SK33596A3 - 2-(4-alkylthiopyrimidine-5-yl)acetic acid derivative, preparing method thereof and fungicidal agents containing them - Google Patents

2-(4-alkylthiopyrimidine-5-yl)acetic acid derivative, preparing method thereof and fungicidal agents containing them Download PDF

Info

Publication number: SK33596A3
Authority: SK; Slovakia
Prior art keywords: methyl; phenyl; alkyl; formula; carbon atoms
Prior art date: 1995-03-10

Application number

SK335-96A

Other languages

English (en)

Slovak (sk)

Inventor

Gerald Wayne Craig

Martin Eberle

Fritz Schaub

Original Assignee

Sandoz Ag

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.)

1995-03-10

Filing date

1996-03-08

Publication date

1997-03-05

1996-03-08 Application filed by Sandoz Ag filed Critical Sandoz Ag

1997-03-05 Publication of SK33596A3 publication Critical patent/SK33596A3/sk

Links

238000000034 method Methods 0.000 title claims description 12
150000001242 acetic acid derivatives Chemical class 0.000 title claims description 3
239000000417 fungicide Substances 0.000 title description 4
-1 C1-4alkoxycarbonyl Chemical group 0.000 claims abstract description 276
150000001875 compounds Chemical class 0.000 claims abstract description 97
239000000203 mixture Substances 0.000 claims abstract description 39
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 15
125000003118 aryl group Chemical group 0.000 claims abstract description 15
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
239000001257 hydrogen Substances 0.000 claims abstract description 15
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 12
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
239000001301 oxygen Substances 0.000 claims abstract description 6
239000011593 sulfur Substances 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
125000004104 aryloxy group Chemical group 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
125000005553 heteroaryloxy group Chemical group 0.000 claims abstract description 4
238000002360 preparation method Methods 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
125000004432 carbon atom Chemical group C* 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 30
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 8
241000233866 Fungi Species 0.000 claims description 7
230000000855 fungicidal effect Effects 0.000 claims description 6
125000003226 pyrazolyl group Chemical group 0.000 claims description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
125000005605 benzo 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
125000000842 isoxazolyl group Chemical group 0.000 claims description 3
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000005347 halocycloalkyl group Chemical group 0.000 claims description 2
230000003032 phytopathogenic effect Effects 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 abstract description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 6
229910052757 nitrogen Inorganic materials 0.000 abstract description 6
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 21
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
241000196324 Embryophyta Species 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000002904 solvent Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
239000002585 base Substances 0.000 description 15
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 14
238000001704 evaporation Methods 0.000 description 14
239000004480 active ingredient Substances 0.000 description 13
230000008020 evaporation Effects 0.000 description 13
239000012074 organic phase Substances 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 11
239000012442 inert solvent Substances 0.000 description 11
150000003254 radicals Chemical class 0.000 description 11
241000209140 Triticum Species 0.000 description 10
235000021307 Triticum Nutrition 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
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 9
238000007069 methylation reaction Methods 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
240000005979 Hordeum vulgare Species 0.000 description 7
235000007340 Hordeum vulgare Nutrition 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
210000000941 bile Anatomy 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 6
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
244000052769 pathogen Species 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
238000003756 stirring Methods 0.000 description 6
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 5
125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 5
235000011430 Malus pumila Nutrition 0.000 description 5
244000070406 Malus silvestris Species 0.000 description 5
235000015103 Malus silvestris Nutrition 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
230000011987 methylation Effects 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
239000002689 soil Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 4
240000008067 Cucumis sativus Species 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241000228456 Leptosphaeria Species 0.000 description 4
244000046052 Phaseolus vulgaris Species 0.000 description 4
241000228453 Pyrenophora Species 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
240000003768 Solanum lycopersicum Species 0.000 description 4
229910000102 alkali metal hydride Inorganic materials 0.000 description 4
150000008046 alkali metal hydrides Chemical class 0.000 description 4
238000003556 assay Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
241000317981 Podosphaera fuliginea Species 0.000 description 3
241000228454 Pyrenophora graminea Species 0.000 description 3
241000221577 Uromyces appendiculatus Species 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000003513 alkali Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
150000005840 aryl radicals Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
230000002538 fungal effect Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 3
239000012414 tert-butyl nitrite Substances 0.000 description 3
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
241001480061 Blumeria graminis Species 0.000 description 2
238000003512 Claisen condensation reaction Methods 0.000 description 2
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
241000510928 Erysiphe necator Species 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000233622 Phytophthora infestans Species 0.000 description 2
241001337928 Podosphaera leucotricha Species 0.000 description 2
241001246061 Puccinia triticina Species 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
241000228452 Venturia inaequalis Species 0.000 description 2
240000006365 Vitis vinifera Species 0.000 description 2
235000014787 Vitis vinifera Nutrition 0.000 description 2
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000005159 cyanoalkoxy group Chemical group 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
235000013399 edible fruits Nutrition 0.000 description 2
238000009472 formulation Methods 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
125000005326 heteroaryloxy alkyl group Chemical group 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
MFPSZNNTVOZIMK-UHFFFAOYSA-N methyl 2-(4-chloro-2-methyl-6-methylsulfanylpyrimidin-5-yl)acetate Chemical compound COC(=O)CC1=C(Cl)N=C(C)N=C1SC MFPSZNNTVOZIMK-UHFFFAOYSA-N 0.000 description 2
ZXWGTNBLBKTYQV-UHFFFAOYSA-N methyl 2-[2-methyl-4-methylsulfanyl-6-[3-(trifluoromethyl)phenoxy]pyrimidin-5-yl]acetate Chemical compound N1=C(C)N=C(SC)C(CC(=O)OC)=C1OC1=CC=CC(C(F)(F)F)=C1 ZXWGTNBLBKTYQV-UHFFFAOYSA-N 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
230000001035 methylating effect Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000005507 spraying Methods 0.000 description 2
235000013311 vegetables Nutrition 0.000 description 2
238000010792 warming Methods 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 description 1
RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 1
PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
125000005976 1-phenylethyloxy group Chemical group 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
PTMRDOLOEDPHLB-UHFFFAOYSA-N 2,3-dipentylphenol Chemical compound CCCCCC1=CC=CC(O)=C1CCCCC PTMRDOLOEDPHLB-UHFFFAOYSA-N 0.000 description 1
STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 1
HGMPQHSQYMZZNT-UHFFFAOYSA-N 2-(3-hydroxyphenoxy)benzonitrile Chemical compound OC1=CC=CC(OC=2C(=CC=CC=2)C#N)=C1 HGMPQHSQYMZZNT-UHFFFAOYSA-N 0.000 description 1
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CLEHVXWHNLSWHK-UHFFFAOYSA-N methyl 2-[4-[3-(2-cyanophenoxy)phenoxy]-2-methyl-6-methylsulfanylpyrimidin-5-yl]acetate Chemical compound N1=C(C)N=C(SC)C(CC(=O)OC)=C1OC1=CC=CC(OC=2C(=CC=CC=2)C#N)=C1 CLEHVXWHNLSWHK-UHFFFAOYSA-N 0.000 description 1
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239000002736 nonionic surfactant Substances 0.000 description 1
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UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
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230000008654 plant damage Effects 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-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
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
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125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 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
239000000377 silicon dioxide Substances 0.000 description 1
238000002791 soaking Methods 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical class [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000000935 solvent evaporation Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
230000009885 systemic effect Effects 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
230000001225 therapeutic effect Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
244000045561 useful plants Species 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
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- C07D239/56—One oxygen atom and one sulfur atom
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

