CS240993B2 - Fungicide and bectericide agent and its effective compound production method - Google Patents
Fungicide and bectericide agent and its effective compound production method Download PDFInfo
- Publication number
- CS240993B2 CS240993B2 CS84663A CS66384A CS240993B2 CS 240993 B2 CS240993 B2 CS 240993B2 CS 84663 A CS84663 A CS 84663A CS 66384 A CS66384 A CS 66384A CS 240993 B2 CS240993 B2 CS 240993B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- formula
- carbon atoms
- active ingredient
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 63
- 230000000855 fungicidal effect Effects 0.000 title claims description 13
- 239000003795 chemical substances by application Substances 0.000 title description 8
- 239000000417 fungicide Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 49
- 239000004480 active ingredient Substances 0.000 claims description 37
- -1 hydroxylamino group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 230000000844 anti-bacterial effect Effects 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 241001611408 Nebo Species 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 16
- 239000000839 emulsion Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 230000012010 growth Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- 241000233866 Fungi Species 0.000 description 8
- 239000005995 Aluminium silicate Substances 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 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 6
- 239000007788 liquid Substances 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 206010061217 Infestation Diseases 0.000 description 4
- 241000233622 Phytophthora infestans Species 0.000 description 4
- 241000233639 Pythium Species 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 235000019993 champagne Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 102100033849 CCHC-type zinc finger nucleic acid binding protein Human genes 0.000 description 3
- 101710116319 CCHC-type zinc finger nucleic acid binding protein Proteins 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 241001123569 Puccinia recondita Species 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical group 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229940064002 calcium hypophosphite Drugs 0.000 description 2
- 229910001382 calcium hypophosphite Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 2
- 239000004550 soluble concentrate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- CNALVHVMBXLLIY-IUCAKERBSA-N tert-butyl n-[(3s,5s)-5-methylpiperidin-3-yl]carbamate Chemical compound C[C@@H]1CNC[C@@H](NC(=O)OC(C)(C)C)C1 CNALVHVMBXLLIY-IUCAKERBSA-N 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- 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
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- SOYUQCONIJBZDL-UHFFFAOYSA-N 1-hydroxyethyl dihydrogen phosphite Chemical compound CC(O)OP(O)O SOYUQCONIJBZDL-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- ACBPPDYBJZVCTL-UHFFFAOYSA-N CCP(O)=O Chemical compound CCP(O)=O ACBPPDYBJZVCTL-UHFFFAOYSA-N 0.000 description 1
- SKASAEJUDUNQFF-UHFFFAOYSA-M C[S+](C)(C)=O.[O-]P(=O)C1=CC=CC=C1 Chemical compound C[S+](C)(C)=O.[O-]P(=O)C1=CC=CC=C1 SKASAEJUDUNQFF-UHFFFAOYSA-M 0.000 description 1
- 235000010523 Cicer arietinum Nutrition 0.000 description 1
- 244000045195 Cicer arietinum Species 0.000 description 1
- 241000186216 Corynebacterium Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 241000588698 Erwinia Species 0.000 description 1
- 241000588694 Erwinia amylovora Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 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
