GB2033379A - Fungicidally active acetic acid anilides and their manufacture and use - Google Patents
Fungicidally active acetic acid anilides and their manufacture and use Download PDFInfo
- Publication number
- GB2033379A GB2033379A GB7932156A GB7932156A GB2033379A GB 2033379 A GB2033379 A GB 2033379A GB 7932156 A GB7932156 A GB 7932156A GB 7932156 A GB7932156 A GB 7932156A GB 2033379 A GB2033379 A GB 2033379A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxoperhydro
- furyl
- acid
- anilide
- compound
- 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.)
- Granted
Links
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical class CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- -1 C3-C6-alkynyl Chemical group 0.000 claims abstract description 102
- 238000002360 preparation method Methods 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 241000233866 Fungi Species 0.000 claims abstract description 19
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims abstract description 19
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 15
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 49
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 claims description 47
- 239000013543 active substance Substances 0.000 claims description 28
- MLXDUYUQINCFFV-UHFFFAOYSA-N 2-acetyloxyacetic acid Chemical compound CC(=O)OCC(O)=O MLXDUYUQINCFFV-UHFFFAOYSA-N 0.000 claims description 18
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 claims description 16
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- MAVJUNGOXMOQON-UHFFFAOYSA-N 2-(2-chloroacetyl)oxyacetic acid Chemical compound OC(=O)COC(=O)CCl MAVJUNGOXMOQON-UHFFFAOYSA-N 0.000 claims description 4
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- IXOFPUCWZCAFJX-UHFFFAOYSA-N 2-phenylethanethioic s-acid Chemical compound SC(=O)CC1=CC=CC=C1 IXOFPUCWZCAFJX-UHFFFAOYSA-N 0.000 claims description 3
- FTHCMTYOZSIHJL-UHFFFAOYSA-N 2-propan-2-ylsulfanylacetic acid Chemical compound CC(C)SCC(O)=O FTHCMTYOZSIHJL-UHFFFAOYSA-N 0.000 claims description 3
- QMOJWZIWHSGMFV-UHFFFAOYSA-N CC(CC1N(C(COC)=O)C2=CC(F)=CC=C2)OC1=O Chemical compound CC(CC1N(C(COC)=O)C2=CC(F)=CC=C2)OC1=O QMOJWZIWHSGMFV-UHFFFAOYSA-N 0.000 claims description 3
- CYEZXINASDCBPY-UHFFFAOYSA-N ClC=1C=C(N(C(COC)=O)C2C(OC(C2)C)=O)C=CC1 Chemical compound ClC=1C=C(N(C(COC)=O)C2C(OC(C2)C)=O)C=CC1 CYEZXINASDCBPY-UHFFFAOYSA-N 0.000 claims description 3
- HRPTUFCYVHNLDA-UHFFFAOYSA-N O=C1OCCC1N(C1=CC=CC=C1)C(COC)=O Chemical compound O=C1OCCC1N(C1=CC=CC=C1)C(COC)=O HRPTUFCYVHNLDA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
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- WSISAYKTDHDODI-UHFFFAOYSA-N CC1=C(N(C(CSC2=C(C=CC=C2)N)=O)C2C(OCC2)=O)C(=CC=C1)C Chemical compound CC1=C(N(C(CSC2=C(C=CC=C2)N)=O)C2C(OCC2)=O)C(=CC=C1)C WSISAYKTDHDODI-UHFFFAOYSA-N 0.000 claims description 2
- XGZMVLOHDDIMDC-UHFFFAOYSA-N O=C1OCCC1N(C1=CC=CC=C1)C(COC(C)=O)=O Chemical compound O=C1OCCC1N(C1=CC=CC=C1)C(COC(C)=O)=O XGZMVLOHDDIMDC-UHFFFAOYSA-N 0.000 claims description 2
- AXXZTQVGEQAQLY-UHFFFAOYSA-N O=C1OCCC1N(C1=CC=CC=C1)C(COC1=CC=CC=C1)=O Chemical compound O=C1OCCC1N(C1=CC=CC=C1)C(COC1=CC=CC=C1)=O AXXZTQVGEQAQLY-UHFFFAOYSA-N 0.000 claims description 2
- ZXNDKLCUMRKMFL-UHFFFAOYSA-N O=C1OCCC1N(C1=CC=CC=C1)C(COCC)=O Chemical compound O=C1OCCC1N(C1=CC=CC=C1)C(COCC)=O ZXNDKLCUMRKMFL-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004799 bromophenyl group Chemical group 0.000 claims description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
- MZGNSEAPZQGJRB-UHFFFAOYSA-N dimethyldithiocarbamic acid Chemical compound CN(C)C(S)=S MZGNSEAPZQGJRB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000006178 methyl benzyl group Chemical group 0.000 claims description 2
- 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 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 125000004436 sodium atom Chemical group 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000001511 capsicum annuum Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 235000005489 dwarf bean Nutrition 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 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
- 239000012071 phase Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N (2,6-Me2C6H3)NH2 Natural products CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 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
- CSGYOTJDPQKSIC-UHFFFAOYSA-N 2-propan-2-ylsulfonylacetic acid Chemical compound CC(C)S(=O)(=O)CC(O)=O CSGYOTJDPQKSIC-UHFFFAOYSA-N 0.000 description 1
- QNCHSVFDXFQFLD-UHFFFAOYSA-N 3-(2,6-dimethylanilino)oxolan-2-one Chemical compound CC1=CC=CC(C)=C1NC1C(=O)OCC1 QNCHSVFDXFQFLD-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- UKKYMRZUZVPUGW-UHFFFAOYSA-N CC(C=CC=C1C)=C1N(C(CCO1)C1=O)C(CSCC1=CC=CC=C1)=O Chemical compound CC(C=CC=C1C)=C1N(C(CCO1)C1=O)C(CSCC1=CC=CC=C1)=O UKKYMRZUZVPUGW-UHFFFAOYSA-N 0.000 description 1
- CQABKVQVZHOCGR-UHFFFAOYSA-N CC1=C(N(C(CC(C)C)=S)C2C(OCC2)=O)C(=CC=C1)C Chemical compound CC1=C(N(C(CC(C)C)=S)C2C(OCC2)=O)C(=CC=C1)C CQABKVQVZHOCGR-UHFFFAOYSA-N 0.000 description 1
- ZPIDIMFEUSANFK-UHFFFAOYSA-N CC1=C(N(C(CC2=CC=CC=C2)=S)C2C(OCC2)=O)C(=CC=C1)C Chemical compound CC1=C(N(C(CC2=CC=CC=C2)=S)C2C(OCC2)=O)C(=CC=C1)C ZPIDIMFEUSANFK-UHFFFAOYSA-N 0.000 description 1
- YLCVOJLWRIULOM-UHFFFAOYSA-N CC1=C(N(C(CCC)=S)C2C(OCC2)=O)C(=CC=C1)C Chemical compound CC1=C(N(C(CCC)=S)C2C(OCC2)=O)C(=CC=C1)C YLCVOJLWRIULOM-UHFFFAOYSA-N 0.000 description 1
- AFOJUCRLNNSEOL-UHFFFAOYSA-N CC1=C(N(C(COC)=O)C2C(OC(C2)CCCC)=O)C(=CC=C1)C Chemical compound CC1=C(N(C(COC)=O)C2C(OC(C2)CCCC)=O)C(=CC=C1)C AFOJUCRLNNSEOL-UHFFFAOYSA-N 0.000 description 1
- GZEWCKDSSMCBME-UHFFFAOYSA-N CC1=C(N(C(COC2=CC=CC=C2)=O)C2C(OCC2)=O)C=CC=C1C Chemical compound CC1=C(N(C(COC2=CC=CC=C2)=O)C2C(OCC2)=O)C=CC=C1C GZEWCKDSSMCBME-UHFFFAOYSA-N 0.000 description 1
- QHTWHEFJWKUDET-UHFFFAOYSA-N CC1=C(N(C(COCC)=O)C2C(OC(C2)C)=O)C(=CC=C1)C Chemical compound CC1=C(N(C(COCC)=O)C2C(OC(C2)C)=O)C(=CC=C1)C QHTWHEFJWKUDET-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
- GUDHLABGKGUOMR-UHFFFAOYSA-N COC1=C(N(C(COC)=O)C2C(OCC2)=O)C=CC=C1 Chemical compound COC1=C(N(C(COC)=O)C2C(OCC2)=O)C=CC=C1 GUDHLABGKGUOMR-UHFFFAOYSA-N 0.000 description 1
- 235000002567 Capsicum annuum Nutrition 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001633993 Cineraria Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NPKXFJDIGYRPFV-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-2-methoxy-N-(5-methyl-2-oxooxolan-3-yl)acetamide Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)C1CC(C)OC1=O NPKXFJDIGYRPFV-UHFFFAOYSA-N 0.000 description 1
- 241000410021 Pericallis cruenta Species 0.000 description 1
- 241000233616 Phytophthora capsici Species 0.000 description 1
- 241000233629 Phytophthora parasitica 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
- 241000232168 Sinningia Species 0.000 description 1
- 244000093304 Sinningia speciosa Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- NHIXZWJEGJQZRA-UHFFFAOYSA-N [2-[2-chloro-6-[(2-oxooxolan-3-yl)amino]phenyl]-2-oxoethyl] N,N-dimethylcarbamodithioate Chemical compound ClC1=C(C(NC2C(OCC2)=O)=CC=C1)C(=O)CSC(N(C)C)=S NHIXZWJEGJQZRA-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols 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
- 150000003931 anilides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZXSBDSGRQIWJPM-UHFFFAOYSA-N dimethylcarbamothioic s-acid Chemical compound CN(C)C(S)=O ZXSBDSGRQIWJPM-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000007789 gas Substances 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
- 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
- 239000004571 lime Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 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
- 230000003449 preventive effect Effects 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 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
- 239000011541 reaction mixture 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
- 239000007858 starting material Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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)
Abstract
Novel acetic acid anilides of the general formula I <IMAGE> (wherein R1 represents H or C1-C4- alkyl, R2 represents aromatic hydrocarbon optionally substituted by one or more substituents selected from C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, Hal, -CF3, -NO2, C1-C4-alkoxycarbonyl and -CN, R3 represents C1-C6-alkyl, halogeno- C1-C6-alkyl, C1-C4-alkoxy-C1-C4- alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl or halogeno- C1-C6-alkoxycarbonyl, or represents phenyl or benzyl optionally substituted by one or more substituents selected from Hal, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, -CF3, -NO2 and -NH2, or represents amidino or dimenthylthiocarbamoyl, and X represents O, S, SO or SO2) and acid addition salts of such compounds in which R3 represents amidino, have a fungicidal action against phytopathogenic fungi and accordingly may be made up with suitable carriers into fungicidal preparations and may be used for protecting living plants, crop areas and seeds against such fungi.
