SK82794A3 - Pyrido £2,3-d|pyridazine derivatives, method of their production , compositions which contain them, and their using as herbicides - Google Patents

Pyrido £2,3-d|pyridazine derivatives, method of their production , compositions which contain them, and their using as herbicides Download PDF

Info

Publication number: SK82794A3
Authority: SK; Slovakia
Prior art keywords: optionally substituted; pyrido; group; formula; pyridazin
Prior art date: 1993-07-13

Application number

SK827-94A

Other languages

English (en)

Slovak (sk)

Inventor

Barry David G Haylor

Philip Henry G Smith

Original Assignee

Rhone Poulenc Agriculture

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.)

1993-07-13

Filing date

1994-07-11

Publication date

1995-02-08

1994-07-11 Application filed by Rhone Poulenc Agriculture filed Critical Rhone Poulenc Agriculture

1995-02-08 Publication of SK82794A3 publication Critical patent/SK82794A3/sk

Links

239000000203 mixture Substances 0.000 title claims description 88
238000000034 method Methods 0.000 title claims description 18
150000004892 pyridazines Chemical class 0.000 title claims 13
239000004009 herbicide Substances 0.000 title abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 126
125000000217 alkyl group Chemical group 0.000 claims abstract description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
150000003839 salts Chemical class 0.000 claims abstract description 23
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
239000001301 oxygen Substances 0.000 claims abstract description 12
125000000304 alkynyl group Chemical group 0.000 claims abstract description 11
150000002367 halogens Chemical class 0.000 claims abstract description 11
239000001257 hydrogen Substances 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
241000196324 Embryophyta Species 0.000 claims description 61
-1 3,4-methylenedioxyphenyl Chemical group 0.000 claims description 53
125000005843 halogen group Chemical group 0.000 claims description 43
125000004432 carbon atom Chemical group C* 0.000 claims description 36
230000002363 herbicidal effect Effects 0.000 claims description 32
239000003085 diluting agent Substances 0.000 claims description 21
239000004094 surface-active agent Substances 0.000 claims description 19
239000004480 active ingredient Substances 0.000 claims description 14
DHLCTHXZKHGREA-UHFFFAOYSA-N 6h-pyrido[2,3-d]pyridazin-5-one Chemical compound C1=CC=C2C(=O)NN=CC2=N1 DHLCTHXZKHGREA-UHFFFAOYSA-N 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 13
239000007788 liquid Substances 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
125000004430 oxygen atom Chemical group O* 0.000 claims description 12
229910052717 sulfur Chemical group 0.000 claims description 12
239000000969 carrier Substances 0.000 claims description 11
239000008187 granular material Substances 0.000 claims description 11
125000002723 alicyclic group Chemical group 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 9
125000004076 pyridyl group Chemical group 0.000 claims description 9
JCVHMHTULFSRSX-UHFFFAOYSA-N 6h-pyrido[2,3-d]pyridazine-5-thione Chemical class C1=CC=C2C(=S)NN=CC2=N1 JCVHMHTULFSRSX-UHFFFAOYSA-N 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
239000000843 powder Substances 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 7
125000004434 sulfur atom Chemical group 0.000 claims description 7
FSWMEFOBYUBEFR-UHFFFAOYSA-N 3-chloro-8-(6,7-difluoro-1,3-benzodioxol-5-yl)-6-(4-fluorophenyl)pyrido[2,3-d]pyridazin-5-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C2=CC(Cl)=CN=C2C(C=2C(=C(F)C=3OCOC=3C=2)F)=N1 FSWMEFOBYUBEFR-UHFFFAOYSA-N 0.000 claims description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
239000011593 sulfur Chemical group 0.000 claims description 5
239000004546 suspension concentrate Substances 0.000 claims description 5
DWHIRSWNWDXFMQ-UHFFFAOYSA-N 4h-pyridazin-5-one Chemical compound O=C1CC=NN=C1 DWHIRSWNWDXFMQ-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
ARFXROZBUSLFIJ-UHFFFAOYSA-N 6-(4-chlorophenyl)-8-(6,7-difluoro-1,3-benzodioxol-5-yl)pyrido[2,3-d]pyridazin-5-one Chemical compound FC=1C(F)=C2OCOC2=CC=1C(C1=NC=CC=C1C1=O)=NN1C1=CC=C(Cl)C=C1 ARFXROZBUSLFIJ-UHFFFAOYSA-N 0.000 claims description 3
YHYGBZGVPSKMDZ-UHFFFAOYSA-N 8-(6,7-difluoro-1,3-benzodioxol-5-yl)-3-fluoro-6-[4-(trifluoromethyl)phenyl]pyrido[2,3-d]pyridazin-5-one Chemical compound O=C1C2=CC(F)=CN=C2C(C=2C(=C(F)C=3OCOC=3C=2)F)=NN1C1=CC=C(C(F)(F)F)C=C1 YHYGBZGVPSKMDZ-UHFFFAOYSA-N 0.000 claims description 3
XLOGKWIRNSNQBB-UHFFFAOYSA-N 8-(6,7-difluoro-1,3-benzodioxol-5-yl)-6-(3,4-difluorophenyl)pyrido[2,3-d]pyridazin-5-one Chemical compound C1=C(F)C(F)=CC=C1N1C(=O)C2=CC=CN=C2C(C=2C(=C(F)C=3OCOC=3C=2)F)=N1 XLOGKWIRNSNQBB-UHFFFAOYSA-N 0.000 claims description 3
RQZIMAHWLTUBJB-UHFFFAOYSA-N 8-(6,7-difluoro-2,4-dioxabicyclo[3.2.2]nona-1(7),5,8-trien-9-yl)-6-(4-fluorophenyl)pyrido[2,3-d]pyridazin-5-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C2=CC=CN=C2C(C=2C=3OCOC(=C(C=3F)F)C=2)=N1 RQZIMAHWLTUBJB-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
