UA73511C2 - Herbicide compounds, a method for the preparation thereof and intermediary compounds - Google Patents

Herbicide compounds, a method for the preparation thereof and intermediary compounds Download PDF

Info

Publication number: UA73511C2
Authority: UA; Ukraine
Prior art keywords: group; formula; compounds; halogen; salkyl
Prior art date: 1999-06-16

Application number

UA2002010432A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Syngenta Participations Ag

Priority date (The priority date 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 date listed.)

1999-06-16

Filing date

2000-06-14

Publication date

2005-08-15

2000-06-14 Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag

2005-08-15 Publication of UA73511C2 publication Critical patent/UA73511C2/uk

Links

150000001875 compounds Chemical class 0.000 title abstract description 103
238000000034 method Methods 0.000 title abstract description 26
238000002360 preparation method Methods 0.000 title abstract description 14
230000002363 herbicidal effect Effects 0.000 title 1
239000004009 herbicide Substances 0.000 title 1
238000006243 chemical reaction Methods 0.000 abstract description 35
229910052739 hydrogen Inorganic materials 0.000 abstract description 31
239000001257 hydrogen Substances 0.000 abstract description 30
150000003839 salts Chemical class 0.000 abstract description 12
239000002253 acid Substances 0.000 abstract description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 10
239000012039 electrophile Substances 0.000 abstract description 10
229910021645 metal ion Inorganic materials 0.000 abstract description 8
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 abstract description 7
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 abstract description 6
239000011230 binding agent Substances 0.000 abstract description 4
239000003054 catalyst Substances 0.000 abstract description 4
239000003960 organic solvent Substances 0.000 abstract description 4
239000007848 Bronsted acid Substances 0.000 abstract description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
238000011065 in-situ storage Methods 0.000 abstract 1
-1 mercapto, amino Chemical group 0.000 description 111
229910052736 halogen Inorganic materials 0.000 description 61
150000002367 halogens Chemical group 0.000 description 61
125000003277 amino group Chemical group 0.000 description 53
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 37
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 35
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
125000004093 cyano group Chemical group *C#N 0.000 description 25
150000002431 hydrogen Chemical class 0.000 description 24
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
229910052760 oxygen Inorganic materials 0.000 description 21
239000001301 oxygen Substances 0.000 description 21
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 20
229910052717 sulfur Inorganic materials 0.000 description 20
125000004432 carbon atom Chemical group C* 0.000 description 19
239000011593 sulfur Substances 0.000 description 19
125000003118 aryl group Chemical group 0.000 description 17
239000002585 base Substances 0.000 description 17
125000001424 substituent group Chemical group 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
239000000203 mixture Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
230000003993 interaction Effects 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 14
229920006395 saturated elastomer Polymers 0.000 description 14
229910052740 iodine Inorganic materials 0.000 description 13
239000000243 solution Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
229910052784 alkaline earth metal Inorganic materials 0.000 description 11
125000002947 alkylene group Chemical group 0.000 description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
125000005842 heteroatom Chemical group 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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 10
125000000217 alkyl group Chemical group 0.000 description 10
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
239000011734 sodium Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
239000008096 xylene Substances 0.000 description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
229910052794 bromium Inorganic materials 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
125000000623 heterocyclic group Chemical group 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
125000004450 alkenylene group Chemical group 0.000 description 8
125000001072 heteroaryl group Chemical group 0.000 description 8
125000003396 thiol group Chemical group [H]S* 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
238000010992 reflux Methods 0.000 description 7
WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
239000003513 alkali Substances 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
239000013078 crystal Substances 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
239000011737 fluorine Substances 0.000 description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
125000004414 alkyl thio group Chemical group 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
125000004433 nitrogen atom Chemical group N* 0.000 description 5
