DD254127A5 - Herbizide mittel - Google Patents

Herbizide mittel Download PDF

Info

Publication number: DD254127A5
Authority: DD; German Democratic Republic
Prior art keywords: chlorine; fluorine; methyl; carbon atoms; formula
Prior art date: 1985-12-13

Application number

DD86297455A

Other languages

German (de)

English (en)

Inventor

Klaus Sasse

Hermann Hagemann

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.)

1985-12-13

Filing date

1986-12-11

Publication date

1988-02-17

1986-12-11 Application filed by ��@��k�� filed Critical ��@��k��

1988-02-17 Publication of DD254127A5 publication Critical patent/DD254127A5/de

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230000002363 herbicidal effect Effects 0.000 title claims abstract description 10
239000004009 herbicide Substances 0.000 title description 8
239000000203 mixture Substances 0.000 claims abstract description 24
239000000460 chlorine Substances 0.000 claims description 70
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 45
229910052801 chlorine Inorganic materials 0.000 claims description 45
239000011737 fluorine Substances 0.000 claims description 45
229910052731 fluorine Inorganic materials 0.000 claims description 45
125000004432 carbon atom Chemical group C* 0.000 claims description 43
-1 methyl-substituted phenyl Chemical group 0.000 claims description 36
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 26
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 24
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
229910052794 bromium Inorganic materials 0.000 claims description 23
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 21
125000001153 fluoro group Chemical group F* 0.000 claims description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
229920006395 saturated elastomer Polymers 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
125000006413 ring segment Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000000547 substituted alkyl group Chemical group 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
239000004606 Fillers/Extenders Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
239000013543 active substance Substances 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 10
238000000034 method Methods 0.000 description 69
150000001875 compounds Chemical class 0.000 description 36
239000002253 acid Substances 0.000 description 32
239000003085 diluting agent Substances 0.000 description 29
241000196324 Embryophyta Species 0.000 description 26
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 20
239000011230 binding agent Substances 0.000 description 18
239000007858 starting material Substances 0.000 description 17
239000000126 substance Substances 0.000 description 17
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
150000003254 radicals Chemical class 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
150000003230 pyrimidines Chemical class 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
239000002904 solvent Substances 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 8
238000007796 conventional method Methods 0.000 description 7
238000009472 formulation Methods 0.000 description 7
150000004820 halides Chemical class 0.000 description 7
238000010626 work up procedure Methods 0.000 description 7
WCDSVWRUXWCYFN-UHFFFAOYSA-N 4-aminobenzenethiol Chemical class NC1=CC=C(S)C=C1 WCDSVWRUXWCYFN-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000008065 acid anhydrides Chemical class 0.000 description 6
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 6
239000008187 granular material Substances 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000002689 soil Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000000370 acceptor Substances 0.000 description 4
150000001448 anilines Chemical class 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000002798 polar solvent Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000009467 reduction Effects 0.000 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 3
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 3
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 3
239000000292 calcium oxide Substances 0.000 description 3
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000000417 fungicide Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
VFZRGLKTZAKXCP-UHFFFAOYSA-N 2-(4-nitrophenyl)sulfanylpyrimidine Chemical class C1=CC([N+](=O)[O-])=CC=C1SC1=NC=CC=N1 VFZRGLKTZAKXCP-UHFFFAOYSA-N 0.000 description 2
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
OOZUHSZMAPAATM-UHFFFAOYSA-N 4,5-dimethyl-2-(4-nitrophenyl)sulfanylpyrimidine Chemical compound N1=C(C)C(C)=CN=C1SC1=CC=C([N+]([O-])=O)C=C1 OOZUHSZMAPAATM-UHFFFAOYSA-N 0.000 description 2
ASZGGIFGRFMKAF-UHFFFAOYSA-N 4,6-dimethyl-2-phenoxypyrimidine Chemical compound CC1=CC(C)=NC(OC=2C=CC=CC=2)=N1 ASZGGIFGRFMKAF-UHFFFAOYSA-N 0.000 description 2
ZRDZPYPHXPJTAE-UHFFFAOYSA-N 4-(4,5-dimethylpyrimidin-2-yl)sulfanylaniline Chemical compound N1=C(C)C(C)=CN=C1SC1=CC=C(N)C=C1 ZRDZPYPHXPJTAE-UHFFFAOYSA-N 0.000 description 2
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 2
241000219318 Amaranthus Species 0.000 description 2
235000005781 Avena Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
241000219312 Chenopodium Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 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
235000021506 Ipomoea Nutrition 0.000 description 2
241000207783 Ipomoea Species 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
241000209094 Oryza Species 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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
235000005775 Setaria Nutrition 0.000 description 2
241000232088 Setaria <nematode> Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
229910000272 alkali metal oxide Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000002877 alkyl aryl group Chemical group 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 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
150000004678 hydrides Chemical class 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000395 magnesium oxide Substances 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
150000002736 metal compounds Chemical class 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
150000002825 nitriles Chemical class 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
239000006072 paste Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
238000005507 spraying Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
150000008319 1H-pyrimidin-2-ones Chemical class 0.000 description 1
BQHWATVEWGHHHF-UHFFFAOYSA-N 2,2-dimethyl-3-phenylpropanoic acid Chemical compound OC(=O)C(C)(C)CC1=CC=CC=C1 BQHWATVEWGHHHF-UHFFFAOYSA-N 0.000 description 1
GIROESBYMDYHRL-UHFFFAOYSA-N 2,2-dimethyl-n-(4-sulfanylphenyl)propanamide Chemical compound CC(C)(C)C(=O)NC1=CC=C(S)C=C1 GIROESBYMDYHRL-UHFFFAOYSA-N 0.000 description 1
FEDNFSGWMHEOQS-UHFFFAOYSA-N 2,2-dimethylpropanoic acid;2-methylbutanoic acid Chemical compound CCC(C)C(O)=O.CC(C)(C)C(O)=O FEDNFSGWMHEOQS-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
RUQQKYAEQGBNCT-UHFFFAOYSA-N 2,5-dichloro-4,6-dimethylpyrimidine Chemical compound CC1=NC(Cl)=NC(C)=C1Cl RUQQKYAEQGBNCT-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
GFKKWENTMDBEPJ-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)-2-methylpropanoic acid Chemical compound CC1=CC(Cl)=CC=C1OC(C)(C)C(O)=O GFKKWENTMDBEPJ-UHFFFAOYSA-N 0.000 description 1
WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
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WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [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 description 1
239000004579 marble Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
230000003641 microbiacidal effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
UAHGAVXIGCZBAC-UHFFFAOYSA-N n-[4-(4,5-dimethylpyrimidin-2-yl)sulfanylphenyl]-2,2-dimethylpropanamide Chemical compound N1=C(C)C(C)=CN=C1SC1=CC=C(NC(=O)C(C)(C)C)C=C1 UAHGAVXIGCZBAC-UHFFFAOYSA-N 0.000 description 1
229940042880 natural phospholipid Drugs 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052755 nonmetal Chemical class 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 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
235000019260 propionic acid Nutrition 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
230000007065 protein hydrolysis Effects 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
235000009566 rice Nutrition 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
238000009331 sowing Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
230000009885 systemic effect Effects 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
150000003512 tertiary amines Chemical class 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
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
238000005406 washing Methods 0.000 description 1
235000014101 wine Nutrition 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

DD86297455A 1985-12-13 1986-12-11 Herbizide mittel DD254127A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853544208 DE3544208A1 (de)	1985-12-13	1985-12-13	Pyrimidylmercapto-acylanilide

Publications (1)

Publication Number	Publication Date
DD254127A5 true DD254127A5 (de)	1988-02-17

Family

ID=6288412

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86297455A DD254127A5 (de)	1985-12-13	1986-12-11	Herbizide mittel

Country Status (12)

Country	Link
US (1)	US4797146A (da)
EP (1)	EP0226885A1 (da)
JP (1)	JPS62145071A (da)
KR (1)	KR870006014A (da)
AU (1)	AU587516B2 (da)
BR (1)	BR8606196A (da)
DD (1)	DD254127A5 (da)
DE (1)	DE3544208A1 (da)
DK (1)	DK599586A (da)
HU (1)	HU198026B (da)
IL (2)	IL80930A0 (da)
ZA (1)	ZA869375B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8823288D0 (en) *	1988-10-04	1988-11-09	Schering Agrochemicals Ltd	Herbicides

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3931201A (en) *	1974-01-22	1976-01-06	The Dow Chemical Company	Substituted pyridinyloxy(thio)phenyl -acetamides, -ureas and urea derivatives
DD109170A1 (da) *	1974-01-24	1974-10-20
DE3422077A1 (de) *	1984-06-14	1985-12-19	Bayer Ag, 5090 Leverkusen	Substituierte carbonsaeureanilide

