydrogen or methyl
- the safeners mefenpyr-diethyl, fenchlorazole (ethyl), isoxadifen-ethyl, cloquintocet-mexyl, benoxacor, furilazole, cyprosulfamide, fluxofenim and 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea.
- herbicidally effective amount means an amount of one or more herbicides which is suitable for negatively influencing plant growth.
- Antidote effective amount in the sense of the invention means an amount of one or more safeners which is suitable for reducing the phytotoxic effect of crop protection active ingredients (for example of herbicides) on crop plants.
- the safeners (B) are suitable for reducing the phytotoxic effects that can occur when using herbicides of the general formula (I) in crops without significantly impairing the effectiveness of these herbicidal active compounds against harmful plants. This can do that
- the required application rates of the safeners can vary within wide limits and are generally in the range from 0.001 to 5 kg, preferably 0.005 to 2.5 kg and especially 0.05 to 0.5 kg of active ingredient per hectare ,
- the herbicides (A) and the safeners (B) can be applied together (eg as a finished formulation or in the tank mix process) or in any desired sequence, for example by spraying, pouring and spraying or by granule scattering.
- the weight ratio herbicide of general formula (I) (A): safener (B) may vary within wide limits and is preferably in the range of 1: 10,000 to 10,000: 1, especially 1: 1000 to 1000: 1 and ganu especially from 1:20 to 20: 1.
- the optimum amounts of the general formula (I) (A) and safener (B) in each case are of the type of herbicide and safener used and of the type and development stage of the plant stock to be treated and can be determined on a case-by-case basis by simple, routine preliminary tests.
- the safeners (B) present in the herbicidal safener compositions according to the invention can be used for pretreatment of the seed of the crop (for seed dressing, for example) or introduced into the seed furrows before sowing or together with the herbicide before or after be applied to the emergence of the plants.
- Pre-emergence treatment includes both the treatment of the acreage (including possibly on the acreage
- the seeds e.g., grains, seeds or vegetative
- Propagating organs such as tubers or sprouts with buds) or seedlings with the safeners (B), optionally in combination with other agrochemical active ingredients pretreated.
- Pretreatment of the seed may be the active ingredients e.g. by seed dressing or the active ingredients and the seed may be added to water or other solvents, and the active ingredients e.g. be absorbed by addition or diffusion in the dipping process or by swelling or pre-germination.
- the young plants may be e.g. by spraying, dipping or pouring with the safeners, optionally in combination with other agrochemical active ingredients, brought into contact and then transplanted and optionally treated with the herbicides (A).
- Seedling or seedling treatment may be carried out with the safeners (B) alone or in conjunction with other agrochemical active substances - such as fungicides, insecticides or plant-strengthening agents, fertilizers or to speed up the swelling and germination processes.
- the safeners after the pretreatment application can then be applied again before, after or together with one or more herbicides (A), possibly also in combination with other known herbicides.
- A herbicides
- the present invention thus further provides a process for controlling unwanted plants in plant crops, which is characterized in that the herbicides (A) and the safeners (B) of the herbicidal safener compositions according to the invention are applied to the plants (for example harmful plants, such as monocrops). or dicotyledonous weeds or unwanted crops), the Seeds (eg grains, seeds or vegetative propagules such as tubers or sprouts with buds) or the area on which the plants grow (eg the acreage) are applied, eg together or separately.
- the plants for example harmful plants, such as monocrops). or dicotyledonous weeds or unwanted crops
- the Seeds eg grains, seeds or vegetative propagules such as tubers or sprouts with buds
- the area on which the plants grow eg the acreage
- S1 to S15 preferably one or more, in particular one, compound of groups (S1) to (S15) before, after or simultaneously with the herbicide (s) of general formula (I) (A) on the plants, the seed or the area on which the plants grow (eg the acreage) are applied.
- the safeners (B) are used for seed treatment.
- Undesirable plants are understood to mean all plants that grow in places where they are undesirable. This can e.g. Harmful plants (e.g., mono- or dicotyledonous weeds or undesired crops), e.g. also those which are resistant to certain herbicidal active substances such as glyphosate, atrazine, glufosinate or imidazolinone herbicides.
- Harmful plants e.g., mono- or dicotyledonous weeds or undesired crops
- certain herbicidal active substances such as glyphosate, atrazine, glufosinate or imidazolinone herbicides.
- Monocotyledonous weeds are derived e.g. the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron,
- an effective amount of the herbicides (A) and safeners (B) are used to control harmful plants in crops, for example, in economically important crops, e.g. monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats), rice, corn, millet, or dicotyledonous crops such as sugar beet, oilseed rape, cotton, sunflowers, and legumes, e.g. of the genera Glycine (eg Glycine max like non-transgenic Glycine max.
- monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats), rice, corn, millet, or dicotyledonous crops such as sugar beet, oilseed rape, cotton, sunflowers, and legumes, e.g. of the genera Glycine (eg Glycine max like non-transgenic Glycine max.
