SK67998A3 - 3,5-difluoropyridines and their use as herbicides - Google Patents

3,5-difluoropyridines and their use as herbicides Download PDF

Info

Publication number: SK67998A3
Authority: SK; Slovakia
Prior art keywords: methyl; difluoro; pyridine; trifluoromethylphenyl; yloxy
Prior art date: 1997-05-30

Application number

SK679-98A

Other languages

English (en)

Slovak (sk)

Inventor

Thomas Maier

Stefan Scheiblich

Helmut S Baltruschat

Original Assignee

American Cyanamid Co

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.)

1997-05-30

Filing date

1998-05-22

Publication date

1998-12-02

1998-05-22 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1998-12-02 Publication of SK67998A3 publication Critical patent/SK67998A3/sk

Links

WRXAZPPGFLETFR-UHFFFAOYSA-N 3,5-difluoropyridine Chemical class FC1=CN=CC(F)=C1 WRXAZPPGFLETFR-UHFFFAOYSA-N 0.000 title claims description 12
239000004009 herbicide Substances 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims abstract description 61
239000000203 mixture Substances 0.000 claims abstract description 39
230000002363 herbicidal effect Effects 0.000 claims abstract description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 110
-1 alkyltiovú Chemical group 0.000 claims description 59
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 52
125000000217 alkyl group Chemical group 0.000 claims description 24
125000001424 substituent group Chemical group 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 14
238000000034 method Methods 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 11
125000004438 haloalkoxy group Chemical group 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000001188 haloalkyl group Chemical group 0.000 claims description 10
125000004995 haloalkylthio group Chemical group 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
229910052717 sulfur Inorganic materials 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
KGZSSIFFYUBVOX-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]pyridine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=N1 KGZSSIFFYUBVOX-UHFFFAOYSA-N 0.000 claims description 4
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
238000006880 cross-coupling reaction Methods 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
229910052796 boron Inorganic materials 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
229910052718 tin Inorganic materials 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
MFDBYHAXXAGPNF-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenoxy]pyridine Chemical compound FC(F)(F)C1=CC=CC(OC=2N=CC=CC=2)=C1 MFDBYHAXXAGPNF-UHFFFAOYSA-N 0.000 claims 1
YFYFFHHDKGUREL-UHFFFAOYSA-N 3,5-difluoro-4-methyl-2-[3-(trifluoromethyl)phenoxy]-6-[4-(trifluoromethyl)phenyl]pyridine Chemical compound N=1C(C=2C=CC(=CC=2)C(F)(F)F)=C(F)C(C)=C(F)C=1OC1=CC=CC(C(F)(F)F)=C1 YFYFFHHDKGUREL-UHFFFAOYSA-N 0.000 claims 1
229910052744 lithium Inorganic materials 0.000 claims 1
229910052749 magnesium Inorganic materials 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 18
150000003839 salts Chemical class 0.000 abstract description 4
150000001204 N-oxides Chemical class 0.000 abstract 1
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
241000196324 Embryophyta Species 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000002689 soil Substances 0.000 description 9
239000011737 fluorine Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000004094 surface-active agent Substances 0.000 description 8
229910052736 halogen Inorganic materials 0.000 description 7
150000002367 halogens Chemical class 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
240000008042 Zea mays Species 0.000 description 6
239000000654 additive Substances 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
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 5
235000002017 Zea mays subsp mays Nutrition 0.000 description 5
239000000969 carrier Substances 0.000 description 5
235000013339 cereals Nutrition 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000002270 dispersing agent Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
244000068988 Glycine max Species 0.000 description 4
235000010469 Glycine max Nutrition 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
240000007594 Oryza sativa Species 0.000 description 4
235000007164 Oryza sativa Nutrition 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
239000007859 condensation product Substances 0.000 description 4
235000005822 corn Nutrition 0.000 description 4
230000006378 damage Effects 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
