DE2046646A1 - Pyndazin cycloalkylether und ein Verfahren zu deren Herstellung - Google Patents
Pyndazin cycloalkylether und ein Verfahren zu deren HerstellungInfo
- Publication number
- DE2046646A1 DE2046646A1 DE19702046646 DE2046646A DE2046646A1 DE 2046646 A1 DE2046646 A1 DE 2046646A1 DE 19702046646 DE19702046646 DE 19702046646 DE 2046646 A DE2046646 A DE 2046646A DE 2046646 A1 DE2046646 A1 DE 2046646A1
- Authority
- DE
- Germany
- Prior art keywords
- pyridazine
- methylcyclohexyloxy
- dimethylcyclohexyloxy
- parts
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 cycloalkyl ethers Chemical class 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- 241000196324 Embryophyta Species 0.000 claims description 17
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- QHFXKRMMBQGBDA-UHFFFAOYSA-N 3-cyclohexyloxypyridazine Chemical compound C1(CCCCC1)OC=1N=NC=CC1 QHFXKRMMBQGBDA-UHFFFAOYSA-N 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical class ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 description 11
- 240000008042 Zea mays Species 0.000 description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 8
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 241001666377 Apera Species 0.000 description 5
- 244000058871 Echinochloa crus-galli Species 0.000 description 5
- 235000011999 Panicum crusgalli Nutrition 0.000 description 5
- 244000062793 Sorghum vulgare Species 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- 235000019713 millet Nutrition 0.000 description 5
- 235000007319 Avena orientalis Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- 241000209504 Poaceae Species 0.000 description 4
- 235000007238 Secale cereale Nutrition 0.000 description 4
- 244000082988 Secale cereale Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- NDVWOBYBJYUSMF-UHFFFAOYSA-N 2-methylcyclohexan-1-ol Chemical compound CC1CCCCC1O NDVWOBYBJYUSMF-UHFFFAOYSA-N 0.000 description 3
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- 244000152970 Digitaria sanguinalis Species 0.000 description 3
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- HTSABYAWKQAHBT-UHFFFAOYSA-N 3-methylcyclohexanol Chemical compound CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 244000070788 Milium effusum Species 0.000 description 2
- 235000007199 Panicum miliaceum Nutrition 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000004892 pyridazines Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MOISVRZIQDQVPF-RNLVFQAGSA-N (rac)-2,6-dimethylcyclohexanol Natural products C[C@@H]1CCC[C@H](C)[C@@H]1O MOISVRZIQDQVPF-RNLVFQAGSA-N 0.000 description 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
- ZSLKGUQYEQVKQE-UHFFFAOYSA-N 1-prop-2-enylcyclohexan-1-ol Chemical compound C=CCC1(O)CCCCC1 ZSLKGUQYEQVKQE-UHFFFAOYSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
- RUADGOLRFXTMCY-UHFFFAOYSA-N 2,5-dimethylcyclohexan-1-ol Chemical compound CC1CCC(C)C(O)C1 RUADGOLRFXTMCY-UHFFFAOYSA-N 0.000 description 1
- MOISVRZIQDQVPF-UHFFFAOYSA-N 2,6-dimethylcyclohexan-1-ol Chemical compound CC1CCCC(C)C1O MOISVRZIQDQVPF-UHFFFAOYSA-N 0.000 description 1
- QPKJFOGPKCJHME-UHFFFAOYSA-N 2-(6-chloropyridazin-3-yl)oxyacetic acid Chemical compound OC(=O)COC1=CC=C(Cl)N=N1 QPKJFOGPKCJHME-UHFFFAOYSA-N 0.000 description 1
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
- VZBNUCDUQJCIDP-UHFFFAOYSA-N 2-propylcyclohexan-1-ol Chemical compound CCCC1CCCCC1O VZBNUCDUQJCIDP-UHFFFAOYSA-N 0.000 description 1
- ZBAXJUPCYVIBSP-UHFFFAOYSA-N 3,4-Dimethylcyclohexanol Chemical compound CC1CCC(O)CC1C ZBAXJUPCYVIBSP-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- WIYNOPYNRFPWNB-UHFFFAOYSA-N 3,5-Dimethylcyclohexanol Chemical compound CC1CC(C)CC(O)C1 WIYNOPYNRFPWNB-UHFFFAOYSA-N 0.000 description 1
- OJQAWSGLUDQRGU-UHFFFAOYSA-N 3-chloro-6-cyclohexyloxypyridazine Chemical compound N1=NC(Cl)=CC=C1OC1CCCCC1 OJQAWSGLUDQRGU-UHFFFAOYSA-N 0.000 description 1
- FTXJUKILOHPHHB-UHFFFAOYSA-N 3-phenoxypyridazine Chemical compound C=1C=CN=NC=1OC1=CC=CC=C1 FTXJUKILOHPHHB-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 235000005474 African couch grass Nutrition 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 244000078127 Eleusine coracana Species 0.000 description 1
- 235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 1
- 241001520106 Eustachys Species 0.000 description 1
- 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 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- JXUFFXNMFZOVDU-UHFFFAOYSA-N N1=CN=CN=C1.[Cl] Chemical class N1=CN=CN=C1.[Cl] JXUFFXNMFZOVDU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000006597 Poa trivialis Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical class O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 244000037666 field crops Species 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 210000001699 lower leg Anatomy 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 239000012749 thinning agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
- C07D237/14—Oxygen atoms
-
- 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
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material 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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT836670A AT303050B (de) | 1970-09-16 | 1970-09-16 | Verfahren zur Herstellung von neuen Puridazin-cycloalkyl-äthern |
| AT836770A AT304927B (de) | 1970-09-16 | 1970-09-16 | Herbizides Mittel |
| DE19702046646 DE2046646A1 (de) | 1970-09-16 | 1970-09-22 | Pyndazin cycloalkylether und ein Verfahren zu deren Herstellung |
| GB4042171A GB1354169A (en) | 1970-09-16 | 1971-08-27 | Pyridazine derivatives and the preparation thereof |
| ZA715831A ZA715831B (en) | 1970-09-16 | 1971-08-31 | Pyridazine derivatives and the preparation thereof |
| IT69994/71A IT942455B (it) | 1970-09-16 | 1971-09-09 | Cicloalchiletere di piridazina e procedimento per la sua produzio ne |
| FR7132897A FR2107591A5 (enExample) | 1970-09-16 | 1971-09-13 | |
| RO68206A RO58975A (enExample) | 1970-09-16 | 1971-09-14 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT836670A AT303050B (de) | 1970-09-16 | 1970-09-16 | Verfahren zur Herstellung von neuen Puridazin-cycloalkyl-äthern |
| AT836770A AT304927B (de) | 1970-09-16 | 1970-09-16 | Herbizides Mittel |
| DE19702046646 DE2046646A1 (de) | 1970-09-16 | 1970-09-22 | Pyndazin cycloalkylether und ein Verfahren zu deren Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2046646A1 true DE2046646A1 (de) | 1972-03-23 |
Family
ID=27150978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702046646 Pending DE2046646A1 (de) | 1970-09-16 | 1970-09-22 | Pyndazin cycloalkylether und ein Verfahren zu deren Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| AT (2) | AT303050B (enExample) |
