NO118883B - - Google Patents
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- NO118883B NO118883B NO152166A NO15216664A NO118883B NO 118883 B NO118883 B NO 118883B NO 152166 A NO152166 A NO 152166A NO 15216664 A NO15216664 A NO 15216664A NO 118883 B NO118883 B NO 118883B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- salts
- mixed
- proportions
- compounds
- Prior art date
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- 150000003839 salts Chemical class 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000004009 herbicide Substances 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- -1 hexahydroindanyl Chemical group 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 26
- FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical class O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 19
- 230000002363 herbicidal effect Effects 0.000 description 18
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 235000012827 Digitaria sp Nutrition 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 244000025254 Cannabis sativa Species 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000004927 clay Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 244000045561 useful plants Species 0.000 description 5
- 241000508725 Elymus repens Species 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000008029 eradication Effects 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 244000024671 Brassica kaber Species 0.000 description 2
- 235000014750 Brassica kaber Nutrition 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- 241000192043 Echinochloa Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 241000404133 Leucanthemum Species 0.000 description 2
- 240000004658 Medicago sativa Species 0.000 description 2
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 244000308495 Potentilla anserina Species 0.000 description 2
- 235000016594 Potentilla anserina Nutrition 0.000 description 2
- 240000002439 Sorghum halepense Species 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001602 bicycloalkyls Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- 150000003672 ureas 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
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- UAUSQEVPWPGBHG-IHWYPQMZSA-N (z)-3-aminobut-2-enamide Chemical compound C\C(N)=C\C(N)=O UAUSQEVPWPGBHG-IHWYPQMZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IWXIRQBHVQKHET-UHFFFAOYSA-N 1-acetyl-5-bromo-3-butan-2-yl-6-methylpyrimidine-2,4-dione Chemical compound CCC(C)N1C(=O)C(Br)=C(C)N(C(C)=O)C1=O IWXIRQBHVQKHET-UHFFFAOYSA-N 0.000 description 1
- DZUZRTLWQRSCPZ-UHFFFAOYSA-N 1-acetyl-5-bromo-6-methyl-3-propan-2-ylpyrimidine-2,4-dione Chemical compound CC(C)N1C(=O)C(Br)=C(C)N(C(C)=O)C1=O DZUZRTLWQRSCPZ-UHFFFAOYSA-N 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-M 2,2-Dichloropropanoate Chemical compound CC(Cl)(Cl)C([O-])=O NDUPDOJHUQKPAG-UHFFFAOYSA-M 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
