DE2014061A1 - Fungizide Mittel - Google Patents
Fungizide MittelInfo
- Publication number
- DE2014061A1 DE2014061A1 DE19702014061 DE2014061A DE2014061A1 DE 2014061 A1 DE2014061 A1 DE 2014061A1 DE 19702014061 DE19702014061 DE 19702014061 DE 2014061 A DE2014061 A DE 2014061A DE 2014061 A1 DE2014061 A1 DE 2014061A1
- Authority
- DE
- Germany
- Prior art keywords
- phosphonic acid
- lower alkyl
- mixture
- copper
- contain
- 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
- 239000000417 fungicide Substances 0.000 title claims description 7
- -1 dithiol phosphonic acid ester Chemical class 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical class SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- FUWGSUOSJRCEIV-UHFFFAOYSA-N phosphonothioic O,O-acid Chemical compound OP(O)=S FUWGSUOSJRCEIV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 35
- 150000001875 compounds Chemical class 0.000 description 9
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000012990 dithiocarbamate Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229960002447 thiram Drugs 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 229940096825 phenylmercury Drugs 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 5
- CAQHPYSDQFDJAL-UHFFFAOYSA-N C1=CC=C2C(=NO)C(=O)C=CC2=C1 Chemical compound C1=CC=C2C(=NO)C(=O)C=CC2=C1 CAQHPYSDQFDJAL-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 239000005843 Thiram Substances 0.000 description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 229920001021 polysulfide Polymers 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SSPLMQDYLIKKJS-UHFFFAOYSA-M ClC1=C(C=CC=C1)O.O[Hg] Chemical compound ClC1=C(C=CC=C1)O.O[Hg] SSPLMQDYLIKKJS-UHFFFAOYSA-M 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241000209094 Oryza Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- PJDVOLYULHZZAG-UHFFFAOYSA-N ethylmercury Chemical compound CC[Hg] PJDVOLYULHZZAG-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- UNQDVBLGFWIFGX-UHFFFAOYSA-M (carbamoylamino)-phenylmercury Chemical compound NC(=O)N[Hg]C1=CC=CC=C1 UNQDVBLGFWIFGX-UHFFFAOYSA-M 0.000 description 2
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004135 Bone phosphate Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 239000005752 Copper oxychloride Substances 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 241000221662 Sclerotinia Species 0.000 description 2
- IRESGOUEJVVVSQ-UHFFFAOYSA-M [Hg]O.OC1=CC=CC=C1[N+]([O-])=O Chemical compound [Hg]O.OC1=CC=CC=C1[N+]([O-])=O IRESGOUEJVVVSQ-UHFFFAOYSA-M 0.000 description 2
- 239000011717 all-trans-retinol Substances 0.000 description 2
- 235000019169 all-trans-retinol Nutrition 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 2
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 2
- MZGNSEAPZQGJRB-UHFFFAOYSA-N dimethyldithiocarbamic acid Chemical compound CN(C)C(S)=S MZGNSEAPZQGJRB-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 2
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 2
- UYJUZNLFJAWNEZ-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2NC3=CC=CC=C3N=2)=C1 UYJUZNLFJAWNEZ-UHFFFAOYSA-N 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
- 229920000940 maneb Polymers 0.000 description 2
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 2
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical group CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 2
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- DCNLOVYDMCVNRZ-UHFFFAOYSA-N phenylmercury(.) Chemical compound [Hg]C1=CC=CC=C1 DCNLOVYDMCVNRZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 2
- MRUMAIRJPMUAPZ-UHFFFAOYSA-N quinolin-8-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CN=C2C(O)=CC=CC2=C1 MRUMAIRJPMUAPZ-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ZFLCCXRFJQBTMQ-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl)methyl acetate Chemical compound CC(=O)OCC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl ZFLCCXRFJQBTMQ-UHFFFAOYSA-N 0.000 description 1
- YQRBOMYQIMHOLM-UHFFFAOYSA-M (2-hydroxybenzoyl)oxy-phenylmercury Chemical compound OC1=CC=CC=C1C(=O)O[Hg]C1=CC=CC=C1 YQRBOMYQIMHOLM-UHFFFAOYSA-M 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- YGKOYVNJPRSSRX-UHFFFAOYSA-M (4-dodecylphenyl)methyl-trimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC1=CC=C(C[N+](C)(C)C)C=C1 YGKOYVNJPRSSRX-UHFFFAOYSA-M 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZQHJVIHCDHJVII-UPHRSURJSA-N (z)-2-chlorobut-2-enedioic acid Chemical compound OC(=O)\C=C(/Cl)C(O)=O ZQHJVIHCDHJVII-UPHRSURJSA-N 0.000 description 1
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 description 1
- HILAYQUKKYWPJW-UHFFFAOYSA-N 1-dodecylguanidine Chemical compound CCCCCCCCCCCCN=C(N)N HILAYQUKKYWPJW-UHFFFAOYSA-N 0.000 description 1
- VOHCMATXIKWIKC-UHFFFAOYSA-N 1-hydroxypyridine-2-thione;zinc Chemical compound [Zn].ON1C=CC=CC1=S VOHCMATXIKWIKC-UHFFFAOYSA-N 0.000 description 1
- XFFTWZZGUGZURK-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzaldehyde Chemical compound ClC1=C(Cl)C(Cl)=C(C=O)C(Cl)=C1Cl XFFTWZZGUGZURK-UHFFFAOYSA-N 0.000 description 1
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
- KVJOLVBEUYUHLD-UHFFFAOYSA-M 2,3-dihydroxypropylsulfanyl(ethyl)mercury Chemical compound CC[Hg]SCC(O)CO KVJOLVBEUYUHLD-UHFFFAOYSA-M 0.000 description 1
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- 238000012512 characterization method Methods 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
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- VCDISIZZXHJJES-UHFFFAOYSA-N chloro hypochlorite copper 5,10-dioxobenzo[g][1,4]benzodithiine-2,3-dicarbonitrile Chemical compound [Cu].ClOCl.S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O VCDISIZZXHJJES-UHFFFAOYSA-N 0.000 description 1
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 description 1
- VJTAZCKMHINUKO-UHFFFAOYSA-M chloro(2-methoxyethyl)mercury Chemical compound [Cl-].COCC[Hg+] VJTAZCKMHINUKO-UHFFFAOYSA-M 0.000 description 1
- PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
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- 229910000009 copper(II) carbonate Inorganic materials 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- SVOAENZIOKPANY-CVBJKYQLSA-L copper;(z)-octadec-9-enoate Chemical compound [Cu+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O SVOAENZIOKPANY-CVBJKYQLSA-L 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- XAYKMDWIDMODML-UHFFFAOYSA-L copper;zinc;carbonate Chemical compound [Cu+2].[Zn].[O-]C([O-])=O XAYKMDWIDMODML-UHFFFAOYSA-L 0.000 description 1
- DCLHJMYSBFUUQV-UHFFFAOYSA-J copper;zinc;disulfate Chemical class [Cu+2].[Zn+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DCLHJMYSBFUUQV-UHFFFAOYSA-J 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000019854 cupric carbonate Nutrition 0.000 description 1
- 239000011646 cupric carbonate Substances 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 1
- 229940061632 dehydroacetic acid Drugs 0.000 description 1
- 235000019258 dehydroacetic acid Nutrition 0.000 description 1
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 description 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 1
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
- OISMQLUZKQIKII-UHFFFAOYSA-L dichlorocadmium;hydrate Chemical compound O.[Cl-].[Cl-].[Cd+2] OISMQLUZKQIKII-UHFFFAOYSA-L 0.000 description 1
- 229960003887 dichlorophen Drugs 0.000 description 1
- PNKGIAQRMACYGQ-UHFFFAOYSA-N dicopper;dizinc;chromium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Cr+3].[Cr+3].[Cu+2].[Cu+2].[Zn+2].[Zn+2] PNKGIAQRMACYGQ-UHFFFAOYSA-N 0.000 description 1
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- 239000003085 diluting agent Substances 0.000 description 1
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- 239000012895 dilution Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- CDMADVZSLOHIFP-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane;decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 CDMADVZSLOHIFP-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
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- CZZAFXTWKPQSML-UHFFFAOYSA-N ethoxy(ethyl)mercury Chemical compound CCO[Hg]CC CZZAFXTWKPQSML-UHFFFAOYSA-N 0.000 description 1
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- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019285 ethoxyquin Nutrition 0.000 description 1
- VUFOSBDICLTFMS-UHFFFAOYSA-M ethyl-hexadecyl-dimethylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)CC VUFOSBDICLTFMS-UHFFFAOYSA-M 0.000 description 1
- QWUGXIXRFGEYBD-UHFFFAOYSA-M ethylmercuric chloride Chemical compound CC[Hg]Cl QWUGXIXRFGEYBD-UHFFFAOYSA-M 0.000 description 1
- HXQVQGWHFRNKMS-UHFFFAOYSA-M ethylmercurithiosalicylic acid Chemical compound CC[Hg]SC1=CC=CC=C1C(O)=O HXQVQGWHFRNKMS-UHFFFAOYSA-M 0.000 description 1
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- WHDGWKAJBYRJJL-UHFFFAOYSA-K ferbam Chemical compound [Fe+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S WHDGWKAJBYRJJL-UHFFFAOYSA-K 0.000 description 1
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- FIVPIPIDMRVLAY-RBJBARPLSA-N gliotoxin Chemical compound C1C2=CC=C[C@H](O)[C@H]2N2[C@]1(SS1)C(=O)N(C)[C@@]1(CO)C2=O FIVPIPIDMRVLAY-RBJBARPLSA-N 0.000 description 1
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- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 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 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- UWRBYRMOUPAKLM-UHFFFAOYSA-L lead arsenate Chemical compound [Pb+2].O[As]([O-])([O-])=O UWRBYRMOUPAKLM-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- VHWYCFISAQVCCP-UHFFFAOYSA-N methoxymethanol Chemical compound COCO VHWYCFISAQVCCP-UHFFFAOYSA-N 0.000 description 1
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- 229920000257 metiram Polymers 0.000 description 1
- ORLIFVYIUIQGOA-UHFFFAOYSA-N n'-(4-nitrosophenyl)benzohydrazide Chemical compound C1=CC(N=O)=CC=C1NNC(=O)C1=CC=CC=C1 ORLIFVYIUIQGOA-UHFFFAOYSA-N 0.000 description 1
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- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 1
- 229960000625 oxytetracycline Drugs 0.000 description 1
- 235000019366 oxytetracycline Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OOCYPIXCHKROMD-UHFFFAOYSA-M phenyl(propanoyloxy)mercury Chemical compound CCC(=O)O[Hg]C1=CC=CC=C1 OOCYPIXCHKROMD-UHFFFAOYSA-M 0.000 description 1
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- XEBWQGVWTUSTLN-UHFFFAOYSA-M phenylmercury acetate Chemical compound CC(=O)O[Hg]C1=CC=CC=C1 XEBWQGVWTUSTLN-UHFFFAOYSA-M 0.000 description 1
- BISBXZWWFIOZSX-UHFFFAOYSA-M phenylmercury(1+);iodide Chemical compound I[Hg]C1=CC=CC=C1 BISBXZWWFIOZSX-UHFFFAOYSA-M 0.000 description 1
- MSYUMXXVCSLXMR-UHFFFAOYSA-N phenylmercury;hydrate Chemical compound O.[Hg]C1=CC=CC=C1 MSYUMXXVCSLXMR-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- AHIHJODVQGBOND-UHFFFAOYSA-M propan-2-yl carbonate Chemical compound CC(C)OC([O-])=O AHIHJODVQGBOND-UHFFFAOYSA-M 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- MHKFWKVLUPCEAH-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 MHKFWKVLUPCEAH-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229950000975 salicylanilide Drugs 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- CTPKSRZFJSJGML-UHFFFAOYSA-N sulfiram Chemical compound CCN(CC)C(=S)SC(=S)N(CC)CC CTPKSRZFJSJGML-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- NFMWFGXCDDYTEG-UHFFFAOYSA-N trimagnesium;diborate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]B([O-])[O-].[O-]B([O-])[O-] NFMWFGXCDDYTEG-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4087—Esters with arylalkanols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
CIBA AKTIENGESELLSCHAFT, BASEL (SCHWEIZ)
Case 6712/E
Fungizide Mittel
Die vorliegende Erfindung betrifft fungizide Mittel, welche als aktive Komponente mindestens einen
Phosphonsäureester der allgemeinen Formel
009841/1977
(Ro )n
(I)
enthalten, worin X ein Sauerstoff- oder Schwefelatom, R einen gegebenenfalls substituierten niederen Alkyl-
oder Aralkylrest, R„ und R.. Wasserstoff oder einen der
folgenden Substituenten bedeuten: einen niederen Alkylrest,
eine Nitrogruppe oder eine Trifluormethylgruppe, eine Cyanogruppe, ein Halogenatom, und η und m die Zahlen
1 oder 2 bedeuten, sowie ausserdem gegebenenfalls noch einen oder mehrere der folgenden Zusätze: Lösungs-, Verdünnungs-,
Dispergier-, Emulgier-, Haft-, Verdickungs-, Düngemittel, sowie ausserdem noch weitere bekannte
Schädlingsbekämpfungsmittel.
Bevorzugt sind jene Verbindungen der Formel I, in denen R-, einen niederen Alkylrest und X Sauerstoff bedeutet.
Die 'Wirkstoffe der Formel (i) wirken sehr gut
gegen Vertreter der Klasse· Phycomycetes, z.B. phytopathogene Pilze wie Botrytis und Piricularia, aber auch gegen verschiedene
andere pilzliche Krankheitserreger an Getreide,
Q098U / 1 977
20U061
Mais, Reis, Gemüse, Obstbau- und anderen Kulturen.