OTLYTKRAADUASA-UHFFFAOYSA-N oxadiazepane Chemical compound C1CCONNC1 OTLYTKRAADUASA-UHFFFAOYSA-N 0.000 description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
150000001342 alkaline earth metals Chemical class 0.000 description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
150000003863 ammonium salts Chemical class 0.000 description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 4
150000004649 carbonic acid derivatives Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
125000001188 haloalkyl group Chemical group 0.000 description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
229960003424 phenylacetic acid Drugs 0.000 description 4
239000003279 phenylacetic acid Substances 0.000 description 4
229910052698 phosphorus Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
125000006413 ring segment Chemical group 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
FBDJOPVHKPDKKU-UHFFFAOYSA-N 2-(2,4,6-trimethylphenyl)propanediamide Chemical compound CC1=CC(C)=C(C(C(N)=O)C(N)=O)C(C)=C1 FBDJOPVHKPDKKU-UHFFFAOYSA-N 0.000 description 3
GSRIWRWUJUFERJ-UHFFFAOYSA-N 2-(2,6-diethyl-4-methylphenyl)propanedioic acid Chemical compound CCC1=CC(C)=CC(CC)=C1C(C(O)=O)C(O)=O GSRIWRWUJUFERJ-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
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239000000370 acceptor Substances 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229940043279 diisopropylamine Drugs 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
239000011630 iodine Substances 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
229910052720 vanadium Inorganic materials 0.000 description 3
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical class CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
MBCOLUIVZSFWBX-UHFFFAOYSA-N 2-(2,6-diethyl-4-methylphenyl)propanediamide Chemical compound CCC1=CC(C)=CC(CC)=C1C(C(N)=O)C(N)=O MBCOLUIVZSFWBX-UHFFFAOYSA-N 0.000 description 2
ULSWMICHZPPOBA-UHFFFAOYSA-N 2-(2,6-diethyl-4-pyridin-4-ylphenyl)propanediamide Chemical compound CCC1=C(C(C(N)=O)C(N)=O)C(CC)=CC(C=2C=CN=CC=2)=C1 ULSWMICHZPPOBA-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
125000006040 2-hexenyl group Chemical group 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
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
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QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
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125000003342 alkenyl group Chemical group 0.000 description 2
125000003302 alkenyloxy group Chemical group 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
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238000009835 boiling Methods 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical class CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
238000001212 derivatisation Methods 0.000 description 2
150000001470 diamides Chemical class 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
150000004816 dichlorobenzenes Chemical class 0.000 description 2
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical class CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
125000006125 ethylsulfonyl group Chemical group 0.000 description 2
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
238000002955 isolation Methods 0.000 description 2
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125000006606 n-butoxy group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
DJUWKQYCYKRJNI-UHFFFAOYSA-N n-ethoxyaniline Chemical class CCONC1=CC=CC=C1 DJUWKQYCYKRJNI-UHFFFAOYSA-N 0.000 description 1
QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
IUZZLNVABCISOI-UHFFFAOYSA-N n-ethylheptan-1-amine Chemical compound CCCCCCCNCC IUZZLNVABCISOI-UHFFFAOYSA-N 0.000 description 1
SDQCOADWEMMSGK-UHFFFAOYSA-N n-ethyloctan-1-amine Chemical compound CCCCCCCCNCC SDQCOADWEMMSGK-UHFFFAOYSA-N 0.000 description 1
KLJUVCXLKBGKOY-UHFFFAOYSA-N n-hexylheptan-1-amine Chemical compound CCCCCCCNCCCCCC KLJUVCXLKBGKOY-UHFFFAOYSA-N 0.000 description 1
SKLXFEQHEBALKG-UHFFFAOYSA-N n-hexyloctan-1-amine Chemical compound CCCCCCCCNCCCCCC SKLXFEQHEBALKG-UHFFFAOYSA-N 0.000 description 1
NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical class CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
XJINZNWPEQMMBV-UHFFFAOYSA-N n-methylhexan-1-amine Chemical class CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
OZIXTIPURXIEMB-UHFFFAOYSA-N n-methylnonan-1-amine Chemical class CCCCCCCCCNC OZIXTIPURXIEMB-UHFFFAOYSA-N 0.000 description 1
SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 1
CNCBAEHAEKNSPZ-UHFFFAOYSA-N n-methylpentadecan-1-amine Chemical class CCCCCCCCCCCCCCCNC CNCBAEHAEKNSPZ-UHFFFAOYSA-N 0.000 description 1
JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
125000001326 naphthylalkyl group Chemical group 0.000 description 1
150000005002 naphthylamines Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical class CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical class CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical class CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
125000005920 sec-butoxy group Chemical group 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000003307 slaughter Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—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
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

UA2002010432A 1999-06-16 2000-06-14 Herbicide compounds, a method for the preparation thereof and intermediary compounds UA73511C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH112299		1999-06-16
PCT/EP2000/005476 WO2000078881A2 (en)	1999-06-16	2000-06-14	Process for the preparation of herbicidal derivatives

Publications (1)

Publication Number	Publication Date
UA73511C2 true UA73511C2 (en)	2005-08-15

Family

ID=4203010

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002010432A UA73511C2 (en)	1999-06-16	2000-06-14	Herbicide compounds, a method for the preparation thereof and intermediary compounds

Country Status (19)

Country	Link
US (2)	US6552187B1 (ja)
EP (1)	EP1183317B1 (ja)
JP (1)	JP4080743B2 (ja)
KR (1)	KR100752941B1 (ja)
CN (1)	CN1140528C (ja)
AR (1)	AR029166A1 (ja)
AT (1)	ATE250113T1 (ja)
AU (1)	AU765302B2 (ja)
BR (1)	BR0011702B1 (ja)
CA (1)	CA2374279C (ja)
DE (1)	DE60005338T2 (ja)
HU (1)	HU230021B1 (ja)
IL (2)	IL146579A0 (ja)
MX (1)	MXPA01012486A (ja)
PL (1)	PL201663B1 (ja)
RU (1)	RU2244715C2 (ja)
UA (1)	UA73511C2 (ja)
WO (1)	WO2000078881A2 (ja)
ZA (1)	ZA200110254B (ja)

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AU7514600A (en) *	1999-09-07	2001-04-10	Syngenta Participations Ag	Novel herbicides
JP2005516973A (ja) *	2002-01-22	2005-06-09	シンジェンタパーティシペーションズアクチェンゲゼルシャフト	除草剤として有用なフェニル置換ヘテロ環化合物
US7214825B2 (en) *	2003-10-17	2007-05-08	Honeywell International Inc.	O-(3-chloropropenyl) hydroxylamine free base
EA013842B1 (ru)	2005-02-09	2010-08-30	Зингента Партисипейшнс Аг	Способ получения промежуточных продуктов
CN101878592B (zh)	2007-12-28	2012-11-07	夏普株式会社	半导体装置和显示装置
JP5995445B2 (ja)	2009-03-12	2016-09-21	バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒＩｎｔｅｌｌｅｃｔｕａｌＰｒｏｐｅｒｔｙＧｍｂＨ	クロロ芳香族化合物及びブロモ芳香族化合物を調整する方法
AR087008A1 (es)	2011-06-22	2014-02-05	Syngenta Participations Ag	Derivados de n-oxi-pirazolo-triazepina-diona
CN108264463B (zh) *	2016-12-30	2021-04-09	浙江省诸暨合力化学对外贸易有限公司	一种制备2-芳基丙二酸衍生物的方法及其应用
CN108264517B (zh) *	2016-12-30	2019-12-03	浙江省诸暨合力化学对外贸易有限公司	一种制备唑啉草酯的方法及其中间体
EP3564208B1 (en) *	2016-12-30	2021-11-10	Oriental (Luzhou) Agrochemicals. Co., Ltd.	Method for preparing 2-(cyclohexenylene) malonic acid derivative and use thereof
CN106928253A (zh) *	2017-03-09	2017-07-07	武汉工程大学	一种唑啉草酯的制备方法
WO2018184196A1 (zh)	2017-04-07	2018-10-11	泸州东方农化有限公司	一种制备2-芳基丙二酰胺的方法及其应用
WO2019110613A1 (en)	2017-12-05	2019-06-13	Syngenta Participations Ag	Chemical process for the synthesis of herbicidal pyrazolidinedione compounds
CN116676009A (zh) *	2018-09-05	2023-09-01	阿比尔技术公司	用于保护性涂层的化合物和制剂
CN109232292A (zh) *	2018-09-11	2019-01-18	浙江中山化工集团股份有限公司	一种2,6-二乙基-4-甲基苯基丙二酰胺的制备方法
AU2019387370A1 (en)	2018-11-30	2021-06-10	Nuvation Bio Inc.	Pyrrole and pyrazole compounds and methods of use thereof
CN111372913B (zh)	2019-04-01	2021-09-03	泸州东方农化有限公司	一种制备2-芳基丙二酸衍生物的方法、中间体及其应用
CN111440192B (zh) *	2020-03-06	2022-11-25	山东华科化工有限公司	一种微通道制备唑啉草酯中间体的方法
US20240059707A1 (en) *	2020-12-11	2024-02-22	Gharda Chemicals Limited	Process for the preparation of pyrazole-oxadiazepine
US20240172753A1 (en)	2021-03-30	2024-05-30	Stepan Company	Agricultural formulations
CN115873019A (zh) *	2022-11-23	2023-03-31	利尔化学股份有限公司	一种唑啉草酯及其中间体的制备方法
CN116082155B (zh) *	2022-12-27	2024-07-16	上海工程技术大学	一种利用对称环氧化合物制备唑啉草酯中间体的方法

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US4884248A (en) *	1988-01-25	1989-11-28	Mobil Oil Corporation	Method of restoring seismic data
US5358924A (en)	1991-03-21	1994-10-25	Bayer Aktiengesellschaft	3-hydroxy-4-aryl-5-oxo-pyrozoline derivatives, compositions and use
DE69908568T2 (de) *	1998-03-13	2004-05-06	Syngenta Participations Ag	Herbizid aktive 3-hydroxy-4-aryl-5-oxopyrazolinderivate

