JPH10510283A - 除草特性を有する3−アリール−1,2,4−トリアゾール誘導体 - Google Patents
除草特性を有する3−アリール−1,2,4−トリアゾール誘導体Info
- Publication number
- JPH10510283A JPH10510283A JP8518213A JP51821396A JPH10510283A JP H10510283 A JPH10510283 A JP H10510283A JP 8518213 A JP8518213 A JP 8518213A JP 51821396 A JP51821396 A JP 51821396A JP H10510283 A JPH10510283 A JP H10510283A
- Authority
- JP
- Japan
- Prior art keywords
- case
- alkyl
- chlorine
- cyano
- fluorine
- 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.)
- Granted
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000004009 herbicide Substances 0.000 claims abstract description 7
- -1 Fluoromethylphenyl Chemical group 0.000 claims description 341
- 239000000460 chlorine Substances 0.000 claims description 103
- 229910052801 chlorine Inorganic materials 0.000 claims description 96
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 94
- 229910052731 fluorine Inorganic materials 0.000 claims description 85
- 239000011737 fluorine Substances 0.000 claims description 85
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 75
- 239000001257 hydrogen Substances 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 150000002367 halogens Chemical class 0.000 claims description 52
- 150000002431 hydrogen Chemical class 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 37
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 37
- 229910052794 bromium Inorganic materials 0.000 claims description 37
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
- 239000001301 oxygen Substances 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 239000011593 sulfur Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 239000003085 diluting agent Substances 0.000 claims description 13
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 8
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 8
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 7
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000005108 alkenylthio group Chemical group 0.000 claims description 6
- 125000005109 alkynylthio group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl 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
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 4
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 3
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000003566 oxetanyl group Chemical group 0.000 claims description 3
- 239000006187 pill Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- SIHDPKAXUCHRDH-UHFFFAOYSA-N (sulfanylamino)urea Chemical group NC(=O)NNS SIHDPKAXUCHRDH-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims description 2
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims description 2
- GDYZNHOFMUCVJO-UHFFFAOYSA-N [C-]#[N+]SOC#N Chemical compound [C-]#[N+]SOC#N GDYZNHOFMUCVJO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000006437 ethyl cyclopropyl group Chemical group 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000000286 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 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical group C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 claims description 2