SK335-96A 1995-03-10 1996-03-08 2-(4-alkylthiopyrimidine-5-yl)acetic acid derivative, preparing method thereof and fungicidal agents containing them SK33596A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9504920.1A GB9504920D0 (en)	1995-03-10	1995-03-10	Organic compounds

Publications (1)

Publication Number	Publication Date
SK33596A3 true SK33596A3 (en)	1997-03-05

Family

ID=10771032

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK335-96A SK33596A3 (en)	1995-03-10	1996-03-08	2-(4-alkylthiopyrimidine-5-yl)acetic acid derivative, preparing method thereof and fungicidal agents containing them

Country Status (18)

Country	Link
US (1)	US5776941A (ru)
EP (1)	EP0731095B1 (ru)
JP (1)	JPH08277272A (ru)
KR (1)	KR960034183A (ru)
CN (1)	CN1139671A (ru)
AT (1)	ATE220063T1 (ru)
BR (1)	BR9600979A (ru)
CA (1)	CA2171227A1 (ru)
CZ (1)	CZ69796A3 (ru)
DE (1)	DE69622065T2 (ru)
EA (1)	EA000015B1 (ru)
GB (1)	GB9504920D0 (ru)
HU (1)	HUP9600597A3 (ru)
IL (1)	IL117414A0 (ru)
PL (1)	PL313162A1 (ru)
SK (1)	SK33596A3 (ru)
TR (1)	TR199600181A2 (ru)
ZA (1)	ZA961926B (ru)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6001883A (en) *	1998-06-24	1999-12-14	American Cyanamid Company	Fungicidal 2-methoxybenzophenones
US6948527B2 (en) *	2001-11-24	2005-09-27	Gary Dean Ragner	Pressure-actuated linearly retractable and extendible hose
GB0913636D0 (en)	2009-08-05	2009-09-16	Univ Leuven Kath	Novel viral replication inhibitors

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9106609D0 (en) *	1991-03-28	1991-05-15	Ici Plc	Heterocyclic compounds
EP0506270A1 (en) *	1991-03-28	1992-09-30	Zeneca Limited	Nematocide pyrimidine derivatives
GB9205487D0 (en) *	1991-03-28	1992-04-29	Ici Plc	Heterocyclic compounds
RU94026277A (ru) *	1993-07-12	1996-05-27	Сандоз АГ (CH)	Пиримидиниловые производные акриловой кислоты, способ их получения, способ подавления фитопатогенных грибов, фунгицидное средство
GB9400889D0 (en) *	1994-01-18	1994-03-16	Sandoz Ltd	Novel compounds

