CS219905B2 - Fungicide means and method of making the active agents - Google Patents
Fungicide means and method of making the active agents Download PDFInfo
- Publication number
- CS219905B2 CS219905B2 CS795676A CS567679A CS219905B2 CS 219905 B2 CS219905 B2 CS 219905B2 CS 795676 A CS795676 A CS 795676A CS 567679 A CS567679 A CS 567679A CS 219905 B2 CS219905 B2 CS 219905B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- anilide
- furyl
- acid
- oxoperhydro
- methyl
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 11
- 239000013543 active substance Substances 0.000 title description 15
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000000417 fungicide Substances 0.000 title 1
- -1 C3-C6-alkynyl Chemical group 0.000 claims abstract description 59
- 239000002253 acid Substances 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical class CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 21
- 241000233866 Fungi Species 0.000 abstract description 8
- 239000000969 carrier Substances 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 3
- 230000003032 phytopathogenic effect Effects 0.000 abstract description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 150000003931 anilides Chemical class 0.000 description 56
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- 241000196324 Embryophyta Species 0.000 description 17
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 239000002689 soil Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 101100126625 Caenorhabditis elegans itr-1 gene Proteins 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- MLXDUYUQINCFFV-UHFFFAOYSA-N 2-acetyloxyacetic acid Chemical compound CC(=O)OCC(O)=O MLXDUYUQINCFFV-UHFFFAOYSA-N 0.000 description 5
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000003415 peat Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 240000004713 Pisum sativum Species 0.000 description 3
- 235000010582 Pisum sativum Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 3
- 230000017074 necrotic cell death Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- VJIKFWJCVWFZIN-UHFFFAOYSA-N 2-ethylsulfanylacetic acid Chemical compound CCSCC(O)=O VJIKFWJCVWFZIN-UHFFFAOYSA-N 0.000 description 2
- CSGYOTJDPQKSIC-UHFFFAOYSA-N 2-propan-2-ylsulfonylacetic acid Chemical compound CC(C)S(=O)(=O)CC(O)=O CSGYOTJDPQKSIC-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000004160 Capsicum annuum Species 0.000 description 2
- 244000299452 Gouania lupuloides Species 0.000 description 2
- 235000000292 Gouania lupuloides Nutrition 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000918584 Pythium ultimum Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001511 capsicum annuum Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 238000005554 pickling Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- HIAGSPVAYSSKHL-UHFFFAOYSA-N 1-methyl-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C(C)=CC=C2 HIAGSPVAYSSKHL-UHFFFAOYSA-N 0.000 description 1
- GSFSVEDCYBDIGW-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-6-chlorophenol Chemical compound OC1=C(Cl)C=CC=C1C1=NC2=CC=CC=C2S1 GSFSVEDCYBDIGW-UHFFFAOYSA-N 0.000 description 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
- OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 description 1
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
- IXOFPUCWZCAFJX-UHFFFAOYSA-N 2-phenylethanethioic s-acid Chemical compound SC(=O)CC1=CC=CC=C1 IXOFPUCWZCAFJX-UHFFFAOYSA-N 0.000 description 1
- FTHCMTYOZSIHJL-UHFFFAOYSA-N 2-propan-2-ylsulfanylacetic acid Chemical compound CC(C)SCC(O)=O FTHCMTYOZSIHJL-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- JZLMLFCJWFMZMC-UHFFFAOYSA-N 3-phenylpropanethioic s-acid Chemical compound SC(=O)CCC1=CC=CC=C1 JZLMLFCJWFMZMC-UHFFFAOYSA-N 0.000 description 1
- ZZZHTQYZSFCJKM-UHFFFAOYSA-N 3-sulfanylidenebutanethioic s-acid Chemical compound CC(=S)CC(O)=S ZZZHTQYZSFCJKM-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- FXSAOVOBZBHELX-UHFFFAOYSA-N CC1=C(N(C(COC)=O)C2C(OCC2)=O)C=CC=C1C Chemical compound CC1=C(N(C(COC)=O)C2C(OCC2)=O)C=CC=C1C FXSAOVOBZBHELX-UHFFFAOYSA-N 0.000 description 1
- YALDBMRHFGSWGQ-UHFFFAOYSA-N CCC(=S)N(C1CCOC1=O)C2=C(C=CC=C2C)C Chemical compound CCC(=S)N(C1CCOC1=O)C2=C(C=CC=C2C)C YALDBMRHFGSWGQ-UHFFFAOYSA-N 0.000 description 1
- JLIIYNMYYZUIFJ-UHFFFAOYSA-N CCOCC(=O)N(C1CCOC1=O)C2=C(C=CC(=C2)Cl)C Chemical compound CCOCC(=O)N(C1CCOC1=O)C2=C(C=CC(=C2)Cl)C JLIIYNMYYZUIFJ-UHFFFAOYSA-N 0.000 description 1
- FYTLYPLMLQOAOF-UHFFFAOYSA-N COCC(=O)N(C1CCOC1=O)C2=CC=CC(=C2)C#N Chemical compound COCC(=O)N(C1CCOC1=O)C2=CC=CC(=C2)C#N FYTLYPLMLQOAOF-UHFFFAOYSA-N 0.000 description 1
- 235000002567 Capsicum annuum Nutrition 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- 241001633993 Cineraria Species 0.000 description 1
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000755093 Gaidropsarus vulgaris Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 241000410021 Pericallis cruenta Species 0.000 description 1
- 235000008376 Phaseolus vulgaris var nanus Nutrition 0.000 description 1
- 240000005315 Phaseolus vulgaris var. nanus Species 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 241000233626 Plasmopara Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 101150103877 Selenom gene Proteins 0.000 description 1
- 241000232168 Sinningia Species 0.000 description 1
- 244000093304 Sinningia speciosa Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- ITRPUMGWMLDMKO-UHFFFAOYSA-N [2-(2,6-dimethyl-N-(2-oxooxolan-3-yl)anilino)-2-oxoethyl] N,N-dimethylcarbamodithioate Chemical compound CC1=C(N(C(=O)CSC(N(C)C)=S)C2C(OCC2)=O)C(=CC=C1)C ITRPUMGWMLDMKO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 210000000436 anus Anatomy 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 229960003887 dichlorophen Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- MZGNSEAPZQGJRB-UHFFFAOYSA-N dimethyldithiocarbamic acid Chemical compound CN(C)C(S)=S MZGNSEAPZQGJRB-UHFFFAOYSA-N 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000006028 limestone Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- IPQNZYVMLHLAOK-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-methoxy-n-(2-oxooxolan-3-yl)acetamide Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)C1CCOC1=O IPQNZYVMLHLAOK-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 210000003371 toe Anatomy 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A01N47/14—Di-thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782841824 DE2841824A1 (de) | 1978-09-22 | 1978-09-22 | Essigsaeureanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes fungizides mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS219905B2 true CS219905B2 (en) | 1983-03-25 |
Family
ID=6050476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS795676A CS219905B2 (en) | 1978-09-22 | 1979-08-20 | Fungicide means and method of making the active agents |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5545682A (de) |
| AT (1) | AT365890B (de) |
| AU (1) | AU5107679A (de) |
| BE (1) | BE878924A (de) |
| BG (1) | BG30624A3 (de) |
| BR (1) | BR7905455A (de) |
| CS (1) | CS219905B2 (de) |
| DD (1) | DD145989A5 (de) |
| DE (1) | DE2841824A1 (de) |
| DK (1) | DK346179A (de) |
| ES (1) | ES483787A1 (de) |
| FR (1) | FR2436782A1 (de) |
| GB (1) | GB2033379B (de) |
| HU (1) | HU182612B (de) |
| IL (1) | IL58273A0 (de) |
| IT (1) | IT1165288B (de) |
| LU (1) | LU81703A1 (de) |
| NL (1) | NL7905267A (de) |
| PL (1) | PL119374B1 (de) |
| RO (1) | RO78587A (de) |
| SU (1) | SU988191A3 (de) |
| YU (1) | YU204879A (de) |
| ZA (1) | ZA795021B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2845454A1 (de) * | 1977-11-01 | 1979-05-10 | Chevron Res | 3-(n-acyl-n-arylamino)- gamma -butyrolactone und - gamma -butyrothiolactone sowie fungizide mittel |
| JPH02124375U (de) * | 1989-03-27 | 1990-10-12 |
-
1978
- 1978-09-22 DE DE19782841824 patent/DE2841824A1/de not_active Withdrawn
-
1979
- 1979-07-05 NL NL7905267A patent/NL7905267A/nl not_active Application Discontinuation
- 1979-08-17 DK DK346179A patent/DK346179A/da not_active Application Discontinuation
