CN85101141A - Diphenyl ether herbicides - Google Patents
Diphenyl ether herbicides Download PDFInfo
- Publication number
- CN85101141A CN85101141A CN85101141.1A CN85101141A CN85101141A CN 85101141 A CN85101141 A CN 85101141A CN 85101141 A CN85101141 A CN 85101141A CN 85101141 A CN85101141 A CN 85101141A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- group
- atom
- formula
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000004009 herbicide Substances 0.000 title claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 239000004480 active ingredient Substances 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 238000009333 weeding Methods 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- -1 alkyl sulfonic acid Chemical compound 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 241000196324 Embryophyta Species 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 229910052783 alkali metal Chemical group 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims 1
- 241001597008 Nomeidae Species 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical class CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 20
- 238000012360 testing method Methods 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical group FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 229960003328 benzoyl peroxide Drugs 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-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
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 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 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 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
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 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
- 239000004202 carbamide Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 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
- 230000002349 favourable effect Effects 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical class CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- ZJCVGFCOHPVDMM-UHFFFAOYSA-N 2-benzyl-5-hydroxyisoindole-1,3-dione Chemical compound O=C1C2=CC(O)=CC=C2C(=O)N1CC1=CC=CC=C1 ZJCVGFCOHPVDMM-UHFFFAOYSA-N 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
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- 235000021533 Beta vulgaris Nutrition 0.000 description 1
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- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 101000897979 Homo sapiens Putative spermatid-specific linker histone H1-like protein Proteins 0.000 description 1
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 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
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 102100021861 Putative spermatid-specific linker histone H1-like protein Human genes 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 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
- 235000021536 Sugar beet Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920013817 TRITON X-155 Polymers 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 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
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 210000005252 bulbus oculi Anatomy 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 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
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 210000001508 eye Anatomy 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
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 238000010413 gardening Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 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
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 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
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 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
- 235000019508 mustard seed Nutrition 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000005342 perphosphate group Chemical group 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent 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
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 235000013311 vegetables Nutrition 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
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The weeding composition contains the structural formulaAs an active ingredient, a diphenyl ether derivative of (5) wherein R is1Represents a hydrogen or halogen atom or is an alkyl or haloalkyl group; r2And R3Each independently represents a hydrogen or halogen atom or an alkyl, haloalkyl, nitro or cyano group; the substituents A and B have the meanings defined in the description; these diphenyl ethers are useful as herbicides; certain novel diphenyl ethers are encompassed by formula I and a process for their preparation.
Description
The present invention relates to control the composition and the method for weed growth, and relate to the compound that uses this composition and method.
In United States Patent (USP) 4334915, the phenoxy group phthalate of some replacement discloses as weed killer herbicide, disclosed therewith also have corresponding phenoxy group phthalic anhydride, this acid anhydrides preparation during phthalate only as a kind of useful intermediate and disclosed, do not mention or advise that acid anhydrides itself also can prevent the activity of any biology.Find that now such phenoxy group phthalic anhydride and a certain replacing of other have the diphenyl ether of a condensed ring to present favorable herbicidal activity together on 34.
Therefore, the present invention proposes a kind of Herbicidal combinations, and this composition comprises carrier and as the diphenyl ether derivative of active ingredient, the general formula of this derivative (I) is as follows:
R wherein
1Represent hydrogen or halogen atom, preferably chlorine; Perhaps represent alkyl or haloalkyl, preferably the fluoroform group;
R
2Or R
3, can be identical also can be inequality, each all represents hydrogen or halogen atom separately, preferably chlorine is perhaps represented alkyl, haloalkyl, nitro or cyano group;
A and B, can be identical also can be inequality, each is all represented one separately and is selected from following divalent group:>C(R
4)
2;-X-;>N-R
5;>C=X and>SO
2Group, if A representative-X-or>SO
2, then B must be different from A and can not be>C=X;
Each R
4Can be the same or different, it represents hydrogen or halogen atom or alkyl, cycloalkyl, alkylene, alkynyl, aryl, suitable phenyl, aralkyl, alkaryl, alkoxyl, cycloalkyloxy, alkenyloxy, alkynyloxy group, alkoxy carbonyl alkoxyl, alkylthio, acyl group, acyloxy, carboxyl, alkoxy carbonyl or heterocyclic radical, a chemical formula that replaces or do not replace is NR
6R
7Amido, perhaps R
4Represent hydrogen atom, alkoxyl or hydrocarbon group, and another R
4Can be hydroxyl, perhaps two R
4On behalf of a chemical formula, base together be=NR
6Imido grpup;
R
5Alkyl, alkoxyl, aralkyl, the alkoxy carbonyl of representing hydrogen atom, carboxyl or hydroxyl or representative to replace arbitrarily, or alkoxy carbonyl alkyl or chemical formula are NR
6R
7Amido;
R
6And R
7, can be identical also can be different, each all represents hydrogen atom or replacement or the alkyl that does not replace, aryl or acyl group;
X in the formula I and in substituting group represents oxygen or sulphur atom.