235000013339 cereals Nutrition 0.000 claims description 3
239000004495 emulsifiable concentrate Substances 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
QYPSGQMLSYHTEU-UHFFFAOYSA-N 4-[8-(6,7-difluoro-1,3-benzodioxol-5-yl)-5-oxopyrido[2,3-d]pyridazin-6-yl]benzonitrile Chemical compound FC=1C(F)=C2OCOC2=CC=1C(C1=NC=CC=C1C1=O)=NN1C1=CC=C(C#N)C=C1 QYPSGQMLSYHTEU-UHFFFAOYSA-N 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
JMMUCCRQQQYVEV-UHFFFAOYSA-N 6-(6,7-difluoro-2,4-dioxabicyclo[3.2.2]nona-1(7),5,8-trien-9-yl)-8-[3-(trifluoromethyl)phenyl]pyrido[2,3-d]pyridazin-5-one Chemical compound FC1=C(F)C=2OCOC1=CC=2N(C(C1=CC=CN=C11)=O)N=C1C1=CC=CC(C(F)(F)F)=C1 JMMUCCRQQQYVEV-UHFFFAOYSA-N 0.000 claims description 2
OXFOGWJSSJPJKJ-UHFFFAOYSA-N 8-(6,7-difluoro-1,3-benzodioxol-5-yl)-3-fluoro-6-(4-fluorophenyl)pyrido[2,3-d]pyridazin-5-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C2=CC(F)=CN=C2C(C=2C(=C(F)C=3OCOC=3C=2)F)=N1 OXFOGWJSSJPJKJ-UHFFFAOYSA-N 0.000 claims description 2
KJDFDAABAZSROQ-UHFFFAOYSA-N 8-(6,7-difluoro-1,3-benzodioxol-5-yl)-6-[4-(trifluoromethyl)phenyl]pyrido[2,3-d]pyridazin-5-one Chemical compound FC=1C(F)=C2OCOC2=CC=1C(C1=NC=CC=C1C1=O)=NN1C1=CC=C(C(F)(F)F)C=C1 KJDFDAABAZSROQ-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
239000004550 soluble concentrate Substances 0.000 claims description 2
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
SAXGJJRTLYVSJQ-UHFFFAOYSA-N 8-(1,3-benzodioxol-4-yl)-6-(4-fluorophenyl)pyrido[2,3-d]pyridazin-5-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C2=CC=CN=C2C(C=2C=3OCOC=3C=CC=2)=N1 SAXGJJRTLYVSJQ-UHFFFAOYSA-N 0.000 claims 1
229920006395 saturated elastomer Polymers 0.000 claims 1
239000004563 wettable powder Substances 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 abstract 4
150000002431 hydrogen Chemical class 0.000 abstract 4
239000005864 Sulphur Chemical group 0.000 abstract 1
125000005741 alkyl alkenyl group Chemical group 0.000 abstract 1
125000000623 heterocyclic group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
238000006243 chemical reaction Methods 0.000 description 40
239000002904 solvent Substances 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 29
239000000243 solution Substances 0.000 description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
238000010992 reflux Methods 0.000 description 22
239000007787 solid Substances 0.000 description 22
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000002689 soil Substances 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
229940125904 compound 1 Drugs 0.000 description 8
235000021186 dishes Nutrition 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
239000002253 acid Substances 0.000 description 7
239000002585 base Substances 0.000 description 7
244000038559 crop plants Species 0.000 description 7
239000000284 extract Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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235000008504 concentrate Nutrition 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
239000012267 brine Substances 0.000 description 5
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239000000460 chlorine Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
238000005507 spraying Methods 0.000 description 5
244000024671 Brassica kaber Species 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
241001148683 Zostera marina Species 0.000 description 4
239000013543 active substance Substances 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
239000004033 plastic Substances 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
239000011734 sodium Substances 0.000 description 4
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239000000725 suspension Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 4
ZZGSTTFOHYZCSM-UHFFFAOYSA-N 2-(6,7-difluoro-1,3-benzodioxole-5-carbonyl)pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1C(=O)C(C(=C1F)F)=CC2=C1OCO2 ZZGSTTFOHYZCSM-UHFFFAOYSA-N 0.000 description 3
240000006995 Abutilon theophrasti Species 0.000 description 3
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235000013479 Amaranthus retroflexus Nutrition 0.000 description 3
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TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical group C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
FEKUXLUOKFSMRO-UHFFFAOYSA-N (4-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(F)C=C1 FEKUXLUOKFSMRO-UHFFFAOYSA-N 0.000 description 2
FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical class C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 2
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229940104261 taurate Drugs 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
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000008096 xylene Substances 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
- 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
- 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
- C07D405/06—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 linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