Eine besondere Wirkung besitzen sie gegen folgende
Pilzarten: Cochliobolus miyabeanus-Arten, Corticlum-Arten,
Cerospora-Arten, Altemaria-Arten, Venturia inaequalis,
Podosphaera Leucotrieha, Uromyces phasebli, Cercospora apii,
Cercospora beticola, Cereospora musae, Piricularia sp.,
Erysiphe cichoracearum, Penicillium digitatum, Sphaerotheca
humuli, Diplocarpon rosae, Uncinula necator, Coccomyces hiemalis, Cladosporium carpophilum, Erysiphe graminis hor.dei,
Monolinia "(Sclerotinia) Laxa, Monolinia (Sclerotinia) fructicola,
Piriculari-a' oryzae, Puccinia recondita, P. coronata,
P.glumarum, Puecinia graminis tritici, Aspergillus niger,
Aspergillus terreus, Rhizoctonia, Fusarium, Verticilliura,
Diese Aufzählung erhebt keinen Anspruch auf Vollständig· - '
keit.
Die erfindungsgemässen Wirkstoffe bzw. ■* Mittel
zeigen ebenfalls eine toxische Wirkung auf solche Pilze, die ^die Pflanze im Erdreich angreifen und teilweise Tracheomycosen
verursachen, wie Fusarium cubense, Fusarium dianthi, Verticillium alboatrum und Phialophora cinerecens.
Sie lassen sich nach den bekannten Methoden zur Herstellung von Phosphorsäureestern gewinnen, z.B. durch
Reaktion eines Mols eines Alkan-(thio)-phosphonsäuredi-
00 98A 1 / 1 97 7
20H061
χ
halogenids R1 - P(HaI)2 (HaI=Cl oder Br) mit 2 Molen
halogenids R1 - P(HaI)2 (HaI=Cl oder Br) mit 2 Molen
eines gegebenenfalls kernsubstituierten Benzylmercaptans in Gegenwart eines säurebindenden Mittels, wie Triäthylamin,
Alkalicarbonat, Alkalilauge oder Alkalialkoholat. Sollen
Phosphonsäureester mit verschiedenartig substituierten Benzylresten erhalten werden, setzt man das Alkan(thio)-phosphonsäuredihalogenid
nacheinander mit je einem Mol des jeweiligen Benzylmercaptans um. Die exotherme Reaktion wird
vorzugsweise unter leichter Kühlung durchgeführt.
26,6 Teile Methanphosphonsäuredichlorid und 49,6
Teile Benzylmercaptan werden in 500 Volumteilen trockenem Benzol vorgelegt. Man lässt bei 5-15°C 42 Teile Triäthylamin
zutropfen und rührt die Mischung anschliessend noch über Nacht bei Raumtemperatur. Dann wird das Chlorhydrat
mit zweimal je 100 Teilen Wasser ausgewaschen und die organische Phase nacheinander mit je 50 Volumteilen 1 n-Natronlauge
und Wasser ausgeschüttelt. Nach dem Abdampfen des Lösungsmittels erhält man als Rückstand 52,3 Teile der
Verbindung der Formel
009841/1977
20Ί4061
I!
Verbindung Nr. 1
In analoger Weise wie beschrieben kann man die Verbindung der Formel ·
CH3-P (-SCH2
Verbindung Nr. 2 herstellen, sowie die Verbindungen:
8841/1977
Verb.Nr.
Formel
-P(S-CH,
Phyeikal.Charakteri
sierung
1,6648
Il
Cl3C-P(S-CH2-^ >)2
njp 1,7023
O
Cl-CH2-P(S-CH2
1,6932
CH-P-(SCH2
1,6311
i SoCxH -P(SCHo-<f
. nD 23 1,6105
0 sch~-«3
11/ C- 1,6259
10
CF,
n/
ρ ti —ρ
2 5 \
Cl 1,5488
nD 23 1,6175
11
Il
Gl
1,6423
OO 9 8 41 /1377
Verb. Nr.
Formel Physikal.Charakterisierung
12..
CH-P(SGH2
η f 1,6388
13
CH-P(SCH2
CN).
.rar 1,63«"
14 CH-P(SCH.
1,6099
15
)o Smp.: 85-90c
16
Cl)0 n^ 1,6375
17
-P (SCH2-<^
1,6169
18
Il
C2H5-P(SCH2
Cl).
1,6249.
19
It
Cl-CH2-CH2-P (
1,6193
20
Cl-CE9-CH2-P (SCH2-^ ^-Cl )g n^ 1,6282
21
0 CH,.
Il ■'
J
CH - P
00984 171977
1,6099
20H061
Die Mittel, welche die Wirkstoffe der Formel I enthalten^können in der verschiedenartigsten Weise appliziert
werden z.B. in Form von wässrigen Sprays, Stäubepulvern usw.
Wässerige Sprays können beispielsweise auf Basis eines emulgierbaren Konzentrats oder eines benetzbaren Pulvers
erzeugt werden. Ein geeignetes emulgierbares Konzentrat kann beispielsweise aus ungefähr 25 Teilen einer Verbindung der
Formel (i) 40-50 Teilen Diacetonalkohol oder Isophoron, 20-30
Teilen eines aromatischen Petroleumproduktes, Xylol, Toluol oder eines anderen Gemisches solcher Lösungsmittel, und
2-10 Teilen eines oder mehrerer Emulgiermittel hergestellt werden. Es können auch geringe Mengen eines Mittels, das die
Ausbildung einer homogenen Lösung fördert wie Methanol-, Methoxymethanol oder Butoxymethanol verwendet werden.
Ein geeignetes Emulgiermittel kann z.B. aus 1-1,5 Teilen dodecylbenzolsulfosaurem Calcium oder Natrium, 2,5-·^
Teilen eines Oktyl- oder Nonyl-phenoxy-polyätoxyäthanols,
sowie ungefähr 0,5-1 Teil Methanol und 0-0,8 Teilen Xylol hergestellt werden. Die resultierende Mischung wird den
Lösungsmitteln und dem aktiven Körper der Formel I in dem oben angegebenen Mengenverhältnis zugesetzt. Es können aber
auch ein oder mehrere andere oberflächenaktive Mittel ver-
0098Λ1/1977
■20H061
wendet werden.
Je nach Wunsch und Zweck'mässigkeit kann igend
ein beliebiges solches MIttel verwendet werden, wie ein
anionisches oder kationisches oder ein nichtionisches, in
Lösungsmitteln lösliches Emulgiermittel. An Stelle des
oben erwähnten, von einem Alkylphenol und Aethylenoxyd abgeleiteten nichtionisohen Mittels können beispielsweise
Aethylenoxydkondensate von langkettigen Alkoholen, Carbonsäuren, Phenolen, oder Aminen verwendet werden. Verbindungen
dieser Arten sind im Handel erhältlich. Auch nichtionische Kondensate von Polyglyzerinen und einer
harzbildenden Säure wie Phthalsäure können bei der Herstellung von selbstemulgierenden Präparaten Verwendung
finden. Typische anionische Mittel sind solche auf Basis von Alkoholsulfonaten, -Sulfaten oder Sulfosuccinaten. In
Lösungsmitteln lösliche kationische oberflächenaktive Mittel sind z.B. Oleylbenzyldimethylammoniumchlorid, oder Dodecylbenzyltrimethylammoniumchlorid
oder -bromid. Daraus ist zu ersehen, dass der Charakter des Emulgiermittels'im
einzelnen ohne besondere Bedeutung ist, vorausgesetzt, dass es in der Lösung des Wirkstoffs in einem oder in
mehreren inerten organischen Lösungsmitteln löslich ist.
