CH652888A5 - STABLE, LIQUID PREPARATION WITH HERBICIDAL EFFECT AND METHOD FOR THE PRODUCTION THEREOF. - Google Patents
STABLE, LIQUID PREPARATION WITH HERBICIDAL EFFECT AND METHOD FOR THE PRODUCTION THEREOF. Download PDFInfo
- Publication number
- CH652888A5 CH652888A5 CH5044/82A CH504482A CH652888A5 CH 652888 A5 CH652888 A5 CH 652888A5 CH 5044/82 A CH5044/82 A CH 5044/82A CH 504482 A CH504482 A CH 504482A CH 652888 A5 CH652888 A5 CH 652888A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dinitro
- atoms
- trifluoromethyl
- aniline
- urea
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 12
- 239000007788 liquid Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002904 solvent Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 16
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 claims description 16
- 239000003995 emulsifying agent Substances 0.000 claims description 9
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical class OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 8
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 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 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- VACNDKUQVLNNLD-UHFFFAOYSA-N 2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O VACNDKUQVLNNLD-UHFFFAOYSA-N 0.000 claims description 4
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical compound NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 239000008096 xylene Substances 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000001448 anilines Chemical class 0.000 claims 1
- -1 aliphatic ketones Chemical class 0.000 description 29
- 239000004480 active ingredient Substances 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- 229940078552 o-xylene Drugs 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000003738 xylenes Chemical class 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- 229920001214 Polysorbate 60 Polymers 0.000 description 3
- 150000004996 alkyl benzenes Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 3
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 3
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- XVKRTNZGYNJYQX-UHFFFAOYSA-N 5-ethylhept-4-en-3-one Chemical compound CCC(=O)C=C(CC)CC XVKRTNZGYNJYQX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical class CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- ARENMZZMCSLORU-UHFFFAOYSA-N propan-2-yl naphthalene-1-sulfonate Chemical class C1=CC=C2C(S(=O)(=O)OC(C)C)=CC=CC2=C1 ARENMZZMCSLORU-UHFFFAOYSA-N 0.000 description 2
- OHEFFKYYKJVVOX-UHFFFAOYSA-N sulcatol Natural products CC(O)CCC=C(C)C OHEFFKYYKJVVOX-UHFFFAOYSA-N 0.000 description 2
- LABTWGUMFABVFG-ONEGZZNKSA-N (3E)-pent-3-en-2-one Chemical compound C\C=C\C(C)=O LABTWGUMFABVFG-ONEGZZNKSA-N 0.000 description 1
- BGTFWRDJZNCBCV-AATRIKPKSA-N (e)-4-methylhex-3-en-2-one Chemical compound CC\C(C)=C\C(C)=O BGTFWRDJZNCBCV-AATRIKPKSA-N 0.000 description 1
- MLAPCZAEMSPIHB-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-methoxy-1-(2-methoxyethyl)-3-methylurea Chemical compound ClC1=CC=C(C=C1)N(C(=O)N(C)OC)CCOC MLAPCZAEMSPIHB-UHFFFAOYSA-N 0.000 description 1
- DMJWIYNOTAWVOH-UHFFFAOYSA-N 1-butoxy-1-butyl-3-(4-chloro-3-methylsulfanylphenyl)-3-ethylurea Chemical compound CCCCON(CCCC)C(=O)N(CC)C1=CC=C(Cl)C(SC)=C1 DMJWIYNOTAWVOH-UHFFFAOYSA-N 0.000 description 1
- DHESKPVRPQXGRM-UHFFFAOYSA-N 1-ethyl-1-methoxy-3-phenylurea Chemical compound CCN(OC)C(=O)NC1=CC=CC=C1 DHESKPVRPQXGRM-UHFFFAOYSA-N 0.000 description 1
- OWRHJTUZVUYYNA-UHFFFAOYSA-N 1-methoxy-3-methylurea Chemical compound CNC(=O)NOC OWRHJTUZVUYYNA-UHFFFAOYSA-N 0.000 description 1
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical class CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
- LIOVBQHDFPHDSP-UHFFFAOYSA-N 3-(3-chloro-4-ethoxyphenyl)-1-methoxy-1-methylurea Chemical compound CCOC1=CC=C(NC(=O)N(C)OC)C=C1Cl LIOVBQHDFPHDSP-UHFFFAOYSA-N 0.000 description 1
- HMOULFHNQQZLDV-UHFFFAOYSA-N 3-(4-bromophenyl)-1-methoxy-1-methylurea 3-(4-chlorophenyl)-1-methoxy-1-methylurea 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea Chemical compound ClC=1C=C(C=CC1Cl)NC(=O)N(OC)C.BrC1=CC=C(C=C1)NC(=O)N(OC)C.ClC1=CC=C(C=C1)NC(=O)N(OC)C HMOULFHNQQZLDV-UHFFFAOYSA-N 0.000 description 1
- UMOOQQMJNZVVKB-UHFFFAOYSA-N 3-(4-chloro-2-methylphenyl)-1-methoxy-1-methylurea Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1C UMOOQQMJNZVVKB-UHFFFAOYSA-N 0.000 description 1
- SIBULRZDICEHRZ-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-ethoxy-1-methylurea Chemical compound CCON(C)C(=O)NC1=CC=C(Cl)C=C1 SIBULRZDICEHRZ-UHFFFAOYSA-N 0.000 description 1
- BGTFWRDJZNCBCV-UHFFFAOYSA-N 4-methyl-3-hexen-2-one Natural products CCC(C)=CC(C)=O BGTFWRDJZNCBCV-UHFFFAOYSA-N 0.000 description 1
- GGBXJDKSEHTBLW-UHFFFAOYSA-N 5-methylhex-4-en-2-one Chemical compound CC(C)=CCC(C)=O GGBXJDKSEHTBLW-UHFFFAOYSA-N 0.000 description 1
- LIXZPXRZBOQNBU-UHFFFAOYSA-N C(C)(C)C1=CC=C(C=C1)N(C(=O)N(OC)CC)CC.ClC1=CC=C(C=C1)N(C(=O)N(OC)C)C Chemical compound C(C)(C)C1=CC=C(C=C1)N(C(=O)N(OC)CC)CC.ClC1=CC=C(C=C1)N(C(=O)N(OC)C)C LIXZPXRZBOQNBU-UHFFFAOYSA-N 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- BNQNEUPEQYLJGJ-UHFFFAOYSA-N FC(C1=CC(=C(N(C)C)C(=C1)[N+](=O)[O-])[N+](=O)[O-])(F)F.FC(C1=CC(=C(NCCC)C(=C1)[N+](=O)[O-])[N+](=O)[O-])(F)F Chemical compound FC(C1=CC(=C(N(C)C)C(=C1)[N+](=O)[O-])[N+](=O)[O-])(F)F.FC(C1=CC(=C(NCCC)C(=C1)[N+](=O)[O-])[N+](=O)[O-])(F)F BNQNEUPEQYLJGJ-UHFFFAOYSA-N 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- MBGVPDOCIANUJN-UHFFFAOYSA-N n,n-bis(2-methylpropyl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound CC(C)CN(CC(C)C)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O MBGVPDOCIANUJN-UHFFFAOYSA-N 0.000 description 1
- KNTOUMMLMPJOSR-UHFFFAOYSA-N n,n-di(butan-2-yl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound CCC(C)N(C(C)CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O KNTOUMMLMPJOSR-UHFFFAOYSA-N 0.000 description 1
- IFCKWWXWJYTNCS-UHFFFAOYSA-N n-ethyl-2,6-dinitro-n-propyl-4-(trifluoromethyl)aniline Chemical compound CCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O IFCKWWXWJYTNCS-UHFFFAOYSA-N 0.000 description 1
- UCGLSBJMKKXNCO-UHFFFAOYSA-N n-hexan-3-yl-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound CCCC(CC)NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O UCGLSBJMKKXNCO-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Die Erfindung betrifft flüssige Zubereitungen mit herbizider Wirkung, insbesondere flüssige Emulsionskonzentrate, die aus einer Mischung von herbiziden Wirkstoffen beste-35 hen, sowie ein Verfahren zu ihrer Herstellung. The invention relates to liquid preparations with a herbicidal action, in particular liquid emulsion concentrates which consist of a mixture of herbicidal active ingredients, and to a process for their preparation.