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

SK827-94A 1993-07-13 1994-07-11 Pyrido £2,3-d|pyridazine derivatives, method of their production , compositions which contain them, and their using as herbicides SK82794A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB939314412A GB9314412D0 (en)	1993-07-13	1993-07-13	New compositions of matter
CN94108590.2A CN1100262A (zh)	1993-07-13	1994-07-17	新型除草剂

Publications (1)

Publication Number	Publication Date
SK82794A3 true SK82794A3 (en)	1995-02-08

Family

ID=36869987

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK827-94A SK82794A3 (en)	1993-07-13	1994-07-11	Pyrido £2,3-d\|pyridazine derivatives, method of their production , compositions which contain them, and their using as herbicides

Country Status (16)

Country	Link
EP (1)	EP0634413A1 (cs)
JP (1)	JPH0789815A (cs)
CN (1)	CN1100262A (cs)
AU (1)	AU6735294A (cs)
BG (1)	BG98898A (cs)
BR (1)	BR9402265A (cs)
CA (1)	CA2127624A1 (cs)
CZ (1)	CZ167894A3 (cs)
FI (1)	FI943318A7 (cs)
GB (1)	GB9314412D0 (cs)
HU (1)	HUT67620A (cs)
IL (1)	IL110286A0 (cs)
MA (1)	MA23264A1 (cs)
MX (1)	MX9405286A (cs)
PL (1)	PL304273A1 (cs)
SK (1)	SK82794A3 (cs)

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CA2521695C (en) *	2003-05-09	2011-08-16	Asahi Glass Company, Limited	Method for producing 3-substituted 2-chloro-5-fluoro-pyridine or its salt
CN100355732C (zh) *	2003-11-03	2007-12-19	上海药明康德新药开发有限公司	2－氯－5－氟－烟酸酯及酸的制备方法
CN100355733C (zh) *	2003-12-09	2007-12-19	无锡药明康德新药开发有限公司	2－氯－5－氟－烟酸的工业化制备方法
DE102010021637A1 (de)	2010-05-26	2011-12-01	Bayer Schering Pharma Aktiengesellschaft	Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung
EA201390060A1 (ru)	2010-07-09	2013-07-30	Байер Интеллектуэль Проперти Гмбх	Аннелированные пиримидины и триазины и их применение для лечения и/или профилактики сердечно-сосудистых заболеваний
DE102010031149A1 (de)	2010-07-09	2012-01-12	Bayer Schering Pharma Aktiengesellschaft	Annellierte Pyrimidine und Triazine und ihre Verwendung
DE102011007891A1 (de)	2011-04-21	2012-10-25	Bayer Pharma Aktiengesellschaft	Annellierte 4-Aminopyrimidine und ihre Verwendung
CN103180327B (zh)	2010-07-09	2016-08-10	拜耳知识产权有限责任公司	稠环的4-氨基嘧啶及其作为可溶性鸟甘酸环化酶的刺激物的用途
DE102011003315A1 (de)	2011-01-28	2012-08-02	Bayer Schering Pharma Aktiengesellschaft	Annellierte Pyrimindine und Triazine und ihre Verwendung
DE102010031148A1 (de)	2010-07-09	2012-01-12	Bayer Schering Pharma Ag	Annellierte 4-Aminopyrimidine und ihre Verwendung
DE102010031666A1 (de)	2010-07-22	2012-01-26	Bayer Schering Pharma Aktiengesellschaft	Carbamat-substituierte Diaminopyrimidine und ihre Verwendung
DE102010031665A1 (de)	2010-07-22	2012-01-26	Bayer Schering Pharma Aktiengesellschaft	Substituierte Oxazolidinone und Oxazinanone und ihre Verwendung
DE102010031667A1 (de)	2010-07-22	2012-01-26	Bayer Schering Pharma Aktiengesellschaft	Substituierte Methyl-pyrimidin-5-ylcarbamate und ihre Verwendung