009841/1977
.ίο- 20U061
Ein benetzbares Pulver kann erhalten werden, wenn man einen Wirkstoff der Formel I" in einem flüchtigen Lösungsmittel
wie beispielsweise Aceton aufnimmt und mit einem feinzerteilten Peststoff wie Kaolin, Pyrophyllit, oder Diatomeenerde
unter Verdampfung des Lösungsmittels zusammenbringt. Das Pulver wird mit geringen Mengen eines oder mehrerer Netz-Dispergiermittel
erhitzt. Eine typische Zusammensetzung besteht z.B. aus 20 Teilen eines Wirkstoffes der Formel I
77^5 Teilen eines oder mehrerer feinzerteilter Feststoffe,
0,5 Teile Netzmittel, wie eines Oktylphenoxy-polyäthoxyäthanols und 2 Teile Natriumsalz der Methylen-bis-naphthalindisulfosäure.
Stäube mit einem Gehalt von 5-10 % des aktiven
Mittels können durch Verdünnung eines solchen benetzbaren Pulvers mit einem feinzerteilten festen Träger
hergestellt werden. Wenn gewünscht, kann das Netzmittel weggelassen werden. Auch das Dispergiermittel kann, wenn
gewünscht, weggelassen oder durch andere ersetzt werden.
Jedes der oben beschriebenen fungiziden Präparate enthält in der Regel einen Träger und in den meisten
Fällen ein oberflächenaktives Mittel.
Die erfindungsgemässen Mittel können für sich oder
in Mischungen mit anderen fungizid wirksamen Stoffen appliziert werden.
009841 / 1977
_ X1 . 20U061
Als solche seien beispielsweise genannt:
Anorg.Verbindungen ' : -
Elementarer Schwefel ' ·
Ammoniumpolysulfid Natriumpolysulfid
Bariümpolysulfid
CalGiumpolysulfid und Calciumthiosulfat (lime sulfur) Caiciumhypochlorit
Natriumtetraborat-dekahydrat (Borax) Zinkchlorid
Magnesiumborat ·
Nickelsulfat %
Kaliumchromat l .'■'-.-■
Bleiarsenat '
Cadmiumchlorid
Cadmiumcarbonat
009841 /1977
-12- 20U061
Ku ρ forverb i ndungen
Kupfer(I)oxyd (cuprous oxide)
Bordeaux-Brühe (Bordeaux mixture). Kupfer(II)sulfat-pentahydrat (copper sulfate) Basisches Kupfer(Il)chlorid (copper oxychloride) Kupfer(IT)phosphat
Bordeaux-Brühe (Bordeaux mixture). Kupfer(II)sulfat-pentahydrat (copper sulfate) Basisches Kupfer(Il)chlorid (copper oxychloride) Kupfer(IT)phosphat
Tribasisches. Kupfer(II)sulfat (tribasic copper sulfate)
Basisches Kupfer(II)carbonat (copper carbonate, basic)
Kupfer(II)-dihydrazin-sulfat
Kupferamminkomplexe
Kupferamminkomplexe
Kupfer(II)sulfat-Ammoniumcarbonat-Mischung
Kupfer(II)chlorid-basisches Kupfer(ll)sulfat-Mischung
Basisches Kupfer(II)carbonat-Zinksalz-Mischung Kupfer(II)-Zink-chromat-KompJex (copper zinc chromate)
Kupfer(IIJ-Zink-dadmium-calcium-chromat-Komplex
Kupfer(ll)Salz der Oelsäure (copperoleate) Kupfer(II)salze von Fettsäuren
Kupfer(Il)salz der Ifaphthensäure (copper naphthenate)
Kupfer(II)salz des δ-FIydroxychinolins (oxine-copper)
Kupfer(II)salz des l,2-Naphthochinonoxims-(2)
Kupfer(II)salz des 5-Phenylsalicylafcs
00 9841/1977
20U061
Zinn- und Quecksilberverbindungen Bis-(tri-n-butylzinn)oxyd ■
Triphenylzinnhydroxyd (fentin hydroxide)
Triphenylzinnacetat (fentin acetate)
3is~(tributylzinn)succinat
Quecksilber(I)Chlorid (Kalomel) · ·
Quecksilber(II)chlorid (mercuric chloride)
Quecksilber(Il)oxyd Quecksilber-Zink-chromat-Komplex
Quecksilber(II)lactat ,
■Aethylquecksilbcrchlorid (ethylmercuri chloride)
2-Kydroxyäthylquecksilberacetat
Äethylcuecksilberisothiocyanat ^-Aethoxypropylquecksilberbromid
Chlormethoxypropylquecksilberacetat ■ Methoxyäthylquecksilberchlorid
2-f'*ethoxyäthylquecksilbersilikat
3is-(rr.ethylquecksilber)sülfat '
Bis-imethylquecksilberjammoniumacetat
Aethylquecksilberacetat · S-Methoxyäthylquecksilberacetat
Aethylquecksllberphosphat Isopropylmethylquecksilberacetajb
Kethylquecksilbercyanid
Methyiquecksilberbeniioafc
K-Cyano-N1 (rnethylquecksllber)g;uanidin
MethylcuockiJÜborpcntacblorphenolat;
00 9841/1977
20H061
Aebhylquecksilber-2,3-dIhydroxypropylmerkaptid
Kethylquecksilber-8-hydroxychinolat (Ortho LM) ·
N-(f'ethylquecksilber)-l ,2I-, 5*6,7,7-hexachlorobicyclo
[2 hept-5-en~2,3-dicarboximid
[2.2.l| hept-5-en-2,3-dicarboximid Natriumsalz des Aethylquecksilberthiosalicylats
N-(Aethylquecksilber)-p-toluolsulfonsäureanilid
Phenylquecksilveracetat (PAM) Phenylquecksilberpropionat
Phenylquecksilbertriäthanolammoniumlactat (PAS) "
Phenylquecksilberharnsboff (phenylmercuri urea) N-(Phenylquecksilber)-l,4,5..6,7,7-hexachlorobicyclo *
(2.2.1] hept-5-en-2,3-dicarboximid Phenylquecksilberdimethyldithiocarbamat
Phenylquecksilberformamid
Phenylquecksilberchlorid
Phenylquecksilberacetat
Phenylquecksilberbenzoat
Phenylquecksilberborat
Phenylquecksilberchlorid
Phenylquecksilberacetat
Phenylquecksilberbenzoat
Phenylquecksilberborat
Phenylquecksilberhydroxyd
Phenylquecksilberjodid
Basisches Phenylquecksilbernitrat Phenylquecksilbermonoäthanolamlnlactat
Phenylquecksilborsalicylat
Hydroxyquecksilberchlorphenol
009841/1977
2OU 061
Hydroxyquecksilbertrichlorphenol .