230000035515 penetration Effects 0.000 description 4
150000004760 silicates Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
125000004434 sulfur atom Chemical group 0.000 description 4
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
240000005979 Hordeum vulgare Species 0.000 description 3
235000007340 Hordeum vulgare Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
241000209140 Triticum Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
125000004391 aryl sulfonyl group Chemical group 0.000 description 3
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000003623 enhancer Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 2
XTGOWLIKIQLYRG-UHFFFAOYSA-N 2,3,4,5,6-pentafluoropyridine Chemical compound FC1=NC(F)=C(F)C(F)=C1F XTGOWLIKIQLYRG-UHFFFAOYSA-N 0.000 description 2
REFSEYNCNNIKQM-UHFFFAOYSA-N 2,3,5-trifluoro-4-methyl-6-[3-(trifluoromethyl)phenoxy]pyridine Chemical compound CC1=C(F)C(F)=NC(OC=2C=C(C=CC=2)C(F)(F)F)=C1F REFSEYNCNNIKQM-UHFFFAOYSA-N 0.000 description 2
241001621841 Alopecurus myosuroides Species 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
239000005562 Glyphosate Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
240000006694 Stellaria media Species 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
239000000642 acaricide Substances 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
229910052733 gallium Inorganic materials 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000000361 pesticidal effect Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011347 resin Substances 0.000 description 2
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229920006395 saturated elastomer Polymers 0.000 description 2
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238000005507 spraying Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
229910052723 transition metal Inorganic materials 0.000 description 2
150000003624 transition metals Chemical class 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VMJPFTHPDLREJZ-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-methylpyridine Chemical compound CC1=C(F)C(F)=NC(F)=C1F VMJPFTHPDLREJZ-UHFFFAOYSA-N 0.000 description 1
MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 1
KFEFNHNXZQYTEW-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-4-methylbenzoic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC(C)=CC=C1C(O)=O KFEFNHNXZQYTEW-UHFFFAOYSA-N 0.000 description 1
NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 1
CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 1
YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 description 1
UWHURBUBIHUHSU-UHFFFAOYSA-N 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 UWHURBUBIHUHSU-UHFFFAOYSA-N 0.000 description 1
YBGQODIKEAXONX-UHFFFAOYSA-N 2-[2-(trifluoromethyl)phenoxy]pyridine Chemical compound FC(F)(F)C1=CC=CC=C1OC1=CC=CC=N1 YBGQODIKEAXONX-UHFFFAOYSA-N 0.000 description 1
MPPOHAUSNPTFAJ-UHFFFAOYSA-N 2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-UHFFFAOYSA-N 0.000 description 1
CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 1
IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 1
JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 description 1
DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
WQRHIGNAKDJJKN-UHFFFAOYSA-N 2-methyl-5-(trifluoromethyl)-1h-pyrazol-3-one Chemical compound CN1NC(C(F)(F)F)=CC1=O WQRHIGNAKDJJKN-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
239000004753 textile Substances 0.000 description 1
239000002562 thickening agent Substances 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
239000013008 thixotropic agent Substances 0.000 description 1
210000001685 thyroid gland Anatomy 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
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 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
REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 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
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
239000001993 wax Chemical class 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/28—Halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK679-98A 1997-05-30 1998-05-22 3,5-difluoropyridines and their use as herbicides SK67998A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US86677297A	1997-05-30	1997-05-30

Publications (1)

Publication Number	Publication Date
SK67998A3 true SK67998A3 (en)	1998-12-02

Family

ID=25348372

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK679-98A SK67998A3 (en)	1997-05-30	1998-05-22	3,5-difluoropyridines and their use as herbicides

Country Status (26)

Country	Link
EP (1)	EP0887343B1 (et)
JP (1)	JPH111474A (et)
KR (1)	KR19980087231A (et)
CN (1)	CN1201032A (et)
AR (1)	AR012890A1 (et)
AT (1)	ATE242767T1 (et)
AU (1)	AU750083B2 (et)
BR (1)	BR9801724A (et)
CA (1)	CA2238870A1 (et)
CZ (1)	CZ155798A3 (et)
DE (1)	DE69815443T2 (et)
EE (1)	EE03796B1 (et)
EG (1)	EG22073A (et)
GE (1)	GEP20002242B (et)
HU (1)	HUP9801264A3 (et)
ID (1)	ID20352A (et)
IL (1)	IL124584A0 (et)
MD (1)	MD2101B2 (et)
NO (1)	NO311759B1 (et)
NZ (1)	NZ330551A (et)
PL (1)	PL326581A1 (et)
SK (1)	SK67998A3 (et)
TR (1)	TR199800958A2 (et)
TW (1)	TW445257B (et)
YU (1)	YU23498A (et)
ZA (1)	ZA984592B (et)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1108720A1 (en) *	1999-12-08	2001-06-20	Basf Aktiengesellschaft	Herbicidal 2-Pyrazolyl-6-Aryloxy-Pyri(mi)dines
US6528456B2 (en)	1999-12-08	2003-03-04	Basf Aktiengesellschaft	Herbicidal 2-pyrazolyl-6-aryloxypyri(mi)dines
EP1427725B1 (de) *	2001-09-07	2005-03-23	Basf Aktiengesellschaft	Pyrazolylsubstituierte thienyloxy-pyridine
KR100659088B1 (ko) *	2005-07-15	2006-12-21	삼성에스디아이 주식회사	디플루오로피리딘계 화합물 및 이를 이용한 유기 발광 소자

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1996006096A1 (en) *	1994-08-23	1996-02-29	Nissan Chemical Industries, Ltd.	Pyridine derivative
EP0723960B1 (en) *	1995-01-26	2003-04-02	Basf Aktiengesellschaft	Herbicidal 2,6-disubstituted pyridines and 2,4-disubstituted pyrimidines
EP0820996A1 (en) *	1996-07-24	1998-01-28	American Cyanamid Company	Herbicidal cyanopyridines

1998
- 1998-05-05 TW TW087106933A patent/TW445257B/zh not_active IP Right Cessation
- 1998-05-20 CZ CZ981557A patent/CZ155798A3/cs unknown
- 1998-05-20 KR KR1019980018190A patent/KR19980087231A/ko not_active Withdrawn
- 1998-05-21 IL IL12458498A patent/IL124584A0/xx unknown
- 1998-05-21 GE GEAP19984306A patent/GEP20002242B/en unknown
- 1998-05-22 AT AT98304087T patent/ATE242767T1/de not_active IP Right Cessation
- 1998-05-22 SK SK679-98A patent/SK67998A3/sk unknown
- 1998-05-22 DE DE69815443T patent/DE69815443T2/de not_active Expired - Lifetime
- 1998-05-22 EP EP98304087A patent/EP0887343B1/en not_active Expired - Lifetime
- 1998-05-27 EE EE9800085A patent/EE03796B1/et not_active IP Right Cessation
- 1998-05-27 MD MD98-0153A patent/MD2101B2/ro unknown
- 1998-05-28 AU AU69046/98A patent/AU750083B2/en not_active Ceased
- 1998-05-28 CA CA002238870A patent/CA2238870A1/en not_active Abandoned
- 1998-05-28 ZA ZA9804592A patent/ZA984592B/xx unknown
- 1998-05-28 BR BR9801724-1A patent/BR9801724A/pt not_active IP Right Cessation
- 1998-05-28 ID IDP980788A patent/ID20352A/id unknown
- 1998-05-29 JP JP16443998A patent/JPH111474A/ja not_active Withdrawn
- 1998-05-29 NZ NZ330551A patent/NZ330551A/xx unknown
- 1998-05-29 PL PL98326581A patent/PL326581A1/xx unknown
- 1998-05-29 NO NO19982469A patent/NO311759B1/no not_active IP Right Cessation
- 1998-05-29 AR ARP980102535A patent/AR012890A1/es not_active Application Discontinuation
- 1998-05-29 HU HU9801264A patent/HUP9801264A3/hu unknown
- 1998-05-29 CN CN98109528A patent/CN1201032A/zh active Pending
- 1998-05-29 YU YU23498A patent/YU23498A/sh unknown
- 1998-05-29 TR TR1998/00958A patent/TR199800958A2/xx unknown
- 1998-05-30 EG EG59498A patent/EG22073A/xx active

Also Published As

Publication number	Publication date
EG22073A (en)	2002-07-31
AU6904698A (en)	1998-12-03
MD2101B2 (ro)	2003-02-28
EP0887343B1 (en)	2003-06-11
DE69815443D1 (de)	2003-07-17
ID20352A (id)	1998-12-03
AR012890A1 (es)	2000-11-22
TW445257B (en)	2001-07-11
NO982469L (no)	1998-12-01
HU9801264D0 (en)	1998-08-28
MD980153A (en)	1999-12-31
NO982469D0 (no)	1998-05-29
CZ155798A3 (cs)	1998-12-16
AU750083B2 (en)	2002-07-11
ATE242767T1 (de)	2003-06-15
IL124584A0 (en)	1998-12-06
YU23498A (sh)	2001-12-26
EP0887343A1 (en)	1998-12-30
DE69815443T2 (de)	2003-12-24
EE9800085A (et)	1998-12-15
ZA984592B (en)	1999-11-29
JPH111474A (ja)	1999-01-06
HUP9801264A3 (en)	2000-01-28
KR19980087231A (ko)	1998-12-05
TR199800958A2 (xx)	1998-12-21
HUP9801264A2 (hu)	1999-03-29
NZ330551A (en)	1999-06-29
CN1201032A (zh)	1998-12-09
EE03796B1 (et)	2002-08-15
CA2238870A1 (en)	1998-11-30
NO311759B1 (no)	2002-01-21
PL326581A1 (en)	1998-12-07
BR9801724A (pt)	2000-03-14
GEP20002242B (en)	2000-09-25

Publication	Publication Date	Title
US6872690B2 (en)	2005-03-29	Herbicidal 2-alkynyl-pyri (mi) dines
AU7208400A (en)	2001-06-14	Herbicidal 2-pyrazolyl-6-aryloxypri (MI) dines
US6313072B1 (en)	2001-11-06	Herbicidal 2-aryloxy-or 2-arylthio-6-arylpyrimidines
US5851952A (en)	1998-12-22	Herbicidal thienyloxyazines
US6080861A (en)	2000-06-27	Herbicidal 6-thienyloxypyrid-2-carboxamides
WO1999024427A1 (en)	1999-05-20	Herbicidal furanyl- and thienyloxyazines
AU753594B2 (en)	2002-10-24	Herbicidal pyridine compounds
SK67998A3 (en)	1998-12-02	3,5-difluoropyridines and their use as herbicides
EP0902026B1 (en)	2006-04-12	Herbicidal 2-azinyl-6-aryloxypyr(mi)dines
EP1228062B1 (en)	2004-04-28	Herbicidal 2-aryloxy-6-fluoroalkylthioalk(en)yloxy-pyridines
US6310006B1 (en)	2001-10-30	Herbicidal 3,5-difluoropyridines
EP1101764B1 (en)	2003-10-22	Herbicidal 2-aryloxy-4-methyl-6-pyrazol-1-yl-pyridines
US6130188A (en)	2000-10-10	Herbicidal pyridine compounds
EP0955292A1 (en)	1999-11-10	Herbicidal 2-(cycloalk(en)yloxy)-6-(hetero)aryloxy(thio)pyridines
US6528456B2 (en)	2003-03-04	Herbicidal 2-pyrazolyl-6-aryloxypyri(mi)dines
US6534447B1 (en)	2003-03-18	Herbicidal pyridine compounds
MXPA98004141A (en)	1999-06-01	3.5-difluoropirid herbicides