SE443559B - Plantillvextmodifierande 4-alkyltio-2-trifluormetylalkansulfonanilider och derivat derav samt anvendning av dessa - Google Patents
Plantillvextmodifierande 4-alkyltio-2-trifluormetylalkansulfonanilider och derivat derav samt anvendning av dessaInfo
- Publication number
- SE443559B SE443559B SE7803934A SE7803934A SE443559B SE 443559 B SE443559 B SE 443559B SE 7803934 A SE7803934 A SE 7803934A SE 7803934 A SE7803934 A SE 7803934A SE 443559 B SE443559 B SE 443559B
- Authority
- SE
- Sweden
- Prior art keywords
- compound
- grass
- control
- compounds
- plant growth
- Prior art date
Links
- 230000008635 plant growth Effects 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 89
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 150000003931 anilides Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003607 modifier Substances 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 238000000034 method Methods 0.000 description 37
- 239000000243 solution Substances 0.000 description 29
- 239000000047 product Substances 0.000 description 25
- 244000025254 Cannabis sativa Species 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 229920000742 Cotton Polymers 0.000 description 18
- 241000219146 Gossypium Species 0.000 description 18
- 244000061176 Nicotiana tabacum Species 0.000 description 18
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 18
- 240000002439 Sorghum halepense Species 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 230000002363 herbicidal effect Effects 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 230000012010 growth Effects 0.000 description 16
- 239000004009 herbicide Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 244000068988 Glycine max Species 0.000 description 13
- 235000010469 Glycine max Nutrition 0.000 description 13
- 240000008042 Zea mays Species 0.000 description 13
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 13
- -1 amine salts Chemical class 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 230000009467 reduction Effects 0.000 description 12
- 244000075850 Avena orientalis Species 0.000 description 11
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 11
- 244000062793 Sorghum vulgare Species 0.000 description 11
- 235000021536 Sugar beet Nutrition 0.000 description 11
- 230000009036 growth inhibition Effects 0.000 description 11
- 235000007320 Avena fatua Nutrition 0.000 description 10
- 241000287828 Gallus gallus Species 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 10
- 239000005648 plant growth regulator Substances 0.000 description 10
- 230000006378 damage Effects 0.000 description 9
- 235000013399 edible fruits Nutrition 0.000 description 9
- 238000007429 general method Methods 0.000 description 9
- 235000019713 millet Nutrition 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CFPIGEXZPWTNOR-UHFFFAOYSA-N 4-chloro-1-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C(F)(F)F CFPIGEXZPWTNOR-UHFFFAOYSA-N 0.000 description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 8
- AVAVGEJYYHSTIT-UHFFFAOYSA-N [4-amino-3-(trifluoromethyl)phenyl] thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1C(F)(F)F AVAVGEJYYHSTIT-UHFFFAOYSA-N 0.000 description 8
- 235000020971 citrus fruits Nutrition 0.000 description 8
- 235000005822 corn Nutrition 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 238000003306 harvesting Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 231100000674 Phytotoxicity Toxicity 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 5
- 241000207199 Citrus Species 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 235000015278 beef Nutrition 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 235000015205 orange juice Nutrition 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DQFIISLTSIXBKG-UHFFFAOYSA-N 4-ethylsulfanyl-1-nitro-2-(trifluoromethyl)benzene Chemical compound CCSC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 DQFIISLTSIXBKG-UHFFFAOYSA-N 0.000 description 3
- ZMHBBQHIIBIBHS-UHFFFAOYSA-N 4-methylsulfanyl-2-(trifluoromethyl)aniline Chemical compound CSC1=CC=C(N)C(C(F)(F)F)=C1 ZMHBBQHIIBIBHS-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 3
- MTEUDTXTXOJDST-UHFFFAOYSA-N 4-ethylsulfanyl-2-(trifluoromethyl)aniline Chemical compound CCSC1=CC=C(N)C(C(F)(F)F)=C1 MTEUDTXTXOJDST-UHFFFAOYSA-N 0.000 description 2
- QMXDETIJEJDPGG-UHFFFAOYSA-N 4-propan-2-ylsulfanyl-2-(trifluoromethyl)aniline Chemical compound CC(C)SC1=CC=C(N)C(C(F)(F)F)=C1 QMXDETIJEJDPGG-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 244000075634 Cyperus rotundus Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 235000002357 Ribes grossularia Nutrition 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- 235000005010 Scirpus paludosus Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000005341 cation exchange Methods 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 238000009371 citriculture Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000003630 growth substance Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 230000009526 moderate injury Effects 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 235000015927 pasta Nutrition 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- LWHIUKIAXXDRCU-UHFFFAOYSA-N 1-nitro-4-propan-2-ylsulfanyl-2-(trifluoromethyl)benzene Chemical compound CC(C)SC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 LWHIUKIAXXDRCU-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- IQIBYAHJXQVQGB-UHFFFAOYSA-N 2-methylbutane-2-thiol Chemical compound CCC(C)(C)S IQIBYAHJXQVQGB-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- HXGNVPCNSPKDRK-UHFFFAOYSA-N 4-methylsulfanyl-n-phenyl-2-(trifluoromethyl)butane-1-sulfonamide Chemical compound CSCCC(C(F)(F)F)CS(=O)(=O)NC1=CC=CC=C1 HXGNVPCNSPKDRK-UHFFFAOYSA-N 0.000 description 1
- VUDGQQXDFUOLQF-UHFFFAOYSA-N 4-methylsulfonyl-n-phenyl-2-(trifluoromethyl)butane-1-sulfonamide Chemical compound CS(=O)(=O)CCC(C(F)(F)F)CS(=O)(=O)NC1=CC=CC=C1 VUDGQQXDFUOLQF-UHFFFAOYSA-N 0.000 description 1
- LNJTWAFOMNBPEN-UHFFFAOYSA-N 4-propylsulfanyl-2-(trifluoromethyl)aniline Chemical compound CCCSC1=CC=C(N)C(C(F)(F)F)=C1 LNJTWAFOMNBPEN-UHFFFAOYSA-N 0.000 description 1
- ARCFRGRWHCYXSC-UHFFFAOYSA-N 4-tert-butylsulfanyl-1-nitro-2-(trifluoromethyl)benzene Chemical compound CC(C)(C)SC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 ARCFRGRWHCYXSC-UHFFFAOYSA-N 0.000 description 1
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 241000202844 Eriophorum Species 0.000 description 1
- 241001091440 Grossulariaceae Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001490213 Milium Species 0.000 description 1
- 235000005052 Milium effusum Nutrition 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 244000171263 Ribes grossularia Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical class 0.000 description 1
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical class [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 230000005200 bud stage Effects 0.000 description 1
