DD262359A5 - Gyanoacetamidderivate mit fungizider wirksamkeit - Google Patents

Gyanoacetamidderivate mit fungizider wirksamkeit Download PDF

Info

Publication number: DD262359A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; compounds; compound; radical; alkyl
Prior art date: 1986-04-15

Application number

DD87301763A

Other languages

German (de)

English (en)

Inventor

Augusto Menconi

Giovanni Camaggi

Franco Gozzo

Luigi Mirenna

Carlo Garavaglia

Original Assignee

��@�K@�K@�Kk��

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.)

1986-04-15

Filing date

1987-04-13

Publication date

1988-11-30

1987-04-13 Application filed by ��@�K@�K@�Kk�� filed Critical ��@�K@�K@�Kk��

1988-11-30 Publication of DD262359A5 publication Critical patent/DD262359A5/de

Links

230000000855 fungicidal effect Effects 0.000 title claims abstract description 18
239000000417 fungicide Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 69
239000000203 mixture Substances 0.000 claims abstract description 33
239000004480 active ingredient Substances 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 abstract description 12
239000007787 solid Substances 0.000 abstract description 12
125000001153 fluoro group Chemical group F* 0.000 abstract description 11
239000007788 liquid Substances 0.000 abstract description 8
125000003342 alkenyl group Chemical group 0.000 abstract description 6
229910052760 oxygen Inorganic materials 0.000 abstract description 6
229910052717 sulfur Inorganic materials 0.000 abstract description 6
125000000732 arylene group Chemical group 0.000 abstract description 5
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical class NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 abstract description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract description 3
239000000654 additive Substances 0.000 abstract description 3
125000002947 alkylene group Chemical group 0.000 abstract description 3
239000003795 chemical substances by application Substances 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
238000000034 method Methods 0.000 description 20
-1 alkynyl radical Chemical class 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
241000196324 Embryophyta Species 0.000 description 15
238000002360 preparation method Methods 0.000 description 14
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
241001281803 Plasmopara viticola Species 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
230000003449 preventive effect Effects 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
235000013877 carbamide Nutrition 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
206010017533 Fungal infection Diseases 0.000 description 7
208000031888 Mycoses Diseases 0.000 description 7
239000000243 solution Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
238000011081 inoculation Methods 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 5
239000004202 carbamide Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
BABBPCGMXBHVSX-UHFFFAOYSA-N 4-(1,2,2,2-tetrafluoroethoxy)aniline Chemical compound NC1=CC=C(OC(F)C(F)(F)F)C=C1 BABBPCGMXBHVSX-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
150000003672 ureas Chemical class 0.000 description 4
XRMDUTAWWNLZCX-UHFFFAOYSA-N 2-(1,2,2,2-tetrafluoroethoxy)ethylurea Chemical compound NC(=O)NCCOC(F)C(F)(F)F XRMDUTAWWNLZCX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000005756 Cymoxanil Substances 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241000219095 Vitis Species 0.000 description 3
235000009754 Vitis X bourquina Nutrition 0.000 description 3
235000012333 Vitis X labruscana Nutrition 0.000 description 3
235000014787 Vitis vinifera Nutrition 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001414 amino alcohols Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000007034 nitrosation reaction Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000002689 soil Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
VSQOTARNFIXGPG-UHFFFAOYSA-N 2-cyano-n-[4-(1,2,2,2-tetrafluoroethoxy)phenyl]acetamide Chemical compound FC(F)(F)C(F)OC1=CC=C(NC(=O)CC#N)C=C1 VSQOTARNFIXGPG-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
XVJRYTSPCCYPLJ-UHFFFAOYSA-N [4-(1,2,2,2-tetrafluoroethoxy)phenyl]urea Chemical compound NC(=O)NC1=CC=C(OC(F)C(F)(F)F)C=C1 XVJRYTSPCCYPLJ-UHFFFAOYSA-N 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000001143 conditioned effect Effects 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000005796 dehydrofluorination reaction Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
230000035876 healing Effects 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
238000011534 incubation 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
239000013612 plasmid Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
239000000843 powder Substances 0.000 description 2
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
KAOQVXHBVNKNHA-UHFFFAOYSA-N propyl nitrite Chemical compound CCCON=O KAOQVXHBVNKNHA-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
FCEUVAQYYKMPRC-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluorobutan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)F FCEUVAQYYKMPRC-UHFFFAOYSA-N 0.000 description 1
NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 1
GEQZTCMVWVDEDF-UHFFFAOYSA-N 2-cyanoacetyl chloride Chemical compound ClC(=O)CC#N GEQZTCMVWVDEDF-UHFFFAOYSA-N 0.000 description 1
CLAHOZSYMRNIPY-UHFFFAOYSA-N 2-hydroxyethylurea Chemical compound NC(=O)NCCO CLAHOZSYMRNIPY-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 1
TWYWYRSZTZQNHE-UHFFFAOYSA-N 4-(cyclohexylideneamino)phenol Chemical compound C1=CC(O)=CC=C1N=C1CCCCC1 TWYWYRSZTZQNHE-UHFFFAOYSA-N 0.000 description 1
USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
125000006414 CCl Chemical group ClC* 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
239000004117 Lignosulphonate Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
FBPFZTCFMRRESA-NQAPHZHOSA-N Sorbitol Polymers OCC(O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-NQAPHZHOSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
238000005905 alkynylation reaction Methods 0.000 description 1
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
230000002605 anti-dotal effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
244000038559 crop plants Species 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
239000003925 fat Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
244000053095 fungal pathogen Species 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 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
150000002576 ketones Chemical class 0.000 description 1
235000019357 lignosulphonate Nutrition 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000009935 nitrosation Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000006072 paste Substances 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000003756 stirring Methods 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
125000005490 tosylate group Chemical group 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/50—Y being a hydrogen or an acyclic carbon atom

