DD208906A5 - Mittel zur hemmung des pflanzenwachstums - Google Patents
Mittel zur hemmung des pflanzenwachstums Download PDFInfo
- Publication number
- DD208906A5 DD208906A5 DD82236948A DD23694882A DD208906A5 DD 208906 A5 DD208906 A5 DD 208906A5 DD 82236948 A DD82236948 A DD 82236948A DD 23694882 A DD23694882 A DD 23694882A DD 208906 A5 DD208906 A5 DD 208906A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alkyl
- optionally substituted
- formula
- hydrogen
- carbon atoms
- Prior art date
Links
- 230000008635 plant growth Effects 0.000 title claims abstract description 12
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- -1 alkali metal cation Chemical group 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 24
- 150000003851 azoles Chemical class 0.000 claims description 23
- 239000004480 active ingredient Substances 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 19
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000003107 substituted aryl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 229910052751 metal Chemical class 0.000 claims description 8
- 239000002184 metal Chemical class 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- JVBGAHYNGUWVAI-UHFFFAOYSA-N 4-pyrimidin-2-ylbutan-1-ol Chemical class OCCCCC1=NC=CC=N1 JVBGAHYNGUWVAI-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 150000003007 phosphonic acid derivatives Chemical class 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000005131 dialkylammonium group Chemical group 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 211
- 125000004432 carbon atom Chemical group C* 0.000 description 77
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 64
- 125000001309 chloro group Chemical group Cl* 0.000 description 60
- 229920001577 copolymer Chemical class 0.000 description 44
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
- 238000002844 melting Methods 0.000 description 35
- 230000008018 melting Effects 0.000 description 35
- 239000003921 oil Substances 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- 239000011737 fluorine Substances 0.000 description 25
- 229910052731 fluorine Inorganic materials 0.000 description 25
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 24
- 229910052801 chlorine Inorganic materials 0.000 description 23
- 230000009036 growth inhibition Effects 0.000 description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 20
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 125000005843 halogen group Chemical group 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- 230000012010 growth Effects 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 241000209219 Hordeum Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 230000002195 synergetic effect Effects 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- UZPWKTCMUADILM-UHFFFAOYSA-N 3-methylcyclohexene Chemical compound CC1CCCC=C1 UZPWKTCMUADILM-UHFFFAOYSA-N 0.000 description 4
- XVKFDCVTYBMNRZ-UHFFFAOYSA-N 3-methylidenecyclohexene Chemical compound C=C1CCCC=C1 XVKFDCVTYBMNRZ-UHFFFAOYSA-N 0.000 description 4
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000000068 chlorophenyl group Chemical group 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZDZOJEUYRFMJHH-UHFFFAOYSA-N 2-tert-butyl-2-[(4-chlorophenoxy)methyl]oxirane Chemical compound C=1C=C(Cl)C=CC=1OCC1(C(C)(C)C)CO1 ZDZOJEUYRFMJHH-UHFFFAOYSA-N 0.000 description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 230000009422 growth inhibiting effect Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000017066 negative regulation of growth Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- WISVKXCNQOLCJL-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)COC1=CC=C(Cl)C=C1 WISVKXCNQOLCJL-UHFFFAOYSA-N 0.000 description 2
- PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical class OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 description 2
- UIQGEWJEWJMQSL-UHFFFAOYSA-N 2,2,4,4-tetramethylpentan-3-one Chemical class CC(C)(C)C(=O)C(C)(C)C UIQGEWJEWJMQSL-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229910014033 C-OH Inorganic materials 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- 229910014570 C—OH Inorganic materials 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- 239000011135 tin Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- HFFZSMFXOBHQLV-UHFFFAOYSA-M tributylstannyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)CCCC HFFZSMFXOBHQLV-UHFFFAOYSA-M 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cultivation Of Plants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fertilizers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3102588A DE3102588A1 (de) | 1981-01-27 | 1981-01-27 | Mittel zur hemmung des pflanzenwachstums |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD208906A5 true DD208906A5 (de) | 1984-04-18 |
Family
ID=6123411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82236948A DD208906A5 (de) | 1981-01-27 | 1982-01-25 | Mittel zur hemmung des pflanzenwachstums |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US4452625A (en, 2012) |
| EP (1) | EP0057357B1 (en, 2012) |
| JP (1) | JPS57142904A (en, 2012) |
| AT (1) | ATE8563T1 (en, 2012) |
| AU (1) | AU554573B2 (en, 2012) |
| BR (1) | BR8200433A (en, 2012) |
| CA (1) | CA1177660A (en, 2012) |
| CS (1) | CS227031B2 (en, 2012) |
| DD (1) | DD208906A5 (en, 2012) |
| DE (2) | DE3102588A1 (en, 2012) |
| DK (1) | DK34182A (en, 2012) |
| HU (1) | HU187442B (en, 2012) |
| IL (1) | IL64856A (en, 2012) |
| PL (1) | PL129395B1 (en, 2012) |
| ZA (1) | ZA82498B (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU542623B2 (en) * | 1980-05-16 | 1985-02-28 | Bayer Aktiengesellschaft | 1-hydroxyethyl-azole derivatives |
| JPS57165370A (en) * | 1981-03-18 | 1982-10-12 | Ici Ltd | Triazole or imidazole compounds, manufacture and fungicidal or plant growth regulant agent |
| DE3202613A1 (de) * | 1982-01-27 | 1983-08-04 | Bayer Ag, 5090 Leverkusen | Antimykotische mittel |
| DE3202601A1 (de) * | 1982-01-27 | 1983-08-04 | Bayer Ag, 5090 Leverkusen | Substituierte 1 -hydroxyalkyl-azolyl-derivate, verfahren zu ihrer herstellung sowie ihrer verwendung als fungizide und pflanzenwachstumsregulatoren |
| US4940481A (en) * | 1982-03-04 | 1990-07-10 | Ciba-Geigy Corporation | Microbicidal and growth regulating compositions |
| DE3229274A1 (de) * | 1982-08-05 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Substituierte azolylvinyl-ketone und -carbinole |
| US4584376A (en) * | 1982-11-10 | 1986-04-22 | Monsanto Company | 1-heterocyclicthio-1-cyclopropanecarbonitriles as crop protectants |
| JPS59204105A (ja) * | 1983-05-02 | 1984-11-19 | Sumitomo Chem Co Ltd | 植物成長抑制剤組成物 |
| DE3321422A1 (de) * | 1983-06-14 | 1984-12-20 | Basf Ag, 6700 Ludwigshafen | Neue azolverbindungen |
| DE3322818A1 (de) * | 1983-06-24 | 1985-01-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von e-isomeren von 1-cyclohexyl-2-(1,2,4-triazol-1-yl)-1-penten-3-on-derivaten |
| DE3333411A1 (de) * | 1983-09-16 | 1985-04-04 | Bayer Ag, 5090 Leverkusen | Fungizide mittel |
| US5250560A (en) * | 1983-09-16 | 1993-10-05 | Bayer Aktiengesellschaft | Fungicidal agents |
| DE3340989A1 (de) * | 1983-11-10 | 1985-05-23 | Schering AG, 1000 Berlin und 4709 Bergkamen | E-triazolyl-pentenole, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide und wuchsregulatorische mittel |
| DE3342692A1 (de) * | 1983-11-25 | 1985-06-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von ss-hydroxyethyl-(1,2,4-triazol)-derivaten |
| DE3501856A1 (de) * | 1985-01-22 | 1986-07-24 | Bayer Ag, 5090 Leverkusen | Mittel zur regulierung des pflanzenwachstums |
| DE3509823A1 (de) * | 1985-03-19 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung des (-)-antipoden des (e)-1-cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ens |
| DE3709806A1 (de) * | 1987-03-25 | 1988-10-06 | Basf Ag | Mittel zur regulierung des pflanzenwachstums |
| DE4300452A1 (de) * | 1993-01-11 | 1994-07-14 | Bayer Ag | Mittel zur Hemmung des Pflanzenwachstums |
| JPH0873441A (ja) * | 1993-11-01 | 1996-03-19 | Nissan Chem Ind Ltd | 新規４，５−ジ置換ピリミジン誘導体及び除草剤 |
| US6642179B2 (en) * | 2000-08-29 | 2003-11-04 | Thomas L. Watschke | Inhibition of vegetative growth |
| EP1423007B1 (de) * | 2001-04-12 | 2007-06-06 | Basf Aktiengesellschaft | Bioregulatorische wirkstoffkombination |
| CA2495567C (en) * | 2002-08-19 | 2011-11-15 | Basf Aktiengesellschaft | Agents containing carboxylic acid and the use of the same in plant cultivation |
| WO2006099129A2 (en) * | 2005-03-11 | 2006-09-21 | The Regents Of The University Of California | Method of inhibiting ethylene production in plants |
| WO2008068307A2 (en) * | 2006-12-07 | 2008-06-12 | Basf Se | Compositions and kits comprising a fungicidal triazole and an alkoxylated alcohol, and their uses |
| EP2837287A1 (en) | 2013-08-15 | 2015-02-18 | Bayer CropScience AG | Use of prothioconazole for increasing root growth of Brassicaceae |
| CN106397346B (zh) * | 2016-08-31 | 2018-12-07 | 黑龙江八一农垦大学 | 1-(3-氨基-1,2,4-三唑)-基-3,3-二甲基-2-丁酮及其应用 |
| ES2979246T3 (es) * | 2017-03-31 | 2024-09-25 | Valent Biosciences Llc | Formulaciones de clorhidrato de ácido 1-amino-1-ciclopropanocarboxílico |
| US11350630B2 (en) | 2017-03-31 | 2022-06-07 | Valent Biosciences Llc | 1-amino-1-cyclopropanecarboxylic acid hydrochloride formulations |
| EP4171223A4 (en) * | 2020-06-26 | 2024-07-17 | Valent BioSciences LLC | 1-AMINO-1-CYCLOPROPANE CARBOXYLIC ACID MIXTURES AND USES THEREOF |
| UY39924A (es) * | 2021-09-03 | 2023-03-31 | Valent Biosciences Llc | Ácido 1-amino-1-ciclopropancarboxílico para el raleo de frutos |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4401454A (en) * | 1969-10-24 | 1983-08-30 | Union Carbide Corporation | Growth regulation methods |
| EP0005600A1 (en) * | 1978-05-11 | 1979-11-28 | Imperial Chemical Industries Plc | Imidazolyl and triazolyl compounds, compositions containing them and methods of using them as plant fungicidal and growth regulating agents |
| US4554017A (en) * | 1978-06-03 | 1985-11-19 | Bayer Aktiengesellschaft | Method and compositions for regulating plant growth using cycloalkane-carboxylic acid compounds |
| DE2906061A1 (de) * | 1979-02-16 | 1981-01-08 | Bayer Ag | 1-vinyltriazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als wachstumsregulatoren und fungizide |
| FR2461458A1 (fr) * | 1979-07-19 | 1981-02-06 | Roussel Uclaf | Pyrethrinoides a titre de regulateurs de developpement des cultures |
-
1981
- 1981-01-27 DE DE3102588A patent/DE3102588A1/de not_active Withdrawn
-
1982
- 1982-01-07 US US06/337,648 patent/US4452625A/en not_active Expired - Lifetime
- 1982-01-15 DE DE8282100251T patent/DE3260410D1/de not_active Expired
- 1982-01-15 EP EP82100251A patent/EP0057357B1/de not_active Expired
- 1982-01-15 AT AT82100251T patent/ATE8563T1/de not_active IP Right Cessation
- 1982-01-25 DD DD82236948A patent/DD208906A5/de unknown
- 1982-01-25 CS CS82509A patent/CS227031B2/cs unknown
- 1982-01-25 IL IL64856A patent/IL64856A/xx unknown
- 1982-01-26 AU AU79828/82A patent/AU554573B2/en not_active Ceased
- 1982-01-26 HU HU82219A patent/HU187442B/hu not_active IP Right Cessation
- 1982-01-26 BR BR8200433A patent/BR8200433A/pt unknown
- 1982-01-26 JP JP57009643A patent/JPS57142904A/ja active Granted
- 1982-01-26 DK DK34182A patent/DK34182A/da not_active Application Discontinuation
- 1982-01-26 CA CA000394935A patent/CA1177660A/en not_active Expired
- 1982-01-26 PL PL1982234834A patent/PL129395B1/pl unknown
- 1982-01-26 ZA ZA82498A patent/ZA82498B/xx unknown
-
1984
- 1984-02-08 US US06/578,233 patent/US4911750A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3260410D1 (en) | 1984-08-30 |
| HU187442B (en) | 1986-01-28 |
| AU7982882A (en) | 1982-08-05 |
| DK34182A (da) | 1982-07-28 |
| CS227031B2 (en) | 1984-04-16 |
| EP0057357A2 (de) | 1982-08-11 |
| IL64856A0 (en) | 1982-03-31 |
| ZA82498B (en) | 1982-12-29 |
| EP0057357B1 (de) | 1984-07-25 |
| JPH0521882B2 (en, 2012) | 1993-03-25 |
| AU554573B2 (en) | 1986-08-28 |
| DE3102588A1 (de) | 1982-08-12 |
| US4911750A (en) | 1990-03-27 |
| CA1177660A (en) | 1984-11-13 |
| US4452625A (en) | 1984-06-05 |
| BR8200433A (pt) | 1982-11-30 |
| PL129395B1 (en) | 1984-05-31 |
| JPS57142904A (en) | 1982-09-03 |
| EP0057357A3 (en) | 1982-09-08 |
| IL64856A (en) | 1985-10-31 |
| ATE8563T1 (de) | 1984-08-15 |
| PL234834A1 (en, 2012) | 1982-08-30 |
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