1995
- 1995-03-10 GB GBGB9504920.1A patent/GB9504920D0/en active Pending
1996
- 1996-02-26 US US08/606,911 patent/US5776941A/en not_active Expired - Fee Related
- 1996-03-05 TR TR96/00181A patent/TR199600181A2/xx unknown
- 1996-03-05 DE DE69622065T patent/DE69622065T2/de not_active Expired - Fee Related
- 1996-03-05 EP EP96810127A patent/EP0731095B1/en not_active Expired - Lifetime
- 1996-03-05 AT AT96810127T patent/ATE220063T1/de not_active IP Right Cessation
- 1996-03-07 CZ CZ96697A patent/CZ69796A3/cs unknown
- 1996-03-07 CA CA002171227A patent/CA2171227A1/en not_active Abandoned
- 1996-03-07 EA EA199600010A patent/EA000015B1/ru not_active IP Right Cessation
- 1996-03-08 IL IL11741496A patent/IL117414A0/xx unknown
- 1996-03-08 HU HU9600597A patent/HUP9600597A3/hu unknown
- 1996-03-08 JP JP8051839A patent/JPH08277272A/ja not_active Withdrawn
- 1996-03-08 ZA ZA9601926A patent/ZA961926B/xx unknown
- 1996-03-08 KR KR1019960006093A patent/KR960034183A/ko not_active Application Discontinuation
- 1996-03-08 PL PL96313162A patent/PL313162A1/xx unknown
- 1996-03-08 CN CN96103085A patent/CN1139671A/zh active Pending
- 1996-03-08 SK SK335-96A patent/SK33596A3/sk unknown
- 1996-03-11 BR BR9600979A patent/BR9600979A/pt active Search and Examination

Also Published As

Publication number	Publication date
KR960034183A (ko)	1996-10-22
CN1139671A (zh)	1997-01-08
IL117414A0 (en)	1996-07-23
JPH08277272A (ja)	1996-10-22
PL313162A1 (en)	1996-09-16
DE69622065T2 (de)	2002-11-14
GB9504920D0 (en)	1995-04-26
CZ69796A3 (en)	1996-09-11
CA2171227A1 (en)	1996-09-11
TR199600181A2 (tr)	1996-10-21
ATE220063T1 (de)	2002-07-15
ZA961926B (en)	1997-09-08
EA199600010A2 (ru)	1996-10-01
US5776941A (en)	1998-07-07
BR9600979A (pt)	1997-12-30
DE69622065D1 (de)	2002-08-08
EA199600010A3 (ru)	1996-12-30
EA000015B1 (ru)	1997-12-30
EP0731095B1 (en)	2002-07-03
HUP9600597A3 (en)	1997-08-28
EP0731095A1 (en)	1996-09-11
HU9600597D0 (en)	1996-05-28
HUP9600597A2 (en)	1997-04-28

Publication	Publication Date	Title
AU616031B2 (en)	1991-10-17	Alpha-arylacrylates substituted by a heterocyclic radical, and fungicides which contain these compounds
EP0471261B1 (de)	1996-01-17	Pyrimidyl-substituierte Acrylsäureester
US5547919A (en)	1996-08-20	α-pyrimidinyl acrylic acid derivatives
JPH05112541A (ja)	1993-05-07	トリアジニル置換アクリル酸エステル
EP0571326A1 (en)	1993-11-24	Pyrazoles
JPH04217666A (ja)	1992-08-07	複素環式アセトニトリルおよびその殺菌剤的用途
EP0634405B1 (en)	2002-10-30	Pyrimidinyl acrylic acid derivatives, process for their preparation and their use for the control of phytopathogens
SK33596A3 (en)	1997-03-05	2-(4-alkylthiopyrimidine-5-yl)acetic acid derivative, preparing method thereof and fungicidal agents containing them
EP0770611A2 (en)	1997-05-02	Fungicidal 2-(4-Pyrazolyloxy-pyrimidin-5-yl) acetic acid derivatives
JPH06206861A (ja)	1994-07-26	ベンジル誘導体およびこれを含有する殺菌剤
CA2206306A1 (en)	1996-06-13	Novel pyrimidinyloxy- and pyrimidinylamino-ethylphenyl-dioxolane derivatives
JP2909469B2 (ja)	1999-06-23	病害に対する植物の防護剤
US5783580A (en)	1998-07-21	α-pyrimidinyl acrylic acid derivatives
JP2003516384A (ja)	2003-05-13	殺微生物剤、殺虫剤及び殺ダニ剤効果を有するｎ−フェニルカルバメート
WO1997009316A1 (en)	1997-03-13	4-[2-(pyrimidin-4-oxy- or 4-ylamino)-ethyl]-phenyl-oximes
MXPA96004347A (en)	1998-10-23	Acid derivatives 2- (4-pirazolylioxi-pirimidin-5-il) acet