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- 241000589652 Xanthomonas oryzae Species 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- NQQFJSVHPWZWMS-UHFFFAOYSA-N ethyl phosphite;trimethylsulfanium Chemical compound C[S+](C)C.C[S+](C)C.CCOP([O-])[O-] NQQFJSVHPWZWMS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- ARENMZZMCSLORU-UHFFFAOYSA-N propan-2-yl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OC(C)C)=CC=CC2=C1 ARENMZZMCSLORU-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- RABUZJZUBFMWSH-UHFFFAOYSA-N sulfane;hydroiodide Chemical class [SH3+].[I-] RABUZJZUBFMWSH-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- MJZACYWTDBYPTO-UHFFFAOYSA-L trimethylsulfanium;sulfate Chemical compound C[S+](C)C.C[S+](C)C.[O-]S([O-])(=O)=O MJZACYWTDBYPTO-UHFFFAOYSA-L 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-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
- 238000004017 vitrification Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/142—Esters of phosphorous acids with hydroxyalkyl compounds without further substituents on alkyl
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8301727A FR2540120B1 (fr) | 1983-02-01 | 1983-02-01 | Sels de derives organophosphores fongicides |
| FR8316499A FR2553419B1 (fr) | 1983-10-13 | 1983-10-13 | Sels de derives organophosphores fongicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS66384A2 CS66384A2 (en) | 1985-06-13 |
| CS240993B2 true CS240993B2 (en) | 1986-03-13 |
Family
ID=26223269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS84663A CS240993B2 (en) | 1983-02-01 | 1984-01-30 | Fungicide and bectericide agent and its effective compound production method |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4542023A (da) |
| EP (1) | EP0115466B1 (da) |
| KR (1) | KR890005170B1 (da) |
| AU (1) | AU568834B2 (da) |
| BR (1) | BR8400348A (da) |
| CA (1) | CA1240337A (da) |
| CS (1) | CS240993B2 (da) |
| DD (1) | DD220219A5 (da) |
| DE (1) | DE3464253D1 (da) |
| DK (1) | DK164157C (da) |
| ES (2) | ES8503355A1 (da) |
| GR (1) | GR81683B (da) |
| HU (1) | HU194478B (da) |
| IE (1) | IE56785B1 (da) |
| MA (1) | MA20022A1 (da) |
| NZ (1) | NZ206967A (da) |
| OA (1) | OA07647A (da) |
| PH (1) | PH19466A (da) |
| PL (1) | PL139657B1 (da) |
| PT (1) | PT78041B (da) |
| RO (1) | RO90599B (da) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0202027A1 (en) * | 1985-04-18 | 1986-11-20 | Sumitomo Chemical Company, Limited | A herbicidal composition |
| IL82311A (en) * | 1986-05-09 | 1992-06-21 | Rhone Poulenc Agrochimie | Bactericidal compositions based on phosphorous acid derivatives |
| US4962228A (en) * | 1987-03-09 | 1990-10-09 | Mobil Oil Corporation | Layered divalent metal phosphates containing pendent substituent groups and their preparation |
| FR2655816B1 (fr) * | 1989-12-14 | 1994-04-29 | Rhone Poulenc Agrochimie | Granules dispersables de produits fongicides. |
| US5133891A (en) * | 1990-04-27 | 1992-07-28 | Rhone Poulenc Ag Co. | Treatment of plants for frost protection |
| DE4125440A1 (de) * | 1990-08-09 | 1992-02-13 | Sandoz Ag | Mono-, bi- oder tri-carbocyclische phosphin- oder phosphonsaeureverbindungen |
| GB9103260D0 (en) * | 1991-02-15 | 1991-04-03 | Ici Plc | Chemical process |
| GB9111974D0 (en) * | 1991-06-04 | 1991-07-24 | Ici Plc | Novel process |
| US5514200B1 (en) | 1994-02-07 | 1997-07-08 | Univ | Formulation of phosphorus fertilizer for plants |
| US6338860B1 (en) | 1996-08-30 | 2002-01-15 | Foliar Nutrients, Inc. | Compositions for plants containing phosphonate and phosphate salts, and derivatives thereof |
| US5736164A (en) * | 1996-08-30 | 1998-04-07 | Taylor; John B. | Fungicidal compositions for plants containing phosphonate and phosphate salts, and derivatives thereof |
| US5800837A (en) * | 1996-08-30 | 1998-09-01 | Foliar Nutrients, Inc. | Plant fertilizer compositions containing phosphonate and phosphate salts and derivatives thereof |