- 1979-08-20 CS CS795676A patent/CS219905B2/cs unknown
- 1979-08-21 IT IT25202/79A patent/IT1165288B/it active
- 1979-08-21 YU YU02048/79A patent/YU204879A/xx unknown
- 1979-08-24 BR BR7905455A patent/BR7905455A/pt unknown
- 1979-08-31 ES ES483787A patent/ES483787A1/es not_active Expired
- 1979-09-12 DD DD79215492A patent/DD145989A5/de unknown
- 1979-09-17 GB GB7932156A patent/GB2033379B/en not_active Expired
- 1979-09-19 IL IL58273A patent/IL58273A0/xx unknown
- 1979-09-20 LU LU81703A patent/LU81703A1/de unknown
- 1979-09-20 PL PL1979218428A patent/PL119374B1/pl unknown
- 1979-09-21 BG BG044915A patent/BG30624A3/xx unknown
- 1979-09-21 AT AT0622679A patent/AT365890B/de not_active IP Right Cessation
- 1979-09-21 ZA ZA00795121A patent/ZA795021B/xx unknown
- 1979-09-21 AU AU51076/79A patent/AU5107679A/en not_active Abandoned
- 1979-09-21 SU SU792817359A patent/SU988191A3/ru active
- 1979-09-21 RO RO7998732A patent/RO78587A/ro unknown
- 1979-09-21 BE BE0/197256A patent/BE878924A/fr not_active IP Right Cessation
- 1979-09-21 JP JP12092979A patent/JPS5545682A/ja active Pending
- 1979-09-22 HU HU79SCHE692A patent/HU182612B/hu unknown
- 1979-09-24 FR FR7923680A patent/FR2436782A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2841824A1 (de) | 1980-04-03 |
| DK346179A (da) | 1980-03-23 |
| FR2436782A1 (fr) | 1980-04-18 |
| PL218428A1 (de) | 1980-07-14 |
| BR7905455A (pt) | 1980-05-20 |
| AT365890B (de) | 1982-02-25 |
| FR2436782B1 (de) | 1983-07-22 |
| IL58273A0 (en) | 1979-12-30 |
| IT7925202A0 (it) | 1979-08-21 |
| GB2033379A (en) | 1980-05-21 |
| SU988191A3 (ru) | 1983-01-07 |
| ATA622679A (de) | 1981-07-15 |
| ZA795021B (en) | 1980-09-24 |
| HU182612B (en) | 1984-02-28 |
| AU5107679A (en) | 1980-04-17 |
| LU81703A1 (de) | 1980-01-24 |
| PL119374B1 (en) | 1981-12-31 |
| GB2033379B (en) | 1982-12-22 |
| BG30624A3 (en) | 1981-07-15 |
| BE878924A (fr) | 1980-03-21 |
| YU204879A (en) | 1983-02-28 |
| DD145989A5 (de) | 1981-01-21 |
| ES483787A1 (es) | 1980-05-16 |
| JPS5545682A (en) | 1980-03-31 |
| IT1165288B (it) | 1987-04-22 |
| RO78587A (ro) | 1982-03-24 |
| NL7905267A (nl) | 1980-03-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3937840A (en) | Compositions and methods of combatting bacteria and fungi using 2-methylbenzanilide derivatives | |
| EP0268892A2 (de) | Substituierte Amido-Derivate, Verfahren zu deren Herstellung und diese enthaltende phytopathogenische Fungizide | |
| US4123554A (en) | Fungicidal and germicidal benzanilides | |
| KR100408378B1 (ko) | 살충제 및 진드기구충제로서의 n-아릴티오히드라존 유도체 | |
| CS219905B2 (en) | Fungicide means and method of making the active agents | |
| JPS6019901B2 (ja) | 新規な置換したコハク酸イミドおよび該イミドを含有する殺菌剤 | |
| US4023956A (en) | Amide phosphorothiolate herbicides | |
| US4289886A (en) | Imides derived from 2-thioxo-3-benzox(thia)azoline acetic, and propionic acids | |
| US4154826A (en) | Thiophosphorylguanidines for combating pests | |
| SU849976A3 (ru) | Фунгицидоинсектицидное средство | |
| SE442868B (sv) | Cyklopropankarbonsyraanilider med fungicid verkan samt deras anvendning i fungicida medel | |
| US4185990A (en) | Imides derived from 2-oxo-3-benzothiazolineacetic acid and butyric acid | |
| US4101672A (en) | Microbicidal alanine thioesters | |
| JPS599521B2 (ja) | 除草剤 | |
| US4422865A (en) | Imides derived from 2-thioxo-3-(benzox (thia) azoline acetic and propionic acids | |
| GB1603758A (en) | Fungicidally active furancarboxylic acid anilides and their manufacture and use | |
| CN118994034A (zh) | 一种芳基尿嘧啶类化合物及其制备方法和农药组合物 | |
| KR810001153B1 (ko) | 사이클로프로판 카복실산 아닐리드류의 제조방법 | |
| JPS6054954B2 (ja) | ジフエニルエ−テル誘導体,およびジフエニルエ−テル誘導体を含有する除草剤 | |
| US4086360A (en) | Phenyl thiol carbanilide derivatives, method for the preparation thereof and use thereof as fungicide for agriculture | |
| NO139150B (no) | Herbicid middel inneholdende oximestere | |
| KR810000874B1 (ko) | 우레아 유도체의 제조방법 | |
| KR100342947B1 (ko) | 제초활성 아릴피페라진아미드 유도체 | |
| JPS58170794A (ja) | ホスホロチオエ−ト誘導体および農園芸用殺菌剤 | |
| KR810001171B1 (ko) | 푸란 카복실산 아닐리드류의 제조방법 |