BG106834A - Производни на пиколиновата киселина и използването им като фунгициди - Google Patents
Производни на пиколиновата киселина и използването им като фунгициди Download PDFInfo
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- BG106834A BG106834A BG106834A BG10683402A BG106834A BG 106834 A BG106834 A BG 106834A BG 106834 A BG106834 A BG 106834A BG 10683402 A BG10683402 A BG 10683402A BG 106834 A BG106834 A BG 106834A
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- radical
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- alkyl
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- 239000000417 fungicide Substances 0.000 title claims abstract description 8
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 title description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 132
- 239000000203 mixture Substances 0.000 claims abstract description 84
- 238000000034 method Methods 0.000 claims abstract description 42
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 18
- -1 mercapto, nitro, thiocyanato Chemical group 0.000 claims description 130
- 241000196324 Embryophyta Species 0.000 claims description 68
- 239000013543 active substance Substances 0.000 claims description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 239000001301 oxygen Substances 0.000 claims description 40
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 239000004094 surface-active agent Substances 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 230000003287 optical effect Effects 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 23
- 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 claims description 22
- 150000001204 N-oxides Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004414 alkyl thio group Chemical group 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 22
- 229910052752 metalloid Inorganic materials 0.000 claims description 22
- 150000002738 metalloids Chemical class 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 17
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 17
- 150000002739 metals Chemical class 0.000 claims description 17
- 239000011593 sulfur Substances 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
- 235000013339 cereals Nutrition 0.000 claims description 16
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 16
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 16
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 13
- 240000007594 Oryza sativa Species 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 10
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 241000233866 Fungi Species 0.000 claims description 9
- 125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 235000007164 Oryza sativa Nutrition 0.000 claims description 8
- 244000061456 Solanum tuberosum Species 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 235000013399 edible fruits Nutrition 0.000 claims description 8
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 230000003032 phytopathogenic effect Effects 0.000 claims description 8
- 235000009566 rice Nutrition 0.000 claims description 8
- 235000013311 vegetables Nutrition 0.000 claims description 8
- 208000031888 Mycoses Diseases 0.000 claims description 7
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 7
- 240000008042 Zea mays Species 0.000 claims description 7
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 7
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 7
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 7
- 235000009973 maize Nutrition 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 235000004431 Linum usitatissimum Nutrition 0.000 claims description 6
- 240000006240 Linum usitatissimum Species 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Chemical group 0.000 claims description 6
- 239000011574 phosphorus Chemical group 0.000 claims description 6
- 239000003880 polar aprotic solvent Substances 0.000 claims description 6
- 235000012015 potatoes Nutrition 0.000 claims description 6
- 125000003441 thioacyl group Chemical group 0.000 claims description 6
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 5
- 235000021536 Sugar beet Nutrition 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 230000009471 action Effects 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 4
- 240000004713 Pisum sativum Species 0.000 claims description 4
- 235000010582 Pisum sativum Nutrition 0.000 claims description 4
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000002689 soil Substances 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 241000219146 Gossypium Species 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- BUXWLJWGNOMMDQ-UHFFFAOYSA-N 4-formamido-3-hydroxy-n-[4-[4-(trifluoromethyl)phenoxy]phenyl]pyridine-2-carboxamide Chemical compound OC1=C(NC=O)C=CN=C1C(=O)NC(C=C1)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 BUXWLJWGNOMMDQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 240000008415 Lactuca sativa Species 0.000 claims description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 2
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 2
- 240000003768 Solanum lycopersicum Species 0.000 claims description 2
- 230000000895 acaricidal effect Effects 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000005667 attractant Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 230000004071 biological effect Effects 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 230000002538 fungal effect Effects 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- SHPLSLBVOGSXSP-UHFFFAOYSA-N n-[4-(4-chlorophenoxy)phenyl]-4-formamido-3-hydroxypyridine-2-carboxamide Chemical compound OC1=C(NC=O)C=CN=C1C(=O)NC(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 SHPLSLBVOGSXSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
- 239000003016 pheromone Substances 0.000 claims description 2
