CS268689B2 - Means for vine's peronospore supression and method of efficient substances production - Google Patents

Means for vine's peronospore supression and method of efficient substances production Download PDF

Info

Publication number: CS268689B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; group; compound; align; carbon atoms
Prior art date: 1986-04-15

Application number

CS872625A

Other languages

Czech (cs)

English (en)

Other versions

CS262587A2 (en

Inventor

Augusto Menconi

Giovanni Camaggi

Franco Gozzo

Luigi Mirenna

Carlo Garavaglia

Original Assignee

Montedison Spa

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

1990-04-11

1987-04-13 Application filed by Montedison Spa filed Critical Montedison Spa

1989-07-12 Publication of CS262587A2 publication Critical patent/CS262587A2/cs

1990-04-11 Publication of CS268689B2 publication Critical patent/CS268689B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 15
239000000126 substance Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 62
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 9
125000002947 alkylene group Chemical group 0.000 claims abstract description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
239000000203 mixture Substances 0.000 claims description 30
239000004480 active ingredient Substances 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
-1 alkali metal nitrite Chemical class 0.000 claims description 8
239000007787 solid Substances 0.000 claims description 7
241001223281 Peronospora Species 0.000 claims description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
239000004202 carbamide Substances 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
BODVQMUXDOPTHM-UHFFFAOYSA-N n-methoxy-2-oxo-2-[4-(1,2,2,2-tetrafluoroethoxy)anilino]ethanimidoyl cyanide Chemical group CON=C(C#N)C(=O)NC1=CC=C(OC(F)C(F)(F)F)C=C1 BODVQMUXDOPTHM-UHFFFAOYSA-N 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
150000007522 mineralic acids Chemical class 0.000 claims 1
HYRWAPOHUIVYRD-UHFFFAOYSA-N n-methoxy-2-oxo-2-[[4-(1,2,2,2-tetrafluoroethoxy)phenyl]carbamoylamino]ethanimidoyl cyanide Chemical group CON=C(C#N)C(=O)NC(=O)NC1=CC=C(OC(F)C(F)(F)F)C=C1 HYRWAPOHUIVYRD-UHFFFAOYSA-N 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 abstract description 3
125000000304 alkynyl group Chemical group 0.000 abstract description 3
208000031888 Mycoses Diseases 0.000 abstract description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000000732 arylene group Chemical group 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000002360 preparation method Methods 0.000 description 15
241000196324 Embryophyta Species 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
241001281803 Plasmopara viticola Species 0.000 description 11
230000000855 fungicidal effect Effects 0.000 description 11
239000002904 solvent Substances 0.000 description 11
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
230000003449 preventive effect Effects 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
235000013877 carbamide Nutrition 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
239000002585 base Substances 0.000 description 5
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical class NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 5
238000011081 inoculation Methods 0.000 description 5
239000000243 solution Substances 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
150000001412 amines Chemical class 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 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
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 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
239000005756 Cymoxanil Substances 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241000233866 Fungi Species 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
240000006365 Vitis vinifera Species 0.000 description 3
235000014787 Vitis vinifera Nutrition 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001414 amino alcohols Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
238000007034 nitrosation reaction Methods 0.000 description 3
150000002923 oximes Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
150000003672 ureas Chemical class 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-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
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
DCWUFLVSAPSHOH-UHFFFAOYSA-N ON=C(C#N)C(=O)NC(=O)NCCOC(F)C(F)(F)F Chemical compound ON=C(C#N)C(=O)NC(=O)NCCOC(F)C(F)(F)F DCWUFLVSAPSHOH-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000013543 active substance Substances 0.000 description 2
238000004378 air conditioning Methods 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
239000003849 aromatic solvent Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
239000003925 fat Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000007789 gas Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride 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
238000000655 nuclear magnetic resonance spectrum Methods 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
KAOQVXHBVNKNHA-UHFFFAOYSA-N propyl nitrite Chemical compound CCCON=O KAOQVXHBVNKNHA-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
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
HJOHCZLSKXJKIT-UHFFFAOYSA-N 2-cyano-2-hydroxyimino-N-[[4-(1,2,2,2-tetrafluoroethoxy)phenyl]carbamoyl]acetamide Chemical compound ON=C(C#N)C(=O)NC(=O)NC1=CC=C(OC(F)C(F)(F)F)C=C1 HJOHCZLSKXJKIT-UHFFFAOYSA-N 0.000 description 1
CLAHOZSYMRNIPY-UHFFFAOYSA-N 2-hydroxyethylurea Chemical compound NC(=O)NCCO CLAHOZSYMRNIPY-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
244000215068 Acacia senegal Species 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
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
206010017533 Fungal infection Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 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
239000005909 Kieselgur Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
PIHDBCGSNDYLBA-UHFFFAOYSA-N ON=C(C#N)C(=O)NC1=CC=C(OC(F)C(F)(F)F)C=C1 Chemical compound ON=C(C#N)C(=O)NC1=CC=C(OC(F)C(F)(F)F)C=C1 PIHDBCGSNDYLBA-UHFFFAOYSA-N 0.000 description 1
241000233654 Oomycetes Species 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
239000004113 Sepiolite 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
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 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 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
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000004996 alkyl benzenes 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
235000012211 aluminium silicate Nutrition 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000000729 antidote Substances 0.000 description 1
229940075522 antidotes Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 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
230000015572 biosynthetic process Effects 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
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
230000001586 eradicative effect Effects 0.000 description 1
150000002148 esters Chemical class 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
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
239000000417 fungicide 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
150000002466 imines Chemical class 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000007529 inorganic bases Chemical class 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
150000004658 ketimines Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
FTVCMIRADWZEOX-UHFFFAOYSA-N n-methoxy-2-(2-methoxyethylcarbamoylamino)-2-oxoethanimidoyl cyanide Chemical compound COCCNC(=O)NC(=O)C(C#N)=NOC FTVCMIRADWZEOX-UHFFFAOYSA-N 0.000 description 1
MTGRJSDDIYWNIC-UHFFFAOYSA-N n-methoxy-2-oxo-2-[2-(1,2,2,2-tetrafluoroethoxy)ethylcarbamoylamino]ethanimidoyl cyanide Chemical compound CON=C(C#N)C(=O)NC(=O)NCCOC(F)C(F)(F)F MTGRJSDDIYWNIC-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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
230000009935 nitrosation Effects 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 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
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
238000005292 vacuum distillation Methods 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)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

CS872625A 1986-04-15 1987-04-13 Means for vine's peronospore supression and method of efficient substances production CS268689B2 (en)

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 (2)

Publication Number	Publication Date
CS262587A2 CS262587A2 (en)	1989-07-12
CS268689B2 true CS268689B2 (en)	1990-04-11

Family

ID=11163649

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS872625A CS268689B2 (en)	1986-04-15	1987-04-13	Means for vine's peronospore supression and method of efficient substances production

Country Status (19)

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

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
WO2007044743A2 (en) *	2005-10-11	2007-04-19	The Andersons, Inc.	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
BE870067A (fr) *	1978-09-04	1979-02-28	Ciba Geigy	Derives d'oximes pour la protection des cultures
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 ZA ZA872567A patent/ZA872567B/xx unknown
- 1987-04-09 AU AU71359/87A patent/AU603357B2/en not_active Ceased
- 1987-04-09 US US07/036,465 patent/US4874786A/en not_active Expired - Fee Related
- 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 HU HU871647A patent/HU201647B/hu not_active IP Right Cessation
- 1987-04-14 SU SU874202402A patent/SU1553005A3/ru active
- 1987-04-14 CA CA000534685A patent/CA1325810C/en not_active Expired - Fee Related
- 1987-04-14 AR AR87307288A patent/AR242557A1/es active
- 1987-04-15 AT AT87105598T patent/ATE81847T1/de not_active IP Right Cessation
- 1987-04-15 ES ES198787105598T patent/ES2046181T3/es not_active Expired - Lifetime
- 1987-04-15 DE DE8787105598T patent/DE3782362T2/de not_active Expired - Fee Related
- 1987-04-15 KR KR1019870003587A patent/KR940010278B1/ko not_active Expired - Fee Related
- 1987-04-15 EP EP87105598A patent/EP0250744B1/en not_active Expired - Lifetime
- 1987-04-15 BR BR8701808A patent/BR8701808A/pt unknown

Also Published As

Publication number	Publication date
EP0250744A2 (en)	1988-01-07
KR870009988A (ko)	1987-11-30
AR242557A1 (es)	1993-04-30
ATE81847T1 (de)	1992-11-15
IL82175A0 (en)	1987-10-30
US4874786A (en)	1989-10-17
NZ219949A (en)	1990-07-26
DE3782362D1 (de)	1992-12-03
JPS62242656A (ja)	1987-10-23
BR8701808A (pt)	1988-01-26
ES2046181T3 (es)	1994-02-01
HU201647B (en)	1990-12-28
EP0250744A3 (en)	1989-03-22
HUT44400A (en)	1988-03-28
AU7135987A (en)	1987-10-22
AU603357B2 (en)	1990-11-15
IT1188653B (it)	1988-01-20
KR940010278B1 (ko)	1994-10-22
DD262359A5 (de)	1988-11-30
IT8620081A1 (it)	1987-10-15
EP0250744B1 (en)	1992-10-28
IL82175A (en)	1992-02-16
ZA872567B (en)	1987-11-25
DE3782362T2 (de)	1993-05-19
IT8620081A0 (it)	1986-04-15
CS262587A2 (en)	1989-07-12
SU1553005A3 (ru)	1990-03-23
CA1325810C (en)	1994-01-04

Publication	Publication Date	Title
CA2195064C (en)	2000-02-01	Amino-acid amide derivatives, processes for preparing the same, agricultural or horticultural fungicides, and method for killing fungi
DE2515091C2 (de)	1987-04-16	N-Acyl-N-phenyl-alaninderivate und -glycinderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende fungizide Mittel
US3764624A (en)	1973-10-09	N-substituted-2,6-dinitro-3-(alkoxy or alkylthio)-4-substituted-aniline compounds
CZ279334B6 (cs)	1995-04-12	Prostředek k potlačování škůdců
DK154651B (da)	1988-12-05	Substituerede n-(1'-alkoxy-, -alkylthio- og -aminocarbonyl-alkyl)-n-aminoacetyl-aniliner og salte deraf med uorganiske og organiske syrer til bekaempelse af fytopatogene svampe, fungicid og fremgangsmaade til bekaempelse af plantepatogene svampe eller til forebyggelse af svampeangreb
IL35271A (en)	1974-11-29	History of 1, 1, 1 - Trichloroethane, their preparation and use as pesticides
HU183176B (en)	1984-04-28	Fungicide, bactericide and algicide compositions containing 2-dihalo-methylene-3-halo-3-alkoxycarbonyl-5-oxo-pyrrolidine derivatives as active substances and process for preparing the active substance
CS268689B2 (en)	1990-04-11	Means for vine's peronospore supression and method of efficient substances production
US3378437A (en)	1968-04-16	Acaricidal agents
DK149363B (da)	1986-05-20	N-(1'-alkylthiocarbonyl-ethyl)-n-acetyl-anilinderivater til anvendelse til bekaempelse af fytopatogene svampe samt middel og fremgangsmaade til bekaempelse af fytopatogene svampe
JP2525199B2 (ja)	1996-08-14	シクロヘキサン誘導体およびそれを有効成分とする除草剤
EP0003430B1 (en)	1982-01-06	Novel 2,6-dinitrobenzenamines, their preparation, composition containing them and their use as fungicides
KR890003834B1 (ko)	1989-10-05	치환된 말레이미드의 제조방법
US4156017A (en)	1979-05-22	Pesticides
JP3844533B2 (ja)	2006-11-15	２，６−ジクロロイソニコチン酸フェネチルアミド誘導体及び植物病害防除剤
HU193422B (en)	1987-10-28	Fungicide compositions containing benzyl-oycloalkenyl-urea-derivatives as active, agents and process for producing the active agents
CS207781B2 (en)	1981-08-31	Herbicide means and method of making the active substances
CS232736B2 (en)	1985-02-14	Fungicide agent and method of active component production
PL94958B1 (es)	1977-09-30
CA1061354A (en)	1979-08-28	3-cyanamino-2,6-dinitroanilines
JPH0247993B2 (es)	1990-10-23
US3297521A (en)	1967-01-10	Fungus control with 4-(phenylthiomethyl) anilines
NZ208933A (en)	1986-11-12	Biscyclohexylamine-alkane derivatives and fungicidal compositions
US4397869A (en)	1983-08-09	Combating fungi with N-sulphenylated ureas
CA1143742A (en)	1983-03-29	Dichloromaleic acid diamide derivatives, a process for their preparation and their use as fungicides