| AU777125B2 (en) * | 1997-09-19 | 2004-09-30 | Foliar Nutrients, Inc. | Fungicidal/fertilizer compositions for plants containing phosphonate and phosphate salts, and derivatives thereof |
| AU741341B2 (en) * | 1997-09-19 | 2001-11-29 | Foliar Nutrients, Inc. | Fungicidal compositions for plants containing phosphonate and phosphate salts, and derivatives thereof |
| TWI260673B (en) | 1999-12-03 | 2006-08-21 | Toyo Gosei Kogyo Kk | Method for producing onium salt derivatives |
| JP4856874B2 (ja) | 2002-12-04 | 2012-01-18 | 三井化学アグロ株式会社 | 麦類のマイコトキシン汚染抑制方法 |
| US20060084573A1 (en) * | 2004-10-12 | 2006-04-20 | Biagro Western Sales, Inc. | High calcium fertilizer composition |
| JP2008542170A (ja) * | 2005-05-23 | 2008-11-27 | プラント プロテクタンツ，エルエルシー | ジチオカルバメートおよびホスファイト配合物 |
| US7566807B2 (en) * | 2006-09-14 | 2009-07-28 | Novolyte Technologies Inc. | Benzene phosphinic acid with improved flowability |
| US8748345B2 (en) * | 2007-05-10 | 2014-06-10 | Tessenderlo Kerley Inc. | Method and composition for improving turfgrass |
| MX2023003726A (es) | 2020-10-02 | 2023-06-28 | Helm Ag | Cloruros de trialquilsulfonio como fungicidas. |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3507937A (en) * | 1966-10-04 | 1970-04-21 | Procter & Gamble | Reversed zwitterionic phosphorus compounds |
| US3637496A (en) * | 1966-10-25 | 1972-01-25 | Procter & Gamble | Phosphiniminosulfoxonium compounds and process for preparing the same |
| US3702878A (en) * | 1969-12-31 | 1972-11-14 | Sanko Chemical Co Ltd | Cyclic organophosphorus compounds and process for making same |
| US3711493A (en) * | 1970-02-10 | 1973-01-16 | Ici Ltd | Plant growth regulating composition |
| FR2308312A1 (fr) * | 1975-04-25 | 1976-11-19 | Philagro Sa | Compositions fongicides a base d'hypophosphites |
| FR2317286A1 (fr) * | 1975-07-11 | 1977-02-04 | Aquitaine Petrole | Nouveaux composes a fonction sulfonium et leur application, en particulier comme fongicides |
| FR2457873A1 (fr) * | 1978-03-16 | 1980-12-26 | Rhone Poulenc Agrochimie | Compositions fongicides a base de phosphites d'isothiouronium |
| US4366150A (en) * | 1979-11-29 | 1982-12-28 | Sumitomo Chemical Company, Limited | Soil disinfectants and method of use |
| EP0038778A3 (de) * | 1980-04-21 | 1981-11-25 | Ciba-Geigy Ag | Alkylphosphonite, Verfahren zu deren Herstellung sowie die Verwendung von Alkylphosphoniten als Fungizide |
| US4315765A (en) * | 1980-12-04 | 1982-02-16 | Stauffer Chemical Company | Trialkylsulfonium salts of n-phosphonomethylglycine and their use as plant growth regulators and herbicides |
-
1984
- 1984-01-17 KR KR1019840000183A patent/KR890005170B1/ko not_active IP Right Cessation
- 1984-01-23 RO RO113390A patent/RO90599B/ro unknown
- 1984-01-23 GR GR73589A patent/GR81683B/el unknown
- 1984-01-25 DE DE8484420008T patent/DE3464253D1/de not_active Expired
- 1984-01-25 EP EP84420008A patent/EP0115466B1/fr not_active Expired
- 1984-01-27 IE IE182/84A patent/IE56785B1/en not_active IP Right Cessation
- 1984-01-27 AU AU23844/84A patent/AU568834B2/en not_active Ceased
- 1984-01-27 CA CA000446167A patent/CA1240337A/en not_active Expired
- 1984-01-27 NZ NZ206967A patent/NZ206967A/en unknown
- 1984-01-27 BR BR8400348A patent/BR8400348A/pt unknown
- 1984-01-30 CS CS84663A patent/CS240993B2/cs unknown
- 1984-01-30 PL PL1984245968A patent/PL139657B1/pl unknown
- 1984-01-30 PH PH30178A patent/PH19466A/en unknown
- 1984-01-31 ES ES529299A patent/ES8503355A1/es not_active Expired
- 1984-01-31 DK DK042184A patent/DK164157C/da not_active IP Right Cessation
- 1984-01-31 HU HU84416A patent/HU194478B/hu unknown
- 1984-01-31 MA MA20244A patent/MA20022A1/fr unknown