Description
SPECIFICATION
Fungicidally active acetic acid anilides and their manufacture and use
The present invention is concerned with new acetic acid anilides, with processes for the manufacture of these compounds and with the use of these compounds for controlling phytopathogenic fungi.
Agents for controlling phytopathogenic fungi are already known. Agents of this kind known in practice are, for example, tetramethylthiuram disulphide (German Patent Specification No. 642,532) and manganese ethylene bisdithiocarbamate (United States Patent Specification No. 2,504, 404).
The probiem upon which the present invention is based has been to develop new fungicides having a good action against leaf and soil fungi.
This problem is now solved by the new compounds of the present invention, as defined below.
The present invention provides compounds of the general formula I
in which R1 represents a hydrogen atom or a C1-C4-alkyl group,
R2 represents an unsubstituted aromatic hydrocarbon group or an aromatic hydrocarbon group substituted by one or more substituents selected from C1-C4-alkyl groups, C1-C4-alkoxy groups, C1-C4-alklthio groups, halogen atoms, trifluoromethyl groups, nitro groups, C1-C4-alkoxycarbonyl groups and cyano groups,
R3 represents a C,--Cdalkyl, halogeno-C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl or halogeno-C1-C6-alkylcarbonyl group, or represents an unsubstituted phenyl or benzyl group or a phenyl orgenzyl group substituted by one or more substituents selected from halogen atoms and C144-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, trifluoromethyl, nitro and amino groups, or represents an amidino or dimethyithiocarbamoyl group, and
X represents an oxygen or sulphur atom or a sulphinyl or sulphonyl group, and acid addition salts of such compounds in which R3 represents an amidino group.
When R2 represents an aromatic hydrocarbon group substituted by more than one substituent, these substituents may be the same or different. Similarly, when R3 represents a phenyl or benzyl group substituted by more than one substituent, these may be the same or different.
The compounds of the present invention are, surprisingly, superior to the known agents of the kind mentioned above in their action against phytopathogenic fungi and, in addition, they possess a good plant tolerability and a sufficient duration of action. In the application quantities that come into consideration in practice they do not act phytotoxically and there is, therefore, no risk of plant growth being adversely affected if they are used. Thanks to these advantageous properties, these compounds can therefore be used in agriculture and in horticulture for treating the soil and the ground and can also be applied to foliage.
The compounds of the present invention are distinguished by an outstanding action against a great number of pathogenic fungi, for example Pythium, Phytophthora, Plasmopara, Piricularia and
Botrytis.
In contrast to agents that have only a preventive action such as, for example, manganese ethylene bisdithiocarbamate, the compounds of the present invention possess, the exceptional advantage of a curative and systemic action and, therefore, make it possible to control also fungi that have already penetrated into the plants.
The present invention accordingly also provides a fungicidal preparation which comprises one or more compounds selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group, in admixture or conjunction with a suitable carrier.
The present invention further provides a method of protecting a living plant against phytopathogenic fungi, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with one or more compounds selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group.
The present invention further provides a method of protecting a crop area against phytopathogenic fungi, wherein the crop area is treated with one or more compounds selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group.
The present invention further provides a method of dressing seeds, wherein the seeds are treated with one or more compounds selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group.
The present invention further provides a pack which comprises one or more compounds selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group, together with instructions for its/their use for controlling phytopathogenic fungi.
The compounds of the present invention that are distinguished by a very good fungicidal action are especially those of the general formula I in which
R, represents a hydrogen atom or a methyl or ethyl group, R2 represents a phenyl, methylphenyl, dimethylphenyl, methoxyphenyl, fluorophenyl, chlorophenyl, bromophenyl, dichlorophenyl, trifluoromethylphenyl, methylthiophenyl or cyanophenyl group, R3 represents a methyl, ethyl, propyl, isopropyl, tert.-butyl, allyl, propenyl, propynyl, methoxyethyl, benzyl, chlorobenzyl, methylbenzyl, methoxybenzyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl, acetyl orchloracetyl group, and
X represents an oxygen or sulphur atom or a sulphinyl or sulphonyl group.
The compounds of the present invention may be applied singly, or in the form of mixtures with one
another or with other active substances. If desired, other fungicides, nematocides, insecticides or other
kinds of pesticides may be added, depending on the desired aim.
The active substances are advantageously applied in the form of fungicidal preparations, for example powders, strewable preparations, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid vehicles or diluents and, if desired, of surface-active agents, for example wetting, adhesive, emulsifying and/or dispersing agents.
Suitable liquid carriers are water, mineral oils, or other organic solvents, for example xylene, chlorobenzene, cyclohexanol, dioxan, acetonitrile, ethyl acetate, dimethylformamide, isophorone and dimethyl sulphoxide.
Suitable solid carriers are, for example, lime, kaolin, chalk, talcum, attaclay and other clays as well as natural or synthetic silicic acid.
As surface-active agents there may be mentioned, for example, salts of ligninsulphonic acids, salts of alkylated benzenesulphonic acids, sulphonated acid amides and salts thereof, polyethoxylated amines and alcohols.
When the active substances are to be used for dressing seeds, dyestuffs may also be added in order to give the dressed seeds a clearly visible colour.
The proportion of active substance(s) in the fungicidal preparations may vary within wide limits, the exact concentration of the active substances used for the preparations being dependent primarily on the quantity in which the preparations are to be used. The preparations may contain, for example, between approximately 1 and 80% by weight, preferably between 20 and 50% byweight of active substance(s) and approximately 99 to 20% by weight of liquid or solid carrier and also, if desired, up to 20% by weight of surface-active agent(s).
The active substances may be applied in the usual manner, for example, by spattering, by spraying using a course spray or a spray in the form of a fine mist, by dusting, by applying in the form of a gas, or by fumigating, scattering, drenching or dressing.
The new compounds of the general formula I may be manufactured, for example, by the processes of the present invention, as defined below.
