CH637393A5 - Furancarboxanilides, fungicides containing these compounds, and processes for their preparation - Google Patents

Furancarboxanilides, fungicides containing these compounds, and processes for their preparation Download PDF

Info

Publication number: CH637393A5
Authority: CH; Switzerland
Prior art keywords: furan; carboxylic acid; anilide; furyl; compound according
Prior art date: 1977-05-27

Application number

CH561278A

Other languages

German (de)

English (en)

Inventor

Ulrich Buehmann

Reinhold Puttner

Ernst-Albrecht Pieroh

Dietrich Baumert

Original Assignee

Schering Ag

Priority date (The priority date 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 date listed.)

1977-05-27

Filing date

1978-05-23

Publication date

1983-07-29

1977-05-27 Priority claimed from DE19772724785 external-priority patent/DE2724785A1/de

1978-05-23 Application filed by Schering Ag filed Critical Schering Ag

1983-07-29 Publication of CH637393A5 publication Critical patent/CH637393A5/de

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 94
XHVDWCKBZSFUDE-UHFFFAOYSA-N n-phenylfuran-2-carboxamide Chemical class C=1C=COC=1C(=O)NC1=CC=CC=C1 XHVDWCKBZSFUDE-UHFFFAOYSA-N 0.000 title claims abstract description 8
239000000417 fungicide Substances 0.000 title claims abstract description 7
238000002360 preparation method Methods 0.000 title claims description 13
238000000034 method Methods 0.000 title claims description 6
241000233866 Fungi Species 0.000 claims abstract description 19
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
230000003032 phytopathogenic effect Effects 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
-1 2-oxoperhydro-3-furyl Chemical group 0.000 claims description 52
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 46
150000003931 anilides Chemical class 0.000 claims description 35
239000002689 soil Substances 0.000 claims description 30
239000004480 active ingredient Substances 0.000 claims description 27
239000003795 chemical substances by application Substances 0.000 claims description 17
230000000855 fungicidal effect Effects 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 15
239000013543 active substance Substances 0.000 claims description 9
125000002541 furyl group Chemical group 0.000 claims description 9
239000000243 solution Substances 0.000 claims description 8
239000000969 carrier Substances 0.000 claims description 7
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 claims description 6
YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 claims description 5
NYTSGVNQPPRLIV-UHFFFAOYSA-N C1COC(=O)C1N(C2=CC=CC=C2)C(=O)C3=CC=CO3 Chemical compound C1COC(=O)C1N(C2=CC=CC=C2)C(=O)C3=CC=CO3 NYTSGVNQPPRLIV-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000007788 liquid Substances 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
QGSPMMHFFLTIQF-UHFFFAOYSA-N C1COC(=O)C1N(C2=CC(=CC=C2)F)C(=O)C3=CC=CO3 Chemical compound C1COC(=O)C1N(C2=CC(=CC=C2)F)C(=O)C3=CC=CO3 QGSPMMHFFLTIQF-UHFFFAOYSA-N 0.000 claims description 4
MZUCEBNIWHZUHG-UHFFFAOYSA-N CC1=CC(=CC=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CC1=CC(=CC=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 MZUCEBNIWHZUHG-UHFFFAOYSA-N 0.000 claims description 4
KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 claims description 4
CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 claims description 3
FHXHGFHMANKXNY-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CC1=C(C(=CC=C1)C)N(C2CCOC2=O)C(=O)C3=CC=CO3 FHXHGFHMANKXNY-UHFFFAOYSA-N 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
