SK123094A3 - Oxodiazolecarboxyamides compounds, method of their production intermediates for their production and herbicidal agents on their base and their use for growth suppression of nondesirable plants - Google Patents

Oxodiazolecarboxyamides compounds, method of their production intermediates for their production and herbicidal agents on their base and their use for growth suppression of nondesirable plants Download PDF

Info

Publication number: SK123094A3
Authority: SK; Slovakia
Prior art keywords: formula; alkyl; compounds; compound; optionally substituted
Prior art date: 1993-10-08

Application number

SK1230-94A

Other languages

English (en)

Slovak (sk)

Inventor

Wolfgang Buck

Original Assignee

Shell Int Research

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.)

1993-10-08

Filing date

1994-10-10

Publication date

1995-06-07

1994-10-10 Application filed by Shell Int Research filed Critical Shell Int Research

1995-06-07 Publication of SK123094A3 publication Critical patent/SK123094A3/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 59
238000000034 method Methods 0.000 title claims abstract description 27
239000004009 herbicide Substances 0.000 title claims description 4
239000000543 intermediate Substances 0.000 title abstract description 3
238000004519 manufacturing process Methods 0.000 title description 7
206010053759 Growth retardation Diseases 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 15
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 12
125000003118 aryl group Chemical group 0.000 claims abstract description 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
125000004475 heteroaralkyl group Chemical group 0.000 claims abstract description 8
125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims description 51
-1 oxadiazolecarboxamide compound Chemical class 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
230000002363 herbicidal effect Effects 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 10
239000004094 surface-active agent Substances 0.000 claims description 10
239000000969 carrier Substances 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
XPOCDBNHSLXVHO-UHFFFAOYSA-N oxadiazole-4-carboxamide Chemical class NC(=O)C1=CON=N1 XPOCDBNHSLXVHO-UHFFFAOYSA-N 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
230000001629 suppression Effects 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 abstract 1
239000000243 solution Substances 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
239000007787 solid Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
238000005481 NMR spectroscopy Methods 0.000 description 16
238000002844 melting Methods 0.000 description 15
230000008018 melting Effects 0.000 description 15
229910052739 hydrogen Inorganic materials 0.000 description 13
239000001257 hydrogen Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
241000196324 Embryophyta Species 0.000 description 11
239000002689 soil Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
238000005507 spraying Methods 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
239000007788 liquid Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 7
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
239000013256 coordination polymer Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000011737 fluorine Substances 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
239000008187 granular material Substances 0.000 description 5
150000002431 hydrogen Chemical group 0.000 description 5
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000007921 spray Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000003623 enhancer Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000003921 oil Substances 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
230000035515 penetration Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
XFKYKTBPRBZDFG-UHFFFAOYSA-N 2-aminoacetonitrile;hydrochloride Chemical compound Cl.NCC#N XFKYKTBPRBZDFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
240000007594 Oryza sativa Species 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
SKRDXYBATCVEMS-UHFFFAOYSA-N isopropyl nitrite Chemical compound CC(C)ON=O SKRDXYBATCVEMS-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
UYCUMNRCCJNSBR-UHFFFAOYSA-N 2-ethoxy-2-oxoacetic acid;hydrochloride Chemical compound Cl.CCOC(=O)C(O)=O UYCUMNRCCJNSBR-UHFFFAOYSA-N 0.000 description 2
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 2
150000003931 anilides Chemical class 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 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
150000001721 carbon Chemical group 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000000428 dust Substances 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
238000009472 formulation Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 1
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
150000005071 1,2,4-oxadiazoles Chemical class 0.000 description 1
LYJBVRVJQXVVPI-UHFFFAOYSA-N 1-thiophen-2-ylethanamine Chemical compound CC(N)C1=CC=CS1 LYJBVRVJQXVVPI-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
OMGKYLQUXQLJEI-UHFFFAOYSA-N 2-amino-3-(2-fluorophenyl)-3-oxopropanenitrile Chemical compound N#CC(N)C(=O)C1=CC=CC=C1F OMGKYLQUXQLJEI-UHFFFAOYSA-N 0.000 description 1
RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-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
DVFGEIYOLIFSRX-UHFFFAOYSA-N 3-(2-ethylhexoxy)propan-1-amine Chemical compound CCCCC(CC)COCCCN DVFGEIYOLIFSRX-UHFFFAOYSA-N 0.000 description 1
MXZMACXOMZKYHJ-UHFFFAOYSA-N 4,4-dimethyl-3-oxopentanenitrile Chemical compound CC(C)(C)C(=O)CC#N MXZMACXOMZKYHJ-UHFFFAOYSA-N 0.000 description 1
GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
WCQVKSJIOUXRBX-UHFFFAOYSA-N 5-(2-fluorophenyl)-1,2,4-oxadiazole Chemical compound FC1=CC=CC=C1C1=NC=NO1 WCQVKSJIOUXRBX-UHFFFAOYSA-N 0.000 description 1
235000021533 Beta vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
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OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
244000067602 Chamaesyce hirta Species 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
229910017489 Cu I Inorganic materials 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
240000006240 Linum usitatissimum Species 0.000 description 1
235000004431 Linum usitatissimum Nutrition 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
101001077374 Oryza sativa subsp. japonica UMP-CMP kinase 3 Proteins 0.000 description 1
244000088461 Panicum crus-galli Species 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
101100388071 Thermococcus sp. (strain GE8) pol gene Proteins 0.000 description 1
235000007244 Zea mays Nutrition 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
150000007960 acetonitrile Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002318 adhesion promoter Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000007798 antifreeze agent Substances 0.000 description 1
239000010426 asphalt Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
239000013058 crude material Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
SQEDZTDNVYVPQL-UHFFFAOYSA-N dodecylbenzene;sodium Chemical compound [Na].CCCCCCCCCCCCC1=CC=CC=C1 SQEDZTDNVYVPQL-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
235000004426 flaxseed Nutrition 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
235000012243 magnesium silicates Nutrition 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
239000008268 mayonnaise Substances 0.000 description 1
235000010746 mayonnaise Nutrition 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000003607 modifier Substances 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
VTRQBWNWLFDINX-UHFFFAOYSA-N n-(cyanomethyl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NCC#N VTRQBWNWLFDINX-UHFFFAOYSA-N 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
239000000025 natural resin Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
230000002688 persistence Effects 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
229950011008 tetrachloroethylene Drugs 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
238000001665 trituration Methods 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 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
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SK1230-94A 1993-10-08 1994-10-10 Oxodiazolecarboxyamides compounds, method of their production intermediates for their production and herbicidal agents on their base and their use for growth suppression of nondesirable plants SK123094A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP93116308		1993-10-08

