WO1997031535A1 - Herbizide mittel auf basis von n-phosphonomethyl-glycinestern - Google Patents
Herbizide mittel auf basis von n-phosphonomethyl-glycinestern Download PDFInfo
- Publication number
- WO1997031535A1 WO1997031535A1 PCT/EP1997/000732 EP9700732W WO9731535A1 WO 1997031535 A1 WO1997031535 A1 WO 1997031535A1 EP 9700732 W EP9700732 W EP 9700732W WO 9731535 A1 WO9731535 A1 WO 9731535A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- group
- active ingredient
- ethyl
- active
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims abstract description 18
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical class OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims description 13
- 239000002253 acid Chemical group 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- -1 N-phosphonomethylglycine ester Chemical class 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000004480 active ingredient Substances 0.000 claims description 37
- 230000002363 herbicidal effect Effects 0.000 claims description 20
- 241000196324 Embryophyta Species 0.000 claims description 15
- 239000013543 active substance Substances 0.000 claims description 14
- 230000002195 synergetic effect Effects 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- YQVMVCCFZCMYQB-UHFFFAOYSA-N Flamprop Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(O)=O)C(=O)C1=CC=CC=C1 YQVMVCCFZCMYQB-UHFFFAOYSA-N 0.000 claims description 8
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000005562 Glyphosate Substances 0.000 claims description 7
- LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 claims description 6
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 claims description 5
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 4
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 4
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 claims description 4
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 claims description 4
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 claims description 4
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 claims description 4
- WZZRJCUYSKKFHO-UHFFFAOYSA-N 2-(n-benzoyl-3,4-dichloroanilino)propanoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1N(C(C)C(O)=O)C(=O)C1=CC=CC=C1 WZZRJCUYSKKFHO-UHFFFAOYSA-N 0.000 claims description 4
- GQQIAHNFBAFBCS-UHFFFAOYSA-N 2-[2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-4-fluorophenoxy]acetic acid Chemical compound C1=C(Cl)C(OCC(=O)O)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F GQQIAHNFBAFBCS-UHFFFAOYSA-N 0.000 claims description 4
- OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 claims description 4
- ONNQFZOZHDEENE-UHFFFAOYSA-N 2-[5-(but-3-yn-2-yloxy)-4-chloro-2-fluorophenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione Chemical compound C1=C(Cl)C(OC(C)C#C)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F ONNQFZOZHDEENE-UHFFFAOYSA-N 0.000 claims description 4
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 claims description 4
- QEGVVEOAVNHRAA-UHFFFAOYSA-N 2-chloro-6-(4,6-dimethoxypyrimidin-2-yl)sulfanylbenzoic acid Chemical compound COC1=CC(OC)=NC(SC=2C(=C(Cl)C=CC=2)C(O)=O)=N1 QEGVVEOAVNHRAA-UHFFFAOYSA-N 0.000 claims description 4
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 claims description 4
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 claims description 4
- DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 claims description 4
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- 239000002890 Aclonifen Substances 0.000 claims description 4
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- 239000003666 Amidosulfuron Substances 0.000 claims description 4
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 claims description 4
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 4
- NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005469 Azimsulfuron Substances 0.000 claims description 4
- RRNIZKPFKNDSRS-UHFFFAOYSA-N Bensulide Chemical compound CC(C)OP(=S)(OC(C)C)SCCNS(=O)(=O)C1=CC=CC=C1 RRNIZKPFKNDSRS-UHFFFAOYSA-N 0.000 claims description 4
- JDWQITFHZOBBFE-UHFFFAOYSA-N Benzofenap Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=C(C)C=C1 JDWQITFHZOBBFE-UHFFFAOYSA-N 0.000 claims description 4
- 239000005484 Bifenox Substances 0.000 claims description 4
- DXXVCXKMSWHGTF-UHFFFAOYSA-N Chlomethoxyfen Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 DXXVCXKMSWHGTF-UHFFFAOYSA-N 0.000 claims description 4
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- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 claims description 4
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- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
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- GPGLBXMQFQQXDV-UHFFFAOYSA-N Primisulfuron Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 GPGLBXMQFQQXDV-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 241000218206 Ranunculus Species 0.000 description 1
- 241000490453 Rorippa Species 0.000 description 1
- 241000341978 Rotala Species 0.000 description 1
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- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000273618 Sphenoclea zeylanica Species 0.000 description 1
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- HWUMSCCBZRLURP-UHFFFAOYSA-N [(2-ethoxy-2-oxoethyl)amino]methylphosphonic acid;hydrochloride Chemical compound Cl.CCOC(=O)CNCP(O)(O)=O HWUMSCCBZRLURP-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012364 cultivation method Methods 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000010902 jet-milling Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
Definitions
- the invention relates to new herbicidal compositions which consist of pure - not formulated - N-phosphonomethylglycine esters and dissolved or dispersed in water - previously formulated - other known, herbicidally active compounds or combinations of such known, herbicidally active compounds getting produced.
- N-phosphonomethylglycine alkyl esters have herbicidal properties and - generally in formulated use forms, ie combined with certain additives - can be used to kill unwanted plants (cf. DE 2152826, DE 2166573, US) 3977860). That pure - i.e. active ingredients which are not formulated - are used in spray liquors, but is not common.