The present invention further provides a process for the manufacture of a compound of the general formula I, wherein a compound of the general formula II
in which R, and R2 have the meanings given above, is reacted in an organic solvent, if desired in the presence of an acid acceptor, with an acid halide of the general formula Ill Hal-CO-CH2-X-Fl3 (III), in which R3 and X have the meanings given above and Hal represents a halogen atom, preferably a chlorine atom. The process product may be isolated in a manner known per se.
The present invention further provides a process for the manufacture of those compounds of the general formula I in which X represents a sulphur atom, wherein a compound of the general formula V
in which R, and R2 have the meanings given above and Hal represents a halogen atom, preferably a chlorine atom, is reacted in an inert organic solvent under nitrogen with a compound of the general formula (-)
B S-Fl3, in which R3 has the meaning given above and B represents an alkali metal atom, preferably a sodium atom, or, when R3 represents an amidino group, with thiourea of the formula
The compound of the general formula V has advantageously been prepared by reacting in an organic solvent, if desired in the presence of an acid acceptor, a compound of the general formula II
in which R1 and R2 have the meanings given above, with an acid halide of the general formula IV Hal'CO < H2Hal (IV), in which Hal and Hal' each represents a halogen atom, preferably a chlorine atom.
The present invention further provides a process for the manufacture of those compounds of the general formula I in which X represents a sulphinyl orsulphonyl group, wherein a compound of the general formula la
in which Fl1, R2 and R3 have the meanings given above, is reacted in a solvent with an oxidizing agent.
The compound of the general formula la may of course have been prepared by one of the other processes of the present invention, as defined above, starting from a compound of the general formula
II or V.
A compound of the general formula I, in which R3 represents an amidino group, obtained by any one of the processes of the present invention, as defined above, may, if desired, be converted into an acid addition salt, for example the hydrochloride, thereof.
As acid acceptors which may optionally be used, there may be mentioned for example, organic bases, for example pyridine, triethylamine or N,N-dimethylaniline, or inorganic bases, for example hydroxides, oxides and carbonates of alkali metals and alkaline earth metals.
As solvents there may be used organic solvents, for example ether, tetrahydrofuran, benzene, toluene, xylene, ethyl acetate, acetonitrile, dimethylformamide or dimethyl sulphoxide. The reactions are advantageously carried out at temperatures of between --150C and 1 500C.
The reaction of the compounds of the general formula la to form the compounds of the general formula I, in which X represents a sulphinyl or sulphonyl group, may be carried out with oxidizing agents, for example with organic peracids, for example 3-chloroperbenzoic acid, in an inert organic solvent, for example methyl chloride or chloroform, or with inorganic reagents, for example hydrogen peroxide or potassium permanganate, at temperatures of between 0 and 1000C, in acetic acid. For preparing the sulphinyl compounds, approximately 2 oxidation equivalents are necessary and in the case of the sulphonyl compounds, approximately 4 oxidation equivalents are necessary.
The compounds of the present invention are generally almost colourless, odourless, crystalline substances or faintly yellow liquids, which are very sparingly soluble in water and benzine, but, in contrast, very readily soluble in polar solvents, for example acetone, dimethylformamide and dimethyl sulphoxide.
The starting compounds for manufacturing the compounds of the present invention are known per se or may be prepared by processes known per se.
The following Examples illustrate the invention. Examples 1 to 5 illustrate the manufacture of the
compounds of the present invention and Examples 6 to 12 illustrate the possible ways of using the compounds of the present invention and their superiorfungicidal action.
EXAMPLE 1
Methoxyacetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide] A mixture consisting of 9.75 g (0.47 mole) of 3-(2,6-dimethylaniline)-perhydrofuran-2-one, 6.50 g
(0.06 mole) of methoxyacetyl chloride, 250 ml of toluene and 2 ml of dimethylformamide was stirred for 3 hours at 250C and then for one hour at the boiling temperature. The mixture was then
concentrated to dryness in vacuo and the solid residue was digested with diisopropyl ether. After
removing the crystals by suction, they were dried at 250C in vacuo.
Yield: 11.5 g = 88% of the theoretical yield.
,M.p.: 130-1310C.
EXAMPLE 2.
Acetoxyacetic acid [2 ,6-dimethyl-N-(2-oxoperhydro-3-fu ryl)-a nilide]
To 10.26 g (0.05 mole) of 3-(2,6-dimethylanilino)-perhydrofuran-2-one, dissolved in 200 ml of toluene, there were added 6.85 g (0.05 mole) of acetoxyacetic acid chloride and the mixture was
heated at the boil for one hour. The reaction solution was then concentrated to dryness in vacuo. The oil
remaining behind was crystallized by rubbing with ether. The crystals were removed by suction and
washed several times with a little ether and the resulting substance was dried at approximately 250C in
vacuo.
Yield: 12.64 g = 82.8% of the theoretical yield.
M.p.: 106-1080C.
EXAMPLE 3.
Methylthio-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-fu ryl)-anilidej 28.17 g (0.1 mole) of chloracetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilidej were dissolved in 120 ml of acetonitrile, and 6.5 g (0.15 mole) of sodium methylate were added thereto. The mixture was cooled to approximately -1 50C and 22.4 g (0.47 mole) of methyl mercaptan were added, while stirring. After slowly warming the mixture to 200C to 250C, it was then further stirred at this temperature for approximately twenty hours. It was then taken up in ethyl acetate/water and the
alkaline aqueous phase was separated off. The organic phase was extracted once by shaking with a sodium hydroxide solution and then washed until neutrai. The ethyl acetate phase was dried over
magnesium sulphate; filtered off and concentrated in vacuo.The oily residue was dried under an oil
pump vacuum.
Yield: 18 g = 61.3% of the theoretical yield.
M.p.: 71--73 OC.
EXAMPLE 4 lsopropylsu Iphonyl-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-a nilide]
9.64 g (0.03 mole) of isopropyithio-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilidej were dissolved in 260 ml of chloroform, and 12.08 g (0.07 mole) of 3-chloroperbenzoic acid were
added thereto. After stirring the mixture for four hours at room temperature, a further 6 g (0.035 mole)
of 3-chloroperbenzoic acid were added. Stirring was continued for approximately 14 hours and the
organic phase was extracted several times by shaking with a 1 N sodium hydroxide solution, dried over
magnesium sulphate and concentrated in vacuo. The resulting crystals were digested with isoether and filtered off with suction.
Yield: 9 g = 84.9% of the theoretical yield.
M.p.: 177-1850C.
EXAMPLE 5
Dimethyldithioca rbamic acid [2,6-dimethyl-N-(2-oxoperhydro-3-fu ryl)-anilinoca rbonylmethyl] ester.
8.45 g (0.03 mole) of chloracetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide] were
dissolved in 100 ml of acetonitrile and, after the addition of 5.3 g (0.037 mole) of sodium dimethyl
dithiocarbamate, heated at the boil for 6 hours while passing nitrogen through it. After having cooled to
approximately 20-250C, the reaction mixture was poured into 400 ml of water and extracted 3 times
with chloroform. The combined chloroform phases were dried over magnesium sulphate and
concentrated in vacuo. The crystalline residue was filtered off with suction, washed with methanol and
dried at room temperature in vacuo.
Yield: 7.7 g = 70% of the theoretical yield.
M.p.: 153-1560C.
Each of the following compounds of the present invention may be manufactured in a manner similar to that described in any of the appropriate Examples above.
