CA2183621A1 - Compositions having synergistic fungitoxic effects - Google Patents
Compositions having synergistic fungitoxic effectsInfo
- Publication number
- CA2183621A1 CA2183621A1 CA002183621A CA2183621A CA2183621A1 CA 2183621 A1 CA2183621 A1 CA 2183621A1 CA 002183621 A CA002183621 A CA 002183621A CA 2183621 A CA2183621 A CA 2183621A CA 2183621 A1 CA2183621 A1 CA 2183621A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- composition
- pyridazinone
- alkyl
- chlorophenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 230000002464 fungitoxic effect Effects 0.000 title abstract description 3
- 230000002195 synergetic effect Effects 0.000 title abstract description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 39
- 239000000194 fatty acid Substances 0.000 claims abstract description 39
- 229930195729 fatty acid Natural products 0.000 claims abstract description 39
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 241000233866 Fungi Species 0.000 claims abstract description 9
- 230000002538 fungal effect Effects 0.000 claims abstract description 9
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims abstract description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 54
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 36
- 235000021314 Palmitic acid Nutrition 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- -1 hydrazidal Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 159000000000 sodium salts Chemical class 0.000 claims description 8
- 150000003863 ammonium salts Chemical class 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 230000003032 phytopathogenic effect Effects 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000002023 wood Substances 0.000 claims description 4
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims description 3
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 3
- 101150113676 chr1 gene Proteins 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 3
- 150000002739 metals Chemical class 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 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 2
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical class CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 claims 18
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical class [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 claims 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- 159000000001 potassium salts Chemical class 0.000 claims 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
- 206010017533 Fungal infection Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000005086 alkoxycarbonylalkynyl group Chemical group 0.000 claims 1
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- 230000001857 anti-mycotic effect Effects 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 125000004953 trihalomethyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 10
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 231100000162 fungitoxic Toxicity 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 230000000855 fungicidal effect Effects 0.000 description 20
- 125000005843 halogen group Chemical group 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000417 fungicide Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 239000003429 antifungal agent Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 230000017066 negative regulation of growth Effects 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241001330975 Magnaporthe oryzae Species 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- BEKZXQKGTDVSKX-UHFFFAOYSA-N propyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCC BEKZXQKGTDVSKX-UHFFFAOYSA-N 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000006285 cell suspension Substances 0.000 description 3
- 239000013068 control sample Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- 241000510928 Erysiphe necator Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
- 102100040678 Programmed cell death protein 1 Human genes 0.000 description 2
- 101710089372 Programmed cell death protein 1 Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- AAQFSZFQCXLMNT-ACMTZBLWSA-N (3s)-3-amino-4-[[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid;hydrochloride Chemical compound Cl.OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 AAQFSZFQCXLMNT-ACMTZBLWSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- YSMODUONRAFBET-UHFFFAOYSA-N 5-hydroxylysine Chemical group NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000526200 Cacopsylla pyri Species 0.000 description 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- 241000721179 Clarias Species 0.000 description 1
- 241000228437 Cochliobolus Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 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 1
- 101150081532 KLK8 gene Proteins 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 241001067945 Pyritis Species 0.000 description 1
- 101100409194 Rattus norvegicus Ppargc1b gene Proteins 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241001544321 Thanatephorus cucumeris Species 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229960003369 butacaine Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229940067592 ethyl palmitate Drugs 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 229910052806 inorganic carbonate Inorganic materials 0.000 description 1
- 229910052909 inorganic silicate Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 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
- QGVNJRROSLYGKF-UHFFFAOYSA-N thiobarbital Chemical compound CCC1(CC)C(=O)NC(=S)NC1=O QGVNJRROSLYGKF-UHFFFAOYSA-N 0.000 description 1
- 108010021724 tonin Proteins 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—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)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US279595P | 1995-08-25 | 1995-08-25 | |
| US60/002,795 | 1995-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2183621A1 true CA2183621A1 (en) | 1997-02-26 |
Family
ID=21702546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002183621A Abandoned CA2183621A1 (en) | 1995-08-25 | 1996-08-19 | Compositions having synergistic fungitoxic effects |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5741793A (enExample) |
| EP (1) | EP0760208B1 (enExample) |
| JP (1) | JPH09110611A (enExample) |
| CN (1) | CN1071090C (enExample) |
| AR (1) | AR003978A1 (enExample) |
| AU (1) | AU723064B2 (enExample) |
| BR (1) | BR9603512A (enExample) |
| CA (1) | CA2183621A1 (enExample) |
| DE (1) | DE69613060T2 (enExample) |
| ES (1) | ES2156980T3 (enExample) |
| HU (1) | HUP9602323A3 (enExample) |
| IL (1) | IL119070A0 (enExample) |
| MX (1) | MX9603588A (enExample) |
| TW (1) | TW335334B (enExample) |
| ZA (1) | ZA966964B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5855654A (en) * | 1997-01-30 | 1999-01-05 | Rohm And Haas Company | Pyridazinones as marine antifouling agents |
| CA2317778A1 (en) | 1999-09-29 | 2001-03-29 | Vivienne E. Harris | Synergistic insecticidal formulations of pyridaben and strobilurins |
| WO2001022817A1 (en) * | 1999-09-29 | 2001-04-05 | Basf Corporation | Pyridaben compounds for fungicidal uses |
| JP2005519895A (ja) * | 2002-01-18 | 2005-07-07 | ファルマシア・コーポレーション | Ｐ３８阻害剤としての置換ピリダジノン |
| US20040157803A1 (en) * | 2002-03-04 | 2004-08-12 | Williams Deryck J. | Nematicidal fatty acid and fatty acid ester related compounds |
| US6887900B2 (en) | 2002-03-04 | 2005-05-03 | Divergence, Inc. | Nematicidal compositions and methods |
| US20050095663A1 (en) * | 2002-06-17 | 2005-05-05 | Young David H. | Process for screening fungitoxic compounds |
| ITMI20030210A1 (it) * | 2003-02-07 | 2004-08-08 | Res & Innovation Soc Coop A R L | Composti endocannabinoido-simili e loro impiego |
| US7368629B2 (en) * | 2004-02-04 | 2008-05-06 | Divergence, Inc. | Nucleic acids encoding anthelmintic agents and plants made therefrom |
| PT1928454E (pt) | 2005-05-10 | 2014-12-04 | Intermune Inc | Derivativos da piridona para modulação do sistema de proteína quinase ativada pelo stress |
| FR2928070A1 (fr) * | 2008-02-27 | 2009-09-04 | Sumitomo Chemical Co | Composition agricole, utilisation d'un compose pour sa production et procede pour matriser ou prevenir les maladies des plantes. |
| MX2010010950A (es) | 2008-04-08 | 2010-11-12 | Dow Agrosciences Llc | 2-alquinil-6-piridin-2-il-piridazinonas, 2-alquinil-6-piridin-2-il -dihidropiridazinonas, 2-alquinil-6-pirimidin-2-il-piridazinonas y 2-alquinil-6-pirimidin-2-il-dihidropiridazinonas y su uso como fungicidas. |
| US8304413B2 (en) | 2008-06-03 | 2012-11-06 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| MX2014015156A (es) | 2012-06-12 | 2015-08-06 | Abbvie Inc | Derivados de piridinona y piridazinona. |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| KR102373700B1 (ko) | 2014-04-02 | 2022-03-11 | 인터뮨, 인크. | 항섬유성 피리디논 |
| CA3017740A1 (en) | 2016-03-16 | 2017-09-21 | Pearlie BURNETTE | Small molecules against cereblon to enhance effector t cell function |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3033449C3 (de) * | 1980-09-05 | 1990-01-04 | Messerschmitt Boelkow Blohm | Zweistufiger scherenstromabnehmer |
| JPS5826802A (ja) * | 1981-08-10 | 1983-02-17 | Sankyo Co Ltd | 農園芸用殺菌剤 |
| WO1988008054A1 (en) * | 1987-04-10 | 1988-10-20 | Domenico Domenighetti | Road paver-finisher with a combination of axles with steering wheels and crawler units |
| ATE180475T1 (de) * | 1990-09-21 | 1999-06-15 | Rohm & Haas | Dihydropyridazinone und pyridazinone als fungizide |
| US5366995A (en) * | 1991-05-01 | 1994-11-22 | Mycogen Corporation | Fatty acid based compositions for the control of established plant infections |
-
1996
- 1996-08-12 AR ARP960103962A patent/AR003978A1/es unknown
- 1996-08-12 AU AU62015/96A patent/AU723064B2/en not_active Ceased
- 1996-08-13 US US08/696,284 patent/US5741793A/en not_active Expired - Fee Related
- 1996-08-14 IL IL11907096A patent/IL119070A0/xx unknown
- 1996-08-19 EP EP96306033A patent/EP0760208B1/en not_active Expired - Lifetime
- 1996-08-19 ES ES96306033T patent/ES2156980T3/es not_active Expired - Lifetime
- 1996-08-19 CA CA002183621A patent/CA2183621A1/en not_active Abandoned
- 1996-08-19 DE DE69613060T patent/DE69613060T2/de not_active Expired - Fee Related
- 1996-08-22 BR BR9603512A patent/BR9603512A/pt not_active Application Discontinuation
- 1996-08-22 MX MX9603588A patent/MX9603588A/es not_active IP Right Cessation
- 1996-08-23 CN CN96109457A patent/CN1071090C/zh not_active Expired - Fee Related
- 1996-08-23 HU HU9602323A patent/HUP9602323A3/hu unknown
- 1996-08-23 JP JP8241168A patent/JPH09110611A/ja active Pending
- 1996-08-25 ZA ZA9606964A patent/ZA966964B/xx unknown
- 1996-09-03 TW TW085110708A patent/TW335334B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| ES2156980T3 (es) | 2001-08-01 |
| CN1146282A (zh) | 1997-04-02 |
| CN1071090C (zh) | 2001-09-19 |
| ZA966964B (en) | 1997-02-19 |
| EP0760208B1 (en) | 2001-05-30 |
| HU9602323D0 (en) | 1996-10-28 |
| MX9603588A (es) | 1997-06-28 |
| DE69613060T2 (de) | 2001-10-25 |
| DE69613060D1 (de) | 2001-07-05 |
| TW335334B (en) | 1998-07-01 |
| JPH09110611A (ja) | 1997-04-28 |
| HUP9602323A3 (en) | 1999-03-01 |
| HUP9602323A2 (en) | 1997-05-28 |
| IL119070A0 (en) | 1996-11-14 |
| AU723064B2 (en) | 2000-08-17 |
| US5741793A (en) | 1998-04-21 |
| EP0760208A2 (en) | 1997-03-05 |
| AR003978A1 (es) | 1998-09-30 |
| AU6201596A (en) | 1997-02-27 |
| EP0760208A3 (en) | 1997-12-03 |
| BR9603512A (pt) | 1998-05-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20000821 |