SK140295A3 - Condensed bicyclic pyrimidinones, fungicidal agents on their base and inhibition method of plant deseases by using them - Google Patents

Condensed bicyclic pyrimidinones, fungicidal agents on their base and inhibition method of plant deseases by using them Download PDF

Info

Publication number: SK140295A3
Authority: SK; Slovakia
Prior art keywords: carbon atoms; alkyl; haloalkyl; cycloalkyl; optionally substituted
Prior art date: 1993-05-12

Application number

SK1402-95A

Other languages

English (en)

Slovak (sk)

Inventor

James F Bereznak

Zen-Yu Chang

Thomas P Selby

Charlene G Sternberg

Original Assignee

Du Pont

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.)

1993-05-12

Filing date

1994-05-10

Publication date

1996-09-04

1994-05-10 Application filed by Du Pont filed Critical Du Pont

1996-09-04 Publication of SK140295A3 publication Critical patent/SK140295A3/sk

Links

-1 bicyclic pyrimidinones Chemical class 0.000 title claims description 110
238000000034 method Methods 0.000 title claims description 28
239000000417 fungicide Substances 0.000 title abstract description 9
230000005764 inhibitory process Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 109
239000000203 mixture Substances 0.000 claims abstract description 43
229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 9
150000001204 N-oxides Chemical class 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 285
125000000217 alkyl group Chemical group 0.000 claims description 109
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 87
125000001188 haloalkyl group Chemical group 0.000 claims description 81
125000000262 haloalkenyl group Chemical group 0.000 claims description 70
125000000304 alkynyl group Chemical group 0.000 claims description 63
125000003342 alkenyl group Chemical group 0.000 claims description 62
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 56
125000000753 cycloalkyl group Chemical group 0.000 claims description 54
125000005843 halogen group Chemical group 0.000 claims description 52
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 51
125000004438 haloalkoxy group Chemical group 0.000 claims description 43
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 40
125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 33
125000004414 alkyl thio group Chemical group 0.000 claims description 32
125000004093 cyano group Chemical group *C#N 0.000 claims description 32
125000003545 alkoxy group Chemical group 0.000 claims description 31
125000001544 thienyl group Chemical group 0.000 claims description 31
241000196324 Embryophyta Species 0.000 claims description 30
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 28
125000000232 haloalkynyl group Chemical group 0.000 claims description 28
125000004001 thioalkyl group Chemical group 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
125000005082 alkoxyalkenyl group Chemical group 0.000 claims description 25
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 25
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 23
125000002541 furyl group Chemical group 0.000 claims description 23
125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 23
125000005429 oxyalkyl group Chemical group 0.000 claims description 23
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
239000007787 solid Substances 0.000 claims description 20
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
125000004966 cyanoalkyl group Chemical group 0.000 claims description 18
125000001624 naphthyl group Chemical group 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 17
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 15
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 14
125000004663 dialkyl amino group Chemical group 0.000 claims description 14
201000010099 disease Diseases 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
125000004995 haloalkylthio group Chemical group 0.000 claims description 13
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
125000004971 nitroalkyl group Chemical group 0.000 claims description 11
125000004430 oxygen atom Chemical group O* 0.000 claims description 11
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 10
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 10
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
125000006373 (C2-C10) alkyl group Chemical group 0.000 claims description 9
230000000855 fungicidal effect Effects 0.000 claims description 9
125000005493 quinolyl group Chemical group 0.000 claims description 9
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
239000004094 surface-active agent Substances 0.000 claims description 8
241000209140 Triticum Species 0.000 claims description 7
235000021307 Triticum Nutrition 0.000 claims description 7
125000003302 alkenyloxy group Chemical group 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
125000004665 trialkylsilyl group Chemical group 0.000 claims description 7
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
241000221785 Erysiphales Species 0.000 claims description 6
125000005133 alkynyloxy group Chemical group 0.000 claims description 6
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
229920002554 vinyl polymer Polymers 0.000 claims description 6
125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
239000001257 hydrogen Substances 0.000 claims description 5
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 5
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
244000000004 fungal plant pathogen Species 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
FVQAEZOUDXAZGN-UHFFFAOYSA-N 6-bromo-2-propoxy-3-propylquinazolin-4-one Chemical compound C1=C(Br)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FVQAEZOUDXAZGN-UHFFFAOYSA-N 0.000 claims description 3
125000006226 butoxyethyl group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000002619 bicyclic group Chemical group 0.000 claims 8
YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 claims 7
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
229910052799 carbon Inorganic materials 0.000 claims 3
KZPLPWDFXMJJPD-UHFFFAOYSA-N 2-anilino-6,8-diiodo-3-propylquinazolin-4-one Chemical compound N=1C2=C(I)C=C(I)C=C2C(=O)N(CCC)C=1NC1=CC=CC=C1 KZPLPWDFXMJJPD-UHFFFAOYSA-N 0.000 claims 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
125000005292 haloalkynyloxy group Chemical group 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 148
125000001246 bromo group Chemical group Br* 0.000 description 144
101150065749 Churc1 gene Proteins 0.000 description 31
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
102100038239 Protein Churchill Human genes 0.000 description 24
239000003921 oil Substances 0.000 description 23
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 20
239000000243 solution Substances 0.000 description 20
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
239000000460 chlorine Substances 0.000 description 16
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 15
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 14
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 13
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 12
239000000725 suspension Substances 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
239000000047 product Substances 0.000 description 10
244000052769 pathogen Species 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 8
101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 8
XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000008187 granular material Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000000484 butyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
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 6
150000003254 radicals Chemical group 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
238000003756 stirring Methods 0.000 description 6
150000001412 amines Chemical class 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
239000008188 pellet Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241000233866 Fungi Species 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
238000000605 extraction Methods 0.000 description 4
230000001939 inductive effect Effects 0.000 description 4
150000002540 isothiocyanates Chemical class 0.000 description 4
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
230000001717 pathogenic effect Effects 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
CUKXRHLWPSBCTI-UHFFFAOYSA-N 2-amino-5-bromobenzoic acid Chemical compound NC1=CC=C(Br)C=C1C(O)=O CUKXRHLWPSBCTI-UHFFFAOYSA-N 0.000 description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
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 3
238000006073 displacement reaction Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000002917 insecticide Substances 0.000 description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 3
XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 2
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 2
IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 2
LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 description 2
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 2
UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 2
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000895502 Blumeria graminis f. sp. tritici Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000005756 Cymoxanil Substances 0.000 description 2
239000005757 Cyproconazole Substances 0.000 description 2
102100029952 Double-strand-break repair protein rad21 homolog Human genes 0.000 description 2
239000005778 Fenpropimorph Substances 0.000 description 2
101000584942 Homo sapiens Double-strand-break repair protein rad21 homolog Proteins 0.000 description 2
235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
239000005802 Mancozeb Substances 0.000 description 2
208000000450 Pelvic Pain Diseases 0.000 description 2
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XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
241000701447 unidentified baculovirus Species 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- A01N43/72—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
- A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

