DE2162819B2 - Mittel zur Hemmung des long i tu dinalen Zellenwachstums von Pflanzen - Google Patents
Mittel zur Hemmung des long i tu dinalen Zellenwachstums von PflanzenInfo
- Publication number
- DE2162819B2 DE2162819B2 DE2162819A DE2162819A DE2162819B2 DE 2162819 B2 DE2162819 B2 DE 2162819B2 DE 2162819 A DE2162819 A DE 2162819A DE 2162819 A DE2162819 A DE 2162819A DE 2162819 B2 DE2162819 B2 DE 2162819B2
- Authority
- DE
- Germany
- Prior art keywords
- radical
- pyrazine
- ppm
- methanol
- radicals
- 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.)
- Granted
Links
- 230000002401 inhibitory effect Effects 0.000 title claims description 6
- 230000010261 cell growth Effects 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000012749 thinning agent Substances 0.000 claims 1
- -1 2-heptenyl Chemical group 0.000 description 66
- 241000196324 Embryophyta Species 0.000 description 61
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 50
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 40
- 244000068988 Glycine max Species 0.000 description 39
- 235000010469 Glycine max Nutrition 0.000 description 38
- 244000025254 Cannabis sativa Species 0.000 description 37
- 238000002360 preparation method Methods 0.000 description 20
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 19
- 235000007516 Chrysanthemum Nutrition 0.000 description 15
- 150000003216 pyrazines Chemical class 0.000 description 15
- 230000012010 growth Effects 0.000 description 14
- 241000723353 Chrysanthemum Species 0.000 description 13
- 239000007921 spray Substances 0.000 description 13
- 239000002689 soil Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 230000008635 plant growth Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- LFCWHDGQCWJKCG-UHFFFAOYSA-N pyrazin-2-ylmethanol Chemical compound OCC1=CN=CC=N1 LFCWHDGQCWJKCG-UHFFFAOYSA-N 0.000 description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
- 235000007319 Avena orientalis Nutrition 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000003306 harvesting Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 4
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 244000105624 Arachis hypogaea Species 0.000 description 3
- 240000008067 Cucumis sativus Species 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 240000002395 Euphorbia pulcherrima Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- YKZSVEVTRUSPOQ-UHFFFAOYSA-N cyclopropyl-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1CC1 YKZSVEVTRUSPOQ-UHFFFAOYSA-N 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 235000020232 peanut Nutrition 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- 239000012264 purified product Substances 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000005810 2,5-xylyl group Chemical group [H]C1=C([H])C(=C(*)C([H])=C1C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- NQJKHIJTEVVVKS-UHFFFAOYSA-N 2-benzhydrylpyrazine Chemical compound C1=CC=CC=C1C(C=1N=CC=NC=1)C1=CC=CC=C1 NQJKHIJTEVVVKS-UHFFFAOYSA-N 0.000 description 2
- OYWPFIUVDKHHGQ-UHFFFAOYSA-N 2-iodopyrazine Chemical compound IC1=CN=CC=N1 OYWPFIUVDKHHGQ-UHFFFAOYSA-N 0.000 description 2
- 235000002629 Acer saccharinum Nutrition 0.000 description 2
- 244000046139 Acer saccharum Species 0.000 description 2
- 235000004421 Acer saccharum Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 2
- 241000218631 Coniferophyta Species 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- 240000006497 Dianthus caryophyllus Species 0.000 description 2
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 235000014486 Hydrangea macrophylla Nutrition 0.000 description 2
- 241001091442 Hydrangeaceae Species 0.000 description 2
- 241000721662 Juniperus Species 0.000 description 2
- 241000735234 Ligustrum Species 0.000 description 2
- 241000234435 Lilium Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 235000006485 Platanus occidentalis Nutrition 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 244000152045 Themeda triandra Species 0.000 description 2
- 241001520823 Zoysia Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000000994 depressogenic effect Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000010871 livestock manure Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003595 mist Substances 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 2
- GYWHHKFEGKGDTB-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)-2-methylpropan-1-one Chemical compound C1CC2C(C(=O)C(C)C)CC1C2 GYWHHKFEGKGDTB-UHFFFAOYSA-N 0.000 description 1
- VASTZFXIPBJXFK-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-methylbutan-1-one Chemical compound CCC(C)C(=O)C1=CC=C(OC)C=C1 VASTZFXIPBJXFK-UHFFFAOYSA-N 0.000 description 1
- CHOMHKNFOBWRCW-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-methylpropan-1-one Chemical compound COC1=CC=C(C(=O)C(C)C)C=C1 CHOMHKNFOBWRCW-UHFFFAOYSA-N 0.000 description 1
- CHAXKMMRXJZVLY-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-methylbut-2-en-1-one Chemical compound COC1=CC=C(C(=O)C=C(C)C)C=C1 CHAXKMMRXJZVLY-UHFFFAOYSA-N 0.000 description 1
- HNHLNYCFOLMJHR-UHFFFAOYSA-N 1-(4-methoxyphenyl)pentan-1-one Chemical compound CCCCC(=O)C1=CC=C(OC)C=C1 HNHLNYCFOLMJHR-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- NIMBXIOSDGOMGO-UHFFFAOYSA-N 1-pyrazin-2-yl-3,4-dihydro-2h-naphthalen-1-ol Chemical compound C1CCC2=CC=CC=C2C1(O)C1=CN=CC=N1 NIMBXIOSDGOMGO-UHFFFAOYSA-N 0.000 description 1
- TUWSWSOREAUSCJ-UHFFFAOYSA-N 1h-benzo[7]annulen-5-ol Chemical compound OC1=CC=CC=C2CC=CC=C12 TUWSWSOREAUSCJ-UHFFFAOYSA-N 0.000 description 1
- 125000003660 2,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- VUYFWTVHDXNKSC-UHFFFAOYSA-N 2-(1-cyclohexylhexyl)pyrazine Chemical compound C1(CCCCC1)C(CCCCC)C1=NC=CN=C1 VUYFWTVHDXNKSC-UHFFFAOYSA-N 0.000 description 1
- FNFQUNAGIYRWMB-UHFFFAOYSA-N 2-(4-ethylcyclohexyl)pyrazine Chemical compound C(C)C1CCC(CC1)C1=NC=CN=C1 FNFQUNAGIYRWMB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006026 2-methyl-1-butenyl group Chemical group 0.000 description 1
- DIANJNDWLUCSDF-UHFFFAOYSA-N 2-methyl-1-naphthalen-1-ylpropan-1-one Chemical compound C1=CC=C2C(C(=O)C(C)C)=CC=CC2=C1 DIANJNDWLUCSDF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000005925 3-methylpentyloxy group Chemical group 0.000 description 1
- ZNNSPZOSKINXHF-UHFFFAOYSA-N 5-sulfinylcyclohexa-1,3-diene Chemical compound O=S=C1CC=CC=C1 ZNNSPZOSKINXHF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 241000132092 Aster Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CHQFCMCIFJOZMA-UHFFFAOYSA-N C1(=CC=CC=C1)C1CC(C1)C1=NC=CN=C1 Chemical compound C1(=CC=CC=C1)C1CC(C1)C1=NC=CN=C1 CHQFCMCIFJOZMA-UHFFFAOYSA-N 0.000 description 1
- MJNCFCOWBRYGGN-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3C(C12)C1=NC=CN=C1 Chemical compound C1=CC=CC=2C3=CC=CC=C3C(C12)C1=NC=CN=C1 MJNCFCOWBRYGGN-UHFFFAOYSA-N 0.000 description 1
- AJPITOILIUOMCY-UHFFFAOYSA-N CC(C)C(C1=CC(CC(F)(F)F)=CC=C1)=O Chemical compound CC(C)C(C1=CC(CC(F)(F)F)=CC=C1)=O AJPITOILIUOMCY-UHFFFAOYSA-N 0.000 description 1
- SLQAECKJNVNHLQ-UHFFFAOYSA-N CCC1=C(C(C2=C(CC)SC=C2C2CC2)=O)C(C2CC2)=CS1 Chemical compound CCC1=C(C(C2=C(CC)SC=C2C2CC2)=O)C(C2CC2)=CS1 SLQAECKJNVNHLQ-UHFFFAOYSA-N 0.000 description 1
- UQBLLBGFLVAGQC-UHFFFAOYSA-N CCCCCC(CCC1=NC=C(C2=C(CCC)SC=C2)N=C1C)OCC Chemical compound CCCCCC(CCC1=NC=C(C2=C(CCC)SC=C2)N=C1C)OCC UQBLLBGFLVAGQC-UHFFFAOYSA-N 0.000 description 1
- LGRIGOASOXQWOS-UHFFFAOYSA-N COC1=CC=CC=C1.BrC1=CC=CC=C1 Chemical compound COC1=CC=CC=C1.BrC1=CC=CC=C1 LGRIGOASOXQWOS-UHFFFAOYSA-N 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000156961 Coenonympha Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 244000052363 Cynodon dactylon Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 240000008669 Hedera helix Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- DBUJUFMPYGTWAI-UHFFFAOYSA-N O=C1CCC#CCC1 Chemical compound O=C1CCC#CCC1 DBUJUFMPYGTWAI-UHFFFAOYSA-N 0.000 description 1
- CPLLBIZSXNFUTB-UHFFFAOYSA-N OC1(C2=CC=CC=C2SC=2C=CC=CC12)C1=NC=CN=C1 Chemical compound OC1(C2=CC=CC=C2SC=2C=CC=CC12)C1=NC=CN=C1 CPLLBIZSXNFUTB-UHFFFAOYSA-N 0.000 description 1
- 241000758706 Piperaceae Species 0.000 description 1
- 241000209464 Platanaceae Species 0.000 description 1
- 244000268528 Platanus occidentalis Species 0.000 description 1
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 244000082988 Secale cereale Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241001149163 Ulmus americana Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- KMWTUCKAZFNWNG-UHFFFAOYSA-N cyclobutyl-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1CCC1 KMWTUCKAZFNWNG-UHFFFAOYSA-N 0.000 description 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 description 1
- HZRHGOMCJOCIPT-UHFFFAOYSA-N cyclohexyl(cyclopropyl)methanone Chemical compound C1CCCCC1C(=O)C1CC1 HZRHGOMCJOCIPT-UHFFFAOYSA-N 0.000 description 1
- VYDIMQRLNMMJBW-UHFFFAOYSA-N cyclopentyl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1CCCC1 VYDIMQRLNMMJBW-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SZYQPTAROQANMV-UHFFFAOYSA-N ethyl pyrazine-2-carboxylate Chemical compound CCOC(=O)C1=CN=CC=N1 SZYQPTAROQANMV-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- SKRPCQXQBBHPKO-UHFFFAOYSA-N fluorocyclobutane Chemical compound FC1CCC1 SKRPCQXQBBHPKO-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000007773 growth pattern Effects 0.000 description 1
- XFXWEAWJVWCOBF-UHFFFAOYSA-N hept-6-en-3-ol Chemical compound CCC(O)CCC=C XFXWEAWJVWCOBF-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- XWZMOEJHQNDROY-UHFFFAOYSA-N methanol;pyrazine Chemical class OC.C1=CN=CC=N1 XWZMOEJHQNDROY-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9923370A | 1970-12-17 | 1970-12-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2162819A1 DE2162819A1 (de) | 1972-07-06 |
| DE2162819B2 true DE2162819B2 (de) | 1973-10-04 |
| DE2162819C3 DE2162819C3 (enExample) | 1974-05-02 |
Family
ID=22273766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2162819A Granted DE2162819B2 (de) | 1970-12-17 | 1971-12-17 | Mittel zur Hemmung des long i tu dinalen Zellenwachstums von Pflanzen |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5617323B1 (enExample) |
| AT (1) | AT316195B (enExample) |
| AU (1) | AU459893B2 (enExample) |
| BE (1) | BE776762A (enExample) |
| BR (1) | BR7108350D0 (enExample) |
| CA (1) | CA985524A (enExample) |
| CH (1) | CH581425A5 (enExample) |
| DE (1) | DE2162819B2 (enExample) |
| DK (1) | DK137062B (enExample) |
| FR (1) | FR2119984B1 (enExample) |
| GB (1) | GB1361816A (enExample) |
| IE (1) | IE35907B1 (enExample) |
| IL (1) | IL38374A (enExample) |
| IT (1) | IT984583B (enExample) |
| NL (1) | NL7117312A (enExample) |
| SE (1) | SE394359B (enExample) |
| ZA (1) | ZA718339B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4194899A (en) * | 1973-06-18 | 1980-03-25 | Eli Lilly And Company | Fluoroalkoxyphenyl-substituted nitrogen heterocycles |
| DE3105374A1 (de) * | 1981-02-14 | 1982-09-02 | Bayer Ag, 5090 Leverkusen | Benzyl-pyrimidinylalkyl-ether, verfahren zu ihrer herstellung, ihre verwendung als pflanzenwachstumsregulatoren und fungizide sowie zwischenprodukte und deren herstellung |
| US4933339A (en) * | 1985-08-21 | 1990-06-12 | Rohm And Haas Company | (2-cyano-2-arylethyl)pyridine compounds useful in controlling fungicidal activity |
| GB8714537D0 (en) * | 1987-06-22 | 1987-07-29 | Ici Plc | Pyrazine derivatives |
| GB8814639D0 (en) * | 1988-06-20 | 1988-07-27 | Ici Plc | Heterocyclic tertiary alcohol derivatives |
| CN103524434B (zh) * | 2013-09-29 | 2015-08-12 | 北京大学 | 植物乙烯合成途径的小分子抑制剂吡嗪酰胺及其应用 |
-
1971
- 1971-12-13 ZA ZA718339A patent/ZA718339B/xx unknown
- 1971-12-15 AU AU36883/71A patent/AU459893B2/en not_active Expired
- 1971-12-15 IL IL38374A patent/IL38374A/xx unknown
- 1971-12-16 BE BE776762A patent/BE776762A/xx unknown
- 1971-12-16 BR BR8350/71A patent/BR7108350D0/pt unknown
- 1971-12-16 DK DK615471AA patent/DK137062B/da unknown
- 1971-12-16 NL NL7117312A patent/NL7117312A/xx not_active Application Discontinuation
- 1971-12-16 AT AT1081571A patent/AT316195B/de not_active IP Right Cessation
- 1971-12-16 CA CA130,284A patent/CA985524A/en not_active Expired
- 1971-12-17 GB GB5872771A patent/GB1361816A/en not_active Expired
- 1971-12-17 SE SE7116250A patent/SE394359B/xx unknown
- 1971-12-17 JP JP10253471A patent/JPS5617323B1/ja active Pending
- 1971-12-17 IT IT54812/71A patent/IT984583B/it active
- 1971-12-17 IE IE1602/71A patent/IE35907B1/xx unknown
- 1971-12-17 CH CH1846971A patent/CH581425A5/xx not_active IP Right Cessation
- 1971-12-17 DE DE2162819A patent/DE2162819B2/de active Granted
- 1971-12-17 FR FR7145516A patent/FR2119984B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK137062C (enExample) | 1978-06-19 |
| GB1361816A (en) | 1974-07-30 |
| DK137062B (da) | 1978-01-16 |
| AT316195B (de) | 1974-06-25 |
| SE394359B (sv) | 1977-06-27 |
| NL7117312A (enExample) | 1972-06-20 |
| BR7108350D0 (pt) | 1973-05-17 |
| ZA718339B (en) | 1973-07-25 |
| CA985524A (en) | 1976-03-16 |
| DE2162819A1 (de) | 1972-07-06 |
| BE776762A (fr) | 1972-06-16 |
| AU3688371A (en) | 1973-06-21 |
| FR2119984A1 (enExample) | 1972-08-11 |
| IE35907B1 (en) | 1976-06-23 |
| IL38374A0 (en) | 1972-03-28 |
| AU459893B2 (en) | 1975-04-10 |
| IE35907L (en) | 1972-06-17 |
| DE2162819C3 (enExample) | 1974-05-02 |
| IT984583B (it) | 1974-11-20 |
| JPS5617323B1 (enExample) | 1981-04-22 |
| IL38374A (en) | 1975-10-15 |
| CH581425A5 (enExample) | 1976-11-15 |
| FR2119984B1 (enExample) | 1974-09-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0007990B1 (de) | Pyrazolätherderivate, Verfahren zu ihrer Herstellung und Herbizide, die diese Verbindungen enthalten | |
| DE2207575A1 (de) | Mittel zur regulierung des pflanzenwachstums | |
| EP0017946B1 (de) | Salze von Alpha-Aminoacetaniliden, Verfahren zu ihrer Herstellung und ihre Anwendung als Pflanzenwachstumsregulatoren | |
| DE2640484A1 (de) | Amidoxim-derivate, ihre herstellung und verwendung | |
| EP0434613B1 (de) | Synergistisch wirkendes Mittel und Verfahren zur Regulierung des Pflanzenwuchses | |
| EP0003805A1 (de) | Pyridazonverbindungen und diese enthaltende herbizide Zusammensetzungen | |
| EP0086173A1 (de) | Fungizid wirkende und den Pflanzenwuchs regulierende Triazolcarbinolderivate | |
| DE2933405C2 (de) | Racemisches und optisch aktives 2-(Propargyloximino)-1,7,7-trimethylbicyclo[2,2,1]-heptan, Verfahren zu deren Herstellung und solche enthaltende pflanzenwuchsregelnde und insektizide Mittel | |
| DE2162819B2 (de) | Mittel zur Hemmung des long i tu dinalen Zellenwachstums von Pflanzen | |
| DE2615878C2 (de) | Polycyclische stickstoffhaltige Verbindungen | |
| EP0183217B1 (de) | Mikrobizide Mittel | |
| EP0026872B1 (de) | Pflanzenwachstumsregulierende Mittel enthaltend substituierte Alkylammoniumsalze und deren Verwendung | |
| EP0019762B1 (de) | Triazolylderivate, Verfahren zu ihrer Herstellung sowie diese enthaltende Mittel zur Beeinflussung des Pflanzenwachstums | |
| EP0031114B1 (de) | Phenylpropylammoniumsalze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Mittel | |
| DE2842801A1 (de) | Beta-triazolyloxime | |
| EP0046445B1 (de) | 3-Phenoxy-methylenaniline als Herbizide, ihre Herstellung und Verwendung | |
| EP0005516B1 (de) | Substituierte Pyridazone, Verfahren zu ihrer Herstellung und ihre Anwendung als Herbizide | |
| DD262992A5 (de) | Nematizide und insektizide zusammensetzung | |
| CH677664A5 (enExample) | ||
| DE2362333C3 (de) | Thionophosphorsäureesteramide, Verfahren zu deren Herstellung und Verwendung derselben | |
| DE3604871A1 (de) | Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung als mittel zur regulierung des pflanzenwachstums | |
| EP0069244A1 (de) | Verfahren zur Beeinflussung des Pflanzenwachstums | |
| DE2751782A1 (de) | Mittel zur regulierung des pflanzenwachstums | |
| DE2348022A1 (de) | Sulfonamid-zubereitungen fuer herbicide | |
| DE2635967A1 (de) | 2-cyanacetamid-derivate und ihre herstellung und anwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |