CA1078850A - Sels de diphenylpyrazolium servant d'herbicides et de fongicides - Google Patents
Sels de diphenylpyrazolium servant d'herbicides et de fongicidesInfo
- Publication number
- CA1078850A CA1078850A CA250,620A CA250620A CA1078850A CA 1078850 A CA1078850 A CA 1078850A CA 250620 A CA250620 A CA 250620A CA 1078850 A CA1078850 A CA 1078850A
- Authority
- CA
- Canada
- Prior art keywords
- dimethyl
- diphenyl
- compound
- diphenylpyrazolium
- perchlorate
- 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.)
- Expired
Links
- 239000004009 herbicide Substances 0.000 title description 8
- 239000000417 fungicide Substances 0.000 title description 2
- LQUBXCVRJZGBLM-UHFFFAOYSA-O 2,5-diphenyl-1h-pyrazol-2-ium Chemical class C1=CC(C=2C=CC=CC=2)=N[NH+]1C1=CC=CC=C1 LQUBXCVRJZGBLM-UHFFFAOYSA-O 0.000 title 1
- 241000196324 Embryophyta Species 0.000 claims abstract description 35
- -1 carbethoxymethyl Chemical group 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 18
- 150000001450 anions Chemical class 0.000 claims abstract description 10
- 241000233866 Fungi Species 0.000 claims abstract description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000007921 spray Substances 0.000 claims description 14
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 12
- 239000002689 soil Substances 0.000 claims description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 4
- OCXWPNUZUDNOAK-UHFFFAOYSA-N 1,2-dimethyl-3,5-diphenyl-4-propylpyrazol-1-ium Chemical compound CN1[N+](C)=C(C=2C=CC=CC=2)C(CCC)=C1C1=CC=CC=C1 OCXWPNUZUDNOAK-UHFFFAOYSA-N 0.000 claims description 3
- GSOOPJTXVXTDSC-UHFFFAOYSA-N 4-benzyl-1,2-dimethyl-3,5-diphenylpyrazol-1-ium Chemical compound C=1C=CC=CC=1C1=[N+](C)N(C)C(C=2C=CC=CC=2)=C1CC1=CC=CC=C1 GSOOPJTXVXTDSC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 3
- 241000894007 species Species 0.000 claims description 3
- WECVTOUWBRBXCE-UHFFFAOYSA-N 1,2,4-trimethyl-3,5-diphenylpyrazol-1-ium Chemical group CN1[N+](C)=C(C=2C=CC=CC=2)C(C)=C1C1=CC=CC=C1 WECVTOUWBRBXCE-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 6
- PKWSFZHMPNCCFO-UHFFFAOYSA-M 4-ethyl-1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(CC)=C1C1=CC=CC=C1 PKWSFZHMPNCCFO-UHFFFAOYSA-M 0.000 claims 4
- QDDRDURSDCEBKI-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenyl-4-propylpyrazol-1-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(CCC)=C1C1=CC=CC=C1 QDDRDURSDCEBKI-UHFFFAOYSA-M 0.000 claims 3
- NJEWCCAOEKSKET-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenyl-4-prop-2-ynylpyrazol-1-ium;hydron;sulfate Chemical compound OS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=C(CC#C)C=1C1=CC=CC=C1 NJEWCCAOEKSKET-UHFFFAOYSA-M 0.000 claims 2
- SFJCOYWIITVQKO-UHFFFAOYSA-M 1,2-dimethyl-4-pentyl-3,5-diphenylpyrazol-1-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CN1[N+](C)=C(C=2C=CC=CC=2)C(CCCCC)=C1C1=CC=CC=C1 SFJCOYWIITVQKO-UHFFFAOYSA-M 0.000 claims 2
- ZOMSORPENUNIFS-UHFFFAOYSA-M 4-benzyl-1,2-dimethyl-3,5-diphenylpyrazol-1-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C=1C=CC=CC=1C1=[N+](C)N(C)C(C=2C=CC=CC=2)=C1CC1=CC=CC=C1 ZOMSORPENUNIFS-UHFFFAOYSA-M 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract description 15
- 239000000203 mixture Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 230000002363 herbicidal effect Effects 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 239000004094 surface-active agent Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- 238000012360 testing method Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 244000098338 Triticum aestivum Species 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 10
- 235000008504 concentrate Nutrition 0.000 description 10