- 230000028446 budding cell bud growth Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- UWRBYRMOUPAKLM-UHFFFAOYSA-L lead arsenate Chemical compound [Pb+2].O[As]([O-])([O-])=O UWRBYRMOUPAKLM-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- GXPGKOGAGPTQOO-UHFFFAOYSA-N n-[2-(trifluoromethyl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1C(F)(F)F GXPGKOGAGPTQOO-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 231100000817 safety factor Toxicity 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000001629 suppression Effects 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78622277A | 1977-04-11 | 1977-04-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7803934L SE7803934L (sv) | 1978-10-12 |
| SE443559B true SE443559B (sv) | 1986-03-03 |
Family
ID=25137949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7803934A SE443559B (sv) | 1977-04-11 | 1978-04-07 | Plantillvextmodifierande 4-alkyltio-2-trifluormetylalkansulfonanilider och derivat derav samt anvendning av dessa |
Country Status (20)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1113963A (en) * | 1978-04-06 | 1981-12-08 | Thomas J. Walter | Process for preparing aniline compounds |
| DE2845996A1 (de) * | 1978-10-23 | 1980-04-30 | Bayer Ag | Herbizide mittel, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von unkraeutern |
| DE2845997A1 (de) * | 1978-10-23 | 1980-04-30 | Bayer Ag | Pflanzenwachstumsregulierende mittel, verfahren zu ihrer herstellung und ihre verwendung zur regulierung des pflanzenwachstums |
| DE3002895A1 (de) * | 1979-01-29 | 1980-08-07 | Minnesota Mining & Mfg | N-substituierte alkansulfonanilide |
| US4913728A (en) * | 1979-01-29 | 1990-04-03 | Minnesota Mining And Manufacturing Company | Substituted-4-alkylthioalkane-sulfonanilides and operatives |
| ZA80273B (en) * | 1979-01-29 | 1981-03-25 | Minnesota Mining & Mfg | 4-phenylthioalkanesulfonanilides and derivatives thereof |
| ZA80274B (en) * | 1979-01-29 | 1981-03-25 | Minnesota Mining & Mfg | Substituted-4-alkylthioalkane-sulfonanilides and derivatives thereof |
| US5304554A (en) * | 1990-04-27 | 1994-04-19 | Emory University | 4-[(alkyl or dialkyl)amino]quinolines and their method of preparation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3996277A (en) * | 1974-11-14 | 1976-12-07 | Minnesota Mining And Manufacturing Company | 4-Methylthio-2-trifluoromethylmethanesulfonanilide and derivatives thereof |
-
1978
- 1978-03-15 CA CA298,941A patent/CA1091695A/en not_active Expired
- 1978-03-20 ZA ZA00781598A patent/ZA781598B/xx unknown
- 1978-04-05 PH PH20980A patent/PH18632A/en unknown
- 1978-04-07 NL NL7803725A patent/NL7803725A/xx not_active Application Discontinuation
- 1978-04-07 SE SE7803934A patent/SE443559B/sv not_active IP Right Cessation
- 1978-04-08 ES ES468658A patent/ES468658A1/es not_active Expired
- 1978-04-10 IN IN389/CAL/78A patent/IN148266B/en unknown
- 1978-04-10 JP JP4203578A patent/JPS53127435A/ja active Pending
- 1978-04-10 IT IT48824/78A patent/IT1102577B/it active
- 1978-04-10 DE DE19782815340 patent/DE2815340A1/de active Granted
- 1978-04-10 IL IL54473A patent/IL54473A/xx unknown
- 1978-04-10 BR BR7802212A patent/BR7802212A/pt unknown
- 1978-04-10 AU AU34924/78A patent/AU516708B2/en not_active Expired
- 1978-04-10 BE BE186686A patent/BE865843A/xx not_active IP Right Cessation
- 1978-04-10 FR FR7810584A patent/FR2387215A1/fr active Granted
- 1978-04-10 CH CH384178A patent/CH631965A5/de not_active IP Right Cessation
- 1978-04-10 GB GB14016/78A patent/GB1580880A/en not_active Expired
- 1978-04-10 MX MX787009U patent/MX5351E/es unknown
- 1978-04-10 NZ NZ186918A patent/NZ186918A/xx unknown
- 1978-04-19 AR AR271729A patent/AR218660A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2387215A1 (fr) | 1978-11-10 |
| SE7803934L (sv) | 1978-10-12 |
