DD253937A5 - Herbizide mittel - Google Patents

Herbizide mittel Download PDF

Info

Publication number: DD253937A5
Authority: DD; German Democratic Republic
Prior art keywords: case; cyano; haloalkyl; nitro; formula
Prior art date: 1985-11-18

Application number

DD86296291A

Other languages

German (de)

English (en)

Inventor

Uta Jensen-Korte

Reinhold Gehring

Joerg Stetter

Otto Schallner

Hans-Joachim Santel

Robert R Schmidt

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.)

1985-11-18

Filing date

1986-11-14

Publication date

1988-02-10

1986-11-14 Application filed by ��@��k�� filed Critical ��@��k��

1988-02-10 Publication of DD253937A5 publication Critical patent/DD253937A5/de

Links

239000004009 herbicide Substances 0.000 title claims description 5
230000002363 herbicidal effect Effects 0.000 title abstract description 9
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 46
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 35
239000000203 mixture Substances 0.000 claims abstract description 31
125000004961 1-arylpyrazolyl group Chemical group 0.000 claims abstract description 16
-1 alkaline earth Substances 0.000 claims description 134
239000000460 chlorine Chemical group 0.000 claims description 82
238000000034 method Methods 0.000 claims description 81
125000000217 alkyl group Chemical group 0.000 claims description 62
125000001188 haloalkyl group Chemical group 0.000 claims description 55
239000001257 hydrogen Substances 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 52
150000003254 radicals Chemical class 0.000 claims description 45
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
150000002431 hydrogen Chemical class 0.000 claims description 38
125000004432 carbon atom Chemical group C* 0.000 claims description 36
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
229910052760 oxygen Inorganic materials 0.000 claims description 33
239000001301 oxygen Substances 0.000 claims description 33
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
239000011593 sulfur Chemical group 0.000 claims description 31
229910052717 sulfur Inorganic materials 0.000 claims description 31
241000196324 Embryophyta Species 0.000 claims description 26
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 25
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
125000005843 halogen group Chemical group 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 22
150000002367 halogens Chemical class 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 21
125000000304 alkynyl group Chemical group 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 20
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 19
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
229910052801 chlorine Inorganic materials 0.000 claims description 18
125000000262 haloalkenyl group Chemical group 0.000 claims description 18
239000011737 fluorine Substances 0.000 claims description 17
229910052731 fluorine Inorganic materials 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 13
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
229910052794 bromium Inorganic materials 0.000 claims description 13
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 13
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
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 description 13
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 11
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 11
125000004438 haloalkoxy group Chemical group 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 8
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
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 claims description 8
229910052802 copper Inorganic materials 0.000 claims description 8
239000010949 copper Substances 0.000 claims description 8
125000004663 dialkyl amino group Chemical group 0.000 claims description 8
125000001153 fluoro group Chemical group F* 0.000 claims description 8
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 8
125000004368 propenyl group Chemical class C(=CC)* 0.000 claims description 8
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 8
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 7
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 7
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 7
239000010941 cobalt Substances 0.000 claims description 7
229910017052 cobalt Inorganic materials 0.000 claims description 7
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 7
229910052742 iron Inorganic materials 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
239000011734 sodium Substances 0.000 claims description 7
239000011135 tin Substances 0.000 claims description 7
229910052718 tin Inorganic materials 0.000 claims description 7
229910052725 zinc Inorganic materials 0.000 claims description 7
239000011701 zinc Substances 0.000 claims description 7
125000003903 2-propenyl group Chemical class [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 6
125000004369 butenyl group Chemical class C(=CCC)* 0.000 claims description 6
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 6
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 6
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
229910052788 barium Inorganic materials 0.000 claims description 5
239000011575 calcium Substances 0.000 claims description 5
229910052791 calcium Inorganic materials 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 5
239000011777 magnesium Substances 0.000 claims description 5
229910052749 magnesium Inorganic materials 0.000 claims description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical class [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 5
239000011591 potassium Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims description 5
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
239000004606 Fillers/Extenders Substances 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 4
150000001767 cationic compounds Chemical class 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
229910052759 nickel Inorganic materials 0.000 claims description 4
150000002892 organic cations Chemical class 0.000 claims description 4
125000005981 pentynyl group Chemical group 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
229920001577 copolymer Chemical group 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000013543 active substance Substances 0.000 claims 2
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 2
PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical class C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 claims 1
YPFNIPKMNMDDDB-UHFFFAOYSA-K 2-[2-[bis(carboxylatomethyl)amino]ethyl-(2-hydroxyethyl)amino]acetate;iron(3+) Chemical compound [Fe+3].OCCN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O YPFNIPKMNMDDDB-UHFFFAOYSA-K 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
150000001875 compounds Chemical class 0.000 description 43
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 38
239000003085 diluting agent Substances 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
238000002844 melting Methods 0.000 description 27
230000008018 melting Effects 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
235000019441 ethanol Nutrition 0.000 description 22
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
239000007858 starting material Substances 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
239000000126 substance Substances 0.000 description 15
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 14
238000002955 isolation Methods 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 11
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
238000010626 work up procedure Methods 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
KRJGPISCARKCFF-UHFFFAOYSA-N 4-cyano-2-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-3-carboxylic acid Chemical compound OC(=O)C1=C(C#N)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl KRJGPISCARKCFF-UHFFFAOYSA-N 0.000 description 7
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
150000001298 alcohols Chemical class 0.000 description 7
239000002585 base Substances 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
150000002170 ethers Chemical class 0.000 description 7
238000009472 formulation Methods 0.000 description 7
150000002825 nitriles Chemical class 0.000 description 7
239000012071 phase Substances 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
230000006378 damage Effects 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
238000012360 testing method Methods 0.000 description 6
150000003573 thiols Chemical class 0.000 description 6
239000008096 xylene Substances 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
239000001569 carbon dioxide Substances 0.000 description 5
229910002092 carbon dioxide Inorganic materials 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
150000002900 organolithium compounds Chemical class 0.000 description 5
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
241000251730 Chondrichthyes Species 0.000 description 4
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
239000002168 alkylating agent Substances 0.000 description 4
229940100198 alkylating agent Drugs 0.000 description 4
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000008282 halocarbons Chemical class 0.000 description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
150000007530 organic bases Chemical class 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000012286 potassium permanganate Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
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150000003462 sulfoxides Chemical class 0.000 description 4
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125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
QSDFADUFARKNDZ-UHFFFAOYSA-M potassium 4-cyano-2-(2,4-dichlorophenyl)pyrazole-3-carboxylate Chemical compound [K+].C(#N)C=1C=NN(C=1C(=O)[O-])C1=C(C=C(C=C1)Cl)Cl QSDFADUFARKNDZ-UHFFFAOYSA-M 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([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
239000003531 protein hydrolysate Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011435 rock Substances 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003892 spreading Methods 0.000 description 1
101150035983 str1 gene Proteins 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
235000014101 wine Nutrition 0.000 description 1
239000002023 wood Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

Classifications

- 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
- 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
- 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
- C07D231/16—Halogen atoms or nitro radicals

Landscapes

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

DD86296291A 1985-11-18 1986-11-14 Herbizide mittel DD253937A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853540839 DE3540839A1 (de)	1985-11-18	1985-11-18	1-aryl-pyrazole

Publications (1)

Publication Number	Publication Date
DD253937A5 true DD253937A5 (de)	1988-02-10

Family

ID=6286277

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86296291A DD253937A5 (de)	1985-11-18	1986-11-14	Herbizide mittel

Country Status (11)

Country	Link
EP (1)	EP0224094A3 (da)
JP (1)	JPS62120369A (da)
KR (1)	KR870004963A (da)
AU (1)	AU586903B2 (da)
BR (1)	BR8605675A (da)
DD (1)	DD253937A5 (da)
DE (1)	DE3540839A1 (da)
DK (1)	DK548486A (da)
HU (1)	HUT44129A (da)
IL (1)	IL80645A0 (da)
ZA (1)	ZA868686B (da)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8713769D0 (en) *	1987-06-12	1987-07-15	May & Baker Ltd	Compositions of matter
JPS6425763A (en) *	1987-04-24	1989-01-27	Mitsubishi Chem Ind	Pyrazoles and insecticide and acaricide containing said pyrazoles as active ingredient
JPS6456663A (en) *	1987-08-26	1989-03-03	Otsuka Chemical Co Ltd	Pyrazole derivative and herbicide containing said derivative as active ingredient
JP2743473B2 (ja) *	1988-07-04	1998-04-22	日産化学工業株式会社	ピラゾールカルボン酸類の製造方法
JPH0812653A (ja) *	1994-04-26	1996-01-16	Nissan Chem Ind Ltd	カルボン酸オキシムエステル誘導体および農園芸用殺菌剤
JP3726306B2 (ja) *	1994-04-27	2005-12-14	日産化学工業株式会社	ピラゾールカルボン酸誘導体および植物病害防除剤
DE19520613A1 (de) *	1995-06-06	1996-12-12	Bayer Ag	Phenylpyridazinone
US5998424A (en)	1997-06-19	1999-12-07	Dupont Pharmaceuticals Company	Inhibitors of factor Xa with a neutral P1 specificity group
HRP980334A2 (en) *	1997-06-19	1999-04-30	Mimi Lifen Quan	INHIBITORS OF FACTOR Xa WITH A NEUTRAL P1 SPECIFICITY GROUP

