JPH10500943A - 置換された芳香族チオカルボン酸アミド類及びその除草剤としての使用 - Google Patents
置換された芳香族チオカルボン酸アミド類及びその除草剤としての使用Info
- Publication number
- JPH10500943A JPH10500943A JP7528627A JP52862795A JPH10500943A JP H10500943 A JPH10500943 A JP H10500943A JP 7528627 A JP7528627 A JP 7528627A JP 52862795 A JP52862795 A JP 52862795A JP H10500943 A JPH10500943 A JP H10500943A
- Authority
- JP
- Japan
- Prior art keywords
- group
- case
- alkyl
- diyl
- 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
- -1 aromatic thiocarboxylic acid Chemical class 0.000 title claims abstract description 206
- 239000004009 herbicide Substances 0.000 title abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 7
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims description 40
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229910052801 chlorine Inorganic materials 0.000 claims description 36
- 239000011737 fluorine Substances 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 31
- 241000196324 Embryophyta Species 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000011593 sulfur Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 8
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 241001024304 Mino Species 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000005112 cycloalkylalkoxy 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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 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
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 241001553014 Myrsine salicina Species 0.000 claims description 3
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 3
- 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 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 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 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical group 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 231100000331 toxic Toxicity 0.000 claims description 3
- 230000002588 toxic effect Effects 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- HMZJBKATTSGEKP-UHFFFAOYSA-N FC(=O)OC#N Chemical compound FC(=O)OC#N HMZJBKATTSGEKP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 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
- 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
- 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
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000003205 fragrance Substances 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 239000004067 bulking agent Substances 0.000 claims 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical group C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 claims 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical group C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 claims 1
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 244000062793 Sorghum vulgare Species 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- 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
- 241000207763 Solanum Species 0.000 description 4
- 235000002634 Solanum Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-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
- 239000012074 organic phase Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002420 orchard Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229940086542 triethylamine Drugs 0.000 description 3
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- KGKGSIUWJCAFPX-UHFFFAOYSA-N 2,6-dichlorothiobenzamide Chemical compound NC(=S)C1=C(Cl)C=CC=C1Cl KGKGSIUWJCAFPX-UHFFFAOYSA-N 0.000 description 2
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 description 2
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
- 241000234282 Allium Species 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
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- 229910052742 iron Inorganic materials 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
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- 229940067606 lecithin Drugs 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
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- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
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- QKWLAUAUUGXSSE-UHFFFAOYSA-L prohexadione-calcium Chemical compound [Ca+2].CCC(=O)C1=C([O-])CC(C([O-])=O)CC1=O QKWLAUAUUGXSSE-UHFFFAOYSA-L 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
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- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
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- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 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
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-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
- 150000003918 triazines Chemical class 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-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
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
- C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
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- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/90—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.一般式(I) 式中、R1は水素またはハロゲンを表わし、 R2は基−A1−A2−A3を表わし、ここに A1は単結合を表わすか、或いは酸素、硫黄、−SO−、−SO2−、−CO −または基−N−A4を表わし、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、アルキルスルホニルまたはアリ ールスルホニルを表わし、 A1は更に各々の場合に随時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 はアレンジイルを表わし、 A2は単結合を表わすか、或いは酸素、硫黄、−SO−、−SO2−、−CO −または基−N−A4−を表わし、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、アリール、アルコキシ、アルキルスルホニルまたはア リールスルホニルを表わし、 A2は更に各々の場合に随時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 はアレンジイルを表わし、 A3は水素、ヒドロキシル、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、ハロゲンを表わすか、或いは各々の場合に随時置換 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、ジアルコキシ(チオ)ホスホリル、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、アルキニルオキシカルボニル、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、シク ロアルキルアルコキシカルボニル、アリール、アリールオキシ、アリールアルキ ル、アリールアルコキシ、アリールオキシカルボニル、アリールアルコキシカル ボニル、複素環、複素環式アルキル、複素環式アルコキシまたは複素環式アルコ キシカルボニルを表わし、 R3は水素またはハロゲンを表わすか、或いはR2と一緒になって随時最初( もしくは末端)または炭化水素鎖内に酸素原子、硫黄原子、SO2基、NH基、 N−アルキル基、カルボニル基及び/またはチオカルボニル基を含んでいてもよ いアルカンジイルまたはアルケンジイル基を表わし、そして Zは各々の場合に随時置換されていてもよい単環式または二環式の、飽和も しくは不飽和の複素環、複素環式アミノまたは複素環式イミノを表わす、 の置換された芳香族チオカルボキシアミド。 2.R1が水素、フッ素、塩素または臭素を表わし、 R2が基−A1−A2−A3を表わし、ここに A1が単結合を表わすか、或いは酸素、硫黄、−SO−、−SO2−、−CO− または基−N−A4−を表わし、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−アルキルスルホニルまたはフェニルスルホニルを表わし 、 A1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 −アルカンジイル、C2〜C6−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 ニレンを表わし、 A2が単結合を表わすか、或いは酸素、硫黄、−SO−、−SO2−、−CO− または基−N−A4−を表わし、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−アルキルスルホニルまたはフェニルスルホニルを表わし 、 A2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 −アルカンジイル、C2〜C6−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 ニレンを表わし、 A3が水素、ヒドロキシル、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、ハロゲンを表わすか、各々の場合にアルキル基中に炭素原子1〜6個を有 する各々の場合に随時ハロゲンまたは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 表わすか、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基中に炭素 原子2〜6個を有する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わすか、各々の場合にシクロアルキル基中に炭素 原子3〜6個及び随時アルキル基中に炭素原子1〜4個を有する各々の場合に随 時ハロゲン、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 