WO1998028981A1 - Composition herbicide - Google Patents
Composition herbicide Download PDFInfo
- Publication number
- WO1998028981A1 WO1998028981A1 PCT/JP1997/004816 JP9704816W WO9828981A1 WO 1998028981 A1 WO1998028981 A1 WO 1998028981A1 JP 9704816 W JP9704816 W JP 9704816W WO 9828981 A1 WO9828981 A1 WO 9828981A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- herbicidal
- herbicidal composition
- hydrogen atom
- alkyl group
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 42
- 239000000203 mixture Substances 0.000 title claims abstract description 18
- -1 pyrazole compound Chemical class 0.000 claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- 239000003112 inhibitor Substances 0.000 claims abstract description 9
- 230000029553 photosynthesis Effects 0.000 claims abstract description 9
- 238000010672 photosynthesis Methods 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000005476 Bentazone Substances 0.000 claims description 2
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 2
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 229940100050 virazole Drugs 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 19
- 239000004009 herbicide Substances 0.000 description 14
- 240000008042 Zea mays Species 0.000 description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
- 235000005822 corn Nutrition 0.000 description 8
- 241000209140 Triticum Species 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- 239000004480 active ingredient 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 2
- UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 2
- 241001621841 Alopecurus myosuroides Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000005494 Chlorotoluron Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000002147 killing effect Effects 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- OFJBYLCQNJHFMI-UHFFFAOYSA-N 2,5-dihydro-1,2-oxazole Chemical compound C1ONC=C1 OFJBYLCQNJHFMI-UHFFFAOYSA-N 0.000 description 1
- OFRMTRNULBCTHS-UHFFFAOYSA-N 2-[2-[2-[2-[bis(carboxymethyl)amino]-5-(2-diazoacetyl)phenoxy]ethoxy]-N-(carboxymethyl)-4-(2-diazoacetyl)anilino]acetic acid Chemical compound C(=O)(O)CN(C1=C(OCCOC2=C(C=CC(=C2)C(C=[N+]=[N-])=O)N(CC(=O)O)CC(=O)O)C=C(C=C1)C(C=[N+]=[N-])=O)CC(=O)O OFRMTRNULBCTHS-UHFFFAOYSA-N 0.000 description 1
- CZKKIYPWLBINSU-UHFFFAOYSA-N 2-[3-[2-[2-[bis(carboxymethyl)amino]-5-methylphenoxy]ethoxy]-N-(carboxymethyl)-4-(2-diazoacetyl)anilino]acetic acid Chemical compound Cc1ccc(N(CC(O)=O)CC(O)=O)c(OCCOc2cc(ccc2C(=O)C=[N+]=[N-])N(CC(O)=O)CC(O)=O)c1 CZKKIYPWLBINSU-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ZLEUYGBJFPTXLX-UHFFFAOYSA-N C1C=[S+]NC1 Chemical compound C1C=[S+]NC1 ZLEUYGBJFPTXLX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000194101 Ginkgo biloba Species 0.000 description 1
- 235000008100 Ginkgo biloba Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 240000001812 Hyssopus officinalis Species 0.000 description 1
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 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
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 241000534944 Thia Species 0.000 description 1
- 239000004963 Torlon Substances 0.000 description 1
- 229920003997 Torlon® Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- PDAVOLCVHOKLEO-UHFFFAOYSA-N acetyl benzenecarboperoxoate Chemical compound CC(=O)OOC(=O)C1=CC=CC=C1 PDAVOLCVHOKLEO-UHFFFAOYSA-N 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 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
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene 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
- A01N43/72—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
- A01N43/80—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 1,2
Definitions
- the present invention relates to a herbicidal composition which, by mixing two herbicides, exhibits a synergistic effect as well as an additive effect of the individual herbicides.
- Pyrazole compounds which are one active ingredient of the herbicidal composition of the present invention, are disclosed in WO96 / 26206, WO97 / 411105 and WO97 ⁇ 4111 It is described in the official gazette.