Name of the compound Physical constant
Methoxyacetic acid [3-chloro-N (2-oxoperhydro-3-furyl)-anilide] M.p.:
Methoxyacetic acid [2,6-dimethyl-N
(5-methyl-2-oxoperhydro-3-furyl)-anilide] M.p.: 113-1 140C Methoxyacetic acid [N-(2-oxoper
hydro-3-furyl)-anilide] M.p.: 65--66 C
Methoxyacetic acid [3-methyl-N (2-oxoperhydro-3-fu ryl)-anilide] M.p.: 115-1160C Methoxyacetic acid [2,3-dimethyl-N
(2-oxoperhydro-3-furyl)-anilide] M.p.: 105-1060C Methoxyacetic acid [3-fluoro-N-( 5-methyl- 2-oxoperhydro-3-furyl)-anilide] M.p.: 75-760C Methoxyacetic acid [3-chloro-N-(5-methyl
2-oxoperhydro3-furyl)-anilide] M.p.: 81--83 C
Methoxyacetic acid [2-methyl-N
(2-oxope rhyd ro3-fu ryl)-a n i lide] M.p.: 66-670C Methoxyacetic acid [2-methoxy-N (2-oxoperhydro-3-fu ryl)-anilide] M.p.: 95--97 C Methoxya cetic acid [3-chloro-2-methyl-N (2-oxoperhydro-34ury1)-anilide] M.p.: 106-108 C
Methoxyacetic acid [3-cyano-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 93-940C Acetoxyacetic acid [3-methyl-N
(2-oxoperhydro-3-furyl)-anilide] M.p.: 99-1030C Acetoxyacetic acid [N-(2-oxoper hydro-3-furyl)-anilide] M.p.: 127-1280C Acetoxyacetic acid [3-bromo-N
(2-oxoperhydro-3-furyl)-anilide] M.p.: 137-1380C Acetoxyacetic acid [2,3-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 97-980C Acetoxyacetic acid [3-fluoro-N (2-oxoperhydro-3-fu ryl)-anilide] M.p.: 96-980C Acetoxyacetic acid [3-cyano-N
2-oxoperhydro-3-furyl)-anilide] M.p.:: 140-1410C Acetoxyacetic acid [2-methyl-N (2-oxoperhyd ro-3-fu ryl)-a nilide] M.p.: 119-1200C Acetoxyacetic acid [3-chloro-N (2-oxoperhyd ro-3-furyl)-a nilide] M.p.: 123-1240C Name of the compound Physical constant
Acetoxyacetic acid [3-cyano-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 118-1200C Phenylthio-acetic acid [2,6-dimethyl N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 103--105 C Ethylthio-acetic acid [2,6-dimethyl
N-(2-oxoperhydro-3-furyl)-anilide] nD20: 1.5552
Isopropylthio-acetic acid [2 ,6-dimethyl
N-(2-oxoperhydro-3-furyl)-anilide] n2g: 1.5490 tert.-Butylthio-acetic acid [2,6-dimethyl-
N-(2-oxoperhydro-3-furyl)-anilide] n20: 1.5400
S-[3-Chloro-N-(2-oxoperhydro-3-fu ryl)anilinocarbonylmethyl]-thiuronium chloride M.p.: 1900C
(with decomposition) Dimethyldithiocarbamic acid [3-chloro
N-(2-oxoperhydro-3-furyl)-anilino- carbonylmethyl] ester M.p.: 1260C Dimethylthiocarbamic acid [3-fluoro N-(2-oxoperhydro-3-furyl)-a nilino carbonylrr,ethy!] ester M.p.: 160-1610C (3-Methylphenylthio)-acetic acid [2,6-dimethyl N-(2-oxoperhydro-3-furyl)-anilide] n2g: 1.5950 (Benzylthio)-acetic acid [2,6-dimethyl
N-(2-oxoperhydro-3-furyl)-anilide] n2g 1.5720 (2-Aminophenylthio)-acetic acid [2,6dimethyl-N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 150-151 0C Ch loracetoxyacetic acid [2,6-dimethyl
N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 11 5-11 80C Phenoxyacetic acid [2,6-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 92-930C Chloracetoxyacetic acid [N (2-oxoperhydro-3-furyl)-anilide] M.p.: 64 C.
Chloracetoxyacetic acid [3-methyl
N-(2-oxoperhydrn-34uryl)-anilide] M.p.: 82-830C Chloracetoxyacetic acid [3-bromo N-(2-oxoperhydro-3-furyl)-anilide] M.p.:124-125 C 250C Phenoxyacetic acid [3-bromo-N (2-oxoperh; dro-3-furyl)-anilide] M.p.:114 C
Phenoxyacetic acid [N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 120-1210C Phenoxyacetic acid [2,3-dimethyl N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 80-820C Phenoxyacetic acid [3-methyl-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 87-890C Name of the compound Physical constant
Phenoxyacetic acid [2-methyl-N (2-oxoperhydro-3-fu ryl)-anilide] M.p.: 112-1130C Phenoxyacetic acid [3-chloro-N (2-oxoperhydro-3-furyl)-anilide] M.p.:: 93-950C Chloracetoxyacetic acid[3-chloro N-(2-oxoperhydro-3-furyl)-anilide] M.p.:102-103 OC Phenoxyacetic acid [2,6-dimethyl-N-(5 methyl-2-oxoperhydro-3-furyl)-anilide] M.p.: 142--1430C Chloracetoxyacetic acid [2,6-dimethyl-N (5-methyl-2-oxoperhydro-3-furyl)-anilide] M.p.: 94-970C S-[2,6-Dimethyl-N-(2-oxoperhydro-3-fu ryi) anilinocarbonylmethyI]-thiurnnium chloride M.p.: 26qOC (with decompositfon) Ethoxyacetic acid [2,6-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 63CC Ethoxyacetic acid [2,6-dimethyl-N-(5 methyl-2-oxoperhydro-3-furyl)-anilide] M.p.:: 82-830C Ethoxyacetic acid [3-chloro-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 100--201 C
Ethoxyacetic acid [N-(2-oxoperhydro 3-furyl)-anilide] M.p.: 62-640C Ethoxyacetic acid [3-bromo-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 115-1160C Ethoxyacetic acid [3-methyl-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 74 76 C Ethoxyacetic acid [5-chloro-2-methyl
N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 101-103 0C Ethoxyacetic acid [2-chloro-N (2-oxoperhyd ro-3-furyl)-anilide] n2g: 1.5387
Methoxyacetic acid [2,6-dimethyl-N-(5butyl-2-oxoperhydro-3-furyl)-anilide] M.p.:: 80-81 "C Methoxyacetic acid [4-chloro-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 105-1060C EXAMPLE 6
Limiting concentration test in the control of Pythium ultimum
In a series of tests 20% strength pulverulent active substance preparations were mixed uniformly with soil that was severely infected with Pythium ultimum. The treated soil was placed in clay dishes each having a 0.5 litre capacity and, without a waiting period, 20 marrowfat pea seeds (Pisum sativum
L. convar. medullareAlef.) of the "Kelvedon Wonder" variety were sown in each dish. After a cultivation period of three weeks at 20 to 240C in a greenhouse the number of healthy peas was determined and an assessment (1-4 as defined below) of the roots was carried out.
The active substances used and their application quantities, and also the results, are given in the following Table.
Root assessment:
4 = white roots without fungal necroses
3 = white roots with slight fungal necroses
2 = brown roots with fairly severe fungal necroses
1 = severe fungal necroses, mouldy roots.