Used here term " acyl group " is meant the group of deriving by in the organic acid of removing a hydroxyl; Organic acid can be carboxylic acid (comprising carbamic acid derivative) or sulfonic acid, and the example of suitable acyl group is alkyl-carbonyl, alkyl-carbamoyl and alkyl sulphonyl, as acetyl group, methyl sulphonyl and formyl-dimethylamino.
When above-mentioned arbitrary substituting group is represented or is contained alkyl, alkylene or alkynyl substituted base, then these groups can contain 10 carbon atoms, the straight or branched group of 6 carbon atoms preferably, suitable examples is methyl, ethyl, propyl group, pi-allyl and propinyl.When substituting group representative or when containing naphthenic substituent, then can contain from 3 to 10 carbon atoms, 5-8 carbon atom preferably, suitable is cyclohexane.When containing the haloalkyl substituting group, then suitable is to contain 6 carbon atoms, and preferably 4, suitable halogen atom is a fluorine or chlorine, and special good is fluoroform.Phenyl preferably when containing aryl substituent.When containing heterocyclic group then for example can be pyrroles, pyrrolidines, pyridine,
Pyridine, furans or pyranoid ring.When above-mentioned arbitrary substituting group indicates as optional replacement, then optional here substituting group can be the substituting group that often uses in the agricultural chemical compound development, and/or the modifier of these compounds is to improve its structure/activity, persistence, permeability or other character.These substituent special cases comprise halogen, especially chlorine atom and nitro, cyano group, hydroxyl, alkoxyl, and for example methoxyl group, or ester is alkoxycarbonyl groups for example.
Best composition is that wherein active ingredient is the compound of general formula I, wherein the X represention oxygen atom;
A represention oxygen atom, carbonyl, C(R
4)
2Group, one of them R
4Base is a hydrogen atom or how to the alkyl or the alkoxyl of 4 carbon atoms, preferably methyl or methoxy, or aryl, phenyl group preferably, and another R
4Group is a hydrogen or halogen atom; chlorine or bromine preferably; hydroxyl; many alkyl to 4 carbon atoms; methoxyl group preferably; ethyoxyl or propoxyl group, by halogen atom, preferably chlorine replaces arbitrarily; or by hydroxyl or alkoxyl; preferably methoxyl group replaces, and the cycloalkyloxy of 5-8 carbon atom is cyclohexyloxy preferably, many alkenyloxy or alkynyloxy groups to 6 carbon atoms; the preferably allyloxy or third alkynyloxy group; the alkoxy carbonyl alkoxyl, ethoxy carbonyl ethyoxyl group preferably is how to the alkylthio of 4 carbon atoms; preferably sulphomethyl or sulfo-propyl group; chain triacontanol base, acetyl group preferably, pyridine radicals or chemical formula are NR
6R
7Amido, R wherein
6Represent hydrogen atom or many alkyl to 4 carbon atoms; Methyl preferably; And R
7The many alkyl of representative to 4 carbon atoms, preferably methyl has a halogen atom at least, chlorine preferably, the phenyl or alkyl-carbonyl, alkyl formyl radical or the alkyl sulphonyl that replace or do not replace, acetyl group preferably, dimethyl methyl acyl group or methyl sulphonyl;
B represention oxygen atom, C(R
4)
2Base, wherein each R
4Can be identical also can be different, they represent hydrogen atom separately or how to the alkyl or the alkoxyl of 4 carbon atoms, preferably methyl or methoxy, or NR
5Group, wherein R
5Represent hydrogen atom, how to the alkyl of 4 carbon atoms, methyl preferably, the many alkoxy carbonyl alkyls of benzyl, preferably ethoxy carbonyl methyl or ethoxy carbonyl ethyl to 8 carbon atoms.
The composition of preferably selecting for use is that wherein active ingredient compound is a kind of R
1Be trifluoromethyl, R
3Be halogen, chlorine atom preferably, R
3It is a kind of like this compound compositions of hydrogen atom.
Except that one, the compound of formula I is new, so the present invention also expands to these noval chemical compounds itself.Noval chemical compound is the diphenyl ether derivative of formula I, wherein replaces A, B, R
1, R
2, R
3, R
4, R
5, R
6And R
7Have the connotation that limits above, except that 4-(2-chloro-4-4-trifluoromethylphenopendant)-phthalic anhydride.
When substituent character is to introduce an asymmetric carbon atoms, to differentiate that then there is heterogeneous type in the compound of gained, also can there be dynamic isomer in some substituent connection.Scope of the present invention comprises compound that these are multi-form and composition thereof and contains the herbicidal composition of the active ingredient of this isomery shape and mixture.
In addition, the present invention gives the preparation method of above-mentioned new diphenyl ether, and this method comprises will have 2-benzo (C) furanone of following structural formula
With structural formula be:
Compound react wherein A, B, X, R
1, R
2And R
3Have the connotation that above-mentioned formula I is given, one of Z and Q are halogens, and suitable is chlorine, or nitro and another represent the group of chemical formula for-OM, and wherein M is hydrogen or alkali metal atom.When Q is that the compound and the alkali-metal oxyhydroxide of hydroxyl up-to-date style II is easy to react in alkanol solvent such as ethanol, generate corresponding alkali metal salt thus, this salt then with the compound reaction of formula III, wherein Z represents the chlorine atom.The reaction of above-mentioned salt and chlorine-containing compound is preferably in suitable solvent such as dromisol thiophane alum, in dimethyl formamide or the dimethylacetylamide and in the higher temperature as be preferably in the heating that refluxes between 40 ℃ more than 25 ℃, backflow and also in inert atmosphere as being suitable under the nitrogen.
On behalf of the compound of sulphur, X can be made by the similar compound and the phosphorus pentasulfide reaction of corresponding oxygen in the formula I.A is the compound and the suitable halogenating agent reaction of halogenated methylene and making.Be that the compound of CHBr can be by corresponding A=>CH as A like this
2Compound and N-bromo-succinimide reaction and making, have peroxide such as benzoic acid peroxide to exist and in solvent such as carbon tetrachloride, carry out comparatively suitable.When wherein A is the compound of hydroxyl subunit, then can make with corresponding halogenated methylene compound hydrolysis.
Formula I compound wherein X and B all is an oxygen atom and A is C(R
4)
2, one of them R
4Base is a hydrogen atom and another has the above-mentioned connotation outside dehydrogenation or the hydroxyl, and this compound can be CH(OH by A) respective compound and formula HR
4Reagent reacting and make R wherein
4Be outside dehydrogenation or the hydroxyl to the formula I fixed connotation, perhaps work as R
4R when being the carboxyl acyloxy
4Can be that chemical formula is AC
2The acyl acid anhydride of O, wherein AC is the alkyl-carbonyl group.React comparatively suitable with reaction mixture refluxed.Can be with excessive HR in some situation
4Solvent with the reaction of providing convenience; And under the another kind of situation with reagent HR
4It is more suitable that solution in organic solvent such as second eyeball or MEK is introduced.
Find that the compound of general formula I has the favorable activity of weed killer herbicide.Therefore the present invention also proposes by the compound of invention or composition also useful as herbicides.Also provide with the compound or a certain place of compositions-treated of inventing, to prevent the method for weed growth on this place by the present invention in addition.Can emerge preceding or emerge after be used in this place.The active ingredient using dosage can be, for example, and from 0.05-4 kilogram/hectare.
Carrier in the invention composition can be any material, as long as this material and active ingredient be mixed with is the processing in this place easy to use, this place can be a plant, seed or earth, and be convenient to store, transportation and operating.Carrier can be solid or liquid, comprises gas normally but the material and any carrier that generally is used to make weed killer herbicide that have been compressed into liquid all can use.By the best composition of the present invention is the active ingredient that contains 0.5-95% weight.
