SK286264B6 - Derivát pyrimidinylbenzimidazolu alebo triazinylbenzimidazolu, medziprodukty na jeho prípravu a poľnohospodársky/záhradnícky fungicíd s jeho obsahom - Google Patents

Derivát pyrimidinylbenzimidazolu alebo triazinylbenzimidazolu, medziprodukty na jeho prípravu a poľnohospodársky/záhradnícky fungicíd s jeho obsahom Download PDF

Info

Publication number: SK286264B6
Authority: SK; Slovakia
Prior art keywords: ome; alkoxy; alkyl; group; oet
Prior art date: 1998-11-17

Application number

SK615-2001A

Other languages

English (en)

Slovak (sk)

Other versions

SK6152001A3 (en

Inventor

Masaru Shibata

Kiyoshi Kawai

Takechi Makihara

Norihisa Yonekura

Takahiro Kawashima

Junetsu Sakai

Norimichi Muramatsu

Original Assignee

Kumiai Chemical Industry Co., Ltd.

Ihara Chemical Industry 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.)

1998-11-17

Filing date

1999-11-15

Publication date

2008-06-06

1999-11-15 Application filed by Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd. filed Critical Kumiai Chemical Industry Co., Ltd.

2001-12-03 Publication of SK6152001A3 publication Critical patent/SK6152001A3/sk

2008-06-06 Publication of SK286264B6 publication Critical patent/SK286264B6/sk

Links

239000000417 fungicide Substances 0.000 title claims abstract description 19
WTZRQYJHRXQWTK-UHFFFAOYSA-N 2-pyrimidin-2-yl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C1=NC=CC=N1 WTZRQYJHRXQWTK-UHFFFAOYSA-N 0.000 title claims abstract description 14
239000000543 intermediate Substances 0.000 title abstract description 5
239000004480 active ingredient Substances 0.000 claims abstract description 8
230000000855 fungicidal effect Effects 0.000 claims abstract description 6
239000000460 chlorine Substances 0.000 claims description 137
125000003545 alkoxy group Chemical group 0.000 claims description 104
125000000217 alkyl group Chemical group 0.000 claims description 91
-1 triazin-2-yl Chemical group 0.000 claims description 74
150000001875 compounds Chemical class 0.000 claims description 64
125000004093 cyano group Chemical group *C#N 0.000 claims description 47
229910052736 halogen Inorganic materials 0.000 claims description 44
150000002367 halogens Chemical group 0.000 claims description 42
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 42
125000003282 alkyl amino group Chemical group 0.000 claims description 34
125000005843 halogen group Chemical group 0.000 claims description 25
125000003302 alkenyloxy group Chemical group 0.000 claims description 23
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 23
125000004414 alkyl thio group Chemical group 0.000 claims description 21
125000001188 haloalkyl group Chemical group 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 20
125000004438 haloalkoxy group Chemical group 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 20
125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 19
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 11
150000002431 hydrogen Chemical group 0.000 claims description 11
125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
RSAWQCDTJIQFAD-UHFFFAOYSA-N 4-chloro-1-n-(4,6-dimethoxy-1,3,5-triazin-2-yl)benzene-1,2-diamine Chemical compound COC1=NC(OC)=NC(NC=2C(=CC(Cl)=CC=2)N)=N1 RSAWQCDTJIQFAD-UHFFFAOYSA-N 0.000 claims description 3
125000005133 alkynyloxy group Chemical group 0.000 claims description 3
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
WGLYXMYIFDWZPR-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetraethyl-6-n-(2-nitrophenyl)-1,3,5-triazine-2,4,6-triamine Chemical compound CCN(CC)C1=NC(N(CC)CC)=NC(NC=2C(=CC=CC=2)[N+]([O-])=O)=N1 WGLYXMYIFDWZPR-UHFFFAOYSA-N 0.000 claims description 2
WUNIETPQNJGKFG-UHFFFAOYSA-N 4,6-dichloro-n-(2-nitrophenyl)-1,3,5-triazin-2-amine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 WUNIETPQNJGKFG-UHFFFAOYSA-N 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
LWPUUSTXVSSVLQ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetraethyl-6-n-(4-methyl-2-nitrophenyl)-1,3,5-triazine-2,4,6-triamine Chemical compound CCN(CC)C1=NC(N(CC)CC)=NC(NC=2C(=CC(C)=CC=2)[N+]([O-])=O)=N1 LWPUUSTXVSSVLQ-UHFFFAOYSA-N 0.000 claims 1
JNHNYVGHUQDYLS-UHFFFAOYSA-N 4,6-dichloro-n-(4-methoxy-2-nitrophenyl)-1,3,5-triazin-2-amine Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 JNHNYVGHUQDYLS-UHFFFAOYSA-N 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2332
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
210000000941 bile Anatomy 0.000 description 45
238000006243 chemical reaction Methods 0.000 description 39
239000000047 product Substances 0.000 description 30
239000002904 solvent Substances 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
239000000843 powder Substances 0.000 description 20
238000000034 method Methods 0.000 description 18
239000000203 mixture Substances 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
229920000728 polyester Polymers 0.000 description 12
238000001914 filtration Methods 0.000 description 11
238000009472 formulation Methods 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
238000009835 boiling Methods 0.000 description 10
239000013078 crystal Substances 0.000 description 10
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 10
239000000243 solution Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
201000010099 disease Diseases 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
