DD242165A5 - Herbizide mittel - Google Patents

Herbizide mittel Download PDF

Info

Publication number: DD242165A5
Authority: DD; German Democratic Republic
Prior art keywords: ocf; formula; scf; independently; mol
Prior art date: 1985-01-17

Application number

DD86286221A

Other languages

German (de)

English (en)

Inventor

Reinhold Gehring

Otto Schallner

Joerg Stetter

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.)

1985-01-17

Filing date

1986-01-15

Publication date

1987-01-21

1986-01-15 Application filed by ��@��k�� filed Critical ��@��k��

1987-01-21 Publication of DD242165A5 publication Critical patent/DD242165A5/de

Links

239000004009 herbicide Substances 0.000 title claims description 7
230000002363 herbicidal effect Effects 0.000 title description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 19
229910052736 halogen Inorganic materials 0.000 claims abstract description 15
150000002367 halogens Chemical class 0.000 claims abstract description 15
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
241000251730 Chondrichthyes Species 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 8
125000001475 halogen functional group Chemical group 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 37
229910052739 hydrogen Inorganic materials 0.000 abstract description 10
239000001257 hydrogen Substances 0.000 abstract description 10
150000002431 hydrogen Chemical class 0.000 abstract description 9
125000004961 1-arylpyrazolyl group Chemical group 0.000 abstract description 7
125000003282 alkyl amino group Chemical group 0.000 abstract description 6
125000004663 dialkyl amino group Chemical group 0.000 abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 6
239000000460 chlorine Substances 0.000 description 445
-1 cyano, nitro, fluoro, chloro, bromo, iodo, methyl Chemical group 0.000 description 35
238000000034 method Methods 0.000 description 33
239000000203 mixture Substances 0.000 description 27
241000196324 Embryophyta Species 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
238000002360 preparation method Methods 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
239000003085 diluting agent Substances 0.000 description 16
239000002904 solvent Substances 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
239000003054 catalyst Substances 0.000 description 13
239000007858 starting material Substances 0.000 description 13
150000003254 radicals Chemical class 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
238000009472 formulation Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
230000006378 damage Effects 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
125000005843 halogen group Chemical group 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229910017604 nitric acid Inorganic materials 0.000 description 6
238000010992 reflux Methods 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
239000004606 Fillers/Extenders Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000008187 granular material Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000000843 powder Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
JWGYPTNGYXOXPV-UHFFFAOYSA-N 4-nitro-1h-pyrazol-5-amine Chemical class NC=1NN=CC=1[N+]([O-])=O JWGYPTNGYXOXPV-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
238000002955 isolation Methods 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
239000012071 phase Substances 0.000 description 4
150000004031 phenylhydrazines Chemical class 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000002689 soil Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 3
HIDGANXIXZZRKB-UHFFFAOYSA-N 5-chloro-1-(2,4,6-trichlorophenyl)pyrazole Chemical compound ClC1=CC=NN1C1=C(Cl)C=C(Cl)C=C1Cl HIDGANXIXZZRKB-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
244000038559 crop plants Species 0.000 description 3
OYCZDPPYPCQCDR-UHFFFAOYSA-N diethyl 2-[[2-(2,4,6-trichlorophenyl)hydrazinyl]methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CNNC1=C(Cl)C=C(Cl)C=C1Cl OYCZDPPYPCQCDR-UHFFFAOYSA-N 0.000 description 3
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
QSZMYDLCTFEZQD-UHFFFAOYSA-N n-[4-cyano-2-(2,3,4-trichlorophenyl)pyrazol-3-yl]propanamide Chemical compound CCC(=O)NC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl QSZMYDLCTFEZQD-UHFFFAOYSA-N 0.000 description 3
150000002826 nitrites Chemical class 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
235000009518 sodium iodide Nutrition 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
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 2
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 2
JRPJTYFPXIRFNA-UHFFFAOYSA-N 4-nitro-2-(2,4,6-trichlorophenyl)pyrazol-3-amine Chemical compound NC1=C([N+]([O-])=O)C=NN1C1=C(Cl)C=C(Cl)C=C1Cl JRPJTYFPXIRFNA-UHFFFAOYSA-N 0.000 description 2