Hydroxyquecksilbernitrophenol : N-Phenylquecksllberäthylendiamin " '
Hydroxyquecksilbernitrophenol : N-Phenylquecksllberäthylendiamin " '
Phenylquecksirpermonoäthanolammoniumacetat
Pyridylquecksilberacetat .
Diphenylquecksilber-S-hydroxychinolab. ' Quecksilber(II)^-Komplex mit organischen Phosphaten
Diphenylquecksilber-S-hydroxychinolab. ' Quecksilber(II)^-Komplex mit organischen Phosphaten
Mischung von Methylquecksilber-2,3-ciihydroxypropylnierkaptid
und Methylquecksilberacetat
Mischung von Aethylquecksilber-^,3-dihydroxypropylmerkaptid
und Aefhylquecksilberacetat .
Mischung von Kydroxyquecksilberchlorphenol und Hydroxyquecksiroernitrophenol
·
Quecksilber-Cadmium-organischer Komplex
V/eitere org. Metallverbindungen
Cadmiurnsuccinafc
Cadinia-n-di-n-propyl-xanthogenafc
Cadmiuin-S-hydroxychinolat
Phenylaminocadmiumacetat .
Phenylaminocadmiumdilactat
Methylarsinsulfid
Zinkoktat
Zinkoleat
Cadmiuin-S-hydroxychinolat
Phenylaminocadmiumacetat .
Phenylaminocadmiumdilactat
Methylarsinsulfid
Zinkoktat
Zinkoleat
009841/1977
.. 20H061
Einfache org. Verbindungen (Aliphaten)
Formalin
Paraformaldehyd Acrolein
Methylbromid ·'
Methylisothiocyanat Tetrajodäthylen 1,3-Dichlorpropenund verwandte chlorierte (^-.-Kohlenwasserstoffe 1-Chlor-^-brompropen(1) trans-l> ii-Dibronibuten(2) l^-DichlorpropenCl) l-Chlor-2-nitro-propan 2-Chlor-l-nitropropan Trichlornitromethan Dichlortetrafluoraceton Natriumsalz der Propionsäure Calciumsalz der Propionsäure
Paraformaldehyd Acrolein
Methylbromid ·'
Methylisothiocyanat Tetrajodäthylen 1,3-Dichlorpropenund verwandte chlorierte (^-.-Kohlenwasserstoffe 1-Chlor-^-brompropen(1) trans-l> ii-Dibronibuten(2) l^-DichlorpropenCl) l-Chlor-2-nitro-propan 2-Chlor-l-nitropropan Trichlornitromethan Dichlortetrafluoraceton Natriumsalz der Propionsäure Calciumsalz der Propionsäure
Chlorfumarsäure-bis-ß-chloräthylester
Sorbinsäure und deren Kaliumsalz 2-Propen-l,l-diolacetat 2-Aminobutan
Dodecylguanidinacetat (dodine)
Dodecylguanidinphthalafc
a-Bromacetylvalinarnid
0098A1/197
r,2-Dichlor-l-(me-thylsulfonyl )-äthylen
l,2-Dichlor-l-(butylsulfonyl>äthylen
trans~l,2-Bis--(n-propylsulfor.yl)-athylen
20U061
p-bichlorbenzol (paradichlorbenzene)
' Hexachlorbenzol (HCB) 1,2,4,5-Tetrachlor-^-nitrobenzol(tecnazene)
Pentachlornitrobenzol (quintozene)
Isomerengemisch von !,^j^-Trichlor-Sjö-dinitrobenzol und
l,2,^-Trichlor-4,6~dinitrobenzol
2,4,5^6-Tetrachlorisophthalsäurenitril
2,4-Dinitrophenyl-thio.cyanat .
Diphenyl (biphenyl) . ·
o-Mitrodiphenyl
l-Chlor-2,4-dinitronaphthalln
Äcenaphthen" · a l
009841/1977
-18" 20U061
Phenole
• 2,4,6-Trichlorphenol ·
2,h,5-Trichlorphenol
2 s h,5-Trichlorphenylacetat
2,^,5-Triehlorphenyl-chloracefcab
Trichlorphenole Zinksalz m-Xresylacetat
2,3^6-Tetrachlorphenol
2,3^6-Tetrachlorphenol
Pentachlorphenol (PCP) . »
o-Dihydroxybenzol 2,4-Dioxy-n-hexylbenzol
2-Phenylphenol (orthophenylphenol) 3,5-Di"°rcrnsalicylaldehyd · -
2-Benzyl-4-chlorphenol .
2,2' -Dihydroxy-'5,5 '-dichlor-diphenylmethan (dichlorophen)
2,2'-Dihydroxy-3i 3'>5,5'* 6,6'-hexachlor-diphenylmethan
2,2'-Dihydroxy-5,5'-dichlor-diphenylsulfid
2,2'-Dihydroxy-3,31 ,5,5'-tetrachlor-diphenylsulfId
2,2'-Dihydroxy-3,y ,5.5'-tetrachlor-diphenylsulfid-di-Natriumsair
4-Chlor-o-phenylphenol 1,^-Dichlor-2,5-dimcthoxybenzol (chloroneb)
Sallcylanilid
V.'israutsalicylafc Mit Chlor oder Brom halogeniertes Trifluormethylsalicylanilid Dromiertes Salicylanilid (j5i5-Dimethyl-'l--chlorphenoxy)-lithanol
V.'israutsalicylafc Mit Chlor oder Brom halogeniertes Trifluormethylsalicylanilid Dromiertes Salicylanilid (j5i5-Dimethyl-'l--chlorphenoxy)-lithanol
0098A1/1977
; j - 19- 2QH061
Dinitrdphenclrierlvate ·
2-(l--Methyl-r.-propyl5-4,6-dinltrophenyl-2-methylGrotonat (binapacryl)
2-(l-H?thyl-n-prop,yr.)-4J6-dinitrophenylisopropylcarbonat (dinobuton)
2-(l-r<iethyl-n-heptyl)-4,6-dinitrophenylcrotonat (dinocap)
:':ethyl-2>6-dinitro-4-(l-äthvl-hexyl)oheny,lcarbonat +
Methyl-2,o-dinitro-4-(l^propyl-pentyl)phenylcarbOnat
4-Konyl-2,6-dinitro-phenylbutyrat · '
S-Kethyl-2"-(l-raethyl-n-heptyl}-irJ6'-dinitrophenyitMocarbohafc -
Aril i rider Jy ate ·
2,o-Dichlor-^-nitroanilin (dichloran) ' 2«Cyanoäthyl-Mrphonylcarbamat
■ Fropynyl-U-phenylcarbamat
a-(2-3romaGetoxy}-acetanilid
a-(2-3romaGetoxy}-acetanilid
benzochinonCl·,^) (chloranil)
2i3-Dichlor-naphthochinon(rJ,4) (dichlone)
2-Amino-3-chlor-naphthochinon(l,4) ·
2-Chlor-j5-acetamino-naphthochinon(l1>4)
4-Mefnyl-2#3,5,10-tetrahydro-3,5,10-trioxo-2Hl4-H-naphtho
(2b)4Wi
2/3,6, T-Tetrachloro-'la, Sa-epoxy-l, Z, 3,4,4a, Ba-hcxahydro-l, U-rr.etnanoriaphthalin-5,8-dion
Chinonoximbenzoylhydrazon (benquinox) ' ■_ .
BAD ORIGINAL
00 9841/197 7 ~
?richlormethvlthiο-derivate
20H061
ff-(Tri chlorine thylthio)phthalimid (folpe't)
N-(Trichlorrnethylthio)cyclohex-4-en-l,2-dicarboximid (captan)
N-il^l^^-tetrachloräthylthioJcyclohex-^-en-l^-dicarboximid
(captafoi)
•K-Methansulfonyl-N-trichlormethylthio-p-chloranilin
K'-Dichlorfluormethylthiο-NN-dimethyl-N'-phenylsulfamid
(dichlofluanid)
S-(2-Pyridyl-l-oxyd)-S'-trichlorrnethyl-disulfid; Hydrochlorid
Org. Phosphate
0,0,O-Triraethylthiophosphat
0} O-Diathyl-phthalimidophosphonothioat 5-Amino-bis-(dimethylamido)phosphinyl-2-phenyl-l,2,4-triazol (triamiphos) ;
0,0,O-Triraethylthiophosphat
0} O-Diathyl-phthalimidophosphonothioat 5-Amino-bis-(dimethylamido)phosphinyl-2-phenyl-l,2,4-triazol (triamiphos) ;
S-Methylamino-bis-CdimethylamidoJphosphinyl-^-phenyl-l^^f-triazol
0,O-Diäthyl-0-2-pyrazinyl-phosphorthioat
O-Aethyl-SjS-diphenyl-dithiolphosphafc
0-Aethyl-S-benzy.l-phenyldithiophosphonafc 0,O-Diäthyl-S-benzyl-thiolphosphat
0-Aethyl-S-benzy.l-phenyldithiophosphonafc 0,O-Diäthyl-S-benzyl-thiolphosphat
BAD ORDINAL
009841/1977
- 21- 2QUQ61
Dithiocarbamate ·
Zinksalz der Dithiocarbaminsäure iiatrium-K-methyl-dithiocarbamat (metham)
Natriurn-K-methoxyäthyl-dithiocarbamat
i.'atriurn-N^ii-dimethyl-dithiocarbarnat (DDC)
Amrnonium-N^N-diniethyl-dithiocarbamat " . '
Zink-KjN-dimethyl-dithiocarbamat (ziram) . ·
Eisen-MjN-dimethyl-dithiocarbamat (ferbam)
Kupfer-ii/N-dimethyl-dithiocarbamat. . . ,*
Dinatriura-äthyleri-ljS-bis-dithiocarbamat (nabam)
Zink-äthylen-l^-bis-difchiocarbamat (zineb)
Eisen-äthylen-l^-bds-dlthiocarbamat
Mangan(II)-äthylen-l,2-bis--dithiocarbamat' (maneb)
Calciumräthylen-l^-bis-dithiocarbamafc ·
Aramoniurn-ä.thylen-l^S-bis-dithiocarbamat -
Zink-pr.opylen-l,2-biΓ,-dithiocarbamat (mezineb) (propineb)
BisCdiriiethylthiocarcanylJ-äthylen-l^-bis-dithiocarbamat
Komplex bestehend aus (rnaneb) und Zinksalz (rnancozeb)
Tetraäthylthiuram monosulfid
Bis-(M,N-dirriethyldithiocarbamylmerkapto)-niethylarsin
Tetrarnethylthiuramdisulfid (thiram) Dipyrrolidylthi.uramdisulfid ·
Ii,N'-3is-(dimethylamino)thiuramdisulfid
Polyäthylenthi:Ui.rariisulf.ld
Komplex bestehend aus (zineb) und polyäthylenthiurarndisulfid
(metiram)
009841/1977 «D-ORiaWA
20H0.61
Bis-(3,4-dichlor-2(5)-furanoyl)äther (mucochloric anhydride)
2-Methoxyniethyl-5-nitrofuran 5-Nitro-furfuraldoxim-(2)
5-Nitro-furfuryl-amidoxim-(2) l-0xy-5-acetyl-6-methyl-cyclohexen-(5)dion-(2,4) (dehydroacetic
acid) .
1-N-Heterocyclen
3- [2-(5,5-Dimethyl-2-oxycyclohexyl)-2-hydroxyäthyi] -glutarimid
(cycloheximide)
Phthalimid '
Pyridin-2-thiol-l-oxyd bzw. l-Hydroxypyridin-2-thion
Zinksalz des Pyridin-2-thiol-l-oxyds Mansan(II)salz des Pyridin-2-thiol-l-oxyds
S-I(l-oxido-2-pyridyl)isothiuroniumchlorid
a,a-bis(4-chlorphenyl)-j5-pyridinmethanol (parinol)
8-Hydroxychinolin (8-quinolinol)
»
8-Hydroxychinolin-sulfat (chinosol) Benzoyl-8-hydroxychinolin-salicylat 3-(2-Methylpiperidino)propyl-5,4-dichlorbenzoat 6-Aethoxy-l,2-dihydro-2i2,jf-trimethylchinolin (ethoxyquin) N-Lauryl-isochinoliniutnbromid ■ 9-(p-n-HexyloxyphenylJ-lO-methyl-acridiniumchlorid 9-(p-n-Hexyloxyphenyl)-10-methyl-acridinium-p-toluolsulfonat
8-Hydroxychinolin-sulfat (chinosol) Benzoyl-8-hydroxychinolin-salicylat 3-(2-Methylpiperidino)propyl-5,4-dichlorbenzoat 6-Aethoxy-l,2-dihydro-2i2,jf-trimethylchinolin (ethoxyquin) N-Lauryl-isochinoliniutnbromid ■ 9-(p-n-HexyloxyphenylJ-lO-methyl-acridiniumchlorid 9-(p-n-Hexyloxyphenyl)-10-methyl-acridinium-p-toluolsulfonat
0098A1/1977
■ °" ■ 20U061
2- und ^-^-Heterocyclen
2-n-Hepta.decylimidazolidinacetat (glyodine)
l-Hydroxyäthyl-2-heptadeeyiimidazolidin
l-Phenyl-3,5-dimethyl-^-nltrosopyrazol
l-p-ChlorphenylO^-dirnethyl-'J-nitrosopyrazol
l-p-Sulfamylphenyi-5,5-dimethyl-4-nitrosopyrazol
N-(l-Phenyl-2-nitropropyl)piperazin " ·
2-Diraethylamino-6-rnethyl-5-n-butyl-^-hydroxy-pyrimIdin '.
K-Dodeyl-l,4,5,6~tetrahydropyrimidin . * *
N-Dodecyl-2-methyl-l,4,5,6-tetrahydropyrimidin
2-n-Heptadecyltetrahydropyrimidin . "
l-(4-Amino-^-propyl-5-pyrimidyl-methyl)-2-methylpyridiniumchloridhydrochlorid
· ν
2-(2'-Furyl)-benzimidazol (furidazol) 3-Dodecyl-l-πlethyl-2-phenylbenzimidazoliura-ferrIcyanid
Methyl-N-benzimidazol-2-yl-N-(butylcarbamoyl)carbama't (benomyl)
2-(o-Chloranilino)-4,6-dichlor-sym.-trlazin · ·
2-Aethylamino-6-methyl-5-n-butyl-2J-hydroxypyrimidIn
S-Chlor-^-phenyl-l^-dithiol-J-on
2,3-Dicyano-l,4-dithia-anthrachinon (dithianon)
2-(4-Thiazolyl)-benzimidazol
00-9 841/1977
" 24 " 20H0.61
4-(2-Chlorphenylhydrazono)-3-niethyl-5-isoxa5iolon (drazoxolon)
Thiazolidinon-4-thion-(2) (Rhodanin) . 3-(p-Chlorphenyl)-5-methylrhodanin
^J5-Dimethyltetrahydro-l,5,5-thiadiazin-2-thion (dazomet)
^J5-Dimethyltetrahydro-l,5,5-thiadiazin-2-thion (dazomet)
■3,5t-Aethylen-bis-(tetrahydro-4,6-dimethyl)-2H-l,3,5-thiadazin-2-thion)
(milneb)
3-3enzylidenamino-4-phenylthiazolin-2-thion
6~Chiorbenzthiazoi~2-thiol, Zinksalz '
6-ß-Diäthylaraino-äthoxy-2-dimethylamino-benzthiazoX^1ihydrochlorid
MonoäthanolammoniujTi-benzthiazol-2-thiol "
Laurylpyridinium-5-chlor-2-merkaptobenzthiazol
Zink- und Natriumsalze des 2-Merkaptobenzthiazols und Dimethyldithiocarbamate
6-(ß-Diäthylarninoäthoxy)-2-dimethylaminobenzthiazol-dihydrochlorid
^-TrichlormethyltHiobenzothiazolon
3-Trichlormethylthiobenzoxazolon
3-(Trichlormethyl)-5-äthoxy-l,2,4-thiadiazol
6-Methyl-2-oxo-l,j5-dithiolo [^^5-3 -ohinoxalin (quinomethionate)
2-Thio-l,5-dithiolo j5,5-bj -chinoxalin (thioquinox)
2J3-Dihydro-5-carboxanilido-6-methyl-l,i+-oxathin
^O^j^-Tetrachlortetrahydrothiophen-ljl-dioxyd
2J3-Dihydro-5-carboxanilido-6-methyl-lJ4-oxathin-4,4-dioxyd
0098A 1/1977
• ·
■ «
Cetyl-trimethylammoniumbromid ·
n-Alkyl(C12,C1^,G1g)dirnethylbenzylammoniurnchlorid
Alkenyl-dimethyläthylammoniumbromid " ■-
Dialkyldimethylarnmoniumbroniid
Alkyldimcthylbenzylammoniumchlorid
Alkyl CQ-C.j-tolylmethyltrimethylammoniumchlorid ,
Di-isobutylkresoxyathoxyathyldiraethylbenzylammoniumchlorid
p-Di-isobutylphenoxyäthoxyäthyldirnethylbenzylammoniunichlorid
Benzoyltrimethylarr.moniumbromid .
Fungizide Antibiotika Gliotoxin
2,JUDiguanidino-^/^,ö-trihydroxycyclchexyl 5-deoxy-2-0-(2-deoxy-2-rnethylamino-a-L-slucopyranosylJ^-C-rormyl-ß-L-lyxopentanofuranosid
(streptomycin) .
7-ChIOr-H,6-dimethoxycumaran-3-on-2-spiro-l'-(2'-methoxy-61-methylcyclohex-21-en-4'on)
(griseofulvin)
hexahydroxy-6-methyl-l,ll-dioxo-a-naphthacencarboximid
(Oxytetracyclin) '
7;
pentahyclroxy-e-incthyl-l, ll-dioxo-2-naphtha csncarboximid
(Ghlortetracyclin) ".·· ;.
(Pimaricin) ·
(Lancomycin) *
(Phleomycin) · · '
(Kasugamycin)
(Phytoactin) o09841 Z1977
20U061
D(-)-threo-2.,2-dichlor-N- (S-hydroxy-cc-ChydroxymethylO-pnitrcphen-äthyl]
aretamid(Chloramphenicol)
Blasticidin-S-benzylamino-benzolsulfonat
Varia
N-(j5-nitrophenyl)itaconimid
Phenoxyessigsäure
Natrium-p-dimethylamino-benzoldiazosulfonafc
Acrolein-phenylhydrazon **
2-Chloracetaldehyd(2,4-dinitrophenyl)-hydrazon
2-Chlor-^-(tolylsulfonyl)-propionitril
l-Chlor-2-phenyl-pentan-diol(4,5)-thion())
p-Nonylphenoxypolyäthylenoxyäthanol-Jod-Xomplex
(a-Mitromethyl)-o-chlorbenzylthioäthylamin-hydrochlorid
3-(p.- t,-butyl-phenylsulfonyl )acrylonitril
Oktachlorcyclohexenon
Pentachlorbenzylalkohoi
Pentachlorbenzylacetat
Pentachlorbenzaldehyd-cyanhydrin
2-Norcamphanrnethanol
2 j6-Bis-(dimethylaminoniethyl)-cyclohexanon
Decachloroctahydro-l,3,i}-wetheno-2H-cyclobutaIcd3-pentalen-2-on
1 - (^-Chlorallyl)-3,5,'7-fcria2a-l-azoniaadafriantanchlorid
Kohlenteer und Hochofenteer
9 8 4 1/19
Mischung Nickelsulfat-Maneb - '
Mischung Kaneb-Kerkaptobenzthiazol Mischung
Zineb-Merkaptobenzthiazol Mischung Zineb-NickelCllJ-chlorld
Mischung Zineb-Niekel(Il)-sulfat
Mischung Ziram-basisches' Kupfersulfat Mischung Ziram-Zink-merkaptobenzthiazol
Mischung Thiram-Cadmiumchloridhydrat Mischung Thiram-Hydroxyquecksilberchlorphenol
Mi s chung Thiram-PhenylquecksiIberacetat
Mischung Polyäthylen-bis-thiuramsulf id-KupferoxyChlorid
Mischung Methylarsin-bis-(dimethyldithiocarbamat)-ziram-fchiram
Mischung Folpet-Phenylquecksilberacefcat Mischung Dodine-Ferbam-Sehwefel ■
Mischung Dithianon-Kupferoxychlorid
Mischung Dichlone-Ferbam-Schwefel · Mischung Dinocap-Üinitrooctylphenol
Mischung Gaptan-quintozene-tribasischem Kupfersulfafc
Mischung Cadmiumpropionafc-Phenylquecksilberpropionafc
Formaldehyd -Harnstoff-P4ischung ·
Mischung Phenylammoniumcadniiumdilactat-Phenylquecksilberforraainid
Mischung basisches Kupfersulfat-Zinksalze
009841/Ί977
Die Verbindungen der Formel I sind bisher nicht in der Literatur beschrieben worden. Die Erfindung bezieht
sich auch auf diese neuen Verbindungen.
KO Ge.wichtsteile einer aktiven Verbindung werden
in einer 25 ^igen Xylollösung einer Mischung, die aus
gleichen Gewichtsteilen eines Kondensationsproduktes von etwa 1 Mol p-tert. Oktylphenol mit etwa 10 Molen Aethylenoxyd
und p-dodecyl-benzolsulfosaurem Calcium besteht, aufgenommen
un'd das Ganze mit Xylol auf 100 Volumteile aufgefüllt. Beim Verdünnen mit Wasser auf die gewünschte Konzentration
entsteht eine stabile, sehr gut spritzfähige Emulsion.
Die Verbindungen Nr. 1 und Nr. 7 zeichnen sich durch ihre Wirkung gegen Piricularia oryzae Bri. et Cav.,
den Erreger der Rice blast disease, aus. Reispflanzen wurden im Gewächshaus angezogen und mit einer wässrigen
Konidiensuspension des Testpilzes infiziert. Die Pflanzen
00984 1 / 1S77
wurden in einer Feuchtkammer inkubiert und am Tage nach der Infektion mit einer wässrigen Brühe, enthaltend 0.1$
Wirkstoff der Untersuchungspräparate, gespritzt.
Nach einer Woche zeigten die behandelten Pflanzen einen Befall von 5 %» gegenüber einem 100 folgen Befall
der Kontr.ollpflanzen·..
Die Verbindung Nr4 7 erzielte dieses Ergebnis
noch in einer Verdünnung von 0,03 % Wirkstoff.
Q09841/1977
Claims (9)
- -jo- 20U061PatentansprücheVerfahren zur Herstellung von Phosphonsäureestern der allgemeinen Formelworin X ein. Sauerstoff- oder Schwefelatom, R, einen gegebenenfalls substituierten niederen Alkyl- oder Aralkylrest, R2 und R, Wasserstoff oder einen der folgenden Substituenten bedeuten: einen niederen Alkylrest, eine Nitrogruppe oder eine TrIfluormethy1gruppe, eine Cyanogruppe, ein Halogenatom, und η und m die Zahlen 1 oder 2 bedeuten, durch Reaktion eines Mols eines Alkan-(thio)-phosphonsäuredihalogenids χR1 - P(HaI)2worin Hai Chlor oder Brom bedeutet, mit zwei Molen eines entsprechend substituierten Benzylmercaptans oder in zwei Reaktionsstufen mit einem Mol des ersten substituierten und danach mit einem Mol des zweiten substituierten Benzyl-0 9 8,1/1977. ■ -31- . 20Η06Ϊmercaptans, Jeweils in Gegenwart eines säurebindenden Mittels. . ,. '
- 2. Fungizide Mittel, welche als aktive Komponente mindestens einen Ptiosphonsaureester der allgemeinen Formelenthalten, worin X ein Sauerstoff- oder Schwefelatom, R einen unsubstituierten oder mit Halogen substituierten niederen Alkyl- bzw.. Aralkylrest, Rg . Uaol H, Wasserstoff, einen niederen Alkylrest, eine Nitrogruppe, eine Trifluormethy1gruppe, eine Cyanogruppe, ein Halogenatom und η und m die Zahlen 1 oder 2 bedeuten, zusammen mit einem oder mehreren Zusätzen,
- 3. Fungizide Mittel gemäss Patentanspruch 2, dadurch ' gekennzeichnet, dass in dem als aktive Komponente verwendeten Phosphonsäureester X ein Sauerstoffatom und R. eine niedere Alkylgruppe bedeuten.009841 /197720U061
- 4. Fungizide Mittel gemäss Patentanspruch 1, dadurch gekennzeichnet, dass sie als aktive Komponente den Dithiolphosphonsäureester der Formel0 Il CH3 - P (S - CH- C6H )enthalten.
- 5. Fungizides Mittel gemäss Patentanspruch 2, dadurch gekennzeichnet, dass sie als aktive Komponente den Dithiolphoßphonsäureester der FormelISoC5H7 - P (S - CH2 - C6H5)enthalten.
- 6. Die im Patentanspruch 2 genannten Phosphonsäureester.
- 7. Die im Pateritanspruch 3 genannten Phosphonsäureeeter.
- 8. Der im Patentanspruch 4 genannte Phosphonsäureeeter.
- 9. Der im Patentanspruch 5 genannte Phosphonsäure-•eter.009841/1977
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH510769A CH506948A (de) | 1969-04-02 | 1969-04-02 | Fungizides Mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2014061A1 true DE2014061A1 (de) | 1970-10-08 |
Family
ID=4288032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702014061 Pending DE2014061A1 (de) | 1969-04-02 | 1970-03-24 | Fungizide Mittel |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3867484A (de) |
| CH (1) | CH506948A (de) |
| DE (1) | DE2014061A1 (de) |
| FR (1) | FR2044711A1 (de) |
| GB (1) | GB1289085A (de) |
| IL (1) | IL34194A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0230481A1 (de) * | 1985-10-08 | 1987-08-05 | Stauffer Chemical Company | S-Aralkyltrithiophosphonat-Insektizide |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4559175A (en) * | 1984-04-19 | 1985-12-17 | The United States Of America As Represented By The Secretary Of The Air Force | Halo-substituted diphospha-s-triazines and their derivatives |
| DE4003054A1 (de) * | 1990-02-02 | 1991-08-08 | Hoechst Ag | Verwendung von benzylphosphonsaeurederivaten zur behandlung von durch viren verursachte krankheiten |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3185721A (en) * | 1960-03-05 | 1965-05-25 | Bayer Ag | Thiophosphonic acid esters or ester amides and processes for the production thereof |
| US3094405A (en) * | 1961-02-08 | 1963-06-18 | Stauffer Chemical Co | Defoliant methods using thio esters of chloromethyl phosphonous and chloromethyl phosphonic acids |
-
1969
- 1969-04-02 CH CH510769A patent/CH506948A/de not_active IP Right Cessation
-
1970
- 1970-03-24 DE DE19702014061 patent/DE2014061A1/de active Pending
- 1970-03-30 IL IL34194A patent/IL34194A/en unknown
- 1970-03-31 FR FR7011482A patent/FR2044711A1/fr not_active Withdrawn
- 1970-04-01 US US024855A patent/US3867484A/en not_active Expired - Lifetime
- 1970-04-02 GB GB1289085D patent/GB1289085A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0230481A1 (de) * | 1985-10-08 | 1987-08-05 | Stauffer Chemical Company | S-Aralkyltrithiophosphonat-Insektizide |
Also Published As
| Publication number | Publication date |
|---|---|
| IL34194A0 (en) | 1970-05-21 |
| CH506948A (de) | 1971-05-15 |
| IL34194A (en) | 1973-04-30 |
| FR2044711A1 (de) | 1971-02-26 |
| GB1289085A (de) | 1972-09-13 |
| US3867484A (en) | 1975-02-18 |
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