ZA200107802B - 1-aryl-1,3,5-triazine-4-thione-2,6-diones, production thereof and use thereof as herbicides. - Google Patents

1-aryl-1,3,5-triazine-4-thione-2,6-diones, production thereof and use thereof as herbicides. Download PDF

Info

Publication number: ZA200107802B
Authority: ZA; South Africa
Prior art keywords: alkyl; alkoxy; halogen; carbonyl; hydrogen
Prior art date: 1999-02-23

Application number

ZA200107802A

Other languages

English (en)

Inventor

Olaf Menke

Ingo Sagasser

Gerhard Hamprecht

Robert Reinhard

Cyrill Zagar

Karl-Otto Westphalen

Martina Otten

Helmut Walter

Original Assignee

Basf 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.)

1999-02-23

Filing date

2001-09-21

Publication date

2002-09-23

2001-09-21 Application filed by Basf Ag filed Critical Basf Ag

2002-09-23 Publication of ZA200107802B publication Critical patent/ZA200107802B/en

Links

239000004009 herbicide Substances 0.000 title claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 29
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
229910052736 halogen Chemical group 0.000 claims description 27
150000002367 halogens Chemical group 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 27
150000001875 compounds Chemical class 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
230000002363 herbicidal effect Effects 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 8
150000002084 enol ethers Chemical class 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
125000003396 thiol group Chemical class [H]S* 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 12
125000003545 alkoxy group Chemical group 0.000 claims 2
239000007788 liquid Substances 0.000 claims 2
239000007787 solid Substances 0.000 claims 2
239000004094 surface-active agent Substances 0.000 claims 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
239000012948 isocyanate Substances 0.000 claims 1
150000002513 isocyanates Chemical class 0.000 claims 1
150000003585 thioureas Chemical class 0.000 claims 1
-1 phosphonium ions Chemical class 0.000 description 397
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
150000003254 radicals Chemical class 0.000 description 11
239000000460 chlorine Substances 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
125000004710 2-methylpropylthio group Chemical group CC(CS*)C 0.000 description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
125000005290 ethynyloxy group Chemical group C(#C)O* 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
125000006606 n-butoxy group Chemical group 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
125000006150 1,1,2-trimethylpropyl sulfonyl group Chemical group 0.000 description 1
125000004884 1,1,2-trimethylpropylcarbonyl group Chemical group CC(C(C)C)(C(=O)*)C 0.000 description 1
125000006142 1,1-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
125000004876 1,1-dimethylbutylcarbonyl group Chemical group CC(CCC)(C(=O)*)C 0.000 description 1
125000004866 1,1-dimethylethylcarbonyl group Chemical group CC(C)(C(=O)*)C 0.000 description 1
125000006133 1,1-dimethylpropyl sulfonyl group Chemical group 0.000 description 1
125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
125000006151 1,2,2-trimethylpropyl sulfonyl group Chemical group 0.000 description 1
125000004885 1,2,2-trimethylpropylcarbonyl group Chemical group CC(C(C)(C)C)C(=O)* 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
125000006143 1,2-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
125000004877 1,2-dimethylbutylcarbonyl group Chemical group CC(C(CC)C)C(=O)* 0.000 description 1
125000006134 1,2-dimethylpropyl sulfonyl group Chemical group 0.000 description 1
125000004868 1,2-dimethylpropylcarbonyl group Chemical group CC(C(C)C)C(=O)* 0.000 description 1
125000006144 1,3-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
125000004878 1,3-dimethylbutylcarbonyl group Chemical group CC(CC(C)C)C(=O)* 0.000 description 1
HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 1
125000006145 2,2-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
125000004879 2,2-dimethylbutylcarbonyl group Chemical group CC(CC(=O)*)(CC)C 0.000 description 1
125000006135 2,2-dimethylpropyl sulfonyl group Chemical group 0.000 description 1
125000004869 2,2-dimethylpropylcarbonyl group Chemical group CC(CC(=O)*)(C)C 0.000 description 1
125000006146 2,3-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
125000004880 2,3-dimethylbutylcarbonyl group Chemical group CC(CC(=O)*)C(C)C 0.000 description 1
125000005999 2-bromoethyl group Chemical group 0.000 description 1
125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 1
KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000006149 2-ethylbutyl sulfonyl group Chemical group 0.000 description 1
125000004883 2-ethylbutylcarbonyl group Chemical group C(C)C(CC(=O)*)CC 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000006131 2-methylbutyl sulfonyl group Chemical group 0.000 description 1
125000004680 2-methylbutylcarbonyl group Chemical group CC(CC(=O)*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000006139 2-methylpentyl sulfonyl group Chemical group 0.000 description 1
125000004873 2-methylpentylcarbonyl group Chemical group CC(CC(=O)*)CCC 0.000 description 1
125000006128 2-methylpropyl sulfonyl group Chemical group 0.000 description 1
125000006147 3,3-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
125000004881 3,3-dimethylbutylcarbonyl group Chemical group CC(CCC(=O)*)(C)C 0.000 description 1
125000004730 3,3-dimethylbutylthio group Chemical group CC(CCS*)(C)C 0.000 description 1
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000006132 3-methylbutyl sulfonyl group Chemical group 0.000 description 1
125000004681 3-methylbutylcarbonyl group Chemical group CC(CCC(=O)*)C 0.000 description 1
RYKZRKKEYSRDNF-UHFFFAOYSA-N 3-methylidenepentane Chemical compound CCC(=C)CC RYKZRKKEYSRDNF-UHFFFAOYSA-N 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
125000006140 3-methylpentyl sulfonyl group Chemical group 0.000 description 1
125000004874 3-methylpentylcarbonyl group Chemical group CC(CCC(=O)*)CC 0.000 description 1
125000006141 4-methylpentyl sulfonyl group Chemical group 0.000 description 1
125000004875 4-methylpentylcarbonyl group Chemical group CC(CCCC(=O)*)C 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
125000005133 alkynyloxy group Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000004761 hexafluorosilicates Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000006137 n-hexyl sulfonyl group Chemical group 0.000 description 1
125000002412 n-penten-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000002504 n-penten-4-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000006129 n-pentyl sulfonyl group Chemical group 0.000 description 1
125000004712 n-pentylthio group Chemical group C(CCCC)S* 0.000 description 1
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
125000005537 sulfoxonium group Chemical group 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
125000005323 thioketone group Chemical group 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/38—Sulfur atoms
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- 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
- A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Landscapes

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

ZA200107802A 1999-02-23 2001-09-21 1-aryl-1,3,5-triazine-4-thione-2,6-diones, production thereof and use thereof as herbicides. ZA200107802B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19907649		1999-02-23

Publications (1)

Publication Number	Publication Date
ZA200107802B true ZA200107802B (en)	2002-09-23

Family

ID=7898484

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200107802A ZA200107802B (en)	1999-02-23	2001-09-21	1-aryl-1,3,5-triazine-4-thione-2,6-diones, production thereof and use thereof as herbicides.

Country Status (20)

Country	Link
US (1)	US6602825B1 (no)
EP (1)	EP1157012A1 (no)
JP (1)	JP2002537387A (no)
KR (1)	KR20010108246A (no)
CN (1)	CN1341105A (no)
AU (1)	AU2909400A (no)
BG (1)	BG105921A (no)
BR (1)	BR0008435A (no)
CA (1)	CA2364660A1 (no)
CZ (1)	CZ20013015A3 (no)
EA (1)	EA200100825A1 (no)
HU (1)	HUP0200030A3 (no)
IL (1)	IL144741A0 (no)
NO (1)	NO20014050L (no)
NZ (1)	NZ513917A (no)
PL (1)	PL350853A1 (no)
SK (1)	SK11792001A3 (no)
TR (1)	TR200102479T2 (no)
WO (1)	WO2000050409A1 (no)
ZA (1)	ZA200107802B (no)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6613718B2 (en)	2001-10-01	2003-09-02	Ishihara Sangyo Kaisha, Ltd.	Aryl ether derivatives and processes for their preparation and herbicidal and desiccant compositions containing them
US7429035B2 (en) *	2005-09-29	2008-09-30	Wprwmdm, L.L.C.	Equipment handling apparatus
EP3034528B1 (de) *	2014-12-19	2017-06-21	Evonik Degussa GmbH	Covernetzersysteme für Verkapselungsfolien umfassend Harnstoffverbindungen
CN112745305A (zh) *	2019-10-29	2021-05-04	沈阳中化农药化工研发有限公司	一种三嗪酮类化合物及其用途
AU2020378483A1 (en)	2019-11-07	2022-05-26	Qingdao Kingagroot Chemical Compound Co., Ltd.	Substituted-isoxazoline-containing aromatic compound, preparation method therefor, herbicidal composition and use thereof
JP2023510328A (ja)	2020-01-11	2023-03-13	チンタオ、キングアグルート、ケミカル、コンパウンド、カンパニー、リミテッド	カルボン酸誘導体で置換されたイミノアリール化合物、その調製方法、除草剤組成物及び使用
BR112021023672A2 (pt)	2020-01-16	2022-08-02	Qingdao Kingagroot Chemical Compound Co Ltd	Um composto aromático substituído por anel fundido, método de preparação, composição herbicida e uso dos mesmos
CN113831299B (zh) *	2020-06-23	2023-12-01	沈阳中化农药化工研发有限公司	苯甲酸酯类化合物及其应用
CN113831298B (zh) *	2020-06-23	2023-12-01	沈阳中化农药化工研发有限公司	光活性羧酸酯类化合物及其应用
CN115103837B (zh) *	2020-06-23	2023-12-29	沈阳中化农药化工研发有限公司	三嗪苯甲酸酯类化合物及其应用
CA3241044A1 (en)	2021-12-22	2023-06-29	William Guy Whittingham	Triazine herbicidal compounds
CN118216517A (zh) *	2022-12-21	2024-06-21	沈阳中化农药化工研发有限公司	一种除草组合物及其应用

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE121517C (no)
DD121517A1 (no) *	1975-06-10	1976-08-05
JPS5675407A (en) *	1979-11-22	1981-06-22	Ube Ind Ltd	Herbicide
DE4000624A1 (de)	1990-01-11	1991-07-18	Bayer Ag	Fungizide verwendung von trisubstituierten 1,3,5-triazin-2,4,6-trionen, neue trisubstituierte 1,3,5-triazin-2,4,6-trione und verfahren zu ihrer herstellung
DE4228000A1 (de) *	1992-08-24	1994-03-03	Bayer Ag	3-Aryl-triazin-2,4-dione
DE4329096A1 (de)	1993-08-30	1995-03-02	Bayer Ag	Heterocyclylbenzoheterocyclen
US5616706A (en)	1995-06-02	1997-04-01	American Cyanamid Company	1-(3-heterocyclylphenyl)-s-triazine-2,4,6-oxo or thiotrione herbicidal agents
CZ146196A3 (en) *	1995-06-02	1997-05-14	American Cyanamid Co	1-(3-heterocyclylphenyl)-s-triazin-2,4,6-oxo or thiotriones and herbicidal agent based thereon
EP0853620A1 (en)	1995-10-04	1998-07-22	Fmc Corporation	Herbicidal heterocyclic benzisoxazoles and benzisoxazolidinones
DE19731784A1 (de)	1997-07-24	1999-02-04	Bayer Ag	Substituierte N-Aryl-N-thioxocarbonyl-sulfonamide

2000
- 2000-02-10 SK SK1179-2001A patent/SK11792001A3/sk unknown
- 2000-02-10 JP JP2000600992A patent/JP2002537387A/ja not_active Withdrawn
- 2000-02-10 CN CN00804192A patent/CN1341105A/zh active Pending
- 2000-02-10 PL PL00350853A patent/PL350853A1/xx not_active Application Discontinuation
- 2000-02-10 US US09/913,466 patent/US6602825B1/en not_active Expired - Fee Related
- 2000-02-10 HU HU0200030A patent/HUP0200030A3/hu unknown
- 2000-02-10 EA EA200100825A patent/EA200100825A1/ru unknown
- 2000-02-10 KR KR1020017010664A patent/KR20010108246A/ko not_active Application Discontinuation
- 2000-02-10 EP EP00907538A patent/EP1157012A1/de not_active Withdrawn
- 2000-02-10 NZ NZ513917A patent/NZ513917A/xx not_active Application Discontinuation
- 2000-02-10 WO PCT/EP2000/001072 patent/WO2000050409A1/de not_active Application Discontinuation
- 2000-02-10 IL IL14474100A patent/IL144741A0/xx unknown
- 2000-02-10 CA CA002364660A patent/CA2364660A1/en not_active Abandoned
- 2000-02-10 CZ CZ20013015A patent/CZ20013015A3/cs unknown
- 2000-02-10 TR TR2001/02479T patent/TR200102479T2/xx unknown
- 2000-02-10 AU AU29094/00A patent/AU2909400A/en not_active Abandoned
- 2000-02-10 BR BR0008435-2A patent/BR0008435A/pt not_active Application Discontinuation
2001
- 2001-08-20 NO NO20014050A patent/NO20014050L/no not_active Application Discontinuation
- 2001-09-19 BG BG105921A patent/BG105921A/xx unknown
- 2001-09-21 ZA ZA200107802A patent/ZA200107802B/en unknown

Also Published As

Publication number	Publication date
SK11792001A3 (sk)	2002-01-07
CA2364660A1 (en)	2000-08-31
AU2909400A (en)	2000-09-14
WO2000050409A1 (de)	2000-08-31
US6602825B1 (en)	2003-08-05
BG105921A (en)	2002-06-28
HUP0200030A2 (hu)	2002-05-29
NO20014050L (no)	2001-08-22
CZ20013015A3 (cs)	2002-07-17
NO20014050D0 (no)	2001-08-20
PL350853A1 (en)	2003-02-10
HUP0200030A3 (en)	2003-01-28
IL144741A0 (en)	2002-06-30
NZ513917A (en)	2001-09-28
JP2002537387A (ja)	2002-11-05
BR0008435A (pt)	2002-01-15
CN1341105A (zh)	2002-03-20
KR20010108246A (ko)	2001-12-07
TR200102479T2 (tr)	2002-01-21
EP1157012A1 (de)	2001-11-28
EA200100825A1 (ru)	2002-02-28

Publication	Publication Date	Title
ZA200107802B (en)	2002-09-23	1-aryl-1,3,5-triazine-4-thione-2,6-diones, production thereof and use thereof as herbicides.
US6150303A (en)	2000-11-21	Substituted 3-phenylisoxazolines
US6624119B1 (en)	2003-09-23	3-[Benz(ox/thi)azol-7-yl]-1h-pyrimidine-2,4-diones
AU716701B2 (en)	2000-03-02	Substituted benzothiazoles as crop protection agents
US6639070B1 (en)	2003-10-28	N-substituted perhydrodiazine
US6013606A (en)	2000-01-11	Substituted cinnamic oxime and hydroxamide derivatives
CA2210909A1 (en)	1996-08-15	Novel 3-(4-cyanophenyl)uracils
KR19990028538A (ko)	1999-04-15	1-아미노-3-벤질우라실
US5707937A (en)	1998-01-13	Substituted phthalimidocinnamic acid derivatives and intermediates for their preparation
US5885934A (en)	1999-03-23	Substituted triazolinones as crop protection agents
EP0815106B1 (en)	2001-05-30	3-aryluracils and intermediates for their preparation
US6528455B1 (en)	2003-03-04	Phenoxy-and thiophenoxy acrylic acid compounds as herbicides
CA2349386A1 (en)	2000-05-11	Novel 1-aryl-4-thiouracils
EP1095045B1 (de)	2003-01-15	Verfahren zur herstellung von anellierten triazolen und neue anellierte triazole und deren verwendung
US6432880B1 (en)	2002-08-13	Substituted 2-phenylpyridines as herbicides
CA2421839A1 (en)	2003-03-07	Method for producing anellated tetrahydro-[1h]-triazoles
US6656884B2 (en)	2003-12-02	3-(4-cyanophenyl) uracils
SK17302000A3 (sk)	2001-05-10	Substituované 6-aryl-3-tioxo-5-(ti)oxo-2,3,4,5-tetrahydro-1,2,4-triazíny
AU5977200A (en)	2001-01-31	Substituted ureas
MXPA01008399A (en)	2002-05-09	1-aryl-1,3,5-triazine-4-thione-2,6-diones, production thereof and use thereof as herbicides
MXPA00012952A (en)	2001-09-07	Method for producing anellated triazoles and new anellated triazoles and their use
CA2203186A1 (en)	1996-05-17	Substituted phthalimido-cinnamic acid derivatives with herbicidal effect
CA2283662A1 (en)	1998-10-01	Novel 1-amino-3 benzyl uracils