NL8103883A - Door dioxolan gesubstitueerde 2,6-dinitroanilinen. - Google Patents
Door dioxolan gesubstitueerde 2,6-dinitroanilinen. Download PDFInfo
- Publication number
- NL8103883A NL8103883A NL8103883A NL8103883A NL8103883A NL 8103883 A NL8103883 A NL 8103883A NL 8103883 A NL8103883 A NL 8103883A NL 8103883 A NL8103883 A NL 8103883A NL 8103883 A NL8103883 A NL 8103883A
- Authority
- NL
- Netherlands
- Prior art keywords
- methyl
- dioxolan
- dinitro
- ethyl
- compound according
- Prior art date
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- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 44
- -1 dioxolan-substituted 2,6-dinitroanilines Chemical class 0.000 claims description 43
- 241000196324 Embryophyta Species 0.000 claims description 38
- 230000002363 herbicidal effect Effects 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- VUVXAPATRKKYNE-UHFFFAOYSA-N n-[3-methyl-2,6-dinitro-4-(trifluoromethyl)phenyl]-n-propyl-1,3-dioxolan-2-amine Chemical compound [O-][N+](=O)C=1C=C(C(F)(F)F)C(C)=C([N+]([O-])=O)C=1N(CCC)C1OCCO1 VUVXAPATRKKYNE-UHFFFAOYSA-N 0.000 claims description 2
- MFIMIBMRHXCFGE-UHFFFAOYSA-N n-methyl-n-[3-methyl-2,6-dinitro-4-(trifluoromethyl)phenyl]-1,3-dioxolan-2-amine Chemical compound [O-][N+](=O)C=1C=C(C(F)(F)F)C(C)=C([N+]([O-])=O)C=1N(C)C1OCCO1 MFIMIBMRHXCFGE-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 claims description 2
- UIOAQJNADLELPQ-UHFFFAOYSA-N C[C]1OCCO1 Chemical group C[C]1OCCO1 UIOAQJNADLELPQ-UHFFFAOYSA-N 0.000 claims 1
- NFZAANGMJOHMPL-UHFFFAOYSA-N N-(3,4-dimethyl-2,6-dinitrophenyl)-N-propyl-1,3-dioxolan-2-amine Chemical compound C(CC)N(C1=C(C(=C(C=C1[N+](=O)[O-])C)C)[N+](=O)[O-])C1OCCO1 NFZAANGMJOHMPL-UHFFFAOYSA-N 0.000 claims 1
- JYZIFENTPVBLJL-UHFFFAOYSA-N N-(4-tert-butyl-3-methyl-2,6-dinitrophenyl)-N-propyl-1,3-dioxolan-2-amine Chemical compound C(CC)N(C1=C(C(=C(C=C1[N+](=O)[O-])C(C)(C)C)C)[N+](=O)[O-])C1OCCO1 JYZIFENTPVBLJL-UHFFFAOYSA-N 0.000 claims 1
- 150000001448 anilines Chemical class 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
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- 239000000243 solution Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 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 6
- 206010061217 Infestation Diseases 0.000 description 6
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- YSCNYKGRVUVJHA-UHFFFAOYSA-N 2,2-diethoxy-n-ethylethanamine Chemical compound CCNCC(OCC)OCC YSCNYKGRVUVJHA-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 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 4
- FRFMLDNFLXIDSH-UHFFFAOYSA-N 5-tert-butyl-2-chloro-1,3-dinitrobenzene Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 FRFMLDNFLXIDSH-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- AQBOTXNCLZUHFP-UHFFFAOYSA-N n-(2,2-dimethoxyethyl)-n-methyl-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound COC(OC)CN(C)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O AQBOTXNCLZUHFP-UHFFFAOYSA-N 0.000 description 3
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- 239000002244 precipitate Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 2
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