Active substance Root
concentration in Number of assessment
Compound according to the invention mg/l of soil healthy peas (14) Methoxyacetic acid [2,6-dimethyl-N- 20 mg 1 7 4 (2-oxoperhydro-3-furyl)-anilide] 40 mg 1 5 4
80 mg 17 4
Methoxyacetic acid [3-chloro-N- 20 mg 1 7 4 (2-oxoperhydro-3-furyl)-anilide] 40 mg 1 5 4
80 mg 18 4
Methoxyacetic acid [2,6-dimethyl-N- 20 mg 1 7 4 (5-methyl-2-oxoperhydro-3-furyl)- 40 mg 1 7 4 anilide] 80 mg 16 4
Methoxyacetic acid [N-(2-oxoperhydro- 20 mg 1 7 4 3-furyl)-anilide] 40 mg 17 4
80 mg 17 4
Methoxyacetic acid [3-methyl-N- 20 mg 18 4 (2-oxoperhydro-3-furyl)-anilide] 40 mg 18 4
80 mg 19 4
Methoxyacetic acid [2,3-dimethyl-N- 20 mg 20 4 (2-oxoperhydro-3-furyl)-anilide] 40 mg 19 4
80 mg 18 4
Methoxyacetic acid [3-fluoro-N-(5-methyl- 20 mg 1 6 4 2-oxoperhydro-3-furyl)-anilide] 40 mg 1 6 4
80 mg 19 4
Methoxyacetic acid [3-chioro-N-(5-methyl- 20 mg 1 7 4 2-oxoperhydro-3-furyl)-anilide] 40 mg 18 4
80 mg 18 4
Methoxyacetic acid [2-methyl-N- 20 mg 12 3 (2-oxoperhydro-3-furyl)-anilide] 40 mg 16 4
80 mg 17 4
Methoxyacetic acid [2-methoxy-N- 20 mg 18 3 (2-oxoperhydro-3-furyl)-anilide] 40 mg 18 4
80 mg 17 4
Methoxyacetic acid [3-cyano-N- 20 mg 16 4 (2-oxoperhydro-3-furyl)-anilide] 40 mg 18 4
80 mg 18 4
Methoxyacetic acid [3-chloro-2-methyl- 20 mg 18 4 N-(2-oxoperhydro-3-furyl)-anilide] 40 mg 17 4
80 mg 19 4
Acetoxyacetic acid [2,6-dimethyl-N-(5- 20 mg 3 1 methyl-2-oxoperhydro-3-furyl)-anilide] 40 mg 12 1
80mg 18 4
Active substance Root
concentration in Number of assessment
Compound according to the invention mg/l of soil healthy peas (1-4) Acetoxyacetic acid [2,6-dimethyl-N- 20 mg 15 2 (2-oxoperhyd ro-3-furyl)-a nilidel 40 mg 1 6 4 8Omg 18 4
Phenylthio-acetic acid [2,6-dimethyl- 20 mg 8 1
N-(2-oxoperhydro-3-furyl)-anilide] 40 mg 10 2
80mg 19 4
Ethylthio-acetic acid [2,6-dimethyl- 20 mg 1 5 4 N-(2-oxoperhydro-3-furyl)-anilide] 40 mg 1 6 4
80 mg 18 4
Isopropylthio-acetic acid [2!6-dimethyl- 20 mg 1 6 4
N-(2-oxoperhydro-3-furyl)-anilide] 40 mg 1 6 4 80 mug 17 4 Isopropylsulphonylaceticacid 20 mg 1 6 3
[2,6-dimethyl-N-(2-oxoperhydro- 40 mg 1 7 4
3-furyl)-anilide] 80 mg 16 4
AGENT FOR COMPARISON
Manganese ethylene bisdithiocarbamate 20 mg 1 1 40 mg 6 1 8Q mg 9 1
Control 1. (3 repetitions)
Infected soil without treatment a) 1 1
b) O 1 c) O 1 Control ll. (3 repetitions)
Steamed soil a) 17 4
b) 18 4
c) 18 4
EXAMPLE 7
Control of Phytophthora nicotianae var. nicotianae in the pot cultivation of Sinningia speciosa
In a series of tests young Sinningia plants of the "Berliner Rot" variety were potted in clay pots each having a diameter of 11 cm. The potting substrate was a mixture of 1 part peat culture substrate
and 1 part compost soil. After plotting, 100 ml of the preparation under test and having the concentration listed in the Table below were poured once over the plants. Three days later, the pots were uniformly inoculated with mycelium flocci of a three-week-old Phytophthora culture. There then followed a cultivation period of 7 weeks at 22 to 240C in a greenhouse.
The active substances used and their application quantities, and also the results, are given in the following Table.
Plant loss Average fresh
Active substance after weight of plants
Compound according to the invention concentration 7 weeks after 7 weeks
Methoxyacetic acid [2,6-dimethyl- 0.01% 0% 180 g
N-(2-oxoperhydro-3-furyl)-anilide] 0.02% 0% 1 92 g
Methoxyacetic acid [N- 0.01% 0% 176 g (2-oxoperhydro-3-furyl)-anilide] 0.02% 0% 200 g Control 1.
inoculated - 80% 145g Control 11.
not inoculated 0% 184g EXAMPLE 8
Control of Phytophthora parasitica var. nicotianae in tobacco cultivation
In a series of tests young tobacco plants of the "Havana" variety were potted in clay pots each
having a diameter of 1 4 cm. The potting substrate was a mixture of 1 part peat culture substrate and
one part sandy compost soil. After potting, 100 ml of the preparation under test and having the
concentration listed in the Table below were poured once over the plants. Three days later, the pots were uniformly inoculated with mycelium flocci of a four-week-old Phytophthora culture. There then
followed a cultivation period of 4 weeks at 24 to 260C in a greenhouse.
The active substances used and their application quantities, and also the results, are given in the following Table.
Plant loss Average fresh
Active substance after weight of plants
Compound according to the invention concentration 4 weeks after 4 weeks
Methoxyacetic acid [2,6-dimethyl-N-(5- 0.01% 0% 2159 methyl-2-oxoperhydro-3-furyl)-anilide] 0.02% 0% 230 g
Methoxyacetic acid [2,6-dimethyl-N- 0.01% 0% 225 g (2-oxoperhydro-3-furyl)-anilide] 0.02% 0% 227 g Control.
inoculated - 100% Og
Control II.
not inoculated 0% 260 g EXAMPLE 9
Control of Phytophthora capsici in the cultivation of paprika (Capsicum annuum)
In a series of tests young paprika plants were potted in clay pots each having a diameter of 14 cm.
The substrate was a mixture of 1 part peat culture substrate and one part sandy compost soil. Three days after potting, 100 ml of the preparation under test and having the concentration listed in the Table below were poured once over the plants. Three days later, the pots were uniformly inoculated with mycelium flocci of a four-week old Phytophthora culture. There then followed a cultivation period of 4 weeks at 24 to 260C in a greenhouse.
The active substances and their application quantities, and also the results, are given in the following Table.
Active Plant loss
substance after
Compound according to the invention concentration 4 weeks
Methoxyacetic acid [2,6-dimethyl-N- 0.01% 20% (2-oxoperhydro-3 4uryI)-anilide] 0.02% 0%
0.04% 0%
Methoxyacetic acid [3-chloro-N- 0.01% 40% (2-oxoperhydro-3-furyl)-anilide] 0.02% 0%
0.04% 0%
Control I.
inoculated - 100% Control II.
not inoculated 0%
EXAMPLE 10
Control of Phytophthora cryptogaea in the pot cultivation of Senecio cruentus
In a series of tests young Cineraria plants of the "Erfurter Zwerg" variety were potted in clay pots each having a diameter of 11 cm. The potting substrate was a mixture of 1 part peat culture substrate and 1 part sandy compost soil. Three days after potting, 100 ml of the preparation under test and having the concentration listed in the Table below were poured once over the plants. Three days later,
the pots were uniformly inoculated with mycelium flocci of a three-week-old Phytophthora culture.
There then followed a cultivation period of 7 weeks at 20 to 220C in a greenhouse.
The active substances used and their application quantities, and also the results. are given in the
following Table.
Active Plant loss
substance after
Compound according to the invention concentration 7 weeks
Methoxyacetic acid [2 ,6-dimethyl-N- 0.01% 0% (2-oxoperhydro-3-furyl)-anilide] 0.02o/o 0%
Methoxyacetic acid [2 ,6-dimethyl -N -(5- 0.01% 20% methyl-2-oxoperhydro-3-furyl)-anilide] 0,02% 0% Control.
inoculated 100%
Control 11 not inoculated ~ 0% oyO EXAMPLE 11
Dressing of French bean seeds
In a series of tests French bean seeds (Phaseolus vulgaris var. nan us) of the "Wachs Beste von
Ailen" variety were dressed with 20% strength pulverulent active substance preparations. Clay dishes
each of 2 litres capacity (20 x 20 x 5 cm) were filled with normal compost soil (damping-off) and 25 of
the bean seeds were sown in each dish. After a cultivation period of 15 days at 19 to 21 0C in a greenhouse, the number of healthy seedlings was determined.
The active substances used and their application quantities, and also the results, are given in the following Table.
Active substance Yo pf healthy plants Fresh weight
Compound according to the invention in g/kg of seeds from the seeds per plant
Methoxyacetic acid [2,6-dimethyl-N- 0.12 100% 3.8 9 (2-oxoperhydro-3-furyl)-anilide] 0.25 96% 3.9 g
0.50 100% 3.Bg Methoxyacetic acid [3'-chlorn-N- 0.12 100% 4.2 g (2-oxoperhydro-3-furyl)-anilide] 0.25 100% 4.3 g
0.50 100% 3.7 9 Methoxyacetic acid [2,6-dimethyl-N-(5- 0.12 100% 3.8 g
methyl-2-oxoperhydro-3-furyl)-anilide] 0.25 100% 4.2 g
0.50 96% 4.1 g
Active substance % of healthy plants Fresh weight
Compound according to the invention in g/kg of seeds from the seeds per plant
Methoxyacetic acid [N- 0.12 100% 4.0 g (2-oxoperhydro-3-furyl)-anilide] 0.25 100% 4.2 g
0.50 100% 3.9 9 Methoxyacetic acid [3-methyl-N- 0.12 100% 3.6 g (2-oxoperhydro-3-furyl)-anilide] 0.25 100% 4.1 g
0.50 100% 4.2 g
AGENTS FOR COMPARISON
Tetramethylthiuram 0.25 16% 3.2 g disulphide 0.50 68% 3.8 g
1.00 72% 3.3 g Control 1.
