CA1156665A - Fungicidally active furancarboxylic acid anilides - Google Patents

Fungicidally active furancarboxylic acid anilides

Info

Publication number: CA1156665A
Authority: CA; Canada
Prior art keywords: compound; furan; anilide; furyl; oxoperhydro
Prior art date: 1977-05-27
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.): Expired

Application number

CA000304214A

Other languages

English (en)

French (fr)

Inventor

Ulrich Buhmann

Reinhold Puttner

Ernst-Albrecht Pieroh

Dietrich Baumert

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Pharma AG

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

1978-05-26

Publication date

1983-11-08

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

1978-05-26 Application filed by Schering AG filed Critical Schering AG

1983-11-08 Application granted granted Critical

1983-11-08 Publication of CA1156665A publication Critical patent/CA1156665A/en

Status Expired legal-status Critical Current

Links

XHVDWCKBZSFUDE-UHFFFAOYSA-N n-phenylfuran-2-carboxamide Chemical class C=1C=COC=1C(=O)NC1=CC=CC=C1 XHVDWCKBZSFUDE-UHFFFAOYSA-N 0.000 title abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
125000001424 substituent group Chemical group 0.000 claims abstract description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 4
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 100
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 81
241000233866 Fungi Species 0.000 claims description 29
238000000034 method Methods 0.000 claims description 28
-1 dimethylphenyl Chemical group 0.000 claims description 24
230000003032 phytopathogenic effect Effects 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
150000003931 anilides Chemical class 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
WIGLFQRQCVYIKN-UHFFFAOYSA-N BrC=1C=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C=CC1 Chemical compound BrC=1C=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C=CC1 WIGLFQRQCVYIKN-UHFFFAOYSA-N 0.000 claims description 2
WRFSLDCXLWWGMJ-UHFFFAOYSA-N C(C)(C)C1=CC=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C=C1 Chemical compound C(C)(C)C1=CC=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C=C1 WRFSLDCXLWWGMJ-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
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
UMSVYHQZNIJNFQ-UHFFFAOYSA-N C1COC(=O)C1N(C2=CC(=CC=C2)[N+](=O)[O-])C(=O)C3=CC=CO3 Chemical compound C1COC(=O)C1N(C2=CC(=CC=C2)[N+](=O)[O-])C(=O)C3=CC=CO3 UMSVYHQZNIJNFQ-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
DUEBWEOGHPZUHM-UHFFFAOYSA-N C1COC(=O)C1N(C2=CC=CC(=C2)C#N)C(=O)C3=CC=CO3 Chemical compound C1COC(=O)C1N(C2=CC=CC(=C2)C#N)C(=O)C3=CC=CO3 DUEBWEOGHPZUHM-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
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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 claims description 2
ULIWDNGZLDOCOU-UHFFFAOYSA-N CC1=CC=CC(N(C(CCO2)C2=O)C(C2=CC=CO2)=O)=C1C Chemical compound CC1=CC=CC(N(C(CCO2)C2=O)C(C2=CC=CO2)=O)=C1C ULIWDNGZLDOCOU-UHFFFAOYSA-N 0.000 claims description 2
WLCHCXBIAILDRN-UHFFFAOYSA-N CC1CC(C(=O)O1)N(C2=CC(=CC=C2)F)C(=O)C3=CC=CO3 Chemical compound CC1CC(C(=O)O1)N(C2=CC(=CC=C2)F)C(=O)C3=CC=CO3 WLCHCXBIAILDRN-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
WBCKVPXWSGGNIH-UHFFFAOYSA-N COC1=C(C=CC=C1Cl)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound COC1=C(C=CC=C1Cl)N(C2CCOC2=O)C(=O)C3=CC=CO3 WBCKVPXWSGGNIH-UHFFFAOYSA-N 0.000 claims description 2
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 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
125000004799 bromophenyl group Chemical group 0.000 claims description 2
125000000068 chlorophenyl group Chemical group 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
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
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 6
229910052736 halogen Inorganic materials 0.000 claims 6
150000002367 halogens Chemical class 0.000 claims 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 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 1
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 1
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 1
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 1
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 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 claims 1
XSRUOKNTFXEXPP-UHFFFAOYSA-N CC1=C(C=C(C=C1)Cl)N(C2CCOC2=O)C(=O)C3=CC=CO3 Chemical compound CC1=C(C=C(C=C1)Cl)N(C2CCOC2=O)C(=O)C3=CC=CO3 XSRUOKNTFXEXPP-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
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 1
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 1
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 1
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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 1
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 1
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 1
CFLGNBXZYTXDKU-UHFFFAOYSA-N ClC=1C=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C=CC1 Chemical compound ClC=1C=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C=CC1 CFLGNBXZYTXDKU-UHFFFAOYSA-N 0.000 claims 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 1
241000196324 Embryophyta Species 0.000 description 32
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000013543 active substance Substances 0.000 description 20
239000002689 soil Substances 0.000 description 19
230000000694 effects Effects 0.000 description 15
238000002360 preparation method Methods 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
230000000855 fungicidal effect Effects 0.000 description 8
239000000243 solution Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
241000227653 Lycopersicon Species 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
244000061456 Solanum tuberosum Species 0.000 description 6
125000002541 furyl group Chemical group 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000002361 compost Substances 0.000 description 5
239000000758 substrate Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
241000722921 Tulipa gesneriana Species 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
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150000003839 salts Chemical class 0.000 description 3
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230000009885 systemic effect Effects 0.000 description 3
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
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229960001760 dimethyl sulfoxide Drugs 0.000 description 2
235000021186 dishes Nutrition 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000002538 fungal effect Effects 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
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229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000004382 potting Methods 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
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YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-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
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 description 1
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 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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
WNDDFUBZCDNWFA-UHFFFAOYSA-N ClC1=C(NC2CCOC2=O)C=CC=C1 Chemical compound ClC1=C(NC2CCOC2=O)C=CC=C1 WNDDFUBZCDNWFA-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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
241000233629 Phytophthora parasitica Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241001635622 Pythium splendens Species 0.000 description 1
241001622887 Pythium sylvaticum Species 0.000 description 1
241000167589 Rangia Species 0.000 description 1
241000232168 Sinningia 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
206010044565 Tremor Diseases 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
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000013078 crystal Substances 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical group [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
239000002270 dispersing agent Substances 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
ZQURKOAMICBVAW-UHFFFAOYSA-N ethene;manganese Chemical group [Mn].C=C ZQURKOAMICBVAW-UHFFFAOYSA-N 0.000 description 1
KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
238000003898 horticulture Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 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
229920005610 lignin Polymers 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
230000007935 neutral 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
230000001717 pathogenic effect Effects 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000004576 sand 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
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 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
229960002447 thiram Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting 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)

CA000304214A 1977-05-27 1978-05-26 Fungicidally active furancarboxylic acid anilides Expired CA1156665A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2724785.4		1977-05-27
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
CA1156665A true CA1156665A (en)	1983-11-08

Family

ID=6010434

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000304214A Expired CA1156665A (en)	1977-05-27	1978-05-26	Fungicidally active furancarboxylic acid anilides

Country Status (27)

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

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
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 (el)	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
CH637393A5 (en)	1983-07-29
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
2000-11-08	MKEX	Expiry

Publication	Publication Date	Title
CA1050546A (en)	1979-03-13	Derivatives of n-carboxy-alkyl anilides
GB1577702A (en)	1980-10-29	Acylaminotetrahydro - 2 - furanone derivatives and their use as fungicides
PL110213B1 (en)	1980-07-31	Pesticide
CA1156665A (en)	1983-11-08	Fungicidally active furancarboxylic acid anilides
US4075349A (en)	1978-02-21	Microbicidal compositions
CA1108161A (en)	1981-09-01	Fungicidally active cyclopropanecarboxylic acid anilides
US4123554A (en)	1978-10-31	Fungicidal and germicidal benzanilides
US4233308A (en)	1980-11-11	Microbicidal compositions
GB1603758A (en)	1981-11-25	Fungicidally active furancarboxylic acid anilides and their manufacture and use
US4115582A (en)	1978-09-19	N-1,1,2,2-tetrachloro-2-fluoroethylthio benzanilide and its use as fungicide and acaricide
USRE29439E (en)	1977-10-11	Certain 1,2,4-Oxa- and -thiadiazol-5-ylthioalkanoic acid derivatives
CA1127178A (en)	1982-07-06	Microbicidal composition
US4101672A (en)	1978-07-18	Microbicidal alanine thioesters
US4283416A (en)	1981-08-11	Fungicidal, miticidal and ovicidal alkoxycarbonylalkyl-substituted and carbamylalkyl-substituted N-haloalkylthiosulfonamides
KR810001153B1 (ko)	1981-09-22	사이클로프로판 카복실산 아닐리드류의 제조방법
KR810001171B1 (ko)	1981-09-25	푸란 카복실산 아닐리드류의 제조방법
CA1253517A (en)	1989-05-02	N-(CARBAMYLMETHYL)-.alpha.-HALOACETANILIDE COMPOUNDS
PL89203B1 (en)	1976-11-30	2-Chloro-N-(2'-methoxypropyl)- and 2-chloro-N-(2'-ethoxypropyl)-2'',6''-dimethyl-acetanilide as long term weed killers[US4412855A]
IE46469B1 (en)	1983-06-15	New oxadiazole derivatives
GB2033379A (en)	1980-05-21	Fungicidally active acetic acid anilides and their manufacture and use
US3892775A (en)	1975-07-01	3,5-Dimethyl-2-thienyl-(n-haloalkylthiocarboxanilide) herbicides
KR840001934B1 (ko)	1984-10-25	2-설피닐-5-설포닐-1,3,4-티아디아졸 유도체의 제조방법
US4076836A (en)	1978-02-28	Acylated phenylamine thiopropionates useful in combatting plant fungi
KR830002816B1 (ko)	1983-12-26	1,3,4-티아디아졸-2-카복실산 유도체의 제조방법
US3948633A (en)	1976-04-06	3,5-Dimethyl-2-thienylcarboxanilide and 3,5-dimethyl-2-thienyl-(N-haloalkylthiocarboxanilide) herbicides