1985
- 1985-12-13 DE DE19853544208 patent/DE3544208A1/de not_active Withdrawn
1986
- 1986-12-01 EP EP86116656A patent/EP0226885A1/de not_active Withdrawn
- 1986-12-04 US US06/937,940 patent/US4797146A/en not_active Expired - Fee Related
- 1986-12-10 IL IL80930A patent/IL80930A0/xx unknown
- 1986-12-10 IL IL80929A patent/IL80929A0/xx unknown
- 1986-12-11 JP JP61293564A patent/JPS62145071A/ja active Pending
- 1986-12-11 DD DD86297455A patent/DD254127A5/de unknown
- 1986-12-12 KR KR860010611A patent/KR870006014A/ko not_active Withdrawn
- 1986-12-12 ZA ZA869375A patent/ZA869375B/xx unknown
- 1986-12-12 HU HU865192A patent/HU198026B/hu not_active IP Right Cessation
- 1986-12-12 DK DK599586A patent/DK599586A/da not_active Application Discontinuation
- 1986-12-15 BR BR8606196A patent/BR8606196A/pt unknown
- 1986-12-15 AU AU66563/86A patent/AU587516B2/en not_active Ceased

Also Published As

Publication number	Publication date
DE3544208A1 (de)	1987-06-19
HUT43048A (en)	1987-09-28
IL80930A0 (en)	1987-03-31
US4797146A (en)	1989-01-10
KR870006014A (ko)	1987-07-08
AU6656386A (en)	1987-06-18
BR8606196A (pt)	1987-09-29
DK599586A (da)	1987-06-14
DK599586D0 (da)	1986-12-12
AU587516B2 (en)	1989-08-17
ZA869375B (en)	1987-09-30
JPS62145071A (ja)	1987-06-29
HU198026B (en)	1989-07-28
EP0226885A1 (de)	1987-07-01
IL80929A0 (en)	1987-03-31

Publication	Publication Date	Title
EP0354329B1 (de)	1993-02-10	(Hetero)Aryloxynaphthaline mit über Schwefel gebundenen Substituenten
EP0302312A2 (de)	1989-02-08	Neue Aryloxy (bzw. thio)-aminopyrimidine
EP0256396A1 (de)	1988-02-24	Triazolo-pyrimidin-2-sulfonamide
EP0451585A2 (de)	1991-10-16	2-Aryl-6-hetarylpyridin-Derivate
EP0168608A2 (de)	1986-01-22	Substituierte Carbonsäureanilide
DE3633485A1 (de)	1988-04-07	Substituierte 2-pyri(mi)dyl-2'-pyridyl-(thio)-ether
EP0173320A1 (de)	1986-03-05	Substituierte Carbonylphenylsulfonylguanidine
EP0173319A1 (de)	1986-03-05	Substituierte Arylsulfonylguanidine
DD238319A5 (de)	1986-08-20	Herbizide mittel
EP0243868A2 (de)	1987-11-04	Pyridylthio-acylanilide
US4797146A (en)	1989-01-10	Herbicidal 2-[4-substituted carboxyamino-phenyl mercapto)]-subsituted pyrimidines
EP0465901A1 (de)	1992-01-15	2-Acylamino-7-chlorbenzthiazole
EP0173323A1 (de)	1986-03-05	Amidinoazole
EP0283762A1 (de)	1988-09-28	Neue Thiazolylether- und -thioetherderivate
EP0467139A2 (de)	1992-01-22	Nicotinsäurederivate als Herbizide
DE3425123A1 (de)	1986-01-16	Optisch aktive phenoxypropionsaeure-derivate
DE3502266A1 (de)	1986-08-07	Optisch aktive phenoxypropionsaeure-derivate
DD254126A5 (de)	1988-02-17	Herbizide mittel
EP0220635A1 (de)	1987-05-06	Phenoxybenzoesäure-Derivate
DE3617715A1 (de)	1987-12-03	Oxa-bicyclo(2.2.1)hepten-derivate
DE3528099A1 (de)	1987-02-19	Benzodisultame
EP0264021A2 (de)	1988-04-20	0-Aryl-N'-(triazin-2-yl)-isoharnstoffe
DD237785A5 (de)	1986-07-30	Herbizide mittel
EP0257422A1 (de)	1988-03-02	Phenoxybenzoesäureester
DE3725639A1 (de)	1989-02-16	Neue aryloxy (bzw. thio)aminopyrimidine