DE102010040233A1 (de)	2010-09-03	2012-03-08	Bayer Schering Pharma Aktiengesellschaft	Bicyclische Aza-Heterocyclen und ihre Verwendung
DE102011007890A1 (de)	2011-04-21	2012-10-25	Bayer Pharma Aktiengesellschaft	Fluoralkyl-substituierte Pyrazolopyridine und ihre Verwendung
DE102012200357A1 (de)	2012-01-11	2013-07-11	Bayer Intellectual Property Gmbh	Fluoralkyl-substituierte Pyrazolopyridine und ihre Verwendung
JP6005134B2 (ja)	2011-04-21	2016-10-12	バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒＩｎｔｅｌｌｅｃｔｕａｌＰｒｏｐｅｒｔｙＧｍｂＨ	フルオロアルキル置換ピラゾロピリジンおよびその使用
DE102011078715A1 (de)	2011-07-06	2013-01-10	Bayer Pharma AG	Heteroaryl-substituierte Pyrazolopyridine und ihre Verwendung
DE102012200354A1 (de)	2012-01-11	2013-07-11	Bayer Intellectual Property Gmbh	Heteroaryl-substituierte Pyrazolopyridine und ihre Verwendung
CN103906752B (zh)	2011-07-06	2016-08-24	拜耳知识产权有限责任公司	杂芳基取代的吡唑并吡啶及其用作可溶性鸟苷酸环化酶刺激剂的用途
DE102011082041A1 (de)	2011-09-02	2013-03-07	Bayer Pharma AG	Substituierte annellierte Pyrimidine und ihre Verwendung
DE102012200351A1 (de)	2012-01-11	2013-07-11	Bayer Pharma Aktiengesellschaft	Substituierte annellierte Pyrimidine und ihre Verwendung
CN104039784B (zh)	2011-09-02	2017-08-22	拜耳知识产权有限责任公司	取代的增环嘧啶及其用途
WO2013097052A1 (en)	2011-12-30	2013-07-04	Abbott Laboratories	Bromodomain inhibitors
DE102012200360A1 (de)	2012-01-11	2013-07-11	Bayer Intellectual Property Gmbh	Substituierte Triazine und ihre Verwendung
DE102012200352A1 (de)	2012-01-11	2013-07-11	Bayer Intellectual Property Gmbh	Substituierte, annellierte Imidazole und Pyrazole und ihre Verwendung
DE102012200349A1 (de)	2012-01-11	2013-07-11	Bayer Intellectual Property Gmbh	Substituierte annellierte Pyrimidine und Triazine und ihre Verwendung
WO2013131923A1 (de)	2012-03-06	2013-09-12	Bayer Intellectual Property Gmbh	Substituierte azabicyclen und ihre verwendung
MX2015010725A (es)	2013-02-21	2016-05-31	Adverio Pharma Gmbh	Formas de metil {4,6-diamino-2-[1-(2-fluorobencil)-1h-pirazolo [3,4-b] piridino-3-il] pirimidino-5-il} metil carbamato.
MX2015010966A (es)	2013-03-01	2016-04-04	Bayer Pharma AG	Pirimidinas fusionadas sustituidas con trifluorometilo y sus usos.
EP2968323A4 (en)	2013-03-13	2016-12-14	Flatley Discovery Lab	PYRIDAZINONE COMPOUNDS AND METHODS FOR THE TREATMENT OF CYSTIC FIBROSIS
AP2016008970A0 (en)	2013-07-10	2016-01-31	Bayer Pharma AG	Benzyl-1h-pyrazolo[3,4-b]pyridines and use thereof
WO2017121700A1 (de)	2016-01-15	2017-07-20	Bayer Pharma Aktiengesellschaft	1,3-disubstituierte 1h-pyrazolo[3,4-b]pyridin- derivate und ihre verwendung als stimulatoren der löslichen guanylatcyclase
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GB9200689D0 (en) *	1992-01-14	1992-03-11	Rhone Poulenc Agriculture	New compositions of matter
DE4227747A1 (de) *	1992-08-21	1994-02-24	Basf Ag	Heteroaromatisch kondensierte Hydroxypyridoncarbonsäureamide, deren Herstellung und Verwendung

