IE47006B1 - N-alkoxy-dinitro anilines and their herbicidal compositions - Google Patents

N-alkoxy-dinitro anilines and their herbicidal compositions

Info

Publication number: IE47006B1
Authority: IE; Ireland
Prior art keywords: dinitro; ethyl; toluidine; methoxy; formula
Prior art date: 1977-06-27

Application number

IE1255/78A

Other languages

English (en)

Other versions

IE781255L (en

Original Assignee

Lilly Co Eli

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-06-27

Filing date

1978-06-23

Publication date

1983-11-30

1977-06-27 Priority claimed from US05/810,229 external-priority patent/US4087460A/en

1977-06-27 Priority claimed from US05/810,228 external-priority patent/US4143073A/en

1978-06-23 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1978-12-27 Publication of IE781255L publication Critical patent/IE781255L/xx

1983-11-30 Publication of IE47006B1 publication Critical patent/IE47006B1/en

Links

239000000203 mixture Substances 0.000 title claims description 64
230000002363 herbicidal effect Effects 0.000 title claims description 21
238000000034 method Methods 0.000 claims abstract description 29
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
-1 4-substituted anilines Chemical class 0.000 claims abstract description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 39
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 35
239000012312 sodium hydride Substances 0.000 claims description 35
229910000104 sodium hydride Inorganic materials 0.000 claims description 35
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 claims description 21
239000002904 solvent Substances 0.000 claims description 21
239000002689 soil Substances 0.000 claims description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
QNJWNBPXXLOBKN-UHFFFAOYSA-N 4-ethyl-n-methoxy-2,6-dinitroaniline Chemical compound CCC1=CC([N+]([O-])=O)=C(NOC)C([N+]([O-])=O)=C1 QNJWNBPXXLOBKN-UHFFFAOYSA-N 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
229940100198 alkylating agent Drugs 0.000 claims description 5
239000002168 alkylating agent Substances 0.000 claims description 5
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 claims description 5
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
SWBZUJIDXGFAFV-UHFFFAOYSA-N 4-ethyl-n-methoxy-n-methyl-2,6-dinitroaniline Chemical compound CCC1=CC([N+]([O-])=O)=C(N(C)OC)C([N+]([O-])=O)=C1 SWBZUJIDXGFAFV-UHFFFAOYSA-N 0.000 claims description 3
KQINZPRXHYZZCM-UHFFFAOYSA-N n-methoxy-4-methyl-2,6-dinitroaniline Chemical compound CONC1=C([N+]([O-])=O)C=C(C)C=C1[N+]([O-])=O KQINZPRXHYZZCM-UHFFFAOYSA-N 0.000 claims description 3
SISGGDRMIMFNOL-UHFFFAOYSA-N 4-ethyl-n-methoxy-2,6-dinitro-n-propylaniline Chemical compound CCCN(OC)C1=C([N+]([O-])=O)C=C(CC)C=C1[N+]([O-])=O SISGGDRMIMFNOL-UHFFFAOYSA-N 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
150000001555 benzenes Chemical class 0.000 claims description 2
WZLORQYYVJMKFB-UHFFFAOYSA-N n,4-diethyl-n-methoxy-2,6-dinitroaniline Chemical compound CCN(OC)C1=C([N+]([O-])=O)C=C(CC)C=C1[N+]([O-])=O WZLORQYYVJMKFB-UHFFFAOYSA-N 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
RZKBRXDCJZLQLI-UHFFFAOYSA-N 2,5-dinitroaniline Chemical class NC1=CC([N+]([O-])=O)=CC=C1[N+]([O-])=O RZKBRXDCJZLQLI-UHFFFAOYSA-N 0.000 claims 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Chemical group 0.000 claims 1
FLGWZWFQBLCLMB-UHFFFAOYSA-N n-methoxy-4-methyl-2,6-dinitro-n-propylaniline Chemical compound CCCN(OC)C1=C([N+]([O-])=O)C=C(C)C=C1[N+]([O-])=O FLGWZWFQBLCLMB-UHFFFAOYSA-N 0.000 claims 1
150000004992 toluidines Chemical class 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 45
239000004009 herbicide Substances 0.000 abstract description 8
238000002360 preparation method Methods 0.000 abstract description 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
239000000047 product Substances 0.000 description 27
238000012360 testing method Methods 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 23
238000004458 analytical method Methods 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
238000002844 melting Methods 0.000 description 18
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239000006185 dispersion Substances 0.000 description 17
238000000921 elemental analysis Methods 0.000 description 16
239000002480 mineral oil Substances 0.000 description 16
235000010446 mineral oil Nutrition 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
241000196324 Embryophyta Species 0.000 description 15
239000007795 chemical reaction product Substances 0.000 description 14
238000005303 weighing Methods 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000003208 petroleum Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
239000002274 desiccant Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
150000001448 anilines Chemical class 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 8
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 7
241000894007 species Species 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
