HUT64760A - Substituted pyrido (2,3-d) pyrimidine-2,4 (1h, 3h) diones, process for preparing and using the compounds and herbicidal compositions of diminished fitotoxicity - Google Patents

Substituted pyrido (2,3-d) pyrimidine-2,4 (1h, 3h) diones, process for preparing and using the compounds and herbicidal compositions of diminished fitotoxicity Download PDF

Info

Publication number: HUT64760A
Authority: HU; Hungary
Prior art keywords: alkyl; alkylthio; formula; alkoxy; substituted
Prior art date: 1990-11-08

Application number

HU9301337A

Other languages

English (en)

Hungarian (hu)

Other versions

HU9301337D0 (en

Inventor

Helmut Hagen

Peter Raatz

Helmut Walter

Andreas Landes

Original Assignee

Basf 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.)

1990-11-08

Filing date

1991-10-30

Publication date

1994-02-28

1991-10-30 Application filed by Basf Ag filed Critical Basf Ag

1993-09-28 Publication of HU9301337D0 publication Critical patent/HU9301337D0/hu

1994-02-28 Publication of HUT64760A publication Critical patent/HUT64760A/hu

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 96
230000002363 herbicidal effect Effects 0.000 title claims abstract description 33
JQPYINKVAWEQDQ-UHFFFAOYSA-N 1h-pyrido[2,3-d]pyrimidine-2,4-dione Chemical class C1=CC=C2C(=O)NC(=O)NC2=N1 JQPYINKVAWEQDQ-UHFFFAOYSA-N 0.000 title claims abstract description 5
239000000203 mixture Substances 0.000 title description 9
230000003292 diminished effect Effects 0.000 title 1
238000004519 manufacturing process Methods 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 65
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 60
239000004009 herbicide Substances 0.000 claims abstract description 44
125000003545 alkoxy group Chemical group 0.000 claims abstract description 36
229910052736 halogen Inorganic materials 0.000 claims abstract description 29
150000002367 halogens Chemical class 0.000 claims abstract description 28
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 25
125000003118 aryl group Chemical group 0.000 claims abstract description 23
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims abstract description 21
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 20
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 16
229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
239000001301 oxygen Substances 0.000 claims abstract description 14
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 13
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims abstract description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 9
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims abstract description 7
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
125000002947 alkylene group Chemical group 0.000 claims abstract description 6
239000002253 acid Substances 0.000 claims abstract description 5
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
-1 amino, hydroxy, mercapto Chemical class 0.000 claims description 143
239000001257 hydrogen Substances 0.000 claims description 50
229910052739 hydrogen Inorganic materials 0.000 claims description 50
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
150000002431 hydrogen Chemical class 0.000 claims description 32
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
238000000034 method Methods 0.000 claims description 12
239000004480 active ingredient Substances 0.000 claims description 11
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
125000004434 sulfur atom Chemical group 0.000 claims description 9
230000012010 growth Effects 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
244000038559 crop plants Species 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
206010029897 Obsessive thoughts Diseases 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
150000003230 pyrimidines Chemical class 0.000 claims description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
150000002690 malonic acid derivatives Chemical class 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
238000009331 sowing Methods 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 3
230000002401 inhibitory effect Effects 0.000 claims 2
LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-aminouracil Chemical class NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 claims 1
125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 1
125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
239000000729 antidote Substances 0.000 abstract description 39
125000003107 substituted aryl group Chemical group 0.000 abstract description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract description 4
229910052757 nitrogen Inorganic materials 0.000 abstract description 4
125000004450 alkenylene group Chemical group 0.000 abstract description 3
229940075522 antidotes Drugs 0.000 abstract description 3
239000000126 substance Substances 0.000 abstract description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
125000001769 aryl amino group Chemical group 0.000 abstract description 2
125000004663 dialkyl amino group Chemical group 0.000 abstract description 2
125000001188 haloalkyl group Chemical group 0.000 abstract description 2
235000019260 propionic acid Nutrition 0.000 abstract description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract description 2
101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 abstract 1
239000005864 Sulphur Substances 0.000 abstract 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
210000002435 tendon Anatomy 0.000 description 193
241000196324 Embryophyta Species 0.000 description 25
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 description 14