- AUAXYMOBWXOEQD-UHFFFAOYSA-N 2,5-dichloro-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC([N+]([O-])=O)=C1Cl AUAXYMOBWXOEQD-UHFFFAOYSA-N 0.000 description 1
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-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
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- PYSWMLOJSZEZCM-UHFFFAOYSA-N 3,6-dichloro-2-methylbenzoic acid Chemical compound CC1=C(Cl)C=CC(Cl)=C1C(O)=O PYSWMLOJSZEZCM-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- CCLXSTJSEGPTSF-UHFFFAOYSA-N 3-butan-2-yl-5-chloro-1h-pyrimidine-2,4-dione Chemical compound CCC(C)N1C(=O)NC=C(Cl)C1=O CCLXSTJSEGPTSF-UHFFFAOYSA-N 0.000 description 1
- JKKNEWPETSJXPC-UHFFFAOYSA-N 3-butan-2-yl-5-chloro-6-methyl-1h-pyrimidine-2,4-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Cl)C1=O JKKNEWPETSJXPC-UHFFFAOYSA-N 0.000 description 1
- IDNUMLACDURCBF-UHFFFAOYSA-N 3-cyclohexyl-6-ethyl-1h-pyrimidine-2,4-dione Chemical compound O=C1NC(CC)=CC(=O)N1C1CCCCC1 IDNUMLACDURCBF-UHFFFAOYSA-N 0.000 description 1
- BQIRNRIZIZRGCN-UHFFFAOYSA-N 3-cyclohexyl-6-methyl-1h-pyrimidine-2,4-dione Chemical compound O=C1NC(C)=CC(=O)N1C1CCCCC1 BQIRNRIZIZRGCN-UHFFFAOYSA-N 0.000 description 1
- PJMSNWHPGVLFQE-UHFFFAOYSA-N 3-cyclohexyl-6-propan-2-yl-1h-pyrimidine-2,4-dione Chemical compound O=C1NC(C(C)C)=CC(=O)N1C1CCCCC1 PJMSNWHPGVLFQE-UHFFFAOYSA-N 0.000 description 1
- XQBXHPGRDQFNRE-UHFFFAOYSA-N 3-cyclopentyl-6-methyl-1h-pyrimidine-2,4-dione Chemical compound O=C1NC(C)=CC(=O)N1C1CCCC1 XQBXHPGRDQFNRE-UHFFFAOYSA-N 0.000 description 1
- YTGYYQQZYMRDLV-UHFFFAOYSA-N 4-(2,4-dichlorophenoxy)butanoic acid 2,2-dichloro-5-(2,4,5-trichlorophenoxy)pentanoic acid Chemical compound ClC1=C(OCCCC(=O)O)C=CC(=C1)Cl.ClC1=C(OCCCC(C(=O)O)(Cl)Cl)C=C(C(=C1)Cl)Cl YTGYYQQZYMRDLV-UHFFFAOYSA-N 0.000 description 1
- MEAIOSRMRKDKKY-UHFFFAOYSA-N 4h-oxazin-3-one;hydrochloride Chemical compound Cl.O=C1CC=CON1 MEAIOSRMRKDKKY-UHFFFAOYSA-N 0.000 description 1
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
- MDOQZDIZLVBOMT-UHFFFAOYSA-N 5-bromo-3-butan-2-yl-1h-pyrimidine-2,4-dione Chemical compound CCC(C)N1C(=O)NC=C(Br)C1=O MDOQZDIZLVBOMT-UHFFFAOYSA-N 0.000 description 1
- VXARUOXETPLQOW-UHFFFAOYSA-N 5-bromo-3-cyclohexyl-6-methyl-1h-pyrimidine-2,4-dione Chemical compound O=C1C(Br)=C(C)NC(=O)N1C1CCCCC1 VXARUOXETPLQOW-UHFFFAOYSA-N 0.000 description 1
- DSFXMGCKOKZNCS-UHFFFAOYSA-N 5-bromo-3-propan-2-yl-1h-pyrimidine-2,4-dione Chemical compound CC(C)N1C(=O)NC=C(Br)C1=O DSFXMGCKOKZNCS-UHFFFAOYSA-N 0.000 description 1
- YYMYRMCMKDXWKV-UHFFFAOYSA-N 5-bromo-6-methyl-3-(4-methylpentan-2-yl)-1H-pyrimidine-2,4-dione Chemical compound BrC=1C(N(C(NC1C)=O)C(CC(C)C)C)=O YYMYRMCMKDXWKV-UHFFFAOYSA-N 0.000 description 1
- QMASYZYAMUINDL-UHFFFAOYSA-N 5-bromo-6-methyl-3-phenyl-1h-pyrimidine-2,4-dione Chemical compound O=C1C(Br)=C(C)NC(=O)N1C1=CC=CC=C1 QMASYZYAMUINDL-UHFFFAOYSA-N 0.000 description 1