- N-phosphonomethylglycine esters of the general formula (I) N-phosphonomethylglycine esters of the general formula (I)
- R represents alkyl
- the invention thus relates to herbicidal compositions, characterized by an effective content of a synergistic active ingredient combination consisting of (a) an N-phosphonomethylglycine ester of the above formula (I), in which R represents alkyl, or an acid adduct of these compounds (“active ingredient of group 1”) and
- N-phosphonomethylglycine esters of the general formula (I) - and acid adducts of compounds of the formula (I) - in pure, non-formulated form for use in spray liquors of known, formulated herbicidal active compounds can be used and that these spray liquors show extremely synergistic properties in comparison with corresponding application forms of the individual active ingredients.
- N-phosphonomethylglycine esters of the formula (I) directly in spray liquors without the use of formulation auxiliaries is a significant simplification of the application and thus a valuable enrichment of the prior art.
- the invention preferably relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
- R represents straight-chain or branched alkyl having 1 to 10 carbon atoms
- Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos,
- Fluoroglycofen (-ethyl), flupoxam, flupropacil, flurenol (n-butyl ester), fluridone, fluroxypyr, flurprimidol, flurtamone, fomesafen, glufosinate (-ammonium), glyphosate, haloxyfop (-ethoxyethyl), hexazinone, imazamethylbenzene , Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil,
- Tebutam Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thi- diazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallates, triasulfuron, tribenuron (-methyl), tricyclopyr, tridiphane, trifluralin, triflusulfuron,
- the invention particularly relates to herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
- R represents straight-chain or branched alkyl having 2 to 4 carbon atoms
- Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate-Bensulfuron (Bensulfuron)
- a particularly preferred group 1 active ingredient is N-phosphonomethylglycine ethyl ester
- Suitable acids are preferably strong protonic acids, such as hydrogen fluoride, hydrogen chloride (hydrochloric acid), hydrogen bromide, hydrogen iodide, sulfuric acid, phosphoric acid, trifluoroacetic acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid, and tonic sulfonic acid, tolonsulfonic acid, tolonsulfonic acid, tolonsulfonic acid
- N-phosphonomethylglycine esters of the general formula (I) are obtained if N-phosphonomethylglycine of the formula (II)
- an acid such as, for example, hydrogen chloride (hydrogen chloride)
- an acid binder such as e.g. triethylamine or propylene oxide
- herbicidal compositions to be used according to the invention can be used both in conventional cultivation methods (row crops with a suitable row width) in plantation crops (for example wine, fruit, citrus) and in industrial and track systems, on paths and squares, but also for stubble treatment and for minimum
- Tillage processes are used. They are also suitable as burners (killing herbs, e.g. in potatoes) or as defoliants (e.g. in cotton). They are also suitable for use on fallow land. Further areas of application are tree nurseries, forestry, grassland and ornamental plant cultivation
- Scirpus Papalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera
- the use of the active compounds and combinations of active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants
- the synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios.
- the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 1 part by weight of active ingredient in group 1 accounts for 0.001 to 1000 parts by weight, preferably 0.01 to
- the application rates of the active compound combinations according to the invention can be varied within a certain range; they hang among other things depending on the weather and soil factors.
- the application rates are between 0.05 and 5 kg of active ingredient combination per ha, preferably between 0.06 and 2 kg per ha, particularly preferably between 0.1 and 1.0 kg per ha.
- the active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence processes. However, they are preferably used in the post-emergence process.
- a herbicide always has a synergistic effect if the herbicidal action of the active compound combination is greater than that of the individual applied active compounds.
- the effect of the combination is super-additive, that is, it shows a synergistic effect.
- Hydrogen chloride gas is introduced into a suspension of 200 g (1.2 mol) of N-phosphonomethylglycine in 3000 ml of ethanol until saturation. Then the
- Fluid bed drying, blade drying or circulating air drying in each case combined with conventional comminution processes, such as air jet milling, crushers, rollers, grinding, if appropriate).
- Hydrogen chloride gas is introduced into a suspension of 5.1 g (30 mmol) of N-phosphonomethyl-glycine in 80 ml of ethanol until saturation.
- the reaction mixture is heated under reflux for 2 hours and then concentrated in a water jet vacuum.
- the residue is mixed with acetone stirred and the kristal ⁇ line product isolated by suction
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Die Erfindung betrifft neue herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer synergistischen Wirkstoffkombination bestehend aus (a) einem N-Phosphonomethyl-glycinester der Formel (I): (HO)2P(O)-CH2-NH-CH2-CO-O-R, in welcher R für Alkyl steht, oder einem Säureaddukt dieser Verbindungen ('Wirkstoff der Gruppe 1') und (b) wenigstens einer Verbindung aus der Gruppe der übrigen bekannten Herbizide ('Wirkstoff der Gruppe 2'), wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,001 bis 1000 Gewichtsteile Wirkstoff der Gruppe 2 entfallen.
Description
Herbizide Mittel auf Basis von N-Phosphonomethyl-glvcinestern
Die Erfindung betrifft neue herbizide Mittel, welche aus reinen - nicht formulierten - N-Phosphonomethyl-glycinestern und in Wasser gelösten oder dis¬ pergierten - vorher formulierten - anderen bekannten, herbizid wirksamen Ver¬ bindungen oder Kombinationen von solchen bekannten, herbizid wirksamen Ver¬ bindungen hergestellt werden.
Es ist bekannt, daß einige N-Phosphonomethyl-glycin-alkylester herbizide Eigen- schaften aufweisen und - im allgemeinen in formulierten Anwendungsformen, d.h mit bestimmten Zuschlagsstoffen kombiniert - zur Abtötung von unerwünschten Pflanzen verwendet werden können (vgl. DE 2152826, DE 2166573, US 3977860). Daß reine - d.h. nicht formulierte Wirkstoffe - in Spritzbrühen zur An¬ wendung kommen, ist jedoch nicht üblich.
