CS253747B2 - Fungicide and process for preparing active compound - Google Patents

Fungicide and process for preparing active compound Download PDF

Info

Publication number: CS253747B2
Authority: CS; Czechoslovakia
Prior art keywords: ethyl; nicotinamide; bromo; compound; trichlorophenoxy
Prior art date: 1985-04-04

Application number

CS861793A

Other languages

Czech (cs)

English (en)

Inventor

Hans-Peter Isenring

Hugo Ziegler

Original Assignee

Hoffmann La Roche

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.)

1985-04-04

Filing date

1986-03-15

Publication date

1987-12-17

1986-03-15 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1987-12-17 Publication of CS253747B2 publication Critical patent/CS253747B2/cs

Links

150000001875 compounds Chemical class 0.000 title claims description 90
230000000855 fungicidal effect Effects 0.000 title claims description 12
239000000417 fungicide Substances 0.000 title description 2
238000004519 manufacturing process Methods 0.000 title description 2
239000000203 mixture Substances 0.000 claims description 55
-1 2 , 4-dichloro-6-methylphenyl Chemical group 0.000 claims description 41
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
239000002253 acid Substances 0.000 claims description 38
239000004480 active ingredient Substances 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 18
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
238000000034 method Methods 0.000 claims description 13
DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
238000009472 formulation Methods 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
235000001968 nicotinic acid Nutrition 0.000 claims description 2
239000011664 nicotinic acid Substances 0.000 claims description 2
229960003512 nicotinic acid Drugs 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
RFEKLPPLEUHHBC-UHFFFAOYSA-N 5-bromo-n-[2-(2,6-dichlorophenoxy)ethyl]-n-methylpyridine-3-carboxamide Chemical compound C=1N=CC(Br)=CC=1C(=O)N(C)CCOC1=C(Cl)C=CC=C1Cl RFEKLPPLEUHHBC-UHFFFAOYSA-N 0.000 claims 1
FCLYOZVHQBILGZ-UHFFFAOYSA-N 5-bromo-n-[2-(3,5-dichloro-2-methylphenoxy)ethyl]-n-methylpyridine-3-carboxamide Chemical compound C=1N=CC(Br)=CC=1C(=O)N(C)CCOC1=CC(Cl)=CC(Cl)=C1C FCLYOZVHQBILGZ-UHFFFAOYSA-N 0.000 claims 1
101100022176 Mus musculus Gstz1 gene Proteins 0.000 claims 1
150000001555 benzenes Chemical class 0.000 claims 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 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 claims 1
OBLVPWTUALCMGD-UHFFFAOYSA-N pyridin-1-ium-3-carboxamide;chloride Chemical compound Cl.NC(=O)C1=CC=CN=C1 OBLVPWTUALCMGD-UHFFFAOYSA-N 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 abstract description 18
235000005152 nicotinamide Nutrition 0.000 abstract description 10
239000011570 nicotinamide Substances 0.000 abstract description 9
229960003966 nicotinamide Drugs 0.000 abstract description 9
241000233866 Fungi Species 0.000 abstract description 8
239000003921 oil Substances 0.000 description 19
235000019198 oils Nutrition 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 16
239000000243 solution Substances 0.000 description 14
241000196324 Embryophyta Species 0.000 description 13
239000002904 solvent Substances 0.000 description 13
239000002270 dispersing agent Substances 0.000 description 11
239000004094 surface-active agent Substances 0.000 description 11
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 10
239000007921 spray Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000004563 wettable powder Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000012230 colorless oil Substances 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
235000012239 silicon dioxide Nutrition 0.000 description 5
239000000126 substance Substances 0.000 description 5
241001149961 Alternaria brassicae Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000013543 active substance Substances 0.000 description 4
239000007900 aqueous suspension Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000969 carrier Substances 0.000 description 4
238000005286 illumination Methods 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
241000219198 Brassica Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241000209094 Oryza Species 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229920000847 nonoxynol Polymers 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000002689 soil Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
FQIUCPGDKPXSLL-UHFFFAOYSA-N 5-bromopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(Br)=C1 FQIUCPGDKPXSLL-UHFFFAOYSA-N 0.000 description 2
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
BMKOWBGBYPYXET-UHFFFAOYSA-N 5-chloropyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CN=CC(Cl)=C1 BMKOWBGBYPYXET-UHFFFAOYSA-N 0.000 description 2
241001450781 Bipolaris oryzae Species 0.000 description 2
235000011331 Brassica Nutrition 0.000 description 2
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UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 2
241000209140 Triticum Species 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
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WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
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OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
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ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
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239000003337 fertilizer Substances 0.000 description 2
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239000003701 inert diluent Substances 0.000 description 2
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235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
235000004977 Brassica sinapistrum Nutrition 0.000 description 1
239000004322 Butylated hydroxytoluene Substances 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
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BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
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LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
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150000001340 alkali metals Chemical class 0.000 description 1
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150000008052 alkyl sulfonates Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical class C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
229940095259 butylated hydroxytoluene Drugs 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
125000004803 chlorobenzyl group Chemical group 0.000 description 1
150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
230000006378 damage Effects 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical group ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
238000007865 diluting Methods 0.000 description 1
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
FXPVUWKFNGVHIZ-UHFFFAOYSA-L disodium;dodecyl sulfate Chemical compound [Na+].[Na+].CCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCOS([O-])(=O)=O FXPVUWKFNGVHIZ-UHFFFAOYSA-L 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
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239000003480 eluent Substances 0.000 description 1
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150000004665 fatty acids Chemical class 0.000 description 1
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238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 1
230000037406 food intake Effects 0.000 description 1
LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical class OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
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WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
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239000011630 iodine Substances 0.000 description 1
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QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
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239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000003801 milling Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003607 modifier Substances 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
150000005480 nicotinamides Chemical class 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
238000005554 pickling Methods 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000019423 pullulan Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
UPDATVKGFTVGQJ-UHFFFAOYSA-N sodium;azane Chemical class N.[Na+] UPDATVKGFTVGQJ-UHFFFAOYSA-N 0.000 description 1
AWLUSOLTCFEHNE-UHFFFAOYSA-N sodium;urea Chemical class [Na].NC(N)=O AWLUSOLTCFEHNE-UHFFFAOYSA-N 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000009736 wetting 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

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)
Pyridine Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CS861793A 1985-04-04 1986-03-15 Fungicide and process for preparing active compound CS253747B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH146885		1985-04-04
CH3886		1986-01-09

Publications (1)

Publication Number	Publication Date
CS253747B2 true CS253747B2 (en)	1987-12-17

Family

ID=25683325

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS861793A CS253747B2 (en)	1985-04-04	1986-03-15	Fungicide and process for preparing active compound

Country Status (7)

Country	Link
EP (1)	EP0198311A3 (da)
AU (1)	AU591106B2 (da)
CS (1)	CS253747B2 (da)
DK (1)	DK161702C (da)
HU (1)	HU195906B (da)
IL (1)	IL78303A0 (da)
NZ (1)	NZ215630A (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0301751B1 (en) *	1987-07-31	1993-03-10	Takeda Chemical Industries, Ltd.	Pyridinium derivatives, their production and use
JPH075442B2 (ja) *	1989-11-24	1995-01-25	三菱瓦斯化学株式会社	フェノキシアルキルアミン類および農園芸用殺菌剤
EP1275301A1 (en) *	2001-07-10	2003-01-15	Bayer CropScience S.A.	Trisubstituted heterocyclic compounds and their use as fungicides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4504484A (en) *	1982-11-04	1985-03-12	Chevron Research Company	Certain N,N-di-substituted-pyridine carboxamides, fungicidal compositions and fungicidal method of use
GB8403726D0 (en) *	1984-02-13	1984-03-14	Shell Int Research	Carboxamide derivatives

1986
- 1986-03-10 DK DK109586A patent/DK161702C/da not_active IP Right Cessation
- 1986-03-15 CS CS861793A patent/CS253747B2/cs unknown
- 1986-03-27 NZ NZ215630A patent/NZ215630A/xx unknown
- 1986-03-27 AU AU55333/86A patent/AU591106B2/en not_active Ceased
- 1986-03-28 IL IL78303A patent/IL78303A0/xx unknown
- 1986-04-01 EP EP86104415A patent/EP0198311A3/de not_active Ceased
- 1986-04-02 HU HU861347A patent/HU195906B/hu unknown

Also Published As

Publication number	Publication date
DK161702B (da)	1991-08-05
DK109586A (da)	1986-10-05
AU5533386A (en)	1986-10-09
AU591106B2 (en)	1989-11-30
DK109586D0 (da)	1986-03-10
HU195906B (en)	1988-08-29
DK161702C (da)	1992-01-13
EP0198311A2 (de)	1986-10-22
HUT42265A (en)	1987-07-28
EP0198311A3 (de)	1987-10-07
NZ215630A (en)	1988-07-28
IL78303A0 (en)	1986-07-31

Publication	Publication Date	Title
US5324854A (en)	1994-06-28	Intermediate isocyana to benzenesulfonamide compounds
JPH01305070A (ja)	1989-12-08	トリアジン除草剤
EP1101758A1 (en)	2001-05-23	Fused-heterocycle dicarboxylic diamide derivatives or salts thereof, herbicides and usage thereof
EP3389379A1 (en)	2018-10-24	Microbiocidal phenylamidine derivatives
BRPI0811354B1 (pt)	2017-04-04	composto, composição fungicida e método para controle de fungos patogênicos em culturas
CS223840B2 (en)	1983-11-25	Herbicide means and method of making the active substances
JPH01305082A (ja)	1989-12-08	トリ置換１，３，５―トリアジン―２，４，６―トリオン類
IL44710A (en)	1977-12-30	1-phenyl-2-azolyl-formamidines their preparation and their use as herbicides
PT1740544E (pt)	2007-11-06	Derivados de 2-piridinilcicloalquilcareoxamida úteis como fungicidas
PT87646B (pt)	1993-02-26	Processo para a preparacao duma composicao herbicida contendo triazolinonas substituidas, e de produtos intermediarios para a sua preparacao
JPS60181053A (ja)	1985-09-14	２‐シアノベンゾイミダゾールの新規誘導体、その製法及び殺菌剤としての使用
WO1991007392A1 (en)	1991-05-30	Pesticidal pyrimidinyl benzoic acids and esters
ES2911554T3 (es)	2022-05-19	Derivados de quinolina (tio)carboxamida microbiocidas
JPS6141353B2 (da)	1986-09-13
CN104725316B (zh)	2019-08-16	一类吡唑酰胺衍生物、其制备方法及应用
CS253747B2 (en)	1987-12-17	Fungicide and process for preparing active compound
JPS591481A (ja)	1984-01-06	異項環アミン類
EP0799825A1 (en)	1997-10-08	Pyridine-2,3-dicarboxylic acid diamide derivatives and herbicides comprising said derivatives as active ingredient
US4532251A (en)	1985-07-30	N-substituted-N',N'-disubstituted glycinamide fungicides
JPS61103873A (ja)	1986-05-22	新規な２‐シアノベンズイミダゾール誘導体
US4579853A (en)	1986-04-01	2-Cyano-imidazopyridine derivatives and their use as fungicides
WO2015040352A1 (en)	2015-03-26	Agricultural chemicals
WO2014036952A1 (zh)	2014-03-13	哒嗪酮类化合物及其用途
JPS60214785A (ja)	1985-10-28	ピラゾ−ルスルホニルウレア誘導体、および植物生長調節剤または除草剤
CN115427415A (zh)	2022-12-02	用作农业化学品的吡啶并[2,3-e]恶嗪衍生物