- LADSNESNVGBQKO-UHFFFAOYSA-N 2-(bromomethyl)-2-methyl-1,3-dioxolane Chemical compound BrCC1(C)OCCO1 LADSNESNVGBQKO-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- 241000209136 Agropyron Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 2
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- 241000209082 Lolium Species 0.000 description 2
- DOUHNYYHAUJZDQ-UHFFFAOYSA-N N-ethyl-N-[3-methyl-2,6-dinitro-4-(trifluoromethyl)phenyl]-1,3-dioxolan-2-amine Chemical compound C(C)N(C1=C(C(=C(C=C1[N+](=O)[O-])C(F)(F)F)C)[N+](=O)[O-])C1OCCO1 DOUHNYYHAUJZDQ-UHFFFAOYSA-N 0.000 description 2
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- PNRAZZZISDRWMV-UHFFFAOYSA-N Terbucarb Chemical compound CNC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C PNRAZZZISDRWMV-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- SJBATLKARWYACW-UHFFFAOYSA-N n-(2,2-diethoxyethyl)-n-ethyl-4-methyl-2,6-dinitroaniline Chemical compound CCOC(OCC)CN(CC)C1=C([N+]([O-])=O)C=C(C)C=C1[N+]([O-])=O SJBATLKARWYACW-UHFFFAOYSA-N 0.000 description 2
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- YMRPWLLTVHZUFP-UHFFFAOYSA-N n-[(2-methyl-1,3-dioxolan-2-yl)methyl]ethanamine Chemical compound CCNCC1(C)OCCO1 YMRPWLLTVHZUFP-UHFFFAOYSA-N 0.000 description 1
- ZGANMTSKVWLRPT-UHFFFAOYSA-N n-methyl-n-propyl-1,3-dioxolan-2-amine Chemical compound CCCN(C)C1OCCO1 ZGANMTSKVWLRPT-UHFFFAOYSA-N 0.000 description 1
- IHPHPGLJYCDONF-UHFFFAOYSA-N n-propylacetamide Chemical compound CCCNC(C)=O IHPHPGLJYCDONF-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- XEBWQGVWTUSTLN-UHFFFAOYSA-M phenylmercury acetate Chemical compound CC(=O)O[Hg]C1=CC=CC=C1 XEBWQGVWTUSTLN-UHFFFAOYSA-M 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- 239000002373 plant growth inhibitor Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- HKAMKLBXTLTVCN-UHFFFAOYSA-N simeton Chemical compound CCNC1=NC(NCC)=NC(OC)=N1 HKAMKLBXTLTVCN-UHFFFAOYSA-N 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- NTOCDDPMRUNYHP-UHFFFAOYSA-M sodium;2-(2,4,5-trichlorophenoxy)ethyl sulfate Chemical compound [Na+].[O-]S(=O)(=O)OCCOC1=CC(Cl)=C(Cl)C=C1Cl NTOCDDPMRUNYHP-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000003971 tillage Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20444680 | 1980-11-06 | ||
| US06/204,446 US4397677A (en) | 1979-11-29 | 1980-11-06 | Dioxolane substituted 2,6-dinitroanilines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8103883A true NL8103883A (nl) | 1982-06-01 |
Family
ID=22757912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8103883A NL8103883A (nl) | 1980-11-06 | 1981-08-20 | Door dioxolan gesubstitueerde 2,6-dinitroanilinen. |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4397677A (cs) |
| JP (1) | JPS5782388A (cs) |
| KR (1) | KR850001042B1 (cs) |
| AR (1) | AR230993A1 (cs) |
| AT (1) | AT380766B (cs) |
| AU (1) | AU546224B2 (cs) |
| BE (1) | BE891008A (cs) |
| BG (1) | BG36784A3 (cs) |
| BR (1) | BR8106305A (cs) |
| CA (1) | CA1161856A (cs) |
| CH (1) | CH648031A5 (cs) |
| DD (1) | DD201966A5 (cs) |
| DE (1) | DE3142736A1 (cs) |
| DK (1) | DK490681A (cs) |
| EG (1) | EG15542A (cs) |
| ES (1) | ES505566A0 (cs) |
| FR (1) | FR2493319A1 (cs) |
| GB (1) | GB2086899B (cs) |
| GR (1) | GR74684B (cs) |
| HU (1) | HU190679B (cs) |