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 2
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 3
- QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 claims 3
- 241001024304 Mino Species 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000006550 alkoxycarbonyl aryl group Chemical group 0.000 claims 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 1
- 238000007336 electrophilic substitution reaction Methods 0.000 claims 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000007858 starting material Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 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 7
- 244000062793 Sorghum vulgare Species 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 241000219318 Amaranthus Species 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 241000208296 Datura Species 0.000 description 3
- 241000209219 Hordeum Species 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 241000131091 Lucanus cervus Species 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
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- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
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- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000005486 sulfidation Methods 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
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- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
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- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.化合物4−(3,4−ジクロロフェニル)−1,2−ジメチル−5−チオキ ソ−1,2,4−トリアゾリジン−3−オン及び4−(4−クロロ−3−トリフ ルオロメチルフェニル)−1,2−ジメチル−5−チオキソ−1,2,4−トリ アゾリジン−3−オンを除く一般式(I) 式中、Q1は酸素または硫黄を表し、 Q2は酸素または硫黄を表し、 R1は水素、シアノまたはホルミルを表すか、或いは随時ハロゲン、シアノ 、カルボキシル、アルコキシ、アルケニルオキシ、アルキニルオキシ、アルキル チオ、アルケニルチオ、アルキニルチオ、アルコキシカルボニル、アルケニルオ キシカルボニルまたはアルキニルオキシカルボニルで置換されていてもよいアル キルを表し、 R1は更に各々の場合に随時ハロゲンで置換されていてもよいアルケニルま たはアルキニルを表し、 R1は更に各々の場合に随時ハロゲンで置換されていてもよいアルキルカル ボニル、アルケニルカルボニル、アルキニルカルボニル、アルコキシカルボニル 、アルケニルオキシカルボニルまたはアルキニルオキシカルボニルを表し、 R1は更に各々の場合に随時ハロゲン、シアノまたはカルボキシルで置換さ れていてもよいシクロアルキルまたはシクロアルキルカル ボニルを表し、 R2は水素、シアノまたはホルミルを表すか、或いは随時ハロゲン、シアノ 、カルボキシル、アルコキシ、アルケニルオキシ、アルキニルオキシ、アルキル チオ、アルケニルチオ、アルキニルチオ、アルコキシカルボニル、アルケニルオ キシカルボニルまたはアルキニルオキシカルボニルで置換されていてもよいアル キルを表し、 R2は更に各々の場合に随時ハロゲンで置換されていてもよいアルケニルま たはアルキニルを表し、 R2は更に各々の場合に随時ハロゲンで置換されていてもよいアルキルカル ボニル、アルケニルカルボニル、アルキニルカルボニル、アルコキシカルボニル 、アルケニルオキシカルボニルまたはアルキニルオキシカルボニルを表し、 R2は更に各々の場合に随時ハロゲン、シアノまたはカルボキシルで置換さ れていてもよいシクロアルキルまたはシクロアルキルカルボニルを表し、そして Arは下記 に定義される置換された一環式または二環式のアリールまたはヘテロアリー ルを表し、ここに R3は水素またはハロゲンを表し、 R4は水素またはハロゲンを表し、 R5はシアノ、カルボキシル、クロロカルボニル、カルバモイル、チオカル バモイル、ヒドロキシルまたはハロゲンを表すか、或いは各々の場合に随時ハロ ゲンで置換されていてもよいアルキル、アルコキシまたはアルコキシカルボニル を表し、 R6は次の基 −A1−A2−A3 を表し、ここに A1は単結合を表すか、或いは酸素、硫黄、−SO−、−SO2−、−CO− または基−N−A4を表し、ここにA4は水素、ヒドロキシル、アルキル、アルケ ニル、アルキニル、アルコキシ、アリール、アルキルカルボニル、アリールカル ボニル、アルキルスルホニルまたはアリールスルホニルを表し、 A1は更に各々の場合に随時ハロゲンで置換されていてもよいアルカンジイ ル、アルケンジイル、アザアルケンジイル、アルキンジイル、シクロアルカンジ イル、シクロアルケンジイルまたはフェニレンを表し、 A2は単結合を表すか、或いは酸素、硫黄、−SO−、−SO2−、−CO− または基−N−A4を表し、ここにA4は水素、ヒドロキシル、アルキル、アルコ キシ、アリール、アルキルスルホニルまたはアリールスルホニルを表し、 A2は更に各々の場合に随時ハロゲンで置換されていてもよいアルカンジイ ル、アルケンジイル、アザアルケンジイル、アルキンジイル、シクロアルカンジ イル、シクロアルケンジイルまたはフェニレンを表し、 A3は水素を表し、ただし各々の場合にA1及び/またはA2はいずれの単結 