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1229095B (de) *	1964-01-02	1966-11-24	Basf Ag	Verfahren zur Herstellung von substituierten 4-Nitro-pyrazol-5-carbonsaeuren
DE2212080A1 (de) *	1971-03-15	1972-10-12	Eli Lilly and Co., Indianapolis, Ind. (V.StA.)	3-Nitropyrazolderivate
AU508225B2 (en) *	1976-01-14	1980-03-13	Commonwealth Scientific And Industrial Research Organisation	Pyrazole fungicides
US4134987A (en) *	1976-01-14	1979-01-16	Huppatz John L	Compounds and compositions
US4282361A (en) *	1978-03-16	1981-08-04	Massachusetts Institute Of Technology	Synthesis for 7-alkylamino-3-methylpyrazolo [4,3-d]pyrimidines
IL73418A (en) *	1983-11-07	1988-02-29	Lilly Co Eli	5-cyano-1h-pyrazole-4-(thio)carboxamide derivatives,their preparation and herbicidal compositions containing them
DE3509567A1 (de) *	1985-03-16	1986-09-18	Bayer Ag, 5090 Leverkusen	Herbizide und insektizide mittel auf basis von pyrazolderivaten

1985
- 1985-11-18 DE DE19853540839 patent/DE3540839A1/de not_active Withdrawn
1986
- 1986-11-07 EP EP86115457A patent/EP0224094A3/de not_active Withdrawn
- 1986-11-14 DD DD86296291A patent/DD253937A5/de unknown
- 1986-11-14 IL IL80645A patent/IL80645A0/xx unknown
- 1986-11-17 JP JP61272025A patent/JPS62120369A/ja active Pending
- 1986-11-17 DK DK548486A patent/DK548486A/da not_active Application Discontinuation
- 1986-11-17 HU HU864738A patent/HUT44129A/hu unknown
- 1986-11-17 BR BR8605675A patent/BR8605675A/pt unknown
- 1986-11-17 ZA ZA868686A patent/ZA868686B/xx unknown
- 1986-11-18 AU AU65507/86A patent/AU586903B2/en not_active Ceased
- 1986-11-18 KR KR860009734A patent/KR870004963A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
HUT44129A (en)	1988-02-29
ZA868686B (en)	1987-07-29
EP0224094A3 (de)	1988-11-30
DK548486A (da)	1987-05-19
JPS62120369A (ja)	1987-06-01
AU6550786A (en)	1987-05-21
DK548486D0 (da)	1986-11-17
IL80645A0 (en)	1987-02-27
EP0224094A2 (de)	1987-06-03
KR870004963A (ko)	1987-06-02
DE3540839A1 (de)	1987-05-27
AU586903B2 (en)	1989-07-27
BR8605675A (pt)	1987-08-18

Publication	Publication Date	Title
EP0154115B1 (de)	1988-10-26	Herbizide Mittel auf Basis von Pyrazolderivaten
EP0232538B1 (de)	1990-05-23	5-Acylamido-1-aryl-pyrazole
EP0248315A2 (de)	1987-12-09	5-Acylamino-pyrazol-Derivate
EP0207285A1 (de)	1987-01-07	5-Amino-1-pyridyl-pyrazole
DE4021439A1 (de)	1991-06-20	2-iminopyridin-derivate
EP0138149B1 (de)	1989-01-18	Substituierte 5-Acylamino-1-phenylpyrazole
EP0257296B1 (de)	1993-05-12	4-Cyano(nitro)-5-oxy(thio)-pyrazol-Derivate
DD260431A5 (de)	1988-09-28	Herbizide und pflanzenwuchsregulierende mittel
DD258559A5 (de)	1988-07-27	Herbizide und pflanzenwuchsregulierende mittel
DE3726919A1 (de)	1989-02-23	1-arylpyrazole
EP0242573A1 (de)	1987-10-28	5-Acylamino-pyrazol-Derivate
EP0224094A2 (de)	1987-06-03	1-Aryl-pyrazole
EP0191282B1 (de)	1989-10-04	1-Aryl-4-Nitropyrazole
EP0173821B1 (de)	1989-01-18	Substituierte 5-Amino-1-phenylpyrazole
EP0171544B1 (de)	1989-01-04	Substituierte 5-Acylamino-1-phenylpyrazole
DD256639A5 (de)	1988-05-18	Herbizide und pflanzenwuchsregulierende mittel
EP0222253B1 (de)	1989-04-05	Substituierte 5-Amino-1-aryl-pyrazole
EP0204242A2 (de)	1986-12-10	1-Aryl-4-cyano-5-halogenpyrazole
DE3637710A1 (de)	1988-05-11	5-acylamino-pyrazol-derivate
DD256640A5 (de)	1988-05-18	Herbizide und pflanzenwuchsregulierende mittel
DD258558A5 (de)	1988-07-27	1-aryl-5-hydrazino-pyrazole
DE3707686A1 (de)	1988-09-22	4-cyano-1-aryl-pyrazole
EP0192951A2 (de)	1986-09-03	5-Sulfonamido-1-aryl-pyrazole