- 1984-01-31 US US06/575,574 patent/US4542023A/en not_active Expired - Fee Related
- 1984-01-31 DD DD84259740A patent/DD220219A5/de unknown
- 1984-01-31 PT PT78041A patent/PT78041B/pt not_active IP Right Cessation
- 1984-02-01 OA OA58219A patent/OA07647A/xx unknown
- 1984-11-16 ES ES537718A patent/ES537718A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3464253D1 (en) | 1987-07-23 |
| RO90599B (ro) | 1987-02-28 |
| ES8601220A1 (es) | 1985-10-16 |
| DK164157B (da) | 1992-05-18 |
| IE840182L (en) | 1984-08-01 |
| GR81683B (da) | 1984-12-12 |
| ES529299A0 (es) | 1985-02-16 |
| ES537718A0 (es) | 1985-10-16 |
| DK164157C (da) | 1992-10-26 |
| EP0115466A3 (en) | 1984-09-05 |
| PT78041A (fr) | 1984-02-01 |
| PL139657B1 (en) | 1987-02-28 |
| MA20022A1 (fr) | 1984-10-01 |
| CA1240337A (en) | 1988-08-09 |
| HU194478B (en) | 1988-02-29 |
| PT78041B (fr) | 1986-06-02 |
| CS66384A2 (en) | 1985-06-13 |
| NZ206967A (en) | 1987-05-29 |
| PL245968A1 (en) | 1984-11-08 |
| IE56785B1 (en) | 1991-12-18 |
| KR840007596A (ko) | 1984-12-08 |
| OA07647A (fr) | 1985-05-23 |
| DK42184D0 (da) | 1984-01-31 |
| AU2384484A (en) | 1984-08-02 |
| BR8400348A (pt) | 1984-09-04 |
| ES8503355A1 (es) | 1985-02-16 |
| RO90599A (ro) | 1987-02-27 |
| AU568834B2 (en) | 1988-01-14 |
| EP0115466A2 (fr) | 1984-08-08 |
| US4542023A (en) | 1985-09-17 |
| PH19466A (en) | 1986-05-12 |
| EP0115466B1 (fr) | 1987-06-16 |
| DD220219A5 (de) | 1985-03-27 |
| KR890005170B1 (ko) | 1989-12-16 |
| DK42184A (da) | 1984-08-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS240993B2 (en) | Fungicide and bectericide agent and its effective compound production method | |
| US4041157A (en) | Fungicidal pyrimidine derivatives | |
| IL44821A (en) | Plant fungicidal and mircobicidal compositions containing certaining certain omega-imidazolyl-omega-phenoxy(or phenylthio)-alkanones | |
| US4382928A (en) | Fungicidal compositions | |
| DE2412564A1 (de) | N,n-dimethylcarbamoyl-1,2,4-triazolyl(3)-ester, verfahren zu ihrer herstellung und ihre verwendung | |
| US4297367A (en) | 2-Phenyl-4-pyrone derivatives, their preparation and their use as fungicides | |
| KR960001204B1 (ko) | N-알킬벤젠 술포닐 카르바모일-5-클로로이소티아졸 유도체 및 살미생물제 | |
| US4049801A (en) | Phosphite compounds as fungicidal agents | |
| JPH0434539B2 (da) | ||
| EP0018943A1 (de) | 1-Triazolo-N-(phenyl)-azomethin-Derivate, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Mittel und ihre Verwendung in der Schädlingsbekämpfung | |
| EP0412681B1 (en) | Azolidine derivatives, process for preparing the same and agricultural and horticultural fungicide | |
| CS196416B2 (en) | Fungicide and process for preparing effective compounds thereof | |
| GB2039487A (en) | New fungicidal derivatives of N- phenyl-N-(alkoxycarbonylalkyl) -acetamide phosphorodithioates | |
| DE2411809A1 (de) | Thiolphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung | |
| US4515807A (en) | Thioglycine derivatives and use as fungicides | |
| JP4058166B2 (ja) | 有害生物防除剤組成物および有害生物の防除方法 | |
| KR810000453B1 (ko) | 아인산히드라지늄 유도체의 제조방법 | |
| DE2365061B2 (de) | Fungizide Mittel auf der Basis von Alkylphosphit-Derivaten | |
| AU586175B2 (en) | Azolyl derivatives of carbocyclic and heterocyclic ketones having fungicidal activity | |
| US4046883A (en) | Fungicidal compositions based on polyimides of phosphorus and method of treating plants therewith | |
| KR810000200B1 (ko) | 아실화 이미다졸일-o, n-아세탈 유도체의 제조방법 | |
| SU639412A3 (ru) | Инсектицидноакарицидное средство | |
| PL90905B1 (en) | Fungicides for control of tobacco, vine and hop mildew - comprising 2-hydroxy-1,3,2-dioxaphospholone and 2-hydroxyethyl phosphonate[FR2213735A1] | |
| DE2043745A1 (de) | Organische Phosphorverbindungen, Verfahren zu ihrer Herstellung und ihre Anwendung als Insektizid | |
| CH675666A5 (da) |