| IN148266B (enrdf_load_stackoverflow) | 1980-12-27 |
| ES468658A1 (es) | 1979-09-16 |
| AU516708B2 (en) | 1981-06-18 |
| ZA781598B (en) | 1979-06-27 |
| IL54473A (en) | 1982-01-31 |
| JPS53127435A (en) | 1978-11-07 |
| MX5351E (es) | 1983-06-28 |
| DE2815340C2 (enrdf_load_stackoverflow) | 1988-06-16 |
| BE865843A (fr) | 1978-10-10 |
| CH631965A5 (en) | 1982-09-15 |
| IT1102577B (it) | 1985-10-07 |
| BR7802212A (pt) | 1978-12-19 |
| NZ186918A (en) | 1980-11-14 |
| IT7848824A0 (it) | 1978-04-10 |
| PH18632A (en) | 1985-08-23 |
| FR2387215B1 (enrdf_load_stackoverflow) | 1984-06-01 |
| AR218660A1 (es) | 1980-06-30 |
| NL7803725A (nl) | 1978-10-13 |
| AU3492478A (en) | 1979-10-18 |
| DE2815340A1 (de) | 1978-10-12 |
| CA1091695A (en) | 1980-12-16 |
| IL54473A0 (en) | 1978-07-31 |
| GB1580880A (en) | 1980-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1082205A (en) | Miticidal and aphicidal 2-higher alkyl-3-hydroxy-1,4- naphthaquinone carboxylic acid esters | |
| BG60283B2 (bg) | Средство за имунизиране на растения срещу фитопатогенни микроорганизми | |
| EP0054431A1 (en) | Optical isomer of a triazolylpentenol, and its production and use as fungicide | |
| DE3415820A1 (de) | 1-carbalkoxyalkyl-3-aryloxy-4-(2'-carboxyphenyl)-azet-2-one, diese enthaltende pflanzenwachstumsregulierende mittel und verfahren zum regulieren des pflanzenwachstums | |
| SU1428196A3 (ru) | Способ получени 2-замещенных фенил-4,5,6,7-тетрагидро-2Н-изоиндол-1,3-дионов | |
| US3957852A (en) | Diphenyl ether compounds | |
| SE443559B (sv) | Plantillvextmodifierande 4-alkyltio-2-trifluormetylalkansulfonanilider och derivat derav samt anvendning av dessa | |
| DE2802496A1 (de) | Triazol- und imidazolverbindungen und ihre anwendung als fungizide und pflanzenwachstumsregulatoren | |
| US4556411A (en) | Benzothiazole derivatives for plant growth and development modification | |
| US4623379A (en) | Plant growth and development modification using 2-(2-oxycarbonylphenyl)benzimidazole derivatives | |
| SE449817B (sv) | Medel med gametocid verkan innehallande som aktiv komponent minst ett nitroaryl-alkyl-sulfon-derivat samt anvendning derav | |
| JPS62132804A (ja) | 植物生長調節剤 | |
| US4659360A (en) | Plant growth and development modification using benzoxazole derivatives | |
| US3427146A (en) | Phenoxypyridazines as herbicides | |
| US3932458A (en) | Antimicrobial and plant-active 4,5-dihalopyrrole-2-carbonitriles | |
| US4751226A (en) | Pyrazoloisoquinoline derivatives, plant growth regulating compositions, and method of use therefor | |
| US4341901A (en) | 4-Alkylthio-2-trifluoromethylalkanesulfonanilides and derivatives thereof | |
| US3985539A (en) | 4,5-Dihalopyrrole-2-carbonitrile-containing terrestrial and aquatic hebicidal composition | |
| US4340765A (en) | 4-Phenoxy-2-butene derivatives as plant growth regulators | |
| EP0003881A1 (en) | Substituted phenylnitramines, their preparation and their application as fungicidal agents | |
| US5009702A (en) | Cyclohexenone compounds and use as herbicides or as plant growth regulators | |
| JP2522807B2 (ja) | シクロヘキセノン誘導体及び該化合物を含有する植物生長調整剤 | |
| EP0249858B1 (de) | Fluoralkylsubstituierte Chinolinderivate. ihre Herstellung sowie Verwendung zur Bekämpfung unerwünschten Pflanzenwachstums | |
| US3966817A (en) | Herbicidal ortho-nitroanilines | |
| BR102023008825A2 (pt) | Processo de preparo de compostos derivados da 3r,4s,5r,6stetraidro-3,6-epoxiisobenzofuran-7,8-diona, composto obtido, composições e usos |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
Ref document number: 7803934-4 Effective date: 19900411 Format of ref document f/p: F |