241000209140 Triticum Species 0.000 description 10
235000021307 Triticum Nutrition 0.000 description 10
239000004575 stone Substances 0.000 description 10
244000025254 Cannabis sativa Species 0.000 description 9
240000008042 Zea mays Species 0.000 description 9
230000006378 damage Effects 0.000 description 9
235000002017 Zea mays subsp mays Nutrition 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
101100310222 Caenorhabditis briggsae she-1 gene Proteins 0.000 description 6
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
235000009973 maize Nutrition 0.000 description 6
239000003921 oil Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
235000002248 Setaria viridis Nutrition 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
244000304962 green bristle grass Species 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
125000001624 naphthyl group Chemical group 0.000 description 5
239000007787 solid Substances 0.000 description 5
241000209504 Poaceae Species 0.000 description 4
239000013543 active substance Substances 0.000 description 4
239000004359 castor oil Substances 0.000 description 4
235000019438 castor oil Nutrition 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
235000013312 flour Nutrition 0.000 description 4
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
125000005553 heteroaryloxy group Chemical group 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
239000002674 ointment Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
150000003254 radicals Chemical group 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
244000100545 Lolium multiflorum Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000000969 carrier Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000008187 granular material Substances 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
159000000018 pyrido[2,3-d]pyrimidines Chemical class 0.000 description 3
150000008518 pyridopyrimidines Chemical class 0.000 description 3
238000005507 spraying Methods 0.000 description 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
150000005007 4-aminopyrimidines Chemical class 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
101100334117 Caenorhabditis elegans fah-1 gene Proteins 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241001057636 Dracaena deremensis Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000010949 copper Substances 0.000 description 2
235000005822 corn Nutrition 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
239000002612 dispersion medium Substances 0.000 description 2
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000003973 irrigation Methods 0.000 description 2
230000002262 irrigation Effects 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
229920005610 lignin Polymers 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000004033 plastic Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
125000005504 styryl group Chemical group 0.000 description 2
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
125000006248 tosyl amino group Chemical group [H]N(*)S(=O)(=O)C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
FTAPDLRVRYASRX-UHFFFAOYSA-N 1,3-oxazolidine-2-carboxamide Chemical compound NC(=O)C1NCCO1 FTAPDLRVRYASRX-UHFFFAOYSA-N 0.000 description 1
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
YIFCWYUSYGFFMH-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedioic acid Chemical class CCOC=C(C(O)=O)C(O)=O YIFCWYUSYGFFMH-UHFFFAOYSA-N 0.000 description 1
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
ALJWFMYFYMJRKQ-UHFFFAOYSA-N 3-(dimethylamino)-3-nitro-1-phenylpropan-1-one;hydrochloride Chemical compound Cl.CN(C)C([N+]([O-])=O)CC(=O)C1=CC=CC=C1 ALJWFMYFYMJRKQ-UHFFFAOYSA-N 0.000 description 1
XVBAOJCDXBMWMR-UHFFFAOYSA-N 3-chloro-2-methylpent-2-enal Chemical compound CCC(Cl)=C(C)C=O XVBAOJCDXBMWMR-UHFFFAOYSA-N 0.000 description 1
PDZKNPQAPGGAFJ-UHFFFAOYSA-N 4-aminopyrimidine-5-carbaldehyde Chemical class NC1=NC=NC=C1C=O PDZKNPQAPGGAFJ-UHFFFAOYSA-N 0.000 description 1
LAIKNOKKNYFUNY-UHFFFAOYSA-N 5-ethyl-1,3,6-trimethylpyrido[2,3-d]pyrimidine-2,4-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CC(C)=C2CC LAIKNOKKNYFUNY-UHFFFAOYSA-N 0.000 description 1
VFGRNTYELNYSKJ-UHFFFAOYSA-N 6-amino-1,3-dimethylpyrimidine-2,4-dione Chemical compound CN1C(N)=CC(=O)N(C)C1=O VFGRNTYELNYSKJ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
CZHQPNNXTPWHAW-UHFFFAOYSA-N CC(C(C=C(N)N1C)=O)C1=O Chemical compound CC(C(C=C(N)N1C)=O)C1=O CZHQPNNXTPWHAW-UHFFFAOYSA-N 0.000 description 1
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241000282461 Canis lupus Species 0.000 description 1
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239000003815 herbicide antidote Substances 0.000 description 1
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229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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239000002609 medium Substances 0.000 description 1
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PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
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229910052625 palygorskite Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
150000005599 propionic acid derivatives Chemical class 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000004576 sand Substances 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
239000000932 sedative agent Substances 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000000758 substrate Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
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 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Landscapes

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

HU9301337A 1990-11-08 1991-10-30 Substituted pyrido (2,3-d) pyrimidine-2,4 (1h, 3h) diones, process for preparing and using the compounds and herbicidal compositions of diminished fitotoxicity HUT64760A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4035479A DE4035479A1 (de)	1990-11-08	1990-11-08	Substituierte pyrido (2,3-d)pyrimidin-2,4(1h,3h)-dione

Publications (2)

Publication Number	Publication Date
HU9301337D0 HU9301337D0 (en)	1993-09-28
HUT64760A true HUT64760A (en)	1994-02-28

Family

ID=6417854

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU9301337A HUT64760A (en)	1990-11-08	1991-10-30	Substituted pyrido (2,3-d) pyrimidine-2,4 (1h, 3h) diones, process for preparing and using the compounds and herbicidal compositions of diminished fitotoxicity

Country Status (7)

Country	Link
EP (1)	EP0556225A1 (ja)
JP (1)	JPH06502152A (ja)
KR (1)	KR930702293A (ja)
CA (1)	CA2095433A1 (ja)
DE (1)	DE4035479A1 (ja)
HU (1)	HUT64760A (ja)
WO (1)	WO1992008719A1 (ja)

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* Cited by examiner, † Cited by third party
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DE4131029A1 (de) *	1991-09-18	1993-07-29	Basf Ag	Substituierte pyrido (2,3-d) pyrimidine als antidots
US5502177A (en)	1993-09-17	1996-03-26	Gilead Sciences, Inc.	Pyrimidine derivatives for labeled binding partners
US5776942A (en) *	1994-06-17	1998-07-07	Nippon Zoki Pharmaceutical Co., Ltd.	Bronchodilating pyrido 2,3-d!pyrimidine derivatives
JP2000119272A (ja)	1998-10-15	2000-04-25	Nippon Zoki Pharmaceut Co Ltd	新規７−アミノピリド〔２，３−ｄ〕ピリミジン誘導体
TWI243055B (en)	2000-04-13	2005-11-11	Nippon Zoki Pharmaceutical Co	Pharmaceutical composition for use in treatment of dermatitis
FR2832711B1 (fr)	2001-11-26	2004-01-30	Warner Lambert Co	Derives de triazolo [4,3-a] pyrido [2,3-d] pyrimidin-5-ones, compositions les contenant, procede de preparation et utilisation
US7378423B2 (en)	2004-06-11	2008-05-27	Japan Tobacco Inc.	Pyrimidine compound and medical use thereof
SI1761528T1 (sl) *	2004-06-11	2008-06-30	Japan Tobacco Inc	5-amino-2,4,7-triokso-3,4,7,8-tetrahidro-2H-pirido(2,3-D)pirimidinski derivati in sorodne spojine za zdravljenje raka
GB0427568D0 (en)	2004-12-16	2005-01-19	Resolution Chemicals Ltd	Particle-size reduction apparatus, and the use thereof
CN101597277B (zh) *	2008-06-04	2011-08-03	山东新时代药业有限公司	S-泮托拉唑及盐的制备方法
EP3152207B1 (en)	2014-06-03	2019-05-08	Novartis AG	Pyridopyrimidinedione derivatives as suppressors of non-sens mutations
AR100706A1 (es)	2014-06-03	2016-10-26	Novartis Ag	Derivados de naftiridinadiona
CN108727367B (zh) *	2017-04-18	2021-01-05	山东先达农化股份有限公司	含吡啶并嘧啶二酮的苯并噁嗪酮类化合物及其制备方法和应用和除草剂组合物
US11919895B2 (en) *	2019-10-25	2024-03-05	Saint Louis University	GPR183 antagonists for the treatment of pain
CN114621244B (zh) *	2020-12-14	2023-08-18	成都百裕制药股份有限公司	吡啶衍生物及其在医药上的应用
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1990
- 1990-11-08 DE DE4035479A patent/DE4035479A1/de not_active Withdrawn
1991
- 1991-10-30 HU HU9301337A patent/HUT64760A/hu unknown
- 1991-10-30 WO PCT/EP1991/002055 patent/WO1992008719A1/de not_active Ceased
- 1991-10-30 KR KR1019930701368A patent/KR930702293A/ko not_active Withdrawn
- 1991-10-30 CA CA002095433A patent/CA2095433A1/en not_active Abandoned
- 1991-10-30 EP EP91918853A patent/EP0556225A1/de not_active Withdrawn
- 1991-10-30 JP JP3517111A patent/JPH06502152A/ja active Pending