WOZREMDJQMANJV-UHFFFAOYSA-N 4-nitro-2-[2,3,6-trichloro-4-(trifluoromethyl)phenyl]pyrazol-3-amine Chemical compound NC1=C([N+]([O-])=O)C=NN1C1=C(Cl)C=C(C(F)(F)F)C(Cl)=C1Cl WOZREMDJQMANJV-UHFFFAOYSA-N 0.000 description 2
BYCRJAIOSSGJFI-UHFFFAOYSA-N 5-chloro-4-nitro-1-(2,4,6-trichlorophenyl)pyrazole Chemical compound ClC1=C([N+](=O)[O-])C=NN1C1=C(Cl)C=C(Cl)C=C1Cl BYCRJAIOSSGJFI-UHFFFAOYSA-N 0.000 description 2
244000105624 Arachis hypogaea Species 0.000 description 2
235000005781 Avena Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
DASQIKOOFDJYKA-UHFFFAOYSA-N CCIF Chemical compound CCIF DASQIKOOFDJYKA-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
241000219146 Gossypium Species 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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
238000005684 Liebig rearrangement reaction Methods 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000209117 Panicum Species 0.000 description 2
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 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
235000021536 Sugar beet Nutrition 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
WNAGVMRWPDSQKD-UHFFFAOYSA-N [2,3,6-trichloro-4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=C(Cl)C=C(C(F)(F)F)C(Cl)=C1Cl WNAGVMRWPDSQKD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000008360 acrylonitriles Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
229950005228 bromoform Drugs 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
150000008422 chlorobenzenes Chemical class 0.000 description 2
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000006193 diazotization reaction Methods 0.000 description 2
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 2
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 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
150000002170 ethers Chemical class 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N ethylene glycol dimethyl ether Natural products COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000006396 nitration reaction Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
239000006072 paste Substances 0.000 description 2
239000003444 phase transfer catalyst Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
238000005507 spraying Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
125000006337 tetrafluoro ethyl group Chemical group 0.000 description 2
125000006000 trichloroethyl group Chemical group 0.000 description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
MULHANRBCQBHII-UHFFFAOYSA-N (2,4,6-trichlorophenyl)hydrazine Chemical compound NNC1=C(Cl)C=C(Cl)C=C1Cl MULHANRBCQBHII-UHFFFAOYSA-N 0.000 description 1
XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 1
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
LGEAVJHSPOTSRR-UHFFFAOYSA-N 1-amino-3-(2,2-dimethylpropyl)-5-ethylsulfanyl-1,3,5-triazinane-2,4-dione Chemical compound NN1C(N(C(N(C1)SCC)=O)CC(C)(C)C)=O LGEAVJHSPOTSRR-UHFFFAOYSA-N 0.000 description 1
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 1
OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
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238000000746 purification Methods 0.000 description 1
150000003219 pyrazolines Chemical class 0.000 description 1
239000010453 quartz Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000011435 rock Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000010288 sodium nitrite 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
235000011150 stannous chloride Nutrition 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
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
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 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
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
XKFPGUWSSPXXMF-UHFFFAOYSA-N tributyl(methyl)phosphanium Chemical compound CCCC[P+](C)(CCCC)CCCC XKFPGUWSSPXXMF-UHFFFAOYSA-N 0.000 description 1
125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
235000014101 wine Nutrition 0.000 description 1
239000002023 wood Substances 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
- C07D231/14—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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD86286221A 1985-01-17 1986-01-15 Herbizide mittel DD242165A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853501323 DE3501323A1 (de)	1985-01-17	1985-01-17	1-aryl-4-nitropyrazole

Publications (1)

Publication Number	Publication Date
DD242165A5 true DD242165A5 (de)	1987-01-21

Family

ID=6260002

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86286221A DD242165A5 (de)	1985-01-17	1986-01-15	Herbizide mittel

Country Status (15)