230000009885 systemic effect Effects 0.000 claims description 3
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
PHQWGNQBSLVJNQ-UHFFFAOYSA-N C(C)C1=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C(=CC=C1)CC Chemical compound C(C)C1=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C(=CC=C1)CC PHQWGNQBSLVJNQ-UHFFFAOYSA-N 0.000 claims description 2
QXUPDOLNEYQTPA-UHFFFAOYSA-N C1COC(=O)C1N(C2=C(C(=CC=C2)Cl)Cl)C(=O)C3=CC=CO3 Chemical compound C1COC(=O)C1N(C2=C(C(=CC=C2)Cl)Cl)C(=O)C3=CC=CO3 QXUPDOLNEYQTPA-UHFFFAOYSA-N 0.000 claims description 2
LCYRDHMYLHHJCM-UHFFFAOYSA-N C1COC(=O)C1N(C2=CC(=C(C=C2)Cl)Cl)C(=O)C3=CC=CO3 Chemical compound C1COC(=O)C1N(C2=CC(=C(C=C2)Cl)Cl)C(=O)C3=CC=CO3 LCYRDHMYLHHJCM-UHFFFAOYSA-N 0.000 claims description 2
MGSVEWGFJQFTPO-UHFFFAOYSA-N C1COC(=O)C1N(C2=CC(=CC(=C2)Cl)Cl)C(=O)C3=CC=CO3 Chemical compound C1COC(=O)C1N(C2=CC(=CC(=C2)Cl)Cl)C(=O)C3=CC=CO3 MGSVEWGFJQFTPO-UHFFFAOYSA-N 0.000 claims description 2
VGKDYVJCHMIDMD-UHFFFAOYSA-N C1COC(=O)C1N(C2=CC=C(C=C2)Br)C(=O)C3=CC=CO3 Chemical compound C1COC(=O)C1N(C2=CC=C(C=C2)Br)C(=O)C3=CC=CO3 VGKDYVJCHMIDMD-UHFFFAOYSA-N 0.000 claims description 2
WESDWTKOPHYCSY-UHFFFAOYSA-N C1COC(=O)C1N(C2=CC=C(C=C2)C3=CC=CC=C3)C(=O)C4=CC=CO4 Chemical compound C1COC(=O)C1N(C2=CC=C(C=C2)C3=CC=CC=C3)C(=O)C4=CC=CO4 WESDWTKOPHYCSY-UHFFFAOYSA-N 0.000 claims description 2
ZEQALRJGIPMXLG-UHFFFAOYSA-N C1COC(=O)C1N(C2=CC=C(C=C2)F)C(=O)C3=CC=CO3 Chemical compound C1COC(=O)C1N(C2=CC=C(C=C2)F)C(=O)C3=CC=CO3 ZEQALRJGIPMXLG-UHFFFAOYSA-N 0.000 claims description 2
WZCWBHQTDNYLKG-UHFFFAOYSA-N C1COC(=O)C1N(C2=CC=CC=C2Br)C(=O)C3=CC=CO3 Chemical compound C1COC(=O)C1N(C2=CC=CC=C2Br)C(=O)C3=CC=CO3 WZCWBHQTDNYLKG-UHFFFAOYSA-N 0.000 claims description 2
BOIDPHOCNIFQLL-UHFFFAOYSA-N CC(=O)C1=CC(=CC=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CC(=O)C1=CC(=CC=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 BOIDPHOCNIFQLL-UHFFFAOYSA-N 0.000 claims description 2
XIMJCEGNZQXSCW-UHFFFAOYSA-N CC1=C(C=CC(=C1)OC)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CC1=C(C=CC(=C1)OC)N(C2CCOC2=O)C(=O)C3=CC=CO3 XIMJCEGNZQXSCW-UHFFFAOYSA-N 0.000 claims description 2
GIGXOCGFNIZLFC-UHFFFAOYSA-N CC1=C(N(C(=O)C=2OC=CC2)C2C(OC(C2)C)=O)C(=CC=C1)C Chemical compound CC1=C(N(C(=O)C=2OC=CC2)C2C(OC(C2)C)=O)C(=CC=C1)C GIGXOCGFNIZLFC-UHFFFAOYSA-N 0.000 claims description 2
PVMSJHCYBSQQFP-UHFFFAOYSA-N CC1=CC=C(C=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CC1=CC=C(C=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 PVMSJHCYBSQQFP-UHFFFAOYSA-N 0.000 claims description 2
YTEBNLGXSDFSIM-UHFFFAOYSA-N CCC1=CC(=CC=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CCC1=CC(=CC=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 YTEBNLGXSDFSIM-UHFFFAOYSA-N 0.000 claims description 2
CXZGSFDAVOWBEZ-UHFFFAOYSA-N CCC1=CC=C(C=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CCC1=CC=C(C=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 CXZGSFDAVOWBEZ-UHFFFAOYSA-N 0.000 claims description 2
HFUNDADSLKPHBV-UHFFFAOYSA-N CCC1=CC=CC=C1N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CCC1=CC=CC=C1N(C2CCOC2=O)C(=O)C3=CC=CO3 HFUNDADSLKPHBV-UHFFFAOYSA-N 0.000 claims description 2
IFLKCJSUBNZSME-UHFFFAOYSA-N CCOC1=CC=C(C=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CCOC1=CC=C(C=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 IFLKCJSUBNZSME-UHFFFAOYSA-N 0.000 claims description 2