- INFSAFKEHJEICZ-UHFFFAOYSA-N 5-chloro-6-methyl-3-pentan-3-yl-1h-pyrimidine-2,4-dione Chemical compound CCC(CC)N1C(=O)NC(C)=C(Cl)C1=O INFSAFKEHJEICZ-UHFFFAOYSA-N 0.000 description 1
- IJODTAPBLFUWHW-UHFFFAOYSA-N 5-chloro-6-methyl-3-propan-2-yl-1-(trichloromethylsulfanyl)pyrimidine-2,4-dione Chemical compound CC(C)N1C(=O)C(Cl)=C(C)N(SC(Cl)(Cl)Cl)C1=O IJODTAPBLFUWHW-UHFFFAOYSA-N 0.000 description 1
- CKUWCLSVZJSGIZ-UHFFFAOYSA-N 6-butan-2-yl-3-cyclohexyl-1h-pyrimidine-2,4-dione Chemical compound O=C1NC(C(C)CC)=CC(=O)N1C1CCCCC1 CKUWCLSVZJSGIZ-UHFFFAOYSA-N 0.000 description 1
- HUGIBYCJECJENZ-UHFFFAOYSA-N 6-chloro-2-N,4-N-bis(3-methoxypropyl)-1,3,5-triazine-2,4-diamine 6-chloro-4-N-ethyl-2-N-propan-2-yl-1,3,5-triazine-2,4-diamine 6-methoxy-2-N,4-N-di(propan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound COC1=NC(=NC(=N1)NC(C)C)NC(C)C.ClC1=NC(=NC(=N1)NCCCOC)NCCCOC.ClC1=NC(=NC(=N1)NCC)NC(C)C HUGIBYCJECJENZ-UHFFFAOYSA-N 0.000 description 1
- AJNUCEOPUCGIEL-UHFFFAOYSA-N 6-chloro-2-N,4-N-di(propan-2-yl)-1,3,5-triazine-2,4-diamine 2-N,4-N-diethyl-6-methoxy-1,3,5-triazine-2,4-diamine 4-N-ethyl-6-methoxy-2-N-propan-2-yl-1,3,5-triazine-2,4-diamine 4-N-ethyl-6-methylsulfanyl-2-N-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound ClC1=NC(=NC(=N1)NC(C)C)NC(C)C.COC1=NC(=NC(=N1)NCC)NC(C)C.COC1=NC(=NC(=N1)NCC)NCC.CSC1=NC(=NC(=N1)NCC)NC(C)C AJNUCEOPUCGIEL-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- GEHMBYLTCISYNY-UHFFFAOYSA-N Ammonium sulfamate Chemical compound [NH4+].NS([O-])(=O)=O GEHMBYLTCISYNY-UHFFFAOYSA-N 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- XOJVHLIYNSOZOO-SWOBOCGESA-N Arctiin Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H]1[C@@H](CC=2C=C(OC)C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)=CC=2)C(=O)OC1 XOJVHLIYNSOZOO-SWOBOCGESA-N 0.000 description 1
- 241000208843 Arctium Species 0.000 description 1
- 244000003416 Asparagus officinalis Species 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26149563A | 1963-02-27 | 1963-02-27 | |
| US343112A US3352662A (en) | 1963-02-27 | 1964-02-06 | Method of inhibiting growth of undesired vegetation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO118883B true NO118883B (ko) | 1970-02-23 |
Family
ID=26948646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO152166A NO118883B (ko) | 1963-02-27 | 1964-02-26 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3352662A (ko) |
| BE (1) | BE644357A (ko) |
| BR (1) | BR6456168D0 (ko) |
| CH (1) | CH450810A (ko) |
| DE (2) | DE1567016A1 (ko) |
| DK (1) | DK129683B (ko) |
| ES (1) | ES296865A1 (ko) |
| GB (1) | GB1060741A (ko) |
| MY (1) | MY6800030A (ko) |
| NL (1) | NL141358B (ko) |
| NO (1) | NO118883B (ko) |
| SE (1) | SE319478B (ko) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3451802A (en) * | 1966-06-27 | 1969-06-24 | Gulf Research Development Co | Triazine herbicides |
| US3442640A (en) * | 1966-11-22 | 1969-05-06 | Givaudan Corp | Methods of destroying weeds with substituted tetralins |
