ZA200504296B - Pyridodiazines as plant fungicides. - Google Patents

Info

Publication number

ZA200504296B

ZA200504296B ZA200504296A ZA200504296A ZA200504296B ZA 200504296 B ZA200504296 B ZA 200504296B ZA 200504296 A ZA200504296 A ZA 200504296A ZA 200504296 A ZA200504296 A ZA 200504296A ZA 200504296 B ZA200504296 B ZA 200504296B

Authority

ZA

South Africa

Prior art keywords

alkyl

compounds

halo

alkoxy

same

Prior art date

2002-12-23

Links

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• 239000000417 fungicide Substances 0.000 title description 6
• OHZYAOYVLLHTGW-UHFFFAOYSA-N pyrido[3,2-c]pyridazine Chemical class C1=CN=NC2=CC=CN=C21 OHZYAOYVLLHTGW-UHFFFAOYSA-N 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 1476
• 125000000217 alkyl group Chemical group 0.000 claims description 298
• -1 Cys alkylthio Chemical group 0.000 claims description 284
• 125000005843 halogen group Chemical group 0.000 claims description 172
• 125000003545 alkoxy group Chemical group 0.000 claims description 138
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 91
• 239000000203 mixture Substances 0.000 claims description 78
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 72
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 61
• 125000003118 aryl group Chemical group 0.000 claims description 60
• 125000001072 heteroaryl group Chemical group 0.000 claims description 58
• 125000003342 alkenyl group Chemical group 0.000 claims description 55
• 125000004414 alkyl thio group Chemical group 0.000 claims description 51
• 125000000304 alkynyl group Chemical group 0.000 claims description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 39
• 125000001424 substituent group Chemical group 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
• 125000002947 alkylene group Chemical group 0.000 claims description 19
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
• 125000001153 fluoro group Chemical group F* 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 238000000034 method Methods 0.000 claims description 16
• YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 claims description 15
• 125000005103 alkyl silyl group Chemical group 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 229910052727 yttrium Inorganic materials 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 241000233866 Fungi Species 0.000 claims description 11
• 125000004450 alkenylene group Chemical group 0.000 claims description 11
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
• 239000001257 hydrogen Substances 0.000 claims description 11
• 230000000855 fungicidal effect Effects 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000004104 aryloxy group Chemical group 0.000 claims description 8
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 239000002689 soil Substances 0.000 claims description 8
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 150000001412 amines Chemical class 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 125000005110 aryl thio group Chemical group 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 125000005368 heteroarylthio group Chemical group 0.000 claims description 5
• 230000003032 phytopathogenic effect Effects 0.000 claims description 5
• 239000001963 growth medium Substances 0.000 claims description 4
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 230000008635 plant growth Effects 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000000175 2-thienyl group Chemical group S1C([*])=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
• 239000013461 intermediate chemical Substances 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
• 125000006414 CCl Chemical group ClC* 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• KMJZFJMFHOPFPJ-UHFFFAOYSA-N n-phenylpiperidin-1-amine Chemical compound C1CCCCN1NC1=CC=CC=C1 KMJZFJMFHOPFPJ-UHFFFAOYSA-N 0.000 claims 1
• 229940125904 compound 1 Drugs 0.000 description 163
• 239000002904 solvent Substances 0.000 description 39
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
• 238000006243 chemical reaction Methods 0.000 description 26
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
• 239000007787 solid Substances 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
• 239000000460 chlorine Substances 0.000 description 19
• 241000196324 Embryophyta Species 0.000 description 16
• 239000007788 liquid Substances 0.000 description 15
• 239000003921 oil Substances 0.000 description 15
• 235000019198 oils Nutrition 0.000 description 14
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• 235000021307 Triticum Nutrition 0.000 description 12
• 241000209140 Triticum Species 0.000 description 12
• 238000002360 preparation method Methods 0.000 description 12
• 239000000243 solution Substances 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• 238000005481 NMR spectroscopy Methods 0.000 description 11
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 238000009472 formulation Methods 0.000 description 11
• 239000000843 powder Substances 0.000 description 11
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
• 239000004480 active ingredient Substances 0.000 description 10
• 239000004495 emulsifiable concentrate Substances 0.000 description 10
• 239000008187 granular material Substances 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 9
• 101150065749 Churc1 gene Proteins 0.000 description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 102100038239 Protein Churchill Human genes 0.000 description 9
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
• 240000005979 Hordeum vulgare Species 0.000 description 7
• 235000007340 Hordeum vulgare Nutrition 0.000 description 7
• 235000007688 Lycopersicon esculentum Nutrition 0.000 description 7
• 241000220225 Malus Species 0.000 description 7
• 240000003768 Solanum lycopersicum Species 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• 235000019441 ethanol Nutrition 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• 238000003818 flash chromatography Methods 0.000 description 7
• 239000004530 micro-emulsion Substances 0.000 description 7
• 235000021391 short chain fatty acids Nutrition 0.000 description 7
• 239000004546 suspension concentrate Substances 0.000 description 7
• 238000011282 treatment Methods 0.000 description 7
• 244000105624 Arachis hypogaea Species 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• 235000021016 apples Nutrition 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 150000002576 ketones Chemical class 0.000 description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
• 235000020232 peanut Nutrition 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical class N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 229910000104 sodium hydride Inorganic materials 0.000 description 6
• 239000007921 spray Substances 0.000 description 6
• 235000013311 vegetables Nutrition 0.000 description 6
• 239000000080 wetting agent Substances 0.000 description 6
• 208000016057 CHAND syndrome Diseases 0.000 description 5
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
• 240000007594 Oryza sativa Species 0.000 description 5
• 235000007164 Oryza sativa Nutrition 0.000 description 5
• 241000220324 Pyrus Species 0.000 description 5
• 235000002595 Solanum tuberosum Nutrition 0.000 description 5
• 244000061456 Solanum tuberosum Species 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• 239000011575 calcium Substances 0.000 description 5
• 239000004491 dispersible concentrate Substances 0.000 description 5
• 239000002270 dispersing agent Substances 0.000 description 5
• 239000006185 dispersion Substances 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
• 235000019341 magnesium sulphate Nutrition 0.000 description 5
• 229910052751 metal Inorganic materials 0.000 description 5
• 239000002184 metal Substances 0.000 description 5
• 238000002156 mixing Methods 0.000 description 5
• 235000021017 pears Nutrition 0.000 description 5
• 235000012015 potatoes Nutrition 0.000 description 5
• 235000009566 rice Nutrition 0.000 description 5
• 150000003839 salts Chemical class 0.000 description 5
• 239000004094 surface-active agent Substances 0.000 description 5
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
• 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
• 240000002791 Brassica napus Species 0.000 description 4
• 235000006008 Brassica napus var napus Nutrition 0.000 description 4
• 244000068988 Glycine max Species 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• 235000021536 Sugar beet Nutrition 0.000 description 4
• 239000000654 additive Substances 0.000 description 4
• 239000012267 brine Substances 0.000 description 4
• 125000001246 bromo group Chemical group Br* 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 235000013339 cereals Nutrition 0.000 description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
• 235000014113 dietary fatty acids Nutrition 0.000 description 4
• 201000010099 disease Diseases 0.000 description 4
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• 239000012074 organic phase Substances 0.000 description 4
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• NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
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• 239000012312 sodium hydride Substances 0.000 description 4
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
• 239000004562 water dispersible granule Substances 0.000 description 4
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• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
• 239000005864 Sulphur Chemical group 0.000 description 3
• 239000002253 acid Substances 0.000 description 3
• 150000001299 aldehydes Chemical class 0.000 description 3
• 235000021015 bananas Nutrition 0.000 description 3
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• 238000010168 coupling process Methods 0.000 description 3
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• XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
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• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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• 238000003756 stirring Methods 0.000 description 3
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• NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
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• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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• ZGTKKOBEHOWTTC-UHFFFAOYSA-N 6,8-dichloro-7-(2,4,6-trifluorophenyl)pyrido[2,3-b]pyrazine Chemical compound FC1=CC(F)=CC(F)=C1C1=C(Cl)N=C(N=CC=N2)C2=C1Cl ZGTKKOBEHOWTTC-UHFFFAOYSA-N 0.000 description 2
• OFIZBESSSBEZMW-UHFFFAOYSA-N 6-chloro-n-propan-2-yl-7-(2,4,6-trifluorophenyl)pyrido[3,2-c]pyridazin-8-amine Chemical compound ClC1=NC2=CC=NN=C2C(NC(C)C)=C1C1=C(F)C=C(F)C=C1F OFIZBESSSBEZMW-UHFFFAOYSA-N 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
• 244000291564 Allium cepa Species 0.000 description 2
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