238000011282 treatment Methods 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 5
240000008042 Zea mays Species 0.000 description 5
NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 5
230000008654 plant damage Effects 0.000 description 5
239000007921 spray Substances 0.000 description 5
240000006995 Abutilon theophrasti Species 0.000 description 4
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240000006122 Chenopodium album Species 0.000 description 4
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244000152970 Digitaria sanguinalis Species 0.000 description 4
235000010823 Digitaria sanguinalis Nutrition 0.000 description 4
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
208000027418 Wounds and injury Diseases 0.000 description 4
240000003307 Zinnia violacea Species 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
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238000005406 washing Methods 0.000 description 4
240000001549 Ipomoea eriocarpa Species 0.000 description 3
235000005146 Ipomoea eriocarpa Nutrition 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
125000005262 alkoxyamine group Chemical group 0.000 description 3
235000008504 concentrate Nutrition 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
238000007865 diluting Methods 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
HFHAVERNVFNSHL-UHFFFAOYSA-N 2-chloro-1,3-dinitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1Cl HFHAVERNVFNSHL-UHFFFAOYSA-N 0.000 description 2
JMDVARRGYWIJGZ-UHFFFAOYSA-N 2-chloro-5-methyl-1,3-dinitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 JMDVARRGYWIJGZ-UHFFFAOYSA-N 0.000 description 2
OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
244000237956 Amaranthus retroflexus Species 0.000 description 2
235000004135 Amaranthus viridis Nutrition 0.000 description 2
241000209764 Avena fatua Species 0.000 description 2
235000007320 Avena fatua Nutrition 0.000 description 2
235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
235000009332 Chenopodium rubrum Nutrition 0.000 description 2
240000008067 Cucumis sativus Species 0.000 description 2
240000008853 Datura stramonium Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
244000299507 Gossypium hirsutum Species 0.000 description 2
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235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
240000004658 Medicago sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007226 Setaria italica Nutrition 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
235000007244 Zea mays Nutrition 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000004927 clay Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
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INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
KNVSVLOUJAKHGC-UHFFFAOYSA-N n-ethoxy-4-methyl-2,6-dinitroaniline Chemical compound CCONC1=C([N+]([O-])=O)C=C(C)C=C1[N+]([O-])=O KNVSVLOUJAKHGC-UHFFFAOYSA-N 0.000 description 2
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UZYRSBACWZIFIX-UHFFFAOYSA-N 1-(2,6-dinitrophenyl)piperidine Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1N1CCCCC1 UZYRSBACWZIFIX-UHFFFAOYSA-N 0.000 description 1
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CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 1
PUVGBKOHDJUFRZ-UHFFFAOYSA-N 2-(2-pyridin-3-ylpiperidin-1-yl)acetonitrile Chemical compound N#CCN1CCCCC1C1=CC=CN=C1 PUVGBKOHDJUFRZ-UHFFFAOYSA-N 0.000 description 1
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000009526 moderate injury Effects 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
DWTLUOIUPZTFIG-UHFFFAOYSA-N n,n,4-trimethyl-2,6-dinitroaniline Chemical compound CN(C)C1=C([N+]([O-])=O)C=C(C)C=C1[N+]([O-])=O DWTLUOIUPZTFIG-UHFFFAOYSA-N 0.000 description 1
HGNBXYKIEXEDTB-UHFFFAOYSA-N n-ethyl-n-methoxy-4-methyl-2,6-dinitroaniline Chemical compound CCN(OC)C1=C([N+]([O-])=O)C=C(C)C=C1[N+]([O-])=O HGNBXYKIEXEDTB-UHFFFAOYSA-N 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000003415 peat Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
WQMOWDRIXRBJBW-UHFFFAOYSA-N phenyl(piperidin-1-yl)diazene Chemical compound C1CCCCN1N=NC1=CC=CC=C1 WQMOWDRIXRBJBW-UHFFFAOYSA-N 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
235000014483 powder concentrate Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
IVNFTPCOZIGNAE-UHFFFAOYSA-N propan-2-yl hydrogen sulfate Chemical compound CC(C)OS(O)(=O)=O IVNFTPCOZIGNAE-UHFFFAOYSA-N 0.000 description 1
TYRGSDXYMNTMML-UHFFFAOYSA-N propyl hydrogen sulfate Chemical compound CCCOS(O)(=O)=O TYRGSDXYMNTMML-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000004576 sand Substances 0.000 description 1
208000037974 severe injury Diseases 0.000 description 1
230000009528 severe injury Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000012085 test solution Substances 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds only one oxygen atom attached to the nitrogen atom