Country	Link
US (2)	US4681618A (es)
EP (1)	EP0191282B1 (es)
JP (1)	JPS61167664A (es)
AT (1)	ATE46901T1 (es)
AU (1)	AU580373B2 (es)
BR (1)	BR8600171A (es)
DD (1)	DD242165A5 (es)
DE (2)	DE3501323A1 (es)
DK (1)	DK20586A (es)
ES (3)	ES8707716A1 (es)
GR (1)	GR860090B (es)
HU (1)	HU197496B (es)
NZ (1)	NZ214824A (es)
TR (1)	TR22331A (es)
ZA (1)	ZA86328B (es)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3447211A1 (de) *	1984-12-22	1986-06-26	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von substituierten phenylhydrazinen
DE3509567A1 (de) *	1985-03-16	1986-09-18	Bayer Ag, 5090 Leverkusen	Herbizide und insektizide mittel auf basis von pyrazolderivaten
GB8713769D0 (en) *	1987-06-12	1987-07-15	May & Baker Ltd	Compositions of matter
DE3628892A1 (de) *	1986-08-26	1988-03-10	Bayer Ag	Substituierte 1-aryl-3-tert.-butyl-pyrazole
DE3808896A1 (de) *	1988-03-17	1989-09-28	Hoechst Ag	Pflanzenschuetzende mittel auf basis von pyrazolcarbonsaeurederivaten
EP0366329B1 (en) *	1988-10-27	1996-03-20	Nissan Chemical Industries, Limited	Halogeno-4-methylpyrazoles and process for preparing the same
US6906006B1 (en)	1988-11-23	2005-06-14	Bayer Aktiengesellschaft	N-arly-substituted nitrogen-containing heterocycles, processes and novel intermediates for their preparation, and their use as herbicides and plant growth regulators
DE3839480A1 (de) *	1988-11-23	1990-05-31	Bayer Ag	N-aryl-stickstoffheterocyclen, verfahren sowie neue zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwuchsregulatoren
US5018661A (en) *	1988-11-25	1991-05-28	Cyb Frederick F	Heat-resistant exhaust manifold and method of preparing same

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH573919A5 (en) *	1971-10-22	1976-03-31	Hoffmann La Roche	4-nitropyrazole-5-carboxamidines and 4-nitropyrazole-5-yl - 1,2,4-oxadiazoles - with psychosedative, analgesic and muscle relaxan
US3869274A (en) *	1972-08-21	1975-03-04	Abbott Lab	Method and composition for inducing fruit abscission
US4025530A (en) *	1974-05-02	1977-05-24	Abbott Laboratories	4-Nitropyrazoles
DE3509567A1 (de) *	1985-03-16	1986-09-18	Bayer Ag, 5090 Leverkusen	Herbizide und insektizide mittel auf basis von pyrazolderivaten

1985
- 1985-01-17 DE DE19853501323 patent/DE3501323A1/de not_active Withdrawn
1986
- 1986-01-06 US US06/816,643 patent/US4681618A/en not_active Expired - Fee Related
- 1986-01-07 EP EP86100093A patent/EP0191282B1/de not_active Expired
- 1986-01-07 AT AT86100093T patent/ATE46901T1/de not_active IP Right Cessation
- 1986-01-07 DE DE8686100093T patent/DE3666038D1/de not_active Expired
- 1986-01-09 AU AU52160/86A patent/AU580373B2/en not_active Ceased
- 1986-01-14 NZ NZ214824A patent/NZ214824A/xx unknown
- 1986-01-15 GR GR860090A patent/GR860090B/el unknown
- 1986-01-15 DD DD86286221A patent/DD242165A5/de not_active IP Right Cessation
- 1986-01-16 HU HU86229A patent/HU197496B/hu not_active IP Right Cessation
- 1986-01-16 ZA ZA86328A patent/ZA86328B/xx unknown
- 1986-01-16 JP JP61005154A patent/JPS61167664A/ja active Pending
- 1986-01-16 BR BR8600171A patent/BR8600171A/pt unknown
- 1986-01-16 DK DK20586A patent/DK20586A/da unknown
- 1986-01-16 TR TR2415/86A patent/TR22331A/xx unknown
- 1986-01-17 ES ES550993A patent/ES8707716A1/es not_active Expired
1987
- 1987-02-19 US US07/016,599 patent/US4758673A/en not_active Expired - Fee Related
- 1987-04-29 ES ES557512A patent/ES8802499A1/es not_active Expired
- 1987-04-29 ES ES557513A patent/ES8802302A1/es not_active Expired

