NO813741L - Nye dinitro-anilin-derivater og anvendelse derav - Google Patents
Nye dinitro-anilin-derivater og anvendelse deravInfo
- Publication number
- NO813741L NO813741L NO813741A NO813741A NO813741L NO 813741 L NO813741 L NO 813741L NO 813741 A NO813741 A NO 813741A NO 813741 A NO813741 A NO 813741A NO 813741 L NO813741 L NO 813741L
- Authority
- NO
- Norway
- Prior art keywords
- dinitro
- dioxolan
- ylmethyl
- grams
- ethyl
- Prior art date
Links
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical class [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 2
- 241000196324 Embryophyta Species 0.000 claims description 42
- 238000002360 preparation method Methods 0.000 claims description 35
- 239000004480 active ingredient Substances 0.000 claims description 5
- 231100000331 toxic Toxicity 0.000 claims description 5
- 230000002588 toxic effect Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- OGCWJORGOZYUIH-UHFFFAOYSA-N n-(1,3-dioxolan-2-ylmethyl)-4-methyl-2,6-dinitro-n-propylaniline Chemical group [O-][N+](=O)C=1C=C(C)C=C([N+]([O-])=O)C=1N(CCC)CC1OCCO1 OGCWJORGOZYUIH-UHFFFAOYSA-N 0.000 claims description 2
- QCLZUEYQMKTLJU-UHFFFAOYSA-N n-(1,3-dioxolan-2-ylmethyl)-n-ethyl-4-methyl-2,6-dinitroaniline Chemical group [O-][N+](=O)C=1C=C(C)C=C([N+]([O-])=O)C=1N(CC)CC1OCCO1 QCLZUEYQMKTLJU-UHFFFAOYSA-N 0.000 claims description 2
- IJVMONIVBWHGEZ-UHFFFAOYSA-N n-(1,3-dioxolan-2-ylmethyl)-n-methyl-2,6-dinitro-4-(trifluoromethyl)aniline Chemical group [O-][N+](=O)C=1C=C(C(F)(F)F)C=C([N+]([O-])=O)C=1N(C)CC1OCCO1 IJVMONIVBWHGEZ-UHFFFAOYSA-N 0.000 claims description 2
- KERDTEJCGUTCKW-UHFFFAOYSA-N 4-tert-butyl-n-(1,3-dioxolan-2-ylmethyl)-n-ethyl-2,6-dinitroaniline Chemical group [O-][N+](=O)C=1C=C(C(C)(C)C)C=C([N+]([O-])=O)C=1N(CC)CC1OCCO1 KERDTEJCGUTCKW-UHFFFAOYSA-N 0.000 claims 1
- ZABRTPZTWKPSGS-UHFFFAOYSA-N 4-tert-butyl-n-ethyl-n-[(2-methyl-1,3-dioxolan-2-yl)methyl]-2,6-dinitroaniline Chemical group [O-][N+](=O)C=1C=C(C(C)(C)C)C=C([N+]([O-])=O)C=1N(CC)CC1(C)OCCO1 ZABRTPZTWKPSGS-UHFFFAOYSA-N 0.000 claims 1
- IOOHDHWHAGPLNM-UHFFFAOYSA-N n-(1,3-dioxolan-2-ylmethyl)-2,6-dinitro-n-propyl-4-(trifluoromethyl)aniline Chemical group [O-][N+](=O)C=1C=C(C(F)(F)F)C=C([N+]([O-])=O)C=1N(CCC)CC1OCCO1 IOOHDHWHAGPLNM-UHFFFAOYSA-N 0.000 claims 1
- AJISVYIPUKWMCU-UHFFFAOYSA-N n-(1,3-dioxolan-2-ylmethyl)-n,4-dimethyl-2,6-dinitroaniline Chemical group [O-][N+](=O)C=1C=C(C)C=C([N+]([O-])=O)C=1N(C)CC1OCCO1 AJISVYIPUKWMCU-UHFFFAOYSA-N 0.000 claims 1
- LXSAPNDAKCLWMG-UHFFFAOYSA-N n-(1,3-dioxolan-2-ylmethyl)-n-ethyl-2,6-dinitro-4-(trifluoromethyl)aniline Chemical group [O-][N+](=O)C=1C=C(C(F)(F)F)C=C([N+]([O-])=O)C=1N(CC)CC1OCCO1 LXSAPNDAKCLWMG-UHFFFAOYSA-N 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 29
- 239000000203 mixture Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 23
- 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
- 238000010992 reflux Methods 0.000 description 18
- 239000011521 glass Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 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
- 238000010438 heat treatment Methods 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- -1 diethoxyethyl Chemical group 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 230000002363 herbicidal effect Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- YSCNYKGRVUVJHA-UHFFFAOYSA-N 2,2-diethoxy-n-ethylethanamine Chemical compound CCNCC(OCC)OCC YSCNYKGRVUVJHA-UHFFFAOYSA-N 0.000 description 4
- 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
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 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 3
- 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 3
- 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
- 239000002253 acid Substances 0.000 description 3
- 239000003795 chemical substances by application 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
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 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 3
- WPKBVFTTZKQREB-UHFFFAOYSA-N n-(2,2-diethoxyethyl)propan-1-amine Chemical compound CCCNCC(OCC)OCC WPKBVFTTZKQREB-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000007858 starting material Substances 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
- QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-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
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 2
- 241001290610 Abildgaardia Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 2
- 240000006891 Artemisia vulgaris Species 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 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
- 239000000443 aerosol Substances 0.000 description 2
- 150000001350 alkyl halides Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000002837 defoliant Substances 0.000 description 2
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 description 2
- YMRPWLLTVHZUFP-UHFFFAOYSA-N n-[(2-methyl-1,3-dioxolan-2-yl)methyl]ethanamine Chemical compound CCNCC1(C)OCCO1 YMRPWLLTVHZUFP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- IMKBCTZRZWDYJE-UHFFFAOYSA-N 1,1-dimethoxy-n-propylpropan-2-amine Chemical compound CCCNC(C)C(OC)OC IMKBCTZRZWDYJE-UHFFFAOYSA-N 0.000 description 1
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 1
- JEZZOKXIXNSKQD-UHFFFAOYSA-N 1,3-bis(4-nitrophenyl)urea Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 JEZZOKXIXNSKQD-UHFFFAOYSA-N 0.000 description 1
- VTWOCLHRMQBXIS-UHFFFAOYSA-N 1-(1,1,4-trimethyl-6-propan-2-yl-2,3-dihydroinden-5-yl)propan-1-one;1-(3,3,7-trimethyl-5-propan-2-yl-1,2-dihydroinden-4-yl)propan-1-one Chemical compound C1=C(C(C)C)C(C(=O)CC)=C2C(C)(C)CCC2=C1C.C1=C(C(C)C)C(C(=O)CC)=C(C)C2=C1C(C)(C)CC2 VTWOCLHRMQBXIS-UHFFFAOYSA-N 0.000 description 1
- ZELUYVGCOWJMNP-UHFFFAOYSA-N 1-(4-chloro-3-nitrobutyl)-3-nitrobenzene Chemical compound [O-][N+](=O)C(CCl)CCC1=CC=CC([N+]([O-])=O)=C1 ZELUYVGCOWJMNP-UHFFFAOYSA-N 0.000 description 1
- WLKSPGHQGFFKGE-UHFFFAOYSA-N 1-chloropropan-2-yl n-(3-chlorophenyl)carbamate Chemical compound ClCC(C)OC(=O)NC1=CC=CC(Cl)=C1 WLKSPGHQGFFKGE-UHFFFAOYSA-N 0.000 description 1
- HUMIEJNVCICTPJ-UHFFFAOYSA-N 2,2-dimethoxy-n-methylethanamine Chemical compound CNCC(OC)OC HUMIEJNVCICTPJ-UHFFFAOYSA-N 0.000 description 1
- UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 description 1
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 1
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
- GKFWNPPZHDYVLI-UHFFFAOYSA-N 2,3-dichloropropanoic acid Chemical compound OC(=O)C(Cl)CCl GKFWNPPZHDYVLI-UHFFFAOYSA-N 0.000 description 1
- 239000002794 2,4-DB Substances 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- KBQPYERMRVPJDC-UHFFFAOYSA-N 2,4-dichloro-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1Cl KBQPYERMRVPJDC-UHFFFAOYSA-N 0.000 description 1
- PSOZMUMWCXLRKX-UHFFFAOYSA-N 2,4-dinitro-6-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O PSOZMUMWCXLRKX-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ISMLHZDOBNLSLN-UHFFFAOYSA-N 2-(2,3,5-trichloro-6-methoxyphenyl)acetic acid Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1CC(O)=O ISMLHZDOBNLSLN-UHFFFAOYSA-N 0.000 description 1
- LGURYBCSJPXHTF-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)ethyl benzoate Chemical compound ClC1=CC(Cl)=CC=C1OCCOC(=O)C1=CC=CC=C1 LGURYBCSJPXHTF-UHFFFAOYSA-N 0.000 description 1
- GWTUGCOXTFFBMM-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)acetic acid Chemical compound OC(=O)CC1=CC(Cl)=CC=C1Cl GWTUGCOXTFFBMM-UHFFFAOYSA-N 0.000 description 1
- UGFUXLOVLQUQST-UHFFFAOYSA-N 2-(2,6-dichloro-3-methoxyphenyl)acetic acid Chemical compound COC1=CC=C(Cl)C(CC(O)=O)=C1Cl UGFUXLOVLQUQST-UHFFFAOYSA-N 0.000 description 1
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
- CQQUWTMMFMJEFE-UHFFFAOYSA-N 2-chloro-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CCl CQQUWTMMFMJEFE-UHFFFAOYSA-N 0.000 description 1
- XBPPLECAZBTMMK-UHFFFAOYSA-N 2-chloro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CCl XBPPLECAZBTMMK-UHFFFAOYSA-N 0.000 description 1
- GYPNJSBBOATUPK-UHFFFAOYSA-N 2-chloro-n-propan-2-ylacetamide Chemical compound CC(C)NC(=O)CCl GYPNJSBBOATUPK-UHFFFAOYSA-N 0.000 description 1
- GYJQWEIGUGMFMU-UHFFFAOYSA-N 2-chloroethyl n-(3-chlorophenyl)carbamate Chemical compound ClCCOC(=O)NC1=CC=CC(Cl)=C1 GYJQWEIGUGMFMU-UHFFFAOYSA-N 0.000 description 1
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- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 229940096826 phenylmercuric acetate Drugs 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
- 230000008635 plant growth Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 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
- 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
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 229940010115 simetone Drugs 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 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
- KISFEBPWFCGRGN-UHFFFAOYSA-M sodium;2-(2,4-dichlorophenoxy)ethyl sulfate Chemical compound [Na+].[O-]S(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl KISFEBPWFCGRGN-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 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
- 230000036642 wellbeing Effects 0.000 description 1
- 235000005765 wild carrot 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
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/204,446 US4397677A (en) | 1979-11-29 | 1980-11-06 | Dioxolane substituted 2,6-dinitroanilines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO813741L true NO813741L (no) | 1982-05-07 |
Family
ID=22757912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO813741A NO813741L (no) | 1980-11-06 | 1981-11-05 | Nye dinitro-anilin-derivater og anvendelse derav |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4397677A (el) |
| JP (1) | JPS5782388A (el) |