Landscapes

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

DD87301763A 1986-04-15 1987-04-13 Gyanoacetamidderivate mit fungizider wirksamkeit DD262359A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT20081/86A IT1188653B (it)	1986-04-15	1986-04-15	Cianoacetoammido-derivati ad azione antifungina

Publications (1)

Publication Number	Publication Date
DD262359A5 true DD262359A5 (de)	1988-11-30

Family

ID=11163649

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87301763A DD262359A5 (de)	1986-04-15	1987-04-13	Gyanoacetamidderivate mit fungizider wirksamkeit

Country Status (19)

Country	Link
US (1)	US4874786A (fr)
EP (1)	EP0250744B1 (fr)
JP (1)	JPS62242656A (fr)
KR (1)	KR940010278B1 (fr)
AR (1)	AR242557A1 (fr)
AT (1)	ATE81847T1 (fr)
AU (1)	AU603357B2 (fr)
BR (1)	BR8701808A (fr)
CA (1)	CA1325810C (fr)
CS (1)	CS268689B2 (fr)
DD (1)	DD262359A5 (fr)
DE (1)	DE3782362T2 (fr)
ES (1)	ES2046181T3 (fr)
HU (1)	HU201647B (fr)
IL (1)	IL82175A (fr)
IT (1)	IT1188653B (fr)
NZ (1)	NZ219949A (fr)
SU (1)	SU1553005A3 (fr)
ZA (1)	ZA872567B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5231109A (en) *	1986-09-10	1993-07-27	Bayer Aktiengesellschaft	2-cyano-2-alkoximino-acetamides
DE3630732A1 (de) *	1986-09-10	1988-03-17	Bayer Ag	2-cyano-2-alkoximino-acetamide
FR2646847B1 (fr) *	1989-05-12	1991-07-12	Rhone Poulenc Sante	N-phenyl amides, leurs procedes de preparation et les medicaments les contenant
US6231660B1 (en) *	1997-12-22	2001-05-15	The National Lime And Stone Co.	Manufactured granular substrate and method for producing the same
US8404259B2 (en) *	2005-10-11	2013-03-26	The National Lime And Stone Co.	Dispersible granular substrate for pesticide delivery

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3979518A (en) *	1975-09-11	1976-09-07	E. I. Du Pont De Nemours And Company	Fungicidal alkoxy substituted 2-cyanoacetamide derivatives
GB1452256A (en) *	1975-02-26	1976-10-13	Du Pont	Carbamoylacetamide derivatives
DK333276A (da) *	1975-09-11	1977-03-12	Du Pont	Fungicide, substituerede 2-cyanoacet-amidderivater
DE2837863A1 (de) *	1978-09-04	1980-03-13	Ciba Geigy Ag	Oxim-derivate zum schutz von pflanzenkulturen
DE3327013A1 (de) *	1983-07-27	1985-02-07	Basf Ag, 6700 Ludwigshafen	2-cyan-2-oxyimino-n-carbamoylacetamide, diese enthaltende fungizide und verfahren zu ihrer herstellung

1986
- 1986-04-15 IT IT20081/86A patent/IT1188653B/it active
1987
- 1987-04-09 US US07/036,465 patent/US4874786A/en not_active Expired - Fee Related
- 1987-04-09 ZA ZA872567A patent/ZA872567B/xx unknown
- 1987-04-09 AU AU71359/87A patent/AU603357B2/en not_active Ceased
- 1987-04-10 JP JP62087270A patent/JPS62242656A/ja active Pending
- 1987-04-10 NZ NZ219949A patent/NZ219949A/xx unknown
- 1987-04-10 IL IL82175A patent/IL82175A/xx unknown
- 1987-04-13 DD DD87301763A patent/DD262359A5/de not_active IP Right Cessation
- 1987-04-13 CS CS872625A patent/CS268689B2/cs unknown
- 1987-04-14 CA CA000534685A patent/CA1325810C/fr not_active Expired - Fee Related
- 1987-04-14 SU SU874202402A patent/SU1553005A3/ru active
- 1987-04-14 AR AR87307288A patent/AR242557A1/es active
- 1987-04-14 HU HU871647A patent/HU201647B/hu not_active IP Right Cessation
- 1987-04-15 EP EP87105598A patent/EP0250744B1/fr not_active Expired - Lifetime
- 1987-04-15 KR KR1019870003587A patent/KR940010278B1/ko not_active Expired - Fee Related
- 1987-04-15 ES ES198787105598T patent/ES2046181T3/es not_active Expired - Lifetime
- 1987-04-15 AT AT87105598T patent/ATE81847T1/de not_active IP Right Cessation
- 1987-04-15 BR BR8701808A patent/BR8701808A/pt unknown
- 1987-04-15 DE DE8787105598T patent/DE3782362T2/de not_active Expired - Fee Related

Also Published As

Publication number	Publication date
KR940010278B1 (ko)	1994-10-22
EP0250744B1 (fr)	1992-10-28
AU7135987A (en)	1987-10-22
EP0250744A2 (fr)	1988-01-07
ATE81847T1 (de)	1992-11-15
AR242557A1 (es)	1993-04-30
JPS62242656A (ja)	1987-10-23
BR8701808A (pt)	1988-01-26
DE3782362D1 (de)	1992-12-03
IL82175A (en)	1992-02-16
CS268689B2 (en)	1990-04-11
IT8620081A0 (it)	1986-04-15
CA1325810C (fr)	1994-01-04
AU603357B2 (en)	1990-11-15
US4874786A (en)	1989-10-17
IT1188653B (it)	1988-01-20
IT8620081A1 (it)	1987-10-15
ES2046181T3 (es)	1994-02-01
DE3782362T2 (de)	1993-05-19
HUT44400A (en)	1988-03-28
NZ219949A (en)	1990-07-26
KR870009988A (ko)	1987-11-30
ZA872567B (en)	1987-11-25
CS262587A2 (en)	1989-07-12
IL82175A0 (en)	1987-10-30
EP0250744A3 (en)	1989-03-22
SU1553005A3 (ru)	1990-03-23
HU201647B (en)	1990-12-28

Legal Events

Date	Code	Title	Description
1996-04-25	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69028461T2 (de)	1997-02-06	Triazin-derivate und unkrautvertilgungsmittel daraus
DE68906668T2 (de)	1993-08-26	Guanidin-derivate, ihre herstellung und insektizide.
DE2661042C2 (fr)	1989-11-09
DE2632581C2 (de)	1982-07-15	Substituierte Nitrodiphenylether, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel
CH640108A5 (de)	1983-12-30	Unkrautvernichtungsmittel.
EP0056969B1 (fr)	1985-11-06	Dérivés substitués de phénylsulfonylurées, intermédiaires et procédé pour leur préparation et compositions herbicides contenant les dérivés
EP0037971B1 (fr)	1983-12-21	Cyanoguanidines trisubstituées, procédé pour leur préparation et leur utilisation comme fongicides
DD144499A5 (de)	1980-10-22	Schimmelbekaempfungsmittel
EP0029908B1 (fr)	1982-12-22	6H-1,2,4,6-thiatriazin-1,1-dioxydes, herbicides les contenant, leur application comme herbicides et procédé pour leur préparation
DD262359A5 (de)	1988-11-30	Gyanoacetamidderivate mit fungizider wirksamkeit
DE2405479C2 (de)	1982-12-30	N-substituierte Chloracetanilide, Verfahren zu deren Herstellung und Mittel zur Beeinflussung des Pflanzenwachstums
EP0291851A2 (fr)	1988-11-23	Sulfonylurées herbicides, leur procédé de préparation et leur utilisation pour influencer la croissance des plantes
DE2824126C2 (de)	1984-06-20	Tetrahydro-1,3,5-thiadiazin-4-on-Verbindungen
EP0010692B1 (fr)	1982-06-23	N-m-Anilidocarbamates, herbicides les contenant et procédé pour leur préparation ainsi que procédé pour contrôler la croissance de plantes indésirables
DE2643403A1 (de)	1977-04-07	Mikrobizide mittel
DD240885A5 (de)	1986-11-19	Verfahren zur herstellung von neuen n- und gegebenenfalls n'-substituierten n-(dichloracetyl)-glycinamiden
DE2919825C2 (fr)	1988-09-01
DE2626828A1 (de)	1977-12-22	Neue carbamidsaeureoximester, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
EP0154273B1 (fr)	1989-09-13	Compositions fongicides
DE2061133A1 (de)	1971-06-24	Pestizide Verbindung,Verfahren zu ihrer Herstellung und Verwendung
EP0037526A1 (fr)	1981-10-14	Acétanilides substitués, procédé pour les préparer et leur utilisation comme herbicides
DE2328728A1 (de)	1975-01-09	Systemisch-fungizide mittel
DD201969A5 (de)	1983-08-24	Fungizide mittel
DD144354A5 (de)	1980-10-15	Insektizides mittel
EP0007066A1 (fr)	1980-01-23	4-Alkyl- et 4-allyl-thio-, sulfinyl- et sulfonyl-méthyl-2-amino-6-N,N'-diméthylcarbamoyloxy-pyrimidines, procédé pour leur préparation, compositions les contenant et leur utilisation comme insecticides