Es ist bekannt, dass bei der Bekämpfung von Unkräutern in landwirtschaftlichen Kulturen der Einsatz eines einzelnen Herbizid-Wirkstoffes oft eine ungenügende Kontrolle der grossen Anzahl von Unkräutern ergibt. Zur Erzielung ei-40 nes breiten Wirkungsspektrums werden deshalb gewöhnlich Mischungen, die aus 2 oder mehreren herbiziden Wirkstoffen bestehen, eingesetzt. Eine besonders wertvolle Mischung, die in der Praxis Eingang gefunden hat, besteht aus einer Kombination von herbizid wirkenden substituierten 2,6-Di-45 nitro-anilin-derivaten und N-Aryl-N'-alkoxy-harnstoff-deri-vaten. It is known that in the control of weeds in agricultural crops, the use of a single herbicidal active ingredient often results in insufficient control of the large number of weeds. Mixtures consisting of 2 or more herbicidal active compounds are therefore usually used to achieve a broad spectrum of activity. A particularly valuable mixture, which has found its way into practice, consists of a combination of herbicidally substituted 2,6-di-45 nitro-aniline derivatives and N-aryl-N'-alkoxy-urea derivatives.
Die physikalischen Eigenschaften dieser beiden Komponenten erschweren jedoch oft die Herstellung von benetzbaren Spritzpulvern oder fliessbaren Zubereitungen, so dass so die beiden Komponenten entweder getrennt angewandt werden müssen oder die Mischung unmittelbar vor Anwendung in einem Mischtank zu erfolgen hat, z.B. unter Verwendung der einen Komponente in Form eines Spritzpulvers und der andern Komponente in Form eines Emulsionskonzentrates. 55 In diesem Falle können jedoch Konzentrationsschwankungen, die durch die verschiedenen Absetzgeschwindigkeiten der Wirkstoff-Komponenten entstehen, erhebliche Schäden an den Kulturen verursachen. Überdies sind beide Anwendungsverfahren arbeitsintensiv und wenig wirtschaftlich. In 60 der Literatur sind auch Verfahren zur Herstellung von Emulsionskonzentraten beschrieben, die vor der Anwendung mit Wasser verdünnt werden und eine gleichmässige Dosierung der Wirkstoff-Komponenten erlauben. Alle diese Verfahren haben jedoch den Nachteil, dass relativ teure Lö-65 sungsmittel in hohen Anteilen eingesetzt werden müssen und diese Lösungsmittel überdies eine gewisse phytotoxische Wirkung aufweisen, die sich zufolge der relativ hohen Konzentration nachteilig auf die Nutzpflanzen auswirken kann. However, the physical properties of these two components often make it more difficult to produce wettable wettable powders or flowable preparations, so that the two components either have to be used separately or the mixture has to be mixed in a mixing tank immediately before use, e.g. using one component in the form of a wettable powder and the other component in the form of an emulsion concentrate. 55 In this case, however, fluctuations in the concentration caused by the different settling rates of the active ingredient components can cause considerable damage to the cultures. Furthermore, both application methods are labor intensive and not very economical. Methods for the preparation of emulsion concentrates are also described in the literature, which are diluted with water before use and which permit a uniform metering of the active ingredient components. However, all of these processes have the disadvantage that relatively expensive solvents have to be used in high proportions and, moreover, these solvents have a certain phytotoxic effect which, owing to the relatively high concentration, can have an adverse effect on the useful plants.
3 3rd
652 888 652 888
Die vorliegende Erfindung verfolgt das Ziel, die bisher verwendeten Lösungsmittel insbesondere die cyklischen Ke-tone wie Cyklohexanon und 3,5,5-Trimethyl-2-cyclohexen-l-on (Isophoron) durch wirksamere, phytotoxisch noch weniger bedenklich und insbesondere wirtschaftlich vorteilhaftere Lösungsmittel zu ersetzen. The present invention pursues the goal of using the solvents used up to now, in particular the cyclic ke-tones such as cyclohexanone and 3,5,5-trimethyl-2-cyclohexen-l-one (isophorone), by more effective, less phytotoxic and in particular economically more advantageous solvents to replace.
Es wurde gefunden, dass durch Verwendung von ungesättigten, aliphatischen Ketonen als Lösungsmittel dieses Ziel erreicht werden kann. Insbesondere 4-Methyl-3-penten-2-on (Mesityloxid) erfüllt die gestellten Anforderungen in idealer Weise. It has been found that this objective can be achieved by using unsaturated, aliphatic ketones as solvents. In particular, 4-methyl-3-penten-2-one (mesityl oxide) ideally meets the requirements.
