WO1991007381A1 - Carbamoyl derivatives of alkanolamines and antistress-type means for plant growth regulation based thereon - Google Patents
Carbamoyl derivatives of alkanolamines and antistress-type means for plant growth regulation based thereon Download PDFInfo
- Publication number
- WO1991007381A1 WO1991007381A1 PCT/SU1989/000283 SU8900283W WO9107381A1 WO 1991007381 A1 WO1991007381 A1 WO 1991007381A1 SU 8900283 W SU8900283 W SU 8900283W WO 9107381 A1 WO9107381 A1 WO 9107381A1
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- Prior art keywords
- found
- calculated
- acid
- methyl
- ethanolamine
- Prior art date
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- 230000008635 plant growth Effects 0.000 title claims abstract description 8
- 230000033228 biological regulation Effects 0.000 title abstract description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 title abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 230000000694 effects Effects 0.000 claims description 22
- QENMPTUFXWVPQZ-UHFFFAOYSA-N (2-hydroxyethylazaniumyl)formate Chemical compound OCCNC(O)=O QENMPTUFXWVPQZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 125000005498 phthalate group Chemical class 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- -1 chlorophenyl-sulphonyl Chemical group 0.000 abstract description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 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 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 62
- 239000002253 acid Substances 0.000 description 35
- 150000001875 compounds Chemical class 0.000 description 34
- 229940031098 ethanolamine Drugs 0.000 description 28
- 241000196324 Embryophyta Species 0.000 description 18
- 239000002699 waste material Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 230000012010 growth Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 238000012545 processing Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 8
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 241000209219 Hordeum Species 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- OUWUZJDWCPZADV-UHFFFAOYSA-L (3-chlorophenyl) phosphate Chemical compound [O-]P([O-])(=O)OC1=CC=CC(Cl)=C1 OUWUZJDWCPZADV-UHFFFAOYSA-L 0.000 description 1
- PMUNIMVZCACZBB-UHFFFAOYSA-N 2-hydroxyethylazanium;chloride Chemical compound Cl.NCCO PMUNIMVZCACZBB-UHFFFAOYSA-N 0.000 description 1
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-M 3-methylphenolate Chemical compound CC1=CC=CC([O-])=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-M 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- LGAQJENWWYGFSN-UHFFFAOYSA-N 4-methylpent-2-ene Chemical group CC=CC(C)C LGAQJENWWYGFSN-UHFFFAOYSA-N 0.000 description 1
- FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical compound C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 241000282421 Canidae Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002180 anti-stress Effects 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
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- KVADBZXOFYIEPQ-UHFFFAOYSA-N ethyl(2-hydroxyethyl)carbamic acid Chemical compound CCN(C(O)=O)CCO KVADBZXOFYIEPQ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000005714 functional activity Effects 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AFSYRVDDZGJTIL-UHFFFAOYSA-N oxydibutanol Chemical compound CC(O)CCOCCC(C)O AFSYRVDDZGJTIL-UHFFFAOYSA-N 0.000 description 1
- MRLGBUWOAFGOBH-UHFFFAOYSA-N panamine Natural products C1C(C23)CCCN3C(N3)CCCC3C32CN2CCCCC2C1C3 MRLGBUWOAFGOBH-UHFFFAOYSA-N 0.000 description 1
- 235000015927 pasta Nutrition 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000004114 suspension culture Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic 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
- A01N47/12—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
- A01N47/20—N-Aryl derivatives thereof
-
- 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
-
- 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
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/48—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
Definitions
- Adverse weather conditions such as a barb or severe wounds, result in significant physical harm. This is due to the inability to process and to the disruption of the operating system - there are 15 incidents of physical damage to the system.
- ⁇ ⁇ -0 ⁇ or ⁇ ( ⁇ , ⁇ , 710545), may be taken 30 times as a result of increasing the incidence of agricultural injuries. - g. -
- the indicated connections have a disadvantage that is limited to their use: they are active due to the lack of growth; to obtain these compounds, they use comparatively other original products, such as m-nitrate and m-aminophenol; In the process of the preparation of the terminated compounds, unstable ones are observed and when the products are processed - arylhydroxylamines, increased - decreased
- the main task of the invention is to create new materials that have a high efficiency of regulation
- the claimed compounds possess a high activity of the growth of plants, and also have an anti-susceptibility, that is, an increase in susceptibility to susceptibility.
- Medicament for the regulation of the system of plant activity which contains the active substance and the solvent, which is the share of the consumables.
- the claimed invention is in accordance with the invention, and it is predominantly contained in the material of the following two-hydrous esters that have the following effects: n ⁇ ( ⁇ fensiv 2 ) 2 _- ⁇ - till - ⁇ debut-her ? -of
- the inventive devices are highly active and are used as a means of increasing the growth of assets and of the insensitiveness of the process to increase the resilience of
- the resulting compounds are resistant to 10 crystalline materials with low temperature or viscous oils.
- P-compound for example, the claimed compound of the 2-hydroxybetoxybamic acid (in dimethyl sulfoxide, c_ ⁇ , w.), (4);
- the method of obtaining the indicated compounds may also be impeded by the interaction of 35 - 5 - in the case of justification with the following extracting reaction mixture and isolation of the target product.
- the resulting compounds are resistant to crystalline substances or viscous oils.
- Spekt ⁇ (in dimethyl sulfoxide, a.-), for example, for the claimed compound - n - (isopropoxoxycarbonyl) - -0- (4-hydroxyphenylcarbamoyl) ethanolamine.
- Seeds are suitable for the processing of green seeds, using suitable methods for spraying, harvesting, soaking or pumping seeds. By the way, we declare the goods to provide for a favorable agricultural crop for 15-20. For better understanding,
- example 17 of the second category is 2-odd acid and 3-methyl acid - 20 - the schlizian receives ⁇ - (phenoxyphenyl) -0- (3-methylphenylcarbamoyl) ethanolamine, T.pl. 86-88 ° ⁇ , yield 72.5 $.
- the claimed compound is an ether of 2-hydroxyethylcarbamic acid 69, 0
- the claimed compound is an ester of 2-hydroxyethyl-carboxylic acid 49, 0
- the claimed compound is a 2-hydroxyethyl ester of a 2-hydroxyethylcarboxylic acid 41, 0
- the claimed compound is a Pentium 2-Hydroxyethylcarboxylic Acid 30, 0
- the protective effect of the claimed device is on the basis of ⁇ - (isopropoxypic) -0- (4-acid foule) of ethanolamine for the benefit of the synagogue.
- the declared actions of the device are on the basis of a connected and- (metroxibar) -0- (_ ⁇ -rank ⁇ flower ⁇ where° ⁇ than whyeverhashas admir ⁇ rion ⁇ rion)))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))))
- the Ylichivka cultivar was cultivated on the basis of the products of the reluctant crop, in addition to the concentration of activities
- the preparation is concentrate in the presence of an electric discharge (mg / l) ⁇ ⁇ online)
- the 10th stability margin was for acquisitions, which are able to give new sprouts and green leaves after being used, which is expressed in terms of profitability.
- the results are apparent in Table II. - 37 -
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)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19893991770 DE3991770T (enrdf_load_stackoverflow) | 1989-11-14 | 1989-11-14 | |
AU52673/90A AU625383B2 (en) | 1989-11-14 | 1989-11-14 | Carbamoyl derivatives of alkanolamines and antistress-type means for plant growth regulation based thereon |
PCT/SU1989/000283 WO1991007381A1 (en) | 1989-11-14 | 1989-11-14 | Carbamoyl derivatives of alkanolamines and antistress-type means for plant growth regulation based thereon |
GB9115597A GB2245566A (en) | 1989-11-14 | 1991-07-15 | Carbamoyl derivatives of alkanolamines and antistress-action agent for plant-growth regulation based thereon |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/SU1989/000283 WO1991007381A1 (en) | 1989-11-14 | 1989-11-14 | Carbamoyl derivatives of alkanolamines and antistress-type means for plant growth regulation based thereon |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1991007381A1 true WO1991007381A1 (en) | 1991-05-30 |
Family
ID=21617586
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/SU1989/000283 WO1991007381A1 (en) | 1989-11-14 | 1989-11-14 | Carbamoyl derivatives of alkanolamines and antistress-type means for plant growth regulation based thereon |
Country Status (4)
Country | Link |
---|---|
AU (1) | AU625383B2 (enrdf_load_stackoverflow) |
DE (1) | DE3991770T (enrdf_load_stackoverflow) |
GB (1) | GB2245566A (enrdf_load_stackoverflow) |
WO (1) | WO1991007381A1 (enrdf_load_stackoverflow) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001085675A3 (en) * | 2000-05-05 | 2002-05-02 | Univ Pittsburgh | Fluorous tagging compounds and their use |
EP1803453A1 (en) * | 2005-12-21 | 2007-07-04 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Carbamate antibiotics |
RU2651792C1 (ru) * | 2016-12-23 | 2018-04-24 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Российский химико-технологический университет имени Д.И. Менделеева" | Способ получения N-(2-гидроксиэтил)-О-изопропилкарбамата |
RU2711231C1 (ru) * | 2019-08-20 | 2020-01-15 | АО "Щелково Агрохим" | Способ получения регулятора роста растений N-(изопропоксикарбонил)-О-(4-хлорфенилкарбамоил)этаноламина |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2921955A (en) * | 1956-12-11 | 1960-01-19 | Texaco Inc | Carbonate derivatives of ethanolamines |
US2959611A (en) * | 1959-01-21 | 1960-11-08 | Du Pont | Fluoroalkyl chlorocarbonates and carbamates |
SU710545A1 (ru) * | 1978-08-07 | 1980-01-25 | Предприятие П/Я Р-6225 | Регул тор роста растений |
GB1572470A (en) * | 1976-02-09 | 1980-07-30 | Ciba Geigy Ag | Method of protecting plants against damage by frost |
SU801829A1 (ru) * | 1979-07-06 | 1981-02-07 | Всесоюзный Научно-Исследовательскийинститут Химических Средств Защитырастений | Регул тор роста растений с анти-СТРЕССОВыМ эффЕКТОМ |
DD241007A1 (de) * | 1985-09-17 | 1986-11-26 | Forschzent Bodenfruchtbarkeit | Mittel zur erhoehung der ertragswirksamen wasserausnutzung landwirtschaftlicher kulturpflanzen |
DD259123A1 (de) * | 1983-06-23 | 1988-08-17 | Michel Hans Juergen | Mittel zur erhoehung der toleranz von nutzpflanzen gegenueber stressbedingungen |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0257848A3 (en) * | 1986-08-14 | 1989-01-11 | King Industries, Inc. | Certain carbamates, processes for preparing same and use thereof |
DE3801082A1 (de) * | 1987-04-28 | 1988-11-17 | Bayer Ag | Mittel zur insekten- und milbenabwehr |
DE3804288A1 (de) * | 1987-06-03 | 1988-12-15 | Bayer Ag | Substituierte aminophenyl-carbamate |
-
1989
- 1989-11-14 WO PCT/SU1989/000283 patent/WO1991007381A1/ru active Application Filing
- 1989-11-14 DE DE19893991770 patent/DE3991770T/de not_active Withdrawn
- 1989-11-14 AU AU52673/90A patent/AU625383B2/en not_active Ceased
-
1991
- 1991-07-15 GB GB9115597A patent/GB2245566A/en not_active Withdrawn
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2921955A (en) * | 1956-12-11 | 1960-01-19 | Texaco Inc | Carbonate derivatives of ethanolamines |
US2959611A (en) * | 1959-01-21 | 1960-11-08 | Du Pont | Fluoroalkyl chlorocarbonates and carbamates |
GB1572470A (en) * | 1976-02-09 | 1980-07-30 | Ciba Geigy Ag | Method of protecting plants against damage by frost |
SU710545A1 (ru) * | 1978-08-07 | 1980-01-25 | Предприятие П/Я Р-6225 | Регул тор роста растений |
SU801829A1 (ru) * | 1979-07-06 | 1981-02-07 | Всесоюзный Научно-Исследовательскийинститут Химических Средств Защитырастений | Регул тор роста растений с анти-СТРЕССОВыМ эффЕКТОМ |
DD259123A1 (de) * | 1983-06-23 | 1988-08-17 | Michel Hans Juergen | Mittel zur erhoehung der toleranz von nutzpflanzen gegenueber stressbedingungen |
DD241007A1 (de) * | 1985-09-17 | 1986-11-26 | Forschzent Bodenfruchtbarkeit | Mittel zur erhoehung der ertragswirksamen wasserausnutzung landwirtschaftlicher kulturpflanzen |
Non-Patent Citations (1)
Title |
---|
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, T.78, N19, 1956, DOV BEN-ISHAI, "The Reactions of B-Hydroxyethylamides and B-Hydroxyethylcarbamates with Phosgene", pages 4962-4965. * |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001085675A3 (en) * | 2000-05-05 | 2002-05-02 | Univ Pittsburgh | Fluorous tagging compounds and their use |
US6825043B1 (en) | 2000-05-05 | 2004-11-30 | University Of Pittsburgh | Fluorous tagging compounds and methods of increasing the fluorous nature of compounds |
US7700794B2 (en) | 2000-05-05 | 2010-04-20 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Fluorous tagging compounds and methods of increasing the fluorous nature of compounds |
EP1803453A1 (en) * | 2005-12-21 | 2007-07-04 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Carbamate antibiotics |
JP2009520813A (ja) * | 2005-12-21 | 2009-05-28 | ネーデルランドセ オルガニサティエ フォール トエゲパストナトールヴェテンシャッペリク オンデルゾエク ティエヌオー | カルバメート系抗生物質 |
RU2651792C1 (ru) * | 2016-12-23 | 2018-04-24 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Российский химико-технологический университет имени Д.И. Менделеева" | Способ получения N-(2-гидроксиэтил)-О-изопропилкарбамата |
RU2711231C1 (ru) * | 2019-08-20 | 2020-01-15 | АО "Щелково Агрохим" | Способ получения регулятора роста растений N-(изопропоксикарбонил)-О-(4-хлорфенилкарбамоил)этаноламина |
Also Published As
Publication number | Publication date |
---|---|
GB9115597D0 (en) | 1991-09-18 |
AU5267390A (en) | 1991-06-13 |
GB2245566A (en) | 1992-01-08 |
DE3991770T (enrdf_load_stackoverflow) | 1992-01-30 |
AU625383B2 (en) | 1992-07-09 |
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