Es wurde nun gefunden, daß N-Phosphonomethyl-glycinester der allgemeinen For¬ mel (I),
(HO)2P(O)-CH2-NH-CH2-CO-O-R (I)
in welcher
R für Alkyl steht,
- sowie Säureaddukte von Verbindungen der Formel (I) -
als reine Wirkstoffe, d.h. ohne Verwendung weiterer Hilfsstoffe, zu Spritzbruhen von bekannten Herbiziden gegeben werden können und die so hergestellten An¬ wendungsformen mit sehr gutem Erfolg zur Abtötung unerwünschter Pflanzen ver¬ wendet werden können, wobei synergistische Effekte zu beobachten sind
Gegenstand der Erfindung sind somit herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer synergistischen Wirkstoffkombination bestehend aus
(a) einem N-Phosphonomethyl-glycinester der obigen Formel (I), in welcher R für Alkyl steht, oder einem Säureaddukt dieser Verbindungen ("Wirkstoff der Gruppe 1 ") und
(b) wenigstens einer Verbindung aus der Gruppe der übrigen bekannten Herbizide ("Wirkstoff der Gruppe 2"),
wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,001 bis 1000 Ge¬ wichtsteile Wirkstoff der Gruppe 2 entfallen.
Es ist als ausgesprochen überraschend anzusehen, daß N-Phosphonomethyl-glycin¬ ester der allgemeinen Formel (I) - sowie Säureaddukte von Verbindungen der Formel (I) - in reiner, nicht formulierter Form zur Anwendung in Spritzbrühen be¬ kannter, formulierter Herbizid-Wirkstoffe eingesetzt werden können und daß diese Spritzbrühen im Vergleich mit entsprechenden Anwendungsformen der einzelnen Wirkstoffe ausgesprochen synergistische Eigenschaften zeigen.
Die Möglichkeit, die N-Phosphonomethyl-glycinester der Formel (I) ohne Ver- wendung von Formulierungshilfsmitteln direkt in Spritzbrühen einzusetzen, stellt eine wesentliche Vereinfachung der Anwendung und somit eine wertvolle Be¬ reicherung des Standes der Technik dar.
Gegenstand der Erfindung sind vorzugsweise herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer Wirkstoffkombination bestehend aus
(a) einem N-Phosphonomethyl-glycinester der allgemeinen Formel (I),
(HO)2P(O)-CH2-NH-CH2-CO-O-R (I)
in welcher
R für geradkettiges oder verzweigtes Alkyl mit 1 bis 10 Kohlenstoffatomen steht,
("Wirkstoff der Gruppe 1 ") und
(b) einer oder zwei Verbindungen aus einer zweiten Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe (jeweils mit "common name" benannt) enthält:
Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos,
Asulam, Atrazin, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl), Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butami- fos, Butenachlor, Butylate, Cafenstrole, Carbetamide, Chlom ethoxy fen, Chlor- amben, Chloridazon, Chlorimuron (-ethyl), Chlormethoxynil, Chlornitrofen, Chlor- sulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cy- halofop (-butyl), 2,4-D, Desmedipham, Dicamba, Dichlorprop, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimetha¬ metryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron (Daimuron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxaprop (-ethyl), Flamprop (-isopropyl), Flamprop (-methyl), Flazasulfuron, Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone,
Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurenol (n-butylester), Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Gly- phosate, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imaza- methapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil,
Linuron, MCPA, Mecoprop, Mefenacet, Metamitron, Metazachlor, Methabenz¬ thiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop- amide, Neburon, Nicosulfuron, Nitrofen, Norflurazon, Orbencarb, Oryzalin, Oxa- diargyl, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phenmedipham, Pipero- phos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate,
Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thi-
diazimin, Thifensulfuron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Tri- allate, Triasulfuron, Tribenuron (-methyl), Tricyclopyr, Tridiphane, Trifluralin, Tri- flusulfuron,
("Wirkstoffe der Gruppe 2")
wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,01 bis 100 Gewichts¬ teile Wirkstoff der Gruppe 2 entfallen.
Gegenstand der Erfindung sind insbesondere herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer Wirkstoffkombination bestehend aus
(a) einem N-Phosphonomethyl-glycinester der allgemeinen Formel (I)
(HO)2P(O)-CH2-NH-CH2-CO-O-R (I)
in welcher
R für geradkettiges oder verzweigtes Alkyl mit 2 bis 4 Kohlenstoff atomen steht,
("Wirkstoff der Gruppe 1 ") und
(b) einer oder zwei Verbindungen aus einer zweiten Gruppe von Herbiziden, welche die nachstehend genannten Wirkstoffe (jeweils mit "common name" be¬ nannt) enthält:
Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos, Asulam, Atrazin, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl),
Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butami- fos, Butenachlor, Butylate, Cafenstrole, Carbetamide, Chlomethoxyfen, Chlor¬ amben, Chloridazon, Chlorimuron (-ethyl), Chl orm ethoxy nil, Chlornitrofen, Chlor- sulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop
(-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cy-
halofop (-butyl), 2,4-D, Desmedipham, Dicamba, Dichlorprop, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimetha¬ metryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron (Daimuron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxaprop (-ethyl), Flamprop
(-isopropyl), Flamprop (-methyl), Flazasulfuron, Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurenol (n-butylester), Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Gly- phosate, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imaza- methapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Metamitron, Metazachlor, Methabenz¬ thiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop- amide, Neburon, Nicosulfuron, Nitrofen, Norflurazon, Orbencarb, Oryzalin, Oxa- diargyl, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phenmedipham, Pipero- phos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac,
Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thi- diazimin, Thifensulfuron (-methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Tri- allate, Triasulfuron, Tribenuron (-methyl), Tricyclopyr, Tridiphane, Trifluralin, Tri- flusulfuron,
("Wirkstoffe der Gruppe 2")
wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,05 bis 50 Gewichtsteile Wirkstoff der Gruppe 2 entfallen.
Als ganz besonders bevorzugter Wirkstoff der Gruppe 1 sei N-Phosphonomethyl- glycin-ethylester genannt
Als Säureaddukte sind im Zusammenhang mit der vorliegenden Erfindung all¬ gemein Additionsprodukte aus Verbindungen der Formel (I) und Sauren zu ver-
stehen Geeignete Sauren sind hierbei vorzugsweise starke Protonensauren, wie z B Hydrogenfluoπd, Hydrogenchloπd (Salzsaure), Hydrogenbromid, Hydrogen- lodid, Schwefelsaure, Phosphorsaure, Trifluoressigsaure, Methansulfonsäure, Ethansulfonsaure, Propansulfonsaure, Butansulfonsaure, Tπfluormethansulfonsaure, Benzolsulfonsaure und p-Toluolsulfonsaure
Die erfindungsgemaß zu verwendenden Verbindungen der Formel (I) sind bereits bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl DE 2152826, DE 2166573, US 3977860)
Man erhalt die N-Phosphonomethyl-glycinester der allgemeinen Formel (I), wenn man N-Phosphonomethyl-glycin der Formel (II)
(HO)2P(O)-CH2-NH-CH2-COOH (II)
mit einem Alkohol der Formel (III)
HO-R (III)
in welcher
R die oben angegebene Bedeutung hat,
in Gegenwart einer Saure, wie z B Hydrogenchloπd (Chlorwasserstoff), bei Tem¬ peraturen zwischen 40°C und 150°C umsetzt und das hierbei gebildete Säure¬ addukt der Verbindung der Formel (I) - gegebenenfalls nach Zwischenisolierung - mit einem Saurebindemittel, wie z B Triethylamin oder Propylenoxid, bei Temperaturen zwischen 0°C und 60°C umsetzt (vgl die Herstellungsbeispiele)
Es wurde nun überraschend gefunden daß die oben definierten Wirkstoffkombina- ttonen aus den N-Phosphonomethyl-glycinestern der Formel (I) und den oben auf¬ geführten Wirkstoffen der Gruppe 2 eine besonders hohe herbizide Wirksamkeit aufweisen Sie können insbesondere mit sehr gutem Erfolg im semi-selektiven und im nicht-selektiven Bereich der Unkrautbekämpfung eingesetzt werden
Uberraschenderweise ist die herbizide Wirksamkeit der erfindungsgemäßen Wirk¬ stoffkombinationen aus den Verbindungen der oben aufgeführten Gruppen 1 und 2 erheblich höher als die Summe der Wirkungen der einzelnen Wirkstoffe
Es liegt somit ein nicht vorhersehbarer synergistischer Effekt vor und nicht nur eine Wirkungserganzung Die neuen Wirkstoffkombinationen und Anwendungsfor¬ men stellen somit eine wertvolle Bereicherung des Standes der Technik dar
Die erfindungsgemäß zu verwendenden herbiziden Mittel können sowohl in kon¬ ventionellen Anbauverfahren (Reihenkulturen mit geeigneter Reihenweite) in Plantagenkulturen (z B Wein, Obst, Zitrus) sowie in Industrie- und Gleisanlagen, auf Wegen und Platzen, aber auch zur Stoppelbehandlung und beim Minimum-
Tillage-Verfahren eingesetzt werden Sie eignen sich weiterhin als Abbrenner (Krautabtotung z.B in Kartoffeln) oder als Defoliantien (z B in Baumwolle) Ferner sind sind sie für den Einsatz auf Bracheflachen geeignet Weitere Einsatz¬ gebiete sind Baumschulen, Forst, Grünland und Zierpflanzenbau
Als Unkräuter, die durch die erfindungsgemaßen Wirkstoffe bzw Wirkstoffkom¬ binationen gut bekämpft werden können, seien beispielsweise genannt
Dikotyle Unkräuter der Gattungen Sinapis, Lepidium, Galium, Stellaria, Matri- caπa, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Soianum, Cirsium, Carduus, Sonchus, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abu- tilon, Emex, Sida, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranun- culus, Taraxum, Mentha
Monokotyle Unkräuter der Gattungen Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorhum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleochaπs,
Scirpus, Papalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera
Die Verwendung der erfindungsgemaßen Wirkstoffe und Wirkstoffkombinationen ist jedoch keineswegs auf diese Gattungen beschrankt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen
Der synergistische Effekt der erfindungsgemäßen Wirkstoffkombinationen ist bei bestimmten Konzentrationsverhältnissen besonders stark ausgeprägt. Jedoch kön¬ nen die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in relativ großen Bereichen variiert werden. Im allgemeinen entfallen auf 1 Gewichts- teil Wirkstoff der Gruppe 1 0,001 bis 1000 Gewichtsteile, vorzugsweise 0,01 bis
100 Gewichtsteile und besonders bevorzugt 0,05 bis 50 Gewichtsteile Wirkstoff der Gruppe 2.
Die Aufwandmengen der erfindungsgemäßen Wirkstoffkombinationen können in einem gewissen Bereich variiert werden; sie hängen u.a. vom Wetter und von den Bodenfaktoren ab. Im allgemeinen liegen die Aufwandmengen zwischen 0,05 und 5 kg Wirkstoffkombination pro ha, vorzugsweise zwischen 0,06 und 2 kg pro ha, besonders bevorzugt zwischen 0,1 und 1,0 kg pro ha.
Die erfindungsgemäßen Wirkstoffkombinationen können vor und nach dem Auf¬ laufen der Pflanzen appliziert werden, also im Vorauflauf- und Nachauflauf- Ver- fahren. Sie werden jedoch vorzugsweise im Nachauflauf-Verfahren angewandt.
Die gute herbizide Wirkung der neuen Wirkstoffkombinationen geht aus den nach¬ folgenden Beispielen hervor. Während die einzelnen Wirkstoffe in der herbiziden Wirkung Schwächen aufweisen, zeigen die Kombinationen durchweg eine sehr gute Unkrautwirkung, die über eine einfache Wirkungssummierung hinausgeht.
Ein synergistischer Effekt liegt bei Herbiziden immer dann vor, wenn die herbi¬ zide Wirkung der Wirkstofϊkombination größer ist als die der einzelnen applizier¬ ten Wirkstoffe.
Die zu erwartende Wirkung für eine gegebene Kombination zweier Herbizide kann wie folgt berechnet werden (vgl COLBY, S.R.: "Calculating sy- nergistic and antagonistic responses of herbicide combinations",
Weeds 15, Seiten 20 - 22, 1967) Wenn X = % Schädigung durch Herbizid A (Wirkstoff der Gruppe 1) bei p kg/ha Aufwandmenge und Y = % Schädigung durch Herbizid B (Wirkstoff der Gruppe 2) bei q kg/ha Aufwandmenge und E = die erwartete Schädigung der Herbizide A und B bei p und q kg/ha Aufwandmenge,
dann ist E = X + Y - (X * Y/100).
Ist die tatsächliche Schädigung größer als berechnet, so ist die Kombination in ihrer Wirkung überadditiv, das heißt, sie zeigt einen synergistischen Effekt.
Entsprechende biologische Tests zeigten, daß die herbizide Wirkung der erfin- dungsgemäßen Wirkstoffkombinationen bei den Unkräutern größer ist als die be¬ rechnete, das heißt, daß die neuen Wirkstoffkombinationen synergistisch wirken.
Herstellungsbeispiele:
Beispiel 1
(HO)2P(O)-CH2-NH-CH2-CO-O-C2H5
In eine Suspension von 200 g (1,2 Mol) N-Phosphonomethyl-glycin in 3000 ml Ethanol wird Chlorwasserstoff-Gas bis zur Sättigung eingeleitet. Dann wird die
Reaktionsmischung 3 Stunden unter Rückfluß erhitzt und anschließend - nach Ab¬ kühlen auf Raumtemperatur - im Wasserstrahlvakuum eingeengt. Der Rückstand wird in 1500 ml Ethanol gelöst und zu dieser Lösung wird Triethylamin (ca. 140 g) tropfenweise gegeben, bis ein Farbumschlag von rötlich-braun nach hellgelb er- folgt Das hierbei kristallin anfallende Produkt wird durch Absaugen isoliert
Man erhält 201 g (85% der Theorie) N-Phosphonomethyl-glycin-ethylester vom Schmelzpunkt 203°C.
Die "Trocknung" des gemäß Beispiel 1 erhaltenen Produktes - d.h. die Entfernung des Alkohols - kann - gegebenenfalls mit technisch üblichen Zerkleinerungsver- fahren kombiniert - beispielsweise nach folgenden, technisch üblichen Methoden erfolgen'
Wirbelschichttrocknung, Schaufel trocknung oder Umlufttrocknung (jeweils gegebe¬ nenfalls mit technisch üblichen Zerkleinerungsverfahren, wie z.B. Luftstrahlmah¬ lung, Brechern, Walzen, Mahlen kombiniert).
Beispiel 2
(HO)2P(O)-CH2-NH-CH2-CO-O-C2H5 x HCl
In eine Suspension von 5,1 g (30 mMol) N-Phosphonomethyl-glycin in 80 ml Ethanol wird Chlorwasserstoff-Gas bis zur Sättigung eingeleitet Dann wird die Reaktionsmischung 2 Stunden unter Ruckfluß erhitzt und anschließend im Wasser¬ strahlvakuum eingeengt Der Ruckstand wird mit Aceton verrührt und das kristal¬ line Produkt durch Absaugen isoliert
Man erhalt 3,0 g (43% der Theorie) N-Phosphonomethyl-glycin-ethylester-Hydro- chloπd als hygroskopische Kristalle, welche beim Erhitzen zerfließen
Claims
Patentansprüche
1 Herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an einer synergistischen Wirkstoffkombination bestehend aus
(a) einem N-Phosphonomethyl-glycinester der Formel (I),
(HO)2P(O)-CH2-NH-CH2-CO-O-R (I)
in welcher
R für Alkyl steht,
oder einem Säureaddukt dieser Verbindungen ("Wirkstoff der Grup¬ pe 1 ") und
(b) wenigstens einer Verbindung aus der Gruppe der übrigen bekannten
Herbizide ("Wirkstoff der Gruppe 2"),
wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,001 bis 1000 Gewichtsteile Wirkstoff der Gruppe 2 entfallen
2 Herbizide Mittel nach Anspruch 1, gekennzeichnet durch einen wirksamen Gehalt an einer Wirkstoffkombination bestehend aus
(a) einem N-Phosphonomethyl-glycinester der allgemeinen Formel (I),
(HO)2P(O)-CH2-NH-CH2-CO-O-R (I)
in welcher
R für geradkettiges oder verzweigtes Alkyl mit 1 bis 10 Kohlenstoff- atomen steht,
("Wirkstoff der Gruppe 1 ") und
(b) einer oder zwei Verbindungen aus einer zweiten Gruppe von Herbi¬ ziden, welche die nachstehend genannten Wirkstoffe (jeweils mit "common name" benannt) enthält:
Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl),
Amitrol, Anilofos, Asulam, Atrazin, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl), Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromo- fenoxim, Bromoxynil, Butachlor, Butamifos, Butenachlor, Butylate, Cafen- strole, Carbetamide, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimu- ron (-ethyl), Chlormethoxynil, Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazo¬ ne, Clomeprop, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyl- uron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, Desmedipham, Dicamba, Dichlorprop, Diclofop (-methyl),
Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Di¬ methametryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron (Daimuron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxa- prop (-ethyl), Flamprop (-isopropyl), Flamprop (-methyl), Flazasulfuron,
Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumi- propyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurenol (n-butylester), Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Glyphosate, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr,
Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Iso- propalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Meto- sulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Mono- linuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Nitrofen, Nor- flurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxyfluorfen, Para- quat, Pendimethalin, Phenmedipham, Piperophos, Pretilachlor, Primi¬ sulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Pro- pyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyi),
Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac,
Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Seth- oxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thioben- carb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-me¬ thyl), Tricyclopyr, Tridiphane, Trifluralin, Triflusulfuron,
("Wirkstoffe der Gruppe 2"),
wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,01 bis 100 Ge¬ wichtsteile Wirkstoff der Gruppe 2 entfallen.
Herbizide Mittel nach Anspruch 1 , gekennzeichnet durch einen wirksamen
Gehalt an einer Wirkstoffkombination bestehend aus
(a) einem N-Phosphonomethyl-glycinester der allgemeinen Formel (I)
(HO)2P(O)-CH2-NH-CH2-CO-O-R (I)
in welcher
R für geradkettiges oder verzweigtes Alkyl mit 2 bis 4 Kohlenstoff¬ atomen steht,
("Wirkstoff der Gruppe 1 ") und
(b) einer oder zwei Verbindungen aus einer zweiten Gruppe von Herbi¬ ziden, welche die nachstehend genannten Wirkstoffe (jeweils mit "common name" benannt) enthält:
Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-so¬ dium), Ametryne, Amidochlor, Amidosulfuron, Amiprophos (-methyl), Amitrol, Anilofos, Asulam, Atrazin, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl), Bensulide, Bentazon, Benthiocarb, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bromacil, Bromobutide, Bromo- fenoxim, Bromoxynil, Butachlor, Butamifos, Butenachlor, Butylate, Cafen- strole, Carbetamide, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimu-
ron (-ethyl), Chlormethoxynil, Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazo¬ ne, Clomeprop, Clopyralid, Clopyrasulfuron, Cloransulam (-methyl), Cumyl- uron, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, Desmedipham, Dicamba, Dichlorprop, Diclofop (-methyl),
Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Di¬ methametryn, Demethenamid, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron (Daimuron, Dimuron), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxa- prop (-ethyl), Flamprop (-isopropyl), Flamprop (-methyl), Flazasulfuron,
Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumi- propyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurenol (n-butylester), Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Glyphosate, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr,
Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Iso- propalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Meto- sulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Mono- linuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Nitrofen, Nor- flurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxyfluorfen, Para- quat, Pendimethalin, Phenmedipham, Piperophos, Pretilachlor, Primi¬ sulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Pro- pyzamide, Prosulfocarb, Prosulfuron, Pyrazolate, Pyrazosulfuron (-ethyl),
Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuryl), Rimsulfuron, Seth- oxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thioben- carb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-me¬ thyl), Tricyclopyr, Tridiphane, Trifluralin, Triflusulfuron,
("Wirkstoffe der Gruppe 2"),
wobei auf 1 Gewichtsteil Wirkstoff der Gruppe 1 jeweils 0,05 bis 50 Ge- wichtsteile Wirkstoff der Gruppe 2 entfallen
Herbizide Mittel nach Anspruch 1, dadurch gekennzeichnet, daß sie als Wirkstoff der Gruppe 1 N-Phosphonomethylglycin-ethylester enthalten
Verwendung von Wirkstoffkombinationen gemäß Ansprüchen 1-4 zur Be¬ kämpfung von Unkraut
Verfahren zur Bekämpfung von Unkraut, dadurch gekennzeichnet, daß man eine Wirkstoffkombination gemäß Ansprüchen 1-4 auf Unkraut oder seinen Lebensraum einwirken laßt
Verfahren nach Anspruch 6, dadurch gekennzeichnet, daß man die Wirk- stoffkombinationen in Aufwandmengen zwischen 0,05 und 5 kg pro ha, vorzugsweise zwischen 0,06 und 2 kg pro ha, besonders bevorzugt zwi¬ schen 0, 1 und 1 ,0 kg pro ha anwendet
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU18737/97A AU1873797A (en) | 1996-02-29 | 1997-02-17 | Herbicidal agents based on n-phosphonomethylglycine esters |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19607633.1 | 1996-02-29 | ||
| DE1996107633 DE19607633A1 (de) | 1996-02-29 | 1996-02-29 | Herbizide Mittel auf Basis von N-Phosphonomethyl-glycinestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1997031535A1 true WO1997031535A1 (de) | 1997-09-04 |
Family
ID=7786751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1997/000732 WO1997031535A1 (de) | 1996-02-29 | 1997-02-17 | Herbizide mittel auf basis von n-phosphonomethyl-glycinestern |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU1873797A (de) |
| DE (1) | DE19607633A1 (de) |
| WO (1) | WO1997031535A1 (de) |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000074487A1 (fr) * | 1999-06-07 | 2000-12-14 | Sumitomo Chemical Company, Limited | Composition herbicide |
| US6369001B1 (en) | 1999-08-11 | 2002-04-09 | Monsanto Technology, Llc | Microemulsion coformulation of a graminicide and a water-soluble herbicide |
| US6451732B1 (en) * | 1999-06-04 | 2002-09-17 | Syngenta, Limited | Herbicidal compositions of glyphosate trimesium |
| DE10157339A1 (de) * | 2001-11-22 | 2003-06-12 | Bayer Cropscience Gmbh | Synergistische herbizide Mittel enthaltend Herbizide aus der Gruppe der Benzoylpyrazole |
| US7008904B2 (en) | 2000-09-13 | 2006-03-07 | Monsanto Technology, Llc | Herbicidal compositions containing glyphosate and bipyridilium |
| US7422998B2 (en) * | 1998-08-13 | 2008-09-09 | Aventis Cropscience Gmbh | Herbicidal compositions for tolerant or resistant sugar beet crops |
| JP2009001578A (ja) * | 1996-09-05 | 2009-01-08 | Syngenta Participations Ag | 雑草の抑制方法 |
| EP2319317A1 (de) * | 1998-08-13 | 2011-05-11 | Bayer CropScience AG | Herbizide Mittel für tolerante oder resistente Baumwollkulturen |
| EP2327305A1 (de) * | 1998-08-13 | 2011-06-01 | Bayer CropScience AG | Herbizide Mittel für tolerante oder resistente Sojakulturen |
| US8324132B2 (en) | 2010-03-31 | 2012-12-04 | E. I. Du Pont De Nemours And Company | Mixture and method for controlling undesired vegetation |
| US8536094B2 (en) | 1998-08-13 | 2013-09-17 | Bayer Intellectual Property Gmbh | Herbicidal compositions for tolerant or resistant rice crops |
| US8815773B2 (en) | 2009-07-29 | 2014-08-26 | Upl Limited | Herbicidal combination |
| WO2015170876A1 (ko) * | 2014-05-07 | 2015-11-12 | 선문그린사이언스 주식회사 | 다이쿼트디브로마이드와 비선택성 제초제를 포함하는 상승작용적 제초제 혼합물 |
| US10285404B2 (en) | 2013-02-27 | 2019-05-14 | Monsanto Technology Llc | Glyphosate composition for dicamba tank mixtures with improved volatility |
| US10334849B2 (en) | 2011-10-26 | 2019-07-02 | Monsanto Technology Llc | Salts of carboxylic acid herbicides |
| US10499646B2 (en) | 2004-03-10 | 2019-12-10 | Monsanto Technology Llc | Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide |
| US10736322B2 (en) | 2012-06-04 | 2020-08-11 | Monsanto Technology Llc | Aqueous concentrated herbicidal compositions containing glyphosate salts and dicamba salts |
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|---|---|---|---|---|
| US3799758A (en) * | 1971-08-09 | 1974-03-26 | Monsanto Co | N-phosphonomethyl-glycine phytotoxicant compositions |
| US3929450A (en) * | 1974-06-28 | 1975-12-30 | Monsanto Co | Herbicidal compositions and methods |
| WO1984003607A1 (en) * | 1983-03-16 | 1984-09-27 | Chevron Res | Glyphosate-type herbicidal compositions |