| US3529952A (en) * | 1968-09-17 | 1970-09-22 | Du Pont | Plant control with 5-oxo-1,4,2-dioxazines |
| US3839010A (en) * | 1970-05-19 | 1974-10-01 | Exxon Research Engineering Co | Thiocarbamic acid ester pesticides |
| US4632698A (en) * | 1983-09-02 | 1986-12-30 | Union Carbide Corporation | Biocidal 2-aryl-1,3-cyclopentanedione enol ester compounds |
| DE19604582A1 (de) | 1996-02-08 | 1997-08-14 | Bayer Ag | Verfahren zur Herstellung von substituierten Cyanophenyluracilen, neue substituierte Aminoalkensäure-cyanophenylamide als Zwischenprodukte hierfür und Verfahren zu deren Herstellung |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2797217A (en) * | 1957-06-25 | Dihydro oxazine diones | ||
| US2758994A (en) * | 1956-08-14 | Production | ||
| US2329619A (en) * | 1941-09-04 | 1943-09-14 | American Cyanamld Company | mu-substituted oxazolines, mu-substituted pentoxazolines, and methods for their preparation |
| US2447822A (en) * | 1946-02-25 | 1948-08-24 | Commercial Solvents Corp | 5-nitrotetrahydro-1, 3-oxazines and method for preparing them |
| US3037853A (en) * | 1958-04-04 | 1962-06-05 | Du Pont | Herbicidal composition and method employing a mixture of ethyl n, n-dipropylthiolcarbamate and a herbicidal s-triazine |
| US3235357A (en) * | 1959-08-14 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| BE600423A (ko) * | 1960-02-23 | |||
| US3210355A (en) * | 1963-03-06 | 1965-10-05 | Ciba Geigy Corp | Pyrimidinones and process of preparing same |
| US3223707A (en) * | 1963-12-23 | 1965-12-14 | Stauffer Chemical Co | 2-(trifluorobutenylmercapto)-pyrimidines |
-
1964
- 1964-01-17 BR BR156168/64A patent/BR6456168D0/pt unknown
- 1964-02-06 US US343112A patent/US3352662A/en not_active Expired - Lifetime
- 1964-02-25 DE DE19641567016 patent/DE1567016A1/de active Pending
- 1964-02-25 DE DE19641620107 patent/DE1620107A1/de active Pending
- 1964-02-25 ES ES0296865A patent/ES296865A1/es not_active Expired
- 1964-02-26 SE SE2363/64A patent/SE319478B/xx unknown
- 1964-02-26 CH CH236364A patent/CH450810A/de unknown
- 1964-02-26 BE BE644357D patent/BE644357A/fr unknown
- 1964-02-26 DK DK94864AA patent/DK129683B/da unknown
- 1964-02-26 GB GB8075/64A patent/GB1060741A/en not_active Expired
- 1964-02-26 NL NL646401832A patent/NL141358B/xx unknown
- 1964-02-26 NO NO152166A patent/NO118883B/no unknown
-
1968
- 1968-12-31 MY MY196830A patent/MY6800030A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY6800030A (en) | 1968-12-31 |
| US3352662A (en) | 1967-11-14 |
| BE644357A (ko) | 1964-08-26 |
| DE1567016A1 (de) | 1970-04-16 |
| ES296865A1 (es) | 1964-05-01 |
| CH450810A (de) | 1968-04-30 |
| SE319478B (ko) | 1970-01-19 |
| GB1060741A (en) | 1967-03-08 |
| DE1620107A1 (de) | 1970-03-05 |
| DK129683B (da) | 1974-11-11 |
| NL6401832A (ko) | 1964-08-28 |
| BR6456168D0 (pt) | 1973-08-09 |
| NL141358B (nl) | 1974-03-15 |
| DK129683C (ko) | 1975-04-21 |
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