| IT (1) | IT1142839B (cs) |
| NL (1) | NL8103883A (cs) |
| NO (1) | NO813741L (cs) |
| NZ (1) | NZ198081A (cs) |
| PL (1) | PL127389B1 (cs) |
| SE (1) | SE8106492L (cs) |
| SU (1) | SU1162370A3 (cs) |
| YU (1) | YU259481A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0105151A3 (en) * | 1998-07-15 | 2004-11-29 | Bristol Myers Squibb Co | Preparation of (s)-2-amino-6,6-dimethoxyhexanoic acid methyl ester via novel dioxolanes |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3077393A (en) * | 1961-08-04 | 1963-02-12 | Stauffer Chemical Co | Method of controlling vegetative growth |
| US3257190A (en) * | 1962-12-10 | 1966-06-21 | Lilly Co Eli | Method of eliminating weed grasses and broadleaf weeds |
| GB1194727A (en) * | 1966-10-12 | 1970-06-10 | Sumitomo Chemical Co | Fungicidal Composition |
| US3518076A (en) * | 1967-05-17 | 1970-06-30 | Lilly Co Eli | Method of fliminating weed species with herbicidal combination |
| US3555045A (en) * | 1968-03-22 | 1971-01-12 | Standard Oil Co Ohio | 2-substituted-1,3-dioxolane compounds and method for preparing same |
| US3546295A (en) * | 1968-08-01 | 1970-12-08 | Exxon Research Engineering Co | N-cycloalkyl anilines |
| US3644422A (en) * | 1969-04-07 | 1972-02-22 | Sumitomo Chemical Co | 2-(substituted phenoxymethyl) dioxolanes |
| US4166908A (en) * | 1971-08-25 | 1979-09-04 | American Cyanamid Company | 2,6-Dinitroaniline herbicides |
| GB1401978A (en) * | 1971-11-29 | 1975-08-06 | Shell Int Research | Substituted cyclic 1,3-diethers and their use as herbicides |
| US3940259A (en) * | 1973-05-07 | 1976-02-24 | Velsicol Chemical Corporation | Dioxane substituted-α-haloanilides as herbicides |
| US3951640A (en) * | 1973-08-09 | 1976-04-20 | Velsicol Chemical Corporation | Heterocyclic thiadiazolylureas |
| US4046758A (en) * | 1974-03-05 | 1977-09-06 | United States Borax & Chemical Corporation | 3-Halo-2,6-dinitro-4-trifluoromethylanilines |
| US4022608A (en) * | 1974-08-01 | 1977-05-10 | Velsicol Chemical Corporation | N-α-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2-ethyl-6-methylaniline as a herbicide |
| US4012222A (en) * | 1974-11-13 | 1977-03-15 | Velsicol Chemical Corporation | Herbicidal compositions containing dioxolane substituted anilids and method therefor |
| US3946045A (en) * | 1974-11-13 | 1976-03-23 | Velsicol Chemical Corporation | Dioxolane substituted anilids |
| US4297127A (en) * | 1977-03-11 | 1981-10-27 | American Cyanamid Company | Herbicidal use of 2,6-dinitroaniline herbicides |
| US4113464A (en) * | 1977-04-04 | 1978-09-12 | Velsicol Chemical Company | Dioxolane substituted amides |
| US4118216A (en) * | 1977-04-25 | 1978-10-03 | Velsicol Chemical Company | N-dialkoxyalkyl-N-dioxolanalkylene-α-haloalkanamides |
| DE2802211A1 (de) * | 1978-01-19 | 1979-07-26 | Basf Ag | N-substituierte 2,6-dialkylaniline und verfahren zur herstellung von n- substituierten 2,6-dialkylanilinen |
| US4155745A (en) * | 1978-04-04 | 1979-05-22 | Stauffer Chemical Company | Certain 2-(chloroacetylamino)methyl-1,3-dioxolanes, thioxalanes or dithiolanes as herbicides |
| US4225335A (en) * | 1979-06-21 | 1980-09-30 | Velsicol Chemical Corporation | Dioxolane substituted acetanilids |
-
1980
