DE2214057A1 - N-arylcarbamidsaeureester, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren - Google Patents
N-arylcarbamidsaeureester, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatorenInfo
- Publication number
- DE2214057A1 DE2214057A1 DE19722214057 DE2214057A DE2214057A1 DE 2214057 A1 DE2214057 A1 DE 2214057A1 DE 19722214057 DE19722214057 DE 19722214057 DE 2214057 A DE2214057 A DE 2214057A DE 2214057 A1 DE2214057 A1 DE 2214057A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- acid esters
- aryl
- carbamic acid
- plant growth
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000005648 plant growth regulator Substances 0.000 title claims description 6
- -1 O-alkyl Chemical group 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 7
- 150000001768 cations Chemical class 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000005354 acylalkyl group Chemical group 0.000 claims abstract description 4
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 4
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- 230000008635 plant growth Effects 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- 150000003566 thiocarboxylic acids Chemical class 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000005131 dialkylammonium group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims 3
- 239000004606 Fillers/Extenders Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 5
- 101100125351 Candida albicans (strain SC5314 / ATCC MYA-2876) HYR4 gene Proteins 0.000 abstract 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 52
- 125000004432 carbon atom Chemical group C* 0.000 description 33
- 239000000460 chlorine Substances 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000004480 active ingredient Substances 0.000 description 27
- 238000009835 boiling Methods 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000009036 growth inhibition Effects 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 244000211187 Lepidium sativum Species 0.000 description 3
- 235000007849 Lepidium sativum Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- MDIATXVDRAKRQX-UHFFFAOYSA-N chloromethyl-(3-chlorophenyl)carbamic acid Chemical compound OC(=O)N(CCl)C1=CC=CC(Cl)=C1 MDIATXVDRAKRQX-UHFFFAOYSA-N 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000004883 flower formation Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005983 Maleic hydrazide Substances 0.000 description 2
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000003630 growth substance Substances 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000017066 negative regulation of growth Effects 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 229940035044 sorbitan monolaurate Drugs 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- GVIGIJWLQLXFLC-UHFFFAOYSA-N (3-chloro-n-propan-2-yloxycarbonylanilino)methyl acetate Chemical compound CC(C)OC(=O)N(COC(C)=O)C1=CC=CC(Cl)=C1 GVIGIJWLQLXFLC-UHFFFAOYSA-N 0.000 description 1
- SCTMVRVOGJDCRL-SQQVDAMQSA-N (e)-but-2-enoic acid;sodium Chemical compound [Na].C\C=C\C(O)=O SCTMVRVOGJDCRL-SQQVDAMQSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ULIKDJVNUXNQHS-UHFFFAOYSA-N 2-Propene-1-thiol Chemical compound SCC=C ULIKDJVNUXNQHS-UHFFFAOYSA-N 0.000 description 1
- LIJLYNWYKULUHA-UHFFFAOYSA-N 2-chloroethyl carbamate Chemical compound NC(=O)OCCCl LIJLYNWYKULUHA-UHFFFAOYSA-N 0.000 description 1
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- JKYWZTCKXGHPAY-UHFFFAOYSA-N COC(N(C(C=C1)=CC=C1Cl)OC(C=CC(Cl)=C1)=C1Cl)=O Chemical compound COC(N(C(C=C1)=CC=C1Cl)OC(C=CC(Cl)=C1)=C1Cl)=O JKYWZTCKXGHPAY-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 241000234645 Festuca pratensis Species 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- YGHIEEJZAFAFMP-UHFFFAOYSA-N propan-2-yl n-(3-chlorophenyl)-n-(propylsulfanylmethyl)carbamate Chemical compound CCCSCN(C(=O)OC(C)C)C1=CC=CC(Cl)=C1 YGHIEEJZAFAFMP-UHFFFAOYSA-N 0.000 description 1
- FNQSNZVNPNRQHT-UHFFFAOYSA-N propan-2-yl n-(5-chloro-2-methoxyphenyl)-n-(chloromethyl)carbamate Chemical compound COC1=CC=C(Cl)C=C1N(CCl)C(=O)OC(C)C FNQSNZVNPNRQHT-UHFFFAOYSA-N 0.000 description 1
- LFRVDSZCTTUMTO-UHFFFAOYSA-N propan-2-yl n-(chloromethyl)-n-[3-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)OC(=O)N(CCl)C1=CC=CC(C(F)(F)F)=C1 LFRVDSZCTTUMTO-UHFFFAOYSA-N 0.000 description 1
- OQCGBCGJTUZBPI-UHFFFAOYSA-N propan-2-yl n-(chloromethyl)-n-phenylcarbamate Chemical compound CC(C)OC(=O)N(CCl)C1=CC=CC=C1 OQCGBCGJTUZBPI-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 230000014284 seed dormancy process Effects 0.000 description 1
- 230000007226 seed germination Effects 0.000 description 1
- 230000021217 seedling development Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
- RDKYCKDVIYTSAJ-UHFFFAOYSA-M sodium;4-oxopentanoate Chemical compound [Na+].CC(=O)CCC([O-])=O RDKYCKDVIYTSAJ-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722214057 DE2214057A1 (de) | 1972-03-23 | 1972-03-23 | N-arylcarbamidsaeureester, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren |
| EG235/72A EG10699A (en) | 1971-06-23 | 1972-06-06 | Novel n.carbamic aryl acid esters method for preparation and their use for controlling plant growth |
| DD171502*A DD107910A5 (enrdf_load_stackoverflow) | 1971-06-23 | 1972-06-20 | |
| IL7239719A IL39719A (en) | 1971-06-23 | 1972-06-20 | N-arylcarbamic acid esters,their preparation and their use as plant-growth regulators |
| SE7208183A SE380519B (sv) | 1971-06-23 | 1972-06-21 | N-arylkarbamidsyraestrar till anvendning som plattillvextregularer |
| IT26016/72A IT960711B (it) | 1971-06-23 | 1972-06-21 | Esteri n arilcarbammici procedi mento per la loro preparazione e loro impiego come regolatori della crecita delle piante |
| DD163874A DD100621A5 (enrdf_load_stackoverflow) | 1971-06-23 | 1972-06-21 | |
| CH929172A CH584504A5 (enrdf_load_stackoverflow) | 1971-06-23 | 1972-06-21 | |
| HUBA2761A HU165294B (enrdf_load_stackoverflow) | 1971-06-23 | 1972-06-22 | |
| DK312072A DK131854C (da) | 1971-06-23 | 1972-06-22 | Plantevekstregulerende virksomme n-arylcarbamidsyreestere |
| NL7208585A NL7208585A (enrdf_load_stackoverflow) | 1971-06-23 | 1972-06-22 | |
| PL15620672A PL93923B1 (enrdf_load_stackoverflow) | 1972-03-23 | 1972-06-22 | |
| BE785264A BE785264A (enrdf_load_stackoverflow) | 1971-06-23 | 1972-06-22 | |
| CA145,396A CA1025458A (en) | 1971-06-23 | 1972-06-22 | N-arylcarbamic acid esters, processes for their preparation and their use as plant-growth regulators |
| GB2951772A GB1339116A (en) | 1971-06-23 | 1972-06-23 | N-arylcarbamic acid esters processes for their preparation and their use as plant-growth regulators |
| FR7222914A FR2144302A5 (enrdf_load_stackoverflow) | 1971-06-23 | 1972-06-23 | |
| US265909A US3920727A (en) | 1971-06-23 | 1972-06-23 | Novel n-arylcarbamic acid esters |
| AT543172A AT317609B (de) | 1971-06-23 | 1972-06-23 | Pflanzenwachstumsregulierendes Mittel |
| JP6250472A JPS563342B1 (enrdf_load_stackoverflow) | 1971-06-23 | 1972-06-23 | |
| US05/632,742 US4093447A (en) | 1971-06-23 | 1975-11-17 | N-Arylcarbamic acid esters and plant growth regulant compositions and methods |
| US05/853,971 USRE30578E (en) | 1971-06-23 | 1977-11-22 | N-arylcarbamic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722214057 DE2214057A1 (de) | 1972-03-23 | 1972-03-23 | N-arylcarbamidsaeureester, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2214057A1 true DE2214057A1 (de) | 1973-10-11 |
Family
ID=5839848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722214057 Pending DE2214057A1 (de) | 1971-06-23 | 1972-03-23 | N-arylcarbamidsaeureester, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2214057A1 (enrdf_load_stackoverflow) |
| PL (1) | PL93923B1 (enrdf_load_stackoverflow) |
-
1972
- 1972-03-23 DE DE19722214057 patent/DE2214057A1/de active Pending
- 1972-06-22 PL PL15620672A patent/PL93923B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL93923B1 (enrdf_load_stackoverflow) | 1977-07-30 |
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Legal Events
| Date | Code | Title | Description |
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| OHN | Withdrawal |