- R ', R 2 each independently represent a hydrogen atom, C, and e alkyl group
- M, L are each independently a hydrogen atom, a halogen atom, C, - 6 alkyl group , C, - «alkoxy group, S 0 2 R 3 (R 3 is;. represents an alkyl group), etc. represent
- Z is also saturated 5 or 6 membered properly a heterocyclic group unsaturated represents
- R 4 represents a a group represented by the hydrogen atom or S 0 2 a r.
- An object of the present invention is to provide a herbicidal composition which is safe for corn and wheat and can be completely controlled from a one-year to a perennial weed at a low dose.
- DISCLOSURE OF THE INVENTION The present inventors have added to the compounds represented by the formula [I] below, atrazine, isoprolone, cyanadine, chlorotoluron, benzozone, and xyoxinil. It has been found that when one or two or more photosynthesis inhibitors such as the above are mixed in a predetermined ratio, not only the respective herbicidal effects can be obtained additively but also a synergistic herbicidal effect appears. .
- the combined use of the two drugs expands the range of weed killing beyond the application range obtained with each single agent, and at the same time achieves faster completion of the weed killing effect.
- the present inventors have found that a sufficient effect can be exerted at a dose lower than the dose, as well as the safety against corn and wheat, and that a single treatment can exhibit a sufficient herbicidal effect, thereby completing the present invention.
- the present invention provides a compound of the formula [I]
- R 1 and R 2 each independently represent a hydrogen atom, an alkyl group or a C alkenyl group
- M and L each independently represent a hydrogen atom, a halogen atom, C, — «; alkyl Group, alkoxy group, SR 3 , S 0 R 3 , S 0 R 3
- R 3 represents a C, — "alkyl group.), A cyano group or a nitro group, Z represents a 5- or 6-membered saturated or unsaturated heterocyclic group, and R 4 represents A hydrogen atom, a group represented by CH 2 A r, CH 2 C 0 A r or S 0 2 A r (A r has a substituent P97 / 04816 represents a funinyl group which may be substituted. ).
- a herbicidal composition comprising a biazole compound represented by the formula: and a photosynthesis inhibitor.
- BEST MODE FOR CARRYING OUT THE INVENTION The composition of the present invention generally depends on the relative activity of each component, but is generally a compound represented by the above formula [I] per 1 part by weight of a photosynthesis inhibitor. Is contained in an amount of 0.0001 to 50 parts by weight, preferably 0.001 to 10 parts by weight.
- One active ingredient of the composition of the present invention is a compound represented by the formula [I].
- R 1 and R 2 are each independently a hydrogen atom, methyl, ethyl, propyl, isopropyl, butyl, isoptyl, sec-butyl, butyl, etc. — Represents a G alkyl group, or C,-(i alkenyl group such as 1-probenyl, 2-provenyl, 1-butenyl, 2-butenyl, 3-butenyl group.
- M and L are each independently a hydrogen atom, a halogen atom such as fluorine, chlorine, bromine, or iodine, methyl, ethyl, propyl, isopropyl, butyl, isoptyl, sec-butyl, t-butyl group C alkyl group, such as, main butoxy, et butoxy, Purobokishi, C, such as Lee isopropoxy group, -; alkoxy group, main Chiruchio, Echiru Chio, a group represented by SR 3, such as a propylthio group, Mechirusurufu Weniru, Echiru Surufuweniru , A group represented by S 0 R : i such as a propylsulfenyl group; a group represented by S 0 2 R 3 such as a methylsulfonyl, ethylsulfonyl, and propylsulfonyl group (R
- Z represents a 5- or 6-membered saturated or unsaturated heterocyclic group.
- Examples of the 5-membered unsaturated heterocyclic group represented by Z include 2-furyl, 3-furyl, 2-phenyl, 3-phenyl, 2-pyrrolyl, 3-pyrrolyl, 2 — oxazolyl, 4 year old oxazolyl, 5 — year old oxazolyl, 3 — isosoxazolyl, 4 ⁇ 1 oxoxazolyl, 5 — isosoxazolyl, 3 — isisothiazolyl, 4 ⁇ 1 isothiazolyl, 5 — a Sothiazolyl, 2 — imidazolyl, 4 — imidazolyl, 3 — villazolyl, 4 1 villazolyl, 1, 2, 4 oxaziazoloneru 3 — yl, 1, 2, 4 — oxaziazolulu 5 —Ill, 1,3,4 Oxazia
- 6-membered unsaturated heterocyclic groups include 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyridinyl, 3-pyrazinyl, 2-pyrimidinyl, and 4-pyridinyl. Midinyl, 5—pyrimidinyl, 3—pyridazinyl, 4-pyridazinyl, 1,3,5—triazine-1-2-yl, 1,2,4, triazine-1-5-yl , 1, 2, 4 — Triazine 1-3-yl, 1, 2, 4-Triazine 6-yl, 1, 2, 4, 5 — Tetrazine 1-3-yl group And the like.
- saturated 5- or 6-membered heterocyclic groups include 2-tetrahydrofuranil, 3-tetrahydrofuranyl, 2-tetrahydrochenyl, and 3-tetrahydrofuranyl.
- Trahidrochirenil Tetrahidrochiopyran-1 2-yl, Tetrahidrochiopyran-1 3-yl, Tetrahidrochiopyran_41-yl, 1,3—Dithia N 1 2 — yl, 1,
- R represents a hydrogen atom, CH 2 A r, the group represented by CHC 0 A r or S 0 2 A r.
- Ar is located at any position on the benzene ring, such as halogen atoms such as fluorine, chlorine and bromine, and-, such as methyl groups, alkyl groups, and methoxy groups, etc.
- the compound represented by the formula [I] has excellent herbicidal activity by itself. In particular, it has little phytotoxicity to corn and wheat, and has an excellent herbicidal effect against weeds such as ginkgo biloba, crabgrass, embak, ichibi, and inubu.
- Ts represents a 4-toluenesulfonyl group; the same applies hereinafter Table 2 (continued)
- the photosynthesis inhibitor which is another active ingredient of the composition of the present invention, has relatively low phytotoxicity to grasses such as corn and barley, and is a broadleaf weed such as nubu, ichibi and blackgrass. It is a herbicide that is active on a very small number of grass weeds and is characterized by many drugs with a narrow herbicidal spectrum.
- Such photosynthesis inhibitors include, for example, atrazine, isoprolone, cyanadine, chlorotoluron, benzazone, and ioxynil.
- the herbicidal composition of the present invention can be used in the form of a mixture without adding other components, or in a form that can be taken by a general pesticide for use as a pesticide. That is, they can be used in the form of wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, flowables and the like.
- plant powders such as soybean flour and flour, diatomaceous earth, apatite, gypsum, talc, bentona Mineral powders such as it, pyrophyllite and clay, and organic and inorganic compounds such as sodium benzoate, urea and sodium sulfate are used.
- organic and inorganic compounds such as sodium benzoate, urea and sodium sulfate are used.
- petroleum components such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetate , Trichloroethylene, methylisobutylketone, mineral oil, vegetable oil, water, etc. are used as solvents.
- a surfactant can be added, if necessary, to obtain a uniform and stable form.
- the wettable powder and emulsion thus obtained are diluted to a predetermined concentration with water to form a suspension or an emulsion, and the granules are used as they are before or after germination of the weeds. Spraying or soil mixing. Actually, in applying the herbicide of the present invention, an appropriate amount of 0.1 g or more of the active ingredient per hectare is applied.
- the individual active compounds often exhibit disadvantages in their herbicidal activity, however, if they are greater than the simple sum (the expected value) of the respective activities of the two compounds. This is called a synergistic effect.
- the expected activity of a particular combination of two herbicides can be calculated as follows (Co 1 by S, R. Calculation of synergistic and antagonistic response of a herbicide combination "W eeds ", Vol. 15, pages 20-22, 1967.
- indices of 3, 5, 7, and 9 indicate values intermediate between 0, 22, 22, 44, 6, 6, 88, and 10, respectively.
- the herbicidal composition of the present invention is suitable as a herbicide for controlling corn and wheat weeds and is industrially useful.
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Abstract
Cette invention concerne une composition herbicide comportant un composé pyrazole représenté par la formule générale (I) et un inhibiteur de photosynthèse du type atrazine ou isoproturon. Dans la formule (I), R1 et R2 sont indépendamment hydrogène, alkyle C¿1-6?, etc.; M et L sont indépendamment hydrogène, halogéno, alkyle C1-6, alcoxy C1-6, SO2R?3 (où R3¿ est alkyle C¿1-6?), etc.; Z représente un hétérocycle (in)saturé à cinq ou six éléments; et R?4¿ est hydrogène, un groupe représenté par CH¿2?Ar ou SO2Ar (où Ar représente un phényle éventuellement substitué), etc.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP36006796 | 1996-12-27 | ||
| JP8/360067 | 1996-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1998028981A1 true WO1998028981A1 (fr) | 1998-07-09 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1997/004816 WO1998028981A1 (fr) | 1996-12-27 | 1997-12-25 | Composition herbicide |
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| WO (1) | WO1998028981A1 (fr) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999065314A1 (fr) * | 1998-06-16 | 1999-12-23 | Basf Aktiengesellschaft | Melanges herbicides a effet synergique |
| EP0900795A4 (fr) * | 1996-04-26 | 2000-12-13 | Nippon Soda Co | Derives du benzene substitues par des heterocycles, et herbicides |
| WO2001028341A3 (fr) * | 1999-10-22 | 2002-05-02 | Aventis Cropscience Gmbh | Agents herbicides synergetiques contenant des herbicides faisant partie du groupe des inhibiteurs de l'hydroxyphenylpyruvate dioxygenase |
| US6433082B1 (en) | 1998-06-26 | 2002-08-13 | Bayer Aktiengesellschaft | Herbicidal mixtures exhibiting a synergistics effect |
| US6610631B1 (en) | 1999-09-30 | 2003-08-26 | Bayer Aktiengesellschaft | Substituted aryl ketones |
| US6746989B1 (en) | 1999-03-27 | 2004-06-08 | Bayer Aktiengesellschaft | Substituted benzoylpyrazoles as herbicides |
| US6864219B2 (en) | 2000-01-17 | 2005-03-08 | Bayer Aktiengesellschaft | Substituted aryl ketones |
| US7112554B2 (en) | 2001-05-09 | 2006-09-26 | Bayer Cropscience Ag | Substituted arylketones |
| US7153813B2 (en) | 2002-02-19 | 2006-12-26 | Bayer Aktiengesellschaft | Substituted aryl ketones |
| US7807703B2 (en) | 2002-03-05 | 2010-10-05 | Bayer Cropscience Ag | Substituted aryl ketones |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996026206A1 (fr) * | 1995-02-24 | 1996-08-29 | Basf Aktiengesellschaft | Derives de pyrazol-4-yl-benzoyle et leur utilisation comme herbicides |
| WO1997041118A1 (fr) * | 1996-04-26 | 1997-11-06 | Nippon Soda Co., Ltd. | Derives du benzene substitues par des heterocycles, et herbicides |
| WO1997041105A1 (fr) * | 1996-04-26 | 1997-11-06 | Nippon Soda Co., Ltd. | Nouveaux derives de benzene a substitution heterocycle et herbicides |
| WO1997041117A1 (fr) * | 1996-04-26 | 1997-11-06 | Nippon Soda Co., Ltd. | Nouveaux derives du benzene substitues par des heterocycles, et herbicides |
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- 1997-12-25 WO PCT/JP1997/004816 patent/WO1998028981A1/fr active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996026206A1 (fr) * | 1995-02-24 | 1996-08-29 | Basf Aktiengesellschaft | Derives de pyrazol-4-yl-benzoyle et leur utilisation comme herbicides |
| WO1997041118A1 (fr) * | 1996-04-26 | 1997-11-06 | Nippon Soda Co., Ltd. | Derives du benzene substitues par des heterocycles, et herbicides |
| WO1997041105A1 (fr) * | 1996-04-26 | 1997-11-06 | Nippon Soda Co., Ltd. | Nouveaux derives de benzene a substitution heterocycle et herbicides |
| WO1997041117A1 (fr) * | 1996-04-26 | 1997-11-06 | Nippon Soda Co., Ltd. | Nouveaux derives du benzene substitues par des heterocycles, et herbicides |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0900795A4 (fr) * | 1996-04-26 | 2000-12-13 | Nippon Soda Co | Derives du benzene substitues par des heterocycles, et herbicides |
| WO1999065314A1 (fr) * | 1998-06-16 | 1999-12-23 | Basf Aktiengesellschaft | Melanges herbicides a effet synergique |
| JP4646403B2 (ja) * | 1998-06-16 | 2011-03-09 | ビーエーエスエフ ソシエタス・ヨーロピア | 相乗効果を有する除草剤混合物 |
| JP2002518303A (ja) * | 1998-06-16 | 2002-06-25 | ビーエーエスエフ アクチェンゲゼルシャフト | 相乗効果を有する除草剤混合物 |
| US6534444B1 (en) | 1998-06-16 | 2003-03-18 | Basf Aktiengesellschaft | Herbicidal mixtures having a synergistic effect |
| US7842646B2 (en) | 1998-06-16 | 2010-11-30 | Basf Se | Synergistically acting herbicidal mixtures |
| US6908883B2 (en) | 1998-06-16 | 2005-06-21 | Basf Ag | Synergistically acting herbicidal mixtures |
| US6433082B1 (en) | 1998-06-26 | 2002-08-13 | Bayer Aktiengesellschaft | Herbicidal mixtures exhibiting a synergistics effect |
| US6746989B1 (en) | 1999-03-27 | 2004-06-08 | Bayer Aktiengesellschaft | Substituted benzoylpyrazoles as herbicides |
| US7279444B2 (en) | 1999-03-27 | 2007-10-09 | Bayer Cropscience Gmbh | Substituted benzoylpyrazoles |
| US6727206B2 (en) | 1999-09-30 | 2004-04-27 | Bayer Aktiengesellschaft | Substituted aryl ketones |
| US6610631B1 (en) | 1999-09-30 | 2003-08-26 | Bayer Aktiengesellschaft | Substituted aryl ketones |
| WO2001028341A3 (fr) * | 1999-10-22 | 2002-05-02 | Aventis Cropscience Gmbh | Agents herbicides synergetiques contenant des herbicides faisant partie du groupe des inhibiteurs de l'hydroxyphenylpyruvate dioxygenase |
| EP1913816A3 (fr) * | 1999-10-22 | 2012-05-23 | Bayer CropScience AG | Agents herbicides synergétiques contenant des herbicides faisant partie du groupe des inhibiteurs de l'hydroxyphenylpyruvate dioxygenase |
| US6864219B2 (en) | 2000-01-17 | 2005-03-08 | Bayer Aktiengesellschaft | Substituted aryl ketones |
| US7112554B2 (en) | 2001-05-09 | 2006-09-26 | Bayer Cropscience Ag | Substituted arylketones |
| US7456133B2 (en) | 2001-05-09 | 2008-11-25 | Bayer Cropscience Ag | Substituted arylketones |
| US7153813B2 (en) | 2002-02-19 | 2006-12-26 | Bayer Aktiengesellschaft | Substituted aryl ketones |
| US7807703B2 (en) | 2002-03-05 | 2010-10-05 | Bayer Cropscience Ag | Substituted aryl ketones |
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