合も表さず、 A3は更にヒドロキシル、メルカプト、アミノ、シアノ、イソシアノ、チオ シアナト、ニトロ、カルボキシル、カルバモイル、チオカルバモイル、スルホ、 クロロスルホニルまたはハロゲンを表すか、或いは各々の場合に随時ハロゲンま たはアルコキシで置換されていてもよいアルキル、アルコキシ、アルキルチオ、 アルキルスルフィニル、アルキルスルホニル、アルキルアミノ、ジアルキルアミ ノ、アルコキシカルボニルまたはジアルコキシ(チオ)ホスホリルを表し、 A3は更に各々の場合に随時ハロゲンで置換されていてもよいアルケニル、 アルケニルオキシ、アルケニルチオ、アルケニルアミノ、アルキリデンアミノ、 アルケニルオキシカルボニル、アルキニル、アルキニルオキシ、アルキニルチオ 、アルキニルアミノまたはアルキニルオキシカルボニルを表し、 A3は更に各々の場合に随時ハロゲン、シアノ、カルボキシル、アルキル及 び/またはアルコキシ−カルボニルで置換されていてもよいシクロアルキル、シ クロアルキルオキシ、シクロアルキルアルキル、シクロアルキルアルコキシ、シ クロアルキリデンアミノ、シクロアルキルオキシカルボニルまたはシクロアルキ ルアルコキシカルボニルを表し、 A3は更に各々の場合に随時ニトロ、シアノ、カルボキシル、ハロゲン、ア ルキル、ハロゲノアルキル、アルキルオキシ、ハロゲンアルキルオキシ及び/ま たはアルコキシ−カルボニルで置換されてい てもよいアリール、アリールオキシ、アラルキル、アリールアルコキシ、アリー ルオキシカルボニルまたはアリールアルコキシカルボニルを表し、 A3は更に各々の場合に随時完全にか、または部分的に水素化されていても よいピロリル、ピラゾリル、イミダゾリル、トリアゾリル、フリル、オキシラニ ル、オキセタニル、ジオキソラニル、チエニル、オキサゾリル、イソキサゾリル 、チアゾリル、イソチアゾリル、オキサジアゾリル、チアジアゾリル、ピリジニ ル、ピリミジニル、トリアジニル、ピラゾリルアルキル、フリルアルキル、チエ ニルアルキル、オキサゾリルアルキル、イソキサゾリルアルキル、チアゾリルア ルキル、ピリジニルアルキル、ピリミジニルアルキル、ピラゾリルアルキルまた はフリルアルコキシを表すか、或いはパーヒドロピラニルアルコキシまたはピリ ジルアルコキシを表し、そして R7は水素またはハロゲンを表すか、或いは 各々の場合に2個の隣接する基−R3及びR4、R4及びR5、R5及びR6また はR6及びR7は一緒になって次の基 の1つを表し、ここに Q3、Q4及びQ5は同一もしくは相異なり、かつ各々の場合に酸素及び硫黄 を表し、 R8及びR9は同一もしくは相異なり、かつ個々に水素、ハロゲンまたはアル キルを表すか、或いは一緒になってアルカンジイルを表し、 そして R10は水素またはヒドロキシルを表すか、随時シアノ、ハロゲン、アルコキ シ、アルキルカルボニルまたはアルコキシ−カルボニルで置換されていてもよい アルキル、アルキルカルボニル、アルコキシカルボニルまたはアルキルスルホニ ルを表すか、各々の場合に随時ハロゲンで置換されていてもよいアルケニルまた はアルキニルを表すか、各々の場合に随時ハロゲンまたはアルキルで置換されて いてもよいシクロアルキルまたはシクロアルキルアルキルを表すか、各々の場合 に随時ハロゲンで置換されていてもよいアルコキシまたはアルケニルオキシを表 すか、或いは各々の場合に随時シアノ、ハロゲン、アルキル、ハロゲノアルキル 、アルコキシまたはハロゲノアルコキシで置換されていてもよいアリールアルキ ルまたはアリールアルコキシを表す、 の置換されたN−アリール含窒素複素環式化合物。 2.一般式(Ia) 式中、Q1、Q2、R1、R2及びArは請求の範囲第1項記載の意味を有する 、 の置換されたN−アリール含窒素複素環式化合物。 3.一般式(Ib) 式中、Q1、Q2、R1、R2及びArは請求の範囲第1項記載の意味を有する 、 の置換されたN−アリール含窒素複素環式化合物。 4.(a)一般式(II) 式中、Q1、Q2、R1、R2及びArは請求の範囲第1項記載の意味を有し、 そして Rはアルキルを表す、 の(チオ)セミカルバジド誘導体を適当ならば反応補助剤の存在下及び適当なら ば希釈剤の存在下で環化縮合反応させ、その後、適当ならば親電子または求核置 換反応を置換基の定義に関連する常法で行うか、或い は (b)一般式(III) 式中、Q1、Q2、R1、R2及びArは上記の意味を有する、 のアリールイミノ複素環式化合物、或いは式(Ia)または(Ib)の化合物を 適当ならば反応補助剤の存在下及び適当ならば希釈剤の存在下で熱的に(「熱分 解的に」)異性化する工程からなる、特許請求の範囲第1項〜第3項のいずれか に記載の一般式(I)の置換されたN−アリール含窒素複素環式化合物或いは一 般式(Ia)または(Ib)の化合物の製造方法。 5.化合物4−(3,4−ジクロロフェニル)−1,2−ジメチル−5−チオキ ソ−1,2,4−トリアゾリジン−3−オン及び4−(4−クロロ−3−トリフ ルオロメチルフェニル)−1,2−ジメチル−5−チオキソ−1,2,4−トリ アゾリジン−3−オンを除き、 Q1が酸素または硫黄を表し、 Q2が酸素または硫黄を表し、 R1が水素、シアノまたはホルミルを表すか、或いは各々の場合に随時フッ素 、塩素、シアノ、カルボキシル、C1〜C4−アルコキシ、C3〜C4−アルケニル オキシ、C3〜C4−アルキニルオキシ、C1〜C4−アルキルチオ、C3〜C4−ア ルケニルチオ、C3〜C4−アルキニルチオ、C1〜C4−アルコキシ−カルボニル 、C3〜C4−アルケニルオキシ−カルボニルまたはC3〜C4−アルキニル−カル ボニルで置換されていても よいC1〜C6−アルキルを表し、 R1が更に各々の場合に随時フッ素または塩素で置換されていてもよいC3〜C6 −アルケニルまたはC3〜C6−アルキニルを表し、 R1が更に各々の場合に随時フッ素または塩素で置換されていてもよいC1〜C6 −アルキル−カルボニル、C3〜C6−アルケニル−カルボニル、C3〜C6−ア ルキニル−カルボニル、C1〜C6−アルコキシ−カルボニル、C3〜C6−アルケ ニルオキシ−カルボニルまたはC3〜C6−アルキニルオキシ−カルボニルを表し 、 R1が更に各々の場合に随時フッ素、塩素、臭素、シアノまたはカルボキシル で置換されていてもよいC3〜C6−シクロアルキルまたはC3〜C6−シクロアル キル−カルボニルを表し、 R2が水素、シアノまたはホルミルを表すか、或いは各々の場合に随時フッ素 、塩素、シアノ、カルボキシル、C1〜C4−アルコキシ、C3〜C4−アルケニル オキシ、C3〜C4−アルキニルオキシ、C1〜C4−アルキルチオ、C3〜C4−ア ルケニルチオ、C3〜C4−アルキニルチオ、C1〜C4−アルコキシ−カルボニル 、C3〜C4−アルケニルオキシ−カルボニルまたはC3〜C4−アルキニルオキシ −カルボニルで置換されていてもよいC1〜C6−アルキルを表し、 R2が更に各々の場合に随時フッ素または塩素で置換されていてもよいC3〜C6 −アルケニルまたはC3〜C6−アルキニルを表し、 R2が更に各々の場合に随時フッ素または塩素で置換されていてもよいC1〜C6 −アルキル−カルボニル、C3〜C6−アルケニル−カルボニル、C3〜C6−ア