HU180985B - Fungicide compositions containing anilide derivatives of furane-carbocylic acid - Google Patents

Fungicide compositions containing anilide derivatives of furane-carbocylic acid Download PDF

Info

Publication number: HU180985B
Authority: HU; Hungary
Prior art keywords: carboxylic acid; furan; anilide; furyl; active ingredient
Prior art date: 1977-05-27

Application number

HU78SCHE645A

Other languages

English (en)

Hungarian (hu)

Inventor

Ulrich Buehmann

Reinhold Puttener

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

1978-05-26

Publication date

1983-05-30

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

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

1983-05-30 Publication of HU180985B publication Critical patent/HU180985B/hu

Links

150000003931 anilides Chemical class 0.000 title claims description 11
239000002253 acid Substances 0.000 title claims description 8
239000000417 fungicide Substances 0.000 title claims description 7
239000000203 mixture Substances 0.000 title description 28
230000000855 fungicidal effect Effects 0.000 title description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
XHVDWCKBZSFUDE-UHFFFAOYSA-N n-phenylfuran-2-carboxamide Chemical class C=1C=COC=1C(=O)NC1=CC=CC=C1 XHVDWCKBZSFUDE-UHFFFAOYSA-N 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract 4
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical group OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 90
239000004480 active ingredient Substances 0.000 claims description 42
239000003795 chemical substances by application Substances 0.000 claims description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
239000000969 carrier Substances 0.000 claims description 4
229920005610 lignin Polymers 0.000 claims description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 4
159000000007 calcium salts Chemical class 0.000 claims description 3
WIGLFQRQCVYIKN-UHFFFAOYSA-N BrC=1C=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C=CC1 Chemical group BrC=1C=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C=CC1 WIGLFQRQCVYIKN-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 group 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
235000014113 dietary fatty acids Nutrition 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000000194 fatty acid Substances 0.000 claims description 2
229930195729 fatty acid Natural products 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
QGSPMMHFFLTIQF-UHFFFAOYSA-N C1COC(=O)C1N(C2=CC(=CC=C2)F)C(=O)C3=CC=CO3 Chemical group C1COC(=O)C1N(C2=CC(=CC=C2)F)C(=O)C3=CC=CO3 QGSPMMHFFLTIQF-UHFFFAOYSA-N 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
239000007859 condensation product Substances 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
229920000151 polyglycol Polymers 0.000 claims 1
239000010695 polyglycol Substances 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
125000004432 carbon atom Chemical group C* 0.000 abstract 6
125000001424 substituent group Chemical group 0.000 abstract 3
125000003545 alkoxy group Chemical group 0.000 abstract 2
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
125000004414 alkyl thio group Chemical group 0.000 abstract 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 1
125000004093 cyano group Chemical group *C#N 0.000 abstract 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
241000196324 Embryophyta Species 0.000 description 32
-1 dimethylphenyl Chemical group 0.000 description 31
239000002689 soil Substances 0.000 description 30
150000001875 compounds Chemical class 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
230000000694 effects Effects 0.000 description 16
208000015181 infectious disease Diseases 0.000 description 14
238000002360 preparation method Methods 0.000 description 13
244000061456 Solanum tuberosum Species 0.000 description 10
241000233866 Fungi Species 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000009472 formulation Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
240000003768 Solanum lycopersicum Species 0.000 description 7
239000000758 substrate Substances 0.000 description 7
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
229910052770 Uranium Inorganic materials 0.000 description 6
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 6
239000004927 clay Substances 0.000 description 6
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
230000002538 fungal effect Effects 0.000 description 5
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
241000918584 Pythium ultimum Species 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000002361 compost Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
206010028851 Necrosis Diseases 0.000 description 3
241000233614 Phytophthora Species 0.000 description 3
241000233622 Phytophthora infestans Species 0.000 description 3
240000004713 Pisum sativum Species 0.000 description 3
235000010582 Pisum sativum Nutrition 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
238000011109 contamination Methods 0.000 description 3
230000008029 eradication Effects 0.000 description 3
238000000034 method Methods 0.000 description 3
230000017074 necrotic cell death Effects 0.000 description 3
239000003415 peat Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
230000009885 systemic effect Effects 0.000 description 3
244000291564 Allium cepa Species 0.000 description 2
235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
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 description 2
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 2
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 description 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
240000002395 Euphorbia pulcherrima Species 0.000 description 2
206010017533 Fungal infection Diseases 0.000 description 2
235000000292 Gouania lupuloides Nutrition 0.000 description 2
244000299452 Gouania lupuloides Species 0.000 description 2
208000031888 Mycoses Diseases 0.000 description 2
241001635622 Pythium splendens Species 0.000 description 2
235000002595 Solanum tuberosum Nutrition 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000722921 Tulipa gesneriana Species 0.000 description 2
239000000370 acceptor Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 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
238000005520 cutting process Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000035876 healing Effects 0.000 description 2
238000011081 inoculation 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
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000003449 preventive effect Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 description 1
MHAKUEQWKCWLJY-UHFFFAOYSA-N 3-anilinooxolan-2-one Chemical compound O=C1OCCC1NC1=CC=CC=C1 MHAKUEQWKCWLJY-UHFFFAOYSA-N 0.000 description 1
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 description 1
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
RZHMIKNBONVSQU-UHFFFAOYSA-N 5-chloro-2-methylpyridine-3-carboxamide Chemical compound CC1=NC=C(Cl)C=C1C(N)=O RZHMIKNBONVSQU-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
235000016068 Berberis vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
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 description 1
KMMZVGRXMDDZQW-UHFFFAOYSA-N C(C)C1=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C(=CC=C1)C Chemical compound C(C)C1=C(N(C(=O)C=2OC=CC2)C2C(OCC2)=O)C(=CC=C1)C KMMZVGRXMDDZQW-UHFFFAOYSA-N 0.000 description 1
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 description 1
TXICBXXJEJVGJW-UHFFFAOYSA-N CC(C)C(C=CC=C1C(C)C)=C1N(C(CCO1)C1=O)C(C1=CC=CO1)=O Chemical compound CC(C)C(C=CC=C1C(C)C)=C1N(C(CCO1)C1=O)C(C1=CC=CO1)=O TXICBXXJEJVGJW-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
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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 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
241000208150 Geraniaceae 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
206010061217 Infestation Diseases 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
235000019738 Limestone Nutrition 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
241000208181 Pelargonium Species 0.000 description 1
241000580814 Pelargonium peltatum 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
241000233639 Pythium Species 0.000 description 1
241001622887 Pythium sylvaticum 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
240000003864 Ulex europaeus Species 0.000 description 1
241000219094 Vitaceae Species 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
239000002671 adjuvant Substances 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
238000003556 assay Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
125000004799 bromophenyl group Chemical group 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 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
230000001419 dependent effect Effects 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
235000021021 grapes Nutrition 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
238000003898 horticulture Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000011534 incubation Methods 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
239000006028 limestone Substances 0.000 description 1
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
RYGGCHSNKJIGNF-UHFFFAOYSA-N n-(3-chloro-2-methylphenyl)furan-2-carboxamide Chemical compound CC1=C(Cl)C=CC=C1NC(=O)C1=CC=CO1 RYGGCHSNKJIGNF-UHFFFAOYSA-N 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
231100001184 nonphytotoxic Toxicity 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
210000002741 palatine tonsil Anatomy 0.000 description 1
244000052769 pathogen Species 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
208000018655 severe necrosis Diseases 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
KKDONKAYVYTWGY-UHFFFAOYSA-M sodium;2-(methylamino)ethanesulfonate Chemical compound [Na+].CNCCS([O-])(=O)=O KKDONKAYVYTWGY-UHFFFAOYSA-M 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 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)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Furan Compounds (AREA)

HU78SCHE645A 1977-05-27 1978-05-26 Fungicide compositions containing anilide derivatives of furane-carbocylic acid HU180985B (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
HU180985B true HU180985B (en)	1983-05-30

Family

ID=6010434

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU78SCHE645A HU180985B (en)	1977-05-27	1978-05-26	Fungicide compositions containing anilide derivatives of furane-carbocylic acid

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 NZ NZ187271A patent/NZ187271A/xx unknown
- 1978-05-15 CS CS783117A patent/CS194200B2/cs 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 PT PT68085A patent/PT68085A/pt unknown
- 1978-05-24 IE IE1028/78A patent/IE46922B1/en unknown
- 1978-05-24 EG EG332/78A patent/EG13300A/xx active
- 1978-05-25 IT IT23778/78A patent/IT1096327B/it active
- 1978-05-25 DD DD78205585A patent/DD136092A5/xx unknown
- 1978-05-25 RO RO7894165A patent/RO75073A/ro unknown
- 1978-05-26 ZA ZA00783037A patent/ZA783037B/xx unknown
- 1978-05-26 NO NO781837A patent/NO149431C/no unknown
- 1978-05-26 SU SU782621054A patent/SU727108A3/ru active
- 1978-05-26 BG BG039861A patent/BG28687A3/xx unknown
- 1978-05-26 CA CA000304214A patent/CA1156665A/en not_active Expired
- 1978-05-26 HU HU78SCHE645A patent/HU180985B/hu unknown
- 1978-05-26 SU SU2617650A patent/SU725560A1/ru active
- 1978-05-26 GR GR56345A patent/GR71669B/el unknown
- 1978-05-27 AR AR272307A patent/AR224234A1/es active

Also Published As

Publication number	Publication date
AR224234A1 (es)	1981-11-13
BG28687A3 (bg)	1980-06-16
PL207070A1 (pl)	1979-02-26
IL54720A (en)	1983-07-31
PL110264B1 (en)	1980-07-31
RO75073A (ro)	1980-10-30
DK192278A (da)	1978-11-28
EG13300A (en)	1981-12-31
MX5432E (es)	1983-08-05
ES469811A1 (es)	1978-12-16
YU97778A (en)	1983-01-21
NZ187271A (en)	1980-10-08
IT1096327B (it)	1985-08-26
NO149431B (no)	1984-01-09
CA1156665A (en)	1983-11-08
SU725560A3 (en)	1980-03-30
PT68085A (de)	1978-06-01
IE46922B1 (en)	1983-11-02
BR7803217A (pt)	1979-01-16
NO781837L (no)	1978-11-28
CH637393A5 (en)	1983-07-29
DD136092A5 (de)	1979-06-20
FI781211A7 (fi)	1978-11-28
IT7823778A0 (it)	1978-05-25
NO149431C (no)	1984-04-25
PH15611A (en)	1983-02-28
SU727108A3 (ru)	1980-04-05
TR20539A (tr)	1981-10-21
SU725560A1 (ru)	1980-03-30
IE781028L (en)	1978-11-27
ZA783037B (en)	1979-06-27
IL54720A0 (en)	1978-07-31
CS194200B2 (en)	1979-11-30
GR71669B (cs)	1983-06-20

Publication	Publication Date	Title
IL28955A (en)	1971-07-28	Fungicidal and fungistatic preparations containing n-dialkylaminoalkyl-carbamic and-thiocarbamic acid esters
DE2643477C2 (cs)	1991-01-31
PL98627B1 (pl)	1978-05-31	Srodek szkodnikobojczy
BG62991B1 (bg)	2001-01-31	Фунгициден състав и метод за контрол на гъбично заразяване
DE2643403C2 (de)	1987-01-22	Thiocarbonsäurederivate, Verfahren zu deren Herstellung und diese enthaltende Mittel
DE2813335C2 (de)	1987-04-09	N-acylierte N-Alkylaniline, Verfahren zu ihrer Herstellung sowie mikrobizide Mittel enthaltend diese als Wirkstoffe
WO2017148226A1 (zh)	2017-09-08	一种氟苯噁唑类化合物及其用途
HU180985B (en)	1983-05-30	Fungicide compositions containing anilide derivatives of furane-carbocylic acid
HU184201B (en)	1984-07-30	Fungicide compositions containing anilides of cyclopropane-carboxylic acid and process for producing these compounds
US4207338A (en)	1980-06-10	Microbicidal composition
DE2902861A1 (de)	1979-08-02	Mikrobizide mittel
DE2724785A1 (de)	1978-12-14	Furancarbonsaeureanilide, fungizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung
SU519109A3 (ru)	1976-06-25	Фунгицидное средство
JP4205060B2 (ja)	2009-01-07	殺線虫剤としてのシアノメチルトリチオカーボネート類
KR810001153B1 (ko)	1981-09-22	사이클로프로판 카복실산 아닐리드류의 제조방법
KR810001171B1 (ko)	1981-09-25	푸란 카복실산 아닐리드류의 제조방법
HU182612B (en)	1984-02-28	Fungicide compositions containing acetanilide derivatives as active agents, and process for producing these active agents
KR810002007B1 (ko)	1981-12-15	제초용 조성물
DE2643445A1 (de)	1977-04-07	Mikrobizide mittel
KR810000852B1 (ko)	1981-08-10	신규 안식향산 아닐리드 유도체의 제조방법
DE1810581C3 (de)	1977-12-29	N-Acyl-p-dialkylamino-phenylhydrazone, Verfahren zu ihrer Herstellung und deren Verwendung zur Bekämpfung von phytopathogene Pilzen
CH614102A5 (en)	1979-11-15	Pesticides
CH631602A5 (en)	1982-08-31	Microbicides
JPS613A (ja)	1986-01-06	植物病害防除剤
CH625784A5 (en)	1981-10-15	Microbicides