HU183589B - Herbicide composition containing carboxylic acid-amido-thiol-carbamate derivatives and process for preparing the active substances - Google Patents
Herbicide composition containing carboxylic acid-amido-thiol-carbamate derivatives and process for preparing the active substances Download PDFInfo
- Publication number
- HU183589B HU183589B HU812794A HU279481A HU183589B HU 183589 B HU183589 B HU 183589B HU 812794 A HU812794 A HU 812794A HU 279481 A HU279481 A HU 279481A HU 183589 B HU183589 B HU 183589B
- Authority
- HU
- Hungary
- Prior art keywords
- phenyl
- ethyl
- propyl
- butyl
- formula
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 46
- 230000002363 herbicidal effect Effects 0.000 title claims description 7
- 239000004009 herbicide Substances 0.000 title description 6
- 239000013543 active substance Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 alkyl radical Chemical class 0.000 claims abstract description 182
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 71
- 239000001257 hydrogen Substances 0.000 claims abstract description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 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 description 7
- 238000000034 method Methods 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 71
- 239000004480 active ingredient Substances 0.000 claims description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 239000000080 wetting agent Substances 0.000 claims description 7
- 239000003921 oil Substances 0.000 claims description 6
- 239000002270 dispersing agent Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000009736 wetting Methods 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 0.000 claims 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 2
- 125000000129 anionic group Chemical group 0.000 claims 2
- 239000003945 anionic surfactant Substances 0.000 claims 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- 150000008282 halocarbons Chemical class 0.000 claims 2
- 229910052604 silicate mineral Inorganic materials 0.000 claims 2
- 229910052600 sulfate mineral Inorganic materials 0.000 claims 2
- 229940088623 biologically active substance Drugs 0.000 claims 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 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 claims 1
- 239000002253 acid Substances 0.000 abstract description 5
- 239000011230 binding agent Substances 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 33
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 33
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 23
- 240000008042 Zea mays Species 0.000 description 23
- 239000004563 wettable powder Substances 0.000 description 22
- 238000002474 experimental method Methods 0.000 description 18
- 241000208818 Helianthus Species 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 235000003222 Helianthus annuus Nutrition 0.000 description 15
- 238000011282 treatment Methods 0.000 description 15
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 14
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 13
- 238000009472 formulation Methods 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000003944 tolyl group Chemical group 0.000 description 11
- 240000003768 Solanum lycopersicum Species 0.000 description 10
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
- 235000005822 corn Nutrition 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 235000007244 Zea mays Nutrition 0.000 description 8
- 235000013339 cereals Nutrition 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 235000005775 Setaria Nutrition 0.000 description 7
- 241000232088 Setaria <nematode> Species 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 235000002634 Solanum Nutrition 0.000 description 6
- 241000207763 Solanum Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 244000062793 Sorghum vulgare Species 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- 239000000729 antidote Substances 0.000 description 5
- 239000011324 bead Substances 0.000 description 5
- 244000038559 crop plants Species 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229940075522 antidotes Drugs 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 240000001980 Cucurbita pepo Species 0.000 description 3
- 240000004585 Dactylis glomerata Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 240000006240 Linum usitatissimum Species 0.000 description 3
- 235000004431 Linum usitatissimum Nutrition 0.000 description 3
- 240000004713 Pisum sativum Species 0.000 description 3
- 235000010582 Pisum sativum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 230000004936 stimulating effect Effects 0.000 description 3
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 2
- 235000000832 Ayote Nutrition 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- 244000025254 Cannabis sativa 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
- 244000020551 Helianthus annuus Species 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 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
- 235000021307 Triticum 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
- SMLHHBQGIJMAIM-UHFFFAOYSA-N calcium;2-dodecylbenzenesulfonic acid Chemical compound [Ca].CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O SMLHHBQGIJMAIM-UHFFFAOYSA-N 0.000 description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 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
- XFWGIHYNONVQLY-UHFFFAOYSA-N dichloromethane;phenol Chemical compound ClCCl.OC1=CC=CC=C1 XFWGIHYNONVQLY-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
- 241001233957 eudicotyledons Species 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003864 humus Substances 0.000 description 2
- 230000002262 irrigation Effects 0.000 description 2
- 238000003973 irrigation Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 235000015136 pumpkin Nutrition 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 235000021533 Beta vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 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
- 241000919496 Erysimum Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 244000197960 Galium verum Species 0.000 description 1
- 235000000911 Galium verum Nutrition 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 101001018064 Homo sapiens Lysosomal-trafficking regulator Proteins 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 102100033472 Lysosomal-trafficking regulator Human genes 0.000 description 1
- 244000038561 Modiola caroliniana Species 0.000 description 1
- 235000010703 Modiola caroliniana Nutrition 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 244000286177 Raphanus raphanistrum Species 0.000 description 1
- 235000000241 Raphanus raphanistrum Nutrition 0.000 description 1
- 235000002560 Solanum lycopersicum Nutrition 0.000 description 1
- 235000007230 Sorghum bicolor Nutrition 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- CPGKMLVTFNUAHL-UHFFFAOYSA-N [Ca].[Ca] Chemical compound [Ca].[Ca] CPGKMLVTFNUAHL-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 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
- 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
- JYRFCKZKWGDLQX-UHFFFAOYSA-N carbonochloridic acid;ethanethiol Chemical compound CCS.OC(Cl)=O JYRFCKZKWGDLQX-UHFFFAOYSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- QRYFGTULTGLGHU-NBERXCRTSA-N iturelix Chemical compound C([C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CCCCNC(=O)C=1C=NC=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)CCCNC(=O)C1=CC=CN=C1 QRYFGTULTGLGHU-NBERXCRTSA-N 0.000 description 1
- 108010083551 iturelix Proteins 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- RSQPZJUMXVEWBR-UHFFFAOYSA-N n-(2-ethylphenyl)propanamide Chemical compound CCC(=O)NC1=CC=CC=C1CC RSQPZJUMXVEWBR-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- PDIJHSBTQCAHPI-UHFFFAOYSA-N octyl N-thiophen-2-ylcarbamate Chemical compound CCCCCCCCOC(=O)NC1=CC=CS1 PDIJHSBTQCAHPI-UHFFFAOYSA-N 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 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
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 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)
Priority Applications (25)
| 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 |
| AT0352182A AT381618B (de) | 1981-09-29 | 1982-09-22 | Neue carbonsaeure-amido-thiolcarbamat-derivate enthaltendes unkrautbekaempfungsmittel |
| US06/421,238 US4559083A (en) | 1981-09-29 | 1982-09-22 | Herbicide composition containing carboxylic-acid-amidothiolcarbamate derivatives |
| TR21704A TR21704A (tr) | 1981-09-29 | 1982-09-24 | Karbonik asit amidotiolkarbamat tuerevlerini havi olan zararh otlarla muecadele maddeleri ve etkili bilesikleri imale mahsus usul |
| 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 |
| BE1/10596A BE894492A (fr) | 1981-09-29 | 1982-09-27 | Herbicides contenant des derives de carboxamidothiocarbamates et procede pour la preparation des constituants actifs de ces herbicides |
| CA000412374A CA1217766A (en) | 1981-09-29 | 1982-09-28 | Herbicide composition containing carboxilic-acid- amido-thiolcarbamate derivatives and a process for the preparation of the agents |
| IT8223463A IT1210938B (it) | 1981-09-29 | 1982-09-28 | Diserbante contenente derivati di ammido-tiolcarbammati di acidi carbonici e procedimento per lapreparazione delle sostanze attive. |
| PT75613A PT75613B (en) | 1981-09-29 | 1982-09-28 | Process for the preparation of carboxamid-thiol-carbamate deri-vatives and herbicide compositions thereof |
| GR69384A GR77658B (en:Method) | 1981-09-29 | 1982-09-28 | |
| FR8216274A FR2513485B1 (fr) | 1981-09-29 | 1982-09-28 | Herbicides contenant des derives carboxamido-thiocarbamates et procede pour la preparation des constituants actifs de ces herbicides |
| SU823494193A SU1416045A3 (ru) | 1981-09-29 | 1982-09-28 | Гербицидна композици |
| DK430682A DK430682A (da) | 1981-09-29 | 1982-09-28 | Thiolcarbamatholdigt herbicid |
| PL1982238404A PL135607B1 (en) | 1981-09-29 | 1982-09-28 | Herbicide and method of obtaining novel derivatives of carbonamido-thiocarbaminate |
| GB08227657A GB2106518B (en) | 1981-09-29 | 1982-09-28 | Herbicide composition containing novel carboxylic-acid-amido-thiolcarbamate derivatives |
| CH5695/82A CH655305A5 (de) | 1981-09-29 | 1982-09-28 | Carbonsaeure-amido-thiolcarbamat-derivate, verfahren zu deren herstellung und diese enthaltende unkrautbekaempfungsmittel. |
| NL8203767A NL8203767A (nl) | 1981-09-29 | 1982-09-29 | Carbonzuuramidothiolcarbamaatderivaten bevattend onkruidbestrijdingsmiddel en werkwijze voor de bereiding van de actieve stoffen. |
| BG058133A BG40474A3 (en) | 1981-09-29 | 1982-09-29 | Herbicide means |
| BG059441A BG40653A3 (en) | 1981-09-29 | 1982-09-29 | Method for preparing amidothiocarbamate derivatives of carbon acid |
| CS826953A CS235963B2 (en) | 1981-09-29 | 1982-09-29 | Herbicide agent and method of its effective substance production |
| DE19823236097 DE3236097A1 (de) | 1981-09-29 | 1982-09-29 | Thiocarbaminsaeure-s-ester-n-carbonsaeureamide, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel zur unkrautbekaempfung und/oder anregung des wachstumes von kulturpflanzen |
| RO82113505A RO88971A (ro) | 1981-09-29 | 1982-09-29 | Compozitie erbicida solida |
| SU833642746A SU1272979A3 (ru) | 1981-09-29 | 1983-09-15 | Способ получени эфиров ди- @ -замещенных тиокарбаминовых кислот |
| AT0229985A AT382614B (de) | 1981-09-29 | 1985-08-05 | Verfahren zur herstellung neuer carbonsaeure-amido-thiolcarbamat-derivate |
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 |
|---|---|
| HU183589B true HU183589B (en) | 1984-05-28 |
Family
ID=10961120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4559083A (en:Method) |
| AT (1) | AT381618B (en:Method) |
| BE (1) | BE894492A (en:Method) |
| BG (2) | BG40653A3 (en:Method) |
| CA (1) | CA1217766A (en:Method) |
| CH (1) | CH655305A5 (en:Method) |
| CS (1) | CS235963B2 (en:Method) |
| DD (2) | DD210260A5 (en:Method) |
| DE (1) | DE3236097A1 (en:Method) |
| DK (1) | DK430682A (en:Method) |
| FR (1) | FR2513485B1 (en:Method) |
| GB (1) | GB2106518B (en:Method) |
| GR (1) | GR77658B (en:Method) |
| HU (1) | HU183589B (en:Method) |
| IT (1) | IT1210938B (en:Method) |
| NL (1) | NL8203767A (en:Method) |
| PL (1) | PL135607B1 (en:Method) |
| PT (1) | PT75613B (en:Method) |
| RO (1) | RO88971A (en:Method) |
| SU (2) | SU1416045A3 (en:Method) |
| TR (1) | TR21704A (en:Method) |
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 |
| 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 (en:Method) | 1984-09-25 |
| GB2106518B (en) | 1985-07-17 |
| FR2513485B1 (fr) | 1988-09-16 |
| FR2513485A1 (fr) | 1983-04-01 |
| DD210260A5 (de) | 1984-06-06 |
| 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 |
|---|---|---|
| HU190898B (en) | Compositions containing 8-oxy-quikoline derivatives as antidotes further process for preparing 8-oxy-quinoline derivatives | |
| HU199247B (en) | Herbicides containing derivatives of 1-aril-4-subsituated-1,4-dihydro-5h-tetrasole-5-on or 5-tion and process for production of these derivatives | |
| US4435202A (en) | Plant growth regulator | |
| HU180702B (en) | Herbicide compositions containing phenoxy-alpha-phenoxy-alkane-carboxylic acid derivatives,and process for producing the active agents | |
| US4511581A (en) | Fungicidal indanylbenzamide | |
| HU183589B (en) | Herbicide composition containing carboxylic acid-amido-thiol-carbamate derivatives and process for preparing the active substances | |
| HU180955B (en) | Herbicide composition and process for producing new n-phenyl-n-comma aaove-methyl-urea derivatives as active agents | |
| JPH02279679A (ja) | 〔〔（１，３，５―トリアジン―２―イル）アミノカルボニル〕アミノスルホニル〕安息香酸エステル及びこれを含有する除草剤 | |
| EA000109B1 (ru) | Производные триазина | |
| CA1236832A (en) | N- and optionally n'-substituted (n-dichloroacetyl) glycine amides with an antidote action | |
| JPS5835987B2 (ja) | フエニル尿素誘導体、その製法及び同化合物を含有する選択的除草剤 | |
| JPS60166668A (ja) | ２−アルコキシアミノスルホニルベンゼン−スルホニルウレア誘導体、その製法及び除草剤 | |
| HU193422B (en) | Fungicide compositions containing benzyl-oycloalkenyl-urea-derivatives as active, agents and process for producing the active agents | |
| DE1291733B (de) | Verfahren zur Herstellung von N-Aryl-harnstoffen | |
| DE3320899C2 (de) | Carbamatderivate, Verfahren zu ihrer Herstellung und sie enthaltende Herbizide | |
| HU199252B (en) | Antidotum, antidotated herbicid and process for production of the antidotum | |
| JPH0352873A (ja) | ２―オキシベンジルアルコール誘導体および除草剤 | |
| JPS6116246B2 (en:Method) | ||
| HU198829B (en) | Herbicides with extended soil life and containing thiocarbamate derivatives as active ingredient | |
| KR100419853B1 (ko) | 제초활성을 가지는 광활성 (ｒ)-페녹시프로피온산-ｎ-메틸-ｎ-2-플루오로페닐아미드 화합물 | |
| KR920002793B1 (ko) | 벤질우레아 유도체의 제조방법 | |
| US3594405A (en) | Substituted pyranyl anilines as plant growth modifiers | |
| HU177551B (en) | Sulfurian herbicides containing diurethane derivatives | |
| JPS58183688A (ja) | オキサジアゾ−ル誘導体、その製法及び除草剤 | |
| CA1204768A (en) | N-(benzamidosulfenyl)-n-methylcarbamates, process for their manufacture and their use in pest control |