Suitable solid carrier comprises that for example natural silica of natural and synthetic earth and silicate is such as diatomite; Magnesium silicate, for example talcum; Magnesiumaluminumsilicate, for example Attagel and vermiculite; Alumina silicate, kaolin for example, montmorillonite and mica; Calcium carbonate; Calcium sulphate; Ammonium sulfate; Synthetic oxidizing aqueous silicon and synthetic calcium silicates or alumina silicate; Element is as carbon or sulphur; Natural and synthetic resin, cumarone resin for example, polyvinyl chloride and styrene polymer and copolymer; The polystream phenol of solid; Pitch; Wax; And solid fertilizer, for example perphosphate.
Suitable liquid-carrier comprises water; Alcohol is as isopropyl alcohol and ethylene glycol; Ketone, as acetone, MEK, methylisobutylketone and cyclohexanone; Hydrocarbon thing of aryl or the hydrocarbon thing of aromatic yl aliphat, as benzene, toluene and dimethylbenzene; Petroleum distillate is as kerosene and oil; Chlorinated hydrocarbon, as carbon tetrachloride, perchloroethylene and trichloroethanes.Mixtures of different liquids usually is suitable.
The composition of using on the agricultural often is mixed with conc forms and with the conc forms transportation, later user dilutes before use.Have a small amount of carrier, this carrier is a surfactant, with the process that is easy to dilute.Having a kind of carrier at least according to invention in composition is surfactant, can contain two kinds of carriers at least as composition, then has at least one to be surfactant.
Surfactant can be emulsifier, dispersant or wetting agent; It can be non-ionizing or ionization.Suitable surfactant comprises the sodium salt or the calcium salt of polyacrylic acid and lignosulfonic acid; In molecule, contain at least the fatty acid of 12 carbon atoms or aliphatic amine or acid amides and oxirane and (or) 1, the condensation product of 2-propylene oxide; The fatty acid ester of glycerine, sorbose, sucrose or pentaerythrite; These compounds and oxirane and (or) 1, the condensation product of 2-propylene oxide; The condensed products of fatty alcohol or alkylphenol, P-octyl cresol for example, with oxirane and (or) 1, the 2-propylene oxide; The sulphate of these condensed products or sulfonate, the sulfuric acid or the alkali metal of sulfonic acid fat or the salt of alkaline earth metal that in molecule, contain 10 carbon atoms at least, sodium salt preferably, as dodecyl sodium sulphate, Teepol, the sodium salt of sulfonation castor oil, sodium alklyarylsulfonate such as dodecyl benzene sulfonate; With polymers of ethylene oxide and oxirane and 1, the copolymer of 2-glycidyl.
Composition of the present invention for example can be mixed with wettable powder, ash end, particle, solution, emulsible concentrate, emulsion, suspending concentrate and aerosol.Wettable powder often contains the active ingredient of 25,50 or 75% weight, and often contains the dispersant of 3-10% weight except solid inert carrier, and need 0-10% weight stabilizing agent and (or) other additives such as bleeding agent or sticker.The ash end often is prepared into the grey last concentrate with the composition that is similar to wettable powder but does not have dispersant, draws the composition that often contains 1/2-10% weight active ingredient with the solid carrier dilution more in the ground.Particle is often made the granularity with size between 10 and 100 English system (BS) sieve apertures (1.676-0.152 millimeter), can prepare with the technology of cohesion or infiltration.In general, grain contains the additive of the active ingredient of 1/2-75% weight and 0-10% weight such as stabilizing agent, surfactant, slow release is put conditioning agent and adhesive.So-called " but flowing powder of doing " is made up of the quite little particle with relative high concentration active ingredient.Emulsifiable concentrate beyond desolventizing, often contains its solvent if desired, 10-50%W/V active ingredient, other additives of 2-20%W/V emulsifier and 0-28%W/V such as stabilizing agent, bleeding agent and preservative.Suspension-concentrates usually be made into can obtain a kind of stable, do not deposit mobile product and contain the active ingredient of 10-75% weight, the dispersant of 0.5-15% weight, the suspending agent of 0.1-10% weight such as protecting colloid and thixotropic agent, other additives such as defoamer, preservative, stabilizing agent, bleeding agent and the sticker of 0-10% weight, and undissolved substantially water of active ingredient and organic solvent; Have with certain organic solid or mineral salt and be dissolved in the prescription to support to stop deposition or as the antifreezing agent of water.
Moisture dispersion liquid and emulsion, for example by the wettable powder of dilute with water of the present invention or concentrate and the composition that obtains also belong within the invention scope.Above-mentioned emulsion can be Water-In-Oil or oil-in-water form, and consistence like " mayonnaise " of stiff also can be arranged.
Composition of the present invention also can contain other compositions, as has other compounds of the character of weeding, desinsection or mildew-resistant.
Following embodiment is in order to the explanation invention.
Example 1.5-(2 '-chloro-4 '-4-trifluoromethylphenopendant)-2-benzo (C) furanone
5-hydroxyl-2-benzo (C) furanone (5.5 gram) is dissolved in the ethanol (50 milliliters), adds 2.5 gram potassium hydroxide, solution refluxes and heated 3 hours.Divide and to desolvate, residue is dissolved in the dimethyl sulfoxide (DMSO) (50 milliliters), and add 8.2 gram 34-dichloros three and fluoridize benzene.Stirring this mixture 18 hours during at 160 ℃ under the blanket of nitrogen of doing, cooling is poured on ice then, and with the watery hydrochloric acid neutralization, product makes desired product with dichloromethane extraction, and its fusing point is 109-111 ℃.
Analyze: C
15H
8O
3C
1F
3Calculated value: C54.8 H2.4%
Measured value: C54.8 H2.5%
Example 2.5-(2 '-chloro-4 '-4-trifluoromethylphenopendant)-3-bromo-2-benzo (C) furanone
The product (1.5 gram) and the N-bromine succinimide (0.82 gram) of example 1 are dissolved in the dried carbon tetrachloride (25 milliliters), and add a granule benzoyl peroxide, when succinimide began to precipitate, reactant mixture refluxed under high light and stirs.The mixture cooling is filtered, and with the carbon tetrachloride washing, branch desolvates.Chromatography (silicagel column; Eluent methylene chloride) viscous oil that makes a kind of greenish orange look is desired product.
Analyze: to C
15H
7C
1BrF
3O
3Calculated value: C44.2 H1.7%
Measured value: C44.2 H1.9%
Example 3.5-(2 '-chloro-4 '-4-trifluoromethylphenopendant)-1-sulfo--2-benzo (C) furanone
The product (1.55 gram) and the phosphorus pentasulfide (2.2 gram) of example 1 are added hot reflux 1 hour and stirring in the dioxanes of sodium drying.The reactant mixture cooling is filtered, and drying with washed with dichloromethane and chromatography purifying, obtains faint yellow solid, and fusing point is 86-88 ℃.
Analyze: C
15H
8C
1O
2SF
3Calculated value C52.2 H2.3
Measured value C51.8 H2.3
Example 4.N-benzyl-5-(2 '-nitro-4 '-4-trifluoromethylphenopendant) phthalimide
N-benzyl-5-hydroxyl-phthalimide (0.84 gram) and potassium hydroxide (0.19 gram) are dissolved in the ethanol (50 milliliters), boil off solvent.Residue is dissolved in the dimethyl sulfoxide (DMSO) (50 milliliters), and adds 4-chloro-3-nitro-three and fluoridize benzene (0.75 gram), and mixture heated 6 hours in the time of 180 ℃ and pours in the water.The mixture ethyl acetate extraction is told ethyl acetate layer, and dry and evaporation obtains light yellow oil.The crystallization in ethanol of this oil is got faint yellow prism, and fusing point is 166-167 ℃.
Analyze: C
22H
13F
8N
2O
5Calculated value: C59.7 H2.9 N6.3
Measured value: C59.8 H3.0 N6.6
Example 5.N-benzyl-5-chloro-4 '-4-trifluoromethylphenopendant)-phthalimide
Undertaken by example 4 same methods, but with 3,4-dichloro three is fluoridized benzene and replaced 4-chloro-3-nitrotrimethylolmethane to fluoridize benzene, the product of wanting that obtains is a white solid, and fusing point is 119-121 ℃
Analyze: C
22H
13F
8C
1NO
2Calculated value: C61.2 H3.0 N3.25%
Measured value: C61.2 H2.9 N3.1%
Example 6.5-(2 '-chloro-4 '-4-trifluoromethylphenopendant)-3-hydroxyl-2-benzo (C) furanone
The product and 20 ml waters of example 2 were added hot reflux 3 days, and reactant mixture divides and desolvates and the chromatography purifying with dichloromethane extraction and dry, obtains the product of wanting, fusing point 145-147 ℃.
Analyze: C
15H
8O
4C
1F
3Calculated value C52.2 H2.3%
Measured value C51.9 H2.4%
Example 7.5-(2 '-chloro-4 '-4-trifluoromethylphenopendant)-3-methoxyl group-2-benzo (C) furanone
A) 5-hydroxyl-2-benzo (C) furanone (5.5 gram) is dissolved in the ethanol (50 milliliters), adds 2.5 gram potassium hydroxide, vlil 3 hours, divide and desolvate, residue is dissolved in the dimethyl sulfoxide (DMSO) (50 milliliters), adds 8.2 grams 3, and 4-dichloro three is fluoridized benzene.Mixture stirred 18 hours under drying nitrogen at 160 ℃, and cooling is poured in the ice then, with watery hydrochloric acid neutralization, product dichloromethane extraction.
B) product (1.5 gram) and the N-bromo-succinimide (0.82 gram) with A is dissolved in the dried carbon tetrachloride (25 milliliters), adds a granule benzoyl peroxide, and reactant mixture refluxes under high light and stirs when the amber imines begins to precipitate.The mixture cooling is filtered, with the carbon tetrachloride washing and except that desolvating.Chromatography (silicagel column; Eluent methylene chloride) makes greenish orange look viscous oil.
C) product of B added hot reflux three days with 20 ml waters, and reactant is also dry with dichloromethane extraction.5-(2 '-chloro-4 that branch desolvates and the chromatography purifying obtains '-4-trifluoromethylphenopendant)-3-hydroxyl-2-benzo (C) furanone, fusing point is 145-147 ℃.This product is indication in the 8-10 example below: hydroxyl-2-benzo (C) furanone.
D) with above-mentioned A)-C) prepared hydroxyl-2-benzo (C) furanone (1.4 gram) adds hot reflux and stirred 2 hours in methyl alcohol.Residual solvent is removed with evaporation, and product is also used eluent methylene chloride with the chromatography purifying on silicagel column, obtain a kind of oil of clarification, should obtain desired product by the oil recrystallization, and fusing point is 67 ℃.
Analyze: C
15H
10C
1F
3O
4Calculated value: C53.6; H2.8; C19.9%
Measured value: C53.6; H2.9; C19.9%
Example 8.5-(2 '-chloro-4 '-fluoroform phenoxy group)-3-acetoxyl group-2-benzo (C) furanone
Hydroxyl-2-benzo (C) furanone (0.7 gram) is added hot reflux and stirred 5 hours in acetic anhydride, excessive acetic anhydride via is removed with evaporation, residue washs with saturated sodium bicarbonate solution, use dichloromethane extraction, organic facies is with the bicarbonate washing and use dried over sodium sulfate.Remove and desolvate, the solid that product obtains with chromatography purifying and recrystallization, 113 ℃ of fusing points.
Analyze: C
17H
10C
1F
3O
5Calculated value: C52.8; H2.6%
Measured value: C53.0; H2.7%
Example 9.5-(2 '-chloro-4 '-fluoroform phenoxy group)-and 3-N ', N '-dimethyl urea groups-2-benzo (C) furanone
Hydroxyl-2-benzo (C) furanone (0.7 gram) is added in the MEK (20 milliliters) of 1.1-dimethyl urea (0.2 gram), and mixture added hot reflux 2 hours, and then added 0.2 gram urea.Through adding hot reflux again after 6 hours, remove and desolvate, residue is suspended in the water and gives a violent shake to remove any nonreactive urea, takes out to place ethyl acetate and chromatography purifying to obtain solid, and fusing point is 154 ℃.
Analyze: C
18H
14N
2O
4C
1F
3Calculated value: C52.7; H3.4; N6.8%
Measured value: C52.0; H3.2; N6.4%
Example 10.5-(2 '-chloro-4 '-4-trifluoromethylphenopendant)-3-3.4-dichloro-benzenes amido-2-benzo (C) furanone
Hydroxyl-2-benzo (C) furanone (1.0 gram) is incorporated in the dry acetonitrile solution (10 milliliters) of 3.4-dichloroaniline (0.5 gram), adds a P-toluenesulfonic acid crystal.Mixture adds hot reflux and stirred 55 hours, removes and desolvates, and residue obtains a kind of solid with the chromatography purifying, and fusing point is 168 ℃.
Analyze: C
21H
11NO
3Cl
3F
3Calculated value: C51.6; H2.2; N2.9
Measured value: C51.6; H2.1; N2.7
Example 11-40.