Die hervorragenden Lösungseigenschaften der ungesättigten, aliphatischen Ketone erlauben deren Einsatz im Gemisch mit preisgünstigen herkömmlichen Lösungsmitteln, wie z.B. mit aromatischen Kohlenwasserstoffen, in wesentlich tieferen Anteilen als mit den für den gleichen Zweck in der Literatur beschriebenen Lösungsmitteln. Überdies ist beispielsweise Mesityloxid im Handel zu günstigeren Bedingungen erhältlich als die bisher verwendeten alicyklischen Ketone. The outstanding solution properties of the unsaturated, aliphatic ketones allow their use in a mixture with inexpensive conventional solvents, e.g. with aromatic hydrocarbons, in much lower proportions than with the solvents described for the same purpose in the literature. In addition, mesityl oxide, for example, is commercially available under more favorable conditions than the alicyclic ketones previously used.
Gegenstand der Erfindung sind stabile, flüssige Zubereitungen mit herbizider Wirkung bestehend aus einer Kombination eines herbizid wirkenden 2,6-Dinitroanilin- und eines herbizid wirkenden N-Aryl-N'-alkoxy-harnstoff-derivates, welche dadurch gekennzeichnet sind, dass sie als Lösungsmittel ein ungesättigtes, aliphatisches Keton enthalten. The invention relates to stable, liquid preparations with herbicidal activity consisting of a combination of a herbicidally active 2,6-dinitroaniline and a herbicidally active N-aryl-N'-alkoxy-urea derivative, which are characterized in that they are used as solvents contain an unsaturated, aliphatic ketone.
Als ungesättigtes, aliphatisches Keton kommt in erster Linie 4-Methyl-3-penten-2-on (Mesityloxid) in Betracht. Weitere brauchbare ungesättigte, aliphatische Ketone sind 3-Buten-2-on, 3-Penten-2-on, 5-Methyl-4-hexen-2-on, 4-Me-thyl-3-hexen-2-on, 6-Methyl-5-hepten-2-on, 5-Ethyl-4-hep-ten-3-on. The unsaturated, aliphatic ketone is primarily 4-methyl-3-penten-2-one (mesityl oxide). Further useful unsaturated, aliphatic ketones are 3-buten-2-one, 3-penten-2-one, 5-methyl-4-hexen-2-one, 4-methyl-3-hexen-2-one, 6 -Methyl-5-hepten-2-one, 5-ethyl-4-hepten-3-one.
Diese ungesättigten, aliphatischen Ketone können als einziges Lösungsmittel in den herbiziden Formulierungen verwendet werden. Dank ihrer hervorragenden Lösungseigenschaften ist es möglich, sie mit andern, bekannten Lösungsmitteln, insbesondere mit aromatischen Kohlenwasserstoffen, wie Alkylbenzolen, vor allem o-Xylol oder Xylol-Isomerengemischen, sowie Toluol und halogenierten Benzolen und halogenierten Alkylbenzolen und Mischungen davon zu verdünnen, ohne dass die herbiziden Wirkstoffe ausgeschieden werden. Je nach Wirkstoffkombination kann der Anteil der ungesättigten, aliphatischen Ketone bis auf 5% der Gesamtlösungsmittelkonzentration reduziert werden, d.h. das als Lösungsmittel dienende ungesättigte, aliphatische Keton kann mit aromatischen Kohlenwasserstoffen verdünnt werden bis zu einem Verhältnis von 5:95. These unsaturated, aliphatic ketones can be used as the only solvent in the herbicidal formulations. Thanks to their excellent dissolving properties, it is possible to dilute them with other known solvents, in particular with aromatic hydrocarbons, such as alkylbenzenes, especially o-xylene or xylene isomer mixtures, as well as toluene and halogenated benzenes and halogenated alkylbenzenes and mixtures thereof, without the herbicidal active substances are excreted. Depending on the combination of active ingredients, the proportion of unsaturated, aliphatic ketones can be reduced to 5% of the total solvent concentration, i.e. the unsaturated, aliphatic ketone serving as solvent can be diluted with aromatic hydrocarbons up to a ratio of 5:95.
Die erfindungsgemässen Zubereitungen enthalten als herbizid wirkende Anteile mindestens einen Vertreter bestehend aus einem 4-Trifluormethyl-2,6-dinitro-anilin der Formel (I) The preparations according to the invention contain, as herbicidally active constituents, at least one representative consisting of a 4-trifluoromethyl-2,6-dinitro-aniline of the formula (I)
0„N 0 "N
worin Rj und R2 Wasserstoff, einen Alkyl-rest mit 1 bis 6 C-Atomen oder einen Alkenyl-rest mit 2 bis 6 C-Atomen bedeutet, sowie einen N-Aryl-N'-alkoxy-harnstoff der Formel (II) wherein Rj and R2 are hydrogen, an alkyl radical with 1 to 6 C atoms or an alkenyl radical with 2 to 6 C atoms, and an N-aryl-N'-alkoxyurea of the formula (II)
R. R.
R, R,
'R3 'R3
N-CO-N N-CO-N
I I.
R5 R5
II, II,
OR, OR,
I, I,
worin R3 einen Alkyl-rest mit 1 bis 4 C-Atomen oder einen io Alkenyl-rest mit 1 bis 4 C-Atomen, R4 einen Alkyl-rest mit 1 bis 4 C-Atomen, R5 Wasserstoff, einen Alkyl-rest mit 1 bis 4 C-Atomen oder einen Alkoxyalkyl-rest mit 3 bis 4 C-Atomen und R6 und R7 Wasserstoffatome, Halogenatome oder Alkoxy-, Halogen-alkoxy-, Alkylthio- oder Alkyl-reste 15 mit 1 bis 4 C-Atomen oder Alkenyl-reste mit 2 bis 4 C-Atomen bedeuten. wherein R3 is an alkyl radical with 1 to 4 carbon atoms or an io alkenyl radical with 1 to 4 carbon atoms, R4 is an alkyl radical with 1 to 4 carbon atoms, R5 is hydrogen, an alkyl radical with 1 to 4 carbon atoms or an alkoxyalkyl radical with 3 to 4 carbon atoms and R6 and R7 hydrogen atoms, halogen atoms or alkoxy, halogenoalkoxy, alkylthio or alkyl radicals 15 with 1 to 4 carbon atoms or alkenyl radicals mean with 2 to 4 carbon atoms.
Diese beiden Wirkstoff-Komponenten lassen sich innerhalb weiter Grenzen kombinieren. Bevorzugt werden Mischungsverhältnisse von 1:10 bis 10:1, insbesondere von 4:1 20 bis 1:4. Die 4-Trifluormethyl-2,6-dinitro-aniline der Formel (I) sind bekannte herbizide Verbindungen. Beispiele für spezifische Verbindungen, die unter die Formel (I) fallen, sind folgende: These two active ingredient components can be combined within wide limits. Mixing ratios of 1:10 to 10: 1, in particular 4: 1 to 20: 1: 4, are preferred. The 4-trifluoromethyl-2,6-dinitro-anilines of the formula (I) are known herbicidal compounds. Examples of specific compounds that fall under formula (I) are as follows:
4-Trifluormethyl-2,6-dinitro-N,N-dipropyl-anilin 25 4-Trifluormethyl-2,6-dinitro-N,N-di-isobutyl-anilin 4-Trifluormethyl-2,6-dinitro-N-butyl-N-ethyl-anilin 4-Trifluormethyl-2,6-dinitro-N-ethyl-N-(2-methylethyl)-anilin 4-trifluoromethyl-2,6-dinitro-N, N-dipropyl-aniline 25 4-trifluoromethyl-2,6-dinitro-N, N-di-isobutyl-aniline 4-trifluoromethyl-2,6-dinitro-N-butyl -N-ethyl-aniline 4-trifluoromethyl-2,6-dinitro-N-ethyl-N- (2-methylethyl) aniline
4-Trifluormethyl-2,6-dinitro-N-ethyl-N-(2-methylallyl)-30 anilin 4-trifluoromethyl-2,6-dinitro-N-ethyl-N- (2-methylallyl) -30 aniline
4-Trifluormethyl-2,6-dinitro-N,N-di-sec.-butyl-anilin 4-Trifluormethyl-2,6-dinitro-N-methyl-N-n-butyl-anilin 4-Trifluormethyl-2,6-dinitro-N-methyl-N-n-amyl-anilin 4-Trifluormethyl-2,6-dinitro-N-ethyl-N-n-propyl-anilin 35 4-Trifluormethyl-2,6-dinitro-N-propyl-anilin 4-Trifluormethyl-2,6-dinitro-N,N-dimethyl-anilin 4-Trifluormethyl-2,6-dinitro-N-allyl-N-methyl-anilin 4-Trifluormethyl-2,6-dinitro-N,N-diallyl-anilin 4-trifluoromethyl-2,6-dinitro-N, N-di-sec.-butyl-aniline 4-trifluoromethyl-2,6-dinitro-N-methyl-Nn-butyl-aniline 4-trifluoromethyl-2,6-dinitro -N-methyl-Nn-amyl-aniline 4-trifluoromethyl-2,6-dinitro-N-ethyl-Nn-propyl-aniline 35 4-trifluoromethyl-2,6-dinitro-N-propyl-aniline 4-trifluoromethyl-2 , 6-dinitro-N, N-dimethyl-aniline 4-trifluoromethyl-2,6-dinitro-N-allyl-N-methyl-aniline 4-trifluoromethyl-2,6-dinitro-N, N-diallyl aniline
Beispiele für spezifische Harnstoff-Verbindungen, die un-40 ter die Formel (II) fallen, sind folgende: N-(3,4-Dichlorphenyl)-N'-methoxy-N'-methyl-harnstoff N-(4-Chlorphenyl)-N'-methoxy-N'-methyl-harnstoff N-(4-Bromphenyl)-N'-methoxy-N'-methyl-harnstoff N-(2-Methyl-4-chlorphenyl)-N'-methoxy-N'-methyl-harn- Examples of specific urea compounds which fall under the formula (II) are as follows: N- (3,4-dichlorophenyl) -N'-methoxy-N'-methyl-urea N- (4-chlorophenyl) -N'-methoxy-N'-methyl-urea N- (4-bromophenyl) -N'-methoxy-N'-methyl-urea N- (2-methyl-4-chlorophenyl) -N'-methoxy-N ' -methyl-urine-
45 stoff 45 fabric
N-(4-Chlorphenyl)-N'-methoxy-N'-ethyl-harnstoff N-Phenyl-N'-methoxy-N'-ethyl-harnstoff N-(3,4-Dichlorphenyl)-N'-methoxy-N'-isopropyl-harnstoff N-(4-Bromphenyl)-N'-methoxy-N'-n-butyl-harnstoff so N-(4-Methoxyphenyl)-N-methoxy-N'-allyl-harnstoff N-(4-Methylphenyl)-N'-isopropoxy-N'-methyl-harnstoff N-(3-Chlor-4-ethoxyphenyl)-N'-methoxy-N'-methyl-harn-stoff N- (4-chlorophenyl) -N'-methoxy-N'-ethyl-urea N-phenyl-N'-methoxy-N'-ethyl-urea N- (3,4-dichlorophenyl) -N'-methoxy-N '-isopropyl-urea N- (4-bromophenyl) -N'-methoxy-N'-n-butyl-urea so N- (4-methoxyphenyl) -N-methoxy-N'-allyl-urea N- (4- Methylphenyl) -N'-isopropoxy-N'-methyl-urea N- (3-chloro-4-ethoxyphenyl) -N'-methoxy-N'-methyl-urea
N-(3-Chlor-4-methylthiophenyl)-N'-methoxy-N'-methyl-55 harnstoff N-(4-Allylphenyl)-N'-methoxy-N'-methyl-harnstoff N-(4-Allyloxyphenyl)-N'-methoxy-N'-methyl-harnstoff N-(4-Chlorphenyl)-N,N'-dimethyl-N'-methoxy-harnstoff N-(4-Isopropylphenyl)-N,N'-diethyl-N'-methoxy-harnstoff 60 N-(4-Chlorphenyl)-N-methoxyethyl-N'-methoxy-N'-methyl-harnstoff N- (3-chloro-4-methylthiophenyl) -N'-methoxy-N'-methyl-55 urea N- (4-allylphenyl) -N'-methoxy-N'-methyl-urea N- (4-allyloxyphenyl) -N'-methoxy-N'-methyl-urea N- (4-chlorophenyl) -N, N'-dimethyl-N'-methoxy-urea N- (4-isopropylphenyl) -N, N'-diethyl-N ' -methoxy-urea 60 N- (4-chlorophenyl) -N-methoxyethyl-N'-methoxy-N'-methyl-urea
N-(3-Methylthio-4-chlorphenyl)-N-ethoxyethyl-N'-meth- N- (3-methylthio-4-chlorophenyl) -N-ethoxyethyl-N'-meth-
oxy-N'-allyl-harnstoff N-[3-Chlor-4-(difluorchlormethoxy)-phenyl]-N'-meth-65 oxy-N'-allyl-harnstoff oxy-N'-allyl urea N- [3-chloro-4- (difluorochloromethoxy) phenyl] -N'-meth-65 oxy-N'-allyl urea
Zur Herstellung von in Wasser gut emulgierbaren Zubereitungen werden ein oder mehrere anionische bzw. nichtionische Emulgatoren zugesetzt. One or more anionic or nonionic emulsifiers are added to prepare preparations which are readily emulsifiable in water.
652 888 652 888
4 4th
Beispielsweise können dazu folgende handelsübliche Tenside verwendet werden: For example, the following commercially available surfactants can be used:
Polyoxyethylen-sorbitan-fettsäureester wie Polyoxyethy-lensorbitanmonolaurate, -monopalmitate, -monostearate, -monooleate, -tristearate und -trioleate, z. B. Tween 20 "■ HLB-Wert 16 bis 17, Tween 60"' HLB-Wert 14-19, Tween 80- HLB-Wert 15, Alkylphenol-polyglykolether, wie Nonyl-und Isooctylphenylpolyethoxyethanole, Alkylarylsulfonate, wie Isopropylnaphthalinsulfonate, Dodecyl-benzolsulfonate usw. Polyoxyethylene sorbitan fatty acid esters such as polyoxyethylene lensorbitan monolaurates, monopalmitates, monostearates, monooleates, tristearates and trioleates, e.g. B. Tween 20 "■ HLB value 16 to 17, Tween 60" HLB value 14-19, Tween 80-HLB value 15, alkylphenol polyglycol ethers such as nonyl and isooctylphenyl polyethoxyethanols, alkylarylsulfonates such as isopropylnaphthalenesulfonates, dodecylbenzenesulfonates etc.
Die Herstellung der Zubereitungen erfolgt, indem man die ausgewählten herbiziden Wirkstoffkomponenten im gewünschten ungesättigten, aliphatischen Keton, vorzugsweise in Mesityloxid, löst, wobei aufgrund der hervorragenden Lösungseigenschaften eine Verdünnung mit herkömmlichen Lösungsmitteln, insbesondere mit aromatischen Kohlenwasserstoffen, vorzugsweise o-Xylol oder Xylol-Isomerengemi-sche im Verhältnis von 5 bis 95 Gew.% vorgenommen werden kann. Dem Gemisch werden anionische und/oder nichtionische Emulgatoren in Konzentrationen von 0,5 bis 20% zugegeben. The preparations are prepared by dissolving the selected herbicidal active ingredient components in the desired unsaturated, aliphatic ketone, preferably in mesityl oxide, where due to the outstanding solution properties, dilution with conventional solvents, in particular with aromatic hydrocarbons, preferably o-xylene or xylene isomer mixtures, cal in the ratio of 5 to 95 wt.% Can be made. Anionic and / or nonionic emulsifiers are added to the mixture in concentrations of 0.5 to 20%.
Zur Anwendung wird das Emulsionskonzentrat mit Wasser versetzt, wobei eine wässerige Emulsion, in welchen die Wirkstoffe homogen verteilt sind, entsteht. Die Verdünnung mit Wasser erfolgt im allgemeinen im Verhältnis 1:100 bis 1:800. Diese wässerige Emulsion weist einen herbiziden Effekt mit breitem Wirkungsspektrum auf. Im allgemeinen beträgt die Aufwandmenge 1 bis 10 kg/ha, vorzugsweise 3 bis 5 kg/ha. For use, the emulsion concentrate is mixed with water, resulting in an aqueous emulsion in which the active ingredients are homogeneously distributed. The dilution with water is generally in the ratio 1: 100 to 1: 800. This aqueous emulsion has a herbicidal effect with a broad spectrum of activity. In general, the application rate is 1 to 10 kg / ha, preferably 3 to 5 kg / ha.
Die herbizid wirkenden Zubereitungen werden auf die Erdbodenoberfläche vor oder nach dem Aufgehen der Unkräuter versprüht. Die Anwendung erfolgt vor oder nach dem Aufgehen der Kulturpflanzen, ohne bei diesen eine Schädigung zu bewirken. Diese herbizid wirkenden Zubereitungen werden mit Vorteil bei folgenden Nutzpflanzen eingesetzt: Getreide, Kartoffeln, Tomaten, Karotten, Erbsen, Luzerne, Bohnen, Pfeffer u.a.m. The herbicidal preparations are sprayed onto the surface of the soil before or after the weeds have risen. The application takes place before or after the crops have risen without causing any damage to them. These herbicidal preparations are used with advantage in the following crops: cereals, potatoes, tomatoes, carrots, peas, alfalfa, beans, pepper, etc.
Die folgenden Beispiele sollen die Erfindung erläutern ohne sie zu begrenzen. The following examples are intended to illustrate the invention without limiting it.
Beispiel 1 example 1
24,5 Gewichtsteile 4-Trifluormethyl-2,6-dinitro-N-ethyl-N-butyl-anilin und 12,25 Gewichtsteile N-(3,4-Dichlor-phenyl)-N'-methoxy-N'-methyI-harnstoff werden in 40 Gewichtsteilen o-Xylol aufgeschlämmt, mit 6 Gewichtsteilen Polyoxyethylen-sorbitan-fettsäureester (Tween 20®) und 3 Gewichtsteilen Alkylphenolpolyglykolether (Tinovetin NR-Supra " ) versetzt, darauf mit 7 Gewichtsteilen 4-Methyl-3-penten-2-on (Mesityloxid) vermischt und mit weiterem o-Xylol auf 100 Gewichtsteile ergänzt. Das Gemisch wird auf 50 bis 60 C erwärmt, bis eine Lösung entsteht. Nach Abkühlung auf Raumtemperatur wird die Lösung zur Entfernung von unlöslichen Verunreinigungen filtriert. 24.5 parts by weight of 4-trifluoromethyl-2,6-dinitro-N-ethyl-N-butyl-aniline and 12.25 parts by weight of N- (3,4-dichlorophenyl) -N'-methoxy-N'-methyl- urea is suspended in 40 parts by weight of o-xylene, 6 parts by weight of polyoxyethylene sorbitan fatty acid ester (Tween 20®) and 3 parts by weight of alkylphenol polyglycol ether (Tinovetin NR-Supra ") are added, followed by 7 parts by weight of 4-methyl-3-penten-2- on (mesityl oxide) and supplemented with additional o-xylene to 100 parts by weight, the mixture is heated to 50 to 60 ° C. until a solution is obtained, and after cooling to room temperature the solution is filtered to remove insoluble impurities.
Beispiel 2 Example 2
15 Gewichtsteile 4-Trifluormethyl-2,6-dinitro-N-ethyl-N-(2-methylallyl)-anilin und 10 Gewichtsteile N-(3,4-Dichlor-phenyO-N'-methoxy-N'-methyl-harnstoff werden zunächst in 40 Gewichtsteilen eines Xylol-Isomerengemisches (Siedebereich 160 bis 175 'C) aufgeschlämmt, mit 5 Gewichtsteilen Polyoxyethylen-sorbitan-monostearat und 8 Gewichtsteilen Nonylphenylpolyglykolether versetzt, darauf mit 10 Gewichtsteilen 4-Methyl-3-penten-2-on vermischt und mit weiterem Xylol-Isomerengemisch auf 100 Gewichtsteile ergänzt. Auch hier wird zur Lösung der Komponenten auf 50 bis 60 C erwärmt, abgekühlt und filtriert. 15 parts by weight of 4-trifluoromethyl-2,6-dinitro-N-ethyl-N- (2-methylallyl) aniline and 10 parts by weight of N- (3,4-dichlorophenyO-N'-methoxy-N'-methyl-urea are first slurried in 40 parts by weight of a xylene isomer mixture (boiling range 160 to 175 ° C.), mixed with 5 parts by weight of polyoxyethylene sorbitan monostearate and 8 parts by weight of nonylphenyl polyglycol ether, then mixed with 10 parts by weight of 4-methyl-3-penten-2-one and supplemented with a further xylene isomer mixture to 100 parts by weight, in which case the components are heated to 50 to 60 ° C., cooled and filtered.
Beispiel 3 Example 3
24 Gewichtsteile 4-Trifluormethyl-2,6-dinitro-N,N-dipropyl-anilin und 12 Gewichtsteile N-(3,4-Dichlorphenyl)-N'-methoxy-N'-methyl-harnstoff werden in 40 Gewichtsteilen o-Xylol aufgeschlämmt, mit 8 Gewichtsteilen Polyoxy-ethylensorbitanmonostearat und 3 Gewichtsteilen Nonylphenylpolyglykolether versetzt, mit 12 Gewichtsteilen 4-Me-thyl-3-penten-2-on vermischt und mit weiterem o-Xylol auf 100 Gewichtsteile ergänzt. Das Gemisch wird auf 50 bis 60 "C erwärmt, wobei die Komponenten in Lösung gehen. Nach Abkühlung auf Raumtemperatur wird filtriert. Es resultiert dabei ein Emulsionskonzentrat, das vor Anwendung lediglich mit Wasser verdünnt werden muss. 24 parts by weight of 4-trifluoromethyl-2,6-dinitro-N, N-dipropyl-aniline and 12 parts by weight of N- (3,4-dichlorophenyl) -N'-methoxy-N'-methyl-urea are in 40 parts by weight of o-xylene slurried, mixed with 8 parts by weight of polyoxyethylene sorbitan monostearate and 3 parts by weight of nonylphenyl polyglycol ether, mixed with 12 parts by weight of 4-methyl-3-penten-2-one and made up to 100 parts by weight with additional o-xylene. The mixture is heated to 50 to 60 ° C., the components dissolving. After cooling to room temperature, the mixture is filtered. The result is an emulsion concentrate which only has to be diluted with water before use.
Beispiele 4 bis 30 In ähnlicher Weise, wie in den Beispielen 1 bis 3 beschrieben, werden auch die in der Tabelle aufgeführten Zubereitungen hergestellt. Examples 4 to 30 In a similar manner to that described in Examples 1 to 3, the preparations listed in the table are also prepared.
Tabelle table
Bei- Herbizid Emulgatoren Lösungs- Verdünnungs- Herbicide Emulsifiers Solution Diluent
spiel Nr. game number
I I.
% %
II II
% %
an at
% %
nn % nn%
mittel K. % medium K.%
mittel ad 100% medium ad 100%
4 4th
A A
24 24th
A A
12 12
A A
5 5
A A
8 8th
B B
10 10th
B B
5 5
B B
29 29
B B
7 7
B B
4 4th
B B
10 10th
B B
10 10th
F F
6 6
C C.
36 36
C C.
18 18th
— -
C C.
8 8th
B B
12 12
A A
7 7
D D
9 9
D D
25 25th
B B
3 3rd
D D
8 8th
B B
15 15
A A
8 8th
E E
8 8th
E E
26 26
B B
3 3rd
A A
8 8th
B B
20 20th
— -
9 9
F F
7 7
F F
29 29
A A
3 3rd
B B
7 7
A A
15 15
B B
10 10th
G G
32 32
G 25 G 25
A A
4 4th
C C.
8 8th
B B
26 26
B B
11 11
H H
25 25th
H 25 H 25
B B
4 4th
D D
9 9
B B
27 27th
B B
12 12
I I.
15 15
A A
20 20th
A A
7 7
A A
10 10th
A A
13 13
K K
20 20th
B B
16 16
A A
4 4th
B B
6 6
B B
20 20th
A A
14 14
A A
25 25th
C C.
11 11
A A
4 4th
C C.
5 5
C C.
10 10th
B B
15 15
B B
24 24th
D D
12 12
B B
4 4th
D D
5 5
A A
10 10th
A + B (1:1) A + B (1: 1)
16 16
C C.
20 20th
E E
15 15
B B
4 4th
A A
5 5
B B
15 15
A + B (1:3) A + B (1: 3)
17 17th
D D
15 15
F F
10 10th
A A
3 3rd
B B
6 6
B B
10 10th
A + B(2:l) A + B (2: 1)
18 18th
E E
12 12
G G
18 18th
A A
3 3rd
C C.
6 6
B B
17 17th
A + B (1:4) A + B (1: 4)
19 19th
F F
36 36
H H
18 18th
B B
2 2nd
D D
8 8th
B B
25 25th
A A
20 20th
G G
18 18th
A A
18 18th
B B
3 3rd
A A
6 6
C C.