SK1402-95A 1993-05-12 1994-05-10 Condensed bicyclic pyrimidinones, fungicidal agents on their base and inhibition method of plant deseases by using them SK140295A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US6062993A	1993-05-12	1993-05-12
US14490493A	1993-10-28	1993-10-28
PCT/US1994/004965 WO1994026722A1 (en)	1993-05-12	1994-05-10	Fungicidal fused bicyclic pyrimidinones

Publications (1)

Publication Number	Publication Date
SK140295A3 true SK140295A3 (en)	1996-09-04

Family

ID=26740142

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1402-95A SK140295A3 (en)	1993-05-12	1994-05-10	Condensed bicyclic pyrimidinones, fungicidal agents on their base and inhibition method of plant deseases by using them

Country Status (23)

Country	Link
US (2)	US5747497A (de)
EP (1)	EP0698013B1 (de)
JP (1)	JPH08510243A (de)
CN (1)	CN1050355C (de)
AT (1)	ATE206406T1 (de)
AU (1)	AU6944394A (de)
BR (1)	BR9406662A (de)
CA (1)	CA2162846A1 (de)
CZ (1)	CZ291264B6 (de)
DE (1)	DE69428533T2 (de)
DK (1)	DK0698013T3 (de)
ES (1)	ES2163445T3 (de)
FR (1)	FR09C0038I2 (de)
GR (1)	GR3036942T3 (de)
HU (1)	HU218381B (de)
LV (1)	LV11464B (de)
NZ (1)	NZ267222A (de)
PL (1)	PL174704B1 (de)
PT (1)	PT698013E (de)
RU (1)	RU2139862C1 (de)
SI (1)	SI9420029A (de)
SK (1)	SK140295A3 (de)
WO (1)	WO1994026722A1 (de)