2000
- 2000-06-14 RU RU2002100643/04A patent/RU2244715C2/ru active
- 2000-06-14 IL IL14657900A patent/IL146579A0/xx unknown
- 2000-06-14 CN CNB008089841A patent/CN1140528C/zh not_active Expired - Lifetime
- 2000-06-14 US US09/980,240 patent/US6552187B1/en not_active Expired - Lifetime
- 2000-06-14 JP JP2001505631A patent/JP4080743B2/ja not_active Expired - Lifetime
- 2000-06-14 WO PCT/EP2000/005476 patent/WO2000078881A2/en active IP Right Grant
- 2000-06-14 MX MXPA01012486A patent/MXPA01012486A/es active IP Right Grant
- 2000-06-14 AU AU56821/00A patent/AU765302B2/en not_active Expired
- 2000-06-14 AR ARP000102932A patent/AR029166A1/es active IP Right Grant
- 2000-06-14 EP EP00942071A patent/EP1183317B1/en not_active Expired - Lifetime
- 2000-06-14 UA UA2002010432A patent/UA73511C2/uk unknown
- 2000-06-14 KR KR1020017016032A patent/KR100752941B1/ko active IP Right Grant
- 2000-06-14 DE DE60005338T patent/DE60005338T2/de not_active Expired - Lifetime
- 2000-06-14 BR BRPI0011702-1A patent/BR0011702B1/pt not_active IP Right Cessation
- 2000-06-14 CA CA2374279A patent/CA2374279C/en not_active Expired - Lifetime
- 2000-06-14 AT AT00942071T patent/ATE250113T1/de active
- 2000-06-14 PL PL353184A patent/PL201663B1/pl unknown
- 2000-06-14 HU HU0201492A patent/HU230021B1/hu unknown
2001
- 2001-11-19 IL IL146579A patent/IL146579A/en not_active IP Right Cessation
- 2001-12-13 ZA ZA200110254A patent/ZA200110254B/xx unknown
2003
- 2003-02-13 US US10/366,212 patent/US20040198797A1/en not_active Abandoned

Also Published As

Publication number	Publication date
ATE250113T1 (de)	2003-10-15
HU230021B1 (hu)	2015-05-28
KR20020012272A (ko)	2002-02-15
US6552187B1 (en)	2003-04-22
ZA200110254B (en)	2003-09-01
PL353184A1 (en)	2003-11-03
MXPA01012486A (es)	2002-06-04
CA2374279C (en)	2011-02-08
IL146579A (en)	2010-04-29
CA2374279A1 (en)	2000-12-28
IL146579A0 (en)	2002-07-25
PL201663B1 (pl)	2009-04-30
AR029166A1 (es)	2003-06-18
DE60005338D1 (de)	2003-10-23
WO2000078881A3 (en)	2001-05-17
JP2003503317A (ja)	2003-01-28
DE60005338T2 (de)	2004-04-08
WO2000078881A2 (en)	2000-12-28
CN1355806A (zh)	2002-06-26
BR0011702A (pt)	2002-03-26
BR0011702B1 (pt)	2011-01-25
CN1140528C (zh)	2004-03-03
EP1183317B1 (en)	2003-09-17
RU2244715C2 (ru)	2005-01-20
JP4080743B2 (ja)	2008-04-23
HUP0201492A2 (en)	2002-08-28
KR100752941B1 (ko)	2007-08-30
AU765302B2 (en)	2003-09-11
AU5682100A (en)	2001-01-09
EP1183317A2 (en)	2002-03-06
HUP0201492A3 (en)	2002-12-28
US20040198797A1 (en)	2004-10-07

Publication	Publication Date	Title
UA73511C2 (en)	2005-08-15	Herbicide compounds, a method for the preparation thereof and intermediary compounds
US20040248739A1 (en)	2004-12-09	Pyridylpropynyloxyphenyl derivatives for use as herbicides
DE60120964T2 (de)	2007-01-04	Substituierte pyridine mit herbizider wirkung
EP0041623B1 (en)	1985-08-28	Substituted imidazolinyl nicotine acids, esters and salts and use thereof as herbicidal agents
DE69925610T2 (de)	2006-04-27	Als herbicide verwendbare pyridin-ketone
DE69932628T2 (de)	2006-12-14	Herbizide
US6274536B1 (en)	2001-08-14	Pyrazole derivatives as herbicides
WO2004002947A1 (en)	2004-01-08	Phenoxypropenylphenyl derivatives and their use as herbicides
EP2046788A1 (en)	2009-04-15	Triazolopyridine derivatives as herbicides
KR20000053201A (ko)	2000-08-25	제초제로서 유용한 피라졸 유도체
US20040102325A1 (en)	2004-05-27	Phenylpropynyloxypyridine herbicides
AU2002218200A1 (en)	2002-06-27	Phenylpropynyloxypyridine herbicides
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