Infected soil a) 0%
b) 0% c) 0% Control 11.
Steamed soil a) 96% 4.2 g
b) 100% 4.1 9 c) 100% 4.1 g
EXAMPLE 12
The effect of a prophylactic treatment of the foliage against Plasmopara viticola in vines in a greenhouse
In a series of tests young vines having approximately 5 to 8 leaves were sprayed until dripping wet with an active substance concentration of 0.025% and, after the spray coating had dried, were sprayed on the undersides of the leaves with an aqueous suspension of sporangia of the fungus indicated in the heading above (approximately 20,000 per ml) and then immediately incubated in a greenhouse at 22 to 240C in an atmosphere as saturated with water vapour as possible.
From the second day onwards, the air humidity was reduced to the normal level (30 to 70% saturation) for three to four days and then maintained at water vapour saturation for a further day. The percentage proportion of the surface attacked by fungi of each leaf was then recorded and the average per treatment was calculated as follows to determine the fungicidal effect: 1 00 100. attack in treated plants = % effect
attack in untreated plants
The active substances used and the results are given in the following Table.
Compound according to the invention % Effect
Methoxyacetic acid [2,6-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] 100
Methoxyacetic acid [3-chloro-N (2-oxoperhydro-3-furyl)-anilide] 100
Methoxyacetic acid [2,6-dimethyl-N-(5methyl-2-oxoperhydro-3-furyl)-anilide] 100
Methoxyacetic acid [N-(2-oxoperhydro3-furyl)-anilide] 100
Methoxyacetic acid [3-methyl-N (2-oxoperhydro-3-furyl)-anilide] 100
Compound according to the invention % Effect
Methoxyacetic acid [2,3-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] 100
Methoxyacetic acid [3-fluoro-N-(5-methyl 2-oxoperhydro-3-furyl)-anilide] 100
Methoxyacetic acid [3-chloro-N-(5-methyl 2-oxoperhydro-3-furyl)-anilide] 100
Acetoxyacetic acid [2,6-dimethyl-N-(5- methyl-2-oxoperhydro-3-furyl)-anilide] 74
Phenylthio-acetic acid[2,6-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] 98
Acetoxyacetic acid [2-methyl-N (2-oxoperhydro-3-furyl )-anilide] 74
Acetoxyacetic acid [2,6-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] 100
Methoxyacetic acid [2-methyl-N (2-oxoperhydro-3-furyl)-anilide] 100
Methoxyacetic acid [2-methoxy-N-(oxoperhydro-3-furyl)-anilide] 100
Methoxyacetic acid [3-chloro-2-methyl-N (2-oxoperhydro-3-furyl)-anilide] 100
Acetoxyacetic acid [3-chloro-N (2-oxoperhydro-3-furyl)-anilide] 98
Acetoxyacetic acid [3-cyano-N (2-oxoperhydro-34ury1)-anilide] 74
Methoxyacetic acid [3-cyano-N (2-oxoperhydro-3-furyl)-anilide] 100
Ethylthio-acetic acid[2,6-di methyl-N (2-oxoperhydro-3-furyl)-anilide] 100
Isopropylthio-acetic acid[2,6-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] 100 tert.-Butylthio-acetic acid[2,6-dimethyl
N-(2-oxoperhydro-3-furyl)-anilide] 95 Isopropylsulphonylacetic acid [2,6-dimethyl
N-(2-oxoperhydro-3-furyl)-anilide] 100
Claims (117)
1. An acetic acid anilide of the general formula I
in which
R, represents a hydrogen atom or a C1-C4-alkyl group, R2 represents an unsubstituted aromatic hydrocarbon group or an aromatic hydrocarbon group substituted by one or more substituents selected from C1-C4-alkyl groups, C1-C4-alkoxy groups, C,C4-alkylthio groups, halogen atoms, trifluoromethyl groups, nitro groups, C,-C,-alkoxycarbonyl groups and cyano groups, R3 represents a C1-C6-alkyl, halogeno-C,-C,-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C5-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl or halogeno-C1-C6-alkylcarbonyl group, or represents an unsubstituted phenyl or benzyl group or a phenyl or benzyl group substituted by one or more substituents selected from halogen atoms and C1-C4-alkyl, C1-C4-alkoxy, C,C4-alkylthio, trifluoromethyl, nitro and amino groups, or represents an amidino or dimethylthio-carbamoyl group, and
X represents an oxygen sulphur atom or a sulphinyl or sulphonyl group.
2. An acid addition salt of a compound as claimed in claim 1 in which R3 represents and amidino group.
3. A compound as claimed in claim 1, wherein
R, represents a hydrogen atom or a methyl or ethyl group, R2 represents a phenyi, methylphenyl, dimethylphenyl, methoxyphenyl, fluorophenyl, chlorophenyl, bromophenyl, dichlorophenyl, trifluoromethylphenyl, methylthiophenyl or cyanophenyl group, R3 represents a methyl, ethyl, propyl, isopropyl, tert.-butyl, allyl, propenyl, propynyl, methoxyethyl, benzyl, chlorobenzyl, methylbenzyl, methoxybenzyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl, acetyl or chloracetyl group, and
X represents an oxygen or sulphur atom or a sulphinyl or sulphonyi group.
4. Methoxyacetic acid [2 ,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
5. Acetoxyacetic acid [2,6-dimethyl-N-(2-oxope rhydro-3-furyl)-anilide].
6. Methyithio-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
7. Dimethyldithiocarbamic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilinocarbonylmethyl] ester
8. Methoxyacetic acid {3-chloro-N-(2-oxoperhydro-3-furyl)-anilide].
9. Methoxyacetic acid [2,6-dimethyl-N-( 5-methyi-2-oxoperhydro-3-furyl)-anilide]
10. Methoxyacetic acid [N-(2-oxoperhydro-3-furyl)-anilide].
11. Methoxyacetic acid [3-methyl-N-(2-oxoperhydro-3-furyl)-anilide].
12. Methoxyacetic acid [2,3-dimethyl-N-(2-oxoperhydro-3-furyl)-anilidej.
13. Methoxyacetic acid [3-fluoro-N-(5-methyl-2-oxoperhydro-3-furyl)-anilide].
14. Methoxyacetic acid [3-chloro-N-(5-methyl-2-oxoperhydro-3-furyl)-anilide].
1 5. Methoxyacetic acid [2-methyl-N-(2-oxoperhydro-3-furyl)-anilide].
1 6. Methoxyacetic acid [2-methoxy-N-(2-oxoperhydro-3-furyl)-a nilide].
17. Methoxyacetic acid [3-chloro-2-methyl-N-(2-oxoperhydro-34uryI)-anilide].
18. methoxyacetic acid [3-cyano-N-(2-oxoperhydro-3-furyl)-a nilide].
19. Acetoxyacetic acid [3-methyl-N-(2-oxoperhyd ro3-fu ryl)-a ni lide].
20. Acetoxyacetic acid [N-(2-oxoperhydro-3-furyl)-anilide].
21. Acetoxyacetic acid [3-bromo-N-(2-oxoperhydro-3-furyl)-anilide].
22. Acetoxyacetic acid [2,3-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
23. Acetoxyacetic acid [3-fl uoro-N-(2-oxoperhydro-3-furyl)-anilide].
24. Acetoxyacetic acid [2,6-dimethyl-N-(5-methyl-2-oxoperhydro-3-furyl)-anilide].
25. Acetoxyacetic acid [2-methyl-N-(2-oxoperhyd ro-3-furyl)-a nilide].
26. Acetoxyacetic acid [3-chloro-N-(2-oxoperhydro-3-furyl)-anilide].
27 Acetoxyacetic acid [3-cyano-N-(2-oxoperhydro-3-furyl)-anilide].
28. Phenylthio-acetic acid[2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
29. Ethylthio-acetic a cid[2,6-di methyl-N-(2-oxoperhydro-3-furyl)-a nilide].
30. Isopropylthio-acetic acid[2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
31. tert.-Butylthio-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
32. S-[3-Chloro-N-(2-oxoperhydro-3-furyl)-anilinocarbonylmethyl]-thiuronium chloride.
33. Dimethyldithiocarbamic acid [3-chloro-N-(2-oxoperhydro-3-furyl)-anilinocarbonylmethylj ester.
34. Dimethylthiocarbamic acid [3-fluoro-N-(2-oxoperhydro-3-furyl)-anilinocarbonylmethyl] ester.
35. (3-Methylphenylthio)-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
36. (Benzylthio)-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-a nilide].
37. (2-Aminophenylthio)-acetic acid [2,6-di methyl-N-(2-oxoperhyd ro-3-furyl)-anilide] .
38. Ch loracetoxyacetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-a nilide].
39. Phenoxyacetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
40. Chloracetoxyacetic acid [N-(2-oxoperhydro-3-furyl)-anilide].
41. Chloracetoxyacetic acid [3-methyl-N-(2-oxoperhydro-3-furyl)-anilide].
42. Chloracetoxyacetic acid [3-bromo-N-(2-oxoperhydro-3-furyl)-anilide].
43. Phenoxyacetic acid [3-bromo-N-(2-oxoperhydro-3-furyl)-anilide].
44. Phenoxyacetic acid [N-(2-oxoperhydro-3-furyl)-anilide].
45. Phenoxyacetic acid [2,3-dimethyl-N-(2-oxoperhydro-3-fu ryl)-a nilide].
46. Phenoxyacetic acid [3-methyl-N-(2-oxoperhydro-3-furyl)-anilide].
47. Phenoxyacetic acid [2-methyl-N-(2-oxoperhydro-3-furyl)-anilide].
48. Phenoxyacetic acid [3-ch loro-N-(2-oxoperhydro-3-fu ryl)-a nilide] .
49. Chloracetoxyacetic acid [3-chloro-N-(2-oxoperhydro-3-furyl)-a nilide].
50. Phenoxyacetic acid [2,6-dimethyl-N-(5-methyl-2-oxoperhydro-3-furyl)-anilide].
51. Ch loracetoxyacetic acid [2,6-di methyl-N-( 5-methyl-2-oxoperhydro-3-furyl)-an ilide].
52. S-[2,6-Di methyl-N-(2-oxoperhydro-3-furyl)-a nilinoca rbonylmethyl]-thiuron ium chloride.
53. Isopropylsulphonyl-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
54. Ethoxyacetic acid [2,6-di methyl-N-(2-oxoperhydro-3-furyl)-a nilide].
55. Ethoxya cetic acid [2,6-dimethyl-N-(5-methyl-2-oxoperhydro-3-furyl)-anilide].
56. Ethoxyacetic acid [3-chloro-N-(2-oxoperhydro-3-fu ryl)-anilide] .
57. Ethoxyacetic acid [N-(2-oxoperhydro-3-furyl)-anilide].
58. Ethoxyacetic acid [3-bromo-N-(2-oxoperhydro-3-fu ryl)-anilide] .
59. Ethoxyacetic acid [3-methyl-N-(2-oxoperhydro-3-furyl)-anilide].
60. Ethoxyacetic acid [5-ch loro-2-methyl-N-( 2-oxoperhydro-3-furyl)-a nilide].
61. Ethoxyacetic acid [2-chloro-N-(2-oxoperhydro-3-furyl)-anilide].
62. Me thoxyacetic acid [2,6-dimethyl-N-( 5-butyl-2-oxoperhydro-3-furyl)-anilide].
63. Methoxyacetic acid [4-chloro-N-(2-oxoperhydro-3-furyl)-anilide].
64. A process for the manufacture of a compound of the general formula I given in claim 1, in which R1, R2, R3 and X have the meanings given in claim 1, wherein a compound of the general formula
II
in which Rt and R2 have the meanings given in claim 1, is reacted in an organic solvent with an acid halide of the general formula III HaIO-CH2-X-Fl2 (III) in which R3 and X have the meanings given in claim 1 and Hal represents a halogen atom.
65. A process as claimed in claim 64, wherein Hal represents a chlorine atom.
66. A process as claimed in claim 64 or 65, wherein the reaction is carried out in the presence of an acid acceptor.
67. A process as claimed in any one of claims 64 to 66, wherein a resulting compound of the general formula I, in which X represents a sulphur atom, is reacted in a solvent with an oxidizing agent to form a corresponding compound of the general formula I in which X represents a sulphinyl or sulphonyl group.
68. A process as claimed in any one of claims 64 to 67, wherein a resulting compound of the general formula I, in which R3 represents an amidino group, is converted into an acid addition salt thereof.
69. A process as claimed in claim 64, conducted substantially as described herein.
70. A process for the manufacture of a compound of the general formula I given in claim 1, in which Rr, R2 and R3 have the meanings given claim 1 and X represents a sulphur atom, wherein a compound of the general formula V
in which R1 and R2 have the meanings given in claim 1 and Hal represents a halogen atom, is reacted in an inert organic solvent under nitrogen with a compound of the general formula (-)
B S-Fl3, in which R3 has the meaning given in claim 1 and B represents an alkali metal atom, or, when R3 represents an amidino group, with thiourea of the formula
71 A process as claimed in claim 70, wherein Hal represents a chlorine atom.
72. A process as claimed in claim 70 or 71, wherein B represents a sodium atom.
73. A process as claimed in any one of claims 70 to 72, wherein the resulting compound of the general formula I is reacted in a solvent with an oxidizing agent to form a corresponding compound of the general formula I in which X represents a sulphinyl or sulphonyl group.
74. A process as claimed in any one of claims 70 to 73, wherein a resulting compound of the general formula I, in which R3 represents an amidino group, is converted into an acid addition salt thereof.
75. A process as claimed in any one of claims 70 to 74, wherein the compound of the general formula V has been prepared by reacting in an organic solvent a compound of the general formula II
in which Rt and R2 have the meanings given in claim 1, with an acid halide of the general formula IV Hal'-COH2-Hal (IV), in which Hal and Hal' each represents a halogen atom.
76. A process as claimed in claim 75, wherein Hal and Hal' each represents a chlorine atom.
77. A process as claimed in claim 75 or 76, wherein the reaction with the compound of the general formula IV is carried out in the presence of an acid acceptor.
78. A process as claimed in claim 70, conducted substantially as described herein.
79. A process for the manufacture of a compound of the general formula I given in claim 1, in which R1, R2 and R3 have the meanings given in claim 1 and X represents a sulphinyl or sulphonyl group, wherein a compound of the general formula la
in which Fl1, R2 and R3 have the meanings given in claim 1, is reacted in a solvent with an oxidizing agent.
80. A process as claimed in claim 79, wherein a resulting compound of the general formula I, in which R3 represents an amidino group, is converted into an acid addition salt thereof.
81. A process as claimed in claim 79, conducted substantially as described herein.
82. A process for the manufacture of a compound as claimed in claim 1, conducted substantially as described in any one of Examples 1 to 5 herein.
83. A fungicidal preparation which comprises a compound of the general formula I given in claim 1, in which Fl1, R2, R3 and X have the meanings given in claim 1, in admixture of conjunction with a suitable carrier.
84. A fungicidal preparation which comprises a salt as claimed in claim 2, in admixture or conjunction with a suitable carrier.
85. A fungicidal preparation which comprises a compound as claimed in claim 3, in admixture or conjunction with a suitable carrier.
86. A fungicidal preparation which comprises the compound claimed in any one of claims 4 to 63, in admixture or conjunction with a suitable carrier.
87. A preparation as claimed in any one of claims 83 to 86, which is in the form of a powder, a strewable preparation, granules, a solution, an emuision or a suspension.
88. A preparation as claimed in any one of claims 83 to 87, containing a single compound selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group.
89. A preparation as claimed in any one of claims 83 to 87, containing two or more compounds selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group.
90 A preparation as claimed in any one of claims 83 to 89, which also contains one or more active substances selected from fungicides and pesticides other than compounds as claimed in claims 1 and 2.
91. A preparation as claimed in any one of claims 83 to 90, wherein the total amount present of active substance or substances is approximately 1 to 80% by weight.
92. A preparation as claimed in claim 91, wherein the total amount present of active substance or substances is 20 to 50% by weight.
93. A preparation as claimed in any one of claims 83 to 92, containing a single surface-active agent in an amount of up to 20% by weight.
94. A preparation as claimed in any one of claims 83 to 92, containing two or more surface-active agents in a total amount of up to 20% by weight.
95. A preparation as claimed in any one of claims 83 to 94, which also contains a dyestuff.
96. Any one of the fungicidal preparations as claimed in claim 83 and substantially as described in
Examples 6 to 12 herein.
97. A method of protecting a living plant against phytopathogenic fungi, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound of the general formula I given in claim 1, in which Fl1, R2, R3 and X have the meanings given in claim 1.
98. A method of protecting a living plant against phytopathogenic fungi, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a salt as claimed in claim 2.
99. A method as claimed in claim 97, wherein the treatment is carried out with a compound as claimed in claim 3.
100. A method as claimed in claim 97 or 98, wherein the treatment is carried out with the compound claimed in any one of claims 4 to 63.
101. A method as claimed in claim 97 or 98, wherein the treatment is carried out with a fungicidal preparation as claimed in any one of claims 83 to 94 and 96.
102. A method as claimed in claim 97, conducted substantially as described in any one of
Examples 7 to 10 and 12 herein.
1 03. A method of protecting a crop area against phytopathogenic fungi, wherein the crop area is treated with a compound of the general formula I given in claim 1, in which Fl1, R2, R3 and X have the meanings given in claim 1.
1 04. A method of protecting a crop area against phytopathogenic fungi, wherein the crop area is treated with a salt as claimed in claim 2.
1 05. A method as claimed in claim 103, wherein the crop area is treated with a compound as claimed in claim 3.
106. A method as claimed in claim 103 or 104, wherein the crop area is treated with the compound claimed in any one of claims4 to 63.
1 07. A method as claimed in claim 103 or 104, wherein the crop area is treated with a fungicidal preparation as claimed in any one of claims 83 to 94 and 96.
108. A method as claimed in claim 103, conducted substantially as described in Example 6 herein.
109. A method of dressing seeds, wherein the seeds are treated with a compound of the general formula I given in claim 1, in which R1, R2, R3 and X have the meanings given in claim 1.
110. A method of dressing seeds, wherein the seeds are treated with a salt as claimed in claim 2.
111. A method as claimed in claim 109, wherein the seeds are treated with a compound as claimed in claim 3.
112. A method as claimed in claim 109 or 110, wherein the seeds are treated with the compound claimed in any one of claims 4 to 63.
113. A method as claimed in claim 109 or 110, wherein the seeds are treated with a fungicidal preparation as claimed in any one of claims 83 to 96.
11 4. A method as claimed in claim 109, conducted substantially as described in Example 11 herein.
115. A pack which comprises a compound of the general formula I given in claim 1, in which Rs, R2, R3 and X have the meanings given in claim 1, together with instructions for its use for controlling phytopathogenic fungi.
11 6. A pack which comprises a salt as claimed in claim 2, together with instructions for its use for controlling phytopathogenic fungi.
117. A pack as claimed in claim 11 5, wherein the compound of the general formula I is a compound as claimed in claim 3.
11 8. A pack which comprises the compound claimed in any one of claims 4 to 163, together with instructions for its use for controlling phytopathogenic fungi.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782841824 DE2841824A1 (en) | 1978-09-22 | 1978-09-22 | ACETIC ACID ANILIDE, METHOD FOR PRODUCING THESE COMPOUNDS, AND THIS FUNGICIDAL CONTAINER |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2033379A true GB2033379A (en) | 1980-05-21 |
| GB2033379B GB2033379B (en) | 1982-12-22 |
Family
ID=6050476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7932156A Expired GB2033379B (en) | 1978-09-22 | 1979-09-17 | Fungicidally active acetic acid anilides and their manufacture and use |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5545682A (en) |
| AT (1) | AT365890B (en) |
| AU (1) | AU5107679A (en) |
| BE (1) | BE878924A (en) |
| BG (1) | BG30624A3 (en) |
| BR (1) | BR7905455A (en) |
| CS (1) | CS219905B2 (en) |
| DD (1) | DD145989A5 (en) |
| DE (1) | DE2841824A1 (en) |
| DK (1) | DK346179A (en) |
| ES (1) | ES483787A1 (en) |
| FR (1) | FR2436782A1 (en) |
| GB (1) | GB2033379B (en) |
| HU (1) | HU182612B (en) |
| IL (1) | IL58273A0 (en) |
| IT (1) | IT1165288B (en) |
| LU (1) | LU81703A1 (en) |
| NL (1) | NL7905267A (en) |
| PL (1) | PL119374B1 (en) |
| RO (1) | RO78587A (en) |
| SU (1) | SU988191A3 (en) |
| YU (1) | YU204879A (en) |
| ZA (1) | ZA795021B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2845454A1 (en) * | 1977-11-01 | 1979-05-10 | Chevron Res | 3- (N-ACYL-N-ARYLAMINO) - GAMMA -BUTYROLACTONE AND - GAMMA -BUTYROTHIOLACTONE AND FUNGICIDE AGENTS |
| JPH02124375U (en) * | 1989-03-27 | 1990-10-12 |
-
1978
- 1978-09-22 DE DE19782841824 patent/DE2841824A1/en not_active Withdrawn
-
1979
- 1979-07-05 NL NL7905267A patent/NL7905267A/en not_active Application Discontinuation
- 1979-08-17 DK DK346179A patent/DK346179A/en not_active Application Discontinuation
- 1979-08-20 CS CS795676A patent/CS219905B2/en unknown
- 1979-08-21 YU YU02048/79A patent/YU204879A/en unknown
- 1979-08-21 IT IT25202/79A patent/IT1165288B/en active
- 1979-08-24 BR BR7905455A patent/BR7905455A/en unknown
- 1979-08-31 ES ES483787A patent/ES483787A1/en not_active Expired
- 1979-09-12 DD DD79215492A patent/DD145989A5/en unknown
- 1979-09-17 GB GB7932156A patent/GB2033379B/en not_active Expired
- 1979-09-19 IL IL58273A patent/IL58273A0/en unknown
- 1979-09-20 LU LU81703A patent/LU81703A1/en unknown
- 1979-09-20 PL PL1979218428A patent/PL119374B1/en unknown
- 1979-09-21 AT AT0622679A patent/AT365890B/en not_active IP Right Cessation
- 1979-09-21 ZA ZA00795121A patent/ZA795021B/en unknown
- 1979-09-21 BG BG044915A patent/BG30624A3/en unknown
- 1979-09-21 RO RO7998732A patent/RO78587A/en unknown
- 1979-09-21 AU AU51076/79A patent/AU5107679A/en not_active Abandoned
- 1979-09-21 JP JP12092979A patent/JPS5545682A/en active Pending
- 1979-09-21 SU SU792817359A patent/SU988191A3/en active
- 1979-09-21 BE BE0/197256A patent/BE878924A/en not_active IP Right Cessation
- 1979-09-22 HU HU79SCHE692A patent/HU182612B/en unknown
- 1979-09-24 FR FR7923680A patent/FR2436782A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| RO78587A (en) | 1982-03-24 |
| JPS5545682A (en) | 1980-03-31 |
| BG30624A3 (en) | 1981-07-15 |
| DD145989A5 (en) | 1981-01-21 |
| YU204879A (en) | 1983-02-28 |
| IT7925202A0 (en) | 1979-08-21 |
| BE878924A (en) | 1980-03-21 |
| PL218428A1 (en) | 1980-07-14 |
| IL58273A0 (en) | 1979-12-30 |
| AT365890B (en) | 1982-02-25 |
| ZA795021B (en) | 1980-09-24 |
| NL7905267A (en) | 1980-03-25 |
| HU182612B (en) | 1984-02-28 |
| CS219905B2 (en) | 1983-03-25 |
| BR7905455A (en) | 1980-05-20 |
| IT1165288B (en) | 1987-04-22 |
| DK346179A (en) | 1980-03-23 |
| SU988191A3 (en) | 1983-01-07 |
| AU5107679A (en) | 1980-04-17 |
| ATA622679A (en) | 1981-07-15 |
| ES483787A1 (en) | 1980-05-16 |
| FR2436782B1 (en) | 1983-07-22 |
| PL119374B1 (en) | 1981-12-31 |
| DE2841824A1 (en) | 1980-04-03 |
| GB2033379B (en) | 1982-12-22 |
| LU81703A1 (en) | 1980-01-24 |
| FR2436782A1 (en) | 1980-04-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |