DD210260A5 - Verfahren zur herstellung von carbonsaeureamido-thiolcarbamat-derivaten - Google Patents
Verfahren zur herstellung von carbonsaeureamido-thiolcarbamat-derivaten Download PDFInfo
- Publication number
- DD210260A5 DD210260A5 DD82250403A DD25040382A DD210260A5 DD 210260 A5 DD210260 A5 DD 210260A5 DD 82250403 A DD82250403 A DD 82250403A DD 25040382 A DD25040382 A DD 25040382A DD 210260 A5 DD210260 A5 DD 210260A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- ethyl
- phenyl
- group
- hydrogen
- propyl
- Prior art date
Links
- -1 THIOL CARBAMATE DERIVATIVES Chemical class 0.000 title abstract description 78
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 59
- 239000001257 hydrogen Substances 0.000 claims abstract description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 29
- 238000002360 preparation method Methods 0.000 abstract description 27
- 239000002253 acid Substances 0.000 abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 239000011230 binding agent Substances 0.000 abstract description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 14
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 8
- 235000003222 Helianthus annuus Nutrition 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 239000004563 wettable powder Substances 0.000 description 8
- 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 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 235000013339 cereals Nutrition 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009395 breeding Methods 0.000 description 6
- 230000001488 breeding effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000208818 Helianthus Species 0.000 description 4
- 244000020551 Helianthus annuus Species 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- 235000005775 Setaria Nutrition 0.000 description 4
- 241000232088 Setaria <nematode> Species 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 244000230030 foxtail bristlegrass Species 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 240000001980 Cucurbita pepo Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 240000006394 Sorghum bicolor Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 235000009973 maize Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 230000004936 stimulating effect Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 2
- 235000000832 Ayote Nutrition 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 244000241257 Cucumis melo Species 0.000 description 2
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
- 235000009854 Cucurbita moschata Nutrition 0.000 description 2
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 240000004713 Pisum sativum Species 0.000 description 2
- 235000010582 Pisum sativum Nutrition 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 235000007244 Zea mays Nutrition 0.000 description 2
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000000729 antidote Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003864 humus Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 235000015136 pumpkin Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- WQRPHHIOZYGAMQ-UHFFFAOYSA-N 3-methyl-n-phenylbutanamide Chemical compound CC(C)CC(=O)NC1=CC=CC=C1 WQRPHHIOZYGAMQ-UHFFFAOYSA-N 0.000 description 1
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
- UKYGKNHLXAIOQN-UHFFFAOYSA-N 6-methylidenecyclohexa-2,4-dien-1-ol Chemical compound OC1C=CC=CC1=C UKYGKNHLXAIOQN-UHFFFAOYSA-N 0.000 description 1
- BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- DGNHZYWHYUWXRM-UHFFFAOYSA-N C(C)(=O)NC1=CC=CC=C1.[Cl] Chemical class C(C)(=O)NC1=CC=CC=C1.[Cl] DGNHZYWHYUWXRM-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 244000241235 Citrullus lanatus Species 0.000 description 1
- 235000009831 Citrullus lanatus Nutrition 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- 240000004585 Dactylis glomerata Species 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 241000208204 Linum Species 0.000 description 1
- 101150014717 LysP gene Proteins 0.000 description 1
- SNPZDXACCGIJNK-UHFFFAOYSA-N N-Acetyl-2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1NC(C)=O SNPZDXACCGIJNK-UHFFFAOYSA-N 0.000 description 1
- PWTOMWQKTVMNMM-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOOOOOO PWTOMWQKTVMNMM-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241001466551 Piaya Species 0.000 description 1
- 241000219000 Populus Species 0.000 description 1
- 241000218206 Ranunculus Species 0.000 description 1
- 241000220259 Raphanus Species 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000002605 anti-dotal effect Effects 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000002178 crystalline material Substances 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
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000006266 hibernation Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 235000021581 juice product Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000002609 medium Substances 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
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000019713 millet Nutrition 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000843 powder Substances 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
- 235000021251 pulses Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000005303 weighing Methods 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (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)
- Carbon And Carbon Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU812794A HU183589B (en) | 1981-09-29 | 1981-09-29 | Herbicide composition containing carboxylic acid-amido-thiol-carbamate derivatives and process for preparing the active substances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD210260A5 true DD210260A5 (de) | 1984-06-06 |
Family
ID=10961120
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82250403A DD210260A5 (de) | 1981-09-29 | 1982-09-27 | Verfahren zur herstellung von carbonsaeureamido-thiolcarbamat-derivaten |
| DD82243523A DD204608A5 (de) | 1981-09-29 | 1982-09-27 | Unkrautbekaempfungsmittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82243523A DD204608A5 (de) | 1981-09-29 | 1982-09-27 | Unkrautbekaempfungsmittel |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4559083A (cs) |
| AT (1) | AT381618B (cs) |
| BE (1) | BE894492A (cs) |
| BG (2) | BG40653A3 (cs) |
| CA (1) | CA1217766A (cs) |
| CH (1) | CH655305A5 (cs) |
| CS (1) | CS235963B2 (cs) |
| DD (2) | DD210260A5 (cs) |
| DE (1) | DE3236097A1 (cs) |
| DK (1) | DK430682A (cs) |
| FR (1) | FR2513485B1 (cs) |
| GB (1) | GB2106518B (cs) |
| GR (1) | GR77658B (cs) |
| HU (1) | HU183589B (cs) |
| IT (1) | IT1210938B (cs) |
| NL (1) | NL8203767A (cs) |
| PL (1) | PL135607B1 (cs) |
| PT (1) | PT75613B (cs) |
| RO (1) | RO88971A (cs) |
| SU (2) | SU1416045A3 (cs) |
| TR (1) | TR21704A (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5504109A (en) * | 1989-05-13 | 1996-04-02 | Bayer Aktiengesellschaft | Susbstituted amino acid amide derivatives their preparation and use |
| DE3915755A1 (de) * | 1989-05-13 | 1990-11-29 | Bayer Ag | Fungizide mittel sowie substituierte aminosaeureamid-derivate und deren herstellung |
| DE4203084A1 (de) * | 1992-02-04 | 1993-08-05 | Bayer Ag | Substituierte aminosaeureamide |
| CN102452959A (zh) * | 2010-10-20 | 2012-05-16 | 中国农业科学院植物保护研究所 | 取代的缬氨酰胺衍生物及其制备 |
| USD951590S1 (en) * | 2019-12-16 | 2022-05-17 | LaShonda Epps | Pocket bra |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4108885A (en) * | 1967-08-25 | 1978-08-22 | Schering Ag | Salts of thiocarbamic esters with fungicidal and fungistatic action |
| US3493360A (en) * | 1968-05-14 | 1970-02-03 | Stauffer Chemical Co | Herbicides |
| US3897474A (en) * | 1972-10-12 | 1975-07-29 | Ciba Geigy Corp | Thiol and dithiol carbamate acid ester derivatives of phenyl formamidine |
| JPS52153935A (en) * | 1976-06-11 | 1977-12-21 | Kyowa Hakko Kogyo Co Ltd | Novel sarocosine derivatives and herbicides containing same |
| JPS52151146A (en) * | 1976-06-11 | 1977-12-15 | Kyowa Hakko Kogyo Co Ltd | Novel thiocarbonylamino acid derivatives and novel herbicides containing same |
| JPS53148530A (en) * | 1977-05-27 | 1978-12-25 | Kyowa Hakko Kogyo Co Ltd | Agricultural and horticultural fungicide |
-
1981
- 1981-09-29 HU HU812794A patent/HU183589B/hu unknown
-
1982
- 1982-09-22 AT AT0352182A patent/AT381618B/de not_active IP Right Cessation
- 1982-09-22 US US06/421,238 patent/US4559083A/en not_active Expired - Fee Related
- 1982-09-24 TR TR21704A patent/TR21704A/xx unknown
- 1982-09-27 BE BE1/10596A patent/BE894492A/fr not_active IP Right Cessation
- 1982-09-27 DD DD82250403A patent/DD210260A5/de unknown
- 1982-09-27 DD DD82243523A patent/DD204608A5/de unknown
- 1982-09-28 SU SU823494193A patent/SU1416045A3/ru active
- 1982-09-28 FR FR8216274A patent/FR2513485B1/fr not_active Expired
- 1982-09-28 PL PL1982238404A patent/PL135607B1/pl unknown
- 1982-09-28 DK DK430682A patent/DK430682A/da not_active Application Discontinuation
- 1982-09-28 PT PT75613A patent/PT75613B/pt unknown
- 1982-09-28 CH CH5695/82A patent/CH655305A5/de not_active IP Right Cessation
- 1982-09-28 CA CA000412374A patent/CA1217766A/en not_active Expired
- 1982-09-28 GR GR69384A patent/GR77658B/el unknown
- 1982-09-28 IT IT8223463A patent/IT1210938B/it active
- 1982-09-28 GB GB08227657A patent/GB2106518B/en not_active Expired
- 1982-09-29 DE DE19823236097 patent/DE3236097A1/de not_active Withdrawn
- 1982-09-29 BG BG059441A patent/BG40653A3/xx unknown
- 1982-09-29 BG BG058133A patent/BG40474A3/xx unknown
- 1982-09-29 RO RO82113505A patent/RO88971A/ro unknown
- 1982-09-29 CS CS826953A patent/CS235963B2/cs unknown
- 1982-09-29 NL NL8203767A patent/NL8203767A/nl not_active Application Discontinuation
-
1983
- 1983-09-15 SU SU833642746A patent/SU1272979A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| CS235963B2 (en) | 1985-05-15 |
| SU1416045A3 (ru) | 1988-08-07 |
| PL135607B1 (en) | 1985-11-30 |
| RO88971A (ro) | 1986-04-30 |
| PT75613B (en) | 1984-12-10 |
| NL8203767A (nl) | 1983-04-18 |
| AT381618B (de) | 1986-11-10 |
| CA1217766A (en) | 1987-02-10 |
| IT1210938B (it) | 1989-09-29 |
| IT8223463A0 (it) | 1982-09-28 |
| HU183589B (en) | 1984-05-28 |
| BE894492A (fr) | 1983-03-28 |
| DK430682A (da) | 1983-03-30 |
| DD204608A5 (de) | 1983-12-07 |
| GB2106518A (en) | 1983-04-13 |
| PT75613A (en) | 1982-10-01 |
| ATA352182A (de) | 1986-04-15 |
| DE3236097A1 (de) | 1983-04-14 |
| GR77658B (cs) | 1984-09-25 |
| GB2106518B (en) | 1985-07-17 |
| FR2513485B1 (fr) | 1988-09-16 |
| FR2513485A1 (fr) | 1983-04-01 |
| PL238404A1 (en) | 1983-04-25 |
| TR21704A (tr) | 1985-03-18 |
| BG40474A3 (en) | 1986-12-15 |
| CH655305A5 (de) | 1986-04-15 |
| US4559083A (en) | 1985-12-17 |
| BG40653A3 (en) | 1986-01-15 |
| SU1272979A3 (ru) | 1986-11-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2433067C3 (cs) | ||
| CH621921A5 (cs) | ||
| EP0003805B1 (de) | Pyridazonverbindungen und diese enthaltende herbizide Zusammensetzungen | |
| DD157754A5 (de) | Herbizide zusammensetzungen | |
| DE2804664A1 (de) | N- eckige klammer auf (phosphinyl) amino eckige klammer zu thio-methylcarbamate bzw. n- eckige klammer auf (phosphinothioyl) amino eckige klammer zu thio-methylcarbamate, deren verwendung in einem verfahren zur schaedlingsbekaempfung, pestizide mittel welche diese verbindungen enthalten, sowie verfahren zur herstellung dieser verbindungen und dafuer benoetigte ausgangsmaterialien | |
| DE2101938C2 (de) | 3-[2-Chlor-4-(3,3-dimethylureido)-phenyl]-5-tert.-butyl-1,3,4-oxadiazolon-(2), seine Herstellung und herbicide Zusammensetzungen, die es enthalten | |
| DD210260A5 (de) | Verfahren zur herstellung von carbonsaeureamido-thiolcarbamat-derivaten | |
| DE3533440A1 (de) | N-substituierte 3,4,5,6-tetrahydrophthalimide, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz | |
| DD202495A5 (de) | Herbizide zusammensetzung | |
| DE1618644B2 (de) | N-(Cyclohexen-l-yl)- a -chloracetamide, Verfahren zu ihrer Herstellung und sie enthaltende Herbicide | |
| CH643537A5 (de) | 2-(propargyloxyimino)-1,7,7-trimethyl-bicyclo(2.2.1)heptan. | |
| EP0058639B1 (de) | 2-(4-(6-Halogen-chinoxalinyl-2-oxy)-phenoxy)-propionsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide und Pflanzenwuchsregulatoren | |
| DE1618968C2 (cs) | ||
| DE3238958A1 (de) | Phosphorhaltige funktionelle essigsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende heribizide und wachstumsregulierende mittel | |
| DE1116469B (de) | Selektive herbicide Mittel | |
| EP0075249B1 (de) | Herbizide Mittel | |
| DE1567010C3 (de) | Herbicides Mittel mit einem Gehalt an N-Aryl-Harnstoff-Derivaten | |
| DD236868A5 (de) | Mittel zum protahieren der wirkungsdauer und zur erhoehung der selektivitaet von herbiziden zusammensetzungen | |
| DE2902099C2 (de) | Unkrautvertilgungsmittel für Getreide auf Basis von Thiolcarbamat-Triazin-Gemischen | |
| DE4011781A1 (de) | Herbizides mittel | |
| DE3502629A1 (de) | Phenoxybenzoesaeurederivate, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz | |
| DE2229211A1 (de) | N-Acetonitrilo-alpha-phenoxyalkylamide und ihre Verwendung als Herbizide | |
| DE3807532A1 (de) | Pyrimidin-carbonsaeuren, verfahren zur herstellung und ihre verwendung als herbizide | |
| DE3014922C2 (de) | N-Alkoxymethyl-chloracetanilide und diese enthaltende herbizide Mittel | |
| AT368681B (de) | Herbizide zusammensetzungen |