ZA200303005B - Substituted 4,5-dihydro-1,2,4-triazin-3-ones,1,2,4-triazin-3-ones, and their use as fungicides and insecticides. - Google Patents
Substituted 4,5-dihydro-1,2,4-triazin-3-ones,1,2,4-triazin-3-ones, and their use as fungicides and insecticides. Download PDFInfo
- Publication number
- ZA200303005B ZA200303005B ZA200303005A ZA200303005A ZA200303005B ZA 200303005 B ZA200303005 B ZA 200303005B ZA 200303005 A ZA200303005 A ZA 200303005A ZA 200303005 A ZA200303005 A ZA 200303005A ZA 200303005 B ZA200303005 B ZA 200303005B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- halo
- alkoxy
- substituted
- phenyl
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title abstract description 10
- 239000002917 insecticide Substances 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 284
- 125000005843 halogen group Chemical group 0.000 claims description 216
- -1 alkyicarbonyl Chemical group 0.000 claims description 120
- 125000003545 alkoxy group Chemical group 0.000 claims description 116
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 109
- 125000001424 substituent group Chemical group 0.000 claims description 89
- 125000004414 alkyl thio group Chemical group 0.000 claims description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
- 125000001188 haloalkyl group Chemical group 0.000 claims description 52
- 125000000304 alkynyl group Chemical group 0.000 claims description 43
- 125000001624 naphthyl group Chemical group 0.000 claims description 38
- 125000001544 thienyl group Chemical group 0.000 claims description 36
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 35
- 125000002541 furyl group Chemical group 0.000 claims description 35
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 32
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 28
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 19
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 18
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 18
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 18
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 17
- 125000004434 sulfur atom Chemical group 0.000 claims description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 15
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 14
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 13
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 13
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 12
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 12
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 12
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 241000233866 Fungi Species 0.000 claims description 8
- 241000238631 Hexapoda Species 0.000 claims description 8
- 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims description 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
- 230000000855 fungicidal effect Effects 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 7
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 7
- 230000000749 insecticidal effect Effects 0.000 claims description 7
- 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 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000001963 growth medium Substances 0.000 claims description 4
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- CBHJGZXYRXNQEZ-UHFFFAOYSA-N 2,3-dihydro-1h-triazin-4-one Chemical compound O=C1NNNC=C1 CBHJGZXYRXNQEZ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012039 electrophile Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000004475 heteroaralkyl group Chemical group 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 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
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([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
- NQCDUQZVHYUPEJ-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(Cl)=CC=C1C(=O)CN1C(=O)SCC1=O NQCDUQZVHYUPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 125000005109 alkynylthio group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005840 aryl keto group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000005164 aryl thioalkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004651 chloromethoxy group Chemical group ClCO* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000003452 oxalyl group Chemical group *C(=O)C(*)=O 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent 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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24380100P | 2000-10-27 | 2000-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200303005B true ZA200303005B (en) | 2004-04-16 |
Family
ID=22920183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200303005A ZA200303005B (en) | 2000-10-27 | 2003-04-16 | Substituted 4,5-dihydro-1,2,4-triazin-3-ones,1,2,4-triazin-3-ones, and their use as fungicides and insecticides. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6995157B2 (fr) |
| EP (1) | EP1328275B1 (fr) |
| JP (1) | JP2004517878A (fr) |
| KR (1) | KR100840883B1 (fr) |
| CN (1) | CN1199640C (fr) |
| AT (1) | ATE394105T1 (fr) |
| AU (1) | AU2002246814A1 (fr) |
| BR (1) | BR0114911A (fr) |
| CA (1) | CA2427134A1 (fr) |
| DE (1) | DE60133914D1 (fr) |
| DK (1) | DK1328275T3 (fr) |
| ES (1) | ES2301574T3 (fr) |
| IL (1) | IL155505A0 (fr) |
| MX (1) | MXPA03003707A (fr) |
| PL (1) | PL361936A1 (fr) |
| PT (1) | PT1328275E (fr) |
| WO (1) | WO2002056682A2 (fr) |
| ZA (1) | ZA200303005B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006119400A2 (fr) * | 2005-05-03 | 2006-11-09 | Dow Agrosciences Llc | 4,5-dihydro-1,2,4-triazin-6-ones, 1,2,4-trianzin-6-ones substituees et leur utilisation comme fongicides |
| US8178658B2 (en) * | 2008-02-12 | 2012-05-15 | Dow Agrosciences, Llc | Pesticidal compositions |
| JP6117825B2 (ja) * | 2012-02-02 | 2017-04-19 | ダウ アグロサイエンシィズ エルエルシー | 農薬組成物およびそれらに関する方法 |
| CN107266379B (zh) * | 2016-04-06 | 2020-09-18 | 南开大学 | 含有单脲桥结构三嗪酮衍生物及其制备方法和在杀虫、杀菌方面的应用 |
| CN109111406B (zh) * | 2018-10-24 | 2021-12-17 | 福州大学 | 全氟烷基或二氟甲基-1,2,4-三嗪酮化合物的合成方法 |
| AU2021207961B2 (en) | 2020-01-16 | 2024-09-19 | Qingdao Kingagroot Chemical Compound Co., Ltd. | Fused ring substituted aromatic compound and preparation method therefor, herbicidal composition, and use thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4616014A (en) * | 1981-10-22 | 1986-10-07 | Fujisawa Pharmaceutical Co., Ltd. | Triazine derivatives, and pharmaceutical compositions comprising the same |
| US4581356A (en) * | 1983-03-22 | 1986-04-08 | Fujisawa Pharmaceutical Co., Ltd. | Triazine derivatives, and pharmaceutical compositions comprising the same |
| ES2070861T3 (es) * | 1987-10-16 | 1995-06-16 | Ciba Geigy Ag | Compuestos antiparasitarios. |
| DE4239540A1 (de) | 1992-11-25 | 1994-05-26 | Asta Medica Ag | Neue heterocyclische Verbindungen mit antiasthmatischer/antiallergischer, entzündungshemmender, positiv inotroper und blutdrucksenkender Wirkung |
| US5994355A (en) * | 1993-10-15 | 1999-11-30 | Takeda Chemical Industries, Ltd. | 1, 2, 4-Triazin-3-one derivatives, production and use thereof |
| RU2146674C1 (ru) * | 1993-10-15 | 2000-03-20 | Такеда Кемикал Индастриз, Лтд. | Производные триазина, способы их получения, антипротозойная композиция, добавка в пищу животных, способ ингибирования протозои у животных |
| US6159980A (en) | 1996-09-16 | 2000-12-12 | Dupont Pharmaceuticals Company | Pyrazinones and triazinones and their derivatives thereof |
| US6825192B1 (en) | 1999-02-15 | 2004-11-30 | Eisai Co., Ltd. | Heterodiazinone derivatives |
-
2001
- 2001-10-26 DE DE60133914T patent/DE60133914D1/de not_active Expired - Lifetime
- 2001-10-26 ES ES01994420T patent/ES2301574T3/es not_active Expired - Lifetime
- 2001-10-26 PT PT01994420T patent/PT1328275E/pt unknown
- 2001-10-26 EP EP01994420A patent/EP1328275B1/fr not_active Expired - Lifetime
- 2001-10-26 AT AT01994420T patent/ATE394105T1/de not_active IP Right Cessation
- 2001-10-26 MX MXPA03003707A patent/MXPA03003707A/es active IP Right Grant
- 2001-10-26 WO PCT/US2001/050162 patent/WO2002056682A2/fr not_active Ceased
- 2001-10-26 DK DK01994420T patent/DK1328275T3/da active
- 2001-10-26 BR BR0114911-3A patent/BR0114911A/pt not_active Application Discontinuation
- 2001-10-26 CN CNB018178936A patent/CN1199640C/zh not_active Expired - Fee Related
- 2001-10-26 JP JP2002557201A patent/JP2004517878A/ja active Pending
- 2001-10-26 CA CA002427134A patent/CA2427134A1/fr not_active Abandoned
- 2001-10-26 IL IL15550501A patent/IL155505A0/xx unknown
- 2001-10-26 PL PL01361936A patent/PL361936A1/xx not_active Application Discontinuation
- 2001-10-26 AU AU2002246814A patent/AU2002246814A1/en not_active Abandoned
- 2001-10-26 US US10/399,924 patent/US6995157B2/en not_active Expired - Fee Related
- 2001-10-26 KR KR1020037005785A patent/KR100840883B1/ko not_active Expired - Fee Related
-
2003
- 2003-04-16 ZA ZA200303005A patent/ZA200303005B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL155505A0 (en) | 2003-11-23 |
| CN1199640C (zh) | 2005-05-04 |
| US20040019209A1 (en) | 2004-01-29 |
| KR20040004413A (ko) | 2004-01-13 |
| CN1474694A (zh) | 2004-02-11 |
| MXPA03003707A (es) | 2004-05-04 |
| BR0114911A (pt) | 2003-10-14 |
| PL361936A1 (en) | 2004-10-18 |
| DE60133914D1 (de) | 2008-06-19 |
| EP1328275B1 (fr) | 2008-05-07 |
| DK1328275T3 (da) | 2008-09-01 |
| AU2002246814A1 (en) | 2002-07-30 |
| ATE394105T1 (de) | 2008-05-15 |
| WO2002056682A2 (fr) | 2002-07-25 |
| ES2301574T3 (es) | 2008-07-01 |
| EP1328275A2 (fr) | 2003-07-23 |
| WO2002056682A3 (fr) | 2003-02-06 |
| PT1328275E (pt) | 2008-07-14 |
| EP1328275A4 (fr) | 2004-03-10 |
| JP2004517878A (ja) | 2004-06-17 |
| CA2427134A1 (fr) | 2002-07-25 |
| KR100840883B1 (ko) | 2008-06-24 |
| US6995157B2 (en) | 2006-02-07 |
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