シカルボニルを表わすか、各々の場合に随時ニトロ、シアノ、カルボキシル、ハ ロゲン、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、(各々の場合に随時全 体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−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、オキサゾリル−C1〜C4−アルキル、イソキサゾール−C1〜 C4−アルキル、チアゾール−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 メトキシを表わすか、或いはパーヒドロピラニルメトキシまたはピリジメトキシ を表わし、 R3が水素、フッ素、塩素または臭素を表わすか、或いはR2と一緒になって随 時最初(もしくは末端)または炭化水素鎖内に酸素原子、硫黄原子、SO2基、 NH基、N−C1〜C4−アルキル基、カルボニル基及び/またはチオカルボニル 基を含んでいてもよい各々の場合に炭素原子4個までを有するアルカンジイルま たはアルケンジイル基を表わし、そして Zが各々の場合に炭素原子2〜6個及び複素環式環系中に窒素原子1〜4個を 有し、随時更に酸素原子または硫黄原子及び/または随時−CO−、−CS−、 −SO−及び/またはSO2−の群からの3個までの基を含んでいてもよく、か つ随時ニトロ、ヒドロキシル、アミノ、シアノ、カルボキシル、カルバモイル、 チオカルバモイル、ハロゲン、C1〜C6−アルキル(随時ハロゲンまたはC1〜 C4−アルコキシで置換されていてもよい)、C2〜C6−アルケニルまたはC2〜 C6−アルキニル(各々の場合に随時ハロゲンで置換されていてもよい)、C1〜 C6−アルコキシまたはC1〜C6−アルコキシ−カルボニル(各々の場合に随時 ハロゲンまたはC1〜C4−アルコキシで置換されていてもよい)、C2〜C6−ア ルケニルオキシまたはC2〜C6−アルキニルオキシ(各々の場合に随時ハロゲン で置換されていてもよい)、C1〜C6−アルキルチ オ、C2〜C6−アルケニルチオまたはC2〜C6−アルキニルチオ(各々の場合に 随時ハロゲンで置換されていてもよい)、C1〜C6−アルキルアミノまたはジ− (C1〜C4−アルキル)−アミノ、C3〜C6−シクロアルキルまたはC3〜C6− シクロアルキル−C1〜C4−アルキル(各々の場合に随時ハロゲン及び/または C1〜C4−アルキルで置換されていてもよい)、フェニル、フェノキシ、フェニ ルチオ、フェニルスルフィニル、フェニルスルホニルまたはフェニルアミノ(各 々の場合に随時ニトロ、シアノ、ハロゲン、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)の 群からの基1個またはそれ以上で置換されていてもよい各々の場合に単環式また は二環式の、飽和もしくは不飽和の複素環、複素環式アミノまたは複素環式イミ ノを表わすことを特徴とする、請求の範囲第1項記載の一般式(I)の置換され た芳香族チオカルボキシアミド。 3.R1が水素、フッ素または塩素を表わし、 R2が基−A1−A2−A3を表わし、ここに A1が単結合を表わすか、或いは酸素、硫黄、−SO−、−SO2−、−CO− または基−N−A4−を表わし、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わし、 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−ジイルを表わし、 A2が単結合を表わすか、或いは酸素、硫黄、−SO−、−SO2−、−CO− または基−N−A4−を表わし、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、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わし、 A2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− ジイルを表わし、 A3が水素、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、臭素を表わすか、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 表わすか、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わすか、各々の場合に随時フッ素、塩素 、シアノ、カルボキシ−、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 わすか、或いは各々の場合に随時ニトロ、シアノ、カルボキシ、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、ベンジルオキシカルボニル、(各々の場合に随時完全または部分的に水 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、オキサゾリルメチル 、イソキサゾールメチル、チアゾルメチル、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わし、 R3が水素、フッ素または塩素を表わすか、或いはR2と一緒になって随時最初( もしくは末端)または炭化水素鎖中に酸素原子、硫黄原子、NH基、N−メチル 基、カルボニル基及び/またはチオカルボニル基を含んでいてもよい各々の場合 に炭素原子1〜3個を有するアルカンジイルまたはアルケンジイル基を表わし、 そして Zが各々の場合に炭素原子2〜5個及び複素環式環系中に窒素原子1〜3個を 有し、随時加えて酸素原子または硫黄原子及び/または−CO−、−CS−、− SO−及び/またはSO2−の群からの2個までの基を含んでいてもよく、かつ 随時ニトロ、ヒドロキシル、アミノ、シアノ、カルボキシル、カルバモイル、チ オカルバモイル、フッ素、塩素、臭素;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(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);プロペニル、ブテニル、プロピニルまた はブチニル (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);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 、メトキシカルボニルまたはエトキシカルボニル(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);プロペニルオキシ、ブ テニルオキシ、プロピニルオキシまたはブチニルオキシ(随時フッ素または塩素 で置換されていてもよい);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、プロペニルチオ、ブテニル チオ、プロピニルチオまたはブチニルチオ(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);メチルアミノ、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、ジメチルアミノまたはジエチルア ミノ;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(各々の場合に随時フッ素、塩素、メチル、エチル、n−もしくは i−プロピルで置換されていてもよい)、フェニル、フェノキシ、フェニルチオ 、フェニルスルフィニル、フェニルスルホニルまたはフェニルアミノ(各々の場 合に随時ニトロ、シアノ、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ま たはエトキシカルボニルで置換されていてもよい)の群からの基1個またはそれ 以上で置換されていてもよい各々の場合に単環式または二環式の、飽和もしくは 不飽和の複素環、複素環式アミノまたは複素環式イミノを表わすことを特徴とす る、請求の範囲第1項記載の 一般式(I)の置換された芳香族チオカルボキシアミド。 4.