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

IE1255/78A 1977-06-27 1978-06-23 N-alkoxy-dinitro anilines and their herbicidal compositions IE47006B1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/810,229 US4087460A (en)	1977-06-27	1977-06-27	Substituted N-alkoxy-N-substituted-2,6-dinitroanilines and intermediates for the preparation thereof
US05/810,228 US4143073A (en)	1977-06-27	1977-06-27	Process for preparing substituted n-alkoxy-n-substituted-2,6-dinitroanilines

Publications (2)

Publication Number	Publication Date
IE781255L IE781255L (en)	1978-12-27
IE47006B1 true IE47006B1 (en)	1983-11-30

Family

ID=27123324

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE1255/78A IE47006B1 (en)	1977-06-27	1978-06-23	N-alkoxy-dinitro anilines and their herbicidal compositions

Country Status (12)

Country	Link
JP (1)	JPS5412330A (it)
AR (1)	AR219755A1 (it)
BR (1)	BR7804052A (it)
CH (1)	CH636840A5 (it)
DE (1)	DE2827451A1 (it)
FR (1)	FR2395981A1 (it)
GB (1)	GB1598765A (it)
HU (1)	HU176093B (it)
IE (1)	IE47006B1 (it)
IL (1)	IL54994A (it)
IT (1)	IT1097262B (it)
NL (1)	NL7806729A (it)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2007051A1 (de) *	1970-02-17	1971-08-26	Farbenfabriken Bayer AG, 5090 Le verkusen	2,4 Bis (trifluormethyl) 6 nitroanihn Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als herbizide Mittel
US3726923A (en) *	1970-03-16	1973-04-10	Sherwin Williams Co	Process for the manufacture of n,n-dichloroalkyl-2,6-dinitro-4-alkyl aniline
ZA739198B (en) *	1972-12-11	1975-07-30	Lilly Co Eli	Herbicidal combinations for soybeans
IT1003177B (it) *	1973-10-16	1976-06-10	Snam Progetti	Procedimento per la idrogenazione catalitica di composti insaturi e catalizzatore utilizzabile in detto procediment

1978
- 1978-05-25 GB GB22598/78A patent/GB1598765A/en not_active Expired
- 1978-06-22 DE DE19782827451 patent/DE2827451A1/de not_active Withdrawn
- 1978-06-22 FR FR7818747A patent/FR2395981A1/fr active Granted
- 1978-06-22 NL NL7806729A patent/NL7806729A/xx not_active Application Discontinuation
- 1978-06-23 IE IE1255/78A patent/IE47006B1/en unknown
- 1978-06-23 HU HU78EI794A patent/HU176093B/hu unknown
- 1978-06-23 IL IL54994A patent/IL54994A/xx unknown
- 1978-06-23 AR AR272700A patent/AR219755A1/es active
- 1978-06-26 BR BR787804052A patent/BR7804052A/pt unknown
- 1978-06-26 IT IT24973/78A patent/IT1097262B/it active
- 1978-06-26 CH CH695578A patent/CH636840A5/de not_active IP Right Cessation
- 1978-06-27 JP JP7850778A patent/JPS5412330A/ja active Pending