- Phaseolus eg conventional strains like STS strains
- transgenic Glycine max eg RR soy or LL soy
- Phaseolus Phaseolus, Pisum, Vicia and Arachis, or vegetable crops from various botanical groups such as potato, leek, cabbage, carrot, tomato, onion, and permanent and plantation crops such as pome and stone fruit, soft fruit, wine, Hevea, bananas, sugar cane, coffee, tea, citrus, nut plantations, Lawn, Palm Cultures and Forest Cultures.
- the invention also provides the use of the herbicidal safener compositions according to the invention for controlling undesired plant growth, preferably in
- herbicidal safener compositions according to the invention can be prepared by known processes, for example as mixed formulations of the individual components, if appropriate with further active compounds,
- Additives and / or customary formulation auxiliaries are prepared, which are then diluted in the usual way with water used, or as so-called tank mixes by common dilution of the separately formulated or partially formulated separately
- herbicidal safener compositions according to the invention can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
- the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
- Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
- transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
- Other special properties may be in a tolerance or resistance to abiotic stressors z. As heat, cold, drought, salt and ultraviolet radiation.
- the application of the herbicidal safener compositions according to the invention in economically important transgenic crops of useful and ornamental plants eg.
- cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or even cultures of sugar beet,
- the herbicides (A) can be used in crops that are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
- Conventional ways of producing new plants which have modified properties in comparison with previously occurring plants consist, for example, in classical methods
- new plants can be modified Properties can be generated using genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624).
- genetic modifications of crop plants have been described in several cases in order to modify the starch synthesized in the plants (eg WO 92/11376, WO 92/14827, WO 91/19806),
- transgenic crop plants which are resistant to certain glufosinate-type herbicides (cf., for example, EP-A-0242236, EP-A-242246) or glyphosate (WO 92/00377) or the sulfonylureas (EP-A-0257993, US Pat -5013659) are resistant,
- Bt toxins Bacillus thuringiensis toxins
- Transgenic crops that are characterized by higher yields or better quality - transgenic crops characterized by a combination of z.
- B. the o. G. characterize new properties ("gene stacking")
- nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
- adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Edition Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996
- the production of plant cells with reduced activity of a gene product can For example, be achieved by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a Cosuppressions freees or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
- DNA molecules can be used which comprise the entire coding sequence of a gene product including any flanking sequences, as well as DNA molecules which comprise only parts of the coding sequence, which parts have to be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
- the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
- the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
- sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
- the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
- the transgenic plant cells can be regenerated to whole plants by known techniques.
- the transgenic plants can in principle be plants of any one
- Plant species that is, both monocotyledonous and dicotyledonous plants.
- inventive herbicide-safener compositions according to the invention can be used in transgenic cultures which are resistant to growth substances, such as. B. Dicamba or against herbicides, the essential plant enzymes, eg. Acetylactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit, respectively, herbicides from the group of sulfonylureas, the glyphosate,
- the essential plant enzymes eg. Acetylactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit, respectively, herbicides from the group of sulfonylureas, the glyphosate,
- Glufosinate or benzoylisoxazole and analogues that are resistant are resistant.
- the invention therefore also relates to the use of the inventive herbicide-safener compositions according to the invention for controlling harmful plants in transgenic
- the application of the herbicidal safener compositions of the invention in economically important transgenic crops of useful and ornamental plants eg. Cereals (e.g., wheat, barley, rye, oats), millet, rice, cassava, and corn, or also sugar beet, cotton, soy, rapeseed, potato, tomato, pea, and other vegetable crops.
- the invention therefore also relates to the use of the herbicidal safener compositions according to the invention for controlling harmful plants in transgenic crop plants or
- the herbicides (A) and the safeners (B) may be used together or separately in common formulations e.g. be applied for spraying, pouring, spraying and seed dressing, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active ingredient impregnated natural and synthetic substances, Feinstverkapselitch in polymeric materials.
- the formulations may contain the usual auxiliaries and additives.
- formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, that is to say liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-forming agents.
- extenders that is to say liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-forming agents.
- Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or 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 their ethers and esters, ketones, such as acetone, Methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as
- Suitable solid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates; suitable solid carriers for granules are: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
- nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates and protein hydrolysates;
- suitable dispersants are: e.g. Ligninsulfitablaugen and
- Adhesives such as carboxymethylcellulose, natural and synthetic, powdery, granular or latex-like polymers, such as gum arabic, can be used in the formulations.
- Other additives may be mineral and vegetable oils.
- Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90% by weight.
- herbicides (A) and safeners (B) can be used as such or in their formulations also in admixture with other agrochemical active substances, such as known herbicides, for controlling undesired plant growth, e.g. for weed control or to control undesirable crops, e.g. Ready-to-use formulations or tank mixes are possible.
- mixtures with other known active ingredients such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and
- Soil improvers are possible, as well as common in plant protection additives and formulation auxiliaries.