238000001035 drying Methods 0.000 description 9
238000000605 extraction Methods 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
238000005406 washing Methods 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
238000007796 conventional method Methods 0.000 description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
150000003931 anilides Chemical class 0.000 description 6
230000004071 biological effect Effects 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
239000000428 dust Substances 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000004563 wettable powder Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
230000001804 emulsifying effect Effects 0.000 description 4
239000005457 ice water Substances 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
241000209140 Triticum Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000004927 clay Substances 0.000 description 3
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
210000003746 feather Anatomy 0.000 description 3
239000007788 liquid Substances 0.000 description 3
CLBDFJIIPMNCSN-UHFFFAOYSA-N n-(4-chloro-2-nitrophenyl)-4,6-dimethoxy-1,3,5-triazin-2-amine Chemical compound COC1=NC(OC)=NC(NC=2C(=CC(Cl)=CC=2)[N+]([O-])=O)=N1 CLBDFJIIPMNCSN-UHFFFAOYSA-N 0.000 description 3
NGCURIJPLVFJJH-UHFFFAOYSA-N n-phenyltriazin-4-amine Chemical class C=1C=NN=NC=1NC1=CC=CC=C1 NGCURIJPLVFJJH-UHFFFAOYSA-N 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
YJUUZFWMKJBVFJ-UHFFFAOYSA-N 1,3-dimethylimidazolidin-4-one Chemical compound CN1CN(C)C(=O)C1 YJUUZFWMKJBVFJ-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
MWPVZJJSQQLFEB-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-2-methoxybenzimidazole Chemical compound COC1=NC2=CC=CC=C2N1C1=NC(OC)=CC(OC)=N1 MWPVZJJSQQLFEB-UHFFFAOYSA-N 0.000 description 2
IXVYXVXZJJCRFU-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-5-methylbenzimidazol-2-amine Chemical compound COC1=CC(OC)=NC(N2C3=CC=C(C)C=C3N=C2N)=N1 IXVYXVXZJJCRFU-UHFFFAOYSA-N 0.000 description 2
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
UZLVRGBLDHUIDD-UHFFFAOYSA-N 2-n-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylbenzene-1,2-diamine Chemical compound COC1=NC(OC)=NC(NC=2C(=CC=C(C)C=2)N)=N1 UZLVRGBLDHUIDD-UHFFFAOYSA-N 0.000 description 2
BTRNEFRKPPZRQA-UHFFFAOYSA-N 2-n-(4,6-dimethoxypyrimidin-2-yl)-4-methylbenzene-1,2-diamine Chemical compound COC1=CC(OC)=NC(NC=2C(=CC=C(C)C=2)N)=N1 BTRNEFRKPPZRQA-UHFFFAOYSA-N 0.000 description 2
ITDVJJVNAASTRS-UHFFFAOYSA-N 4,6-dimethoxy-2-methylsulfonylpyrimidine Chemical compound COC1=CC(OC)=NC(S(C)(=O)=O)=N1 ITDVJJVNAASTRS-UHFFFAOYSA-N 0.000 description 2
KXMOBKHNXKAUJD-UHFFFAOYSA-N 4,6-dimethoxy-n-(4-methyl-2-nitrophenyl)-1,3,5-triazin-2-amine Chemical compound COC1=NC(OC)=NC(NC=2C(=CC(C)=CC=2)[N+]([O-])=O)=N1 KXMOBKHNXKAUJD-UHFFFAOYSA-N 0.000 description 2
ZWVBPETWMMFNQP-UHFFFAOYSA-N 4,6-dimethoxy-n-(4-methyl-2-nitrophenyl)pyrimidin-2-amine Chemical compound COC1=CC(OC)=NC(NC=2C(=CC(C)=CC=2)[N+]([O-])=O)=N1 ZWVBPETWMMFNQP-UHFFFAOYSA-N 0.000 description 2
MGMBUMDYIHNZKO-UHFFFAOYSA-N 5-chloro-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-2-methylbenzimidazole Chemical compound COC1=NC(OC)=NC(N2C3=CC=C(Cl)C=C3N=C2C)=N1 MGMBUMDYIHNZKO-UHFFFAOYSA-N 0.000 description 2
WFFZSUIFSVKWHZ-UHFFFAOYSA-N 5-chloro-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)benzimidazol-2-amine Chemical compound COC1=NC(OC)=NC(N2C3=CC=C(Cl)C=C3N=C2N)=N1 WFFZSUIFSVKWHZ-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
240000008067 Cucumis sativus Species 0.000 description 2
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
241000233866 Fungi Species 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
241001361634 Rhizoctonia Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
241000317942 Venturia <ichneumonid wasp> Species 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000008059 anilinopyrimidines Chemical class 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
150000001556 benzimidazoles Chemical class 0.000 description 2
FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
235000011116 calcium hydroxide Nutrition 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000012295 chemical reaction liquid Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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125000006137 n-hexyl sulfonyl group Chemical group 0.000 description 1
125000004718 n-hexylthio group Chemical group C(CCCCC)S* 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
125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 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
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000004576 sand Substances 0.000 description 1
208000005687 scabies Diseases 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
125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000004753 textile Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK615-2001A 1998-11-17 1999-11-15 Derivát pyrimidinylbenzimidazolu alebo triazinylbenzimidazolu, medziprodukty na jeho prípravu a poľnohospodársky/záhradnícky fungicíd s jeho obsahom SK286264B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP34361498		1998-11-17
JP3956699		1999-02-18
PCT/JP1999/006364 WO2000029404A1 (fr)	1998-11-17	1999-11-15	Derives de pyrimidinylbenzimidazole et de triazinylbenzimidazole et bactericides agricoles/horticoles