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TW200306155A (en)	2002-03-19	2003-11-16	Du Pont	Benzamides and advantageous compositions thereof for use as fungicides
DE60309166T2 (de) *	2002-06-11	2007-08-16	E.I. Dupont De Nemours And Co., Wilmington	Mischungen von kondensierten pyrimidinonen und dinitrophenolischen verbindungen zur bekämpfung von mehltau
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1994
- 1994-05-10 CN CN94192068A patent/CN1050355C/zh not_active Expired - Lifetime
- 1994-05-10 CZ CZ19952803A patent/CZ291264B6/cs not_active IP Right Cessation
- 1994-05-10 JP JP6525540A patent/JPH08510243A/ja active Pending
- 1994-05-10 ES ES94917917T patent/ES2163445T3/es not_active Expired - Lifetime
- 1994-05-10 SK SK1402-95A patent/SK140295A3/sk unknown
- 1994-05-10 BR BR9406662A patent/BR9406662A/pt not_active Application Discontinuation
- 1994-05-10 DK DK94917917T patent/DK0698013T3/da active
- 1994-05-10 US US08/545,827 patent/US5747497A/en not_active Expired - Lifetime
- 1994-05-10 HU HU9503173A patent/HU218381B/hu active Protection Beyond IP Right Term
- 1994-05-10 CA CA002162846A patent/CA2162846A1/en not_active Abandoned
- 1994-05-10 AU AU69443/94A patent/AU6944394A/en not_active Abandoned
- 1994-05-10 SI SI9420029A patent/SI9420029A/sl unknown
- 1994-05-10 PL PL94311641A patent/PL174704B1/pl unknown
- 1994-05-10 EP EP94917917A patent/EP0698013B1/de not_active Expired - Lifetime
- 1994-05-10 NZ NZ267222A patent/NZ267222A/en not_active IP Right Cessation
- 1994-05-10 AT AT94917917T patent/ATE206406T1/de active
- 1994-05-10 PT PT94917917T patent/PT698013E/pt unknown
- 1994-05-10 DE DE69428533T patent/DE69428533T2/de not_active Expired - Lifetime
- 1994-05-10 WO PCT/US1994/004965 patent/WO1994026722A1/en not_active Ceased
- 1994-05-10 RU RU95121800A patent/RU2139862C1/ru active Protection Beyond IP Right Term
1995
- 1995-11-10 LV LVP-95-339A patent/LV11464B/en unknown
1998
- 1998-01-14 US US09/007,336 patent/US5945423A/en not_active Expired - Lifetime
2001
- 2001-10-18 GR GR20010401811T patent/GR3036942T3/el unknown
2009
- 2009-08-14 FR FR09C0038C patent/FR09C0038I2/fr active Active

Also Published As

Publication number	Publication date
AU6944394A (en)	1994-12-12
CA2162846A1 (en)	1994-11-24
GR3036942T3 (en)	2002-01-31
HU9503173D0 (en)	1995-12-28
DE69428533D1 (de)	2001-11-08
WO1994026722A1 (en)	1994-11-24
US5945423A (en)	1999-08-31
CZ280395A3 (en)	1996-03-13
EP0698013A1 (de)	1996-02-28
PL311641A1 (en)	1996-03-04
SI9420029A (en)	1996-10-31
DE69428533T2 (de)	2002-05-23
DK0698013T3 (da)	2001-12-10
CN1050355C (zh)	2000-03-15
HUT72829A (en)	1996-05-28
FR09C0038I2 (de)	2010-06-11
US5747497A (en)	1998-05-05
LV11464B (en)	1997-02-20
NZ267222A (en)	1996-10-28
ATE206406T1 (de)	2001-10-15
PT698013E (pt)	2002-01-30
RU2139862C1 (ru)	1999-10-20
FR09C0038I1 (de)	2009-09-25
LV11464A (lv)	1996-08-20
BR9406662A (pt)	1996-02-06
ES2163445T3 (es)	2002-02-01
CZ291264B6 (cs)	2003-01-15
EP0698013B1 (de)	2001-10-04
JPH08510243A (ja)	1996-10-29
HU218381B (hu)	2000-08-28
PL174704B1 (pl)	1998-09-30
CN1123028A (zh)	1996-05-22

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EP0946095A1 (de)	1999-10-06	Fungizide chinazolinone
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EP0642502B1 (de)	2000-07-12	Fungizide imidazolinone
WO1993023398A1 (en)	1993-11-25	Substituted pyrido[1,2-a]pyrimidinone derivatives as fungicides
WO1993022311A1 (en)	1993-11-11	Fungicidal 1,3,4-oxadiazines and 1,3,4-thiadiazines
WO1996026191A1 (en)	1996-08-29	Fungicidal cyclic amides
WO1992019615A2 (en)	1992-11-12	Fungicidal pyrazoles, pyrazolines and tetrahydropyridazines
WO2000051992A1 (en)	2000-09-08	Fused bicyclic oxazinone and thiazinone fungicides
US6255311B1 (en)	2001-07-03	Fungicidal fused bicyclic pyrimidinones
EP0937051A1 (de)	1999-08-25	Fungizide cyclische amide
USH1829H (en)	2000-01-04	Fungicidal fused bicyclic pyrimidinones