ルキニル−カルボニル、C1〜C6−アルコキシ−カルボニル、C3〜C6−アルケ ニルオキシ−カルボニルまたはC3〜C6−ア ルキニルオキシ−カルボニルを表し、 R2が更に各々の場合に随時フッ素、塩素、臭素、シアノまたはカルボキシル で置換されていてもよいC3〜C6−シクロアルキルまたはC3〜C6−シクロアル キル−カルボニルを表し、 Arが下記 に定義される置換された一環式または二環式アリール或いはヘテロアリール基を 表し、ここに R3が水素、フッ素、塩素または臭素を表し、 R4が水素、フッ素、塩素または臭素を表し、 R5がシアノ、カルボキシル、クロロカルボニル、カルバモイル、チオカルバ モイル、ヒドロキシル、フッ素、塩素、臭素を表すか、或いは各々の場合に炭素 原子4個までを有し、かつ各々の場合に随時フッ素及び/または塩素で置換され ていてもよいアルキル、アルコキシまたはアルコキシカルボニルを表し、 R6が次の基 −A1−A2−A3 を表し、ここに A1が単結合を表すか、或いは酸素、硫黄、−SO−、−SO2−、−CO−ま たは基−N−A4を表し、ここにA4が水素、ヒドロキシル、C1〜C4−アルキル 、C3〜C4−アルケニル、C3〜C4−アルキニル、 C1〜C4−アルコキシ、フェニル、C1〜C4−アルキル−カルボニル、フェニル −カルボニル、C1〜C4−アルキル−スルホニルまたはフェニルスルホニルを表 し、 A1が更に各々の場合に随時フッ素、塩素または臭素で置換されていてもよい C1〜C6−アルカンジイル、C2〜C6−アルケンジイル、C2〜C6−アザアルケ ンジイル、C2〜C6−アルキンジイル、C3〜C6−シクロアルカンジイル、C3 〜C6−シクロアルケンジイルまたはフェニレンを表し、 A2が単結合を表すか、或いは酸素、硫黄、−SO−、−SO2−、−CO−ま たは基−N−A4を表し、ここにA4が水素、ヒドロキシル、C1〜C4−アルキル 、C1〜C4−アルコキシ、フェニルまたはC1〜C4−アルキル−スルホニルまた はフェニルスルホニルを表し、 A2が更に各々の場合に随時フッ素、塩素または臭素で置換されていてもよい C1〜C6−アルカンジイル、C2〜C6−アルケンジイル、C2〜C6−アザアルケ ンジイル、C2〜C6−アルキンジイル、C3〜C6−シクロアルカンジイル、C3 〜C6−シクロアルケンジイルまたはフェニレンを表し、 A3は水素を表し、ただし各々の場合にA1及び/またはA2はいずれの単結合 も表さず、 A3がヒドロキシル、メルカプト、アミノ、シアノ、イソシアノ、チオシアナ ト、ニトロ、カルボキシル、カルバモイル、チオカルバモイル、スルホ、クロロ スルホニル、フッ素、塩素または臭素を表し、 A3が更に各々の場合にアルキル基中に炭素原子1〜6個を有し、かつ各々の 場合に随時フッ素、塩素またはC1〜C4−アルコキシで置換さ れていてもよいアルキル、アルコキシ、アルキルチオ、アルキルスルフィニル、 アルキルスルホニル、アルキルアミノ、ジアルキルアミノ、アルコキシカルボニ ルまたはジアルコキシ(チオ)ホスホリルを表し、 A3が更に各々の場合にアルケニル、アルキリデンまたはアルキニル中に炭素 原子2〜6個を有し、かつ各々の場合に随時フッ素または塩素で置換されていて もよいアルケニル、アルケニルオキシ、アルケニルアミノ、アルキリデンアミノ 、アルケニルオキシカルボニル、アルキニル、アルキニルオキシ、アルキニルア ミノまたはアルキニルオキシカルボニルを表し、 A3が更に各々の場合にシクロアルキル基中に炭素原子3〜6個及び適当なら ばアルキル基中に炭素原子1〜4個を有し、かつ各々の場合に随時フッ素、塩素 、シアノ、カルボキシル、C1〜C4−アルキル及び/またはC1〜C4−アルコキ シ−カルボニルで置換されていてもよいシクロアルキル、シクロアルキルオキシ 、シクロアルキルアルキル、シクロアルキルアルコキシ、シクロアルキリデンア ミノ、シクロアルキルオキシカルボニルまたはシクロアルキルアルコキシカルボ ニルを表し、 A3が更に各々の場合に随時ニトロ、シアノ、カルボキシル、フッ素、塩素、 臭素、C1〜C4−アルキル、C1〜C4−ハロゲノアルキル、C1〜C4−アルキル オキシ、C1〜C4−ハロゲノアルキルオキシ及び/またはC1〜C4−アルコキシ −カルボニルで置換されていてもよいフェニル、フェニルオキシ、フェニル−C1 〜C4−アルキル、フェニル−C1〜C4−アルコキシ、フェニルオキシカルボニ ルまたはフェニル−C1〜C4−アルコキシカルボニルを表し、 A3が更に各々の場合に完全にか、または部分的に水素化されていて もよいピロリル、ピラゾリル、イミダゾリル、トリアゾリル、フリル、オキシラ ニル、オキセタニル、ジオキソラニル、チエニル、オキサゾリル、イソキサゾリ ル、チアゾリル、イソチアゾリル、オキサジアゾリル、チアジアゾリル、ピリジ ニル、ピリミジニル、トリアジニル、ピラゾリル−C1〜C4−アルキル、フリル −C1〜C4−アルキル、チエニル−C1〜C4−アルキル、オキサロリル−C1〜 C4−アルキル、イソキサゾリル−C1〜C4−アルキル、チアゾリル−C1〜C4 −アルキル、ピリジニル−C1〜C4−アルキル、ピリミジニル−C1〜C4−アル キル、ピラゾリルメトキシまたはフリルメトキシを表すか、或いはパーヒドロピ ラニルメトキシまたはピリジルメトキシを表し、そして R7が水素、フッ素または塩素を表すか、 各々の場合に2個の隣接する基−R3及びR4、R4及びR5、R5及びR6または R6及びR7が一緒になって次の基 の1つを表し、ここに Q3、Q4及びQ5は同一もしくは相異なり、かつ各々の場合に酸素または硫黄 を表し、 R8及びR9が同一もしくは相異なり、かつ個々に酸素、フッ素、塩素、 臭素またはC1〜C4−アルキルを表すか、或いは一緒になってC2〜C5−アルカ ンジイルを表し、そして R10が水素またはヒドロキシルを表すか、或いは各々の場合にアルキル基中に 炭素原子1〜6個を有し、かつ各々の場合に随時シアノ、フッ素、塩素、C1〜 C4−アルコキシ、C1〜C4−アルキル−カルボニルまたはC1〜C4−アルコキ シ−カルボニルで置換されていてもよいアルキル、アルキルカルボニル、アルコ キシカルボニルまたはアルキルスルホニルを表し、 R10が更に各々の場合に炭素原子2〜6個を有し、かつ各々の場合に随時フッ 素、塩素または臭素で置換されていてもよいアルケニルまたはアルキニルを表し 、 R10が更にシクロアルキル基中に炭素原子3〜6個及び適当ならばアルキル基 中に炭素原子1〜3個を有し、かつ各々の場合に随時フッ素、塩素、臭素または C1〜C4−アルキルで置換されていてもよいシクロアルキルまたはシクロアルキ ルアルキルを表し、 R10が更に各々の場合に炭素原子6個までを有し、かつ各々の場合に随時フッ 素及び/または塩素で置換されていてもよいアルコキシまたはアルケニルオキシ を表し、 R10が更に各々の場合に随時シアノ、フッ素、塩素、C1〜C4−アルキル、C1 〜C4−ハロゲノアルキル、C1〜C4−アルコキシまたはC1〜C4−ハロゲノア ルコキシで置換されていてもよいベンジルまたはベンジルオキシを表す、請求の 範囲第1〜3項のいずれかに記載の一般式(I)、(Ia)または(Ib)の置 換されたN−アリール含窒素複素環式化合物。 6.化合物4−(3,4−ジクロロフェニル)−1,2−ジメチル−5−チオキ ソ−1,2,4−トリアゾリジン−3−オン及び4−(4−クロロ−3−トリフ ルオロメチルフェニル)−1,2−ジメチル−5−チオキソ−1,2,4−トリ アゾリジン−3−オンを除き、 Q1が酸素または硫黄を表し、 Q2が酸素または硫黄を表し、 R1が水素、シアノまたはホルミルを表すか、或いは各々の場合に随時フッ素 、塩素、シアノ、カルボキシル、メトキシまたはエトキシで置換されていてもよ いメチル、エチル、n−もしくはi−プロピル、またはn−、i−、s−もしく はt−ブチルを表し、 R1が更に各々の場合に随時フッ素または塩素で置換されていてもよいプロペ ニル、ブテニル、プロピニルまたはブチニルを表し、 R1が更に各々の場合に随時フッ素または塩素で置換されていてもよいアセチ ル、プロピオニル、メトキシカルボニルまたはエトキシカルボニルを表し、 R1が更に随時フッ素または塩素で置換されていてもよいシクロプロピルを表 し、 R2が水素、シアノまたはホルミルを表すか、或いは各々の場合に随時フッ素 、塩素、シアノ、カルボキシル、メトキシまたはエトキシで置換されていてもよ いメチル、エチル、n−もしくはi−プロピル、またはn−、i−、s−もしく はt−ブチルを表し、 R2が更に各々の場合に随時フッ素または塩素で置換されていてもよいプロペ ニル、ブテニル、プロピニルまたはブチニルを表し、 R2が更に各々の場合に随時フッ素または塩素で置換されていてもよ いアセチル、プロピオニル、メトキシカルボニルまたはエトキシカルボニルを表 し、 R2が更に随時フッ素または塩素で置換されていてもよいシクロプロピルを表 し、 Arが下記 に定義される置換された一環式または二環式アリール或いはヘテロアリール基を 表し、ここに R3が水素、フッ素または塩素を表し、 R4が水素、フッ素または塩素を表し、 R5シアノ、チオカルバモイル、塩素、臭素、メチル、トリフルオロメチル、 メトキシ、ジフルオロメトキシまたはトリフルオロメトキシを表し、 R6が次の基 −A1−A2−A3 を表し、ここに A1が単結合を表すか、或いは酸素、硫黄、−SO−、−SO2−、−CO−ま たは基−N−A4を表し、ここにA4が水素、ヒドロキシル、メチル、エチル、n −もしくはi−プロピル、メトキシ、エトキシ、n−もしくはi−プロポキシ、 メチルスルホニルまたはエチルスルホニルを表し、 A1が更にメチレン、エタン−1,1−ジイル、エタン−1,2−ジイル、プ ロパン−1,1−ジイル、プロパン−1,2−ジイル、プロパン−1,3−ジイ ル、エテン−1,2−ジイル、プロペン−1,2−ジイル、プロペン−1,3− ジイル、エチン−1,2−ジイル、プロピン−1,2−ジイルまたはプロピン− 1,3−ジイルを表し、 A2が単結合を表すか、或いは酸素、硫黄、−SO−、−SO2−、−CO−ま たは基−N−A4を表し、ここにA4が酸素、ヒドロキシル、メチル、エチル、n −もしくはi−プロピル、メトキシ、エトキシ、n−もしくはi−プロポキシ、 メチルスルホニル、エチルスルホニル、n−もしくはi−プロピルスルホニルま たはフェニルスルホニルを表し、 A1が更にメチレン、エタン−1,1−ジイル、エタン−1,2−ジイル、プ ロパン−1,1−ジイル、プロパン−1,2−ジイル、プロパン−1,3−ジイ ル、エテン−1,2−ジイル、プロペン−1,2−ジイル、プロペン−1,3− ジイル、エチン−1,2−ジイル、プロピン−1,2−ジイルまたはプロピン− 1,3−ジイルを表し、 A3が水素を表し、但し、各々の場合にA1及び/またはA2は単結合を表さず 、 A3が更にヒドロキシル、アミノ、シアノ、ニトロ、カルボキシル、カルバモ イル、スルホ、フッ素、塩素または臭素を表し、 A3が更に各々の場合に随時フッ素、塩素、メトキシまたはエトキシで置換さ れていてもよいメチル、エチル、n−もしくはi−プロピル、n−、i−、s− もしくはt−ブチル、n−、i−、s−もしくはt−ペンチル、メトキシ、エト キシ、n−もしくはi−プロポキシ、n−、i−、s−もしくはt−ブトキシ、 n−、i−、s−もしくはt−ペン チルオキシメチルチオ、エチルチオ、n−もしくはi−プロピルチオ、n−、i −、s−もしくはt−ブチルチオ、メチルスルフィニル、エチルスルフィニル、 n−もしくはi−プロピルスルフィニル、メチルスルホニル、エチルスルホニル 、n−もしくはi−プロピルスルホニル、メチルアミノ、エチルアミノ、n−も しくはi−プロピルアミノ、n−、i−、s−もしくはt−ブチルアミノ、ジメ チルアミノ、ジエチルアミノ、メトキシカルボニル、エトキシカルボニル、n− もしくはi−プロポキシカルボニル、ジメトキシホスホリル、ジエトキシホスホ リル、ジプロポキシホスホリルまたはジイソプロポキシホスホリルを表し、 A3が各々の場合に随時フッ素または塩素で置換されていてもよいプロペニル 、ブテニル、プロペニルオキシ、ブテニルオキシ、プロペニルアミノ、ブテニル アミノ、プロピリデンアミノ、ブチリデンアミノ、プロペニルオキシカルボニル 、ブテニルオキシカルボニル、プロピニル、ブチニル、プロピニルオキシ、ブチ ニルオキシ、プロピニルアミノ、ブチニルアミノ、プロピニルオキシカルボニル またはブチニルオキシカルボニルを表し、 A3が更に各々の場合に随時フッ素、塩素、シアノ、カルボキシル、メチル、 エチル、n−もしくはi−プロピル、メトキシカルボニルまたはエトキシカルボ ニルで置換されていてもよいシクロプロピル、シクロブチル、シクロペンチル、 シクロヘキシル、シクロプロピルオキシ、シクロブチルオキシ、シクロペンチル オキシ、シクロヘキシルオキシ、シクロプロピルメチル、シクロブチルメチル、 シクロペンチルメチル、シクロヘキシルメチル、シクロプロピルメトキシ、シク ロブチルメトキシ、シクロペンチルメトキシ、シクロヘキシルメトキシ、シクロ ペンチリデ ンアミノ、シクロヘキシリデンアミノ、シクロペンチルオキシカルボニル、シク ロヘキシルオキシカルボニル、シクロペンチルメトキシカルボニルまたはシクロ ヘキシルメトキシカルボニルを表し、 A3が更に各々の場合に随時ニトロ、シアノ、カルボキシル、フッ素、塩素、 臭素、メチル、エチル、n−もしくはi−プロピル、トリフルオロメチル、メト キシ、エトキシ、n−もしくはi−プロポキシ、ジフルオロメトキシ、トリフル オロメトキシ、メトキシカルボニル及び/またはエトキシカルボニルで置換され ていてもよいフェニル、フェニルオキシ、ベンジル、フェニルエチル、ベンジル オキシ、フェニルオキシカルボニルまたはベンジルオキシカルボニルを表し、 A3が更に各々の場合に完全にか、または部分的に水素化されていてもよいピ ロリル、ピラゾリル、イミダゾリル、トリアゾリル、フリル、チエニル、オキサ ゾリル、イソキサゾリル、チアゾリル、イソチアゾリル、オキサジアゾリル、チ アジアゾリル、ピリジニル、ピリミジニル、トリアジニル、ピラゾリルメチル、 フリルメチル、チエニルメチル、オキサロリルメチル、イソキサゾリルメチル、 チアゾリルメチル、ピリジニルメチル、ピリミジニルメチル、ピラゾリルメトキ シ、フリルメトキシまたはピリジルメトキシを表し、 R7が水素、フッ素または塩素を表すか、或いは 各々の場合に2個の隣接する基−R3及びR4、R4及びR5、R5及びR6または R6及びR7が一緒になって次の基 の1つを表し、ここに Q3、Q4及びQ5は同一もしくは相異なり、かつ各々の場合に酸素または硫黄 を表し、 R8及びR9が同一もしくは相異なり、かつ個々に水素、フッ素、塩素、メチル またはエチルを表すか、或いは一緒になってエタン−1,2−ジイル(ジメチレ ン)を表し、そして R10が水素またはヒドロキシルを表すか、或いは随時シアノ、フッ素、塩素、 メトキシ、エトキシ、アセチル、プロピオニル、メトキシカルボニルまたはエト キシカルボニルで置換されていてもよいメチル、エチル、n−もしくはi−プロ ピルまたはn−、i−、s−もしくはt−ブチルを表し、 R10が更に各々の場合に随時フッ素、塩素または臭素で置換されていてもよい プロペニル、ブテニル、プロピニルまたはブチニルを表し、 R10が更に各々の場合に随時フッ素、塩素、臭素、メチルまたはエチルで置換 されていてもよいシクロプロピル、シクロブチル、シクロペンチル、シクロヘキ シル、シクロプロピルメチル、シクロブチルメチル、シクロペンチルメチルまた はシクロヘキシルメチルを表し、 R10が更に各々の場合に随時フッ素及び/または塩素で置換されていてもよい メトキシ、エトキシ、n−もしくはi−プロポキシ、n−、i −もしくはs−ブトキシ、プロペニルオキシまたはブテニルオキシを表し、そし て R10が更に各々の場合に随時シアノ、フッ素、塩素、メチル、エチル、トリフ ルオロメチル、メトキシ、エトキシ、ジフルオロメチルまたはトリフルオロメト キシで置換されていてもよいベンジルまたはベンジルオキシを表す、請求の範囲 第1〜3項のいずれかに記載の一般式(I)、(Ia)または(Ib)の置換さ れたN−アリール含窒素複素環式化合物。 7.少なくとも1つの請求の範囲第1〜6項のいずれかに記載の一般式(I)、 (Ia)または(Ib)のN−アリール含窒素複素環式化合物を含有する除草剤 組成物。 8.請求の範囲第1〜6項のいずれかに記載の一般式(I)、(Ia)または( Ib)のN−アリール含窒素複素環式化合物を望ましくない植物及び/またはそ の環境上に作用させることからなる、望ましくない植物の防除方法。 9.望ましくない植物を防除するための請求の範囲第1〜6項のいずれかに記載 の一般式(I)、(Ia)または(Ib)のN−アリール含窒素複素環式化合物 の使用。 10.請求の範囲第1〜6項のいずれかに記載の一般式(I)、(Ia)または (Ib)のN−アリール含窒素複素環式化合物を増量剤及び/または表面活性物 質と混合することからなる、除草剤組成物の製造方法。
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DE4444741 | 1994-12-15 | ||
DE4444741.8 | 1995-08-24 | ||
DE19531152.3 | 1995-08-24 | ||
DE19531152A DE19531152A1 (de) | 1994-12-15 | 1995-08-24 | Substituierte N-Aryl-Stickstoffheterocyclen |
PCT/EP1995/004759 WO1996018618A1 (de) | 1994-12-15 | 1995-12-04 | 3-aryl-1,2,4-triazolderivate mit herbiziden eigenschaften |
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JP4157161B2 JP4157161B2 (ja) | 2008-09-24 |
Family
ID=25942887
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP51821396A Expired - Fee Related JP4157161B2 (ja) | 1994-12-15 | 1995-12-04 | 除草特性を有する3−アリール−1,2,4−トリアゾール誘導体 |
JP2007035233A Withdrawn JP2007131646A (ja) | 1994-12-15 | 2007-02-15 | 除草特性を有する3−アリール−1,2,4−トリアゾール誘導体 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007035233A Withdrawn JP2007131646A (ja) | 1994-12-15 | 2007-02-15 | 除草特性を有する3−アリール−1,2,4−トリアゾール誘導体 |
Country Status (11)
Country | Link |
---|---|
US (4) | US6162765A (ja) |
EP (2) | EP0797573B1 (ja) |
JP (2) | JP4157161B2 (ja) |
CN (2) | CN1171879C (ja) |
AU (1) | AU4340296A (ja) |
BR (1) | BR9510028A (ja) |
CA (1) | CA2207628C (ja) |
DE (3) | DE19531152A1 (ja) |
ES (2) | ES2228691T3 (ja) |
HK (1) | HK1008992A1 (ja) |
WO (1) | WO1996018618A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011526251A (ja) * | 2008-07-03 | 2011-10-06 | ニューラクソン,インコーポレーテッド | Nos阻害活性を有するベンゾオキサジン類、ベンゾチアジン類、および関係化合物 |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19531152A1 (de) * | 1994-12-15 | 1996-06-20 | Bayer Ag | Substituierte N-Aryl-Stickstoffheterocyclen |
DE19627901A1 (de) * | 1996-07-11 | 1998-01-15 | Bayer Ag | Substituierte aromatische Carbonylverbindungen und ihre Derivate |
DE19708928A1 (de) * | 1997-03-05 | 1998-09-10 | Bayer Ag | Substituierte aromatische Aminoverbindungen |
DE19937772A1 (de) | 1999-08-10 | 2001-02-15 | Bayer Ag | Substituierte Heterocyclyl-2GH-chromene |
US7741485B2 (en) * | 2003-04-08 | 2010-06-22 | Basf Aktiengesellschaft | Benzenesulphonamide derivatives as herbicides or desiccant/defoliant compounds |
US7972867B2 (en) | 2005-04-06 | 2011-07-05 | Quest Diagnostics Investments Incorporated | Methods for detecting vitamin D metabolites by mass spectrometry |
US7745226B2 (en) | 2005-04-06 | 2010-06-29 | Quest Diagnostics Investments Incorporated | Methods for detecting vitamin D metabolites |
US7972868B2 (en) | 2007-11-28 | 2011-07-05 | Quest Diagnostics Investments Incorporated | Methods for detecting dihydroxyvitamin D metabolites by mass spectrometry |
US7977117B2 (en) | 2009-12-03 | 2011-07-12 | Quest Diagnostics Investments Incorprated | Vitamin D metabolite determination utilizing mass spectrometry following derivatization |
US8034627B2 (en) | 2009-12-03 | 2011-10-11 | Quest Diagnostics Investments Incorporated | Methods for detecting dihydroxyvitamin D metabolites by mass spectrometry |
CN102812356B (zh) | 2009-12-11 | 2017-08-08 | 奎斯特诊断投资公司 | 多重样品中的甾族化合物的质谱法 |
CA2783797C (en) | 2009-12-11 | 2021-06-08 | Quest Diagnostics Investments Incorporated | Mass spectrometric determination of non-derivatized, non-metabolized vitamin d |
CN103221409B (zh) | 2010-10-01 | 2016-03-09 | 巴斯夫欧洲公司 | 除草的苯并*嗪酮类 |
PL2688885T3 (pl) * | 2011-03-22 | 2016-12-30 | Amidy kwasu N-(1,3,4-oksdiazol-2-ilo)arylokarboksylowego i ich zastosowanie jako herbicydów | |
CN104072430B (zh) * | 2014-07-23 | 2017-09-29 | 西华师范大学 | 多取代的1,2,4‑三唑烷衍生物制备方法 |
AU2018373436C1 (en) | 2017-11-23 | 2023-10-19 | Basf Se | Herbicidal pyridylethers |
CN111356693A (zh) | 2017-11-23 | 2020-06-30 | 巴斯夫欧洲公司 | 除草的苯基醚类 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL43060A (en) * | 1972-09-01 | 1976-06-30 | Ciba Geigy Ag | 2-phenyl-5alpha,6,6alpha,7-tetrahydro-5,7-etheno-1h,5h-cyclopropa(d)(1,2,4)triazolo(1,2-alpha)pyridazine-1,3(2h)-diones,their manufacture and pesticidal compositions containing them |
US4087534A (en) * | 1974-05-22 | 1978-05-02 | David Ovadia | N-haloalkylmio urazole pesticides |
JPS5318571A (en) * | 1976-08-03 | 1978-02-20 | Mitsubishi Chem Ind Ltd | Urazole derivatives and fungicides containing same for agriculture and horticulture |
US4276420A (en) * | 1978-05-24 | 1981-06-30 | Chevron Research Company | Herbicidal and plant-growth-regulating 1,2,4-trisubstituted-1,2,4-triazolidin-3-one-5-thione |
EP0011693A1 (de) * | 1978-10-03 | 1980-06-11 | Ciba-Geigy Ag | Neue N-(trifluormethansulfonylaminophenyl)-substituierte N-Heterocyclen, ihre Herstellung, sie enthaltende Mittel und ihre Verwendung zur Beeinflussung des Pflanzenwachstums |
US4326878A (en) * | 1979-02-09 | 1982-04-27 | Chevron Research | Herbicidal and plant-growth-regulating 1,2,4-trisubstituted-1,2,4-triazolidin-3,5-dithiones |
US4290651A (en) | 1979-04-03 | 1981-09-22 | Dresser Industries, Inc. | Surface mining method |
GB2063855B (en) * | 1979-11-20 | 1983-07-20 | Chevron Res | Triazolidine derivatives and process for preparing the same |
US4366320A (en) * | 1980-07-31 | 1982-12-28 | The Upjohn Company | 4-Substituted phenyl-1,2,4-triazoline-3,5-diones and their dihydro analogs as analytical reagents |
DE3268566D1 (en) * | 1981-09-19 | 1986-02-27 | Sumitomo Chemical Co | 4-(2-fluoro-4-halo-5-substituted phenyl)urazols, and their production and use |
US4789394A (en) * | 1985-07-24 | 1988-12-06 | Ciba-Geigy Corporation | Annularly-linked triazole compounds |
US5108486A (en) * | 1990-02-09 | 1992-04-28 | Kanagawa Chemical Laboratory, Ltd. | Herbicidal substituted-phenyl-1,2,4-triazol-5(1H)-thiones and -ones |
DE19531152A1 (de) * | 1994-12-15 | 1996-06-20 | Bayer Ag | Substituierte N-Aryl-Stickstoffheterocyclen |
-
1995
- 1995-08-24 DE DE19531152A patent/DE19531152A1/de not_active Withdrawn
- 1995-12-04 BR BR9510028A patent/BR9510028A/pt not_active IP Right Cessation
- 1995-12-04 CN CNB011197765A patent/CN1171879C/zh not_active Expired - Fee Related
- 1995-12-04 DE DE59510161T patent/DE59510161D1/de not_active Expired - Fee Related
- 1995-12-04 EP EP95942066A patent/EP0797573B1/de not_active Expired - Lifetime
- 1995-12-04 CN CN95197555A patent/CN1090623C/zh not_active Expired - Fee Related
- 1995-12-04 ES ES01110136T patent/ES2228691T3/es not_active Expired - Lifetime
- 1995-12-04 ES ES95942066T patent/ES2174973T3/es not_active Expired - Lifetime
- 1995-12-04 EP EP01110136A patent/EP1120411B1/de not_active Expired - Lifetime
- 1995-12-04 AU AU43402/96A patent/AU4340296A/en not_active Abandoned
- 1995-12-04 CA CA002207628A patent/CA2207628C/en not_active Expired - Fee Related
- 1995-12-04 DE DE59510947T patent/DE59510947D1/de not_active Expired - Fee Related
- 1995-12-04 WO PCT/EP1995/004759 patent/WO1996018618A1/de active IP Right Grant
- 1995-12-04 JP JP51821396A patent/JP4157161B2/ja not_active Expired - Fee Related
-
1998
- 1998-08-10 HK HK98109797A patent/HK1008992A1/xx not_active IP Right Cessation
-
1999
- 1999-02-05 US US09/245,818 patent/US6162765A/en not_active Expired - Fee Related
-
2000
- 2000-09-20 US US09/667,392 patent/US6426318B1/en not_active Expired - Fee Related
-
2002
- 2002-05-02 US US10/138,011 patent/US6743755B2/en not_active Expired - Fee Related
-
2003
- 2003-01-29 US US10/353,455 patent/US20030208073A1/en not_active Abandoned
-
2007
- 2007-02-15 JP JP2007035233A patent/JP2007131646A/ja not_active Withdrawn
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011526251A (ja) * | 2008-07-03 | 2011-10-06 | ニューラクソン,インコーポレーテッド | Nos阻害活性を有するベンゾオキサジン類、ベンゾチアジン類、および関係化合物 |
Also Published As
Publication number | Publication date |
---|---|
WO1996018618A1 (de) | 1996-06-20 |
JP2007131646A (ja) | 2007-05-31 |
BR9510028A (pt) | 1998-06-02 |
DE19531152A1 (de) | 1996-06-20 |
HK1008992A1 (en) | 1999-07-23 |
EP0797573B1 (de) | 2002-04-10 |
EP1120411B1 (de) | 2004-09-22 |
US6162765A (en) | 2000-12-19 |
JP4157161B2 (ja) | 2008-09-24 |
ES2174973T3 (es) | 2002-11-16 |
CA2207628C (en) | 2007-01-30 |
DE59510947D1 (de) | 2004-10-28 |
EP0797573A1 (de) | 1997-10-01 |
DE59510161D1 (de) | 2002-05-16 |
US20030144522A1 (en) | 2003-07-31 |
ES2228691T3 (es) | 2005-04-16 |
CN1325848A (zh) | 2001-12-12 |
CN1171879C (zh) | 2004-10-20 |
CA2207628A1 (en) | 1996-06-20 |
EP1120411A2 (de) | 2001-08-01 |
CN1090623C (zh) | 2002-09-11 |
US20030208073A1 (en) | 2003-11-06 |
US6743755B2 (en) | 2004-06-01 |
EP1120411A3 (de) | 2001-08-08 |
CN1175249A (zh) | 1998-03-04 |
AU4340296A (en) | 1996-07-03 |
US6426318B1 (en) | 2002-07-30 |
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