Publications (2)

Publication Number	Publication Date
SK6152001A3 SK6152001A3 (en)	2001-12-03
SK286264B6 true SK286264B6 (sk)	2008-06-06

Family

ID=26378972

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK615-2001A SK286264B6 (sk)	1998-11-17	1999-11-15	Derivát pyrimidinylbenzimidazolu alebo triazinylbenzimidazolu, medziprodukty na jeho prípravu a poľnohospodársky/záhradnícky fungicíd s jeho obsahom

Country Status (18)

Country	Link
US (2)	US6576631B1 (xx)
EP (1)	EP1132387B1 (xx)
KR (1)	KR100631307B1 (xx)
CN (1)	CN1243002C (xx)
AT (1)	ATE305465T1 (xx)
AU (1)	AU755538B2 (xx)
BR (1)	BR9915401B1 (xx)
CA (1)	CA2350968C (xx)
CZ (1)	CZ20011466A3 (xx)
DE (1)	DE69927516T2 (xx)
HU (1)	HUP0104171A3 (xx)
IL (2)	IL143157A0 (xx)
NZ (1)	NZ511311A (xx)
PL (1)	PL194045B1 (xx)
RU (1)	RU2222536C2 (xx)
SK (1)	SK286264B6 (xx)
TR (1)	TR200101381T2 (xx)
WO (1)	WO2000029404A1 (xx)

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BRPI1010096A2 (pt)	2009-06-18	2016-03-15	Basf Se	compostos de formulas i e ii, composição agrícola, uso de um composto, método de controle de fungos nocivos, semente, composição farmacêutica, uso de um composto e método de tratamento contra o câncer ou infecções por vírus ou para combater a fungos zoopatogênicos ou humanopatogênicos
PE20120625A1 (es)	2009-06-18	2012-05-20	Basf Se	Mezclas fungicidas
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WO2011069894A1 (de)	2009-12-08	2011-06-16	Basf Se	Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel
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EP2402339A1 (en)	2010-06-29	2012-01-04	Basf Se	Pyrazolopyridine compounds
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EP2402344A1 (en)	2010-06-29	2012-01-04	Basf Se	Pyrazole fused bicyclic compounds
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EP2402345A1 (en)	2010-06-29	2012-01-04	Basf Se	Pyrazole fused bicyclic compounds
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AU1180500A (en)	2000-06-05
US20040023966A1 (en)	2004-02-05
PL347688A1 (en)	2002-04-22
AU755538B2 (en)	2002-12-12
HUP0104171A2 (hu)	2002-02-28
CZ20011466A3 (cs)	2001-09-12
CN1243002C (zh)	2006-02-22
RU2222536C2 (ru)	2004-01-27
US6872729B2 (en)	2005-03-29
US6576631B1 (en)	2003-06-10
CA2350968C (en)	2008-10-28
BR9915401B1 (pt)	2011-04-19
EP1132387A4 (en)	2002-06-05
EP1132387B1 (en)	2005-09-28
SK6152001A3 (en)	2001-12-03
DE69927516D1 (de)	2006-02-09
CA2350968A1 (en)	2000-05-25
TR200101381T2 (tr)	2002-05-21
IL143157A0 (en)	2002-04-21
KR20010080976A (ko)	2001-08-25
IL143157A (en)	2010-11-30
CN1333768A (zh)	2002-01-30
WO2000029404A1 (fr)	2000-05-25
KR100631307B1 (ko)	2006-10-04
PL194045B1 (pl)	2007-04-30
WO2000029404A8 (fr)	2000-09-08
ATE305465T1 (de)	2005-10-15
DE69927516T2 (de)	2006-03-16
BR9915401A (pt)	2001-08-14
EP1132387A1 (en)	2001-09-12
NZ511311A (en)	2002-10-25
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