1993
- 1993-07-13 GB GB939314412A patent/GB9314412D0/en active Pending
1994
- 1994-07-07 EP EP94110578A patent/EP0634413A1/en not_active Withdrawn
- 1994-07-08 CA CA002127624A patent/CA2127624A1/en not_active Abandoned
- 1994-07-08 AU AU67352/94A patent/AU6735294A/en not_active Abandoned
- 1994-07-08 BG BG98898A patent/BG98898A/xx unknown
- 1994-07-11 SK SK827-94A patent/SK82794A3/sk unknown
- 1994-07-11 IL IL11028694A patent/IL110286A0/xx unknown
- 1994-07-12 MA MA23575A patent/MA23264A1/fr unknown
- 1994-07-12 HU HU9402076A patent/HUT67620A/hu unknown
- 1994-07-12 BR BR9402265A patent/BR9402265A/pt not_active Application Discontinuation
- 1994-07-12 CZ CZ941678A patent/CZ167894A3/cs unknown
- 1994-07-12 FI FI943318A patent/FI943318A7/fi not_active Application Discontinuation
- 1994-07-12 MX MX9405286A patent/MX9405286A/es unknown
- 1994-07-13 JP JP6161306A patent/JPH0789815A/ja active Pending
- 1994-07-13 PL PL94304273A patent/PL304273A1/xx unknown
- 1994-07-17 CN CN94108590.2A patent/CN1100262A/zh active Pending

Also Published As

Publication number	Publication date
MX9405286A (es)	1995-01-31
AU6735294A (en)	1995-01-27
CA2127624A1 (en)	1995-01-14
EP0634413A1 (en)	1995-01-18
HUT67620A (en)	1995-04-28
MA23264A1 (fr)	1995-04-01
PL304273A1 (en)	1995-01-23
FI943318A7 (fi)	1995-01-14
FI943318A0 (fi)	1994-07-12
GB9314412D0 (en)	1993-08-25
CZ167894A3 (en)	1995-01-18
BR9402265A (pt)	1995-03-14
CN1100262A (zh)	1995-03-22
JPH0789815A (ja)	1995-04-04
BG98898A (en)	1995-06-30
IL110286A0 (en)	1994-10-21
HU9402076D0 (en)	1994-09-28

Publication	Publication Date	Title
SK82794A3 (en)	1995-02-08	Pyrido £2,3-d\|pyridazine derivatives, method of their production , compositions which contain them, and their using as herbicides
JP3078661B2 (ja)	2000-08-21	新規な除草剤
EP0900795B1 (en)	2004-04-21	Benzene derivatives substituted by heterocycles and herbicides
DE69113721T2 (de)	1996-05-02	Isoxazolderivate, Verfahren zu deren Herstellung and deren Anwendung als Herbizide.
SK6493A3 (en)	1993-10-06	Herbicides
CS20492A3 (en)	1992-08-12	2-cyano-1,3-dione derivatives, process of their preparation and herbicidalcompositions containing said derivatives
CS20592A3 (en)	1992-08-12	2-cyano-1,3-dione derivatives, process of their preparation and herbicidalcompositions containing said derivatives
HU212433B (en)	1996-06-28	Herbicidal compositions containing 4-benzoylisoxazole derivatives, process for the production of active ingredients and their application
SI9300317A (sl)	1993-12-31	N-substituirani pirazolni derivati
JP3557230B2 (ja)	2004-08-25	新規な除草剤
JPH05112557A (ja)	1993-05-07	新規な除草剤
DE19711953A1 (de)	1997-09-25	Neue Herbicide
JPH05112558A (ja)	1993-05-07	新規な除草用組成物
WO1999003856A1 (en)	1999-01-28	4-benzoyl-isoxazole- and -pyrazole derivatives and 2-cyano 1,3-dione derivatives as herbicides
PL171954B1 (pl)	1997-07-31	Pochodna 4-benzoiloizoksazolu i sposób wytwarzania pochodnej 4-benzoiloizoksazolu PL PL
US5405826A (en)	1995-04-11	Herbicidal pyridopyridazinones and pyridopyridazinethiones
SK177497A3 (en)	1998-08-05	1,3-oxazin-4-one derivatives as herbicides
CZ5694A3 (en)	1994-07-13	Hydrazone derivatives of nicotinic acid
WO2001047863A2 (en)	2001-07-05	New herbicidal compositions
WO2000035916A1 (en)	2000-06-22	Herbicidal 4-benzoylisoxazoles
JPH05202009A (ja)	1993-08-10	除草剤
HK1003790B (en)	1998-11-06	4-benzoylisoxazole derivatives and their use as herbicides