| DE (1) | DE2046646A1 (enExample) |
| FR (1) | FR2107591A5 (enExample) |
| GB (1) | GB1354169A (enExample) |
| IT (1) | IT942455B (enExample) |
| RO (1) | RO58975A (enExample) |
| ZA (1) | ZA715831B (enExample) |
-
1970
- 1970-09-16 AT AT836670A patent/AT303050B/de not_active IP Right Cessation
- 1970-09-16 AT AT836770A patent/AT304927B/de not_active IP Right Cessation
- 1970-09-22 DE DE19702046646 patent/DE2046646A1/de active Pending
-
1971
- 1971-08-27 GB GB4042171A patent/GB1354169A/en not_active Expired
- 1971-08-31 ZA ZA715831A patent/ZA715831B/xx unknown
- 1971-09-09 IT IT69994/71A patent/IT942455B/it active
- 1971-09-13 FR FR7132897A patent/FR2107591A5/fr not_active Expired
- 1971-09-14 RO RO68206A patent/RO58975A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT942455B (it) | 1973-03-20 |
| ZA715831B (en) | 1973-04-25 |
| GB1354169A (en) | 1974-06-05 |
| AT303050B (de) | 1972-11-10 |
| AT304927B (de) | 1973-01-25 |
| RO58975A (enExample) | 1975-12-15 |
| FR2107591A5 (enExample) | 1972-05-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1770269C3 (de) | Imidazol-Derivate und herbizide Mittel | |
| EP0003805A1 (de) | Pyridazonverbindungen und diese enthaltende herbizide Zusammensetzungen | |
| DE3107629C2 (de) | 2-Cyan-2-phenylacetamide und diese enthaltende pflanzenwachstumsregulierende Mittel | |
| CH666890A5 (de) | 2-(1-(3-chlorallyloxyamino)-alkyliden)-5-alkylthioalkyl-cyclohexan-1,3-dion. | |
| DE2532767A1 (de) | Triazin-derivate als schaedlingsbekaempfungsmittel | |
| EP0259265B1 (de) | 3-Methylphthalimide | |
| DE2210540C2 (de) | Cyanphenylcarbonate, Verfahren zu deren Herstellung sowie diese enthaltende herbizide Mittel | |
| DE3226009A1 (de) | Als unkrautvernichtungs- und pflanzenwachstumsregulierungsmittel geeignete 2,4-hexadiensaeurederivate | |
| DE2524578A1 (de) | Barbitursaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide | |
| DE2046646A1 (de) | Pyndazin cycloalkylether und ein Verfahren zu deren Herstellung | |
| DE1914012A1 (de) | Neue s-Triazin-Derivate | |
| DE2302029C2 (de) | N,N-disubstituierte &alpha;-Aminothiopropionsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2945388A1 (de) | N-(phenylcycloalkyl)-acetamide | |
| DE2163381A1 (de) | Herbizide Komposition | |
| EP0071572A2 (de) | Derivate der 2-Nitro-4- oder 5-Pyridyloxy-phenylphosphonsäure, Verfahren zu ihrer Herstellung, ihre Verwendung als Herbizide und/oder Pflanzenwachstumsregulatoren und/oder Mikrobizide, sowie zur Herstellung der Derivate verwendete Zwischenprodukte, Verfahren zu deren Herstellung und deren Verwendung als Herbizide | |
| DE3300154A1 (de) | Harnstoff derivate | |
| DD264843A5 (de) | Herbizide mittel | |
| DE4011781A1 (de) | Herbizides mittel | |
| EP0020437B1 (de) | Halogenacetanilide, ihre Herstellung und diese enthaltende Herbizide | |
| DE2551983A1 (de) | Pyrazolidine und verfahren zu ihrer herstellung | |
| EP0016731B1 (de) | Meta-Cyanoalkoxy-Phenylharnstoffe mit herbizider Wirkung, deren Herstellung und sie enthaltende Mittel | |
| DE2514992A1 (de) | Fungizide mittel | |
| DE2230076A1 (de) | Verfahren zur Herstellung neuer heterocyclischer Stoffe | |
| EP0024016A1 (de) | Tetrachlorphthalamidsäuren, Verfahren zu ihrer Herstellung und ihre bakterizide Verwendung | |
| CH421136A (de) | Verfahren zur Herstellung von Verbindungen zur Bekämpfung von Schädlingen |