HQAUGNMSMFATTP-UHFFFAOYSA-N CCOC1=CC=CC=C1N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CCOC1=CC=CC=C1N(C2CCOC2=O)C(=O)C3=CC=CO3 HQAUGNMSMFATTP-UHFFFAOYSA-N 0.000 claims description 2
IUIUSLACDOAFOY-UHFFFAOYSA-N COC(=O)C1=CC=CC=C1N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound COC(=O)C1=CC=CC=C1N(C2CCOC2=O)C(=O)C3=CC=CO3 IUIUSLACDOAFOY-UHFFFAOYSA-N 0.000 claims description 2
MCEJWRIFTKAINZ-UHFFFAOYSA-N COC1=C(C=C(C=C1)Cl)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound COC1=C(C=C(C=C1)Cl)N(C2CCOC2=O)C(=O)C3=CC=CO3 MCEJWRIFTKAINZ-UHFFFAOYSA-N 0.000 claims description 2
FFQWDDJZQVFDDS-UHFFFAOYSA-N COC1=CC=CC(=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound COC1=CC=CC(=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 FFQWDDJZQVFDDS-UHFFFAOYSA-N 0.000 claims description 2
XGXDRDHNNRLRDA-UHFFFAOYSA-N COC1=CC=CC=C1N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound COC1=CC=CC=C1N(C2CCOC2=O)C(=O)C3=CC=CO3 XGXDRDHNNRLRDA-UHFFFAOYSA-N 0.000 claims description 2
ZOFHQUZAGVPSOE-UHFFFAOYSA-N CSC1=CC=CC(=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CSC1=CC=CC(=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 ZOFHQUZAGVPSOE-UHFFFAOYSA-N 0.000 claims description 2
PRMZLCXWDZRBAC-UHFFFAOYSA-N ClC1=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C=CC=C1 Chemical compound ClC1=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C=CC=C1 PRMZLCXWDZRBAC-UHFFFAOYSA-N 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004799 bromophenyl group Chemical group 0.000 claims description 2
125000000068 chlorophenyl group Chemical group 0.000 claims description 2
125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000000839 emulsion Substances 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000001207 fluorophenyl group Chemical group 0.000 claims description 2
239000008187 granular material Substances 0.000 claims description 2
239000004009 herbicide Substances 0.000 claims description 2
238000003898 horticulture Methods 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000005645 nematicide Substances 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
244000052769 pathogen Species 0.000 claims description 2
239000000575 pesticide Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
230000000885 phytotoxic effect Effects 0.000 claims description 2
239000000843 powder Substances 0.000 claims description 2
230000003449 preventive effect Effects 0.000 claims description 2
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 claims description 2
229960002447 thiram Drugs 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
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LCSORLPRDRIPEW-UHFFFAOYSA-N COC1=CC=C(C=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound COC1=CC=C(C=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3 LCSORLPRDRIPEW-UHFFFAOYSA-N 0.000 claims 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 abstract 1
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125000001424 substituent group Chemical group 0.000 abstract 1
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240000002395 Euphorbia pulcherrima Species 0.000 description 2
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JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
241001635622 Pythium splendens Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000001035 drying 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000004382 potting Methods 0.000 description 2
230000000069 prophylactic effect Effects 0.000 description 2
