DD256639A5 - Herbizide und pflanzenwuchsregulierende mittel - Google Patents

Herbizide und pflanzenwuchsregulierende mittel Download PDF

Info

Publication number: DD256639A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; case; nitro; pyridyl; carbon atoms
Prior art date: 1985-12-05

Application number

DD86297074A

Other languages

German (de)

English (en)

Inventor

Reinhold Gehring

Otto Schallner

Joerg Stetter

Hans-Joachim Santel

Robert R Schmidt

Klaus Luerssen

Original Assignee

��@��k��

Priority date (The priority date 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 date listed.)

1985-12-05

Filing date

1986-12-04

Publication date

1988-05-18

1986-12-04 Application filed by ��@��k�� filed Critical ��@��k��

1988-05-18 Publication of DD256639A5 publication Critical patent/DD256639A5/de

Links

239000003795 chemical substances by application Substances 0.000 title claims description 7
239000004009 herbicide Substances 0.000 title description 6
230000002363 herbicidal effect Effects 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
239000000460 chlorine Substances 0.000 claims description 110
241000196324 Embryophyta Species 0.000 claims description 39
-1 Chloro, bromo, iodo, methyl Chemical group 0.000 claims description 36
238000000034 method Methods 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
239000011737 fluorine Substances 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000001188 haloalkyl group Chemical group 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
239000004606 Fillers/Extenders Substances 0.000 claims description 4
239000013543 active substance Substances 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 4
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical class 0.000 claims description 2
125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000006343 heptafluoro propyl group Chemical group 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 2
239000005648 plant growth regulator Substances 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 15
230000008635 plant growth Effects 0.000 abstract 1
230000001105 regulatory effect Effects 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 40
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000003085 diluting agent Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
238000009472 formulation Methods 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000003995 emulsifying agent Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000007858 starting material Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000008187 granular material Substances 0.000 description 6
239000003630 growth substance Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
229910017604 nitric acid Inorganic materials 0.000 description 6
150000003254 radicals Chemical group 0.000 description 6
239000002689 soil Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
230000006378 damage Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000000969 carrier Substances 0.000 description 4
238000006396 nitration reaction Methods 0.000 description 4
239000000843 powder Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
238000005507 spraying Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
QCILTVDORZRFKG-UHFFFAOYSA-N 2,2,2-trifluoro-n-[2-[2,3,6-trichloro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]acetamide Chemical compound FC(F)(F)C(=O)NC1=CC=NN1C1=C(Cl)C=C(C(F)(F)F)C(Cl)=C1Cl QCILTVDORZRFKG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000219146 Gossypium Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
230000035613 defoliation Effects 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000006072 paste Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000013558 reference substance Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
JWGYPTNGYXOXPV-UHFFFAOYSA-N 4-nitro-1h-pyrazol-5-amine Chemical class NC=1NN=CC=1[N+]([O-])=O JWGYPTNGYXOXPV-UHFFFAOYSA-N 0.000 description 2
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244000075850 Avena orientalis Species 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
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XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241000207763 Solanum Species 0.000 description 2
235000002634 Solanum Nutrition 0.000 description 2
235000011684 Sorghum saccharatum Nutrition 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
239000000642 acaricide Substances 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000012973 diazabicyclooctane Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N ethylene glycol dimethyl ether Natural products COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
239000006260 foam Substances 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
238000003306 harvesting Methods 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000011707 mineral Substances 0.000 description 2
230000000802 nitrating effect Effects 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000008096 xylene Substances 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical class CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
SBMWLZYVRBAAOC-UHFFFAOYSA-N 2,2,2-trifluoro-n-[4-nitro-2-[2,3,6-trichloro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]acetamide Chemical compound FC(F)(F)C(=O)NC1=C([N+](=O)[O-])C=NN1C1=C(Cl)C=C(C(F)(F)F)C(Cl)=C1Cl SBMWLZYVRBAAOC-UHFFFAOYSA-N 0.000 description 1
RAPIQURAUADUKF-UHFFFAOYSA-N 2,2-difluoro-n-[2-[2,3,6-trichloro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]acetamide Chemical compound FC(F)C(=O)NC1=CC=NN1C1=C(Cl)C=C(C(F)(F)F)C(Cl)=C1Cl RAPIQURAUADUKF-UHFFFAOYSA-N 0.000 description 1
KUZYDRGGGCWOGV-UHFFFAOYSA-N 2,3-dichloro-2-phenoxypropanoic acid Chemical compound OC(=O)C(Cl)(CCl)OC1=CC=CC=C1 KUZYDRGGGCWOGV-UHFFFAOYSA-N 0.000 description 1
239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
PNSLCQNMSVICGU-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yloxy)-n-phenylacetamide Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)NC1=CC=CC=C1 PNSLCQNMSVICGU-UHFFFAOYSA-N 0.000 description 1
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UILKBFBYELRBBP-UHFFFAOYSA-N 2-[2,3,6-trichloro-4-(trifluoromethyl)phenyl]pyrazol-3-amine Chemical compound NC1=CC=NN1C1=C(Cl)C=C(C(F)(F)F)C(Cl)=C1Cl UILKBFBYELRBBP-UHFFFAOYSA-N 0.000 description 1
OVQJTYOXWVHPTA-UHFFFAOYSA-N 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-nitropyrazol-3-amine Chemical compound NC1=C([N+]([O-])=O)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl OVQJTYOXWVHPTA-UHFFFAOYSA-N 0.000 description 1
SVGBNTOHFITEDI-UHFFFAOYSA-N 2-[4-(3,5-dichloropyridin-2-yl)oxyphenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(Cl)C=C1Cl SVGBNTOHFITEDI-UHFFFAOYSA-N 0.000 description 1
UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
ADZSGNDOZREKJK-UHFFFAOYSA-N 4-amino-6-tert-butyl-3-ethylsulfanyl-1,2,4-triazin-5-one Chemical compound CCSC1=NN=C(C(C)(C)C)C(=O)N1N ADZSGNDOZREKJK-UHFFFAOYSA-N 0.000 description 1
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
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244000215068 Acacia senegal Species 0.000 description 1
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238000010626 work up procedure Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- 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
- C07D231/14—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD86297074A 1985-12-05 1986-12-04 Herbizide und pflanzenwuchsregulierende mittel DD256639A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853543035 DE3543035A1 (de)	1985-12-05	1985-12-05	5-fluoracylamino-4-nitro-1-aryl-pyrazole

Publications (1)

Publication Number	Publication Date
DD256639A5 true DD256639A5 (de)	1988-05-18

Family

ID=6287727

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86297074A DD256639A5 (de)	1985-12-05	1986-12-04	Herbizide und pflanzenwuchsregulierende mittel

Country Status (13)

Country	Link
US (1)	US4808209A (da)
EP (1)	EP0226074A1 (da)
JP (1)	JPS62138476A (da)
KR (1)	KR870006004A (da)
AU (1)	AU6617386A (da)
BR (1)	BR8605976A (da)
DD (1)	DD256639A5 (da)
DE (1)	DE3543035A1 (da)
DK (1)	DK583686A (da)
HU (1)	HU197884B (da)
IL (1)	IL80844A0 (da)
NZ (1)	NZ218462A (da)
ZA (1)	ZA869162B (da)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5256634A (en) *	1984-01-24	1993-10-26	Bayer Aktiengesellschaft	Herbicidal agents based on pyrazole derivatives
GB8713769D0 (en) *	1987-06-12	1987-07-15	May & Baker Ltd	Compositions of matter
DE3725661A1 (de) *	1987-08-03	1989-02-23	Bayer Ag	1-arylpyrazole
DE3726919A1 (de) *	1987-08-13	1989-02-23	Bayer Ag	1-arylpyrazole
US6541273B1 (en)	1999-11-12	2003-04-01	Aventis Cropscience, S.A.	Multiple sorbent cartridges for solid phase extraction
PE20141468A1 (es)	2010-12-21	2014-11-05	Bayer Cropscience Lp	Mutantes tipo papel de lija de bacillus y metodos de uso de los mismo para mejorar el crecimiento vegetal, promover la salud de plantas y controlar enfermedades y plagas
MX2014002890A (es)	2011-09-12	2015-01-19	Bayer Cropscience Lp	Metodo para mejorar la salud y/o promover el crecimiento de una planta y/o mejorar la maduracion de frutos.
CA2894399A1 (en)	2012-12-06	2014-06-12	Quanticel Pharmaceuticals, Inc.	Histone demethylase inhibitors

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57169465A (en) *	1981-04-13	1982-10-19	Showa Denko Kk	Pyrazole derivative, its preparation and herbicide
US4589905A (en) *	1983-11-07	1986-05-20	Eli Lilly And Company	Herbicidal and algicidal 1-aryl-5-cyano-1H-pyrazole-4-carboxamides
US4620865A (en) *	1983-11-07	1986-11-04	Eli Lilly And Company	Herbicidal and algicidal 1,5-disubstituted-1H-pyrazole-4-carboxamides
DE3402308A1 (de) *	1984-01-24	1985-08-01	Bayer Ag, 5090 Leverkusen	Herbizide mittel auf basis von pyrazolderivaten
DE3520330A1 (de) *	1985-06-07	1986-12-11	Bayer Ag, 5090 Leverkusen	5-amino-1-pyridyl-pyrazole

1985
- 1985-12-05 DE DE19853543035 patent/DE3543035A1/de not_active Withdrawn
1986
- 1986-11-24 EP EP86116245A patent/EP0226074A1/de not_active Withdrawn
- 1986-11-24 US US06/934,075 patent/US4808209A/en not_active Expired - Fee Related
- 1986-12-02 NZ NZ218462A patent/NZ218462A/xx unknown
- 1986-12-02 IL IL80844A patent/IL80844A0/xx unknown
- 1986-12-04 ZA ZA869162A patent/ZA869162B/xx unknown
- 1986-12-04 DK DK583686A patent/DK583686A/da not_active Application Discontinuation
- 1986-12-04 DD DD86297074A patent/DD256639A5/de unknown
- 1986-12-04 HU HU865018A patent/HU197884B/hu not_active IP Right Cessation
- 1986-12-05 BR BR8605976A patent/BR8605976A/pt unknown
- 1986-12-05 AU AU66173/86A patent/AU6617386A/en not_active Abandoned
- 1986-12-05 JP JP61289073A patent/JPS62138476A/ja active Pending
- 1986-12-05 KR KR860010398A patent/KR870006004A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
AU6617386A (en)	1987-06-11
HU197884B (en)	1989-06-28
DK583686D0 (da)	1986-12-04
DK583686A (da)	1987-06-06
IL80844A0 (en)	1987-03-31
ZA869162B (en)	1987-08-26
KR870006004A (ko)	1987-07-08
BR8605976A (pt)	1987-09-15
JPS62138476A (ja)	1987-06-22
US4808209A (en)	1989-02-28
DE3543035A1 (de)	1987-06-11
NZ218462A (en)	1989-05-29
EP0226074A1 (de)	1987-06-24
HUT43045A (en)	1987-09-28

Publication	Publication Date	Title
EP0232538B1 (de)	1990-05-23	5-Acylamido-1-aryl-pyrazole
EP0248315A2 (de)	1987-12-09	5-Acylamino-pyrazol-Derivate
DD247372A5 (de)	1987-07-08	Herbizide mittel
EP0257296B1 (de)	1993-05-12	4-Cyano(nitro)-5-oxy(thio)-pyrazol-Derivate
EP0138149A2 (de)	1985-04-24	Substituierte 5-Acylamino-1-phenylpyrazole
DE3617977A1 (de)	1987-06-11	5-dichloracetamido-4-nitro-1-aryl-pyrazole
EP0224019A2 (de)	1987-06-03	1-Aryl-4-nitro-pyrazole
EP0242573A1 (de)	1987-10-28	5-Acylamino-pyrazol-Derivate
EP0205022B1 (de)	1990-01-10	1-Aryl-5-alkoximinoalkylamino-pyrazole
DD256639A5 (de)	1988-05-18	Herbizide und pflanzenwuchsregulierende mittel
EP0171544B1 (de)	1989-01-04	Substituierte 5-Acylamino-1-phenylpyrazole
DE3707551A1 (de)	1988-09-22	Substituierte 1-arylpyrazole
EP0227946A1 (de)	1987-07-08	5-Perfluoracylamino-4-nitro-1-aryl-pyrazol-Salze
EP0224094A2 (de)	1987-06-03	1-Aryl-pyrazole
DD238909A5 (de)	1986-09-10	Herbizide mittel
EP0222253B1 (de)	1989-04-05	Substituierte 5-Amino-1-aryl-pyrazole
DE3637710A1 (de)	1988-05-11	5-acylamino-pyrazol-derivate
DD256640A5 (de)	1988-05-18	Herbizide und pflanzenwuchsregulierende mittel
DE3707686A1 (de)	1988-09-22	4-cyano-1-aryl-pyrazole
DD258558A5 (de)	1988-07-27	1-aryl-5-hydrazino-pyrazole
DD248271A5 (de)	1987-08-05	Herbizide mittel