- 235000012045 salad Nutrition 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- AQSRRZGQRFFFGS-UHFFFAOYSA-N 2-methylpyridin-3-ol Chemical class CC1=NC=CC=C1O AQSRRZGQRFFFGS-UHFFFAOYSA-N 0.000 claims 1
- NNVRELSEYURTQE-UHFFFAOYSA-N 4-amino-3-hydroxy-n-[4-(4-methylphenoxy)phenyl]pyridine-2-carboxamide Chemical compound C1=CC(C)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=NC=CC(N)=C1O NNVRELSEYURTQE-UHFFFAOYSA-N 0.000 claims 1
- LJLZVNMXAJPHSA-UHFFFAOYSA-N 4-formamido-3-hydroxy-n-[4-[3-(trifluoromethyl)phenoxy]phenyl]pyridine-2-carboxamide Chemical compound OC1=C(NC=O)C=CN=C1C(=O)NC(C=C1)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 LJLZVNMXAJPHSA-UHFFFAOYSA-N 0.000 claims 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000005108 alkenylthio group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 125000005109 alkynylthio group Chemical group 0.000 claims 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims 1
- 125000004997 halocarbonyl group Chemical group 0.000 claims 1
- 235000021374 legumes Nutrition 0.000 claims 1
- NWBNORAVIXIZTL-UHFFFAOYSA-N nitro thiocyanate Chemical compound [O-][N+](=O)SC#N NWBNORAVIXIZTL-UHFFFAOYSA-N 0.000 claims 1
- 231100000208 phytotoxic Toxicity 0.000 claims 1
- 230000000885 phytotoxic effect Effects 0.000 claims 1
- 238000005067 remediation Methods 0.000 claims 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims 1
- SQQWBSBBCSFQGC-JLHYYAGUSA-N ubiquinone-2 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O SQQWBSBBCSFQGC-JLHYYAGUSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- 150000003254 radicals Chemical class 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000007787 solid Substances 0.000 description 36
- 108090000623 proteins and genes Proteins 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 201000010099 disease Diseases 0.000 description 21
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- ZLBRUAUYWOKUQQ-UHFFFAOYSA-N 3-phenylpyridine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=C1C1=CC=CC=C1 ZLBRUAUYWOKUQQ-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
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- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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Applications Claiming Priority (2)
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| FR0000140A FR2803592A1 (fr) | 2000-01-06 | 2000-01-06 | Nouveaux derives de l'acide 3-hydroxypicolinique, leur procede de preparation et compositions fongicides les contenant. |
| PCT/FR2001/000033 WO2001049666A1 (fr) | 2000-01-06 | 2001-01-05 | Derives de l'acide picolinique et leur utilisation comme fongicides |
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| BG106834A BG106834A (bg) | 2000-01-06 | 2002-06-18 | Производни на пиколиновата киселина и използването им като фунгициди |
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| FR2827286A1 (fr) * | 2001-07-11 | 2003-01-17 | Aventis Cropscience Sa | Nouveaux composes fongicides |
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-
2000
- 2000-01-06 FR FR0000140A patent/FR2803592A1/fr active Pending
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2001
- 2001-01-05 US US10/181,842 patent/US8003799B2/en not_active Expired - Fee Related
- 2001-01-05 RU RU2002120923/04A patent/RU2002120923A/ru unknown
- 2001-01-05 ES ES01903877T patent/ES2272440T3/es not_active Expired - Lifetime
- 2001-01-05 JP JP2001550206A patent/JP4925541B2/ja not_active Expired - Fee Related
- 2001-01-05 SK SK955-2002A patent/SK9552002A3/sk unknown
- 2001-01-05 HN HN2001000005A patent/HN2001000005A/es unknown
- 2001-01-05 HU HU0203958A patent/HUP0203958A3/hu unknown
- 2001-01-05 MX MXPA02006616A patent/MXPA02006616A/es unknown
- 2001-01-05 DE DE60123210T patent/DE60123210T2/de not_active Expired - Lifetime
- 2001-01-05 BR BR0107241-2A patent/BR0107241A/pt not_active IP Right Cessation
- 2001-01-05 KR KR1020027008458A patent/KR20020062773A/ko not_active Withdrawn
- 2001-01-05 IL IL14936101A patent/IL149361A0/xx unknown
- 2001-01-05 WO PCT/FR2001/000033 patent/WO2001049666A1/fr not_active Ceased
- 2001-01-05 EP EP01903877A patent/EP1244627B1/de not_active Expired - Lifetime
- 2001-01-05 AU AU31843/01A patent/AU3184301A/en not_active Abandoned
- 2001-01-05 CA CA002396299A patent/CA2396299A1/fr not_active Abandoned
- 2001-01-05 CN CN01803512A patent/CN1394202A/zh active Pending
- 2001-01-05 CZ CZ20022359A patent/CZ20022359A3/cs unknown
- 2001-01-05 AT AT01903877T patent/ATE340160T1/de not_active IP Right Cessation
- 2001-01-05 PL PL01365057A patent/PL365057A1/xx unknown
- 2001-01-08 IL IL15054201A patent/IL150542A0/xx unknown
- 2001-01-08 BR BR0107425-3A patent/BR0107425A/pt not_active IP Right Cessation
- 2001-01-08 DE DE60119283T patent/DE60119283T2/de not_active Expired - Lifetime
- 2001-01-08 KR KR1020027008772A patent/KR20020084088A/ko not_active Withdrawn
- 2001-01-08 HK HK03104954.3A patent/HK1052699A1/zh unknown
- 2001-01-08 CN CN01803451A patent/CN1411445A/zh active Pending
- 2001-01-08 HU HU0300139A patent/HUP0300139A2/hu unknown
- 2001-01-08 AR ARP010100075A patent/AR029462A1/es unknown
- 2001-01-08 PL PL01365052A patent/PL365052A1/xx unknown
- 2001-01-08 GT GT200100004A patent/GT200100004A/es unknown
- 2001-01-08 CA CA002396306A patent/CA2396306A1/fr not_active Abandoned
- 2001-01-08 US US10/169,855 patent/US7560565B2/en not_active Expired - Fee Related
- 2001-01-08 WO PCT/FR2001/000044 patent/WO2001049667A1/fr not_active Ceased
- 2001-01-08 JP JP2001550207A patent/JP5057625B2/ja not_active Expired - Fee Related
- 2001-01-08 AU AU31850/01A patent/AU3185001A/en not_active Abandoned
- 2001-01-08 EP EP01903885A patent/EP1248771B1/de not_active Expired - Lifetime
- 2001-01-08 CZ CZ20022360A patent/CZ20022360A3/cs unknown
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