- the herbicides (A) and the safeners (B) can be used as such, in the form of their formulations or the forms of use prepared therefrom by further dilution, such as ready-to-use solutions,
- Suspensions, emulsions, powders, pastes and granules are applied.
- the application is usually done, e.g. by pouring, spraying, spraying, sprinkling.
- the active substances can be applied to the plants, parts of plants, the seed or the acreage (field soil), preferably to the seed or the green plants and plant parts and optionally additionally to the field soil.
- One possibility of application is the joint application of the active ingredients in the form of tank mixes, with the optimally formulated
- a common formulation of the herbicidal safener compositions of herbicide (A) and safener (B) of the present invention has the advantage of ease of use because the amounts of the herbicides
- Components can already be set in the optimum ratio to each other.
- the adjuvants in the formulation can be optimally matched to one another.
- Mixture formulations or in the tank mix are, for example, known, preferably herbicidal active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl coenzyme A carboxylase, PS I, PS II, HPPD, phytoene desaturase, protoporphyrinogen oxidase, glutamine Synthetase, cellulose biosynthesis, 5-Enolpyruvylshikimat-3-phosphate synthetase based, can be used.
- herbicidal active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl coenzyme A carboxylase, PS I, PS II, HPPD, phytoene desaturase, protoporphyrinogen oxidase, glutamine Synthetase, cellulose biosynthesis, 5-Enolpyruvylshikimat-3-phosphate synthetase based, can be used.
- herbicide-safener compositions according to the invention can be combined, e.g.
- the following compounds are to be mentioned (note: The compounds are either with the "common name” according to the International Organization for Standardization (ISO) or with the chemical name, possibly together with a common code number and always include all
- Use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
- 2,4-D acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidosulfuron, aminopyralid, amitrole, anilofos, asulam, atrazine, azafenidine, azimsulfuron, beflubutamide, benazoline, benazoline ethyl, benfuresate, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclone, benzofenap, bifenox, bilanafos, bispyribac-sodium, bromoacil, bromobutides, bromofenoxime, bromoxynil, butachlor,
- Etobenzanide fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-butyl, fluazifop-p-butyl, fluazolates,
- Isoxachlorotol isoxaflutole, ketospiradox, lactofen, lenacil, linuron, MCPA, mecoprop, mecoprop-P, mefenacet, mesosulfuron-methyl, mesotrione, metamifop, metamitron, metazachlor,
- the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, soil or
- Spreading granulates and sprayable solutions are usually no longer diluted with other inert substances before use.
- Corn seeds were placed in sandy loam in wood fiber pots and covered with soil.
- the herbicidal safener combinations according to the invention formulated as water-soluble powders or suspensions and the correspondingly formulated herbicidal individual active compounds were applied to the surface of the cover soil in various dosages with a water charge of 300 l / ha and with the addition of the customary wetting agents and adjuvants sprayed. After the treatment, the pots were kept in the greenhouse under good growth conditions for the crops.
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
Description
Claims
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17169503 | 2017-05-04 | ||
| PCT/EP2018/060746 WO2018202544A1 (en) | 2017-05-04 | 2018-04-26 | Herbicide safener compositions containing quinazolinedione-6-carbonyl derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP3618620A1 true EP3618620A1 (en) | 2020-03-11 |
Family
ID=58669733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP18719897.3A Withdrawn EP3618620A1 (en) | 2017-05-04 | 2018-04-26 | Herbicide safener compositions containing quinazolinedione-6-carbonyl derivatives |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20200196601A1 (en) |
| EP (1) | EP3618620A1 (en) |
| JP (1) | JP2020518625A (en) |
| CN (1) | CN110582204A (en) |
| BR (1) | BR112019023009A2 (en) |
| WO (1) | WO2018202544A1 (en) |
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|---|---|---|---|---|
| CN112608282B (en) * | 2019-12-20 | 2022-07-26 | 山东先达农化股份有限公司 | Compound containing quinazolinedione and N-O structure and preparation method and application thereof |
| CN114573516B (en) * | 2020-11-30 | 2023-10-24 | 山东先达农化股份有限公司 | Trione-quinazolinone compound, preparation method and application thereof, and herbicide |
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2018
- 2018-04-26 EP EP18719897.3A patent/EP3618620A1/en not_active Withdrawn
- 2018-04-26 CN CN201880029040.5A patent/CN110582204A/en active Pending
- 2018-04-26 WO PCT/EP2018/060746 patent/WO2018202544A1/en not_active Ceased
- 2018-04-26 JP JP2019560288A patent/JP2020518625A/en active Pending
- 2018-04-26 US US16/610,043 patent/US20200196601A1/en not_active Abandoned
- 2018-04-26 BR BR112019023009A patent/BR112019023009A2/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN110582204A (en) | 2019-12-17 |
| WO2018202544A1 (en) | 2018-11-08 |
| US20200196601A1 (en) | 2020-06-25 |
| JP2020518625A (en) | 2020-06-25 |
| BR112019023009A2 (en) | 2020-05-19 |
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