- 1980-11-06 US US06/204,446 patent/US4397677A/en not_active Expired - Lifetime
-
1981
- 1981-08-11 CA CA000383601A patent/CA1161856A/en not_active Expired
- 1981-08-18 NZ NZ198081A patent/NZ198081A/en unknown
- 1981-08-20 NL NL8103883A patent/NL8103883A/nl not_active Application Discontinuation
- 1981-08-26 KR KR1019810003118A patent/KR850001042B1/ko not_active Expired
- 1981-09-01 AR AR286615A patent/AR230993A1/es active
- 1981-09-10 PL PL1981232976A patent/PL127389B1/pl unknown
- 1981-09-11 JP JP56143723A patent/JPS5782388A/ja active Pending
- 1981-09-17 ES ES505566A patent/ES505566A0/es active Granted
- 1981-09-28 IT IT49387/81A patent/IT1142839B/it active
- 1981-09-30 BR BR8106305A patent/BR8106305A/pt unknown
- 1981-10-03 EG EG565/81A patent/EG15542A/xx active
- 1981-10-13 BG BG053832A patent/BG36784A3/xx unknown
- 1981-10-28 DE DE19813142736 patent/DE3142736A1/de not_active Withdrawn
- 1981-10-29 GR GR66382A patent/GR74684B/el unknown
- 1981-11-02 YU YU02594/81A patent/YU259481A/xx unknown
- 1981-11-03 SE SE8106492A patent/SE8106492L/xx not_active Application Discontinuation
- 1981-11-04 SU SU813352150A patent/SU1162370A3/ru active
- 1981-11-04 AU AU77079/81A patent/AU546224B2/en not_active Ceased
- 1981-11-04 CH CH7142/81A patent/CH648031A5/de not_active IP Right Cessation
- 1981-11-05 GB GB8133340A patent/GB2086899B/en not_active Expired
- 1981-11-05 DD DD81234653A patent/DD201966A5/de unknown
- 1981-11-05 NO NO813741A patent/NO813741L/no unknown
- 1981-11-05 HU HU813307A patent/HU190679B/hu unknown
- 1981-11-05 DK DK490681A patent/DK490681A/da not_active Application Discontinuation
- 1981-11-05 BE BE0/206455A patent/BE891008A/fr not_active IP Right Cessation
- 1981-11-05 AT AT0475781A patent/AT380766B/de not_active IP Right Cessation
- 1981-11-06 FR FR8120876A patent/FR2493319A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NZ198081A (en) | 1984-07-31 |
| CH648031A5 (de) | 1985-02-28 |
| FR2493319B1 (cs) | 1984-12-14 |
| ATA475781A (de) | 1985-12-15 |
| DK490681A (da) | 1982-05-07 |
| HU190679B (en) | 1986-10-28 |
| EG15542A (en) | 1987-04-30 |
| YU259481A (en) | 1983-09-30 |
| ES8302690A1 (es) | 1982-12-01 |
| JPS5782388A (en) | 1982-05-22 |
| BG36784A3 (en) | 1985-01-15 |
| DD201966A5 (de) | 1983-08-24 |
| NO813741L (no) | 1982-05-07 |
| BR8106305A (pt) | 1982-06-22 |
| AU7707981A (en) | 1982-05-13 |
| PL127389B1 (en) | 1983-10-31 |
| SE8106492L (sv) | 1982-05-07 |
| CA1161856A (en) | 1984-02-07 |
| ES505566A0 (es) | 1982-12-01 |
| PL232976A1 (cs) | 1982-05-10 |
| BE891008A (fr) | 1982-03-01 |
| KR830006269A (ko) | 1983-09-20 |
| FR2493319A1 (fr) | 1982-05-07 |
| GR74684B (cs) | 1984-07-03 |
| AR230993A1 (es) | 1984-08-31 |
| KR850001042B1 (ko) | 1985-07-19 |
| IT8149387A0 (it) | 1981-09-28 |
| AT380766B (de) | 1986-07-10 |
| US4397677A (en) | 1983-08-09 |
| DE3142736A1 (de) | 1982-06-16 |
| SU1162370A3 (ru) | 1985-06-15 |
| GB2086899B (en) | 1984-09-05 |
| AU546224B2 (en) | 1985-08-22 |
| IT1142839B (it) | 1986-10-15 |
| GB2086899A (en) | 1982-05-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| CNR | Transfer of rights (patent application after its laying open for public inspection) |
Free format text: SANDOZ LTD. |
|
| BV | The patent application has lapsed |