| EP0143547A1 (de) * | 1983-10-28 | 1985-06-05 | Chevron Research Company | Herbizide Zusammensetzungen der Art Glyphosate und deren Verwendung |
| EP0162326A2 (de) * | 1984-05-02 | 1985-11-27 | Hoechst Aktiengesellschaft | Herbizide Mittel |
| GB2169806A (en) * | 1985-01-23 | 1986-07-23 | Rhone Poulenc Agrochimie | Herbicidal mixtures based on n-(phosphonomethylglycyl)sulphonylamine |
| EP0281103A2 (de) * | 1987-03-05 | 1988-09-07 | Teijin Limited | Phenoxycarbonsäureverbindungen und diese als Aktivsubstanz enthaltendes Unkrautvertilgungsmittel |
| WO1989003641A1 (fr) * | 1987-10-28 | 1989-05-05 | Rhone Poulenc Agrochimie | Compositions comprenant des combinaisons d'herbicides de type glyphosate et de type phenoxybenzoique |
| DE19528056A1 (de) * | 1995-07-31 | 1997-02-06 | Bayer Ag | Iso-Butylester und sec-Butylester von N-Phosphonomethyl-glycin |
| DE19533523A1 (de) * | 1995-09-11 | 1997-03-13 | Bayer Ag | Verwendung von N-Phosphonomethyl-glycinestern in wäßriger Lösung als Herbizide |
-
1996
- 1996-02-29 DE DE1996107633 patent/DE19607633A1/de not_active Withdrawn
-
1997
- 1997-02-17 WO PCT/EP1997/000732 patent/WO1997031535A1/de active Application Filing
- 1997-02-17 AU AU18737/97A patent/AU1873797A/en not_active Abandoned
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|---|---|---|---|---|
| JP2009001578A (ja) * | 1996-09-05 | 2009-01-08 | Syngenta Participations Ag | 雑草の抑制方法 |
| EP2327305A1 (de) * | 1998-08-13 | 2011-06-01 | Bayer CropScience AG | Herbizide Mittel für tolerante oder resistente Sojakulturen |
| EP2329719A1 (de) * | 1998-08-13 | 2011-06-08 | Bayer CropScience AG | Herbizide Mittel für tolerante oder resistente Sojakulturen |
| EP2327306A1 (de) * | 1998-08-13 | 2011-06-01 | Bayer CropScience AG | Herbizide Mittel für tolerante oder resistente Baumwollkulturen |
| EP2319317A1 (de) * | 1998-08-13 | 2011-05-11 | Bayer CropScience AG | Herbizide Mittel für tolerante oder resistente Baumwollkulturen |
| EP1107668B2 (de) † | 1998-08-13 | 2018-10-03 | Bayer CropScience AG | Herbizide mittel für tolerante oder resistente zuckerrübenkulturen |
| EP2329718A1 (de) * | 1998-08-13 | 2011-06-08 | Bayer CropScience AG | Herbizide Mittel für tolerante oder resistente Sojakulturen |
| US7422998B2 (en) * | 1998-08-13 | 2008-09-09 | Aventis Cropscience Gmbh | Herbicidal compositions for tolerant or resistant sugar beet crops |
| US8536094B2 (en) | 1998-08-13 | 2013-09-17 | Bayer Intellectual Property Gmbh | Herbicidal compositions for tolerant or resistant rice crops |
| US6451732B1 (en) * | 1999-06-04 | 2002-09-17 | Syngenta, Limited | Herbicidal compositions of glyphosate trimesium |
| US6576592B1 (en) | 1999-06-07 | 2003-06-10 | Sumitomo Chemical Company, Limited | Herbicide composition |
| EP1183949A4 (de) * | 1999-06-07 | 2002-09-25 | Sumitomo Chemical Co | Herbizidzusammensetzung |
| WO2000074487A1 (fr) * | 1999-06-07 | 2000-12-14 | Sumitomo Chemical Company, Limited | Composition herbicide |
| US6369001B1 (en) | 1999-08-11 | 2002-04-09 | Monsanto Technology, Llc | Microemulsion coformulation of a graminicide and a water-soluble herbicide |
| CN100512643C (zh) * | 1999-08-11 | 2009-07-15 | 孟山都技术有限责任公司 | 禾本科除草剂和水溶性除草剂的微乳合剂 |
| US7989392B2 (en) * | 2000-09-13 | 2011-08-02 | Monsanto Technology, Llc | Herbicidal compositions containing glyphosate bipyridilium |
| US7008904B2 (en) | 2000-09-13 | 2006-03-07 | Monsanto Technology, Llc | Herbicidal compositions containing glyphosate and bipyridilium |
| CN101326914B (zh) * | 2001-11-22 | 2012-10-10 | 拜尔作物科学股份公司 | 含有选自苯甲酰基吡唑类除草剂的增效除草组合物 |
| CN101485326A (zh) * | 2001-11-22 | 2009-07-22 | 拜尔作物科学股份公司 | 含有选自苯甲酰基吡唑类除草剂的增效除草组合物 |
| CN101326914A (zh) * | 2001-11-22 | 2008-12-24 | 拜尔作物科学股份公司 | 含有选自苯甲酰基吡唑类除草剂的增效除草组合物 |
| DE10157339A1 (de) * | 2001-11-22 | 2003-06-12 | Bayer Cropscience Gmbh | Synergistische herbizide Mittel enthaltend Herbizide aus der Gruppe der Benzoylpyrazole |
| US10499646B2 (en) | 2004-03-10 | 2019-12-10 | Monsanto Technology Llc | Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide |
| US11864558B2 (en) | 2004-03-10 | 2024-01-09 | Monsanto Technology Llc | Herbicidal compositions containing N-phosphonomethyl glycine and an auxin herbicide |
| US8815773B2 (en) | 2009-07-29 | 2014-08-26 | Upl Limited | Herbicidal combination |
| US8324132B2 (en) | 2010-03-31 | 2012-12-04 | E. I. Du Pont De Nemours And Company | Mixture and method for controlling undesired vegetation |
| US10334849B2 (en) | 2011-10-26 | 2019-07-02 | Monsanto Technology Llc | Salts of carboxylic acid herbicides |
| US10736322B2 (en) | 2012-06-04 | 2020-08-11 | Monsanto Technology Llc | Aqueous concentrated herbicidal compositions containing glyphosate salts and dicamba salts |
| US10285404B2 (en) | 2013-02-27 | 2019-05-14 | Monsanto Technology Llc | Glyphosate composition for dicamba tank mixtures with improved volatility |
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| WO2015170876A1 (ko) * | 2014-05-07 | 2015-11-12 | 선문그린사이언스 주식회사 | 다이쿼트디브로마이드와 비선택성 제초제를 포함하는 상승작용적 제초제 혼합물 |
| KR101615174B1 (ko) | 2014-05-07 | 2016-04-26 | 선문그린사이언스 주식회사 | 다이쿼트디브로마이드와 비선택성 제초제를 포함하는 상승작용적 제초제 혼합물 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19607633A1 (de) | 1997-09-04 |
| AU1873797A (en) | 1997-09-16 |
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