Also Published As

Publication number	Publication date
HU9301337D0 (en)	1993-09-28
WO1992008719A1 (de)	1992-05-29
CA2095433A1 (en)	1992-05-09
DE4035479A1 (de)	1992-05-14
EP0556225A1 (de)	1993-08-25
KR930702293A (ko)	1993-09-08
JPH06502152A (ja)	1994-03-10

Legal Events

Date	Code	Title	Description
1995-05-29	DFA9	Temporary prot. cancelled due to abandonment

Publication	Publication Date	Title
HUT64760A (en)	1994-02-28	Substituted pyrido (2,3-d) pyrimidine-2,4 (1h, 3h) diones, process for preparing and using the compounds and herbicidal compositions of diminished fitotoxicity
EP0343752B1 (en)	1993-12-01	Alkoxy-1,2,4-triazolo (1,5-c) pyrimidine-2-sulfonamides, process for their preparation and intermediates
KR100467128B1 (ko)	2005-01-24	Ｎ-(5,7-디메톡시[1,2,4]트리아졸로[1,5-ａ]피리미딘-2-일)아릴설폰아미드 화합물 및 제초제로서의 이의 용도
KR900006836B1 (ko)	1990-09-22	2-페녹시피리미딘 유도체 및 제초 조성물
US4565887A (en)	1986-01-21	N-Phenylsulfonamides
EP0537423B1 (en)	1997-10-08	N-pyrazolyl-1,2,4-triazolo(1,5-c)pyrimidine-2-sulfonamide herbicides
JPS5989669A (ja)	1984-05-23	除草活性を有する尿素誘導体
HU228800B1 (en)	2013-05-28	Synergistic herbicidal composition and use thereof
GB1587938A (en)	1981-04-15	Thiadiazolotriazinediones
EP0739341A1 (en)	1996-10-30	Herbicidal aryl and heteroaryl pyrimidines
DD260212A5 (de)	1988-09-21	Herbizide zusammensetzung
IE47879B1 (en)	1984-07-11	2-(or 4-)-amino-5-alkylthio-pyrimidines herbicides
US4266056A (en)	1981-05-05	Phenyl uracils
EP0150974A2 (en)	1985-08-07	Novel sulfonamides derived from substituted 2-amino-1,2,4-triazolo(1,5-a)pyrimidines and compositions and methods of controlling undesired vegetation
HU204830B (en)	1992-02-28	Herbicidal compositions comprising sulfonamide derivatives and process for producing the active ingredients
EP0407888B1 (de)	1994-03-09	Pyrimido(5,4-e)-as-triazin-5,7(6H,8H)-dione zur Bekämpfung unerwünschten Pflanzenwuchses
EP0401582B1 (de)	1994-07-20	Fünfring-heterocyclisch anellierte Chinolinderivate
JPH04226964A (ja)	1992-08-17	除草剤スルホニルウレア誘導体
JPH02268183A (ja)	1990-11-01	置換１，８―ナフチリジン及びこれを含有する除草剤
GB2050355A (en)	1981-01-07	3,5-dioxo-1,2,4-triazine derivatives and their use and production
US4338318A (en)	1982-07-06	Novel compositions and methods
US5461161A (en)	1995-10-24	N-pyridinyl[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides
US3940391A (en)	1976-02-24	3,4-Dihydro-1,2,4-triazine compounds
NZ203188A (en)	1985-03-20	Thiadiazole semicarbazones and semicarbazides:herbicides
AU686846B2 (en)	1998-02-12	N-pyridinyl(1,2,4)triazolo(1,5-c)pyrimidine-2-sulfonamide herbicides