Also Published As

Publication number	Publication date
IT1097262B (it)	1985-08-31
HU176093B (en)	1980-12-28
FR2395981B1 (it)	1981-07-24
IL54994A (en)	1981-06-29
CH636840A5 (en)	1983-06-30
IL54994A0 (en)	1978-08-31
JPS5412330A (en)	1979-01-30
DE2827451A1 (de)	1979-01-11
FR2395981A1 (fr)	1979-01-26
IE781255L (en)	1978-12-27
BR7804052A (pt)	1979-01-16
NL7806729A (nl)	1978-12-29
IT7824973A0 (it)	1978-06-26
GB1598765A (en)	1981-09-23
AR219755A1 (es)	1980-09-15

Publication	Publication Date	Title
US4314069A (en)	1982-02-02	Herbicidal compound, herbicidal composition containing the same, and method of use thereof
US4332960A (en)	1982-06-01	Herbicidal compositions
US5250690A (en)	1993-10-05	Haloalkoxy anilide derivatives of 2-4(-heterocyclic oxyphenoxy)alkanoic or alkenoic acids and their use as herbicides
USRE33745E (en)	1991-11-19	Thiadiazabicyclononane derivatives, processes for their production and herbicidal compositions
US4134753A (en)	1979-01-16	Herbicidal agents
US4595410A (en)	1986-06-17	Oxime derivatives of diphenyl ethers and their use in herbicidal compositions
EP0288275B1 (en)	1993-01-27	Phenoxypropionic acid derivatives for use as herbicides
US4493729A (en)	1985-01-15	N-Phenylcarbamoyl-pyridine compounds
US4143061A (en)	1979-03-06	3-(α,α-Dimethylbenzyl)urea compounds, compositions, and their use as herbicides
JPS5953917B2 (ja)	1984-12-27	テトラヒドロイソフタルイミド誘導体およびその製造方法
PL130861B1 (en)	1984-09-29	Herbicide and method of manufacture of novel substituted derivatives of phenylsulfonylurea
US4087460A (en)	1978-05-02	Substituted N-alkoxy-N-substituted-2,6-dinitroanilines and intermediates for the preparation thereof
US4304791A (en)	1981-12-08	Benzenamines, formulations, and fungicidal method
GB2029403A (en)	1980-03-19	Hercicidal pyridones and pyridinethiones
IE47006B1 (en)	1983-11-30	N-alkoxy-dinitro anilines and their herbicidal compositions
JP4169810B2 (ja)	2008-10-22	除草活性を有するアリール複素環類
CS201022B2 (en)	1980-10-31	Fungicide and method of preparing the active constituent
HU189334B (en)	1986-06-30	Herbicidal compositions comprising phenoxy-alkyl-amine-derivatives and process for preparing phenoxy-alkyl-amine-derivatives
KR810001028B1 (ko)	1981-08-31	N-알콕시-2,6-디니트로-4-치환된-아닐린의 제조방법
KR810001029B1 (ko)	1981-08-31	N-알콕시-2,6-디니트로-n-치환-4-치환-아닐린의 제조방법
CA1112668A (en)	1981-11-17	Process for preparing substituted n-alkoxy-n- substituted-2,6-dinitroanilines
JP2504072B2 (ja)	1996-06-05	置換ベンゾイル誘導体および除草剤
JPS601315B2 (ja)	1985-01-14	イミダゾール誘導体、その製造方法及び農園芸用殺菌剤
US4153730A (en)	1979-05-08	Fungicidal and herbicidal methods
NZ202387A (en)	1985-07-12	Herbicidal arylphenyl ether derivatives