Also Published As

Publication number	Publication date
GR860090B (en)	1986-05-16
TR22331A (tr)	1987-02-13
DK20586D0 (da)	1986-01-16
ES557512A0 (es)	1988-07-01
DK20586A (da)	1986-07-18
US4681618A (en)	1987-07-21
ES550993A0 (es)	1987-08-16
DE3666038D1 (de)	1989-11-09
EP0191282B1 (de)	1989-10-04
ES557513A0 (es)	1988-05-01
AU5216086A (en)	1986-07-24
DE3501323A1 (de)	1986-07-17
BR8600171A (pt)	1986-09-30
JPS61167664A (ja)	1986-07-29
ES8707716A1 (es)	1987-08-16
HU197496B (en)	1989-04-28
NZ214824A (en)	1989-02-24
US4758673A (en)	1988-07-19
HUT42277A (en)	1987-07-28
ZA86328B (en)	1986-09-24
AU580373B2 (en)	1989-01-12
ATE46901T1 (de)	1989-10-15
EP0191282A1 (de)	1986-08-20
ES8802499A1 (es)	1988-07-01
ES8802302A1 (es)	1988-05-01

Legal Events

Date	Code	Title	Description
1994-01-27	PJ	Ceased due to non-payment of renewal fee (addendum to changes before extension act)

Publication	Publication Date	Title
EP0232538B1 (de)	1990-05-23	5-Acylamido-1-aryl-pyrazole
EP0154115B1 (de)	1988-10-26	Herbizide Mittel auf Basis von Pyrazolderivaten
EP0207285A1 (de)	1987-01-07	5-Amino-1-pyridyl-pyrazole
EP0138149B1 (de)	1989-01-18	Substituierte 5-Acylamino-1-phenylpyrazole
EP0257296B1 (de)	1993-05-12	4-Cyano(nitro)-5-oxy(thio)-pyrazol-Derivate
DE3617977A1 (de)	1987-06-11	5-dichloracetamido-4-nitro-1-aryl-pyrazole
DD260431A5 (de)	1988-09-28	Herbizide und pflanzenwuchsregulierende mittel
DD258559A5 (de)	1988-07-27	Herbizide und pflanzenwuchsregulierende mittel
EP0191282B1 (de)	1989-10-04	1-Aryl-4-Nitropyrazole
EP0303153A2 (de)	1989-02-15	1-Arylpyrazole
EP0242573A1 (de)	1987-10-28	5-Acylamino-pyrazol-Derivate
EP0173821B1 (de)	1989-01-18	Substituierte 5-Amino-1-phenylpyrazole
EP0171544B1 (de)	1989-01-04	Substituierte 5-Acylamino-1-phenylpyrazole
EP0204242A2 (de)	1986-12-10	1-Aryl-4-cyano-5-halogenpyrazole
DD253937A5 (de)	1988-02-10	Herbizide mittel
EP0222253B1 (de)	1989-04-05	Substituierte 5-Amino-1-aryl-pyrazole
DD256639A5 (de)	1988-05-18	Herbizide und pflanzenwuchsregulierende mittel
DD256640A5 (de)	1988-05-18	Herbizide und pflanzenwuchsregulierende mittel
EP0269839A1 (de)	1988-06-08	5-Acylamino-pyrazol-Derivate
EP0212353A2 (de)	1987-03-04	1- Aryl-5-hydrazino-pyrazole
DE3707686A1 (de)	1988-09-22	4-cyano-1-aryl-pyrazole
EP0205023A2 (de)	1986-12-17	1-Aryl-4-heterocyclyl-pyrazole
EP0192951A2 (de)	1986-09-03	5-Sulfonamido-1-aryl-pyrazole
EP0297427A2 (de)	1989-01-04	1-Arylpyrazole