Publications (1)

Publication Number	Publication Date
SK123094A3 true SK123094A3 (en)	1995-06-07

Family

ID=8213331

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1230-94A SK123094A3 (en)	1993-10-08	1994-10-10	Oxodiazolecarboxyamides compounds, method of their production intermediates for their production and herbicidal agents on their base and their use for growth suppression of nondesirable plants

Country Status (18)

Country	Link
US (3)	US5578550A (fr)
EP (1)	EP0647635B1 (fr)
JP (1)	JPH07165737A (fr)
KR (1)	KR950011424A (fr)
CN (1)	CN1112553A (fr)
AT (1)	ATE168108T1 (fr)
AU (1)	AU7448894A (fr)
BR (1)	BR9404025A (fr)
CA (1)	CA2133798A1 (fr)
CZ (1)	CZ244394A3 (fr)
DE (1)	DE69411486T2 (fr)
ES (1)	ES2120576T3 (fr)
HU (1)	HUT69031A (fr)
IL (1)	IL111178A0 (fr)
RU (1)	RU94036445A (fr)
SG (1)	SG47754A1 (fr)
SK (1)	SK123094A3 (fr)
ZA (1)	ZA947888B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2757856B1 (fr) *	1996-12-27	2000-06-02	American Cyanamid Co	Compose, procede pour sa preparation, composition herbicide le contenant, et son utilisation
US6699853B2 (en) *	1997-06-16	2004-03-02	Hoechst Schering Agrevo Gmbh	4-haloalkyl-3-heterocyclylpyridines, 4-haloalkyl-5-heterocyclyl-pyrimidines and 4-trifluoromethyl-3-oxadiazolylpyridines, processes for their preparation, compositions comprising them, and their use as pesticides
DE10027151A1 (de) *	2000-05-31	2001-12-06	Bayer Ag	Herbizide Mittel auf Basis von substituierten Carbonsäureamiden
DE102004051277A1 (de)	2004-10-21	2006-04-27	Merck Patent Gmbh	Heterocyclische Carbonylverbindungen
AR078793A1 (es)	2009-10-27	2011-12-07	Orion Corp	Derivados de carboxamidas no esteroidales y acil hidrazona moduladores de receptores androgenicos de tejido selectivo (sarm), composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento del cancer de prostata entre otros
US8937177B2 (en)	2010-03-23	2015-01-20	Basf Se	Pyridazine compounds for controlling invertebrate pests
EP2593447B1 (fr)	2010-07-15	2016-08-17	Bayer Intellectual Property GmbH	Composés de 3-pyridyl-heteroarylcarboxamide comme d'agents de lutte contre les nuisibles
IL296510A (en) *	2020-03-25	2022-11-01	Basf Se	Dioxazolines and their use as herbicides
JP7805983B2 (ja)	2022-03-22	2026-01-26	アッヴィ・インコーポレイテッド	ブルトン型チロシンキナーゼを分解するためのピリミジン
CN114933573B (zh) *	2022-05-06	2023-10-20	贵州大学	3-取代-1,2,4-噁二唑-5-羧酸类衍生物、其制备方法及应用

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1124502B (de) *	1960-12-08	1962-03-01	Bayer Ag	Verfahren zur Herstellung von 1, 2, 4-Oxdiazol-carbonsaeureestern-(3)
FR2056107A5 (en) *	1969-07-28	1971-05-14	Berlin Chemie Veb	1,2,4-oxadiazole-3-carboxylic acid amides
FR2095480A5 (en) *	1970-06-04	1972-02-11	Berlin Chemie Veb	1,2,4-oxadiazole-3-carboxylic acid ester prepn - by - nitrosation of n-acylamino acetonitriles
US3991067A (en) *	1971-05-19	1976-11-09	Glaxo Laboratories Limited	Mono- or disubstituted 1,2,4,oxadiazoles which are substituted by at least 1-N-substituted carbamoyl group
US4148801A (en) *	1978-07-03	1979-04-10	American Home Products Corporation	3-[(Chlorophenylsulfonyl)methyl]-1,2,4-oxadiazole-5-carboxylic acid derivatives
US5242890A (en) *	1988-07-07	1993-09-07	Korea Research Institute Of Chemical Technology	1,2,4-oxadiazole derivative, useful as selective herbicide
US5201932A (en) *	1989-09-22	1993-04-13	Basf Aktiengesellschaft	Carboxamides
DE59009528D1 (de) *	1989-09-22	1995-09-21	Basf Ag	Carbonsäureamide.
CA2126976A1 (fr) *	1991-12-31	1993-07-08	Hisashi Takasugi	Derives d'oxadiazole inhibiteurs de l'activite de l'acetylcholinesterase et agonistes muscariniques
DE4306962A1 (de) *	1993-03-05	1994-09-08	Bayer Ag	Oxadiazolcarbonsäurederivate
JPH06302990A (ja) *	1993-04-13	1994-10-28	Sharp Corp	位置指示装置

1994
- 1994-10-05 CZ CZ942443A patent/CZ244394A3/cs unknown
- 1994-10-05 US US08/318,327 patent/US5578550A/en not_active Expired - Fee Related
- 1994-10-06 IL IL11117894A patent/IL111178A0/xx unknown
- 1994-10-06 ES ES94307357T patent/ES2120576T3/es not_active Expired - Lifetime
- 1994-10-06 EP EP94307357A patent/EP0647635B1/fr not_active Expired - Lifetime
- 1994-10-06 CA CA002133798A patent/CA2133798A1/fr not_active Abandoned
- 1994-10-06 SG SG1996004218A patent/SG47754A1/en unknown
- 1994-10-06 DE DE69411486T patent/DE69411486T2/de not_active Expired - Fee Related
- 1994-10-06 AT AT94307357T patent/ATE168108T1/de not_active IP Right Cessation
- 1994-10-07 ZA ZA947888A patent/ZA947888B/xx unknown
- 1994-10-07 HU HU9402900A patent/HUT69031A/hu unknown
- 1994-10-07 CN CN94118684A patent/CN1112553A/zh active Pending
- 1994-10-07 RU RU94036445/04A patent/RU94036445A/ru unknown
- 1994-10-07 KR KR1019940025699A patent/KR950011424A/ko not_active Withdrawn
- 1994-10-07 BR BR9404025A patent/BR9404025A/pt not_active IP Right Cessation
- 1994-10-07 AU AU74488/94A patent/AU7448894A/en not_active Abandoned
- 1994-10-10 SK SK1230-94A patent/SK123094A3/sk unknown
- 1994-10-11 JP JP6271700A patent/JPH07165737A/ja active Pending
1995
- 1995-06-01 US US08/457,252 patent/US5593946A/en not_active Expired - Lifetime
1996
- 1996-08-06 US US08/699,720 patent/US5707935A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE69411486D1 (de)	1998-08-13
US5593946A (en)	1997-01-14
CA2133798A1 (fr)	1995-04-09
RU94036445A (ru)	1996-08-20
US5578550A (en)	1996-11-26
HUT69031A (en)	1995-08-28
US5707935A (en)	1998-01-13
AU7448894A (en)	1995-04-27
IL111178A0 (en)	1994-12-29
EP0647635B1 (fr)	1998-07-08
ZA947888B (en)	1995-05-24
ES2120576T3 (es)	1998-11-01
SG47754A1 (en)	1998-04-17
HU9402900D0 (en)	1995-02-28
CZ244394A3 (en)	1995-06-14
BR9404025A (pt)	1995-06-13
ATE168108T1 (de)	1998-07-15
CN1112553A (zh)	1995-11-29
DE69411486T2 (de)	1998-11-12
EP0647635A1 (fr)	1995-04-12
JPH07165737A (ja)	1995-06-27
KR950011424A (ko)	1995-05-15

Publication	Publication Date	Title
JP3044402B2 (ja)	2000-05-22	除草性カルボキシアミド誘導体
JP3728324B2 (ja)	2005-12-21	１−置換−４−カルバモイル−１，２，４−トリアゾール−５−オン誘導体及び除草剤
DK1717231T3 (en)	2015-12-07	SUBSTITUTED AZOL COMPOUNDS AND MANUFACTURING AND USING THEREOF
NO171364B (no)	1992-11-23	N-aryl-3-aryl-4,5-dihydro-1h-pyrazol-1-karboksamider og fremgangsmaate til fremstilling derav, samt insektmiddel sominneholder karboksamidet
JPH04290805A (ja)	1992-10-15	除草性カルボキシアミド誘導体
JPS6115877A (ja)	1986-01-23	Ｎ‐（２‐ニトロフエニル）‐２‐アミノピリミジン誘導体、その製造方法及び該化合物を含有する組成物
JP2008074841A (ja)	2008-04-03	新規なハロアルキルスルホンアニリド誘導体、除草剤及びその使用方法
JP2001354660A (ja)	2001-12-25	除草剤
US5134145A (en)	1992-07-28	Pesticidal pyrimidinyl benzoic acids and esters
CZ244394A3 (en)	1995-06-14	Herbicidal 1,2,4-oxadiazolecarboxylic acids amides, esters or halides
CS226434B2 (en)	1984-03-19	Herbicide and method of preparing its active substance
JP2905982B2 (ja)	1999-06-14	複素環含有フェニルピラゾール誘導体又はその塩類及びその製造方法並びに除草剤
JPH0336826B2 (fr)	1991-06-03
SK15896A3 (en)	1996-10-02	£1,3,4\|oxadiazoles and £1,3,4\|thiadiazoles, method of their manufacture, hebicidal agent on their base and plant growth inhibition method
SK15796A3 (en)	1996-11-06	£1,2,4\|thiadiazoles and herbicidal agents on their base
US5110348A (en)	1992-05-05	Glycine compounds and herbicidal compositions thereof
KR920005411B1 (ko)	1992-07-03	치환된 테트라졸의 제법
JPS6365069B2 (fr)	1988-12-14
CA2163786A1 (fr)	1994-12-08	Derives herbicides du thiazole
JPH03204867A (ja)	1991-09-06	アラルキルオキシアミン誘導体および除草剤
CA2086086A1 (fr)	1993-06-25	Herbicides du type sulfonamide
JPS61189279A (ja)	1986-08-22	５‐クロロ‐１，３，４‐チアジアゾール‐２‐イルオキシアセタミド
CN1015623B (zh)	1992-02-26	N-酰苯胺除草剂
JPS60172949A (ja)	1985-09-06	アルコキシアミノ−またはポリアルコキシアミノジフエニルエ−テル、その製造方法及びそれを含有する除草剤組成物
CS196225B2 (en)	1980-03-31	Herbicide and method of producing the active constituents