Following method all is similar to be described in the above-mentioned example, has prepared other compounds, its character and analyze data and all list in table 1, and in whole examples, the evaluation of product is to analyze with nuclear magnetic resonnance (n, m, r).Its empirical formula is determined with mass measurement spectrum accurately in the example of putting on " m, m, a ".Compound is with the substituent R in the following formula
2, A and B discern:
Example 41.Activity of weeding
For estimating the activity of weeding, compound of the present invention is to represent series vegetable to test with following work: corn, zea mays(Mz); Rice, Oryza satva(R); Barnyard grass, Echinohloa crusgalli(BG); Oat, Avena sativa(O); Linseed, Linum usitatissimum(L); Mustard seed, Sinapsis alba(M); Sugar beet, Beta vulgaris(SB) and soybean, Glycine max(S).
Test is divided into two big classes, before emerging and after emerging.Be that liquid agent with compound is sprayed on the earth before emerging, the seed that above-mentioned each kind of plant of just having sowed is arranged in this earth, after the test of emerging comprise two kinds of tests, that is: earth soaks into test and plant spray test, soak into the earth that above-mentioned various plantling growths will be arranged in the experiment at earth and use the liquid preparation that contains the invention compound to soak into, spray in the experiment plant and then same preparation is sprayed plantling.
Used in test earth is the fertile soil on the gardening for preparing.
Formulations employed is that the compound dissolution that will test is made in the middle of containing the acetone soln of the alkylphenol of 0.4% weight/oxirane concentrate in test, and this concentrate can be the product of TRITON X-155 with trade mark.The dosage that these acetone soln dilute with waters are made at last is: per hectare is used 600 liter solution in the test that earth sprays and plant is sprayed, wherein content of active substance is equivalent to 5 kilograms of per hectares or 10 kilograms, uses about 3000 liters of solution to include active matter to be equivalent to 10 kilograms of dosage of per hectare and soak in the experiment per hectare at earth.
The earth that plantling is arranged that the earth of not handling in the test before emerging that sowing is arranged then will not handled after emerging as the control test is as the control experiment.
The weeding ratio of test compound was observed with eyes after spraying plant and earth and is determined in 12 days, and earth is moistening then after 13 days, records 0-9 scale.Grade 0 is meant the growth of the control experiment of not handling, and grade 9 is meant dead situation, and 1 unit of every increase just is bordering on the line style scale increases 10% of efficient equipotential.
In the table II, wherein compound was by discerning with reference to above-mentioned example below result of the test was listed in.
Claims (12)
1, the composition of weeding is characterized in that including the active ingredient of carrier and diphenyl ether derivative, and its general formula I is:
R wherein
1Represent hydrogen or halogen atom or alkyl or halogenated alkyl group, R
2And R
3, can be identical also can be different, each all represents hydrogen or halogen atom or alkyl separately, haloalkyl, nitro or cyano group, A and B, can be identical also can be different, each all separately representative be selected from divalent group of following chemical formula:
>C (R
4)
2-X-;>N-R
5>C=X and>SO
2, when A be-X-or>CO
2The time, B must be different from A nor can be>C=X; Each R
4Can be identical; also can be different, represent hydrogen or halogen atom or alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, alkaryl, alkoxyl, cycloalkyloxy, alkenyloxy, cycloalkyloxy, alkenyloxy, alkynyloxy group, alkoxy carbonyl alkoxyl, alkylthio, acyl group, acyloxy, carboxyl, alkoxy carbonyl or heterocyclic group, a formula NR who replaces or do not replace
6R
7Amido, perhaps as a R
4When being hydrogen atom, alkoxyl or hydrocarbyl group, then another can be a hydroxyl, perhaps two R
4Can represent chemical formula to be=NR together
6Imido grpup; R
5Represent hydrogen atom, carboxyl or hydroxyl, or alkyl, alkoxyl, aralkyl, alkoxy carbonyl or an alkoxy carbonyl alkyl that replaces or do not replace, or formula NR
6R
7Amine; R
6And R
7, can be identical, also can be different, each all represents hydrogen atom or alkyl, aryl or an acyl group that replaces or do not replace; And X, no matter, all represent oxygen or sulphur atom in the formula I or therein in the substituent definition.
2, by the desired composition of claim 1, it is characterized in that wherein active ingredient is the compound of general formula I, wherein the X represention oxygen atom; A represention oxygen atom, carbonyl, C(R
4)
2Base, one of them R
4Base is hydrogen atom, many alkyl or alkoxyl to 4 carbon atoms, or aryl, and another R
4Base is hydrogen or halogen atom, hydroxyl, many alkyl to 4 carbon atoms, how to the alkoxyl that is replaced or do not replace by halogen atom or hydroxyl or alkoxyl of 4 carbon atoms, the cycloalkyloxy that 5-8 carbon atom arranged, many alkenyloxy or alkynyloxy groups, alkoxy carbonyl alkoxyl to 6 carbon atoms, many alkylthio, silane alcohol bases to 4 carbon atoms, pyridine radicals, or formula NR
6R
7Amido, R wherein
6Represent hydrogen atom or how to the alkyl of 4 carbon atoms and R
7Be many to the alkyl of 4 carbon atoms, by at least one halogen atom phenyl that replace or that do not replace or alkyl-carbonyl, alkylamine formyl or an alkyl sulfonic acid base; B represention oxygen atom, C(R
4)
2Base, wherein each R
4, can be the same also can be different, represent hydrogen atom separately or how to the alkyl or the alkoxyl of 4 carbon atoms, or NR
5Base, wherein R
5Be hydrogen atom, many alkyl, benzyl or many alkoxy carbonyl alkyls to 8 carbon atoms to 4 carbon atoms.
3,, it is characterized in that wherein the B represention oxygen atom and A represents C(R by the desired composition of claim 2
4)
2Base, wherein R
4Defined the same with claim 2.
4, by the desired composition of claim 1,2 or 3, it is characterized in that wherein R
1Represent trifluoromethyl group, R
2Represent halogen atom and R
3Represent hydrogen atom.
5, by the desired composition of one of aforesaid right requirement, it is characterized in that containing at least two carriers, wherein have at least one to be surfactant.
6, by at the diphenyl ether derivative of the I of formula shown in the claim 1, it is characterized in that 4-trifluoromethylphenopendant except 4-(2-chloro-4-)-phthalate anhydride, substituting group wherein have in claim 1 fixed connotation.
7, by the desired diphenyl ether of claim 6, the substituting group that it is characterized in that its Chinese style I have in any of claim 2-4 fixed connotation.
8,, it is characterized in that this method comprises and be structural formula by the preparation method of the desired diphenyl ether of claim 6:
Benzo (C) furanone and structural formula be
Compound reaction, wherein A, B, R
1, R
2And R
3Have in claim 6 fixed connotation; Z and Q represent halogen atom or nitro, and other are then represented-the OM group, wherein M represents hydrogen or alkali metal atom, secondly, then react as needs sulfo--2-benzene (C) furanone with phosphorus pentasulfide, perhaps the compound that ought require be halo or have hydroxyl subunit group then with halogenating agent reaction, hydroxyl methene derivant then is hydrolyzed the halogenated methylene derivative of gained and makes.
9, by the desired method of claim 8, it is characterized in that wherein first step reaction is that formula II compound and alkali metal hydrogen oxygen compound with the Q representation hydroxy reacts in the alkanol solvent, the formula III compound that the alkoxide and the Z of gained is the chlorine atom reacts then.
10,, it is characterized in that wherein alkoxide and chlorinated compound III react in organic solvent and under high temperature and inert gas atmosphere by the desired method of claim 9.
11, prevent the method for weeds in locality growth, it is characterized in that this method comprise with the composition in arbitrary claim of 1-5 or in claim 6 or 7 this place of desired compound treatment.
12, press that defined diphenyl ether can be used as weed killer herbicide in any claim of 1-7.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 85101141 CN1023752C (en) | 1983-12-02 | 1985-04-01 | Diphenyl ether herbicides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB838332268A GB8332268D0 (en) | 1983-12-02 | 1983-12-02 | Herbicides |
CN 85101141 CN1023752C (en) | 1983-12-02 | 1985-04-01 | Diphenyl ether herbicides |
Publications (2)
Publication Number | Publication Date |
---|---|
CN85101141A true CN85101141A (en) | 1986-10-08 |
CN1023752C CN1023752C (en) | 1994-02-16 |
Family
ID=25741354
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 85101141 Expired - Fee Related CN1023752C (en) | 1983-12-02 | 1985-04-01 | Diphenyl ether herbicides |
Country Status (1)
Country | Link |
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CN (1) | CN1023752C (en) |
-
1985
- 1985-04-01 CN CN 85101141 patent/CN1023752C/en not_active Expired - Fee Related
Also Published As
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CN1023752C (en) | 1994-02-16 |
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