12 12
A A
21 21st
H H
18 18th
B B
18 18th
- -
B B
8 8th
D D
12 12
B B
22 22
I I.
24 24th
E E
12 12
A A
4 4th
C C.
5 5
B B
15 15
B B
23 23
K K
25 25th
D D
15 15
B B
3 3rd
D D
6 6
B B
30 30th
— -
24 24th
A A
25 25th
E E
15 15
B B
3 3rd
A A
5 5
B B
28 28
— -
25 25th
B B
24 24th
F F
12 12
A A
3 3rd
B B
4 4th
B B
20 20th
D D
26 26
C C.
22 22
G G
14 14
A A
4 4th
C C.
4 4th
B B
15 15
E + A (1:2) I + O (1: 2)
27 27th
D D
20 20th
H H
15 15
B B
5 5
D D
4 4th
B B
15 15
F F
28 28
E E
24 24th
A A
12 12
B B
3 3rd
A A
5 5
B B
20 20th
F F
29 29
F F
30 30th
B B
8 8th
A A
3 3rd
B B
6 6
B B
15 15
C C.
30 30th
G G
26 26
C C.
10 10th
- -
C C.
8 8th
B B
18 18th
A + B (1:1) A + B (1: 1)
Erläuterungen zur Tabelle % = Gew.% Explanations to the table% =% by weight
Herbizid I = 4-Trifluormethyl-2,6-dinitro-anilm-derivate der allgemeinen Formel I Herbicide I = 4-trifluoromethyl-2,6-dinitro-anilm derivatives of the general formula I.
A: 4-Trifluormethyl-2,6-dinitro-N-ethyl-N-(2-methylethyl)-anilin B: 4-Trifluormethyl-2,6-dinitro-N,N-di-isobutyl-anilin C: 4-Trifluormethyl-2,6-dinitro-N,N-di-sec.-butyl-anilin D: 4-Trifluormethyl-2,6-dinitro-N-methyl-N-n-butyl-anilin E: 4-Trifluormethyl-2,6-dinitro-N-methyl-N-n-amyl-anilin F: 4-Trifluormethyl-2,6-dinitro-N-ethyl-N-n-butyl-anilin G: 4-Trifluormethyl-2,6-dinitro-N-ethyl-N-n-propyl-anilin A: 4-trifluoromethyl-2,6-dinitro-N-ethyl-N- (2-methylethyl) aniline B: 4-trifluoromethyl-2,6-dinitro-N, N-di-isobutyl-aniline C: 4- Trifluoromethyl-2,6-dinitro-N, N-di-sec-butyl-aniline D: 4-trifluoromethyl-2,6-dinitro-N-methyl-Nn-butyl-aniline E: 4-trifluoromethyl-2,6 -dinitro-N-methyl-Nn-amyl-aniline F: 4-trifluoromethyl-2,6-dinitro-N-ethyl-Nn-butyl-aniline G: 4-trifluoromethyl-2,6-dinitro-N-ethyl-Nn propyl aniline
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
H: 4-Trifluorrnethyl-2,6-dinitro-N.N-dimethyl-anilin I: 4-Trifluormethyl-2,6-dinitro-N-sec.-butyl-anilin K: 4-Trifluormethyl-2,6-dinitro-N-(3-hexyl)-anilin H: 4-trifluoromethyl-2,6-dinitro-NN-dimethyl-aniline I: 4-trifluoromethyl-2,6-dinitro-N-sec.-butyl-aniline K: 4-trifluoromethyl-2,6-dinitro-N - (3-hexyl) aniline
Herbizid II = N-Aryl-N'-alkoxy-N'-alkyl-harnstoff-derivat der allgemeinen Formel II Herbicide II = N-aryl-N'-alkoxy-N'-alkylurea derivative of the general formula II
A: N-(4-Chlorphenyl)-N'-ethoxy-N'-methyl-harnstoff B : N-(2-Methyl-4-chIorphenyl)-N'-methoxy-N'-methyl-harnstoff C : N-Phenyl-N'-methoxy-N'-ethyl-harnstoff D: N-(4-Methoxyphenyl)-N'-methoxy-N'-alkyl-harnstoff E: N-(3-Chlor-4-ethoxyphenyl)-N'-methoxy-N'-methyl-harnstoff F: N-(4-Difluorchlormethoxyphenyl)-N-methoxymethyl-N'- A: N- (4-chlorophenyl) -N'-ethoxy-N'-methyl-urea B: N- (2-methyl-4-chlorophenyl) -N'-methoxy-N'-methyl-urea C: N- Phenyl-N'-methoxy-N'-ethylurea D: N- (4-methoxyphenyl) -N'-methoxy-N'-alkylurea E: N- (3-chloro-4-ethoxyphenyl) -N ' -methoxy-N'-methyl-urea F: N- (4-difluorochloromethoxyphenyl) -N-methoxymethyl-N'-
methoxy-N'-methyl-harnstoff G: N-(3-Alkyl-4-chlorphenyl)-N'-methoxy-N'-allyl-harnstoff H: N-(3-Methylthio-4-chlorphenyl)-N-ethyl-N'-butoxy-N'-butyl-harnstoff methoxy-N'-methyl-urea G: N- (3-alkyl-4-chlorophenyl) -N'-methoxy-N'-allyl-urea H: N- (3-methylthio-4-chlorophenyl) -N-ethyl -N'-butoxy-N'-butylurea
Emulgatoren an = anionische Tenside A: Isopropylnaphtalinsulfonate B: Dodecylbenzolsulfonate Emulsifiers on = anionic surfactants A: isopropylnaphthalene sulfonate B: dodecylbenzenesulfonate
Emulgatoren nn = nicht-ionische Tenside A: Polyoxyethylensorbitanmonolaurate B: Polyoxyethylen-sorbitanmonopalmitate C: Polyoxyethylen-sorbitanmonostearate D: Isooctyl-phenylpolyethoxyethanole 5 E: Ethoxyliertes Octylcresol Emulsifiers nn = non-ionic surfactants A: polyoxyethylene sorbitan monolaurate B: polyoxyethylene sorbitan monopalmitate C: polyoxyethylene sorbitan monostearate D: isooctylphenylpolyethoxyethanols 5 E: ethoxylated octylcresol
Lösungsmittel ungesättigtes aliphatisches Keton A: 3-Buten-2-on Solvent-unsaturated aliphatic ketone A: 3-buten-2-one
B: 4-Methyl-3-penten-2-on (.Mesityloxid) io C: 6-Methyl-5-hepten-2-on D: 5-Ethyl-4-hepten-3-on B: 4-methyl-3-penten-2-one (.Mesityloxide) io C: 6-methyl-5-hepten-2-one D: 5-ethyl-4-hepten-3-one
Verdünnungsmittel A: o-Xylol Diluent A: o-xylene
B: Xylol-Isomerengemisch 15 C: Toluol D: Chlorbenzol E: 4-Chlor-toluol B: mixture of xylene isomers 15 C: toluene D: chlorobenzene E: 4-chlorotoluene
F: technische Alkylbenzolgemische (Solvesso1", Shellsol "). F: technical alkylbenzene mixtures (Solvesso1 ", Shellsol").
25 25th
30" 30 "
35 35
40 40
45 45
50 50
55 55
65 65
Claims (14)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5044/82A CH652888A5 (en) | 1982-08-25 | 1982-08-25 | STABLE, LIQUID PREPARATION WITH HERBICIDAL EFFECT AND METHOD FOR THE PRODUCTION THEREOF. |
| GB08320961A GB2126088B (en) | 1982-08-25 | 1983-08-03 | Herbcidal liquid preparation and method for its production |
| IT22479/83A IT1164402B (en) | 1982-08-25 | 1983-08-08 | STABLE LIQUID PREPARATION WITH HERBICIDE ACTION AND PROCESS FOR ITS PREPARATION |
| FR8313597A FR2532151A1 (en) | 1982-08-25 | 1983-08-23 | STABLE LIQUID COMPOSITION HAVING HERBICIDE ACTIVITY AND PROCESS FOR PREPARING THE SAME |
| BE0/211395A BE897581A (en) | 1982-08-25 | 1983-08-23 | STABLE LIQUID COMPOSITION WITH HERBICIDAL ACTIVITY AND PROCESS FOR PREPARING SAME |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5044/82A CH652888A5 (en) | 1982-08-25 | 1982-08-25 | STABLE, LIQUID PREPARATION WITH HERBICIDAL EFFECT AND METHOD FOR THE PRODUCTION THEREOF. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH652888A5 true CH652888A5 (en) | 1985-12-13 |
Family
ID=4287005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5044/82A CH652888A5 (en) | 1982-08-25 | 1982-08-25 | STABLE, LIQUID PREPARATION WITH HERBICIDAL EFFECT AND METHOD FOR THE PRODUCTION THEREOF. |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE897581A (en) |
| CH (1) | CH652888A5 (en) |
| FR (1) | FR2532151A1 (en) |
| GB (1) | GB2126088B (en) |
| IT (1) | IT1164402B (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL196870A (en) * | 1955-04-29 | |||
| US3373010A (en) * | 1964-10-08 | 1968-03-12 | Du Pont | Herbicidal composition and method |
| GB1473105A (en) * | 1973-08-10 | 1977-05-11 | ||
| IT1131750B (en) * | 1980-06-06 | 1986-06-25 | Montedison Spa | STABLE FORMULATIONS OF N- (3,4-DICHLOROFENYL) -N'METOXY-N'-METHYLENE (LINORUN) AND 2,6-DINITOR-N, N-DIPROPYL-4-TRIFLUOR METHYLANILINE (TRIFLURALIN) IN EMULSION |
-
1982
- 1982-08-25 CH CH5044/82A patent/CH652888A5/en not_active IP Right Cessation
-
1983
- 1983-08-03 GB GB08320961A patent/GB2126088B/en not_active Expired
- 1983-08-08 IT IT22479/83A patent/IT1164402B/en active
- 1983-08-23 FR FR8313597A patent/FR2532151A1/en active Pending
- 1983-08-23 BE BE0/211395A patent/BE897581A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT8322479A0 (en) | 1983-08-08 |
| GB2126088A (en) | 1984-03-21 |
| IT1164402B (en) | 1987-04-08 |
| GB8320961D0 (en) | 1983-09-07 |
| GB2126088B (en) | 1986-01-02 |
| FR2532151A1 (en) | 1984-03-02 |
| BE897581A (en) | 1983-12-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0077759B1 (en) | Phenyl urea | |
| DE68907650T2 (en) | Surfactant based on oxyethylated and oxypropylated phenyl-1-ethylphenols, process for their preparation and their use for obtaining concentrated solutions of active compounds. | |
| EP0175649B1 (en) | Substituted carbodiimides | |
| EP0235089B1 (en) | N-benzoyl-n'-phenyl ureas, their preparation and their use against pests | |
| DE2213057A1 (en) | Herbicidal and pesticidal arylaminopyridine compounds, their production and their use | |
| EP0179021A2 (en) | Benzoylphenyl ureas | |
| DE2928410A1 (en) | ACYL UREAS, INSECTICIDAL AGENTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF | |
| EP0055213B1 (en) | Phenyl ureas | |
| EP0495748A1 (en) | Acaricidal agents | |
| EP0044278B1 (en) | Phenyl ureas | |
| CH652888A5 (en) | STABLE, LIQUID PREPARATION WITH HERBICIDAL EFFECT AND METHOD FOR THE PRODUCTION THEREOF. | |
| EP0174274B1 (en) | Phenylbenzoylurea derivatives | |
| EP0014674B1 (en) | Substituted n-phenyl-n'-benzoyl ureas, processes for their preparation, agents containing these compounds and their use in combating pests; substituted 4-(propenyloxy)-anilines | |
| DE3110473C2 (en) | N-alkyl-2'-n-butoxy-6'-ethyl-2-chloroacetanilides and herbicides containing these compounds | |
| DE2061133A1 (en) | Pesticidal compound, process for its preparation and use | |
| EP0065487B1 (en) | Phenyl urea derivative | |
| DE1542972B2 (en) | HERBICIDE MEDIUM | |
| EP0173244B1 (en) | Benzoylphenyl ureas | |
| DE2048660A1 (en) | N o Fluorophenylureas for pollution control | |
| DE3045770C2 (en) | ||
| DE3235419A1 (en) | Phenylureas | |
| DE1809838C3 (en) | N- (3-Bromo-4-chlorophenyl) -N'methoxy-N'-methylurea and its use as a herbicide | |
| AT211603B (en) | Selective herbicidal mixtures | |
| DE2129199C3 (en) | Preparations for selective weed control in beets | |
| EP0165903A2 (en) | Phenyl benzoyl ureas |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |