PL89154B1 - - Google Patents
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- PL89154B1 PL89154B1 PL1973162050A PL16205073A PL89154B1 PL 89154 B1 PL89154 B1 PL 89154B1 PL 1973162050 A PL1973162050 A PL 1973162050A PL 16205073 A PL16205073 A PL 16205073A PL 89154 B1 PL89154 B1 PL 89154B1
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- PL
- Poland
- Prior art keywords
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- plant
- compound
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- 241000196324 Embryophyta Species 0.000 claims description 15
- 239000013543 active substance Substances 0.000 claims description 14
- 244000068988 Glycine max Species 0.000 claims description 10
- 244000299507 Gossypium hirsutum Species 0.000 claims description 9
- 235000010469 Glycine max Nutrition 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 241000335053 Beta vulgaris Species 0.000 claims description 6
- 235000009432 Gossypium hirsutum Nutrition 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 6
- 235000007320 Avena fatua Nutrition 0.000 claims description 5
- 241000209764 Avena fatua Species 0.000 claims description 5
- 244000058871 Echinochloa crus-galli Species 0.000 claims description 5
- 240000008042 Zea mays Species 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 241001621841 Alopecurus myosuroides Species 0.000 claims description 4
- 244000025670 Eleusine indica Species 0.000 claims description 4
- 235000014716 Eleusine indica Nutrition 0.000 claims description 4
- 235000011999 Panicum crusgalli Nutrition 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 244000285774 Cyperus esculentus Species 0.000 claims description 3
- 235000005853 Cyperus esculentus Nutrition 0.000 claims description 3
- 240000007594 Oryza sativa Species 0.000 claims description 3
- 244000292693 Poa annua Species 0.000 claims description 3
- 241001355178 Setaria faberi Species 0.000 claims description 3
- 235000007244 Zea mays Nutrition 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 240000006597 Poa trivialis Species 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- DEARLNUFMWSREQ-UHFFFAOYSA-N sulfamoyl 2-hydroxyacetate Chemical class NS(=O)(=O)OC(=O)CO DEARLNUFMWSREQ-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 101150106303 AHSG gene Proteins 0.000 claims 1
- 241000548268 Citrus deliciosa Species 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 210000001699 lower leg Anatomy 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- -1 alkyl radical Chemical class 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical class NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 description 3
- 235000021537 Beetroot Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000021533 Beta vulgaris Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010410 dusting Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 240000004713 Pisum sativum Species 0.000 description 2
- 235000010582 Pisum sativum Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- BQKCJNGDDGMGEN-UHFFFAOYSA-N 1,3-dioxolane-2,4-dione Chemical compound O=C1COC(=O)O1 BQKCJNGDDGMGEN-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- RPSYMAMREDJAES-UHFFFAOYSA-N 2,5-dimethylmorpholine Chemical compound CC1COC(C)CN1 RPSYMAMREDJAES-UHFFFAOYSA-N 0.000 description 1
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- JODDYISEVBVLSB-UHFFFAOYSA-N 2-chloro-n-phenyl-n-propylacetamide Chemical compound CCCN(C(=O)CCl)C1=CC=CC=C1 JODDYISEVBVLSB-UHFFFAOYSA-N 0.000 description 1
- LGONGMXQDFYGKU-UHFFFAOYSA-N 2-methylazepane Chemical compound CC1CCCCCN1 LGONGMXQDFYGKU-UHFFFAOYSA-N 0.000 description 1
- LQMMFVPUIVBYII-UHFFFAOYSA-N 2-methylmorpholine Chemical compound CC1CNCCO1 LQMMFVPUIVBYII-UHFFFAOYSA-N 0.000 description 1
- LICHZOBEUWVYSY-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CNC2 LICHZOBEUWVYSY-UHFFFAOYSA-N 0.000 description 1
- DSBOHBZVJVNQRR-UHFFFAOYSA-N 3-methylazepane Chemical compound CC1CCCCNC1 DSBOHBZVJVNQRR-UHFFFAOYSA-N 0.000 description 1
- WKZHYWWKUYGHKO-UHFFFAOYSA-N 4-methylazepane Chemical compound CC1CCCNCC1 WKZHYWWKUYGHKO-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- VDTSEFXHWVBBKN-UHFFFAOYSA-N C(C)(C)NS(=O)(=O)OC(CO)=O Chemical compound C(C)(C)NS(=O)(=O)OC(CO)=O VDTSEFXHWVBBKN-UHFFFAOYSA-N 0.000 description 1
- 208000002881 Colic Diseases 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 235000007230 Sorghum bicolor Nutrition 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- SMLHHBQGIJMAIM-UHFFFAOYSA-N calcium;2-dodecylbenzenesulfonic acid Chemical compound [Ca].CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O SMLHHBQGIJMAIM-UHFFFAOYSA-N 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- SNQXJPARXFUULZ-UHFFFAOYSA-N dioxolane Chemical compound C1COOC1 SNQXJPARXFUULZ-UHFFFAOYSA-N 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 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 1
- 239000003350 kerosene Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- AGRDPCWQGGNEQL-UHFFFAOYSA-N n-propan-2-ylsulfamoyl chloride Chemical compound CC(C)NS(Cl)(=O)=O AGRDPCWQGGNEQL-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HNDXKIMMSFCCFW-UHFFFAOYSA-M propane-2-sulfonate Chemical compound CC(C)S([O-])(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-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
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2219923A DE2219923C3 (de) | 1972-04-22 | 1972-04-22 | Substituierte O- [Aminosulfonyl] -glykolsäureamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL89154B1 true PL89154B1 (en, 2012) | 1976-10-30 |
Family
ID=5843028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973162050A PL89154B1 (en, 2012) | 1972-04-22 | 1973-04-20 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3883509A (en, 2012) |
| JP (1) | JPS5838401B2 (en, 2012) |
| AR (1) | AR204611A1 (en, 2012) |
| AT (1) | AT322904B (en, 2012) |
| BE (1) | BE798530A (en, 2012) |
| BR (1) | BR7302881D0 (en, 2012) |
| CA (1) | CA1007231A (en, 2012) |
| CH (1) | CH568009A5 (en, 2012) |
| CS (1) | CS178423B2 (en, 2012) |
| DD (1) | DD103548A5 (en, 2012) |
| DE (1) | DE2219923C3 (en, 2012) |
| FR (1) | FR2181902B1 (en, 2012) |
| GB (1) | GB1419699A (en, 2012) |
| HU (1) | HU166065B (en, 2012) |
| IL (1) | IL42047A (en, 2012) |
| IT (1) | IT980318B (en, 2012) |
| MY (1) | MY7700079A (en, 2012) |
| NL (1) | NL7305378A (en, 2012) |
| OA (1) | OA04367A (en, 2012) |
| PH (1) | PH9910A (en, 2012) |
| PL (1) | PL89154B1 (en, 2012) |
| SU (1) | SU563893A3 (en, 2012) |
| TR (1) | TR17300A (en, 2012) |
| ZA (1) | ZA732593B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2453908A1 (de) * | 1974-11-14 | 1976-05-26 | Basf Ag | Herbizide mischungen |
| DE2454576A1 (de) * | 1974-11-18 | 1976-12-02 | Basf Ag | Herbizide mischungen |
| US4209317A (en) * | 1974-11-18 | 1980-06-24 | Basf Aktiengesellschaft | Herbicidal compositions |
| US4140517A (en) * | 1974-11-18 | 1979-02-20 | Basf Aktiengesellschaft | Herbicidal compositions |
| US4230863A (en) * | 1975-06-02 | 1980-10-28 | Shell Oil Company | Insecticidal sulfonium salts |
| JPS5350543A (en) * | 1976-10-20 | 1978-05-09 | Tokyo Gas Co Ltd | Insulator for embedded heater and its utilized matter |
| DE2852159A1 (de) * | 1978-12-02 | 1980-06-19 | Basf Ag | Verfahren zur herstellung von amidosulfonsaeuren |
| JPS5592366A (en) * | 1978-12-28 | 1980-07-12 | Hokko Chem Ind Co Ltd | O-sulfamoylglycolic acid amide derivative |
| DE2904490A1 (de) * | 1979-02-07 | 1980-08-21 | Bayer Ag | Verfahren zur herstellung von alpha -hydroxycarbonsaeureamiden |
| CN1336363A (zh) | 2001-07-25 | 2002-02-20 | 张元宾 | 乙酰磺胺酸钾的合成制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3536721A (en) * | 1963-09-13 | 1970-10-27 | Stauffer Chemical Co | Substituted-sulfonyl glycolamide compositions |
| US3798254A (en) * | 1971-09-20 | 1974-03-19 | Monsanto Co | Substituted s-dichloromethyl organothiosulfonates and their manufacture |
-
1972
- 1972-04-22 DE DE2219923A patent/DE2219923C3/de not_active Expired
-
1973
- 1973-01-01 AR AR247651A patent/AR204611A1/es active
- 1973-04-16 US US351240A patent/US3883509A/en not_active Expired - Lifetime
- 1973-04-16 IL IL42047A patent/IL42047A/xx unknown
- 1973-04-16 ZA ZA732593A patent/ZA732593B/xx unknown
- 1973-04-17 TR TR17300A patent/TR17300A/xx unknown
- 1973-04-17 NL NL7305378A patent/NL7305378A/xx unknown
- 1973-04-18 FR FR7314138A patent/FR2181902B1/fr not_active Expired
- 1973-04-18 BR BR2881/73A patent/BR7302881D0/pt unknown
- 1973-04-18 CH CH560373A patent/CH568009A5/xx not_active IP Right Cessation
- 1973-04-18 PH PH14527*A patent/PH9910A/en unknown
- 1973-04-18 SU SU7301909072A patent/SU563893A3/ru active
- 1973-04-19 DD DD170302A patent/DD103548A5/xx unknown
- 1973-04-19 OA OA54881A patent/OA04367A/xx unknown
- 1973-04-19 GB GB1892373A patent/GB1419699A/en not_active Expired
- 1973-04-19 CA CA169,933A patent/CA1007231A/en not_active Expired
- 1973-04-19 JP JP48043727A patent/JPS5838401B2/ja not_active Expired
- 1973-04-20 AT AT356873A patent/AT322904B/de not_active IP Right Cessation
- 1973-04-20 HU HUBA2920A patent/HU166065B/hu unknown
- 1973-04-20 BE BE130260A patent/BE798530A/xx unknown
- 1973-04-20 CS CS2902A patent/CS178423B2/cs unknown
- 1973-04-20 IT IT49609/73A patent/IT980318B/it active
- 1973-04-20 PL PL1973162050A patent/PL89154B1/pl unknown
-
1977
- 1977-12-30 MY MY79/77A patent/MY7700079A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR7302881D0 (pt) | 1974-01-08 |
| ZA732593B (en) | 1974-03-27 |
| IL42047A (en) | 1975-07-28 |
| DD103548A5 (en, 2012) | 1974-02-05 |
| PH9910A (en) | 1976-06-08 |
| FR2181902A1 (en, 2012) | 1973-12-07 |
| AR204611A1 (es) | 1976-02-20 |
| MY7700079A (en) | 1977-12-31 |
| AU5457573A (en) | 1974-10-17 |
| HU166065B (en, 2012) | 1975-01-28 |
| NL7305378A (en, 2012) | 1973-10-24 |
| US3883509A (en) | 1975-05-13 |
| IL42047A0 (en) | 1973-06-29 |
| CS178423B2 (en, 2012) | 1977-09-15 |
| OA04367A (fr) | 1980-01-31 |
| SU563893A3 (ru) | 1977-06-30 |
| CH568009A5 (en, 2012) | 1975-10-31 |
| DE2219923C3 (de) | 1979-07-05 |
| FR2181902B1 (en, 2012) | 1976-06-11 |
| IT980318B (it) | 1974-09-30 |
| BE798530A (fr) | 1973-10-22 |
| AT322904B (de) | 1975-06-10 |
| JPS5838401B2 (ja) | 1983-08-23 |
| GB1419699A (en, 2012) | 1975-12-31 |
| JPS4920331A (en, 2012) | 1974-02-22 |
| TR17300A (tr) | 1975-03-24 |
| CA1007231A (en) | 1977-03-22 |
| DE2219923B2 (de) | 1978-11-09 |
| DE2219923A1 (de) | 1973-10-31 |
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