- 241000221785 Erysiphales Species 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 235000007320 Avena fatua Nutrition 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- 125000005594 diketone group Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- 241000220225 Malus Species 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 244000075850 Avena orientalis Species 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- 235000013350 formula milk Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 240000006122 Chenopodium album Species 0.000 description 5
- 235000009344 Chenopodium album Nutrition 0.000 description 5
- 244000152970 Digitaria sanguinalis Species 0.000 description 5
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 4
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 4
- 235000005476 Digitaria cruciata Nutrition 0.000 description 4
- 235000006830 Digitaria didactyla Nutrition 0.000 description 4
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 4
- 235000014716 Eleusine indica Nutrition 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 3
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 206010039509 Scab Diseases 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 238000005956 quaternization reaction Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000004135 Amaranthus viridis Nutrition 0.000 description 2
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 2
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- 244000024671 Brassica kaber Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 240000001549 Ipomoea eriocarpa Species 0.000 description 2
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 2
- 235000003403 Limnocharis flava Nutrition 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000220324 Pyrus Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 235000003484 annual ragweed Nutrition 0.000 description 2
- 235000021016 apples Nutrition 0.000 description 2
- 229940076134 benzene Drugs 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 235000006263 bur ragweed Nutrition 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 235000003488 common ragweed Nutrition 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 230000036244 malformation Effects 0.000 description 2
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- 238000007363 ring formation reaction Methods 0.000 description 2
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- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- AMANBMHGZZGKKL-UHFFFAOYSA-M 1,2,4-trimethyl-3,5-diphenylpyrazol-1-ium;iodide Chemical compound [I-].CN1[N+](C)=C(C=2C=CC=CC=2)C(C)=C1C1=CC=CC=C1 AMANBMHGZZGKKL-UHFFFAOYSA-M 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LOERFLXCAOUXBR-UHFFFAOYSA-N 1,4-dimethyl-3,5-diphenylpyrazole Chemical compound CC=1C(C=2C=CC=CC=2)=NN(C)C=1C1=CC=CC=C1 LOERFLXCAOUXBR-UHFFFAOYSA-N 0.000 description 1
- JHTKOUJDEUQFOB-UHFFFAOYSA-N 1h-pyrazol-1-ium;chloride Chemical compound Cl.C=1C=NNC=1 JHTKOUJDEUQFOB-UHFFFAOYSA-N 0.000 description 1
- LAVLWJYYMDUIEJ-UHFFFAOYSA-O 1h-pyrazol-1-ium;nitrate Chemical compound [O-][N+]([O-])=O.C1=CN[NH+]=C1 LAVLWJYYMDUIEJ-UHFFFAOYSA-O 0.000 description 1
- KWORYKSPKDSKKG-UHFFFAOYSA-N 2-(2-adamantyl)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine Chemical compound C1C(CC2C3)CC3CC1C2N1CC2CCCN2CC1 KWORYKSPKDSKKG-UHFFFAOYSA-N 0.000 description 1
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- JPKIVCQXKRSNGY-UHFFFAOYSA-N 3,5-dicyclohexyl-1,4-dimethylpyrazole Chemical compound CC=1C(C2CCCCC2)=NN(C)C=1C1CCCCC1 JPKIVCQXKRSNGY-UHFFFAOYSA-N 0.000 description 1
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- 239000005909 Kieselgur Substances 0.000 description 1
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ICIHDUSPYJNBRL-UHFFFAOYSA-N methyl sulfate;1h-pyrazol-1-ium Chemical compound [NH2+]1C=CC=N1.COS([O-])(=O)=O ICIHDUSPYJNBRL-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/784—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with all keto groups bound to a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
- C07C49/796—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/04—Sodium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/574,068 US4017298A (en) | 1975-05-02 | 1975-05-02 | 1,2,4-Trialkyl-3,5-diphenylpyrazolium salts as herbicides |
| US05/574,067 US3958001A (en) | 1975-05-02 | 1975-05-02 | 4-Alkyl-1,2-dimethyl-3,5-diphenylpyrazolium salts and derivatives thereof as fungicidal agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1078850A true CA1078850A (fr) | 1980-06-03 |
Family
ID=27076277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA250,620A Expired CA1078850A (fr) | 1975-05-02 | 1976-04-21 | Sels de diphenylpyrazolium servant d'herbicides et de fongicides |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS51133265A (fr) |
| AR (1) | AR217400A1 (fr) |
| AU (1) | AU503523B2 (fr) |
| CA (1) | CA1078850A (fr) |
| CS (1) | CS191170B2 (fr) |
| DD (1) | DD127656A5 (fr) |
| DE (1) | DE2618421A1 (fr) |
| DK (1) | DK194476A (fr) |
| ES (1) | ES447515A1 (fr) |
| FI (1) | FI761159A (fr) |
| FR (1) | FR2309539A1 (fr) |
| GB (1) | GB1543338A (fr) |
| IL (1) | IL49410A (fr) |
| IT (1) | IT1060500B (fr) |
| NL (1) | NL7604597A (fr) |
| PL (1) | PL107282B1 (fr) |
| SE (1) | SE7605011L (fr) |
| SU (1) | SU683601A3 (fr) |
| TR (1) | TR18655A (fr) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3818096A (en) * | 1972-04-12 | 1974-06-18 | Schering Corp | Compositions of 1,2-dilower alkyl arylpyrazolium quaternary salts and method of lowering blood sugar levels with same |
| DE2404795C2 (de) * | 1974-02-01 | 1983-03-24 | Basf Ag, 6700 Ludwigshafen | 1,2-Dimethyl-3,5-diphenyl-pyrazoliumsalze und deren Verwendung als Herbizid |
| DE2524853A1 (de) * | 1975-06-04 | 1976-12-09 | Vulkan Werk Gmbh | Verfahren und vorrichtung zur herstellung von masten, insbesondere beleuchtungsmasten |
-
1976
- 1976-04-13 IL IL49410A patent/IL49410A/xx unknown
- 1976-04-14 AU AU12987/76A patent/AU503523B2/en not_active Expired
- 1976-04-21 CA CA250,620A patent/CA1078850A/fr not_active Expired
- 1976-04-22 AR AR262970A patent/AR217400A1/es active
- 1976-04-22 GB GB16439/76A patent/GB1543338A/en not_active Expired
- 1976-04-27 DE DE19762618421 patent/DE2618421A1/de not_active Withdrawn
- 1976-04-27 FI FI761159A patent/FI761159A/fi not_active Application Discontinuation
- 1976-04-29 NL NL7604597A patent/NL7604597A/xx not_active Application Discontinuation
- 1976-04-29 FR FR7612809A patent/FR2309539A1/fr not_active Withdrawn
- 1976-04-29 CS CS762833A patent/CS191170B2/cs unknown
- 1976-04-29 TR TR18655A patent/TR18655A/xx unknown
- 1976-04-30 ES ES447515A patent/ES447515A1/es not_active Expired
- 1976-04-30 SU SU762354750A patent/SU683601A3/ru active
- 1976-04-30 SE SE7605011A patent/SE7605011L/xx unknown
- 1976-04-30 IT IT49288/76A patent/IT1060500B/it active
- 1976-04-30 DK DK194476A patent/DK194476A/da unknown
- 1976-04-30 DD DD192622A patent/DD127656A5/xx unknown
- 1976-04-30 PL PL1976189201A patent/PL107282B1/pl unknown
- 1976-05-04 JP JP51050052A patent/JPS51133265A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES447515A1 (es) | 1977-11-01 |
| JPS51133265A (en) | 1976-11-18 |
| IL49410A (en) | 1980-06-30 |
| GB1543338A (en) | 1979-04-04 |
| AR217400A1 (es) | 1980-03-31 |
| NL7604597A (nl) | 1976-11-04 |
| PL107282B1 (pl) | 1980-02-29 |
| AU503523B2 (en) | 1979-09-06 |
| CS191170B2 (en) | 1979-06-29 |
| IL49410A0 (en) | 1976-06-30 |
| SU683601A3 (ru) | 1979-08-30 |
| TR18655A (tr) | 1977-06-23 |
| AU1298776A (en) | 1977-10-20 |
| SE7605011L (sv) | 1976-11-03 |
| DK194476A (da) | 1976-11-03 |
| IT1060500B (it) | 1982-08-20 |
| DE2618421A1 (de) | 1976-11-18 |
| FR2309539A1 (fr) | 1976-11-26 |
| FI761159A (fr) | 1976-11-03 |
| DD127656A5 (fr) | 1977-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |