CA1082190A - Derives de la pyridazinone - Google Patents

Derives de la pyridazinone

Info

Publication number: CA1082190A
Authority: CA; Canada
Prior art keywords: pyridazinone; group; compound; formula; dichloro
Prior art date: 1975-09-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA339,824A

Other languages

English (en)

Inventor

Teruomi Jojima

Yukiyoshi Takahi

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

Sankyo Co Ltd

Original Assignee

Sankyo Co Ltd

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.)

1975-09-11

Filing date

1979-11-14

Publication date

1980-07-22

1975-09-11 Priority claimed from JP11033175A external-priority patent/JPS5234928A/ja

1976-04-01 Priority claimed from JP51036453A external-priority patent/JPS584681B2/ja

1976-09-13 Priority claimed from CA261,039A external-priority patent/CA1082105A/fr

1979-11-14 Application filed by Sankyo Co Ltd filed Critical Sankyo Co Ltd

1979-11-14 Priority to CA339,824A priority Critical patent/CA1082190A/fr

1980-07-22 Application granted granted Critical

1980-07-22 Publication of CA1082190A publication Critical patent/CA1082190A/fr

Status Expired legal-status Critical Current

Links

AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 26
125000005843 halogen group Chemical group 0.000 claims abstract description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
150000001875 compounds Chemical class 0.000 claims description 190
238000006243 chemical reaction Methods 0.000 claims description 65
238000000034 method Methods 0.000 claims description 47
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 35
239000002253 acid Substances 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 19
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 13
239000000047 product Substances 0.000 claims description 13
125000003302 alkenyloxy group Chemical group 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
230000002140 halogenating effect Effects 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000005133 alkynyloxy group Chemical group 0.000 claims description 9
239000002841 Lewis acid Substances 0.000 claims description 8
230000026030 halogenation Effects 0.000 claims description 8
238000005658 halogenation reaction Methods 0.000 claims description 8
150000007517 lewis acids Chemical class 0.000 claims description 8
KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical class OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-UHFFFAOYSA-N 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
UWQMKVBQKFHLCE-UHFFFAOYSA-N diclomezine Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NNC(=O)C=C1 UWQMKVBQKFHLCE-UHFFFAOYSA-N 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
229940014800 succinic anhydride Drugs 0.000 claims description 6
ZKYIDRUAEBYCQQ-UHFFFAOYSA-N 3-(3,5-dichloro-4-methoxyphenyl)-1h-pyridazin-6-one Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1C1=NNC(=O)C=C1 ZKYIDRUAEBYCQQ-UHFFFAOYSA-N 0.000 claims description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
QOKDCOAWIMPZEZ-UHFFFAOYSA-N 3-(3,5-dichloro-4-ethylphenyl)-1h-pyridazin-6-one Chemical compound C1=C(Cl)C(CC)=C(Cl)C=C1C1=NNC(=O)C=C1 QOKDCOAWIMPZEZ-UHFFFAOYSA-N 0.000 claims description 4
230000002152 alkylating effect Effects 0.000 claims description 4
238000005947 deacylation reaction Methods 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
DHSHYQFVUQVPFO-UHFFFAOYSA-N 3-(3,5-dibromo-4-methylphenyl)-1h-pyridazin-6-one Chemical compound C1=C(Br)C(C)=C(Br)C=C1C1=NNC(=O)C=C1 DHSHYQFVUQVPFO-UHFFFAOYSA-N 0.000 claims description 3
DMLMHZNXEDVHDN-UHFFFAOYSA-N 3-(3,5-dichloro-4-methoxyphenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1C1=NNC(=O)CC1 DMLMHZNXEDVHDN-UHFFFAOYSA-N 0.000 claims description 3
MMBKLLHNCNSRBB-UHFFFAOYSA-N 3-(3-bromo-5-chloro-2-hydroxy-4-methylphenyl)-1H-pyridazin-6-one Chemical compound OC1=C(Br)C(C)=C(Cl)C=C1C1=NNC(=O)C=C1 MMBKLLHNCNSRBB-UHFFFAOYSA-N 0.000 claims description 3
BMMQDXFSGTYZPE-UHFFFAOYSA-N 3-(3-bromophenyl)-1h-pyridazin-6-one Chemical compound BrC1=CC=CC(C2=NNC(=O)C=C2)=C1 BMMQDXFSGTYZPE-UHFFFAOYSA-N 0.000 claims description 3
SLKWFBNPKSFHQA-UHFFFAOYSA-N 3-(3-bromophenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound BrC1=CC=CC(C=2CCC(=O)NN=2)=C1 SLKWFBNPKSFHQA-UHFFFAOYSA-N 0.000 claims description 3
LYOLSCRSCLCBCB-UHFFFAOYSA-N 3-(3-chloro-4-methylphenyl)-1h-pyridazin-6-one Chemical compound C1=C(Cl)C(C)=CC=C1C1=NNC(=O)C=C1 LYOLSCRSCLCBCB-UHFFFAOYSA-N 0.000 claims description 3
XNZWDOGDTAAYTL-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylphenyl)-1h-pyridazin-6-one Chemical compound C1=C(Cl)C(C(C)C)=CC=C1C1=NNC(=O)C=C1 XNZWDOGDTAAYTL-UHFFFAOYSA-N 0.000 claims description 3
YRWWFLYKKZTALE-UHFFFAOYSA-N 3-(3-chlorophenyl)-1h-pyridazin-6-one Chemical compound ClC1=CC=CC(C2=NNC(=O)C=C2)=C1 YRWWFLYKKZTALE-UHFFFAOYSA-N 0.000 claims description 3
QKRYJHJJRHOMAY-UHFFFAOYSA-N 3-(4-amino-3,5-dibromophenyl)-1h-pyridazin-6-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C1=NNC(=O)C=C1 QKRYJHJJRHOMAY-UHFFFAOYSA-N 0.000 claims description 3
230000020176 deacylation Effects 0.000 claims description 3
AEIYVDFPUAZQIZ-UHFFFAOYSA-N 3-(3,5-dibromo-2-hydroxy-4-methylphenyl)-1H-pyridazin-6-one Chemical compound OC1=C(Br)C(C)=C(Br)C=C1C1=NNC(=O)C=C1 AEIYVDFPUAZQIZ-UHFFFAOYSA-N 0.000 claims description 2
YJUMXHGWHYNVBJ-UHFFFAOYSA-N 3-(3,5-dibromo-4-chloro-2-hydroxyphenyl)-1H-pyridazin-6-one Chemical compound OC1=C(Br)C(Cl)=C(Br)C=C1C1=NNC(=O)C=C1 YJUMXHGWHYNVBJ-UHFFFAOYSA-N 0.000 claims description 2
RVAWLAAPWSOPGW-UHFFFAOYSA-N 3-(3,5-dichloro-4-methylphenyl)-1h-pyridazin-6-one;methylimino(oxo)methane Chemical compound CN=C=O.C1=C(Cl)C(C)=C(Cl)C=C1C1=NNC(=O)C=C1 RVAWLAAPWSOPGW-UHFFFAOYSA-N 0.000 claims description 2
WBCNIMUXUHZPGC-UHFFFAOYSA-N 3-(3-bromo-4-methylphenyl)-1h-pyridazin-6-one Chemical compound C1=C(Br)C(C)=CC=C1C1=NNC(=O)C=C1 WBCNIMUXUHZPGC-UHFFFAOYSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 2
239000007795 chemical reaction product Substances 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
-1 6-(substituted phenyl)-3(2H)-pyridazinones Chemical class 0.000 abstract description 59
239000000417 fungicide Substances 0.000 abstract description 18
239000000203 mixture Substances 0.000 description 86
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
239000002904 solvent Substances 0.000 description 39
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
238000002360 preparation method Methods 0.000 description 30
230000000855 fungicidal effect Effects 0.000 description 26
159000000007 calcium salts Chemical class 0.000 description 20
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 18
241000196324 Embryophyta Species 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
238000001914 filtration Methods 0.000 description 16
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
240000007594 Oryza sativa Species 0.000 description 14
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
239000004009 herbicide Substances 0.000 description 14
239000000243 solution Substances 0.000 description 14
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
229910052794 bromium Inorganic materials 0.000 description 13
238000010992 reflux Methods 0.000 description 13
238000003756 stirring Methods 0.000 description 13
239000000126 substance Substances 0.000 description 13
239000000725 suspension Substances 0.000 description 13
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000000460 chlorine Substances 0.000 description 12
239000013078 crystal Substances 0.000 description 12
239000007787 solid Substances 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
238000010438 heat treatment Methods 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
239000012442 inert solvent Substances 0.000 description 9
159000000000 sodium salts Chemical class 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 8
244000053095 fungal pathogen Species 0.000 description 8
235000011167 hydrochloric acid Nutrition 0.000 description 8
229960000443 hydrochloric acid Drugs 0.000 description 8
239000002689 soil Substances 0.000 description 8
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 7
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
238000000354 decomposition reaction Methods 0.000 description 7
201000010099 disease Diseases 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
150000002576 ketones Chemical class 0.000 description 7
235000019260 propionic acid Nutrition 0.000 description 7
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 6
239000008187 granular material Substances 0.000 description 6
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
PUWMHJMSNXPBBW-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1h-pyridazin-6-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=NNC(=O)C=C1 PUWMHJMSNXPBBW-UHFFFAOYSA-N 0.000 description 5
FORXLTRVIAYGFA-UHFFFAOYSA-N 3-(3,5-dichloro-4-hydroxyphenyl)-4,5-dihydro-1H-pyridazin-6-one Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1C1=NNC(=O)CC1 FORXLTRVIAYGFA-UHFFFAOYSA-N 0.000 description 5
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 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
239000011737 fluorine Chemical group 0.000 description 5
239000002917 insecticide Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
QKDLXQWEBIYZSS-UHFFFAOYSA-N 4-(4-hydroxyphenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(O)C=C1 QKDLXQWEBIYZSS-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
235000007164 Oryza sativa Nutrition 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
238000006356 dehydrogenation reaction Methods 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
235000009566 rice Nutrition 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 3
XTYGQBBNQLEZAG-UHFFFAOYSA-N 3-(4-amino-3-bromophenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=C(Br)C(N)=CC=C1C1=NNC(=O)CC1 XTYGQBBNQLEZAG-UHFFFAOYSA-N 0.000 description 3
CMEKQKBAEVBMSD-UHFFFAOYSA-N 3-(4-amino-3-chlorophenyl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=C(Cl)C(N)=CC=C1C1=NNC(=O)CC1 CMEKQKBAEVBMSD-UHFFFAOYSA-N 0.000 description 3
HCWQWCWXNRPILJ-UHFFFAOYSA-N 4-(4-acetamido-3-chlorophenyl)-4-oxobutanoic acid Chemical compound CC(=O)NC1=CC=C(C(=O)CCC(O)=O)C=C1Cl HCWQWCWXNRPILJ-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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229910017604 nitric acid Inorganic materials 0.000 description 1
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239000012053 oil suspension Substances 0.000 description 1
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VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
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239000002798 polar solvent Substances 0.000 description 1
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229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
QDESFMLRHRZCSV-UHFFFAOYSA-M potassium;n-(hydroxymethyl)-n-methylcarbamodithioate Chemical compound [K+].OCN(C)C([S-])=S QDESFMLRHRZCSV-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 1
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000008262 pumice Substances 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
125000005920 sec-butoxy group Chemical group 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 1
JMSBNRZOKMBJFE-UHFFFAOYSA-M sodium;2,3-didecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCC1=CC=CC(S([O-])(=O)=O)=C1CCCCCCCCCC JMSBNRZOKMBJFE-UHFFFAOYSA-M 0.000 description 1
IXYACKYHUWCLAM-UHFFFAOYSA-M sodium;2-ethylhex-1-ene-1-sulfonate Chemical compound [Na+].CCCCC(CC)=CS([O-])(=O)=O IXYACKYHUWCLAM-UHFFFAOYSA-M 0.000 description 1
AZXQLMRILCCVDW-UHFFFAOYSA-M sodium;5-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(C(C)C)=CC=CC2=C1S([O-])(=O)=O AZXQLMRILCCVDW-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000004455 soybean meal 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
229940037312 stearamide Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

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Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA339,824A 1975-09-11 1979-11-14 Derives de la pyridazinone Expired CA1082190A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA339,824A CA1082190A (fr)	1975-09-11	1979-11-14	Derives de la pyridazinone

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP110331/75		1975-09-11
JP11033175A JPS5234928A (en)	1975-09-11	1975-09-11	Fungicides for agriculture and gardening use
JP51036453A JPS584681B2 (ja)	1976-04-01	1976-04-01	農園芸用殺菌剤
JP36453/76		1976-04-01
CA261,039A CA1082105A (fr)	1975-09-11	1976-09-13	Derive de pyridazinone; emploi comme fongicides pour les plantes cultivees
CA339,824A CA1082190A (fr)	1975-09-11	1979-11-14	Derives de la pyridazinone

Publications (1)

Publication Number	Publication Date
CA1082190A true CA1082190A (fr)	1980-07-22

Family

ID=27425940

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA339,824A Expired CA1082190A (fr)	1975-09-11	1979-11-14	Derives de la pyridazinone

Country Status (1)

Country	Link
CA (1)	CA1082190A (fr)

1979
- 1979-11-14 CA CA339,824A patent/CA1082190A/fr not_active Expired

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Date	Code	Title	Description
1997-07-22	MKEX	Expiry

Publication	Publication Date	Title
US4052395A (en)	1977-10-04	Agricultural fungicidal compositions containing 6-(substituted phenyl)-pyridazinones and said pyridazinones
EP0023785B1 (fr)	1985-04-03	Dérivés de l'acide quinoxalinyloxyphénoxyalcoyle carboxyliques, leur préparation et leur utilisation comme herbicides
US4279908A (en)	1981-07-21	Pyridazine derivatives and their use as agricultural fungicides
US4314065A (en)	1982-02-02	Phenylamine substituted on amine with a benzo(oxa, thia or di) azole group
PL172588B1 (pl)	1997-10-31	2-[(4-Heterocykliczno-podstawiony-3-chlorowcofenoksymetylo)fenoksy]alkanian PL PL PL PL PL PL PL
EP0072238B1 (fr)	1985-11-06	Dérivés de pyridazinone, leur préparation et leur utilisation dans des compositions pour l'agriculture et le traitement des graines et des plantes
EP0024932A2 (fr)	1981-03-11	Dérivés d'acides carboxyliques de 1,2,4-benzotriazinyloxyphénoxyalcane, procédés pour leur préparation, leur utilisation comme herbicides et leur préparation
CA1082190A (fr)	1980-07-22	Derives de la pyridazinone
US5462914A (en)	1995-10-31	Herbicidal n-cyanopyridazinones
US5298480A (en)	1994-03-29	Herbicidal sulfonylurea derivatives
CS228911B2 (en)	1984-05-14	Herbicide and method of preparing active substances thereof
EP0089650B1 (fr)	1986-12-30	Procédé de production de dérivés de pyridazinone antifongiques et certains composés nouveaux produits par un tel procédé
EP0248554B1 (fr)	1993-02-03	Composés hétérocycliques
EP0063418A1 (fr)	1982-10-27	Dérivés des acides indanyloxy- et tétralinyloxy-phénoxy-propioniques, leur procédé de préparation, procédés herbicides et compositions herbicides les utilisant
JPS6022681B2 (ja)	1985-06-03	農園芸用殺菌剤
EP0024931B1 (fr)	1984-10-17	Dérivés d'acides carboxyliques de 1,2,4-benzotriazinylaminophénoxy alcane, procédés pour leur préparation et leur utilisation comme herbicides
JPS584681B2 (ja)	1983-01-27	農園芸用殺菌剤
CA1288434C (fr)	1991-09-03	Compositions herbicides
US3758481A (en)	1973-09-11	Ridine m-(2,4-dichloro - 5-(haloalkoxy)-phenylcarbomoyl)-pyrrolidine or pipe
CA1092116A (fr)	1980-12-23	Pyrazolo-triazinediones
JPS6030645B2 (ja)	1985-07-17	選択的除草剤およびその製法
US4255181A (en)	1981-03-10	Use of substituted-3-phenacylidenephthalides as corn plant growth regulants
JPS60149571A (ja)	1985-08-07	２−（置換フエニル）−１，２，４−トリアゾリン−３−オン類およびこれを有効成分とする除草剤
JPH0428701B2 (fr)	1992-05-15
JPS6140275A (ja)	1986-02-26	アミノトリアジノン誘導体の製造方法、新規なアミノトリアジノン誘導体及び該化合物を含有する組成物