一般式(I) 式中、R1、R2、R3及びZは請求の範囲第1項記載の意味を有する、 の置換された芳香族チオカルボキシアミドを製造する際に、一般式(II) 式中、R1、R2、R3及びZは上記の意味を有する、 の置換された芳香族ニトリルを随時反応補助剤の存在下及び随時希釈剤の存在下 で硫化水素(H2S)またはチオアセトアミドと反応させることを特徴とする、 一般式(I)の置換された芳香族チオカルボキシアミドの製造方法。 5.請求の範囲第1〜4項のいずれかに記載の一般式(I)の置換された芳香 族チオカルボキシアミドを望ましくない植物及び/またはその生育地上に作用さ せることを特徴とする、望ましくない植物の防除方法。 6.望ましくない植物を防除するための請求の範囲第1〜4項のいずれかに記 載の一般式(I)の置換された芳香族チオカルボキシアミドの使用。 7.請求の範囲第1〜4項のいずれかに記載の一般式(I)の置換された芳香 族チオカルボキシアミドを増量剤及び/または表面活性剤と混合することを特徴 とする、除草剤組成物の製造方法。 8.少なくとも1つの請求の範囲第1〜4項のいずれかに記載の一般式(I) の置換された芳香族チオカルボキシアミドを含むことを特徴とする、除草剤組成 物。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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DE4415655 | 1994-05-04 | ||
DE4415655.3 | 1995-01-10 | ||
DE19500439A DE19500439A1 (de) | 1994-05-04 | 1995-01-10 | Substituierte aromatische Thiocarbonsäureamide |
DE19500439.6 | 1995-01-10 | ||
PCT/EP1995/001507 WO1995030661A1 (de) | 1994-05-04 | 1995-04-21 | Substituierte aromatische thiocarbonsäureamide und ihre verwendung als herbizide |
Publications (2)
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JPH10500943A true JPH10500943A (ja) | 1998-01-27 |
JP4039684B2 JP4039684B2 (ja) | 2008-01-30 |
Family
ID=25936253
Family Applications (1)
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JP52862795A Expired - Fee Related JP4039684B2 (ja) | 1994-05-04 | 1995-04-21 | 置換された芳香族チオカルボン酸アミド類及びその除草剤としての使用 |
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US (4) | US6077813A (ja) |
EP (1) | EP0758324B1 (ja) |
JP (1) | JP4039684B2 (ja) |
CN (1) | CN1113875C (ja) |
BR (1) | BR9507598A (ja) |
ES (1) | ES2238679T3 (ja) |
HK (1) | HK1000888A1 (ja) |
MX (1) | MX9605270A (ja) |
PL (1) | PL182505B1 (ja) |
PT (1) | PT758324E (ja) |
RU (1) | RU2144029C1 (ja) |
WO (1) | WO1995030661A1 (ja) |
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-
1995
- 1995-04-21 EP EP95917347A patent/EP0758324B1/de not_active Expired - Lifetime
- 1995-04-21 MX MX9605270A patent/MX9605270A/es not_active IP Right Cessation
- 1995-04-21 WO PCT/EP1995/001507 patent/WO1995030661A1/de active IP Right Grant
- 1995-04-21 CN CN95193953A patent/CN1113875C/zh not_active Expired - Fee Related
- 1995-04-21 RU RU96123303A patent/RU2144029C1/ru not_active IP Right Cessation
- 1995-04-21 JP JP52862795A patent/JP4039684B2/ja not_active Expired - Fee Related
- 1995-04-21 PL PL95317122A patent/PL182505B1/pl unknown
- 1995-04-21 US US08/732,257 patent/US6077813A/en not_active Expired - Fee Related
- 1995-04-21 ES ES95917347T patent/ES2238679T3/es not_active Expired - Lifetime
- 1995-04-21 BR BR9507598A patent/BR9507598A/pt not_active IP Right Cessation
- 1995-04-21 PT PT95917347T patent/PT758324E/pt unknown
-
1997
- 1997-12-22 HK HK97102543A patent/HK1000888A1/xx not_active IP Right Cessation
-
1999
- 1999-12-22 US US09/470,583 patent/US6331507B1/en not_active Ceased
-
2001
- 2001-09-04 US US09/945,855 patent/US6420316B1/en not_active Expired - Fee Related
- 2001-09-25 US US09/962,778 patent/US6451736B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
PL317122A1 (en) | 1997-03-17 |
AU693889B2 (en) | 1998-07-09 |
MX9605270A (es) | 1997-10-31 |
PT758324E (pt) | 2005-07-29 |
RU2144029C1 (ru) | 2000-01-10 |
EP0758324A1 (de) | 1997-02-19 |
BR9507598A (pt) | 1997-10-07 |
AU2345495A (en) | 1995-11-29 |
US6077813A (en) | 2000-06-20 |
WO1995030661A1 (de) | 1995-11-16 |
CN1113875C (zh) | 2003-07-09 |
US6331507B1 (en) | 2001-12-18 |
JP4039684B2 (ja) | 2008-01-30 |
ES2238679T3 (es) | 2005-09-01 |
CN1155282A (zh) | 1997-07-23 |
HK1000888A1 (en) | 2004-04-02 |
PL182505B1 (pl) | 2002-01-31 |
US6420316B1 (en) | 2002-07-16 |
US6451736B1 (en) | 2002-09-17 |
EP0758324B1 (de) | 2005-03-16 |
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