| KR (1) | KR850001042B1 (el) |
| AR (1) | AR230993A1 (el) |
| AT (1) | AT380766B (el) |
| AU (1) | AU546224B2 (el) |
| BE (1) | BE891008A (el) |
| BG (1) | BG36784A3 (el) |
| BR (1) | BR8106305A (el) |
| CA (1) | CA1161856A (el) |
| CH (1) | CH648031A5 (el) |
| DD (1) | DD201966A5 (el) |
| DE (1) | DE3142736A1 (el) |
| DK (1) | DK490681A (el) |
| EG (1) | EG15542A (el) |
| ES (1) | ES8302690A1 (el) |
| FR (1) | FR2493319A1 (el) |
| GB (1) | GB2086899B (el) |
| GR (1) | GR74684B (el) |
| HU (1) | HU190679B (el) |
| IT (1) | IT1142839B (el) |
| NL (1) | NL8103883A (el) |
| NO (1) | NO813741L (el) |
| NZ (1) | NZ198081A (el) |
| PL (1) | PL127389B1 (el) |
| SE (1) | SE8106492L (el) |
| SU (1) | SU1162370A3 (el) |
| YU (1) | YU259481A (el) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL140861A (en) * | 1998-07-15 | 2004-06-01 | Bristol Myers Squibb Co | Dioxolane pentanoic acid and processes for the preparation thereof |
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 |
| US3946045A (en) * | 1974-11-13 | 1976-03-23 | Velsicol Chemical Corporation | Dioxolane substituted anilids |
| US4012222A (en) * | 1974-11-13 | 1977-03-15 | Velsicol Chemical Corporation | Herbicidal compositions containing dioxolane substituted anilids and method therefor |
| 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 active IP Right Grant
- 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/ES8302690A1/es not_active Expired
- 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 BG8153832A 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 CH CH7142/81A patent/CH648031A5/de not_active IP Right Cessation
- 1981-11-04 SU SU813352150A patent/SU1162370A3/ru active
- 1981-11-04 AU AU77079/81A patent/AU546224B2/en not_active Ceased
- 1981-11-05 BE BE0/206455A patent/BE891008A/fr not_active IP Right Cessation
- 1981-11-05 HU HU813307A patent/HU190679B/hu unknown
- 1981-11-05 DK DK490681A patent/DK490681A/da not_active Application Discontinuation
- 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 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 |
|---|---|
| HU190679B (en) | 1986-10-28 |
| PL127389B1 (en) | 1983-10-31 |
| AT380766B (de) | 1986-07-10 |
| NL8103883A (nl) | 1982-06-01 |
| NZ198081A (en) | 1984-07-31 |
| AU546224B2 (en) | 1985-08-22 |
| IT1142839B (it) | 1986-10-15 |
| US4397677A (en) | 1983-08-09 |
| SE8106492L (sv) | 1982-05-07 |
| GB2086899A (en) | 1982-05-19 |
| DD201966A5 (de) | 1983-08-24 |
| FR2493319A1 (fr) | 1982-05-07 |
| KR830006269A (ko) | 1983-09-20 |
| KR850001042B1 (ko) | 1985-07-19 |
| CA1161856A (en) | 1984-02-07 |
| BR8106305A (pt) | 1982-06-22 |
| IT8149387A0 (it) | 1981-09-28 |
| FR2493319B1 (el) | 1984-12-14 |
| PL232976A1 (el) | 1982-05-10 |
| GB2086899B (en) | 1984-09-05 |
| DE3142736A1 (de) | 1982-06-16 |
| EG15542A (en) | 1987-04-30 |
| AU7707981A (en) | 1982-05-13 |
| YU259481A (en) | 1983-09-30 |
| GR74684B (el) | 1984-07-03 |
| BG36784A3 (en) | 1985-01-15 |
| JPS5782388A (en) | 1982-05-22 |
| BE891008A (fr) | 1982-03-01 |
| SU1162370A3 (ru) | 1985-06-15 |
| AR230993A1 (es) | 1984-08-31 |
| ES505566A0 (es) | 1982-12-01 |
| ES8302690A1 (es) | 1982-12-01 |
| ATA475781A (de) | 1985-12-15 |
| CH648031A5 (de) | 1985-02-28 |
| DK490681A (da) | 1982-05-07 |
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