238000005507 spraying Methods 0.000 description 2
QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
235000001674 Agaricus brunnescens Nutrition 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
ZFEFIWDMPBBJKY-UHFFFAOYSA-N C1COC(=O)C1N(C2=CC=C(C=C2)Cl)C(=O)C3=CC=CO3 Chemical compound C1COC(=O)C1N(C2=CC=C(C=C2)Cl)C(=O)C3=CC=CO3 ZFEFIWDMPBBJKY-UHFFFAOYSA-N 0.000 description 1
DLWCOTXVUAZPBL-UHFFFAOYSA-N CC(C=CC=C1)=C1N(C(CCO1)C1=O)C(C1=CC=CO1)=O Chemical compound CC(C=CC=C1)=C1N(C(CCO1)C1=O)C(C1=CC=CO1)=O DLWCOTXVUAZPBL-UHFFFAOYSA-N 0.000 description 1
MEOANHVGINKZPP-UHFFFAOYSA-N CC1=C(C=C(C=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3)C Chemical compound CC1=C(C=C(C=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3)C MEOANHVGINKZPP-UHFFFAOYSA-N 0.000 description 1
UQVIRKWNGBCWRR-UHFFFAOYSA-N CC1=CC(=C(C(=C1)C)N(C2CCOC2=O)C(=O)C3=CC=CO3)C Chemical compound CC1=CC(=C(C(=C1)C)N(C2CCOC2=O)C(=O)C3=CC=CO3)C UQVIRKWNGBCWRR-UHFFFAOYSA-N 0.000 description 1
VVTWHQKYPGOEPV-UHFFFAOYSA-N CC1=CC(=C(C=C1)C)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CC1=CC(=C(C=C1)C)N(C2CCOC2=O)C(=O)C3=CC=CO3 VVTWHQKYPGOEPV-UHFFFAOYSA-N 0.000 description 1
QVCGJPMQYWEVSN-UHFFFAOYSA-N CC1=CC(=C(C=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3)C Chemical compound CC1=CC(=C(C=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3)C QVCGJPMQYWEVSN-UHFFFAOYSA-N 0.000 description 1
SZQFMJIBMKGGGR-UHFFFAOYSA-N CC1=CC(=CC(=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3)C Chemical compound CC1=CC(=CC(=C1)N(C2CCOC2=O)C(=O)C3=CC=CO3)C SZQFMJIBMKGGGR-UHFFFAOYSA-N 0.000 description 1
CRJFLTUTWKKKAV-UHFFFAOYSA-N CC1CC(C(=O)O1)N(C2=CC(=CC=C2)Cl)C(=O)C3=CC=CO3 Chemical compound CC1CC(C(=O)O1)N(C2=CC(=CC=C2)Cl)C(=O)C3=CC=CO3 CRJFLTUTWKKKAV-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
240000005322 Gloxinia perennis Species 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000208181 Pelargonium Species 0.000 description 1
241000580814 Pelargonium peltatum Species 0.000 description 1
241000233614 Phytophthora 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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241001622887 Pythium sylvaticum Species 0.000 description 1
241000232168 Sinningia Species 0.000 description 1
244000093304 Sinningia speciosa Species 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
240000006365 Vitis vinifera Species 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 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
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
REQPQFUJGGOFQL-UHFFFAOYSA-N dimethylcarbamothioyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SC(=S)N(C)C REQPQFUJGGOFQL-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
229910052571 earthenware Inorganic materials 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000003359 percent control normalization Methods 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
239000000454 talc Substances 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
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- 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
- A01N43/14—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 six-membered rings
- A01N43/16—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 six-membered rings with oxygen as the ring hetero atom
- 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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Furan Compounds (AREA)

CH561278A 1977-05-27 1978-05-23 Furancarboxanilides, fungicides containing these compounds, and processes for their preparation CH637393A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772724785 DE2724785A1 (de)	1977-05-27	1977-05-27	Furancarbonsaeureanilide, fungizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
CH637393A5 true CH637393A5 (en)	1983-07-29

Family

ID=6010434

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH561278A CH637393A5 (en)	1977-05-27	1978-05-23	Furancarboxanilides, fungicides containing these compounds, and processes for their preparation

Country Status (27)

Country	Link
AR (1)	AR224234A1 (cs)
BG (1)	BG28687A3 (cs)
BR (1)	BR7803217A (cs)
CA (1)	CA1156665A (cs)
CH (1)	CH637393A5 (cs)
CS (1)	CS194200B2 (cs)
DD (1)	DD136092A5 (cs)
DK (1)	DK192278A (cs)
EG (1)	EG13300A (cs)
ES (1)	ES469811A1 (cs)
FI (1)	FI781211A7 (cs)
GR (1)	GR71669B (cs)
HU (1)	HU180985B (cs)
IE (1)	IE46922B1 (cs)
IL (1)	IL54720A (cs)
IT (1)	IT1096327B (cs)
MX (1)	MX5432E (cs)
NO (1)	NO149431C (cs)
NZ (1)	NZ187271A (cs)
PH (1)	PH15611A (cs)
PL (1)	PL110264B1 (cs)
PT (1)	PT68085A (cs)
RO (1)	RO75073A (cs)
SU (2)	SU727108A3 (cs)
TR (1)	TR20539A (cs)
YU (1)	YU97778A (cs)
ZA (1)	ZA783037B (cs)

1978
- 1978-04-19 FI FI781211A patent/FI781211A7/fi not_active Application Discontinuation
- 1978-04-25 YU YU00977/78A patent/YU97778A/xx unknown
- 1978-05-03 DK DK192278A patent/DK192278A/da not_active Application Discontinuation
- 1978-05-10 TR TR20539A patent/TR20539A/xx unknown
- 1978-05-11 MX MX787080U patent/MX5432E/es unknown
- 1978-05-12 ES ES469811A patent/ES469811A1/es not_active Expired
- 1978-05-15 CS CS783117A patent/CS194200B2/cs unknown
- 1978-05-15 NZ NZ187271A patent/NZ187271A/xx unknown
- 1978-05-15 PH PH21133A patent/PH15611A/en unknown
- 1978-05-16 IL IL54720A patent/IL54720A/xx unknown
- 1978-05-22 BR BR787803217A patent/BR7803217A/pt unknown
- 1978-05-23 CH CH561278A patent/CH637393A5/de not_active IP Right Cessation
- 1978-05-24 PL PL1978207070A patent/PL110264B1/pl unknown
- 1978-05-24 EG EG332/78A patent/EG13300A/xx active
- 1978-05-24 IE IE1028/78A patent/IE46922B1/en unknown
- 1978-05-24 PT PT68085A patent/PT68085A/pt unknown
- 1978-05-25 DD DD78205585A patent/DD136092A5/xx unknown
- 1978-05-25 RO RO7894165A patent/RO75073A/ro unknown
- 1978-05-25 IT IT23778/78A patent/IT1096327B/it active
- 1978-05-26 CA CA000304214A patent/CA1156665A/en not_active Expired
- 1978-05-26 SU SU782621054A patent/SU727108A3/ru active
- 1978-05-26 SU SU782617650A patent/SU725560A3/ru active
- 1978-05-26 BG BG039861A patent/BG28687A3/xx unknown
- 1978-05-26 GR GR56345A patent/GR71669B/el unknown
- 1978-05-26 NO NO781837A patent/NO149431C/no unknown
- 1978-05-26 ZA ZA00783037A patent/ZA783037B/xx unknown
- 1978-05-26 HU HU78SCHE645A patent/HU180985B/hu unknown
- 1978-05-27 AR AR272307A patent/AR224234A1/es active

Also Published As

Publication number	Publication date
SU727108A3 (ru)	1980-04-05
CA1156665A (en)	1983-11-08
FI781211A7 (fi)	1978-11-28
IE781028L (en)	1978-11-27
DK192278A (da)	1978-11-28
ES469811A1 (es)	1978-12-16
HU180985B (en)	1983-05-30
NO781837L (no)	1978-11-28
NO149431C (no)	1984-04-25
PT68085A (de)	1978-06-01
GR71669B (cs)	1983-06-20
SU725560A1 (ru)	1980-03-30
IT7823778A0 (it)	1978-05-25
NO149431B (no)	1984-01-09
IL54720A0 (en)	1978-07-31
NZ187271A (en)	1980-10-08
CS194200B2 (en)	1979-11-30
ZA783037B (en)	1979-06-27
EG13300A (en)	1981-12-31
IL54720A (en)	1983-07-31
YU97778A (en)	1983-01-21
PL207070A1 (pl)	1979-02-26
PH15611A (en)	1983-02-28
SU725560A3 (en)	1980-03-30
IT1096327B (it)	1985-08-26
PL110264B1 (en)	1980-07-31
TR20539A (tr)	1981-10-21
DD136092A5 (de)	1979-06-20
RO75073A (ro)	1980-10-30
BR7803217A (pt)	1979-01-16
AR224234A1 (es)	1981-11-13
MX5432E (es)	1983-08-05
BG28687A3 (bg)	1980-06-16
IE46922B1 (en)	1983-11-02

Legal Events

Date	Code	Title	Description
1985-01-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
KR890000482B1 (ko)	1989-03-18	N-페닐카르바메이트 함유 살균성 조성물
CH621921A5 (cs)	1981-03-13
CH632130A5 (en)	1982-09-30	Compositions on the basis of oxime ethers, oxime esters or oxime carbamates which are suitable in agriculture for crop protection
DE2804299A1 (de)	1978-08-10	Fungizide mittel
DE69315774T2 (de)	1998-05-07	Kondensierte heterocyclische Derivate und sie enthaltende Fungizide, für Landwirtschaft und Gartenbau
DE69222568T2 (de)	1998-02-12	Benzimidazolderivate, Verfahren zu ihrer Herstellung, diese als aktiven Bestandteil enthaltende Fungizide für Landwirtschaft und Gartenbau und Zwischenprodukte dafür
DE2813335C2 (de)	1987-04-09	N-acylierte N-Alkylaniline, Verfahren zu ihrer Herstellung sowie mikrobizide Mittel enthaltend diese als Wirkstoffe
DE2724786C2 (de)	1986-07-24	Cyclopropancarbonsäure-[N-(2-oxoperhydro-3-furyl)-anilide], Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende fungizide Mittel
DE2724785A1 (de)	1978-12-14	Furancarbonsaeureanilide, fungizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung
CH637393A5 (en)	1983-07-29	Furancarboxanilides, fungicides containing these compounds, and processes for their preparation
US4210440A (en)	1980-07-01	Urea derivatives, process for preparing the same and herbicidal composition containing the same
DE2902861A1 (de)	1979-08-02	Mikrobizide mittel
DE2919825C2 (cs)	1988-09-01
DE1810581C3 (de)	1977-12-29	N-Acyl-p-dialkylamino-phenylhydrazone, Verfahren zu ihrer Herstellung und deren Verwendung zur Bekämpfung von phytopathogene Pilzen
KR810001153B1 (ko)	1981-09-22	사이클로프로판 카복실산 아닐리드류의 제조방법
CH614102A5 (en)	1979-11-15	Pesticides
DE2841824A1 (de)	1980-04-03	Essigsaeureanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes fungizides mittel
DE2946910A1 (de)	1981-07-02	Fungizide sulfonyl-, bzw. sulfinylacetanilide
JPS613A (ja)	1986-01-06	植物病害防除剤
DE2933008A1 (de)	1981-04-09	2-sulfinyl-5-sulfonyl-1,3,4-thiadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide mittel
DE2917914A1 (de)	1980-11-13	N-(alkoxy- bzw. alkoxycarbonylalkyl)- n-alkoxyalkoxyacetyl-anilin-derivate
CH625784A5 (en)	1981-10-15	Microbicides
JPS61225179A (ja)	1986-10-06	アニリド誘導体およびそれを含有する除草剤
DE1810581B2 (de)	1977-05-05	N-acyl-p-dialkylamino-phenylhydrazone, verfahren zu ihrer herstellung und deren verwendung zur bekaempfung von phytopathogene pilzen
CH617567A5 (en)	1980-06-13	Pesticides.